Previously, Glover spent 30 years as a labor employment trial attorney in Chicago, earning a reputation as an aggressive courtroom litigator. His legal career ended in 1995 when he was indicted on 33 counts of white-collar crimes — including kickbacks, bribery, and tampering with government witnesses — and subsequently sentenced to federal prison. He refused to cooperate with prosecutors to reduce his sentence, and served approximately five years before beginning what would become a second career launched from scratch in his fifties.

Released in 2001 with his law license revoked and ineligible for reinstatement for 13 years, Glover rebuilt entirely as a coach, eventually building a national practice. He structures his engagements as one-year contracts with 50 percent of his fee contingent on clients achieving mutually defined goals — a model designed to give him skin in the game and eliminate the incentive to let clients off the hook. His coaching approach draws directly from his own reckoning with ego, echo chambers, and the moment accountability finally broke through.

Glover is the author of WorkQuake™, a book on surviving and thriving in the Knowledge Economy, praised by executive coach Marshall Goldsmith as agitating “the business status quo.”

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, Joshua served as a multimedia journalist at The Hill, where he covered federal policy across energy, healthcare, immigration, defense, and criminal justice, and reported from the front lines of multiple high-stakes election cycles. His background as a news producer — shooting, editing, and cutting four to five videos per day — gave him the operational reps and editorial instinct that now underpin his consulting work.

Joshua holds an M.A. in Communication, Culture and Technology from Georgetown University and a B.A. in Journalism and Mass Communications from The George Washington University. He is a member of The Telly Awards Judging Council and publishes The Comms Chief on Substack.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, Adam co-founded AbstractOps, which raised approximately $10 million from tier-one venture capital firms before pivoting in 2022, with its operations arm spinning off to become Chore. Across his earlier three venture-backed companies, he raised a combined $30 to $40 million in funding, with one company acquired for $400 million. He also served as a Product Manager at Twitter before turning full-time to founding and investing.

Adam holds a JD/MBA and a degree from Vanderbilt University. He co-founded the Autopilot Fund, an investment vehicle focused on AI-related data sets, and hosts the Entrepreneurial Excellence Podcast, where he interviews founders on the operational realities of building companies.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Caden Damiano is a software designer and product manager who has spent his career untangling problems in industries most people overlook — tertiary finance, real estate technology, working capital for agriculture, and financial operations for small and mid-size businesses. He hosts Way of Product, a podcast and Substack newsletter where, over eight years and 180+ episodes, he has interviewed designers, PMs, and engineers about how good work actually gets done.

BottleKeeper’s growth was neither gradual nor accidental. In August 2014, when Facebook launched its video ad platform, Callinan shot a clip of the product in motion and watched monthly revenue spike from $2,000 to $40,000 to $60,000 to $80,000 to $150,000 in a matter of months. He spent the next several years doing it almost entirely himself — handling customer service, paid advertising, creative, and the website — while his cousin managed finance and fulfillment. The company appeared on Shark Tank before eventually selling to a private equity buyer.

Callinan lives in Bozeman, Montana, where he pursues hard physical experiences outdoors as deliberate mental conditioning — a framework he traces directly to resilience under business adversity. He actively mentors founders and business owners.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

In 2011, Ries outlined the idea for a fundamentally different kind of stock exchange inside The Lean Startup. He spent the better part of a decade making it real: the Long-Term Stock Exchange (LTSE) received SEC approval as a national exchange in 2019 and launched trading in September 2020, designed expressly for companies committed to long-term value creation over short-term shareholder extraction. He has since co-founded Answer.ai with Jeremy Howard of fast.ai — an AI research lab focused on practical applications — and founded Virgil, a startup law firm designed around founder needs rather than billable hours.

Incorruptible draws on more than 200 years of case studies — from Johnson & Johnson and Costco to Novo Nordisk and Ikea — to argue that the governance structures most companies adopt by default are engineered to destroy the values that made them worth building. Ries’s thesis: companies that last aren’t those with better culture decks, but those whose founders protected the organizational structure before they lost control of it.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, Wells spent seven and a half years at Twilio, ascending from individual contributor to Senior Director of Engineering before departing in 2021. At Twilio, he oversaw large engineering organizations and was responsible for cloud infrastructure operations — the environment where he first watched runaway AWS and Snowflake costs become six-figure surprises and developed the discipline around inference limits and cost management that now shapes BrainGrid’s architecture. Earlier in his career, he held engineering roles at Skype and Microsoft, accumulating more than 25 years of professional software engineering experience across the stack.

Wells is also the host of the Data Chaos Podcast and previously co-founded Propel Data, a prior analytics venture. He returned to individual-contributor engineering work when he co-founded BrainGrid — a deliberate choice to get back to building after years in senior management — and now operates a three-person team shipping product with parallel agent fleets across isolated Git worktrees.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, as Senior Manager and Director in the IT Capital Markets Services practice at EY, Koren spent more than a decade advising Fortune 500 clients across financial services, auto insurance, energy, and professional services sectors in North America and Europe. He was recognized as a top 1 percent performer and became known for deploying enterprise-scale work management applications — hands-on experience in the client service delivery cycle that would later define Sembly’s product thesis.

Earlier in his career, Koren served as CEO and CTO of Visual Trading Systems, where he built and distributed technology solutions for the capital and commodity markets, and co-founded Neusana, applying deep learning to digital biopsy image analysis. He holds a BS in Computer Science and Economics from Columbia University and an MBA from NYU Stern School of Business.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, as Advanced Analytics Product Manager at Nike, he supported planning tools for the Asia and Latin America regions and drove forecast accuracy from 65% to 93% over six seasons by introducing consumer profile modeling — one of the more precisely measured single-initiative improvements in Nike’s planning systems during that period. He also held product and engineering roles at Amazon Web Services before founding Deci Media, building the enterprise-scale data infrastructure background that informs Decisio’s deterministic recommendation architecture.

His career highlights span 20 years split evenly between two disciplines: 10 years as a database engineer specializing in machine learning and advanced analytics, followed by 10 years in product management across enterprise software organizations. Headquartered in Beaverton, Oregon, Deci Media is built on the conviction that streaming platforms’ 33% abandonment rate and 50% viewer dissatisfaction rate are not failures of recommendation algorithms — they are the predictable result of platforms optimized for engagement metrics rather than viewer satisfaction.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, he built a product marketing career spanning over 20 years, beginning his first marketing work at age 14 and later advancing through digital marketing roles during a year spent in Australia and six months in China studying Mandarin. His pivot into podcast strategy in the early 2020s was grounded in a specific observation about buyer behavior: following the Google 7-11-4 rule — which holds that B2B buyers require 7 hours of content engagement across 11 touchpoints on 4 different platforms before converting — a single repurposed podcast episode is the most efficient vehicle for hitting those numbers at founder scale.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, as DevOps Culture Enablement lead at Red Hat across Europe and the Middle East, he helped enterprises adopt agile and DevOps as genuine operating philosophies rather than compliance exercises. He became known for identifying and naming what he called “dishonest agile” — the practice of assembling project teams that disbanded immediately after delivery, contradicting the continuity and learning loops that agile methods require. His regional scope encompassed enterprises across two continents during a period of significant enterprise digital transformation.

His career highlights include 25 years across major consulting firms, including IBM and several boutique professional services organizations, where he observed firsthand how time-and-materials billing structurally rewards complexity and delay over outcomes — a dynamic he documented in DevOps Culture and Practice with OpenShift, a practitioner guide integrating lean, agile, and design thinking with hands-on technical enablement. That book, and the framework behind Stellafai, reflect a consistent career mission: making consulting less wasteful, more accountable, and more genuinely enabling.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, as Vice President of Marketing at Particle Health, Sarunac led the company’s marketing function from Series A through Series B over 3.5 years, building a data-driven, analytics-first growth strategy centered on revenue outcomes, cross-channel experimentation, and A/B testing across market segments. Her work established Particle Health as a trusted, humanized brand within the health data interoperability space, spanning web design, conference presence, and content programs.

Earlier in her career, as Director of Marketing at Ideon — formerly Vericred, an API platform simplifying health insurance and employee benefits data exchange — Sarunac ran full-spectrum marketing operations including content strategy, PR, SEO, and trade show execution. She directly attributed 40% of all inbound website traffic to marketing initiatives, with an additional 40% driven by an SEO program she built and managed over two years.

At The Company Advice, she created The Healthies, the first awards program recognizing excellence in marketing, branding, and product design in digital health, expanding the firm’s footprint as a thought leadership platform for the sector.

Thanks for reading this far. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Dean Phillips is the Head of Product Strategy at ClickUp, where he leads the product direction for ClickUp Docs and the company’s emerging AI-powered Super Agents. Rising to prominence in the early 2020s, he became known for translating complex workflows into opinionated, high-leverage product systems inside a platform used by millions of users worldwide. At ClickUp, he currently oversees strategic initiatives that connect document creation, task management, and AI automation into a single unified experience.

Previously, as Head of Product Strategy and Product Manager at ClickUp, he helped scale the product organization through more than five years of rapid growth, serving in core product roles from December 2020 through at least early 2026. He became known for shipping multi-quarter initiatives that spanned Docs, collaboration surfaces, and workflow automation, partnering closely with engineering and data teams to improve productivity at scale. Before ClickUp, he served as Chief Technology Officer at The Pattern Trader, where over four and a half years he led full-stack product and technology efforts for a trading and analytics platform.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

Adam Nash holds degrees in computer science with a focus on human-computer interaction, an MBA from Harvard, and has spent 25 years working at the overlap of engineering, design, and finance. His read: the best product work isn’t about solving rational problems — it’s about designing around the ways humans reliably behave irrationally. He built that argument across eBay, LinkedIn, Wealthfront, and now Daffy — where every feature exists to close the gap between what people want to do and what they actually do.

About forty minutes into our conversation, Adam Nash confesses something I believe to be the crux of our conversation.

“The anxiety I have alone — still, I don’t know how it is — I am almost 50 years old,” he says, “my anxiety in a hotel room of accidentally moving one of those items in the minibar and being charged for it is not rational. But it’s somehow very deep-seated.”

I almost laugh. Not at him — with him. Because Adam Nash is, by any reasonable measure, the person you’d least expect to be intimidated by a hotel minibar. He teaches a Stanford class called Personal Finance for Engineers. He ran Wealthfront. He was VP of Product at LinkedIn through the IPO. He was CEO of a fintech company that managed billions of dollars on behalf of its customers. If anyone on Earth should be able to glance at a $9 Toblerone and shrug, it’s him.

Instead, he tells me he gets nervous about it. And the way he tells me is what I keep thinking about. He doesn’t dress it up. He doesn’t make it a metaphor first and a confession second. He says it the way you’d admit to a friend at a bar that you still get butterflies before flying. The point isn’t that minibar anxiety is interesting. The point is that even Adam — the guy who has designed financial products for two decades — still has it. And that’s the entire thesis of his career.

We’ve been talking about Daffy, the company he founded in 2020. Daffy stands for the Donor Advised Fund For You, and it’s exactly what it sounds like: a tax-advantaged account for charitable giving. You put money in. It invests tax-free. Whenever you’re inspired to give, you go in, pick a charity, send the money. The wealthy have had access to this product for decades — Fidelity, Schwab, and Vanguard all offer one — but most people have never heard of it.

That gap, Adam tells me, is the entire opportunity. And the gap exists not because the math is hard, but because of something much stranger: people are not rational about money. Especially their own.

“Money is very rational,” he tells me. “Dollars and cents, right? You know, the math adds up. Like it’s either a good return or a bad return.” He says it the way someone reads aloud from a textbook they don’t fully agree with. Then he pivots. “But in the end, what’s the money for gets back to people — and people have feelings about money. They have feelings about what they’re doing with it, how they earned it, how they spend it, et cetera.”

This is the move that runs through everything he’s built. He stages the rational view first — the one MBAs are trained on, the one accountants live inside — and then he pulls it apart. Not because the rational view is wrong. Because it’s incomplete in the only way that matters: it doesn’t account for the actual humans who use the product.

I ask him how that lens — the irrationality lens — got into his work. He goes back to the early days of his career, when design was treated, in his words, “as almost an accessory marketing function — like make it pretty. Um, oh, make sure the brand is correct, the colors and text.” He’s not bitter about it, but you can hear something in the cadence — a person who watched an entire discipline be miscategorized for years and decided, at some point, to fix it where he could.

When he got to LinkedIn, he sat down with Reid Hoffman and made an argument that the company needed a horizontal design team — a team whose responsibility was the end-to-end experience, not any single page or feature. He’d spent his eBay years watching Web 1.0 products turn into “a library of pages and not really a product, not really an experience.” He didn’t want LinkedIn to become that. The team he built is still there.

But the more interesting story, to me, is what happened earlier. The career detail he drops almost as a footnote.

“I actually started,” he says, “I thought I was interviewing at a company called NeXT, but it turns out Apple acquired them in the middle. So I was there when Steve came back.”

He says this the way some people mention their college roommate. He worked on Rhapsody, which became Mac OS 10, which became the operating system most of us spent the next two decades using. He was there for the moment when Steve Jobs walked back into Apple and the entire trajectory of consumer computing changed. He’s not bragging. He’s setting up a different point. The Apple culture he watched — and later the Pixar culture he studied through Ed Catmull’s Creativity, Inc. — taught him that great products are made when designers, engineers, and operators don’t fight each other for primacy. They take each other’s instincts seriously.

“If they came up with an idea, there must be a good reason for it,” he says, paraphrasing the Pixar engineering team’s posture toward design. “Let’s figure out how to make that real and make that as excellent as possible.” And vice versa. It’s the win-win posture, he says, that makes a team transcend its parts.

I’ve worked at companies where this happens and at companies where it doesn’t, and the difference is night and day. He doesn’t romanticize it. He’s quick to point out the failure mode. “There’s a hubris that can set in with different roles,” he tells me, “where people decide that — no, engineering is the most important role, we can’t do this without it. Design is the most important role. And of course, product folks — product is the most important role.” He pauses, like he’s actually testing the claim against his own memory. “I think it misses the big picture.”

The big picture, in Adam’s telling, is that no one function ever shipped anything beautiful by itself. Beautiful products require people who can hold multiple frames at once. And the highest-value frame, in his career, has been the one that takes irrationality seriously.

I want to know how that frame translated into Daffy. So I ask him about a feature I noticed — the auto-deposit. You can have money debited from your account every week, every month, into your Daffy fund, before you ever decide where to give it. To me, that’s the whole product. You’ve already mentally separated the money from your life. By the time you sit down to give, the friction is gone.

He nods. This is the move he’s most proud of, I can tell, because his whole tone shifts. He starts using the word “we” more — the team voice. And he starts walking me through what he calls the most important insight of the company.

“Giving involves not one, but two hard problems for most people,” he says. “One is how much can I afford to give? And two, who do I give the money to? And the worst thing about the transactional system that we currently have is that you get hit with both of those problems.”

I have to stop and write this down, because it’s the cleanest articulation of a pattern I’ve watched fail thousands of people in dozens of contexts. Every donation page on the internet asks you both questions at the same time. Pick a charity. Pick an amount. Right now. Most people stall on one or the other and end up doing nothing. Or they default to the easiest option — give five dollars to a friend’s GoFundMe — and feel vaguely guilty that this isn’t what they meant by “I want to be generous.”

Adam tells me about the customer research he did before founding Daffy. He went around the country, talking to people about their giving. The thing that struck him wasn’t the diversity of opinions — though there was plenty of that. It was the consistency of one specific moment.

“You ask them how much they think they should give to charity every year — most people have an idea of what that is. But you ask them, did they hit their goal? And they all end up with this pregnant pause of no, you know, life got in the way, it got busy.”

The pregnant pause. He says it like he heard it dozens of times and stopped being able to un-hear it. Everyone had a number. Almost no one hit it. And the gap between intention and action — what he calls the Generosity Gap — wasn’t a values problem. It was a design problem.

This is the moment in our conversation when I realize what he’s actually doing at Daffy. He’s not trying to convince anyone to give more. He’s trying to remove the design friction that keeps generous people from acting on their own intent. The same way a 401(k) doesn’t make you save more — it just removes the moment of decision that you would otherwise fail at.

“It turns out with money, with finance, automating these things gets you to your goal more reliably and faster,” he says. “If we can do this with saving and investing, why can’t we do this with giving?”

He keeps coming back to this. The rational thing — the thing the textbook would say — is that adults should be able to set a giving goal and meet it through willpower. But adults can’t. And not because they’re bad. Because the system is built against them.

We get into the part of his thinking that he wrote about more than a decade ago, in an essay he called Finding the Heat. He tells me about being in marketing meetings where everyone wanted to talk about the brand’s positive attributes — hope, security, control. He’d push back. “We look at half the problem,” he tells me. “The world isn’t just filled with positive feelings.”

The negative emotions matter just as much. Maybe more. Fear. Anxiety. Embarrassment. The fear of messing something up. The fear of being charged for the minibar item you didn’t actually take. He’s not being cute when he tells me this — he’s giving me the same example he probably gave a marketing team a decade ago. Money has heat. If you design as if it doesn’t, you’re missing the actual problem.

And this is the place where his framework finally lands for me. Designers, when they’re doing the job at full strength, are behavioral economists. They’re not arranging pixels. They’re studying the predictable ways humans fail to do what they say they want to do — and then designing around it. The button isn’t bigger because bigger is prettier. The button is bigger because there’s a moment of doubt that you have to walk the user through. The default is opt-in because the literature on defaults is conclusive. The deposit happens before the decision because the research on pre-commitment is overwhelming.

Adam doesn’t say it this way. He doesn’t have to. The whole conversation is the proof.

I bring up Rory Sutherland — the Ogilvy executive who’s spent his career arguing that most things fail because we apply rational solutions to emotional problems. Adam smiles at the framing. He partly agrees. But he wants to add a wrinkle.

“I don’t know if you’ve met rational humans,” he says. “Please let me know. I know there are 8 billion on the planet. I’ve not met all.” He’s joking, but the joke has teeth. The framing of “rational vs. emotional” is itself a category error. There aren’t two camps. There’s one camp — humans — and they all have feelings about money, even when they’re trying not to. Even Adam. Even in a hotel.

We talk about Daffy Campaigns, the feature that lets members fundraise for causes and offer matching donations. He tells me about a member whose parent — a teacher — had passed away two decades earlier. On the anniversary of the death, the member ran a campaign to raise money for students. “That kind of story is not going to come out of a marketing team,” Adam tells me. “That kind of story is not going to come out of a corporate kind of process. These are personal stories that people are telling.”

He says it quietly. We’ve been talking for over an hour and the energy in his voice has settled into something I’d call admiration — for the people using the product more than for the product itself. He keeps saying “we” when he talks about Daffy, but when he talks about the campaigns, he says “they.” The members. The givers. The teacher’s child. The company is the scaffolding. The campaigns are the building.

I ask him to wrap things up however he wants. He doesn’t pitch. He doesn’t ask anyone to download anything. He says one thing that I’ll keep returning to.

“It really does feel good,” he tells me, “to realize that some of the benefit of your skill, of your work, of your life, could benefit others.”

Then, almost as an afterthought, he tells me what people say after they’ve used the product for a while. It’s not that they saved money on taxes. It’s not that the interface was nice. It’s that the product made them feel good about how they were teaching the next generation.

Which is, I realize after we sign off, the most behavioral-economics thing he could have told me. The product’s measurable outputs — dollars donated, accounts opened, charities funded — are not what closes the loop with the user. The feeling does. The story they tell themselves about who they are when they use it. The image of their kid asking what the donation is for, and them having an answer.

That’s the gap that was always there. Adam built a product that closed it. And the only reason he could see the gap in the first place is that he never bought the premise that designers are decorators. He understood, going back to NeXT and Steve Jobs and Reid Hoffman and the Generosity Gap, that designing for humans is the same job as designing around their irrationality.

Giving isn’t a values problem, it’s a tooling problem.When it’s a tooling problem — it’s a design problem.

About Adam Nash

Adam Nash is the Co-Founder and CEO of Daffy, a donor-advised fund platform revolutionizing charitable giving. Rising to prominence in the 2010s as a product leader across Silicon Valley’s most influential technology companies, Nash became known for scaling platforms to hundreds of millions of users and pioneering new categories in fintech.

Previously, as Vice President of Product & Growth at Dropbox from 2018 to 2020, Nash led the teams responsible for growth, product strategy, product management, and product analytics for a platform serving over 600 million registered users with responsibility for approximately 90% of all company revenue in 2019. Before Dropbox, he served as President and CEO of Wealthfront from January 2014 to October 2016, where he championed the creation of automated investment services and grew the company’s client base by over 60x while scaling assets under management 45x from less than $100 million to over $4 billion.

His career highlights include serving as Vice President of Product Management at LinkedIn, where he led the company’s Platform & Mobile products including the launch of LinkedIn’s open developer platform and native applications. Nash founded LinkedIn Hackdays, a program instrumental in driving the company’s innovation culture, and led search, cloud efforts, and user experience design teams. Earlier in his career, he held strategic and technical roles at eBay and Apple.

As an angel investor since 2011, Nash has invested in over 150 seed-stage companies including Figma, Gusto, Opendoor, Firebase (acquired by Google), and Boom Supersonic. He has served as an Adjunct Lecturer at Stanford University since 2017, teaching CS 007: “Personal Finance for Engineers.” Nash holds BS and MS degrees in Computer Science from Stanford University and an MBA from Harvard Business School.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Pete Hunt is the Chief Executive Officer at Dagster Labs, the company behind the open‑source data orchestration platform Dagster and its commercial Dagster Cloud offering. Rising to prominence in the early 2010s, he became known as one of the early leaders of the React.js project inside Facebook and as a key engineering voice at Instagram during its hyper‑growth period. Today he is widely regarded as an influential figure at the intersection of data platforms, infrastructure, and developer experience, helping teams modernize how they build and operate data‑intensive systems.

Previously, as Head of Engineering and then CEO at Dagster Labs, Hunt helped guide the organization from its early identity as Elementl, founded in 2019, to a commercial data orchestration leader with the launch of Dagster Cloud and the introduction of Software‑Defined Assets in 2021. After joining the company in early 2022, he assumed the CEO role in November 2022 and has since focused on turning Dagster’s open‑source traction into a scalable business with a repeatable go‑to‑market motion. Under his leadership, Dagster Labs has grown into a well‑funded, small but highly specialized team shipping infrastructure that supports thousands of data assets across modern data stacks.

His career highlights include a formative stretch at Facebook beginning around 2011, where he was a founding member of the React.js team and helped drive its transformation from an internal experiment into one of the most widely adopted front‑end frameworks in the world. After the Instagram acquisition in 2012, Hunt became the first Facebook engineer embedded into Instagram, led the instagram.com web team, and built Instagram’s business analytics products as the company scaled to hundreds of millions of users. In 2014 he co‑founded abuse‑fighting startup Smyte, serving as CEO for roughly four years until its acquisition by Twitter in 2018, where he then worked on Trust & Safety and infrastructure during a period when the platform handled hundreds of millions of daily active users. Across these roles he has consistently operated at the point where new infrastructure—React, Instagram’s web stack, Smyte’s anti‑abuse systems, and now Dagster—becomes robust enough to support global‑scale products.

Outside his operating roles, Hunt has built a durable reputation as a conference speaker and educator, giving talks at events such as OSCON 2014 on how instagram.com works and sharing practical lessons on React, data platforms, and engineering leadership. Through long‑form interviews and podcasts, he documents the transition from individual engineer to founder and CEO, making him a widely referenced voice for engineers moving into executive roles.

Hey—Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

Yaron Schneider is the Founder and Chief Technology Officer at Diagrid, where he leads the development of distributed systems platforms that power durable workflows and AI agents for cloud-native teams worldwide. Rising to prominence in the late 2010s through his work on cloud infrastructure at Microsoft, he became known for co-creating the CNCF projects Dapr and KEDA, which today serve tens of thousands of organizations building microservices and event-driven applications. As Chair of the Workflows Working Group at the Agentic AI Foundation, he is widely regarded as an influential figure in defining how large-scale agentic systems are orchestrated and operated in production.

Previously, as Principal Software Engineer on Azure Container Apps at Microsoft, Schneider helped design and ship a serverless platform that enabled customers to run containerized microservices and event-driven workloads without managing Kubernetes directly, driving adoption across thousands of production clusters and multi-million-dollar cloud accounts. In earlier roles on the Azure CTO Incubations team, he focused on high-scale distributed systems and developer platforms, work that culminated in Dapr’s acceptance into the Cloud Native Computing Foundation in 2021 and its graduation to top-tier status in 2024, alongside Kubernetes and Prometheus. By 2025, the Dapr ecosystem was engaging over 40,000 companies across finance, healthcare, retail, and SaaS, and more than 90% of surveyed developers reported measurable time savings when building distributed applications with the runtime.

Schneider’s career highlights also include serving as Division CTO at ironSource from 2013 to 2015, where he led engineering for high-throughput advertising and monetization systems processing billions of events per day across mobile and desktop. Earlier, as a software architect at SuperDerivatives and a hands-on architect at Ness Technologies, he worked on low-latency, mission-critical platforms in financial technology and enterprise software, gaining the deep distributed-systems experience that later shaped his open-source work. Through Dapr, KEDA, and Diagrid’s Catalyst platform, Schneider’s contributions have helped standardize patterns such as workflow-as-code, event-driven autoscaling to and from zero, and durable agentic workflows across Kubernetes and multi-cloud environments.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Previously, as Chief Technology Officer at DOCKWORKS INC, he architected a web-based marine management platform that grew to serve more than 100 marine businesses in roughly 2 years before being acquired by DockMaster in 2023. In this role he led work order management, vessel tracking, and billing capabilities that helped streamline operations for small marine shops and boatyards while overseeing a full product and engineering organization. He also guided the post-acquisition integration, ensuring continuity for customers and enabling a combined product roadmap across two brands.

His career highlights include serving as Director of Software Engineering at LegalZoom, where he revamped the company’s Robotic Process Automation strategy, created excellence in document automation, and developed a company name-check algorithm that achieved approximately 98% state acceptance prediction accuracy for new business names. Earlier, as Co-Founder and CTO of Legalinc Corporate Services Inc., he helped grow the enterprise legal automation platform from zero to a successful exit to LegalZoom in about three years, building a one-of-a-kind legal filing API that secured partnerships with platforms such as Stripe Atlas, Yahoo Small Business, and Amazon. At IntelliCentrics, he managed DevOps for roughly 125 servers across three data centers, implemented auto-scaling and continuous delivery, and upheld a 99.9% uptime promise while training teams to independently extend automation.

As host of the Particle Accelerator podcast, he interviews technology and business leaders on strategic problem-solving, digital transformation, and leadership at scale. Through this work and frequent guest appearances on other shows, he continues to shape how founders, CEOs, and engineering leaders think about modern software development, DevOps, and AI-enabled growth.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Karl Simon is the Co-Founder and CTO of Subatomic AI, an enterprise AI Co-Worker Agent platform that deploys customizable agents adapted to client workflows, philosophies, and reasoning patterns. Rising to prominence in the 2010s as a data and engineering leader across retail, healthcare, and life sciences, Simon became known for building globally distributed data organizations and modernizing legacy platforms to support AI and machine learning at scale. Subatomic, co-founded with CEO Sam Sova and backed by a $7 million seed round in October 2025 led by Vantage Financial, focuses on high-stakes verticals including wealth management, legal, and manufacturing.

Previously, as a senior technology leader at Hudson’s Bay Company — the retail conglomerate that housed Saks Fifth Avenue, Lord & Taylor, Gilt.com, and other brands now consolidated under Saks Global — Simon led all engineering, business intelligence, and AI/ML functions across the company. Before that, he served in data engineering and analytics leadership roles at Komodo Health, Accenture, and Genentech, building AI-enabled decisioning platforms and modernizing source-to-target data pipelines across healthcare and life sciences.

Earlier in his career, Simon joined Oracle in manufacturing distribution, where he self-taught data warehousing from Ralph Kimball’s Data Warehouse Toolkit before applying those techniques to improve same-day order fulfillment insights. That formative experience established his approach to grounding AI systems in well-architected data foundations — a philosophy he has carried through more than three decades of digital transformations spanning mobile, big data, and generative AI.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

Subscribe to The Way of Product

PS — If you want to collaborate on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

“No one could ever take this over,” Jake says. “If he left or somebody else had to manage it, no one knows what’s going on here.”

Jake Stauch tells me a story about a CFO and an expense report, and it changes the way I think about no-code tools.

The CFO had a simple request for his IT team: when someone submits an expense report, get approval from an M5 manager or above, go up the chain, but if you reach the CEO you have gone too far -- drop down to the closest manager for review. One sentence. Clean logic. Makes perfect sense.

Then the IT leader pulled up Okta workflows to show Jake what he had built. “He has to scroll and scroll and scroll,” Jake tells me, “because there are hundreds of nodes and connectors and if-this-then-that and error handling.” Two months of work for a one-sentence business rule. The IT leader was proud of it. He should have been. It was technically impressive. But Jake saw something else entirely.

This is the dirty secret of every no-code workflow builder. They are supposed to make automation accessible to non-technical people, but the moment the logic gets even slightly complex, you end up with a sprawling visual spaghetti that is too technical for the business users who wanted a simple solution and too constrained for the engineers who could have written the code in a fraction of the time.

“It’s too technical for non-technical users,” Jake says. “It’s not technical enough for the folks that really want to get in the weeds.”

The worst of both worlds. I feel this in my bones. I spent two grand hiring someone to teach me how to wire together Airtable and Zapier for podcast production. The planning phase was the hardest part. You have to know what the tools can do before you can design the automation, and once you build it you are managing 20 interconnected flow charts that will break in ways nobody can debug.

I ask Jake what Serval does differently, and his answer is architectural, not cosmetic.

“Everyone who’s ever approached automation has started with this idea of a drag-and-drop workflow builder,” he says. “Every generation of these systems has basically said, okay, we’re gonna build a better workflow builder. They make the UI better, they make it easier to configure, but they fundamentally don’t change the structure.”

Serval changed the structure. Their insight: if AI can write code from a natural language description, then the code is the source of truth, not the blocks. And if the code is the source of truth, the visual layer -- the flowchart the user sees -- does not need to map one-to-one to the underlying logic.

“The block is not real,” Jake says. “It’s just a visual representation of what the code’s doing.”

I stop him. This is the line I keep coming back to. Every no-code tool in history has assumed that the visual representation is the logic. The blocks are not just a display layer -- they are the actual mechanism. Move a block, and you change the code. Add a connector, and you create a dependency. The visual and the logical are fused. That fusion is what creates the spaghetti.

Serval severed it. The AI writes concise, efficient code that handles all the branching, looping, null checks, and error handling that would stretch into hundreds of visual nodes in a legacy tool. Then Serval generates a clean visual summary that makes the workflow easy to follow -- but the visualization is an abstraction, not the system itself.

This is the equivalent of what happened with iOS design. I bring up the Jony Ive story -- how early iOS used skeuomorphic metaphors like green felt and Rolodexes to teach people what a touchscreen could do. Once users understood the paradigm, Ive stripped the metaphors away. The training wheels came off.

Jake’s customers went through the same transition. In the early days, they would see Serval’s interface and reach for what they knew. “You could see they almost missed the old way of doing it,” Jake says. “They’re like, well, what if I wanna click into that block and change the configurations?” And Jake had to say: there is no block. Just chat with the system. Tell it what you want changed.

“I think in the early days, that was an unfamiliar user action,” he tells me. But consumer AI moved the culture. Enterprise buyers go home and use ChatGPT. The expectation of a chat-based interaction went from unfamiliar to obvious in about a year.

The compression of build cycles is staggering. What used to take weeks or months now happens in a conversation. An IT team member describes an onboarding workflow. Serval writes the code. Generates a visual representation. The whole thing is live. If the business process changes -- and it will -- you just tell the system what to change. No scrolling through hundreds of nodes trying to find the right branch to modify.

I think about this in the context of Mike Tyson’s line: everyone has a plan until they get punched in the mouth. Every legacy automation is one business process change away from obsolescence. The two-month Okta workflow is already out of date by the time it ships because the CFO changed the approval threshold. With Serval, the CFO changes the requirement and someone on the IT team tells the system in plain language. Done.

Jake tells me that the really cool part is what happens next. The IT teams that start building with Serval become evangelists. HR wants in. Finance wants in. Legal wants in. IT transforms from ticket processors into what Jake calls an automation center of excellence.

“The block is not real” is not just a technical insight. It is a liberation. Twenty years of workflow tools built on the wrong assumption, and Jake Stauch had the nerve to throw it out.

About Jake Stauch

Jake Stauch is the Co-Founder and CEO of Serval, an AI-native platform that automates enterprise employee support through natural language-to-code workflow generation. Rising to prominence in the mid-2010s as a founder and product executive at the intersection of hardware and enterprise software, Stauch became known for identifying friction bottlenecks in IT automation and building infrastructure-first AI systems before the underlying technology fully matured. Serval, co-founded in April 2024 alongside CTO Alex McLeod, reached a billion-dollar valuation within 18 months of founding after raising $125 million across three rounds led by General Catalyst, Redpoint Ventures ($47M Series A), and Sequoia ($75M Series B).

Previously, as Director of Product at Verkada from 2019 to 2024, Stauch spent five years conducting customer discovery with enterprise IT departments across physical security hardware and software. There, he identified the automation paradox that would become Serval’s founding insight: despite a growing landscape of automation tools, most IT requests were still handled manually because the friction of building workflows exceeded the cost of doing the tasks by hand. His product work at Verkada spanned new product lines in physical security cameras, access control systems, and alarm hardware sold to Fortune 500 IT departments.

Earlier, Stauch founded NeuroPlus, a brain-sensing hardware and cognitive performance software company, which he led as CEO from 2012 to 2019. He was recognized on the Forbes 30 Under 30 list in 2017 for this work, which included a patent for an EEG-based neurofeedback system. He holds a degree from Duke University.

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Previously, as Author and Speaker at Radical Product Thinking starting in 2017, Dutt built a global practice around a five-part methodology spanning vision, strategy, prioritization, execution and measurement, and culture. Her work equips organizations to diagnose and cure “product diseases” such as feature bloat and metric-driven drift, enabling leaders to align teams around a clear, shared change they seek to bring about in the world. Through keynotes at conferences like Productized and client work with startups and large enterprises, she has trained thousands of product practitioners and executives on how to translate vision into a repeatable operating system for innovation.

Her career highlights include founding two companies that were successfully acquired, contributing to a total of five acquisitions across broadcast, media and entertainment, telecom, advertising technology, and robotics over more than 20 years in product. As an MIT-trained engineer with an S.B. and M.Eng. in Electrical Engineering and Computer Science from the Massachusetts Institute of Technology (1995–2000), she has applied product thinking to domains as varied as consumer apps, government services, and even wine, demonstrating the portability of her framework across sectors measured in billions of dollars of market value. She is widely regarded as an influential figure in the product management community for shifting organizations away from purely metric- and OKR-driven roadmaps toward what she calls “vision-driven transformation.”

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Discover the root cause analysis methods and narrative-driven measurement that prevent feature factories while maintaining innovation velocity.

“It’s b******t statements, right, that are slim on the details.”

Radhika Dutt doesn’t hedge when describing most product visions. Twenty-five years after founding her first startup at MIT with a vision to “revolutionize wireless,” she can admit what most product leaders won’t: she has no idea what that meant. The company had five co-founders, dorm room origins, and all the trappings of a Silicon Valley success story. What it didn’t have was clarity about the problem they were solving.

“I don’t even know what we meant by that,” she says, and something shifts in her tone. The polished product consultant gives way to someone examining an old wound. “But it was this idea of just being big, scaling. Now, you know, even today when you look at so many Silicon Valley startups, that’s sort of the mistake you often see, right?”

She calls these mistakes product diseases. Not problems or challenges—diseases. The language is deliberate. Diseases are things you catch without realizing it, things that spread through organizations, things that require diagnosis and systematic treatment rather than quick fixes.

The disease at that first startup was hero syndrome: the obsession with scale and growth without understanding what problem needs solving. But Radhika discovered something worse during her subsequent career across five acquisitions. Most product teams suffer from multiple diseases simultaneously, creating what she now recognizes as an epidemic of confused priorities and wasted effort.

“And I call them product diseases because it’s just so ubiquitous and we need to talk openly about these product diseases. ‘Cause you know, it’s just so easy to catch.”

The solution she developed—radical product thinking—starts with a fill-in-the-blanks approach to vision setting that forces teams to confront what they’re actually trying to accomplish. Not the aspirational version, not the pitch deck version, but the detailed, actionable version that can guide daily decisions.

“So today, when amateur wine drinkers want to find wines that they’re likely to like and to learn about wine along the way, they have to find attractive looking wine labels or find wines that are on sale. This is unacceptable because it leads to so many disappointments and it’s really hard to learn about wine in this way. We are bringing about a world where finding wines you like is as easy as finding movies you like on Netflix. We are bringing about this world through a recommendations algorithm that matches wines to your taste and an operational setup that delivers these wines to your door.”

She pauses after reciting this vision for her wine startup, which she founded in 2011 and sold in 2014. “Now this is a radical vision because I hadn’t told you anything about my startup, and yet hopefully when I shared this vision, you knew exactly what we were doing and why we were doing it.”

The contrast with “revolutionize wireless” is stark. One vision contains a specific customer segment, their current painful experience, why that experience is unacceptable, the desired future state, and the concrete mechanism for achieving it. The other contains marketing language that could apply to any telecommunications company.

But even teams that develop clear visions struggle with what Radhika calls the second product disease: hyperemia. The obsession with moving numbers up and to the right, regardless of whether those numbers drive long-term value.

“You know, the moment I say this, people are usually like, oh yeah, I get it. We have it. Hyperemia is this obsession with moving numbers up and to the right. Having all sorts of wonderful dashboards that all look green. But those are not even necessarily the right metrics. And sometimes they may even be the right metrics, but they drive you in the wrong direction.”

The dating app industry provides her favorite example of hyperemia in action. When Tinder launched swipe left/swipe right in 2013, user engagement metrics exploded. Every other dating app copied the mechanic because the numbers looked incredible. User engagement up, time on app up, all the key performance indicators trending toward success.

“So, you know, everyone was thrilled with these metrics, but what was happening if you looked at the longer term effect? The more they gamified intimacy, it was creating a toxic dating environment, the more it was dehumanizing interactions. And so what it created in the long term was user fatigue.”

The result: dating app backlash, mass user deletions, and in 2025, Bumble laying off 30% of its staff. The entire industry fell into a slump because short-term metric optimization destroyed the long-term value proposition. The numbers looked great right up until they didn’t.

“So my point is, hyperemia is one of these diseases where you can do fantastic and making numbers look great. And genuinely they may be the right numbers, but that’s not necessarily good for your product or good for your business in the long term.”

This is where most conversations about metrics and OKRs devolve into tactical debates about choosing better numbers or preventing gaming. Radhika thinks those discussions miss the fundamental issue: goals and targets create perverse incentives regardless of how carefully they’re designed.

“Even when someone doesn’t have malicious intent and they’re not trying to game metrics, the subconscious incentive you have is to show you’re a high performer and therefore focus on the numbers that look good, that show OKRs to be green, as opposed to focus on numbers that, you know, OKRs aren’t even measuring, but that are indicating a problem and that say, hey, there’s something off here.”

She illustrates with her experience at Avid, the company behind video editing software used for every Oscar-winning film in Hollywood. The numbers looked fantastic—sales targets consistently hit or exceeded. But underneath the green dashboards, a different story was unfolding.

“If you just looked under the hood, you would see a different scenario. The way we were hitting our sales targets was by moving further and further into the high end because our low end was being eroded by Apple and Adobe.”

The company was achieving its goals by retreating upmarket as competitors commoditized the lower tiers. The sales numbers stayed strong, but the strategic position was deteriorating. Instead of asking why the low end was being eroded or how Apple and Adobe’s business models differed, leadership focused on maintaining the metrics that made them look successful.

“The incentive is I wanna show that I’ve hit those goals and targets things are working. I wanna prove that our, that things are going well.”

This dynamic—prioritizing the appearance of success over understanding reality—is what legendary Intel CEO Andy Grove meant when he said leaders are the last to know. When you set goals and targets, everyone wants to tell you the good news. Bad news gets buried because it threatens the narrative of progress.

The alternative Radhika proposes isn’t better goal-setting. It’s puzzle-setting. Instead of declaring what numbers teams should hit, leaders should define what problems need solving and create frameworks for teams to investigate those problems systematically.

“So what I am working on in this next book. And what I advocate for is a mindset shift instead of goals and targets. It’s a mindset of puzzle setting and puzzle solving. And then the way you measure people is how well are they solving this puzzle? Are we making progress towards solving this puzzle?”

Her framework for puzzle-setting uses three O’s: Observation, Open Questions, and Objective. The observation captures what’s actually happening, not just what the metrics show. The open questions identify what the team doesn’t understand about the observation. The objective summarizes the puzzle that needs solving.

For Avid, the observation would have been: “Our low end is getting eroded by Apple and Adobe in the mid-tier. This is what’s happening. The market is getting eroded. The way we’re making the numbers is by going further into the high end.”

The open questions would probe deeper: “What is happening on the low end? Adobe and Apple are successful there. What is their business model? Can we fight this business model in a different way? Is there something we can offer that can be a complete workflow for the low end where even if Apple and Adobe are giving away the editor, people will want it and want to pay for it?”

The objective becomes: “Figure out what do we do in our video editing business. Do we invest in it, do we not, or how do we invest in it, so that we can continue to either be successful in the video editing business, or we choose to move on and adapt our business?”

This is puzzle-setting. It creates space for teams to investigate reality rather than optimize metrics. But puzzle-setting only works if teams have the skills and safety to solve puzzles effectively.

That’s where puzzle-solving comes in: three questions that teams answer as they work on the puzzle. How well did it work? What did we learn? What will we try next?

“Notice how this question, it’s not binary, did you or didn’t you hit this target? It’s not just putting you on the spot, making you feel like I have to prove something. It’s genuinely inviting the good and the bad. This is how as a leader, you’re not the last to know you’re inviting the good and the bad.”

The second question—what did we learn—requires narrative synthesis, not just dashboard reporting. Teams have to look at all their data and tell the story of what’s really happening with users, markets, and competitors.

The third question—what will we try next—forces strategic thinking based on actual learning rather than predetermined roadmaps.

“I can really tell based on working with a team who is thinking deeply and how well they’re solving the puzzle based on their answers to what have we learned and what will we try next? That’s how you can evaluate people, not just based on ta-da, I’ve hit my numbers.”

The transformation this creates in team dynamics is profound. Instead of competing to show green dashboards, team members compete to solve interesting problems. Instead of hiding bad news, they compete to surface the most important insights. Instead of gaming metrics, they compete to design better experiments.

But this approach requires a level of psychological safety that’s rare in most organizations. Teams have to be willing to admit what’s not working, leaders have to be willing to hear it, and everyone has to be willing to change direction based on what they learn.

“Did you know that he didn’t keep a corner office? He used to have a cubicle, same size cubicle as everyone else because he wanted everyone to challenge his ideas and to feel like they could speak up. Very few leaders want people to speak up and tell them this is not working.”

The Andy Grove reference isn’t accidental. Grove understood that organizational hierarchy creates information distortion. The further you are from the work, the more filtered your information becomes. Physical proximity—sharing the same kind of workspace as everyone else—was one way to counteract that distortion.

Most leaders won’t give up their corner offices. But they can start role-modeling the kind of reflection and transparency they want from their teams. Taking time in meetings to discuss what didn’t work in past initiatives. Sharing their own learning and uncertainty. Creating space for teams to investigate puzzles rather than just hit targets.

“You can role model for your team, the psychological safety and sharing the good and the bad of what didn’t work, what you learned from it, what you’re going to try next. You can role model this so that you can invite the team to solve puzzles like you are.”

For individual contributors stuck in goal-driven organizations, Radhika recommends starting small. Take a past feature release and work through the three puzzle-solving questions privately. Look at the data, but focus on the narrative: what really happened with users? What did the numbers mean in context? What would you try differently next time?

Once you’ve practiced this approach yourself, try it in one-on-ones with your manager or conversations with peers. Create small bubbles of psychological safety where honest reflection and learning can happen.

“Instead of just chasing OKRs, you’re working on puzzles. Puzzles are so much more fun. We are all energized by puzzles. Instead of just focusing on OKRs, think about what puzzles you’re solving for the company. That in itself will energize you for your work.”

The energy difference is real. Goals feel imposed—something you have to hit to prove your worth. Puzzles feel intrinsic—something you want to solve because the solution creates value. The shift from external validation to internal motivation changes how people approach their work.

But the business results matter too. Radhika’s recent consulting engagement provides a concrete example. A company stuck with stalled sales in 2023 doubled sales in 2024, then doubled again in 2025 after switching from goal-setting to puzzle-solving. Customer churn dropped from 26% to 4%.

“We did all of that by puzzle setting and puzzle solving instead of being driven by OKRs.”

The transformation didn’t happen overnight. It required leaders willing to let go of familiar frameworks, teams willing to embrace uncertainty, and everyone willing to prioritize learning over looking good.

The alternative—continuing with product diseases like hero syndrome and hyperemia—leads to the dating app outcome. Short-term metrics that mask long-term erosion. Features that optimize for engagement instead of value. Teams that hit their numbers while slowly destroying what they’re trying to build.

“Or are we all doomed to just constantly learning from these failures, making mistakes and having to learn the hard way?”

That was the question that drove Radhika to develop radical product thinking in the first place. After watching team after team catch the same diseases, make the same mistakes, and suffer the same consequences, she wanted to understand whether systematic approaches could prevent predictable problems.

The answer is yes, but only if teams are willing to diagnose their diseases honestly and treat them systematically. Most organizations prefer to treat symptoms—choosing better metrics, writing clearer requirements, running more experiments—rather than address root causes.

The root cause is the gap between great ideas and great products. Steve Jobs called it out in his lost interview: most people think the idea is 90% of the work when it’s actually 5%. The other 95% is the systematic translation of vision into strategy, strategy into priorities, and priorities into daily activities.

“And I think filling that gap is exactly what I talk about in terms of systematically translating a vision for change into action, into everyday activities. And that’s how we close that gap.”

Product diseases spread when teams try to shortcut that translation process. Hero syndrome emerges when teams skip from big vision to scaling without defining the problem. Hyperemia emerges when teams skip from activities to metrics without understanding the connection to long-term value.

The systematic approach isn’t glamorous. It requires detailed problem statements, clear frameworks, consistent reflection, and honest measurement. It requires admitting when things aren’t working and changing direction based on learning rather than predetermined plans.

But it’s the difference between revolutionary wireless and amateur wine drinkers who can’t find wines they like. One vision launches a company that doesn’t know what it’s doing. The other launches a company that gets acquired because it solves a real problem in a specific way.

“Now this is a radical vision because I hadn’t told you anything about my startup, and yet hopefully when I shared this vision, you knew exactly what we were doing and why we were doing it.”

That clarity—knowing exactly what you’re doing and why—is what prevents product diseases from taking hold. It’s what enables teams to choose long-term value over short-term metrics. It’s what transforms abstract strategies into concrete progress.

The vision template is just the beginning. The systematic framework for translating vision into action is what makes the vision matter. And the puzzle-solving approach is what keeps teams connected to reality as they execute against the vision.

Twenty-five years after revolutionizing wireless, Radhika has learned to revolutionize something more specific: how product teams think about the problems they’re trying to solve. Not with better tools or processes, but with better questions and frameworks for finding answers.

The questions aren’t complicated. What problem are we solving? Why does it need to be solved? How will we solve it? How well is our solution working? What are we learning? What will we try next?

The complexity comes from creating organizational conditions where teams can ask those questions honestly and act on the answers systematically. Where puzzle-solving is rewarded over performance theater. Where learning from failure is valued more than hitting arbitrary targets.

“Puzzles are so much more fun. We are all energized by puzzles.”

That energy—the intrinsic motivation to solve interesting problems—might be the strongest antidote to product diseases. When teams are genuinely curious about the puzzles they’re solving, they’re less likely to settle for b******t statements that are slim on details. They’re more likely to demand the clarity that prevents revolutionary wireless from becoming just another failed startup story.

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Previously, as Head of Search Products at OpenSea, Saurabh led a multi-product portfolio spanning search, discovery, trust and safety, and core web and mobile platforms during the 2022–2023 NFT market cycle. He became known for steering product strategy in a period when OpenSea supported millions of users and billions of dollars in NFT trading volume annually, focusing on safe discovery and high-intent search in a volatile, web3-native marketplace. His leadership aligned search quality, fraud prevention, and creator-centric experiences in an ecosystem that operated 24/7 across global markets.

His career highlights include an 11-year tenure as a Group Product Manager at Google, where he led teams of more than 12 product managers and 100 engineers building AI-powered experiences in Google Assistant, Search, Maps integrations, identity, and monetization from 2011 to 2022. At Google, he helped ship and scale products such as Google Assistant’s AI search integrations, Family Link and Google Accounts for kids, Google+, and Gmail, each serving hundreds of millions of monthly active users and operating across more than 100 countries. Earlier, as an Advisory Software Engineer at IBM from 2005 to 2010, he developed core AIX UNIX kernel infrastructure for virtual memory, including Active Memory Expansion and Large Segment Aliasing, contributing to enterprise systems that powered thousands of high-availability servers worldwide. He pairs this low-level systems background with an applied AI product lens shaped by dual BS and MS degrees in Electrical and Computer Engineering from Carnegie Mellon University.

In addition to his operating roles, Saurabh has invested in and supported early-stage voice and AI startups through Google Assistant’s strategic investment programs, including seed and Series A bets in companies such as Instreamatic, Voiceflow, and Slang Labs. As a member of the Skip Community, he collaborates with a network of current and former heads of product who collectively bring hundreds of years of leadership experience across AI, fintech, cybersecurity, e-commerce, and renewable energy, shaping best practices for how modern product organizations are structured and scaled.

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Learn how a CPO at a billion-dollar AI company is rethinking what “good” looks like for PMs — prioritizing strategic thinking over feature-building as software commoditizes.

“You gotta be laser sharp about where you can really add value versus what’s being rapidly commoditized.”

Saurabh Sharma, CPO at You.com, doesn’t deliver this line as career advice. It’s operational reality. When AI can generate user research insights in minutes and prototype features faster than most teams can write specifications, the entire foundation of product management value shifts. The skills that made someone a great PM five years ago might make them unemployable five years from now.

“Where is there a compounding advantage? Where is there a value creation that will be hard to commoditize?” he continues, and I can see him working through the implications for his own hiring decisions. “And that’s a lot of what I think about at the company. That’s a lot of what I try to help my team think about as well.”

This isn’t abstract strategy. It’s survival math. You.com processes over a billion web search API queries per month for companies including DuckDuckGo, Windsurf, and Harvey. They raised $100 million at a $1.5 billion valuation. At that scale, every hiring decision carries weight. Every capability they build internally has to justify itself against what they could buy or automate.

The question Saurabh faces daily: when AI can handle most IC work, what human skills become more valuable rather than less?

“I think what’s really changed is you gotta be laser sharp about where you can really add value versus what’s being rapidly commoditized,” he explains. “And so I think what we’ve seen at You.com is that there’s a continuous focus on where is the value really being created versus where will the value be rapidly commoditized.”

The math is brutal but clarifying. If anyone can build a basic SaaS product with AI assistance, then building basic SaaS products isn’t a differentiating capability. If anyone can synthesize user research or analyze competitor data with AI tools, then those skills command lower wages and less organizational influence.

But here’s what Saurabh has observed: some capabilities become more valuable as their supporting infrastructure gets commoditized. Strategic judgment becomes more important when you can test more strategies. Pattern recognition becomes more critical when you have more data to parse. The ability to choose which problems are worth solving becomes essential when solving problems gets easier.

“And I think it does change how you hire, in that you want people that are able to think that strategic line more so than, well, here’s this cool feature I wanna build.”

The hiring implications ripple through every product organization. The PM who excels at writing detailed PRDs and coordinating feature launches might struggle in an environment where PRD writing is automated and feature quality is determined by rapid iteration rather than upfront specification.

But the PM who can identify which customer problems create sustainable advantage, who can spot market opportunities before competitors, who can build conviction around directions that don’t yet have validation—those skills compound as the tactical work gets easier.

“Well, the cool feature—the customer might be able to replicate it themselves in a way that’s even more fit for them,” Saurabh continues. “It’s more about where is there a compounding advantage? Where is there a value creation that will be hard to commoditize?”

I push him on this. How do you interview for strategic thinking? How do you distinguish between someone who talks strategically and someone who thinks strategically? Most product candidates can articulate frameworks and principles. Fewer can demonstrate judgment under uncertainty.

“I think that taking that more strategic approach, what separates a middle manager from an executive,” he responds, drawing a connection I didn’t expect. “Nobody told me that I should spend more time with the sales team. But what I noted was, first of all, sales likes having product on road trips with them. It helps customer conversations. But the other part of it was it helps me. It helps me build my worldview. What my roadmap should be.”

The example crystallizes the difference. Strategic thinking isn’t about having better frameworks or more elegant presentations. It’s about making connections that aren’t obvious, taking actions that aren’t prescribed, developing conviction through firsthand exploration rather than secondhand analysis.

When Saurabh decided to spend more time on sales calls, he wasn’t following a playbook. He was following a hunch about where his learning edge was. That hunch—and the willingness to act on it—represents the kind of judgment that becomes more valuable as tactical execution gets automated.

But this creates new tensions in how product teams operate. When strategic judgment becomes the scarce resource, how do you structure teams to maximize it? How do you delegate the increasing scope of work that AI can handle without losing touch with the details that inform strategy?

“None of us are gonna be ICs anymore,” Saurabh says, quoting You.com CEO Richard Socher. “We are all gonna be managers in the future. Some of us will continue to manage people, but your traditional IC will now be managing a fleet of agents that’s doing a lot of work for them.”

The transition from IC to manager isn’t just about career advancement. It’s about cognitive load distribution. When AI can handle research, analysis, and initial synthesis, human intelligence gets freed up for higher-order work: choosing which questions to ask, interpreting ambiguous signals, making bets on uncertain outcomes.

But managing AI agents requires different skills than managing humans. Humans can fill in context, interpret vague instructions, escalate when they’re confused. AI agents do exactly what you ask them to do, which means the quality of your instructions determines the quality of their output.

“Many of the emails I write, I will pass through AI to help me with tone or help me think about the way I want to get to a particular objective in a given customer situation,” he explains, describing his own evolution. “That is essentially an example of offloading something that we all know how to do. I could write that perfect email to a customer to diffuse a complex situation, but it might take me an hour to really think through it and get it right. What I found is that email is now five minutes away working with AI.”

The email example is tactical, but the implications are strategic. When routine communication becomes effortless, you can maintain relationships at scale that were previously impossible. When difficult conversations can be crafted quickly, you can engage in more of them. The scope of what one person can manage expands dramatically.

This expansion creates competitive advantage for individuals and organizations that adapt quickly. But it also creates new forms of inequality. People who learn to manage AI agents effectively can take on exponentially more responsibility. People who don’t learn these skills find their scope of influence shrinking as AI-augmented colleagues outpace them.

“Some people will use the time that they get back with AI to just do more of what they already know, and that’s gonna be fine,” Saurabh observes. “But you’re gonna have other people that are able to—I sometimes think about Maslow’s hierarchy. Some people that are able to, okay, great, I got shelter and food under control. Now I can go to self-actualization.”

The Maslow reference isn’t casual. It’s how he thinks about organizational development in an AI-augmented world. Some people will use AI to get better at their current job. Others will use AI to access entirely different kinds of work. The first group maintains their position. The second group expands their influence.

But this creates new challenges for team composition. How do you balance strategic thinkers who can direct AI agents effectively with craftspeople who can execute at high quality? How do you maintain institutional knowledge when so much tactical work gets delegated to machines?

“There are exceptional middle managers that that’s what they love to do. That’s what they’re good at, and that is great,” Saurabh says when I ask about the career implications. “And then there are exceptional middle managers that graduate naturally to be exceptional executives. And that is good as well.”

The key insight: both paths remain valuable, but the skills required for each path are changing. Middle managers will increasingly manage hybrid teams of humans and AI agents. They’ll need to be excellent at coordination, quality control, and tactical execution within defined boundaries. Executives will set those boundaries, choose which problems deserve attention, and build conviction around uncertain directions.

But the boundary between these roles is becoming more porous. When AI handles routine analysis, middle managers can engage in more strategic work. When strategic insights can be tested rapidly, executives can stay closer to tactical details. The rigid hierarchies built around information scarcity start to flatten when information becomes abundant.

“Where is that compounding advantage that creates value for the customer and also creates potentially a competitive moat for us as well,” Saurabh concludes, returning to the core question.

The answer, increasingly, isn’t in what you can build. It’s in what you choose to build and why. The technical capability to create software is becoming commoditized. The judgment to create the right software at the right time for the right customers remains scarce.

Companies that hire for execution speed will compete on efficiency. Companies that hire for strategic judgment will compete on alpha. Both approaches can succeed, but they require different organizational designs and different definitions of performance.

The retailers who miss the next pickleball trend won’t be the ones with outdated technology stacks. They’ll be the ones who couldn’t distinguish between signals worth pursuing and noise worth ignoring. Who couldn’t move fast enough from insight to action. Who optimized for doing more of the same instead of doing something different.

“I think what we’ve seen at You.com is that there’s a continuous focus on where is the value really being created versus where will the value be rapidly commoditized.”

As AI makes more capabilities available to everyone, the companies that thrive will be the ones that focus obsessively on the capabilities that can’t be commoditized. Not because they’re technically difficult, but because they require the kind of human judgment that compounds over time rather than getting automated away.

The question for every product organization: are you hiring people who can do the work, or people who can choose the work? The first skill set has a shrinking shelf life. The second becomes more valuable every sprint.

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Previously, as a senior product leader at Meta, eBay, Target, and McDonald’s, she owned global initiatives that drove measurable business outcomes across eCommerce, food delivery, and retail. At McDonald’s she helped lead the global rollout of mobile ordering to thousands of stores, transforming how customers interacted with a brand serving more than 60 million people per day. At Taelor, her team has raised approximately $2.3 million in pre-seed funding, achieved over 10 million marketing impressions with zero ad budget, and earned recognition such as Inc.’s 2025 Best in Business – Best Startup category and Webby Award honors.

Her career highlights include award‑winning marketing campaigns at Sears and Kmart, scaling cross‑border digital commerce at eBay, and driving omnichannel experiences at Target that combined stores, mobile, and online into a unified customer journey. As founder of Taelor, she has built an AI-driven styling engine that mixes acquired competitor data, human stylists, and feedback loops from thousands of garment rentals to improve recommendations and reduce fashion waste. Along the way she has been named to Girls in Tech’s “40 Under 40,” delivered a TEDx talk on perseverance, and built a following of more than 28,000 professionals who track her work across AI, circular fashion, and consumer technology.

As a book author, startup advisor, and frequent podcast guest, Cheng documents the path from Taiwan to Silicon Valley and distills lessons on resilience, go‑to‑market execution, and human‑centered AI. As a teacher at Northwestern University and a sought‑after speaker at industry events like NRF and SF Tech Week, she helps the next generation of founders and operators understand how to turn data, storytelling, and product intuition into enduring companies.

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The framework Meta uses in PM interviews to separate great product thinkers from idea generators.

“Nobody used the feature besides a product manager,” Anya Cheng tells me. “Why?”

She’s describing a project from her time at Target. The team wanted to build store GPS—beacon-powered navigation so customers would never forget an item on their list. They spent six months and millions of dollars mapping every item location in stores with different layouts and footprints. They geo-fenced the shelves. They built the feature. They launched it.

“Come on,” she says. “Mom is going to a Target store to get lost. They want to go to a store wandering around and buy stuff.”

The Target moms didn’t need efficiency. They needed escape. The Starbucks inside is the feature. The cup holders on the cart are the feature. The permission to wander for an hour away from noisy kids is the feature. The team had solved the wrong problem perfectly.

Anya Cheng is the founder and CEO of Taelor, an AI-powered menswear rental subscription. Before founding Taelor she was Head of Product at Meta for Facebook and Instagram Shopping, Head of Product at eBay for Latin America and Africa, led mobile and tablet e-commerce at Target, and was Senior Director at McDonald’s launching their global food delivery apps. She teaches product management at Northwestern and has won 20-plus industry awards. The Target GPS story is one she uses to teach the most important lesson she knows: the quality of your execution is irrelevant if you’re solving the wrong problem.

“If you are taking away the value prop,” she says, “then your product is just not going to be popular.”

Target’s value proposition isn’t convenience. It’s discovery. It’s the opposite of a GPS. The beacon team understood the technology. They understood the implementation challenge. They just didn’t understand why moms go to Target.

I ask Anya how she avoids the same trap. How she decides what to build and—more importantly—what not to build. Her answer is a framework she’s used at Meta, eBay, McDonald’s, and now Taelor.

It starts with the Facebook PM interview question: if you’re the product manager of X, what feature would you launch? She’s been on both sides of this question hundreds of times. The candidates who fail are the ones who answer it.

“Two types of person,” she says. “One type will be out of the interview loop right away. The other will at least get to the second level.”

The first type jumps to solutions. I’d build this, I’d build that. Ideas are cheap. ChatGPT can come up with ideas. That’s not the job.

The second type starts with personas. She gives me the birthday product example. Three personas: the birthday person who wants to be surprised, the close friends who want to organize and are afraid of forgetting, and the acquaintances who just want to say happy birthday. Each has distinct pain points. Each pain point sits on a spectrum of severity, frequency, and relevance to Facebook’s unique position.

“Then you come up with selecting criteria,” Anya says. “Which pain point is more painful? Which pain point has more people with that pain point? Which pain point is Facebook more relevant to solving versus other people?”

The criteria filter the problem space before you ever touch solutions. Then when you do generate solutions, you filter again: which solution solves the problem best, which takes fewer engineering hours, which fits the direction of the business?

“Up to here,” she says, “I haven’t told you anything about the solution.”

She brings up the same framework when she tells me about Google Shopping versus Facebook Shopping. Same goal: sell things online. Completely different products. Google’s mission is organizing the world’s information, so Google Shopping became price comparison. Meta’s mission is bringing the world closer together, so Facebook Shopping became community commerce—friends selling bicycles from their backyard, influencers sharing product recommendations.

“Exactly the same goal,” she says. “But totally different product because it’s different mission of the company.”

The mission is the highest-level selection criterion. It determines which problems are yours to solve and which aren’t. The Target beacon team forgot this. They selected a problem—moms forgetting items—that was real but irrelevant to why people went to Target in the first place.

Anya’s own origin story follows the framework precisely. At Meta, she was dealing with imposter syndrome—a Taiwanese immigrant surrounded by Ivy League engineers. She needed to look good. She tried Stitch Fix (had to buy everything), Rent the Runway (had to browse 100,000 garments). She realized fashion companies designed for fashion lovers, not for people who wanted to get ready and get on with their day.

So she did product 101. Interviewed people. Found that her real persona wasn’t women like her—it was busy men. Sales guys, consultants, pastors, executives. People who didn’t care about fashion but cared deeply about the outcomes fashion enabled: getting a job, closing a deal, landing a date.

The MVP was a Shopify landing page with a stock photo of blue shorts. A realtor from San Diego put his email in, waited two months, found Anya on LinkedIn, and called her. They bought clothes from Macy’s during a Christmas sale and shipped from the post office.

“Became our first customer,” she says. “The MVP still worked.”

It worked because the hypothesis was right. The problem was real. The selection criteria—not the solution—validated the business. Everything that followed—the 150 brand partnerships, the AI-augmented styling, the circular fashion model—was built on the foundation of understanding what the customer actually needed.

She tells me about another failed product: eBay’s AI-powered listing tool. Snap a photo of a bicycle, AI writes the description. Built it. Shipped it. Nobody used it. Small sellers on eBay have sentimental attachment to their items. They want to write their own descriptions. Efficiency wasn’t the pain point. Pride was.

“If you don’t deeply understand the customer persona, the insider psychology, the job to be done,” she says, “it’s just very hard to build a great product.”

I bring up vibe coding—the trend of PMs building functional prototypes with AI tools on weekends. Her intern did exactly this: came back with three working features built in a weekend. Her response was blunt.

“This is how exactly at Meta we don’t hire people.”

The features might have been good. But they were selected by enthusiasm, not criteria. The intern skipped the framework—the personas, the pain points, the filtering—and went straight to building. AI made it possible to skip the hard work. And skipping the hard work is exactly the failure mode that produces Target store GPS.

“In the old time,” Anya says, “you have three ideas and you have to go convince your engineer and designer. And they will challenge your logic. But now you can skip all of this.”

The challenge was the quality filter. Removing it doesn’t make you faster. It makes you wrong more efficiently.

I ask Anya what she wants product leaders to take away from all of this. She doesn’t hesitate.

“We are all problem solvers,” she says. “Go to the meeting. Forget that you are a designer, forget that you are PM, and really focus on thinking about what problem can be solved.”

The solutions will come. They always do. The hard part—the part that separates a Target beacon from a Taelor, a failed eBay listing tool from a 10-million-impression marketing flywheel—is choosing the right problem in the first place. Not the coolest one. Not the most technically interesting one. The one that actually matters to the person on the other end.

Selection criteria over ideas. Every time.

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Previously, as Co-founder and Chief Product Officer at Arist, Anderson helped expand the company’s initial seed funding to $3.9 million in 2021 and later raise a $12 million Series A round to fuel rapid enterprise adoption. Her work turned an early Y Combinator-backed idea into a venture serving over 20 Fortune 500 organizations, with pricing starting around $1,000 per month for enterprise deployments. She became known for shipping AI-powered tools such as Creator and the Enablement Agent, which process thousands of complex documents, translate into 100+ languages, and generate ready-to-deliver programs in under eight minutes while proving impact through end-to-end analytics.

Her career highlights include co-founding Project W, a student-led organization launched in 2021 to foster interdisciplinary collaboration among women innovators and entrepreneurs across the Babson, Olin, and Wellesley (BOW) colleges, which built an online community of more than 300 members and incubated Project Pods for high-level ventures. As a founding member of College Ventures Network and VP of Marketing at eTower, Babson’s premier entrepreneurial living community whose alumni companies have generated more than $3 billion in combined valuations and over $50 million in funding, she honed a model for building tight-knit entrepreneurial ecosystems. Graduating magna cum laude from Babson College in 2022 with a focus on entrepreneurship, she combined academic honors with hands-on leadership roles that emphasized measurable impact and community scale.

Outside of her primary operating role, Anderson serves as a Board Member at Delphian School, bringing startup execution and product thinking back into the education system where she was once Student Council President and a three-time state champion cheerleading captain. Through ongoing advisory work and public writing on enablement, AI agents, and performance diagnostics, she has become an influential figure for operators building the next generation of enterprise learning and HR technology.

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How Arist navigated seven years of positioning iteration in an undefined category and why shared conviction about the game you’re playing gives product the agency to say no.

“We are a new category without ever having created or yet created a category, which is hard to sell,” Maxine Anderson says. There’s no frustration in it. Just the accumulated weight of seven years spent explaining something that doesn’t have a name.

Maxine is the co-founder and CPO of Arist, a platform that delivers employee training through Microsoft Teams, SMS, and WhatsApp instead of video-based learning management systems. She started the company at Babson College with two co-founders after they each independently discovered that text-based communication drove behavior change in ways traditional mediums couldn’t.

The student in Yemen who could only learn via text. The public speaking coach who sent WhatsApp reminders before talks. Maxine’s own financial literacy programs on Native American reservations where classroom formats failed completely. The insight was simple. The seven years that followed were not.

I ask her about positioning, and the answer is a catalog of pivots. They started as a consumer marketplace—Masterclass over text, basically. Learn from professors at Harvard via your phone. “That model was just really hard to distribute,” she says. “Marketplaces are just really difficult, to be honest. Not really good for a medium that people didn’t already believe in.”

A former chief learning officer told them about the billions spent on corporate training that drove zero results. They pivoted to corporate learning. Spent two years selling to HR. Got traction—then the market shifted. Enterprise budgets contracted in 2021 and 2022, and HR was the first department cut.

“It was kind of a forcing function for us to find a better buyer,” Maxine says.

They started selling to operational leaders. Sales directors. Frontline manufacturing managers. People whose bonuses depended on whether their teams improved. The product hadn’t changed much. The positioning had changed completely.

I tell Maxine this is the part of product strategy that I think most product leaders miss. It isn’t about filling up a backlog and deciding which features will close deals. It’s figuring out what game you’re playing. There’s a great piece—I think it’s an a16z blog—about how the market is the most important thing. You can change your positioning and your target segment and sales go up. You don’t have to add more features.

“Yeah,” she says. “We’ve had to iterate on our positioning a lot.”

She describes what it’s like to sell without a category. Not just positioning on a macro level—telling the market a new way of thinking about employee enablement—but positioning per account. Every conversation is a custom pitch. Every buyer needs to understand something that doesn’t map to any existing line item in their budget.

“For a while it was hard to lead product,” she admits. “We’re selling all these different use cases yet we don’t want to productize those pathways. We’re not a sales enablement tool. We’re not trying to compete with HighSpot directly. We’re really good for this part of sales enablement, this problem that’s not solved.”

I bring up Figma as a parallel. How long it took for Figma to convince designers to switch from their existing tools. How category change requires not just a better product but a change in default behavior.

“It did take a long time for Figma to get traction,” she agrees. “They had to change people from their default behavior of going to other tools as a solution.”

The conversation moves to roadmap, and Maxine lights up. “There’s this quote that I love,” she says. “Plans are useless, but planning is useful. And I feel like that’s really true in a startup.”

She describes the trap she sees product managers fall into: optimizing for delivery. Presenting a roadmap, hitting dates, feeling the satisfaction of shipping what you said you’d ship. She says the feeling of executing on a plan is seductive—and often wrong.

“A roadmap often becomes a ton of things people ask for instead of what you’re trying to build towards over time,” she says. “Some of our best features have been where it doesn’t feel good. We shipped this a little too early, or we shipped this to see if we could market it. Or we marketed this five months early and built it in a funny way.”

This is the part where most product conversations would veer into framework territory. Maxine stays concrete. She describes how she segments her roadmap into three buckets: what they’re working towards building, what they’re trying to build to convince people, and what they’re building because it’s literally blocking adoption at scale.

“Those are the customer requests I take,” she says. “Literally, we would have five times volume if we shipped this feature. Not—oh, I would really love it if you could add this to a course.”

She confesses they fell into the feature parity trap early. Customers would compare Arist to existing LMS products. The team spent six months adding features that mapped to what learning management systems already had—instead of building the fundamentally different thing they were supposed to be building.

“What we’re building is fundamentally so different,” she says. “I have the agency in meetings with executives to say—that’s actually not our perspective. This is what we’re trying to build. This is what enablement should look like in five years, trust us. And it makes them back off a little bit.”

That agency comes from conviction. Not confidence—conviction. Knowing what game you’re playing well enough to explain why certain features will never be built. Maxine tells me she spent significant time enabling the entire company on Arist’s vision. Not just the product team. Everyone. So that when a salesperson gets a feature request in the field, they can explain why Arist won’t build a one-on-one coaching product, and here’s why, and they will never build that, and here’s why.

“Them being able to say those things is super valuable,” she says. “Because then you don’t get all these incoming requests of product to manage.”

I ask whether finding the right buyer helped with breathing room for product.

“Market is everything for product,” she says. Four words. No hedging.

Finding the right buyer improved retention, simplified the roadmap, reduced internal pressure. It did what no process improvement or planning framework ever could: it gave product permission to build the right thing.

Her co-founder, she tells me, is the one who holds the macro stance. “It’s very easy in a business to just really want the wins and explain things in ways people understand,” she says. “It takes a lot of positioning iteration to stick to the macro.”

She mentions other companies in adjacent spaces that built text-message learning tools but positioned them as utilities for learning designers. They don’t see that learning designers won’t exist in their current form three years from now. They’re solving for today’s buyer in today’s category. Arist is building for a category that doesn’t exist yet.

“It does require someone who takes the right macro bets,” Maxine says. “Which you need someone who can do that well.”

I think about Linear’s five-year slide—year one is friends, year two is small startups, year five is enterprise. The CPO who defaults to no on dashboard requests because they’re counter-positioning against Atlassian. The clarity that comes not from better planning but from sharper conviction about who you’re building for.

Maxine and her co-founder have that clarity. It took seven years of positioning iteration, a near-shutdown, a global pandemic, and the courage to walk away from the HR buyer. But they have it. And the roadmap, as she predicted, is taking care of itself.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as Chief Product Officer at Formstack, he oversaw a no-code workplace productivity platform adopted by over 35,000 organizations across healthcare, financial services, and education. Under his leadership from 2022 to 2024, the company expanded its automation footprint across forms, documents, and e-signature workflows, helping customers digitize key processes end to end. He became known for driving cross-functional execution between product, marketing, and go-to-market teams to accelerate subscription growth and retention.

His career highlights include serving as Senior Vice President of Product at Litmus, where he led a four-year stretch of category leadership that earned multiple G2 and TrustRadius awards for product adoption and customer satisfaction. Earlier, as Vice President of Product Management and Head of Product Management and User Experience at Marketo, he guided one of the world’s largest marketing automation platforms through a period when thousands of B2B organizations relied on it to orchestrate multi-channel campaigns. Across these roles, he has spent more than 25 years building teams, products, and businesses at the intersection of SaaS infrastructure, marketing technology, and data-driven customer engagement.

Listen to this episode on Spotify or Apple Podcasts

Learn how LucidLink’s “invisible product” design philosophy connects to Marty Cagan’s high-integrity commitments framework and why the best product strategies are testable assumptions, not finished artifacts.

“We have users who experience it for the first time and kind of call it magic,” Rich Yu tells me. “So it is a bit magical, but obviously there’s no magic in technology. It’s just technology.”

He says this with the calm of someone who’s heard the word magic a hundred times from customers and has learned to take it as engineering validation rather than compliment. Rich is the Chief Product Officer at LucidLink, and his product makes cloud-stored video files act as if they’re sitting on your local machine. You open your Finder, there’s a mount point, and the files are just there. Editors on The Bear scrub through footage with zero latency. No syncing. No downloading. No waiting.

The company just won a technical achievement Emmy for this. And Rich’s philosophy for what comes next is to make the whole thing vanish.

Richard Yu has spent 25 years in product and marketing leadership—Formstack, Litmus, Marketo—before landing at LucidLink, a cloud storage collaboration platform headquartered in San Francisco with an engineering office in Sofia, Bulgaria. The company powers post-production workflows for major streaming shows and found its product-market fit during COVID, when media teams went home and discovered that collaborating on large files remotely was, in Rich’s words, “just not tenable.”

LucidLink solved that with streaming technology that caches intelligently enough to make remote files behave locally. The result is a product whose ideal user experience is one you don’t notice.

I ask Rich what “it just works” actually looks like from the inside—because from a product design perspective, aspiring to be invisible is a strange thing. We spend our careers building interfaces, flows, and experiences that demand attention. Rich is trying to do the opposite.

“We’ve really aspired to become invisible almost in the user experience,” he says. “I know that sounds ironic because as creators and builders of products, we always talk about what’s the user experience and what’s the UI look like.” He holds the irony for a beat. “But ultimately, if we’re thinking about the core value proposition—making large files stored in the cloud act and behave as if they were local on your machine—that’s something that should just happen.”

I tell him about the declining weekly active users problem. A previous guest worked on translation software and discovered that as the product got smarter, people used the app less. For most teams, that graph is a crisis. For utility products, it’s proof of success.

“Exactly,” Rich says. He gets it immediately. For LucidLink, the dashboard exists so administrators can manage permissions and check billing. But the actual value—the streaming, the speed, the absence of friction—that lives underneath everything. The best interaction is the one where a user opens a file, does their work, and never once thinks about the infrastructure making it possible.

We drift into strategy, and Rich surfaces the question that shapes how he approaches product decisions: Are we building outcomes, or are we building outputs?

He’s careful to credit the framework to others—”folks have blazed the path before me”—but the way he deploys it reveals conviction earned through experience. Early-stage companies need outputs. You need to ship the MVP, get it into market, learn. That’s the job. But once you have adoption and momentum, the game changes.

“The value is what is typically called the outcomes,” he says. “Are users really using your product? Are they happy? Is there a community that’s excited and engaged? And then ultimately those outcomes are also company or business outcomes. Is the company growing and successful as a result of the customers being successful?”

This connects to something else Rich is thinking about: the danger of high-integrity commitments.

I bring up Marty Cagan’s framework—the idea that product teams should avoid locking into hard delivery dates unless the situation is truly existential. We’re going to lose this customer if we don’t ship. The business is under threat. Those are the only moments where committing to a specific scope by a specific date makes sense.

Rich admits he falls into the trap himself. “As a product leader, I have accountability to my peers, to my executives, to kind of say, okay, we are gonna ship X by Y date,” he says. “I mean, that’s sort of one of the key anti-patterns in a way—that we are trying to constantly hit very specific dates with projects and initiatives that are not deterministic in that way.”

He catches himself. “But I fall into that sort of trap myself because, let’s face it, in the business world, if we don’t have some forcing functions to get things done, work can fill up the space that it’s given.”

The nuance matters. Deadlines aren’t inherently destructive. The anti-pattern is when hitting the date becomes the only thing you’re striving toward. When shipping replaces thinking. When the forcing function forces shortcuts in discovery, in design, in engineering.

“It forces maybe shortcuts to be taken in the discovery and exploration and validation of that threat,” Rich says. “And then shortcuts taken in terms of the design and the actual engineering of the solution against the threat.”

I push further: when you do make a high-integrity commitment, you need a team that believes in it. Not just one that executes against it, but one that owns it.

“That’s where breaking down the silos across the three functions to creating this true triad ownership is critical,” Rich says. “The ownership in that high-integrity commitment is not engineering by themselves. It’s not design by themselves. It’s not product by themselves. It’s really all three.”

The conversation turns to strategy and Rich offers what might be the most honest thing a product leader has said to me in 165 episodes of this podcast.

“Any strategy, no matter how polished or how baked or how succinctly articulated—they’re just a set of assumptions and hypotheses,” he says. “Hopefully backed by sufficient data and research. But ultimately it’s a thesis. It’s a thesis until you’ve actually achieved the outcome that the strategy is trying to point towards.”

I’ve watched the anti-pattern play out in real time. A product leader presents a strategy. The team pushes back. Instead of engaging, the leader hedges: Well, it was more of a thesis. A work in progress. They were hedging to save face. But Rich is saying something different—he’s saying all strategy is thesis, and that’s not a weakness. It’s how the work actually gets done.

“I’ll go on a limb that even the smartest strategists out there, the most successful folks in technology, are probably always just running one or two steps ahead of reality,” he says. “And they’re trying to really figure things out.”

He reaches for the scientific method. Hypothesize. Test. Verify. Iterate. It sounds basic—cliché, even. But his point is that the discomfort most product leaders have with strategy isn’t that they’re doing it wrong. It’s that they haven’t accepted the nature of the work. Strategy is a hypothesis you test with product decisions. The roadmap is the experiment. The outcomes are the data.

“I really believe that strategy is formed in that cauldron,” he says. “Product roadmaps are formed in that cauldron. And great products are built using that sort of scientific method.”

There’s one more thing Rich keeps circling back to, and it might be the connective tissue between the invisible product and the hypothetical strategy.

He describes how his teams do quarterly reviews to examine the assumptions they made when deciding to prioritize, build, and ship specific features. Did we achieve the user outcomes we assumed? Did those outcomes ladder up to the business outcomes they were supposed to?

“This is hard to do,” he admits. “Because you can always say it didn’t happen because we didn’t market it correctly, we didn’t sell it well. There are lots of mitigating factors. Nonetheless, I think it’s really important for all the product triads to hold themselves accountable.”

The anti-pattern is top-down mandates. When strategy flows from a single leader and everyone else is just executing, accountability evaporates. “Oh, we built this because Rich told us to do it,” he says, narrating the dysfunction. “And then if it doesn’t work out, it’s not anybody’s fault but Rich’s or Rich’s boss.”

He calls it demoralizing and dysfunctional. But the word that sticks with me is erodes. Trust erodes when leaders mandate without inviting the team into the hypothesis. It erodes when outcomes are never checked against assumptions. It erodes when shipping is the metric and nobody asks what happened after the feature went live.

Rich Yu builds a product designed to be invisible. He leads with a philosophy designed to be the opposite—transparent about what’s known, honest about what’s uncertain, accountable to what actually happens when the hypothesis meets reality. The invisible product. The visible strategy. The thesis that never pretends to be a conclusion.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as Founder & Conversion Copywriter at Conversion Alchemy, he led projects that generated up to 30% more qualified demo requests by clarifying value propositions and sharpening differentiation on 20+ core website pages and sales assets. He became known for shortening sales cycles by an estimated 15–20% by making value obvious earlier in the buyer journey and aligning messaging with actual customer priorities. His systems consistently drove 10–15% lifts in trial-to-paid conversions while improving internal alignment across marketing, sales, and leadership.

His career highlights include serving as Conversion Rate Optimizer and UX Designer at Zeda Labs LLC from 2018 to 2021, where he blended qualitative research and experimentation to improve funnel performance and user experience over 2.5+ years. Earlier, he spent nearly a decade in engineering and industrial automation, experience that shaped his systematic approach to messaging, process design, and experimentation. Since 2020 he has also contributed to Good Product Club, writing on product strategy, UX, and go-to-market for teams building in an AI-driven world.

As host of the Message-Market Fit Podcast, he helps B2B SaaS leaders understand how to translate customer insight into narratives that win deals and defend pricing power. Through his Unpacking Meaning newsletter, he publishes weekly breakdowns of SaaS messaging, UX, and buyer psychology for an audience of founders, CMOs, and growth leaders.

Listen to this episode on Spotify or Apple Podcasts

What a software engineer turned copywriter learned about positioning—and why 70% of the work happens before you write a single word.

“If you don’t have a process, AI is gonna produce crap,” Chris tells me. “If you have a process, AI is gonna produce good stuff.”

He says it like it’s obvious. Like the whole discourse around AI and creative work has been missing the point.

Chris Silvestri spent ten years as a software engineer in industrial automation in Italy before transitioning to copywriting. He moved to the UK, founded Conversion Alchemy, and now helps B2B SaaS companies find message-market fit. He writes for Every. He’s not worried about being replaced by AI. But he has thoughts about who should be.

I ask him to break down what he means by process.

“First do the research,” he says. “Then don’t feed all the research to AI and have it write—or sometimes they don’t even feed the research and just ask it to write, which is even worse.”

He pauses to let that land.

“Use the research, distill it into your strategy, and then use the strategy as context for the LLM. So they can actually make sense of the data better.”

This is the part most people skip. They dump raw transcripts and survey results into ChatGPT and expect positioning to emerge. But the synthesis—the actual thinking about what the research means—that’s human work. The AI can help you write after you’ve decided what to say.

“Seventy percent of the work to me is research,” Chris says. “And then the messaging and the copy almost write itself.”

I stop him. I want to make sure I understand the claim. He’s saying the writing is almost incidental?

He nods. The hard part is everything that comes before.

Chris’s engineering background shows up here. He sees messaging as a system with distinct layers. Positioning defines who you are. Messaging is how you articulate that across contexts—sales calls, landing pages, email sequences. Copy is the final layer, the actual words. Most people try to fix copy when the real problem is upstream. No amount of AI-generated headlines will save you if nobody agreed on what you’re saying in the first place.

“A lot of times different departments don’t really agree on what they do better or differently,” he says. “And so then everyone starts kind of saying different things.”

The jargon-stuffed copy that plague B2B websites? That’s not a writing problem. It’s an alignment problem.

I ask about how he approaches customer research when the data is thin. Early-stage companies often don’t have enough customers to build detailed personas.

“I think it’s useful to start with an archetype of your customers,” he says, “rather than saying, okay, this is a specific persona.”

He explains the distinction. An archetype is a representative of a group—business buyer versus technical buyer. Under the business buyer archetype, you might eventually differentiate between CMO, CFO, and procurement. Under technical buyer: CTO, data engineers, developers. But if you’re early, you don’t have the data to specify that precisely yet.

“We weren’t clear,” he says, describing a recent project with a data integration company. “So instead of crafting these ideal customer personas, we drafted these early customer personas. Business side, technical side. And from there we could move forward and get more specific.”

Personas come later, when you have crystal-clear data on psychographics, demographics, decision-making patterns. Archetypes let you start building without pretending to know more than you do.

This matters for AI workflows too. If you’re prompting an LLM to write for a persona you’ve fabricated from guesswork, the output will feel hollow. But if you’ve done the research—if you’ve actually talked to customers and heard how they describe their problems—you can give the AI context it can work with.

“The more you compartmentalize your tasks in LLMs, the better it works,” Chris says. “I don’t even use ChatGPT or Claude for writing directly. There are loads of third-party tools that let you plug into the APIs without that pre-training those commercial interfaces have.”

He’s building his own stack. One tool for finding signal. Another for working through strategy. A third for writing with his editorial style guide. Each chat stays focused. The synthesis happens in his head, not in the model.

Near the end of our conversation, I ask what led him to embrace AI when so many writers are defensive about it.

“I think first it was actually feelings of never being good enough,” he says. Something shifts in his voice. “Maybe it stems from the fact that I’m a non-native English writer. I’ve always said, what if I could be better? And then I saw AI, and now the playing field is level for anyone.”

He decided to try every tool he could find. Learn what actually works. Keep up with the changes happening every week. But what he discovered surprised him.

“Once you have a very specific and systematic process, AI can only amplify that.”

The people most equipped to leverage AI are the ones who invested in their own brains before these tools existed. They have vocabulary. They have frameworks. They know what good looks like.

Chris writes for Every now. He mentions how working with their editors makes him see things from a different perspective. The writer has one job. The editor has another. You try to mirror that same workflow when working with AI.

“The craft, the taste,” he says. “That just makes you better and amplifies your ability to do more with AI.”

I’ve been thinking about this since we hung up. The fear around AI in creative work is often misplaced. The tools don’t threaten people with strong processes—they expose people without them.

Seventy percent is research. The rest is finding the right combination of insights, framing, and context. If you’ve done that work, AI is just another tool in the kit.

If you haven’t, it’s a mirror.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as Global Head of Products & Innovation for Generative AI at Google, he led efforts to help the company’s largest enterprise customers, representing roughly the top 20% by scale, build new products and experiences on modern cloud and AI infrastructure. In that role from 2019 to 2023, he built new global innovation labs, combined sales and P&L ownership with hands-on product advisory, and drove adoption of generative AI across complex, multi-billion-dollar portfolios. He became known for helping Fortune 500 executives move from slideware to shipped product by redesigning how cross-functional teams discovered, validated, and launched new offerings.

His career highlights include a seven-year run at IBM, where he grew an internal DevOps capability 3x into a market-facing advisory practice and later led the North America Digital Transformation practice. From 2012 to 2014 he built a cloud automation service that delivered double-digit growth while helping large enterprises compress infrastructure delivery from months to days. Earlier, he served on the Board of Directors at the DevOps Institute from 2015 to 2019, shaping curriculum and thought leadership as DevOps moved from niche practice to mainstream mandate in organizations managing hundreds of applications and billions in IT spend. He also co-founded Science4Superheroes in 2014, running it for eight years to introduce scientific thinking to children under five through playful, family-centric programs.

As host of the Masters Of Product podcast and author of the AI Empowered PM newsletter on Substack, he helps more than 2,000 product managers each year learn to convert AI from a curiosity into a core part of their craft. Through private workshops, public cohorts, and consulting engagements, his work routinely unlocks multi-thousand-hour annual savings per organization and resets how product teams think about judgment, speed, and quality in the AI era.

Listen to episode 162 on Apple Podcasts↗ and Spotify↗

Building gets easier. Deciding what to build gets harder. Here’s how the top 1% are preparing.

“I had to figure out what I wanted to be when I grow up.”

Mustafa Kapadia says this quietly, almost to himself. He’s describing the moment two years ago when he left Google—after 20 years at places like IBM and Google, running accelerators, building consulting practices, watching digital transformations succeed and fail. And then he walked away to help product managers stop being terrified of the thing that might replace them.

I ask him about the fear. The senior engineers and PMs who’ve told me they’re just... opting out. Done. Can’t adapt. Won’t try.

“I think we have really two camps,” he says. He holds up two fingers, almost making the “peace sign”—then stops. “Well, three camps.”

Camp one: the AI-first believers. They start every task with an LLM. They use ChatGPT for one thing, Claude for another, Gemini for a third, NotebookLM for synthesis. They’ve rebuilt their entire workflow around what AI can do.

Camp three: the skeptics. They want AI at arm’s length. Afraid it’ll outsource their thinking. Afraid it’ll take their jobs. They’re the same people who resisted mobile phones, who pushed back against the internet, who had concerns about every new technology since the printing press.

And then there’s everyone else. The 60% in the middle of the bell curve, trying to figure out which way to go.

“They want to use AI,” he says of the middle camp. “But they don’t really know how. They’re doing surface-level stuff.”

Surface-level. He has a phrase for this. He calls it “using a Ferrari as a paperweight.”

Most PMs use AI for three or four tasks. Summarizing documents. Writing emails. Maybe a little brainstorming. They’ve been handed one of the most powerful tools ever created, and they’re using it to check boxes.

The top 1% do something different.

I’ve felt this myself—the gravitational pull of the easy path. Voice dictation made it so simple to just talk through everything with Claude. I found myself reaching for AI before I’d even tried to think. At some point I started looking for a “brick” for AI, the same way I use a physical lock to keep myself off my phone apps.

I tell him this. Maybe I should get my notebook out first, I say. Try to get as far as I can before—

He cuts me off. Not rudely. Precisely.

“You’re still using AI,” he says. “It’s just a matter of how you’re using AI. Depends on your comfort level.”

Some people think things through first, then use AI to refine their thinking. Others start with AI—”just give me all the options”—then choose the ones they care about, move forward with their own thinking, then use AI to refine it again. Their thought process is sandwiched between AI.

I ask him if there’s a right way.

“I don’t think there’s a right or wrong way,” he says. “I think the more important question is: does it help you become more creative, effective, innovative as a product manager? And if the answer is yes—then more power to you.”

He has a framework. Of course he does—he’s a consultant. But when he describes it, it sounds less like a sales pitch and more like a craft.

“Five keys,” he says. “Assign a role. Provide first-principle inputs. Give it instructions—best practices. Format. And then an example that ties it all together.”

The example he uses is user stories. You don’t just ask AI to write them. You prime the engine. You tell it: you’re world-class at this. You give it the problem, the user, the benefit, the feature. You tell it what a good user story looks like—customer-focused, unique, technical-free. You show it one.

“And then—” he pauses. “Even if AI gives you ten great user stories, you don’t take all ten.”

This is where it gets interesting.

“You take the one or two that resonate. You use your own PM thinking. Your own experience. Your own context.” He calls this human-AI optimization. You’re not outsourcing your thinking. You’re using AI to prime you—to surface options you might not have considered. And then you decide.

The middle 60% outsource their thinking. The skeptics avoid AI entirely. The top 1% sit in the tension between—augmented, not replaced.

The conversation turns to something stranger. Synthetic personas.

Mustafa is working with a client who has years of market research sitting on laptops and servers. Interviews. Surveys. Behavioral data. All of it gathering dust in slide decks nobody opens.

“How do you take that research and make it actionable?” he asks. “How do you give it to someone in sales, or marketing, or product?”

His answer: build a synthetic user. A simulated persona trained on all that research. Something a salesperson can practice objection-handling with. Something a PM can ask, “What would you think if we priced this at $99 instead of $149?”

“It doesn’t replace talking to a real user,” he clarifies. “But in those crazy questions you want to ask—it’s a great way to refine your thinking.”

Then he goes further.

“We have a client who’s building a synthetic competitor.”

I stop him. “A what?”

“A synthetic profile of their competitor. So they can think about second-order effects.” He’s more animated now. “If I drop my price, what is this competitor going to do? If I launch this feature—a feature they already have—how are the two comparing? What can they do to make my feature less valuable in the marketplace?”

None of this means it’s exactly what the competition will do. But it forces you to think. To make better decisions. You can run war games now that were never possible before.

I ask him about the skeptics. The 20% who won’t get on the bus. What happens to them?

He doesn’t sugarcoat it.

“The ship has sailed,” he says. “The train has left the station. Whatever analogy you want to use—it’s happening. The only question as a PM is: where do you want to be? In the driver’s seat? The passenger seat? Or in the caboose, being dragged?”

But then his tone shifts. Softer. Almost conspiratorial.

“If you’re a PM and you’re ambitious—and most PMs are, which is why I love them so much—this is the best time to differentiate yourself. Organizations are dying for PMs who can show an AI-first mindset. They just don’t know what that looks like.”

He’s not selling anymore. He’s confessing.

“I prefer not to talk about what good looks like. I prefer to show them. Because until you actually show someone what a good PM with AI can do—that’s when they say, ‘Okay. How fast can we move?’”

One client started with four or five AI use cases. After his team helped them understand what was possible—what the top 1% actually do—they identified over 250. That’s the gap. That’s the opportunity.

Near the end, he says something that surprises me.

“I think you’re going to need more PMs, not less.”

I must have looked skeptical.

“When you can build anything,” he explains, “deciding what to build becomes a much tougher decision. Building is going to get easier and easier. But figuring out what to build, what not to build, working with the business to determine what’s actually going to make an impact—that’s the job. And I think we’re going to need more people doing it.”

The order-taker PM—business decides, PM translates, engineering builds—that role is dying. What’s emerging is the PM as decision architect. The one who navigates the infinite possibilities that AI unlocks and says: this one. Build this.

He is not wrong. New computer science (CS) students are already doing this.

My engineering manager told me recently that his son is in college, doubling down on AI education instead of a traditional CS degree. The homework is mostly about giving context, setting up system prompts. “This is basically PM work,” I said.

Mustafa nodded when I told him this. It’s becoming a common observation. The engineers need product thinking. The designers need product thinking. Everyone’s developing the competency because the alternative—hiding behind tactical building, being a feature factory—doesn’t work anymore.

We sign off. He mentions a benchmarking study dropping soon—fifty or sixty CPOs, data on how the best are actually using AI. He gives me his Substack. Echo Point.

“I give away 95% of what I tell my clients for free,” he says.

I believe him. And I subscribe before the call ends.

The last thing I remember is him saying something about the middle 60%. How you don’t have to convert the skeptics. You just have to pull the middle toward the top. And once 80% of your organization is using AI for 250 use cases instead of four...

The other 20% stops mattering.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as founder of Shift Nudge, he built a global program that helps designers advance their careers in as little as 8–12 weeks while receiving mentorship and support for a full year, equipping them to lead teams and ship production-quality interfaces. He became known for transforming working designers’ income trajectories, with students reporting income growth of 2x within a few years by applying his methods in typography, layout, and spacing. Through Shift Nudge, he has trained designers from leading startups and global brands, positioning the program as a modern alternative to traditional design education.

His career highlights include pioneering the Float Label pattern in 2013, a form interaction now adopted across products from Apple, Google, and countless consumer applications. He also created the interface design tools Contrast and Flowkit, Figma plugins that have reached tens of thousands of users and are used to check color contrast and design user flows inside modern design tools. Beyond product work, he has served as an adjunct professor at the University of Georgia and delivered workshops and talks at conferences including Adobe MAX, Dribbble Hangtime, Figma’s Config, Smashing Conference, and others, extending his influence from the classroom to stages across the United States.

Listen to episode 163 on Apple Podcasts↗ and Spotify↗

What a decade of design fundamentals taught me about delegating to Claude Code—and why Shift Nudge was secretly an AI onboarding course before AI existed.

“I have a weird obsession with trying to get the absolute most difficult username across every platform,” Matt says, and it lands like a confession. He goes by MDS on the internet. Three letters. You can imagine the negotiations, the dead accounts, the patience required.

We’re a hundred episodes into knowing each other—he was guest number 50, and now here we are past 150—and he’s still introducing himself as someone in transition. “I’m a designer turned educator now sort of turning into a CEO trying to figure out how to run a design education business.” There’s something in how he says trying to figure out that earns the pause that follows.

I’ve watched Matt’s public work for almost a decade. I was the third beta tester to graduate from Shift Nudge back in 2020. I bought low, as I like to say. The course has appreciated since then, but so has something else—something I didn’t understand I was learning until AI came along.

When Claude Code got good enough to actually help with design tasks, I noticed I could delegate effectively while other people couldn’t. The difference wasn’t technical skill. It was vocabulary. Every time I’d tell Claude to “adjust the row height” or “try a card component instead of a list view,” I was drawing from a library of concepts Matt had codified years earlier. Those concepts weren’t just design rules. They were the building blocks of clear instruction. The most valuable thing I learned from Shift Nudge was the vocabulary. When I became a design lead, I could articulate with precise vocabulary what wasn’t working in someone’s design. Subject, object, verb. The spacing is off for this reason. That precision made me good at delegating to humans. Now it makes me good at delegating to machines in the form of Skill files to AI agents.

Matt nods slowly. “Skill files,” he says, “they’re good at getting directionally correct, especially things that are like absolutely binary. Is this the way you write an HTML link or is it not? It’s definitely right and wrong.” He pauses. “Whereas design... there’s more gray area than black and white.” Capturing the nuance a missed in my observation. He’s talking about Claude’s skill files—those markdown documents that give AI context about how you want things done. And he’s right that they work best for the binary stuff. But here’s the connection he helped me articulate: skill files are functionally identical to the Standard Operating Procedures you’d write for a junior designer.

I bring up The Defiant Ones, the documentary about Dr. Dre and Jimmy Iovine. When Jimmy was learning to be a record producer, his mentor taught him by working through him. “Adjust the reverb. What happened there? Why did that work? Why did that not work?” It’s the master-apprentice model, I say. And I think that’s where things are going with AI.

Matt leans into it. “You still need that institutional knowledge, the vocabulary. AI can adjust the reverb and adjust the echo and adjust the panning. Oh, you want five different beats? But it’s like—why? How much? When do we stop?” He lets the questions hang. “That creativity... I think there’s gonna be, you know, in the same way that there was a big resurgence of live in-person things after COVID—I think we’re all gonna be like, it’s just refreshing when I read something online and I can tell that a human wrote it.”

There’s something in his voice when he says refreshing. Like he’s already tired of the alternative.

I ask about the divergence he sees coming—who wins, who loses. He doesn’t hesitate.

“There’s gonna be a divergence where the person who doesn’t use AI is just simply not as effective as the person who learned how to use it. But then there’s also gonna be a divergence of—I’m using AI all the time and this other person is like, well, I learned a lot of things before AI existed and I use AI and now I know more than you.” He pauses. “And this other person’s just fully reliant on AI and they don’t know much.”

It’s gonna be harder to learn things, he says, because AI is so instant. “It makes it like painful to sit down and read something and actually learn it yourself.”

The irony is that the people most equipped to leverage AI are the ones who invested in their own brains before these tools existed.

Matt has a framework for mapping where you fit in all this. He calls it Pioneer, Builder, Consumer.

Pioneers are the people at Anthropic and Cursor and OpenAI—building the intelligence and the harnesses that give it to us. Builders are the developers and designers using these tools to create products. “We’re sort of converging slowly,” he says. “Designers are over here and developers over here, and some are still better at infrastructure and setup and code—like, oh, that’s why would you use useEffect here in React—and designers over here like, what does that mean? But it’s starting to be irrelevant because some of the tools are getting so good.”

And Consumers? “My mom is a good example,” he says. “She’s not choosing to have AI in her life. She’s just seeing it happen through Amazon review summaries or Google AI summaries for the things that she used to search for.”

The question isn’t whether AI will touch your life. It’s which persona you want to occupy.

I push on the vibe-coding hype. All those people on Twitter saying software is cooked because they built a Facebook clone in five minutes.

“I don’t wanna rely on your janky vibe coded app to help me,” Matt says, and there’s a dry humor in it.

I have a follow-up I’ve started using. Whenever someone says “I did this with AI”, I ask: Cool. So what’s your plan to maintain it?

They never have an answer. That’s when you realize why we pay engineers. DevOps, infrastructure, support tickets—that’s the unglamorous work that keeps the train running. Building something on your own is a lot different than supporting a hundred thousand users at once.

Near the end, Matt gets reflective about advice. “You’re gonna need your own knowledge,” he says. “Build that vocabulary through any means possible. Whether it’s asking questions from AI while you’re learning, or watching videos, or attending school. I think there’s still real value in you building your own brain.”

He catches himself. “And if you don’t want to do it—you know, maybe you change careers. I don’t know.” Something shifts. The pragmatism cuts through.

“Just kind of plot yourself,” he says. “Are you a pioneer? Are you gonna be a builder? Are you just gonna be a consumer? Because either way, AI is gonna be touching a part of your life, whether you choose to or not.”

I’ve been thinking about this since we talked. I’m reading books again—not AI books, the fire hose has enough of those. I’m building vocabulary in domains outside tech: marketing, strategy, positioning.

The cost of building has collapsed. The cost of deciding what to build has not.

Everyone with taste is not in tech right now. It’s in the humanities, philosophy, long-form content.

That’s where I’m looking.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as Founder and Principal Writer at Off The Clock Resumes LLC, she scaled a boutique career services practice into a specialized partner for job seekers navigating competitive roles with compensation packages frequently exceeding six figures. She became known for a structured, data‑driven intake process that translates into résumés and LinkedIn profiles optimized for modern applicant tracking systems, significantly increasing interview rates and offer quality for her clients. Through one‑to‑one engagements and digital products, she has supported hundreds of professionals across tech and adjacent industries.

Her career highlights include earning and maintaining the CPRW credential, signaling adherence to rigorous professional standards in résumé writing and career communication. She has continued to refine a distinctive positioning around “career branding that gets noticed and lands interviews with higher offers,” focusing on clarity of story, on‑screen confidence, and repeatable systems that scale beyond any single job search. By combining structured frameworks with empathy for career pivots, she has become a trusted partner for leaders who need to articulate complex trajectories in two pages or less.

Listen to episode 161 on Spotify or Apple Podcasts

Why the old keyword-stuffing playbook is dead. And what job seekers should do instead.

“I am the face behind my business and in front of my business,” Steph says, “as well as the one that does all the one-on-one work with clients.” There’s something in how she phrases it—face behind and in front—that captures the exhausting clarity of solopreneurship. She’s the product and the salesperson. The expert and the marketer. And she’s been doing it since 2014.

She started as a serial job seeker. “I am well rehearsed in job search practices,” she says, with the kind of dry humor that only comes from having lived through too many of them. Now she’s getting ready to attend another annual conference to stay current on hiring tech. The landscape, she tells me, is shifting faster than most people realize.

I ask her what current hiring practices are doing to block talented candidates.

“It’s gone beyond applicant tracking systems,” she says. “That used to be very keyword based. And now it’s not so much the worry of making sure your resume has all the right keywords.” She pauses. “AI is now adding generative and predictive analytics to this technology. It’s actually going to make it easier for job seekers because they don’t have to worry so much about the specific keywords.”

This is counterintuitive. For years, the advice was: mirror the job posting. Product development. Project management. Agile methodology. Match the strings, beat the algorithm, get in front of a human. That era, Steph tells me, is ending.

She walks me through an example. Say a product developer five to ten years ago wanted to tailor their resume. They’d add the term product development to ensure their resume would surface in searches. If someone went into LinkedIn looking for that skill, they’d pop up. “It was really important to have the right keywords, the right phrasing,” she says.

Now? “If you don’t have the specific words—the specific product development phrase—AI is going to look at your experience and it’s going to look at context. It’s going to look at, you know, predictive. If you say you’ve done this, you likely have this skill.” She lets that land. “AI is going to start making assumptions about you that will help you.”

The old systems were deterministic. You could game them if you knew the rules. The new systems are probabilistic. They infer. They read between the lines. This is good news for generalists and career changers—people whose careers don’t fit neatly into keyword buckets.

I tell her this resonates. I’ve jumped between design and product management throughout my career, and I’ve gotten direct questions: What do you actually want to do? Few people accept my honest answer, which is basically whatever the company needs and I find interesting at the time.

Steph nods. “At some point in the last ten years, the trend shifted from wanting someone with a broad range of skills to: we want a specialist, we want someone who really is an expert in this one thing.” She pauses. “But now that we’re adding in this AI element, we’re kind of going back to the original trend where AI wants to see the breadth of your knowledge and then be able to say, yes, this person has these skills, but they also have these skills, which will likely be a good fit.”

The conversation turns to how people market themselves, and Steph lands on an analogy that sticks.

“Highlighting benefits over features,” she says. “Those keywords, those skills—those were features, not the benefits. Whereas now, if you shift your mindset to: I’m going to position myself as the best fit for this job, not because of my skills, not because of the features that I bring, but because of the impact I’ve made.”

She explains how this plays out technically. “One bullet on your resume can speak to an ATS based on the keywords in it—so that one bullet may be associated with project management skills. Whereas now with AI, that one bullet, depending on how much information you give it, might register five, six, seven different skills associated with that one bullet because of the impact you had.”

The example she gives: designing a product that increased efficiency for a large enterprise. That single bullet, written with context, signals project planning, project management, design, strategy—multiple capabilities inferred from one outcome. The question isn’t What can you do? It’s What have you made happen?

I bring up LinkedIn, and how I’ve started writing narrative case studies instead of bullet points for each role. The bet is that AI will read it and extract more context to provide better evaluations to hiring managers.

Steph lights up. “Storytelling, especially on LinkedIn, is key. I used to work with clients very specifically on, let’s take these bullets on your resume and expand them as projects on your LinkedIn profile. Because that project section is also searchable. It’s also readable by the tools behind the scenes.”

She leans into it. “Tell me the full story. How it started. What was the challenge that needed to be resolved. What you did, who you impacted, what obstacles you faced, and then what was the ultimate outcome.” Each project gets 2000+ characters, she says—2000 characters the AI can read, infer from, match you to opportunities.

But the real shift in her thinking, she tells me, isn’t about resumes at all.

“If you don’t tailor your resume for this specific job before you apply, you won’t even be considered,” she says. “I am still a strong believer in tailoring a resume if you’re gonna apply online. But now, because the competition is so high, I would say it’s more important to have a full blown strategy built outside of applying for jobs online.”

What does that strategy look like?

“It’s more important to be strategic in who do I need to talk to? Who can I start relationships with—even if it doesn’t result in a job at that company—but is going to expand my reach in my targeted field or industry?”

She reframes networking as something that makes people less uncomfortable. “You can’t just think of it as networking—just getting your name out there and hoping something lands. But building professional friendships is what is going to make the difference.”

I ask her how she coaches someone who’s just starting out, someone without an existing network.

“Find a trade or professional organization that you can join and actively participate in,” she says. “One that opens you up to develop professional friendships with people you would maybe look at as competitors for different jobs, but they’re also mentors.”

She tells me about a colleague halfway across the country. “She and I just sat down and had lunch together over Zoom and just talked shop. She has sent me referrals. I have sent her referrals. I would call her a mentor, but we’re also friends.” There’s warmth in it. “I know she’s in my corner. She will never do something to jeopardize that professional friendship.”

I share a story from my own career. Five years ago, I had an offer from a company that I turned down for something more interesting. The hiring manager was a class act about it—That sounds really cool, I’m really excited for you—and he kept in touch. For five years. Then, recently, when I was looking again, an opening came up. I interviewed. It went well. Then a budget issue threatened to kill it. Another team needed to shuffle a designer internally. I waited all weekend, assuming it was over.

The recruiter called. We want you here. We have to work this out, but we really want to figure out a way to make this work. They talked to the VPs. Got budget approval. Carved a spot out for me.

“That’s best case scenario right there,” Steph says.

It’s a five-year story arc, I tell her. And it only worked because the relationship was real.

“That is the end goal,” she says. “You’re not going to find that by just applying for jobs on Indeed. You have to do that extra work. And the narrative of this is how you’re supposed to find a new job keeps people from trying.”

She pauses. “Companies are notorious for creating roles for the people they want. If you can figure out what that company’s challenges are and how you can help them solve those challenges—that’s what’s going to help you get your foot in the door at a company you’re gonna be happy with.”

Near the end, she gets reflective. “I didn’t go into this thinking we were gonna deep dive on resumes or LinkedIn. I feel like we really covered a wide range of strategy.”

She’s right. We barely talked about formatting or bullet points. We talked about the slow, patient work of being known. Of building something that compounds. Of treating your career like a series of stories worth telling.

The basics still matter, she reminds me. A solid LinkedIn presence. A resume ready to go. But the game has changed. The people winning aren’t the ones optimizing keywords. They’re the ones showing up—at conferences, in communities, in DMs—building professional friendships before they need them.

That’s the strategy that’s AI-proof.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as Founder and CEO at Solutions 8, Kasim scaled what his M&A advisor described as the largest specialized Google Ads agency in the world at the time of its sale, managing more than $100M in ad spend and growing a fully remote team of over 100 employees across multiple countries. In October 2022 he executed an all-cash eight-figure exit after nearly 18 years building the firm from a one-man web-development operation into a top-ranked Google Premier Partner serving hundreds of clients. That transaction marked his third successful exit after building six different seven- and eight-figure ventures over two decades.

His career highlights include co-founding Driven Mastermind, an invite-only growth community led alongside Perry Belcher and Jason Fladlien that brings together multi-seven- and eight-figure founders for high-velocity experimentation and scale. He also co-founded Nido Marketing, a specialist firm dedicated to helping Montessori schools grow enrollments through digital marketing programs and over 20 self-guided courses built for more than 100 school operators. Earlier, as Co-Host of the Perpetual Traffic Podcast, he helped keep the show consistently ranked among the top 10 marketing podcasts worldwide while publishing weekly episodes over four years to an audience of thousands of practitioners.

As the author of “The 7 Critical Principles of Effective Digital Marketing,” Kasim was recognized by BookAuthority among the 100 Best Digital Marketing Books of All Time and named one of UMSL’s Top 50 Digital Marketing Thought Leaders in the United States in 2020. Through his current project The Daily Sigh at DailySigh.ai, he delivers a 15-minute daily briefing distilling what actually mattered in business, AI, and entrepreneurship for revenue-generating founders, reinforcing his legacy as a strategist who converts complex shifts into practical, founder-ready decisions.

Listen on Apple Podcasts↗ and Spotify↗

Why 20 years of watching “the best product lose” led to a radically different business thesis

“I spent 20 years watching the best product lose,” Kasim Aslam tells me. He lets the sentence land. “I spent 20 years watching the best products go by the wayside. The best kept secret stay a secret. Because they couldn’t drive traffic.”

We’re an hour into a conversation that started with him saying he builds businesses professionally—a phrase so casually delivered it took me a moment to register its weight. Kasim has built the number one ranked Google Ads agency in the world, exited to a SoftBank-backed organization at an eight-figure valuation, and accumulated a portfolio of 17 companies across digital marketing, real estate, and professional services. He’s not on the org chart of any of them. His favorite answer, he tells me, is “I don’t know.”

But before any of that, there were the failures. Over a hundred of them, by his count. Medical transcription. A furniture store. Selling purified mercury. A moving company. Baskets on Amazon. “When I went back and tried to count,” he says, “I couldn’t count every epic failure.”

Kasim was raised by a blind single mother on social security disability. At 22, he lost his job in the 2008 crash with $150,000 in debt. What he found on the other side of those hundred failures wasn’t a better product or a smarter strategy. It was a formula that most entrepreneurs get exactly backwards.

Find the traffic first. Then figure out what problem to solve.

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The insight came from a peculiar vantage point. As the founder of Solutions 8, Kasim spent years managing $100 million in advertising spend for other people. Two hundred clients. Eighty employees. He got to see everything—what things cost, what they sold for, retention rates, competitor landscapes, what attention was actually worth.

“What’s really devastating when you start to wrap your head around what that means,” he says, leaning into the word, “is Google makes more money than you do. You’re slaving away and the traffic stores are eating your lunch. You’re working for them.”

An e-commerce company, he explains, will spend more on traffic than on cost of goods, fulfillment, operations, and customer service. Sometimes combined. The math is brutal. And most founders only discover it after they’ve already built the thing.

Previously, as Senior People Partner – Total Rewards at nbkc bank, she led compensation and benefits strategy for a rapidly evolving financial services organization during a period of tightening labor markets and accelerated digital transformation. In her earlier tenure as People Operations & Benefits Manager at nbkc, she was responsible for end-to-end HR operations for the Kansas City metropolitan footprint, supporting several hundred employees through multi-year change while maintaining compliance, retention, and engagement metrics.

Her career highlights include a seven-year rise at Samson Dental Partners, LLC, where she progressed from Recruiting Manager to Vice President of Human Resources while the organization scaled across multiple states and dozens of dental practices. During that period she built the recruiting function from scratch, hired clinical and non-clinical teams across home office and field locations, and expanded the HR organization to support rapid growth in headcount and locations. Earlier in her career, she sharpened her recruiting and talent acquisition craft at Ferrellgas and Waddell & Reed, managing nationwide and regional hiring mandates in highly competitive markets.

A graduate of Kansas State University with a bachelor’s degree in Hospitality Administration and a SHRM Senior Certified Professional credential renewed through 2027, she has also been an influential figure in the Kansas City HR community through board service with Total Rewards KC and L’Arche Heartland. Through ThriveHR, she continues to advise founders and leadership teams across Kansas City, Southwest Florida, and Houston on building resilient people strategies that scale.

Listen on Apple Podcasts↗ and Spotify↗

The Netflix Problem

Everyone loves the Netflix talent philosophy in theory. Treat adults like adults. Pay top of market. Fire fast. No vacation tracking.

But Kelly sees the gap between billion-dollar companies and the small businesses that make up most of America. A 50-person company in Kansas City can’t offer five engineers’ salaries for one rockstar. They need B players and C players for repetitive, supervised work—and that’s not a failure, it’s reality.

“An A player can’t sit in every single role because they won’t be happy,” Kelly told me. “There are lots of different levels of work that needs to be done.”

The talent strategy has to match the business. A startup founder passionate about their product doesn’t need—and can’t afford—Netflix-style HR. They need someone to take the compliance burden off their plate so they can focus on what they love.

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Control and Money

When I asked about return-to-office mandates, Kelly didn’t hedge: “It’s all about control. Control and money.”

She’s watched clients cling to eight-to-five, sit-at-your-desk policies despite every study proving flexibility drives productivity. COVID revealed something we can’t unsee—life is precious, and there’s more to it than work.

But that doesn’t mean 100% remote works everywhere. Some jobs require physical presence. Some small businesses can’t manage a distributed team. The mistake isn’t having people in the office—it’s treating flexibility as a perk rather than a tool.

“That is 100% a people problem,” Kelly said. “Do you have leaders in place that are holding their employees accountable? Creating an environment where they can ask questions when they don’t know what to do?”

The system—remote, hybrid, in-office—doesn’t determine success. Leadership does.

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The Three-Tier Audit

When Kelly onboards a new client, she starts with the business fundamentals: How do you make money? What are you trying to accomplish? What type of people work best here?

Then comes the audit—every policy, every state, every compliance requirement. Hiring, I-9s, performance management, payroll, termination, offboarding. Top to bottom.

The findings get prioritized into three tiers:

**Compliance first.** “You’re gonna get sued for this stuff.” Fix what the government could fine you for before chasing strategy.

**Tactical second.** Hiring processes, performance reviews, HR systems. Are they efficient? Are the people running them trained?

**Strategic last.** Only after the foundation is solid do you ask: How can the people function support business growth?

“If you don’t have these foundational things in place,” Kelly said, “you really shouldn’t be thinking about strategy.”

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Ask Permission

The most practical advice Kelly shared was disarmingly simple: ask permission.

“I wanna be honest with you, and I’d like permission to share my thoughts.”

She’s never had anyone say no. They might disagree afterward, but they listen. And often they come back later, having processed what was said.

It works with founders, CEOs, leaders with egos—anyone who needs to hear something they don’t want to hear. The phrase reframes confrontation as collaboration. You’re not attacking. You’re partnering.

Previously, as a senior UX consultant at FROM, The Digital Transformation Agency, he led mobile and responsive web experience design for one of the largest U.S. car rental companies, a major Broadway e-commerce platform, and a top payroll provider, contributing to multi-million-dollar online revenue channels between 2011 and 2020. He became known for building cross-platform loyalty workflows across iOS, Android, and responsive web, and for introducing UX strategy practices that informed product decisions through analytics and usability testing.

His career highlights include senior UX roles at Walgreens and Humana, where he shaped e-commerce, mobile, and responsive experiences for millions of consumers between 2011 and 2014. At Walgreens, he helped optimize cross-channel journeys across Walgreens.com and affiliated sites, supporting year-over-year gains in online conversion for properties spanning pharmacy, beauty, and vision. At Humana, he led UX for member-facing mobile apps and loyalty programs, collaborating with innovation teams to move concepts from brainstorming to tested prototypes in an agile environment.

As host and executive producer of the Make an IIIMPACT Podcast, he translates two decades of product and UX leadership into weekly conversations for CTOs and product executives, growing the show to more than 80,000 subscribers and generating over 35,000 views on individual episodes in 2024. He also writes about his journey from robotics and fuzzy controllers to software leadership in essays like his Medium piece “From Broken Glasses to Building Better Software,” extending his influence beyond client work into broader product and design circles.

Listen on Apple Podcasts↗ and Spotify↗

What happens when companies pause everything for eight months to integrate AI and discover nobody uses it.

“The moat is the user experience,” Makoto says. “The easier you make that, the better. No one cares if you’re using Claude or ChatGPT.”

We’re about twenty minutes in, and I’ve been waiting for someone to say this out loud. Everyone’s talking about AI strategy, AI integration, AI roadmaps. Makoto’s been consulting for twenty years, and he keeps coming back to the same point: nobody cares about the backend. They care if it solves their problem.

Makoto Kern started as an electrical engineer in Chicago, building software for manufacturing environments. His job was to automate systems, make them faster, more efficient. But he kept noticing something. The software was built by engineers for engineers—and the people on the factory floor weren’t engineers. They had to use it anyway.

“It kind of naturally led to UX,” he tells me. He started building websites on the side during the .com boom, taking sales calls over lunch at his full-time job, finding work on Craigslist. Eventually he quit and started IIIMPACT. That was twenty years ago.

I ask him what’s been consistent across those two decades. What survives the hype cycles?

“You still see the same problems no matter what the technology is,” he says. “You have to be hyper-focused on knowing that you’re solving someone’s problems.”

The pattern is always the same. During the .com boom, companies added “.com” to their name and watched valuations spike. With crypto, the pattern repeated. Now with AI, he’s watching it again—companies pausing critical feature development to “just integrate AI,” only to discover nobody uses it.

Then he tells me about a case study that stuck with me for days.

One of his clients decided to pause all product development for eight months to integrate an AI chat feature. Microsoft was pushing Copilot. Salesforce was pushing Copilot. Everyone wanted one. So they built one.

“Eight months later it’s integrated,” Makoto says. “We take a look at Pendo. We see a prompt, maybe two prompts during training. Nothing else after that.”

I wait for him to continue.

“So nobody’s using this. And this is exactly why you test.”

The features users had been asking for? On the back burner for eight months. The competitors who kept building those features? Now ahead. Eight months of “innovation” became eight months of falling behind.

“It’s another Clippy right now,” he says, and something in his voice suggests he’s said this before. “People are falling off after using it once or twice. They’re like, I don’t need to use this. I’m gonna go back to what I’m familiar with.”

I bring up the instinct to chase technology—how hard it is to tell a board you’re focused on fundamentals when they’re asking about AI strategy.

Makoto has a metaphor for this. “It’s like telling a kid it’s cold outside, wear a jacket. They don’t wanna wear the jacket.” He pauses. “Then they get sick.”

He says when his team goes into consulting gigs, a lot of these companies are the kid who doesn’t want to wear the jacket. You tell them what’s good process, what’s good strategy. But they’re going to do it their way. “So we go in there. Of course, I bring the jacket. I tell ‘em to put it on after they’re cold.”

There’s something resigned in how he says after.

“Have you heard of the Peter Principle?” he asks.

I shake my head.

“You’re promoted to the point of incompetence.” He lets it sit. “You get somebody who’s a great developer and they’re promoted to manager, but they can’t manage people. So they stop there.”

He’s seen product people say we don’t need to change anything, it’s working as it is. No innovation. Just following what competitors do because it’s the safe play. “If the salespeople heard about this, they’d be like, are you crazy?”

The conversation turns to vibe coding—all those people on Twitter claiming software is cooked because they built something in five minutes. I tell him I’ve been using Claude Code, and it’s incredible for setup, for gluing repositories together. But when things break, I don’t understand what I’m reading.

“Yeah,” he says. “That’s UX.”

Performance is UX. Security is UX. If your dev team creates tech debt and every button takes five seconds to load, that’s not a backend problem. That’s the experience. And with everyone vibe-coding everything, he says, you’re going to see privacy issues, security flaws. His cybersecurity clients are ready. “They’re licking their lips.”

I ask him what he does when the AI hype gets overwhelming—all the noise about automation, about making a hundred thousand dollars a week.

“I just took a step back,” he says. “This is the bubble that people are going after. Don’t pay attention to that. Just stick with the fundamentals.”

He tells me about his own experience with AI. He uses it for crunching data sets, for research, for brainstorming. But he sees the hallucinations. He questions the outputs. “Don’t use it as the end-all, be-all.”

Near the end, I ask what hasn’t been said.

“If you want to innovate, you can’t be scared about utilizing the right resources in the right way,” he says. “Because now if you don’t, it’s going to be detrimental to your company.”

He pauses.

“Don’t rely so much on technology. Always fall back on the right processes. If your product interfaces with users—like most of them do—be super hyper-focused on the user experience. Even if you have board members pushing your CEOs and your leaders into a certain direction, you have to get them to understand: are you solving a user’s pain point or not?”

If you’re not, he says, then who knows what you’re building toward.

I’ve been thinking about this conversation since we hung up. The technology changes, but the failure mode doesn’t. .com boom. Crypto. Now AI.

Same mistakes, faster.

The companies that survive these cycles aren’t the ones chasing features. They’re the ones who remember what the moat actually is.

It’s not the AI. It’s how easy you make it for humans to accomplish what they came to do.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as CEO at Canonical AI, he built “Mixpanel for Voice AI,” an analytics platform that mapped caller journeys across thousands of Voice AI calls to show where and why agents failed, enabling developers to systematically improve conversion and reliability. Between 2023 and 2025, Canonical AI processed large volumes of agent call transcripts and latency metrics, giving Voice AI teams a single interface to debug failure paths and unlock additional call volume from enterprise customers.

His career highlights include founding and serving for 9 years as Co‑founder and CEO of Tule, a Y Combinator S14 company that commercialized UC Davis research into in‑field sensors that directly measure Actual Evapotranspiration (ETa) to guide irrigation decisions. From 2014 to 2023, Tule deployed research-based hardware and software across California specialty crops, with its sensors installed in commercial vineyards and orchards to quantify field‑scale water use and crop water stress, helping growers cut irrigation water use by material percentages while maintaining yields. In January 2023, CropX Technologies acquired Tule, adding its above‑canopy sensing technology to a global precision irrigation platform operating in more than 50 countries.

Rising to prominence in the 2010s as an influential figure at the intersection of agricultural science and data infrastructure, he has since translated that domain expertise into Voice AI analytics and now into real‑time multimodal agent platforms. He remains closely connected to the Y Combinator alumni ecosystem, leveraging over a decade of founder experience—from PhD research commercialization to post‑acquisition leadership—to mentor teams building the next generation of agentic AI products.

Listen on Apple Podcasts↗ and Spotify↗

The Most Dangerous Advantage a Founder Has

Most people think that to start a company, you need experience. You want to know the pitfalls, the market dynamics, and exactly how the “game” is played. We vaunt experience as the ultimate shield against failure.

But Tom Shapland, a decade-long founder turned Product Manager, fundamentally disagrees. He argues that the most important asset he had when starting his first company wasn’t his PhD or his technical expertise. It was his naivete.

“The secret sauce I had is what every first-time founder has, and that is naivete,” Tom shared during our conversation. “You just don’t know how hard it’s gonna be. And you just think, oh, I can take on the world.”

Here’s the thing: experience is often just a collection of reasons why something won’t work. When you’ve seen a dozen startups fail in a specific niche, you stop looking at that niche. When you know how hard it is to build a sales motion in a legacy industry like agriculture, you don’t even try. But the first-time founder doesn’t know better. They haven’t been burned by the reality of the 10-year grind, so they walk into the fire with a smile.

Now, as a Product Manager at LiveKit—building the engine for the voice AI revolution—Tom brings a unique perspective. He *knows* how hard it is. He knows the luck involved. The challenge for the experienced operator is deliberately choosing to ignore those scars and find that same spirit of “delusional” confidence that made the first win possible.

We often talk about “Product-Market Fit” as a destination. But looking at Tom’s journey with Tule, it’s clear that traction isn’t just a metric; it’s an unblocker. Before he had a product, he couldn’t find a co-founder. He couldn’t find investors. He couldn’t find employees. It was only when he stopped building and started pre-selling—getting farmers to sign up for a product that didn’t exist—that everything else fell into place.

Traction unblocks the world. It’s the ultimate signal that your “side quest” is actually the main mission.

As we move into a world where we can simply talk to our computers—where English is the new terminal—the role of the builder changes. Whether you’re a founder or a PM, the job is the same: have the clarity of thought and the naive courage to ask for what shouldn’t be possible yet.

The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Previously, as Chief Product Officer and later Chief Technology Officer at Roblox, Lucas led the product and engineering organizations through one of the strongest multi-year growth runs in the company’s history, helping drive player and revenue expansion of roughly 300–400% year over year heading into 2016. He scaled the product organization from a single product manager and a small design and analytics group to a 30-person, data-driven team, while guiding engineering from bi-weekly releases to daily and weekly cadences across web and core client surfaces. During this period, he helped architect the platform’s shift to mobile-first growth, global game server distribution, and a more systematic approach to discovery and developer incentives, contributing to annual revenue that would later be reported in the billions of dollars as the company matured.

His career highlights include serving as Chief Operating Officer at Instrumental, an AI-powered manufacturing intelligence company where he helped the business grow its customer base across consumer electronics, automotive, and medical devices as revenue expanded by an order of magnitude in the wake of its Intercept product launch. Over two decades in technology, he has held senior roles across engineering, operations, and business, from early-stage leadership at Roblox to advisory work with startups in AI, gaming, entertainment, and enterprise software, bringing a portfolio of experience that spans platform infrastructure, creator ecosystems, and go-to-market strategy. Lucas holds a Ph.D. in Aeronautics and Astronautics from Stanford University and a Master of Public Policy from the University of California, Berkeley, a combination that underpins his analytical approach to building enduring, institution-scale teams.

As author of Impact: How to Inspire, Align, and Amplify Innovative Teams, he codifies a two-tier framework that helps leaders avoid stalled scaling, culture dilution, and loss of focus by treating culture as a system and leadership as a discipline. He now works directly with founders, CEOs, and executive teams as a trusted advisor, helping them design what he calls “engines of innovation” that can sustain compounding impact over decades rather than single funding cycles.

Listen on Spotify

Listen on Apple Podcasts

Innovative teams do not stumble into great products

They intentionally build engines of innovation in how they hire, promote, and operate day to day. Keith Lucas has seen both well run and badly run startups, and the pattern he cares about is deceptively simple:

Purpose-driven companies that adopt a long-term, institution-building mindset have a structural edge over those optimized for short-term financial wins.​

When Keith thinks about building entrepreneurial teams, he looks for five “non-negotiables”:

* Can this person elevate the team’s ability to create, innovate, or solve problems?

* Do they align with the values? Do they want the same long term outcomes?

* Do they believe in the mission?

* Can they live with the team’s non-negotiable principles?

* Do they meet the minimum standards of mastery and autonomy?

Teams that take those standards seriously quickly surface who needs too much handholding or who does not care enough about quality, because the realized culture will not support them.​

Here’s a practical nugget you can take from this episode today (though I recommend you listen to the whole thing, it’s one of the best episodes on leadership)

His favorite hiring and team staffing question for sussing out these non-negotiables is something I am going to steal:

When you have a free moment at work, where does your mind go?

The answer exposes intrinsic motivation, and great leaders use that signal to dial in roles so that enthusiasm, skill, and impact line up instead of grinding against each other.​

Underneath all of this is a simple thesis: if you want an engine of innovation, you need people who behave like mission athletes—mission driven, performance oriented, continuously growing, and elevating their peers—and you need to give them aligned autonomy instead of micromanaged checklists.

This episode is for builders who care about creating something enduring rather than chasing short-term wins, and who are willing to design their hiring, culture, and leadership practices to match that ambition.​

Previously, as Product Manager at Facebook (now Meta), he led the Moments App, AR ads, and Oculus VR initiatives, working on products that collectively reached hundreds of millions of users globally. During his nearly three-year tenure, he operated at the intersection of machine learning, consumer-scale experimentation, and hardware-enabled experiences, which directly informed Flux’s AI-first approach to electronics design.

His career highlights include co-founding 42media group in 2004 and bootstrapping it into a multi-million-euro digital signage and media business serving enterprise clients such as IBM, McDonald’s, DHL, Volkswagen, and major German financial institutions. He also co-founded Hochzeit.de, a wedding marketplace with planning and budgeting tools that grew into a leading German platform connecting thousands of couples with venues and vendors, and he has mentored multiple startup cohorts, helping dozens of founders move from idea to growth-stage businesses.

Listen on Spotify

Listen on Apple Podcasts

Ship platforms that make hardware iteration feel like modern dev tooling.

Matthias Wagner asked an Apple engineer about managing the iPhone supply chain.

“What software do you use?”

“What software? Cubicles full of people. Each one has a phone and a list of numbers. They call suppliers all day, updating a shared spreadsheet. One person can edit at a time.”

That’s the terrain. Not what the frameworks say. Not what the business models teach. The actual terrain.

Summer 2019, Matthias left Facebook to build electronics in his Oakland workshop. Got frustrated immediately.

The tools hadn’t evolved since the mid-nineties. No version control, no collaboration, no automation. Just paper processes ported to Windows.

The map said hardware was hard because manufacturing was expensive and inaccessible.

He tested it. Ordered any semiconductor in the world to his backyard. Unit quantity: one. Seven-day turnaround from China. A few hundred dollars.

The supply chain had democratized completely. The design tools hadn’t budged.

At Facebook, machine learning had transformed everything. Why not here?

A friend told him, “Matthias, you’ve been complaining about this all summer. Do something about it.”

That’s Flux.ai. Making hardware design as accessible as software development.

But here’s the pattern: most builders read the map and execute. Matthias walks the terrain and observes.

The anecdotes don’t match the data. The frameworks don’t capture the friction. The best practices miss the opportunities.

He doesn’t trust what frameworks say should be true. He tests what is actually true. Sources information directly. Builds messy models. Notices the friction everyone accepts as baseline.

The map said hardware required massive capital and factory connections. The terrain showed the real constraint was tools nobody had fixed in thirty years.

That gap between map and terrain? That’s where opportunities hide.

Most product strategy happens in conference rooms. You fill out canvases and positioning statements. Run the plays from the playbook. But you’re optimizing against a map, not reality.

The reality is cubicles and phone calls managing materials for the iPhone. The reality is CAD software that looks identical to 1995. The reality is sourcing spreadsheets with single-user edit locks in 2025.

These aren’t exceptions. This is how things actually work.

You can’t spot that from the map. You have to walk the terrain. Get your hands dirty. Build something yourself. Ask the engineer doing the work how they actually do it.

Test your assumptions with first-hand experience. That’s how you develop real product sense. That’s how you see opportunities others miss by trusting frameworks that describe a world that doesn’t exist.

The map is where you start. The terrain is where you build.

Listen on Apple Podcasts ↗ or Spotify ↗

Guest: Matthias Wagner

* LinkedIn: Matthias Wagner ↗

* Company: Flux.ai ↗

They’re pontificating in conference rooms. Debating specs. Trying to intellectually arrive at the right answer.

The work looks different. The work looks different.

Like Steve Jobs said,

“There’s just a tremendous amount of craftsmanship in between a great idea and a great product… Designing a product is keeping 5,000 things in your brain and fitting them all together in new and different ways… And it’s that process that is the magic.”

It looks like Dan De Mars and his team at Current Backyard are cooking 500 pizzas in two weeks. Prototyping. Testing with real data. Seeing if they can actually deliver before promising anything to the public.

Crust thickness. Topping load. Heat curves. App guidance. Mouthfeel. Every variable they could isolate became another run, another data point, another step toward something that felt right—not just something that looked good in a deck.

This is what intentional design actually looks like.

Dan, head of product at Current Backyard ↗, doesn’t believe in perfection out of the gate. He believes in creating the conditions where a team can learn fast, fail often, and use their collective taste to sort signal from noise.

The result? An electric pizza oven that lets a first-timer cook restaurant-quality pizza without the friction, the learning curve, or the open flame.

But the insight goes beyond pizza ovens.

Great products feel inevitable from the outside because teams did unreasonable amounts of work on the inside. They ran tight feedback loops. They invited more eyes. They treated taste as a filter over hundreds of experiments, not a single flash of genius.

Dan also talks about designing for “limited grillers”—urban dwellers constrained by space, fire restrictions, or time—who still want great food without the heroics. It’s a masterclass in finding underserved segments and building for real constraints.

If you’ve ever wondered how “it just works” products come together, this conversation is the blueprint.

Listen on Apple Podcasts ↗ or Spotify ↗

Links

Dan De Mars on Linkedin ↗

Current Backyard ↗

00:00 The Essence of Design

01:17 The Journey of a Designer

02:17 Philosophy of Design

03:25 Unlearning and Relearning

09:44 Innovating Outdoor Cooking

18:41 Targeting the Modern Cook

25:56 Innovative Launches and Product Expansion

26:52 Competing with Convenience: The Pizza Oven

28:26 Designing for User Experience

31:05 Prototyping and Iteration Process

34:31 Balancing Functionality and Aesthetics

44:29 Final Thoughts and Future Directions

In my recent conversation with David Trier, VP of product at ModelOp, he described the current state inside large organizations as “the Wild West of AI”—dozens of teams, hundreds of tools, and no shared way to get models safely into production.

The reality is that many enterprises are staring at portfolios of 50 to 100 generative AI use cases, but only a handful ever make it into production, often taking six to 18 months to ship.

What clicked for me in this episode was David’s analogy: ModelOp is essentially ServiceNow for AI.

ServiceNow gave IT leaders a consistent, auditable way to turn messy tickets into reliable service management. ModelOp does the same for AI initiatives: it sits at the enterprise layer, orchestrating 10 to 12 teams and systems—data, security, legal, risk, compliance, infrastructure—so AI projects move through a repeatable playbook instead of one-off review cycles.

David walked through a financial-services case where this approach cut time-to-production in half, turning 18‑month science projects into AI services that ship in weeks and generate business value before models degrade.

For product leaders and CTOs, the takeaway is simple: if AI is a C‑suite–sized investment, it needs C‑suite–grade governance, not grassroots experimentation scattered across the org.

If you are thinking about how to move from proof‑of‑concept chaos to an enterprise AI operating model, this episode is worth your time.

Listen on Apple Podcasts ↗ or Spotify ↗

Mentions

* ModelOp ↗

* David Trier ↗

In the latest episode of the Way of Product Podcast, I had the pleasure of chatting with Brian Donohue, Vice President of Product at Intercom. Brian has been a critical player at Intercom for over 11 years, where he has navigated the company’s growth and transformation, especially in the ever-evolving world of AI integration.

Brian shared his insights and experiences in transforming product development at Intercom, focusing on building a Fin AI agent that’s set to redefine customer support.

With over two years dedicated solely to AI, Brian discussed the company’s journey from its early machine learning beginnings to embracing large language models.

Connect with Brian on LinkedIn

Listen to The Way of Product: Apple Podcasts or Spotify

Actionable Takeaways✅ Embrace the uncertainty and potential of AI-driven product innovation.

✅ Aligning incentives through outcome-based pricing instead of traditional SaaS models.

✅ Balancing traditional product management structures with innovative AI development approaches.

Time Stamps

04:15 AI Integration in Product Development07:40 Architectural and Product Thinking in AI11:05 Challenges and Innovations in AI Implementation18:00 Continuous Improvement and Reassessment24:50 Inherited Product Design Flaws31:35 Technical Rigor and Product Validation37:10 Evolving Product Management Practices42:15 The Role of AI in Modern Product Development49:20 Outcome-Based Pricing Explained55:00 AI Transformation and R&D Services59:30 Adapting Product Development to Customer Needs66:45 Final Thoughts and Future Outlook70:20 Connecting with Brian Donahue

01:14 Choosing to Work at Exa

01:24 The AI Revolution and Its Impact

02:25 Challenges and Opportunities in AI

04:30 Managing Expectations with AI

05:28 The Role of Product Managers in the AI Era

11:23 The Importance of Technical Literacy

22:25 Lessons from McKinsey

25:52 Adapting to AI in Product Management

33:04 The Concept of Agency

39:31 Conclusion and Final Thoughts

Unless you aim for the highest role at a company, you’ve somehow failed.

My next guest on The Way of Product Podcast, Jamie Toyne, challenges that idea.

Jamie’s been there and done that. he’s been the CEO, sold the company, and travelled the world. The right fit might be coaching, consulting, or serving as the creative force behind someone else’s vision—like Jony Ive was to Steve Jobs.

Following formulas that ignore your true nature leads to burnout and misalignment—success is not measured by title, but by how invigorating the work feels.

Enzo Ferrari, James Dyson, Dietrich Mateschitz (Redbull), Jony Ive, didn’t optimize for careers that make a bunch of money, they did work they unlocked their talents, gave them energy to be creative during the hard times, and the structure their creative expression.

If you are doing great work that aligns with your unique talents and values, the market will reward you, companies will fight to retain you, and people will want to invest or purchase what you build because you are involved.

Turns out, great work is hard to come by, and putting someone who’s energy isn’t aligned with the work doesn’t lead to great work.

This episode is for anyone who doesn’t feel like they are doing work that aligns with their wiring. I certainly benefited from the conversation.

-CadenListen to The Way of Product: Apple Podcasts or Spotify

In this episode, Jamie Toyne recounts his personal and professional journey with ADHD—from growing up in Australia, building a successful mergers and acquisitions firm in San Francisco, to starting an ADHD coaching career. Jamie experienced significant burnout, moved to Mexico, and later sold his business.

He discusses the challenges and benefits of living with ADHD as a business leader, the importance of doing work that aligns with personal values, and how his coaching program helps people with ADHD perform better and prevent burnout. Jamie explores recent changes in how society understands ADHD, and what these shifts mean for modern workplaces.

LinkedIn: https://au.linkedin.com/in/jamietoyne1

Free 1:1 ADHD Coaching Session: www.jamietoyne.com

00:30 Journey to San Francisco—and burnout

02:15 Life as a Digital Nomad

03:48 ADHD Diagnosis and Early Life

05:07 Tennis Career and Education

08:44 Entrepreneurial Challenges and Burnout

13:48 Balancing Ambition and Lifestyle

18:46 Reflecting on Business Structure and Superpowers

19:11 Dealing with Imposter Syndrome and Financial Decisions

20:35 Team Dynamics and Company Culture

22:50 Passion for Coaching and Exit Planning

26:50 ADHD and Leadership Challenges

33:14 Finding Flow and Realigning with Passion

Key Topics Discussed:

* The Mural integration trap: How responding to customer feature requests can lead to becoming an integration factory

* Output vs. outcome-driven roadmaps: Why shipping features fast matters less than scaling the right thing

* The validation framework: Moving from idea to experiment to validated roadmap before building

* Qualitative vs. quantitative data: When to trust customer anecdotes over usage metrics

* Zero-to-one product development: Building without data in early-stage companies

* Meeting equity and hybrid work: How Neat approaches designing for distributed teams

* Simplicity in hardware: The phone camera principle and why accessibility beats perfection

Key Quotes:

“You gotta have the conviction to take a step back and say, look, what is the real outcome that I’m trying to drive here?”

“If I had just spent maybe the next quarter validating this as an experiment...what they would’ve told me is they want App X, they want Figma, they want Y...This is not about just making the dollar signs with the mural. This is about the wider customer problem.”

“The hardest word in product isn’t ‘no’—it’s ‘wait.’”

“Often moving slow is a problem...but I think a bigger problem is not scaling the right thing.”

Featured Story:

The Mural Integration Decision: Kritarth details how a seemingly rational request for a Mural integration—backed by top-three usage data and tied to major deals—would have led Neat down the path of building an integration team that services infinite requests. By spending a quarter validating the underlying customer need, they discovered enterprises wanted workflow integration across their entire app ecosystem. This insight led to building an App Hub marketplace instead, creating a platform that scales exponentially rather than linearly.

Resources Mentioned:

* Book: Escaping the Build Trap by Melissa Perri

* Neat’s App Hub marketplace

* Product Kata framework

About the Guest:

Kritarth Saurabh is VP of Product Management at Neat, a video conferencing hardware company focused on simplicity and meeting equity. Before Neat, he spent years in consulting at Boston Consulting Group, Accenture, and Deloitte, working with Fortune 500 companies and startups on product development. He started his career as a software engineer and has experienced the full product lifecycle from ideation to sunsetting.

Connect with Kritarth: https://www.linkedin.com/in/kritarthsaurabh/

About NeatNeat manufactures video conferencing devices designed to keep meetings simple and equitable, whether participants are in-office, remote, or hybrid. Their products include the Neat Board Pro, an all-in-one 65-inch integrated screen with camera and speaker capabilities.

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That shift started before this interview—after I ran a complex API exploration through an AI research assistant and got back a thorough, sourced report with working links.

But my conversation with Margaret-Ann Seger (who leads product and design at Statsig, the intelligence infrastructure platform for feature flags, experimentation, and analytics) turned that insight into conviction. And the timing makes this even more interesting: Statsig recently announced it’s being aquired by OpenAI.

If OpenAI sees enough value to combine forces, the way Margaret and her team work is worth studying.

Here’s the core change I’m making in my own work: let AI collapse the paperwork so humans can concentrate on judgment. When I dump a messy outline into a model and it returns a clean structure in minutes, I don’t feel threatened; I feel focused.

Margaret described a world where PRDs update themselves from meeting inputs and auto-ticket the next steps. That’s not cutting corners. It’s cutting ceremony. The value we bring isn’t keystrokes—it’s synthesis.

Synthesis shows up in how we decide what to build when shipping gets cheap. AI lowers the barrier to creation, which raises the bar on taste. It’s not enough to ship more; you have to choose better—distill the real pain, reconcile what users say with what they actually do, and shape solutions that feel right in the hand.

Margaret triggered a new habit for me: I now write a one-paragraph “taste test” before we commit: Why this problem? Why now? Why this approach? If I can’t explain it plainly, we aren’t ready.

The conversation also reframed “soft skills” as the durable edge. You can’t paste three years of team history into a prompt. Reading the room, sensing when engineers don’t buy a solution, remembering why a past decision failed—these are still human advantages. Margaret called out the friction every PM knows: users tell you one thing in interviews and do the opposite in product. Someone has to hold both truths at once and decide. That someone is still us.

One practice of hers made that human edge tangible: make customer support everyone’s job. At Statsig, support isn’t a silo. They rotate it. Designers answer confused tickets and see where the UI collapses. Engineers feel the frustration firsthand and often fix root causes quickly. It’s tempting to route everything through a bot for speed, but there’s a hidden cost: you lose the raw empathy that powers taste. We’re piloting a similar rotation and tracking the fixes it sparks.

Another theme was moving learning into production. Prototypes were born when shipping was expensive. As that cost falls, high-fidelity demos give way to small, live experiments that gather real data. Margaret’s ideal cadence is to spend more time on problem analysis and then release multiple small bets behind flags. I’ve started doing the same for ambiguous flows: define two or three minimal viable variants, ship them to real segments, and time-box the learning window. Data beats debate.

On the tooling side, Margaret pushed me to point AI at sources of truth, not just the documentation. Docs always lag. Code doesn’t. Her team is exploring agents that answer questions grounded in the codebase and SDKs. I loved the example of customers repurposing Statsig’s experimentation tool to benchmark models and prompts offline—a reminder that good tools get bent into new jobs in the AI era. We’re trialing a code-aware path for technical support and an internal agent trained on our repos for integration questions.

Something else I’m now normalizing: don’t hide your AI usage. Margaret hired a PM who clearly used AI on the take-home. That wasn’t a disqualifier; the deciding factor was his judgment. The stigma needs to go. Show your work, raise the standard, and trade playbooks. We’re adding a simple line to retros: “How did AI help?” When the practice is visible, everyone gets better faster.

Two moments from the interview keep replaying for me. The first was our “soft skills” segment, because it names what PMs actually do when the tools get powerful: we arbitrate between truths, people, and paths. The second was personal and small—Margaret and her husband use AI to make songs for everyday moments and stories for their kid. It’s a reminder that this wave isn’t only about efficiency; it can unlock more human connection at scale.

Here’s where I’ve landed:

* I no longer treat AI as a novelty or a threat. I treat it as an accelerant. It compresses the “what” so I can deepen the “why.”

* I’m biasing toward live learning and away from document theater: fewer perfect specs, more real outcomes.

* I’m putting empathy on the front line (support rotations), taste at the gate (the one-paragraph test), and code at the center of truth (repo-grounded agents).

If you’ve been skeptical like I was, start small: choose one active project, let AI handle the formatting and ticketing, and spend the saved hour with a customer or sharpening the problem statement. You may find your job doesn’t get smaller. It gets truer.

And in a world where a company like Statsig is merging with OpenAI, getting to that truer version of product work isn’t optional—it’s the edge.

Listen to The Way of Product: Apple Podcasts or Spotify

Margaret-Ann Seger, leader of product and design teams at Statsig, and after the acquisition from OpenAI, part of their Product Staff, discusses the evolving role of AI in product management on the latest episode of The Way of Product. While AI can automate many tasks, human judgment remains crucial. She shares insights on how AI can supercharge productivity and reduce drudgery, allowing PMs to focus more on strategic thinking and deeper customer understanding. Margaret also explores the idea that future PM tasks will blend with design and engineering roles, facilitated by AI tools. She remains optimistic about AI's impact on creativity and productivity.

Listen to The Way of Product: Apple Podcasts or Spotify

00:00 Introduction to AI and Human Judgment

00:33 Meet Margaret Ann from Statsig

01:16 Debating the Future of Jobs in Tech

02:45 The Importance of Taste in Product Management

06:34 Soft Skills and Human Empathy in Tech

12:33 The Role of Engineering Background in Product Leadership

15:46 AI's Impact on Research and Data Gathering

20:23 Embracing Technological Progress

20:42 The Joy of Creating with AI

22:18 AI in Product Management

24:32 The Future of Work with AI

25:45 Exploring AI Tools and Their Impact

31:23 The Role of AI in Knowledge Management

34:21 Optimism for the Future

35:25 Closing Thoughts and Encouragement

Thank you for reading this week's episode of The Way Product. This publication is intended to be free indefinitely.

depending on your product strategy...

Andrew Saxe, VP of Product at Smartling, joined me to unpack why.

When a system translates intent well and runs in the background, people don’t have to log in—and the work still gets done.

We discussed designing for “manage by exception,” placing guardrails where failure would be costly, and allowing automation to carry the load.

We looked at the feature request funnel too: why thousands of asks don’t equal thousands of tickets, and how building a few verbatim specs for large customers can still lead to unused features, tech debt, and wasted opportunities.

Listen to The Way of Product: Apple Podcasts or Spotify

Timestamps:

02:48 The niche translation industry and Smartling’s impact

11:28 The role of AI in translation

13:55 AI’s impact on Smartling’s product roadmap

16:38 Managing translations with AI and human oversight

22:00 Optimizing translation services for market expansion

22:47 Challenges and nuances of multilingual customer research

23:41 The art and science of requirements to spec translation

29:18 Feature requests and customer feedback

31:26 The importance of understanding user needs

34:27 The future of translation and AI

38:37 Concluding thoughts and contact information

24:56 AI and Translation: Balancing Automation and Human Touch

28:19 Feature Requests and Customer Feedback

30:27 The Importance of Understanding User Needs

35:42 Managing Translation Budgets and Quality

37:39 Conclusion and Final Thoughts

That same obsessive attention to overlooked details drove him from coding in his dorm room to leading product at Summer, a public benefit corporation tackling America's $1.8 trillion student loan crisis.

In our conversation, Michael discovered something shocking: The majority of people defaulting on student loans qualified for affordable payment plans—they just never knew these options existed. During the pandemic payment pause, borrowers' loans got sold, addresses changed, autopay broke. Prime credit scores tanked overnight through no fault of the borrower.

"We're not dealing with edge cases," Michael explains. "These are normal people who did everything right, caught in a system that's surprisingly complex for what should be simple."

We cover:

→ Diverse teams catch problems homogeneous ones miss (hire for "culture add" not "culture fit")

→ Where there's confusion, there's opportunity to help at scale, and how to spot opportunities.

This episode covers student loan solutions. But it's really about building products that meet people where they struggle most—and the leadership philosophy that attracts top talent to mission-driven work.

Timeline:

03:01 FinTech Trends and Student Loans

04:07 Challenges in Student Loan Management

05:58 Summer's Approach to Solving Student Loan Issues

10:48 Employer Benefits and Financial Wellness

14:45 Navigating Regulatory Changes

17:37 Product Management Insights

20:09 Proactive Messaging and Customer Experience

29:06 Hiring and Team Building

It is a question of stewardship. As we rush to integrate AI and other technologies, are we thinking beyond the next quarter, the next release cycle? Are we willing to accept responsibility for the unintended consequences?

AI, for its part, is neither savior nor villain. Ben Rennie sees it as an amplifier—a tool that accelerates the work but does not replace the worker.

For example, he used AI to help finish his book, but the ideas and the voice are his own. The lesson is clear: technology can be a partner, but it cannot do the hard work of thinking, of feeling, of connecting the dots that only a person can see. When I write, using AI as an editorial partner, primarily for packaging ideas rather than generating them, has been a game-changer in helping me express myself. To the world better.

So I'm happy to present Ben and his interview on the podcast, where we dive deep into where creative work is going in the age of generative AI.

-Caden

“80% of the world’s climate challenges today stem from the design phase of a product or service. We’re building things without recognizing the impact. Human-centered design means designing for people, but we often ignore the systems in which humans exist.”- Ben Rennie

Listen now on Apple and Spotify.

In this episode, I speak with Ben Rennie, co-founder of Reny®, about his career as a designer and entrepreneur spanning more than a decade. Ben shares how he started his consultancy in 2009, explains its evolution, and discusses challenges he has faced and lessons he has learned along the way.

The conversation explores systemic design and why understanding the broader impacts of human-centered design matters. Rennie introduces his book, Lessons in Creativity, in which he examines the creativity gap and explains how fear can stifle creative confidence as people grow older.

We also discuss the relationship between creativity and artificial intelligence, challenges in sustainable design systems, and stories from Rennie’s experience that highlight the importance of perseverance and bravery in creative work.

The episode offers practical insights for anyone interested in creativity, technology, and human-centered design from a veteran in the creative industry.

If you want to learn more about Ben Rennie, his work, or his thinking on creativity and design, check out the following:

* Ben Rennie on LinkedIn — Connect with Ben and follow his latest updates.

* Lessons in Creativity on Amazon — Explore Ben’s book for stories and strategies to cultivate your creative confidence.

* Reny® (Ben’s agency) — Discover the consultancy Ben founded and see their latest projects.

Timeline

00:12 Starting the Business Journey

00:28 Personal Reflections and Challenges

01:01 The Importance of Systems and Design

01:25 Balancing Personal Life and Work

02:45 Discussing the New Book

03:03 Exploring the Creativity Gap

07:07 Systemic Design and Environmental Impact

17:31 The Role of AI in Creativity and Work

27:04 Exploring Human-Centered Design

27:37 AI Tools for Enhanced Productivity

31:25 Transition Design and Future Innovations

34:33 Creative Confidence and Overcoming Fear

35:46 Personal Stories of Creativity and Bravery

46:07 The Importance of Meaningful Work

My business partner and I had a suspicion that we were prioritizing the wrong features. Instead of asking customers directly for feedback, we observed their behavior and used that data to inform our product decisions.

Historically, product managers have wanted product feedback, but it is often difficult to collect and use. The rise of APIs has made gathering feedback much easier, yet many product managers remain stuck in older ways of working.

It is tempting to say, “I want to build this,” and assign ten or twenty developers to work on pet features.

We believe that model of product management is fading. You will increasingly rely on data—both customer and qualitative data—because if competitors do so, they will be closer to the customer, serve them better, and you risk falling behind.

In a world where intelligence is widely accessible and anyone can build nearly any feature at minimal cost, what truly matters?

I am not one to make predictions, but a few factors stand out as difficult to replicate:”

-Kareem Mayan

Listen now on Apple and Spotify.

In this episode, we’re joined by Kareem Mayan, co-founder of Savio.

Savio.io is a product management platform that centralizes and organizes customer feature requests and product feedback, enabling B2B SaaS teams to build evidence-based roadmaps and prioritize features that matter most.

Kareem has more than two decades of experience in product management and entrepreneurship—including roles at ESPN and MySpace, and three successful startup exits.

Here’s what we cover in the episode:

* Transforming product management and SaaS operations with AI, machine learning, and automation

* Building user-centric products through deep customer understanding and feedback

* Centralizing and acting on customer feedback with integrated tools and platforms

* Making data-informed decisions by blending analytics with qualitative insights

* Preventing churn proactively using predictive analytics and early warning systems

Listen now on Apple and Spotify.

Where to find the topics:

00:53 Lessons from Mayan’s first startup experience02:39 Insights from subsequent ventures05:05 The importance of sales and marketing07:10 Product management and customer feedback08:01 AI and the future of product development13:34 Qualitative feedback in B2B SaaS17:01 Starting the current company18:49 Transition to a mid-market strategy19:05 Prioritizing customer feedback19:32 Savio’s approach to feedback management20:36 Founders’ journey and insights21:52 Challenges and solutions in product management22:13 Data-driven product development26:57 Balancing big wins and incremental improvements31:49 Steve Jobs myths around customer feedback

Communities are more than just support forums; If deployed correctly, they can be a fantastic channel for product teams to sift signal from the noise.

In the latest episode of Way of Product, I had the pleasure of chatting with Jake McKee, a seasoned community expert with over 20 years of experience working with companies like Apple, Lego, and clients such as Southwest Airlines and H&R Block.

In this interview, I chat with him about his journey in the customer engagement space, working with major brands like Apple Global Support, Lego Global Community, and more.

His expertise in creating community-driven product development strategies and operationalizing community feedback in large organizations like Apple offers unique insights for anyone looking to enhance their customer engagement programs.

Listen now on Apple and Spotify.

And if you like what you're listening to in this episode, I highly recommend checking out his work at jakemckee.com

Actionable Takeaways

✅ Bridging the Gap Between Customers and Companies

✅ Empowering Customers to Become Advocates

✅ The Power of Relational Customer Engagement

Time Stamps

02:45 An Introduction to Jake and His Journey in Community Development

06:22 Bridging the Gap Between Customers and Companies

13:10 Apple Community Insights

18:08 Operationalizing Community Feedback

27:45 Community-Driven Product Development

37:00 Challenges and Strategies in Community Engagement

46:30 Understanding Developer Needs Beyond the SDK

57:50 The Importance of Honest Communication

1:06:20 Creating Shared Success in Communities

1:15:05 The Power of Relational Customer Engagement

1:25:15 Final Thoughts and How to Get Started

Bridging the Gap Between Customers and Companies

"My work has always had some connection to bridging the gap between customer and company."

—Jake McKee

Jake emphasizes the importance of community programs over mere platforms. He believes in building long-term programs that foster genuine relationships between companies and their customers. This approach leads to better customer satisfaction and product development.

Takeaway: Focus on bridging customer-company gaps through meaningful community programs, leading to enriching customer relationships and better product insights.

For me, meaningful customer engagement means meeting them where they're at - at industry events—creating a third place where people could hang out at those events, like a lounge or a podcast. Apple invested heavily in SEO for its support community. So that if you looked up anything Apple-related, there would be a support community link.

Empowering Customers to Become Advocates

"You don't create fans without a relationship."

—Jake McKee

Jake discusses the power of empowering customers as advocates through transparency and open communication. He highlights how involving community voices in product development processes can lead to better products and product launches.

Takeaway: Empower your customers by involving them in your processes, building trust, and creating advocates who support and promote your brand.

To do that, customers need to feel seen, heard, and understood. They need to think that you're building on their behalf, that you're making their work possible, and that they feel empowered to share how fantastic your product is.

The Power of Relational Customer Engagement

"Think about relational activity, not just data gathering."

—Jake McKee

Jake shares that successful customer engagement relies on building genuine relationships rather than focusing solely on data collection. This relational approach encourages consistent and meaningful interactions with your audience, leading to long-term connections.

Takeaway: Build relational connections with customers, treating engagements as social conversations to foster trust and long-term loyalty. You create loyalty by giving and establishing a sense of reciprocity. Doing things that you don't have to do as a company are great ways to generate reciprocity.

That's another episode. Listen to the whole thing to get all the extra context that wasn't included in this post.

Again, thanks for opening and listening.

Cheers,

Caden Damiano

Today's guest is Steven Puri, CEO of The Sukha Company, which develops one of the most popular productivity and focus apps, Sukha.

Connect with Steven on Linkedin.

Listen now on Apple and Spotify.

Steven has a diverse background in both the film and tech industries.

As a former senior executive at major motion picture studios and a tech entrepreneur who has raised venture capital for startups, Steven brings a unique perspective on creativity and leadership.

Here’s his IMDB page; he’s worked on films like Independence Day, Godzilla, and Braveheart.

He shares some pretty awesome behind-the-scenes stories with directors like Roland Emmerich. He's a fantastic storyteller. I was hooked every time he told a story, and they were hilarious and entertaining.

During our conversation, we discussed:

✅ The parallels between launching films and tech products and the challenges of scaling creative projects.

✅ The application of remote and hybrid work models from film production to today's tech environments.

✅ The impact of flow states on personal efficiency and keeping your team productive.

Important Time Stamps:

- 03:15 - Steven’s transition from film to tech

- 12:30 - Adapting film production strategies to tech

- 25:45 - Cultivating flow states for better productivity with Sukha

Actionable Takeaways

Break Down Big Tasks: Flow Gets Unlocked by Tackling a Manageable Chunk of Work

Steven emphasizes the power of tackling big tasks by breaking them down into smaller, manageable steps. This provides your brain with a way to begin forming connections to the broader picture.

"And if you do put something crazy on there, like, I have to write this week's episode, it suggests like the estimate on that is probably 16 hours. You're probably not gonna do it before your brain blows up. What if, instead of writing the episode, you did an act one outline?"

- Steven Puri

Takeaway: My favorite thing to do before writing a PRD, or when I was designing, was to focus on creating a wireframe or writing an outline to get to a v0 of a work output deliverable. That v0 work informs the gaps in my thinking, which provides different paths forward to make progress.

Steven's approach here is influenced by decades of experience in the film industry, where phases are broken up into different levels of fidelity: storyboard, script, and logistical documents. The whole concept of pre-production is to break up the work into manageable chunks so that, if followed, you don't have to have as much thrashing in the production phase of a movie or TV show.

The film industry has been using remote and hybrid work for decades

Steven highlights the effectiveness of hybrid work, blending remote and in-person collaboration, as a way to adapt to current work environments.

We've long recognized the necessary balance of structured planning and creative freedom in filmmaking, from remote idea nurturing and production intensity to remote post-production work.Hollywood has been doing remote for a very long time. You're writing a script at your house. You're creating storyboards and logistical documents on your iPad in a café.

Hybrid work is when you're in the studio pitching a script or in the writer's room, roughing out final details.

And production is when you're in the office. You're showing up to work every day. Sometimes 12+ hours a day. The beautiful thing about Hollywood production is that it respects all the different work locations and styles, encouraging creative results.

"Belonging to a community enhances performance and motivation… Balancing remote and in-office work helps unlock creativity."

- Steven Puri

Takeaway: A hybrid model can maximize both focused independent work and team efforts. I'm a big fan of working from home to complete my IC tasks and collaborating on Zoom or Google Meet. However, those work trips, where we travel to a co-working space or fly out to an office, have been crucial in my experience for making those big strategic decisions.

Balance your work schedule to harness the strengths of both approaches.

Leverage Downtime for Creativity

Steven encourages using downtime or even multiple projects to access creative insights that might otherwise remain untapped.

He calls it the "other thing", and when managing teams, he tries to give writers, engineers, or designers another thing to work on so that if they're blocked in one area, they could go work on something else.

"The great ideas happen when you're thinking about something else."

- Steven Puri

Takeaway: Embrace moments of mental wandering during routine tasks. These breaks can lead to innovative solutions and fresh ideas.

I hope these takeaways provide you with actionable insights to enhance your productivity and creativity. Listen to the full episode to hear behind-the-scenes stories of films like Independence Day, Godzilla (the one with Matthew Broderick), and much more in the whole episode.

Listen now on Apple and Spotify.

Cheers,

Caden Damiano

Today’s guest is Thomas Payet, one of the co-founders of MeiliSearch, an open-source AI-enhanced Search API that is plug-and-play and can be deployed in just a matter of minutes. Smart presets let you start searching through your data with zero configuration.

Thomas explained how focusing on simplicity and accessibility in their search API aligns with their mission to empower developers and enhance user experience across applications.

Our discussion also touched on the value of the collective vision of the founding team in building a successful tech company.

Connect with Thomas on Linkedin.

Listen now on Apple and Spotify.

𝗠𝗲𝗶𝗹𝗶𝗦𝗲𝗮𝗿𝗰𝗵 𝗙𝗲𝗮𝘁𝘂𝗿𝗲𝘀:

* Out-of-the-box search experience that reduces integration time and complexity.

* Intuitive design that allows developers to enhance search capabilities without extensive customization, seamlessly.

* How Meilisearch is a perfect example of the commoditization of most table-stakes functionality in software.

* Why create your search algorithm when you can buy one from MeiliSearch?

* Why should you worry about developing yet another technical solution for collaborative docs when other companies have solved that problem already?

https://www.meilisearch.com/

𝗔𝗱𝗱𝗶𝘁𝗶𝗼𝗻𝗮𝗹 𝗜𝗻𝘀𝗶𝗴𝗵𝘁𝘀 𝗳𝗿𝗼𝗺 𝗧𝗵𝗼𝗺𝗮𝘀:

* The importance of the team's health in building the product lies in focusing on creating something bigger than yourself.

* How an open-source model fosters community-driven growth and accessibility in technology.

* Insights on scaling a company effectively while maintaining a focus on developer experience.

Actionable Takeaways

Table of contents

01:46 The Myth of the Lone Genius

03:01 Building a Company: Team Dynamics and Realizations

07:03 Journey to Open Source Search API

09:23 Developer Experience and API Design

20:05 The Role of AI in Development

23:14 Challenges and Future of AI in Development

31:18 Final Thoughts and Contact Information

1. Embrace the Power of Teamwork

"How can we build, as a team, something bigger than the sum of us?"

Thomas Payet

Thomas emphasized that his goal with building a company is to make something that can outlast the original founding team. Success is multiple generations of teams that continue to work on the business that the founding team initially started.

A successful company typically involves a founder willing to make something bigger than themselves and focus their efforts on recruiting, retaining, and building a high-performing culture of individuals who can work together in the same direction.

Takeaway: For me, it's realizing that you are most impactful when everybody on the team is doing their best work.

It may be easy to play hero ball and fill in the gaps in a start-up, but truly successful companies with thousands of employees require operational and management skills to support their culture.

It makes me think about Jamie Tartt in the Apple TV show “Ted Lasso”. At the start of the show, Jamie was a talented, young player who didn't see himself as part of the team, but thought that his contributions were the sole reason they won games. If you haven't seen the show, I recommend watching it. I believe it has many parallels with professional corporate life.

You could be a rock star individual contributor, but until you learn how to play your role in the larger team, it doesn't matter how many goals you score. If the team itself isn't winning, then your stats don't matter.

4. Cultivate a Developer-Friendly Environment

"You want developers to be impressed and feel that they can be powerful using your tool…

…So you can configure the search API for example, you can, push, fake data into MeiliSearch’s search."

Thomas Payet

Thomas emphasized the importance of designing APIs that are not only functional but also a pleasure to use. A good user experience in APIs can significantly improve developer productivity and adoption rates.

MeiliSearch is a developer tool, but the same lesson applies to any customer using your software. You have to make it feel like they're putting on the Iron Man suit, and you're augmenting their ability to do their job.

Takeaway: Specifically for the developer experience, if your Saas business is infrastructure and technology that devs can implement into their products, making sure that they have a great experience to quickly test out and play around with your APIs, be it through documentation or interactive demos on your documentation website, will go a long way in increasing conversions and usage of your API tool.

3. Democratizing Technology Through Open Source

"We did not realize how powerful it could be to make it open source."

Thomas Payet

Going open source wasn't just a technical decision but a strategic move to make innovation accessible.

Takeaway: Allowing developers worldwide to access and contribute to the platform accelerates growth and engagement. For me, when creating an infrastructure product, like a search API, and your primary customer is a developer, allowing them to contribute to the codebase is a great marketing strategy.

Listen to the full episode to gain all the context and additional insights not included in this summary.

Connect with Thomas on Linkedin.

Listen now on Apple and Spotify.

Cheers,

Caden Damiano

Today’s podcast guest is Marcelo Calbucci, the author of "The PRFAQ Framework."

Listen now on Apple and Spotify

Like many product people, I've read "Working Backwards," "The Everything Store," and even attempted to write strategy narratives using the Press Release-Frequently Asked Questions (PRFAQ) Framework to capture lightning in a bottle like Amazon without much success. Before this interview, I thought you could only do PRFAQs if you were at a company like Amazon.

Marcelo is a seasoned tech leader with over 25 years of product leadership experience in major companies like Microsoft and Amazon. Marcelo has led engineering, product, UX, and data teams, drawing from his rich background to discuss the intricacies of Amazon’s Press Release and Frequently Asked Questions (PRFAQ) writing framework and how it can be adapted beyond its Amazon Culture.Marcelo noticed my story throughout the industry. Although books discuss Amazon's strategic narrative process, none provide a tactical breakdown of implementing the framework or formating your PRFAQs to achieve the best results.

"The PRFAQ Framework" explores how the PRFAQ can be adapted for non-Amazon environments. It provides innovators a structured way to achieve groundbreaking goals without Jeff Bezos as their boss.

Exclusively for podcast listeners and newsletter subscribers, Marcelo has provided me with a link that offers a discount to get your own copy of the “PRFAQ framework.” Get a 20% discount on the PDF Edition with the code CADEN20 on www.theprfaq.com/buy"

Connect with Marcelo on LinkedIn

Actionable Takeaways

✅ The P-R-F-A-Q framework: A tool for innovation beyond Amazon.

✅ Emphasizing the power of writing to drive critical thinking and innovation.

✅ Recognizing the importance of testing assumptions and hypotheses thoroughly.

Time Stamps

02:10 Marcelo's Journey: From Small Startups to Big Tech

05:50 Adapting Amazon's Written Narrative Framework for Everyone to Use

11:34 The Power of Writing for Problem Solving

15:10 Using Big Ideas in Small Businesses

20:22 Writing for Smart Decisions

28:06 Fixing Mistakes Through Practice

32:44 Making a Strong Innovation Culture

36:18 Deciding Which Tech Projects Are Valuable

41:10 Final Thoughts and How to Connect with Marcelo

The P-R-F-A-Q Framework: A Tool for Innovation Beyond Amazon

"The PRFAQ framework is meant to encourage deep, strategic thinking about potential innovations, helping to filter out what might not work early in the process."

—Marcelo Calbucci

Marcelo Calbucci's framework transforms how teams develop ideas and make strategic decisions. A PRFAQ is a 4-6 page narrative document that helps you think critically, articulate clearly, and inspire action.

Structure Basics

The document includes a one-page Press Release (written as if your future product exists today), followed by Customer FAQs and Internal FAQs. This structure forces clarity about who your customer is, what problem you're solving, and how you'll deliver value.

Writing Approach

Write with precision. Replace vague terms like "many customers" with specific numbers. Use active voice. Avoid jargon and unexplained acronyms. Present concrete data instead of generalizations. This clarity builds trust and reveals gaps in your thinking.

Collaboration Tips

Designate one PRFAQ owner who controls the document, but gather input from diverse perspectives. Hold structured review sessions with built-in silent reading time. Listen to feedback with an open mind - you're seeking truth, not validation.

What Makes It Work

The PRFAQ helps you discover what you don't know. By writing about a future state in the present tense, you identify assumptions that need testing. The document evolves through iterations, becoming stronger as more perspectives shape it.

The power of this method isn't just in the finished document it's in how the process transforms your thinking and aligns your team around a shared vision worth pursuing.

Takeaway: The framework helps innovators articulate clear, strategic objectives, enabling thorough pre-execution evaluation, which is crucial for decision-making. It's important that there isn't a documented author in the document. The goal isn't to take credit but to seek truth through using this collaborative artifact as a framework.

Emphasizing the Power of Writing to Drive Critical Thinking and Innovation

"Writing helps in thinking critically and articulating ideas more clearly. It's a powerful exercise to drive innovation."

—Marcelo Calbucci

Marcelo discusses the three superpowers of writing: it forces critical thinking, improves articulation, and inspires collaboration. Unlike slide decks, which often rely on visuals, narratives push you to engage deeply with your concepts, offering a clear understanding and direction.

Takeaway: Writing should be an integral part of strategic planning as it refines thinking and strengthens the clarity of your ideas. Writing also unlocks what Daniel Kahneman calls "slow thinking," which forces your brain to stress every articulated idea. This is critical for big strategic bets—you don't want to be spending millions of dollars on assumptions and biases.

Recognizing the Importance of Testing Assumptions and Hypotheses Thoroughly

"Most P-R-F-A-Q efforts lead to a decision not to proceed, which is a valuable outcome in itself."

—Marcelo Calbucci

In exploring the P-R-F-A-Q process, Marcelo reveals that most efforts conclude with a “no-go” decision. This rigorous scrutiny is intended to refine ideas by eliminating those that do not stand up to thorough investigation.

Takeaway: Resilience in product management and innovation often comes from recognizing when not to proceed with a project, saving resources, and aligning focus on more promising opportunities.

Listen to the full episode to discover how to leverage narrative-based planning tools to enhance your strategic impact. Then, use the link below to get your copy of Marcelo's book. I read it before releasing this episode, and it's been highly influential on my personal writing style.

Connect with Marcelo on LinkedIn

Listen now on Apple and Spotify

Exclusively for podcast listeners and newsletter subscribers, Marcelo has provided me with a link that offers a discount to get your own copy of the “PRFAQ framework.” Get a 20% discount on the PDF Edition with the code CADEN20 on www.theprfaq.com/buy"

Transitioning from a corporate film executive to a career coach, John has spent over a decade sharing insights and strategies to help individuals better uniquely position themselves, curate their messaging, and land roles tailored to their unique skills and strengths.

He also helps individuals transition into a different career track, and in this episode, we discuss how to make a successful career transition.

His unique approach draws heavily on entertainment industry metaphors, which I've been talking about for a while as a great analogy of a career in tech, where a lot of success comes from leveraging your relationships.

You can connect with John on LinkedIn or visit his website at johntarnoff.com

Listen now on Apple or Spotify

Time Stamps

02:00 Networking and Career Transitions

12:30 The Role of LinkedIn in Modern Careers

23:15 Strategies for Standing Out in Job Interviews

32:40 Building Relationships and Thought Leadership

40:05 Embracing AI and Originality in Your Work

51:45 Final Thoughts and Career Development Advice

Actionable Takeaways

Networking and Career Transitions: Handling a Career Pivot

"What I've discovered is that the rest of the world has become like entertainment, where it is all about networking."

—John Tarnoff

John highlights that navigating through career ups and downs requires a strong network.

This now applies to all industries, not just entertainment. The message is to avoid being a "supplicant" in the job market and to leverage your strengths comprehensively on platforms like LinkedIn.

Takeaway: One thing I've observed in the age of AI is that data is no longer the oil; it's a judgment. Very soon, knowing a skill isn't going to be enough to hold down a job. Your reputation and trust with the people you work with will provide you with more career opportunities.

Resumes are Irrelevant: How to Use LinkedIn in a Modern Career

"My philosophy is that you have to make LinkedIn your master resume."

—John Tarnoff

John stresses the importance of crafting a LinkedIn profile that isn't just a digital copy of your resume.

Instead, it should serve as a master document showcasing who you are, your values, and the unique qualities you bring to the table.

Takeaway: All strategy is just segmentation and positioning. Your LinkedIn should filter away potential job prospects by highlighting your values.

If you're not attracting work through an authentic LinkedIn portfolio, you might want to reconsider the market segment you're targeting for your LinkedIn profile.

Strategies for Standing Out in Job Interviews

"The goal is to present an option, a set of choices, and not necessarily to get the part."

—John Tarnoff

The podcast explores the parallel between auditions for actors and job interviews for professionals. It’s about participating in a conversation to find mutual fit rather than desperately vying for a role.

Takeaway: Use interviews as opportunities to demonstrate how you can help solve the potential employer's problems, showcasing your unique perspective.

Building Relationships and Thought Leadership

"It's not just having a good LinkedIn. You need to demonstrate thought leadership."

—John Tarnoff

Developing a personal brand and thought leadership through consistent engagement is pivotal. It’s about positioning yourself as a professional with a unique point of view and using platforms to share insights that reflect your expertise and interests.

Takeaway: My first big job at a college came from using this strategy: Engage regularly on platforms like LinkedIn. Contribute thoughtfully to discussions, publish content, and participate in community events to build your professional reputation.

Embracing AI and Originality in Your Work

"You have to double down on being more original, nuanced, smarter, more relevant."

—John Tarnoff

As AI becomes more integrated into professional landscapes, John discusses the importance of maintaining authenticity in your outputs and interactions. Use AI as a tool, but don’t let it overshadow your unique contributions and voice.

Takeaway: Authenticity in your work will differentiate you in a landscape where AI can generate content at scale. Strive for original thought and genuine human connection.

Thanks again for reading. If you liked this episode, connect with John on LinkedIn or visit his website at johntarnoff.com

Listen to the full episode to hear the great behind-the-scenes stories behind these takeaways in the context that John added to make this advice more valuable.

Listen now on Apple or Spotify

Have a good one!-Caden

AI isn't going to take your job, people using AI will take your job.

That's because disruptive technology redefines a task and workflow; it doesn't replace the responsibility behind the task in the first place.

Adapting and upskilling is how you stay relevant when people are looking for folks to manage and design their products. In this episode, I discussed agentic AI with Anshul Gupta, a Product leader at Ema Unlimited. At Ema, he spearheads the development of cutting-edge agentic AI technologies to power the universal AI employee. With over a decade of experience in technology leadership, Anshul has served as Director of Product at Greenlight and as Product Lead for Google Nest and other Google teams. He holds an MBA from Yale University and earned his bachelor’s degree from the Indian Institute of Technology Delhi.

Anshul shared his experiences and insights into leveraging AI to drive business efficiency and innovation. He discussed the evolution of SaaS tools, the integration of AI agents, and the shift towards more outcome-based pricing models.

Connect with Anshul on LinkedIn.

Listen now on Apple and Spotify.

Time Stamps

03:05 Anshul’s Career Path: From Lehman Brothers to Ema

10:45 Leveraging AI for Business Processes at Ema

17:30 The Challenges and Opportunities in SaaS Evolution

25:15 Impact of AI on Customer Support and Efficiency

30:39 The Future of Enterprise Tools with Agentic AI

35:00 Building Trust in Automation with Human in the Loop

42:48 Cost-Effectiveness in AI-Driven Workflows

47:22 Cultivating Innovation in AI Product Development

Actionable Takeaways

✅ Embracing AI for Business Process Automation.

✅ Understanding SaaS Evolution and AI Integration.

✅ The Power of Outcome-Based Pricing Models.

Embracing AI for Business Process Automation

"Agentic AI is not about replacing jobs, but augmenting capacity."

—Anshul Gupta

Anshul emphasizes AI's role in enhancing productivity amidst reducing team sizes and scarce human resources in industries like healthcare. AI not only aids in customer support but also facilitates complex tasks, allowing employees to focus on high-impact work.

Takeaway: Utilize AI to free up valuable human resources for more strategic tasks and optimize operations across various sectors.

Understanding SaaS Evolution and AI Integration

"AI agents can help bridge the gaps between different tools, eliminating data silos."

—Anshul Gupta

The proliferation of SaaS tools has led to operational inefficiencies due to a lack of integration. Anshul's work at Ema focuses on using AI agents to connect disparate tools, improving workflow automation, and reducing reliance on human intermediaries.

Takeaway: Integrate AI agents to streamline processes and enhance business efficiency by eliminating data silos.

The Power of Outcome-Based Pricing Models

"The landscape of SaaS will change with more companies moving towards outcome-based pricing."

—Anshul Gupta

Anshul explains how Ema and similarly forward-thinking companies are shifting from traditional per-seat software licensing models to pricing based on task outcomes, offering more financial alignment and incentives for businesses.

Takeaway: Consider adopting outcome-based pricing models to better align software costs with value and return on investment.

Listen to the full episode to get all the insights and learn how AI is reshaping the future of business automation.

Connect with Anshul on LinkedIn.

Listen now on Apple and Spotify.

In this episode, we’re hanging out with Sagar Batchu, the guy behind Speakeasy, who’s doing groundbreaking stuff in the world of APIs and AI. Sagar’s journey from physics to tech is packed with insights into how we can all use APIs and AI to make life a little easier for product teams.

Connect with Sagar on Linkedin.

Listen now on Apple and Spotify

With his background in developer tools from his time at LiveRamp, Sagar knows the drill for streamlining processes.

His company, Speakeasy, aims to make APIs more accessible and user-friendly, removing the headache from the tech side. I was struck by how he sees APIs and AI weaving together to create super straightforward solutions, and I’m stoked to share some of these ideas with you.

Actionable Takeaways

Shoot for the 80/20 Win:

"You can never perfectly solve a customer's problem... What you can do is build something that's amazing in the 80/20, right? Help 80 percent of users do things really well." -Sagar Batchu

Instead of trying to be all things to everyone, focus on delivering great experiences for the majority. It’s about hitting the sweet spot between effort and impact. Robust API development helps you build this 80% foundational use case for tech products.

APIs: Your Secret Weapon:

"An API is like a super powerful developer, right? You're delegating some massive amount of work to a single, single URL, single call." -Sagar Batchu

Think of APIs as levers that handle the heavy lifting, letting you zero in on what counts: delivering on customer promises.

Let AI Bridge the Gap:

"We're getting to the next level, all you need is natural language.  Tomorrow is here already…Pull up your chat window of your favorite AI product, the LLM, and say, find me the best fights to Europe” -Sagar Batchu

Large language models are making it even easier for non-technical people to leverage the power of APIs.

ChatGPT and similar interfaces provide an easy way to interact with APIs using natural language. They can query specific APIs, such as those for flight information or Google search results. This capability allows you to ask ChatGPT to guide you through setting up an API for your product, potentially saving development time.

Thanks again for reading this week’s newsletter.

If you’re curious about diving deeper, listen to the full episode. And learn more about Speakeasy here: www.speakeasy.com

Connect with Sagar on Linkedin.

Listen now on Apple and Spotify

Cheers,

Caden Damiano

In the latest episode of Way of Product, I had the pleasure of chatting with Rob Walling, a serial SaaS entrepreneur, author, and SaaS investor at Tinyseed. Rob spends most of his time teaching people how to build million-dollar startups without venture capital. He also helps SaaS founders build incredible businesses. Rob has started six companies, written five books, Invested in 200+ startups, and has 15M+ podcast downloads on his podcast, Startups for the Rest of Us.Rob challenges the conventional narrative that startups must raise funding, instead advocating for bootstrapping as a viable path to success. He shares his 'one-nine ninety' rule, arguing that only a small percentage of startups should pursue venture capital. Rob draws on his journey as a successful tech entrepreneur who bootstrapped multiple companies, including Drip, which he sold in 2016.Connect with Rob on Linkedin.

Listen now on Apple and Spotify.

Actionable Takeaways

✅ Challenging the startup venture funding narrative.

✅ Profit over growth—choose freedom.

✅ Building resilience through hard decisions and luck.Time Stamps02:57 Real Estate vs. Software: Finding the Right Path

05:39 The Value of Bootstrapping

10:37 The Role of Developers in Startups

17:29 The Success of Drip

19:25 Making Hard Decisions with Incomplete Information

19:36 Launching and Finding Product-Market Fit

19:58 The Importance of Timing and Luck

22:39 Building an Audience and Brand

24:00 The Role of Hard Work, Luck, and Skill

27:28 Challenges in Product Management

33:22 The Value of Ownership and Decision Making

35:12 Final Thoughts and How to Connect

Challenging the Startup Funding Narrative

"There's this b******t narrative that everybody who does a startup has to raise funding. It's just not true."

—Rob Walling

Rob argues that it’s a myth that startups must always raise funding. His "one nine 90" rule suggests that only 1% of startups should consider raising venture capital while the majority could bootstrap successfully.

Takeaway: Evaluate if external funding aligns with your startup goals or if bootstrapping might give you more freedom and control.

Profit Over Growth—Choose Freedom

"I haven't done anything for the money. I've done it all for the freedom."

—Rob Walling

Rob shared personal experiences, highlighting his journey from real estate investing to SaaS entrepreneurship. He emphasized that his drive was not to amass wealth but to gain control over his projects and time. Real estate investing might be good for building assets and wealth, but it is terrible when you want freedom and choice in how you spend your time.

Takeaway: Focus on building businesses that align with your values and lifestyle. SaaS is a great asset class if you value freedom and autonomy. 

An interesting takeaway is that you only need $4M in liquid assets when you retire to live a comfortable life and not have to work again. The game isn't to amass as much money as possible; it's to figure out what enough is for you and develop that muscle of knowing when you could stop.

Building Resilience through Hard Decisions and Luck

"As a founder, your job is to make hard decisions with incomplete information."

—Rob Walling

Walling asserts that hard work, luck, and skill are vital to entrepreneurial success.

Success isn't guaranteed. That's the trade-off of going into the entrepreneurial journey. Considering that there's luck involved allows you to start making decisions that put you in a position to be lucky.

Jason Fried, co-founder of Basecamp, told Rob that luck and timing were essential to the company's success. Given the competitive market, Launching Basecamp now would be more difficult.

Takeaway: Accept that uncertainty is part of the journey. Use it to build resilience and trust in your decision-making abilities. Strategy is just positioning and segmentation. If you can get positioning and segmentation right (the “skill” aspect of success), you might have a better chance of being lucky and winning in that market segment. 

Conclusion

Rob Walling’s journey offers a fresh perspective on entrepreneurship, emphasizing freedom, autonomy, and the importance of resilience over long time horizons.

Listen to the full episode to get all the context and stories behind these actionable takeaways.

Thanks for reading The Way of Product! Subscribe for free to receive new posts and support my work.

Listen now on Apple and Spotify.

Key Mistakes in SAAS Pricing

Bill framed a crucial premise: Pricing is dynamic and rooted in market changes and customer perceptions. He pointed out the fear many have of changing pricing models due to confidence issues. Bill stresses that pricing isn't static, and it’s essential to periodically review and adjust it to reflect the growing value of your product.

* Misunderstanding Market Dynamics

* Pricing is a Negotiation

* Table-stakes features aren’t enough to justify the purchase

* Founders Delegating Sales Calls Too Soon

* Not Willing to “Hill Climb”

Time Stamps

00:00 Introduction to Pricing Challenges

03:07 Deep Dive into SaaS Pricing

05:54 Common Pricing Mistakes and Anti-Patterns

08:55 Understanding Customer Value and Competitor Pricing

13:07 Monetization Strategies and Feature Valuation

16:55 Pre-Sales and Customer Engagement

18:07 The Importance of Customer Surveys

18:46 Leveraging Data for Product Development

20:22 Insights from MIT Sloan Executive Education

20:47 Understanding Pricing Strategies

22:58 The Role of Product Managers in Pricing

27:27 Founder-Led Sales and Founder-Led Product Management

29:25 Capturing Market Demand

32:04 The Multifaceted Role of Product Managers

36:30 Final Thoughts and How to Connect

1. Misunderstanding Market Dynamics

According to Bill, here’s what often goes awry:

* Guessing the Price: Too many businesses set prices based on intuition rather than data. Bill argues the right question is not "How much should I charge?" but rather, "How do I charge?"

* Ignoring Competitors’ Shortcomings: Copying competitors can be misleading. Understanding your unique value—and then pricing for that, rather than mimicking competitor pricing blindly is essential.

2. Pricing is a Negotiation

"People just don't change their pricing regularly enough… I think one of the biggest mistakes is that people just don't change their pricing regularly enough. Like they don't, they don't look at it. They don't, you know, raise the price. People are scared to death to raise prices or even change their model…

Takeaway: Approach pricing like a negotiation. Keep making higher-priced offers, then regularly iterate your pricing strategy as your product and market evolve. This experimental mindset will help you capture actual product value over time.

3. Table-stakes features aren’t enough to justify the purchase

Understanding and articulating your product’s differentiated value is paramount.

"Understanding what value you're bringing to your customer is probably the most important thing you can do……pricing is about confidence… what value you're bringing to your customer is the most important thing you can do. It's constantly changing because the market's changing. People's perceptions are changing…

… Why do you exist? You have the same price and claim to solve the same problem. What's the point?”

Takeaway: Consider what's valuable to your customers by examining what you can do that a competitor cannot. Reflect on how markets and perceptions shift, and stay proactive in aligning your pricing. In many ways, pricing is about optics rather than being the most comprehensive product.

3. Founders Delegating Sales Calls Too Soon

Bill’s journey from software development to founding Pace Pricing underscores the importance of adaptability. He highlights how his ventures shaped his understanding of pricing and product value, with each role honing his approach to monetization.

Founder-Led Sales: Bill emphasizes that founders typically excel at leading sales and product decisions in the early stages because they have an innate understanding and passion for their creations.

“I’m a big fan of founder-led sales, especially at the beginning. I made the mistake of hiring a sales guy a few months after launching our product, and it was a disaster. He relocated, and we were still experimenting. It didn’t work.

Building a Confident Proposition: Bill’s stories of creating a product led to monetizing solutions that genuinely solved customer problems—his narrative serves as a roadmap for budding entrepreneurs or those in product management.

The founding team should run product because they can make necessary decisions. Product managers can’t do it in the same way; they may feel obligated to protect their jobs. As a founder, you can make bold decisions that might not seem sensible at the moment, but you believe they are the right moves to steer the company.”

4. Not Willing to “Hill Climb”

One way to figure out willingness to pay is to use a simple technique called hill climbing. Set your price for a small product and, every five to ten sales, increase the price. Keep doing this until you receive pushback, with around 20 to 30 percent of people saying no. At that point, you may have identified the maximum willingness to pay.

Takeaway: Bill highlights the essential interplay between product and monetization, a concept every product team should integrate into its workflow.

If you'd like to learn more about pricing strategies directly from Bill, connect with him on LinkedIn and watch his informative pricing page tear-down videos for more hands-on insights.

Also, we only scratched the surface of the value of this episode. Make sure to listen to the full interview when you get a chance.

Listen now on Apple and Spotify.

Cheers!

Caden Damiano

Most businesses think innovation is budget-bound. But it's not.

In this episode, I talk about how to stay ahead of the curve with AI with Michael Todasco.At PayPal, he led a product innovation practice, exploring cutting-edge technologies long before they became mainstream. Recently, he's turned his focus to AI, becoming a key voice in the space through writing and advising.Connect with Mike on Linkedin.

Listen now on Apple and Spotify.

Actionable Takeaways

1. "If you're not failing, then you're not trying hard enough."

Understanding that failure is just part of the process is crucial in any innovative field. Mike emphasizes that his most memorable and educational career experiences stem from failures, which provide valuable learning opportunities that successes rarely do.

Takeaway: Embrace failure. Each setback offers lessons that drive growth and lead to more significant innovations.

2. "All ideas are born from other things."

True Innovation Occurs When Ideas Intersect:

Mike reminds us that unique ideas rarely emerge from a single source. Most innovations result from combining existing ideas, contexts, and inspirations. This concept reflects how diverse experiences and knowledge contribute to breakthrough innovations.

Takeaway: Encourage cross-industry learning and collaboration. Draw inspiration from unrelated fields to spark creativity.

3."Find where there is passion and you will learn so much from that."

Mike believes that innovating successfully relies on passion—it's the force that sustains and inspires us in our work.

It's not just about loving your project; it's about loving the problem enough to pursue a solution relentlessly.

Takeaway: Cultivate and nurture your passion. Let it guide your efforts and keep you motivated through challenges.

4. "Your future as a product manager is to be a director of AI Agents."

With AI's capabilities expanding rapidly, professionals must become directors of these technological tools.

The responsibility lies in leveraging AI to execute mundane tasks efficiently, freeing time to focus on strategic and creative aspects of their roles.

Takeaway: Embrace AI as an ally that can augment your capabilities, not replace them. Continuously explore how it can elevate your role and responsibilities.

5. "Literally give 20 bucks to Anthropic, buy Claude, give 20 bucks to OpenAI, buy ChatGPT."

Get ahead of the curve by starting to play with AI today.

Mike highlights the accessibility of AI tools and encourages everyone to dive in. He believes that hands-on experimentation is the best way to understand the potential and limitations of AI.

Takeaway: Begin experimenting with AI tools regardless of your technical background. Test their capabilities and see how they can integrate into your workflow.

Don't miss out on hearing Mike's detailed tactics and insights firsthand by listening to the full episode.

Cheers,

Caden Damiano

How does an AI-powered business make money? What do they do differently?

In this episode, Elizabeth Samara-Rubio from SiMa.ai, gives us a practical guide to the “Business of AI” and the implications of integrating AI into real-world processes like manufacturing and agriculture.

Her experience spans significant roles, including leading over 20 AI services at AWS and pioneering efforts in generative AI. Elizabeth's career trajectory also includes serving as Managing Director at Accenture, where she spearheaded growth initiatives in cutting-edge technology sectors—experiences that established her deep-seated expertise in bringing technological advancements to traditional business sectors.I was blown away by how deep Elizabeth was willing to go in this interview. I learned so much about the practical logistics of implementing AI into a business, and you won't hear this level of practicality in most AI interviews.

Actionable Takeaways

Table of Contents

1. Understand AI's Role in Business: “How do you make money?”

2. Empower Your Ecosystem: “Intro to Edge Machine Learning Systems”

3. Embrace the Maturity Curve: “The Required Time Horizon to Implement AI”

4. Responsibility in AI Implementations: “Are you willing to invest and nurture this for at least 10 years?”

Understand AI's Role in Business

"AI is not just a shortcut. It takes time and maturity to understand where it adds value." Elizabeth Samara-Rubio

By viewing AI as a long-term investment rather than an instant solution, businesses can gradually integrate AI to improve operations.

Takeaway: Consider AI a marriage; you're in it for the long haul. Evaluate where it can add value to transform business processes over time.

Empower Your Ecosystem

"We don't just say, 'Come back when you're ready.' We're here to help build your ecosystem, You can do the most great things in the world, but if you don't have a data pipeline, you don't have a governance structure, you don't have the skill set…

You can talk about it.  You can proof of concept it over and over again, but you're not going… to scale."

Elizabeth Samara-Rubio

SiMa.ai develops AI computing hardware to be embedded into their client's systems. So that traditional businesses can start building their AI capabilities in-house.

Most traditional businesses, like manufacturers and agriculture, don't have the talent or capabilities to develop their own AI from scratch. More and more, you have to consider partnering with companies that can grow with you and give you the base capabilities to develop AI in business.

Takeaway: Integrating AI into a traditional business is as much a hardware problem as an AI problem. So, investing in strategic partnerships to empower your tech ecosystem will future-proof your AI implementations.

Embrace the Maturity Curve

“We don't just say, 'Come back when you're ready.' We're here to help build your ecosystem."

Elizabeth Samara-Rubio

The most significant gap preventing traditional industries from embracing new AI tech is hiring in-house talent. It's difficult to get a Silicon Valley engineer to want to work for a traditional manufacturing business in the Midwest. Companies like SiMa.ai provide services to integrate their expertise and hardware so their clients never have to develop robust AI talent in-house.

Elizabeth notes the stages businesses undergo with AI integration, from increasing throughput to enhancing productivity, and the role AI infrastructure businesses will play moving forward.

Takeaway: Map out the stages of AI integration in your business. Start small and scale as your team's maturity and understanding of technology grow.

Responsibility in AI Implementations

"An AI model demands continuous monitoring and retraining;

Responsibility isn't just about deployment; it's about ensuring models operate reliably and ethically throughout their lifecycle.”

Elizabeth Samara-Rubio

Takeaway: Develop a robust framework to manage AI models, monitor their performance, and update them as required.

Listen to the full episode to get more details on-premises AI computer hardware and the in-depth technical details of how you get AI into manufacturing and agriculture.

Cheers!

Caden Damiano

Connect with Anuj on Linkedin.

Listen now on Apple and Spotify.

Modern API strategies for enterprise SAAS

It's easier to take the time and money to make something custom to your business.

But this isn't always cost-effective for repeatable tasks like integrating with CRMs, HR systems, and other business-critical processes that have established solutions.

From Anuj's perspective, interpersonal skills and good team stewardship are the starting points of a good API roadmap. These skills play a significant role in bringing out the best in people to execute something as tricky as API integration development.

Product managers, engineering leaders, and even designers must be aware of services like Merge to drive scalable and quick-to-market API integrations to HR systems and CRMs your customers need to use your product effectively. Coding and integration into Salesforce from scratch is a problem that has already been solved and could easily be a buy solution for your product.

Making the switch to Product Management

In past episodes, I’ve been critical of the product management job family, which made me very reluctant to follow mentorship feedback that I should switch from design to product management.

He provided some perspectives on my critique that evoked empathy regarding the role of product management. So, Anuj, if you are reading this, Thank you for your patience and gracefulness in addressing my concerns about this career move; this conversation was pivotal in finally making the switch earlier last year.

Actionable Takeaways

* The Power of Hospitality in Unblocking Success. The Virtue of Consideration.

* Influence Without Authority: The One Thing Most PM’s Fail To Do—and Why

* Balancing Professional and Personal Growth. How “Getting a Life” is a Growth Hack.

The power of hospitality in unblocking success.

"As PMs, in many ways, we are in the hospitality industry. There are different customers we serve."

– Anuj Jhunjhunwala

Action Tip: What does putting yourself in other people's shoes mean?

It first requires you to understand your perspective. Understand why you feel a certain way about a direction.Only then can you put yourself in someone else's shoes and see how their perspective has led them to a different conclusion than yours. Finally, asking clarifying questions to reconcile your perspective and their perspective is what empathy is.

Influence Without Authority: The One Thing Most PM’s Fail to Do.

Every company needs someone who is talking to customers and understanding their pain points and translating that into something actionable."

– Anuj Jhunjhunwala

Action Tip: Work on building trust and relationships. Trust is the only currency product managers can effectively deploy in a position where they cannot exercise direct authority over business operations.Influence through inspiration rather than assertion, and create a collaborative environment where ideas can thrive.In your role as a product manager, you may not always have formal authority, yet you possess the potential to guide your team. Anuj reminded me that influence comes from inspiring and convincing others, skills he honed at work and home as a parent.

Balancing Professional and Personal Growth

"Paradoxically, having less time means I need to be more intentional and productive with the time I have."

– Anuj Jhunjhunwala

Action Tip: Balancing a high-demand role with a personal life and family can be daunting. It's led to many people delaying things like family and hobbies to build their careers.

Paradoxically, not broadening your perspectives through things like having children, getting involved in the arts, and having a non-work hobby can make you less effective over the course of your career through Parkinson's law. More time leads to less urgency. Less urgency leads to lazy thinking. Having too much time leads to you filling it with work—effort that might not have needed to happen if you had some health constraints to prevent it from happening. Anuj's experiences as a young parent show the paradoxical benefit of having people outside of work who rely on him to be present and with them.

It forces you to prioritize what matters most and establish clear boundaries.

Now that you have a fixed amount of time to complete work, you will be forced to understand the true meaning of prioritization. You will do only the one thing that makes the most sense right now and de-prioritize everything else.

Cheers!

Caden Damiano

With self-driving cars from Tesla, AutoPay, and AutoSaving, as well as same-day shipments and grocery delivery, we expect our technology to think for us, not the other way around. Historically, large legacy companies have failed to make this a priority, thinking that traditional operational models and hand-holding SOPs are enough to retain the business of millennials and Gen-Z.

In this episode, we discuss how American Express has reinvented itself over the past two centuries. It started as a freight forwarding company and continued to innovate with traveler's checks, credit cards, and, eventually, a strong digital technology experience. Ryan joined American Express in its next iteration of doubling down on its mobile app experience, modernizing its credit card application offering to utilize all the data available to eliminate the misleading “pre-qualification—all to cater to the new rising market of Gen Z through their “Apply with Confidence” Product.

Actionable Takeaways

✅ Redefining Product Management

"My job is not to be right. My job is to get it right…and a lot of the product managers (are) so focused on proving their value and how good they are that they can't afford to be wrong.

But the longer you go in your career, you find out that being right—out of the gate is probably the worst outcome that you can drive." - Ryan Calliet

Pro Tip: Many failed products were based on an influential individual trying to sound smart at the cost of doing the legwork required to find the right solution and get the execution right.

Even if Ryan is wrong, the first couple of attempts and the lessons learned in those failures usually give the insights needed to get it right the next time.

✅ Building Trust through Being Considerate in the Design Process

"Acquisition is your first experience with a brand. We want to make sure we get off on the right foot, build a trusting relationship and that you come back to us as you grow and evolve over time." - Ryan Calliet

Pro-Tip: Ryan's user-centered design fosters transparency and trust, essential for customer relationships amid skepticism. After months of effort, their pre-qualification experience failed because customers lacked trust in it, viewing it as not a guarantee of approval from Gen Z, new to the credit card market. The team refined their plans to ensure successful approval outcomes. This challenging process required collaboration with legal, compliance, and credit bureaus. Ultimately, it resulted in strong adoption among Gen Z.

✅ Taking Calculated Risks

"Risk-taking is a part of this job. You can't know how people will react to a product until it’s out there. (Counting on evidence) “Beyond a reasonable doubt” is great because you have to make that judgment." - Ryan Calliet

Pro-tip: Being data-driven 100% of the time isn't possible. Eventually, you have to make a judgment call. So, if you feel like you're at least 75 percent confident, which in the legal system is “beyond a reasonable doubt,” it's worth trying out the idea.

If you're less than 75% and closer to 50%—or less than 50%, maybe it's time to take the idea back to the drawing board and continue your research until you have more confidence in another direction.

Connect with Dean on LinkedIn

In this episode, we want to discuss Dean's notable journey from indy wordpress developer to leading product strategy at ClickUp and explore his unique, tailored fit role at the company.

We'll also take a closer look at the company's community engagement and its impact on his current position. He shares how ClickUp tackles being an all-in-one platform without sacrificing quality and how they're using AI to make work smoother.

We also chat about leading through influence—something Dean does masterfully.

If you're into tech, product strategy, or just love a good career pivot story, give it a listen!Time Stamps

01:43 Joining ClickUp: The Early Days

18:35 From Music Side Hustles to Product Strategy

24:52 The Origin Story of ClickUp

33:35 Senior Leadership at ClickUp

34:01 ClickUp's Contrarian Success

35:13 Challenges and Innovations in All-in-One Apps

38:25 Team Structure and Collaboration

45:41 The Role of Obsession in Product Management

54:16 Building ClickUp's Chat Tool to Replace Slack

I have DOUBLE the takeaways. There is so much good stuff here.

Obsession as a Catalyst for Success

Dean Phillips' path to success embodies the power of obsession. From the early days when he was just a highly engaged user of ClickUp, his unwavering dedication and deep-seated curiosity drove him to evolve into a pivotal figure in the company's strategic direction.Dean's love for creating and improving products was evident when he first pitched an idea to ClickUp's CEO. His unique insights and passion were recognized, leading to an unexpected role offer.

"I sent it. I was like you should execute this. Please do this. The response was “this is amazing. Do you want to come and execute it with us?"-Dean Phillips

Actionable Takeaway: Let your obsession guide you. Find a problem you can't stop thinking about and immerse yourself in it. This level of engagement can be the difference between being good and becoming exceptional in your field.

The Role of Intuition in Product Management

Dean describes his journey into product management as unorthodox. He relied heavily on his intuition and creative instincts, often sketching his ideas and engaging deeply with designs processes. Despite lacking formal training in product management, Dean's ability to connect dots and foresee product pathways became his strongest asset.

"I kind of had that intuition. But I didn't realize how to do that when I first joined. I didn't realize that is what I have to do, if that makes sense."

-Dean Phillips

Actionable Takeaway: Trust your intuition. Even without extensive experience, your unique perspective and insights can introduce innovation. Don't shy away from presenting your ideas—you might offer the missing piece your team needs.

Strategic Innovation at ClickUp

Dean's role at ClickUp expanded as he took charge of aligning various product components within a cohesive strategic framework. His leadership was crucial in the development of ClickUp's integrated chat feature, which addresses the fragmented nature of workplace communications by bringing context and communication into one place.

"It's my role to oversee every single team, every single feature, and like stitch them all together and make sure that we're building with everything kind of coming together at the right time."

-Dean Phillips

Actionable Takeaway: Focus on integration. When developing strategies, ensure that your ideas foster collaboration and innovation across various components. Aligning different projects under a unified vision can significantly enhance overall productivity and user experience.

Embracing the “Super Individual Contributor” Role

An intriguing aspect of Dean's role at ClickUp is his position as a super individual contributor. He thrives on influencing without formal management authority, collaborating closely with diverse teams to drive innovation and achieve strategic goals.

"I'm a super IC. I'm not involved in the managerial side of things. That was by choice. I wanted to be deep into the weeds helping all the PMs and designers create things. I'm a creator."

-Dean Phillips

Actionable Takeaway: Embrace the super IC role by finding ways to contribute significantly without the need for direct reports. Influence and leadership can come through expertise and collaboration, rather than formal hierarchy.

Overcoming Challenges through Leadership

Dean acknowledges the challenges he faced as he transitioned into a leadership role, emphasizing the value of stakeholder management and influence without formal authority. This journey was not just about personal growth but also about fostering an environment where creativity and innovation could thrive.

" "It's my job to bring a vision together for each area that ties to the greater vision of ClickUp and where we want to go.We wanted to build a strategy which made everyone work together and we had checkpoints. A big part of how we build now with all these features is, we have different teams.

-Dean Phillips

Actionable Takeaway: Cultivate influence. Even without formal authority, you can lead by example and influence others through your work ethic and vision. Foster trust and communication within your team to drive collective progress.

Adaptability is Key in Product Strategy

"It was a big learning curve when I went to ClickUp. But once I had the title of product manager I latched onto that and dove right in to figure it all out." - Dean Phillips

Action Tip: Be open to learning and adapting in new roles. Embrace challenges and seek to quickly understand and integrate new knowledge to drive product strategy forward.

Developing Contextual Solutions for Product Development

"We built ClickUp chat for different kinds of people. We built it for people who love async communication and people who like async communication." - Dean Phillips

Action Tip: Tailor your product features to address varying user needs. By focusing on diverse use cases, you can create more inclusive solutions that improve user experience and engagement.

Here's the latest interview with Brendan Fortune, Director of Product Management at Customer.io.

Connect with Brendan on Linkedin.

Listen now on Apple and Spotify.

In it, he shares his journey and insights into building effective product management teams and when it’s time to hire the first product manager.

Brendan's Approach to Product Management:

Brendan Fortune emphasizes the necessity of creating teams with the right balance of skills and passions. He advocates for the triad model consisting of a product manager, product designer, and engineer to ensure all critical areas are covered, thereby mitigating risks and accelerating growth.

Actionable Takeaways

💪 Understanding the role of product managers and how it ties into leadership, particularly in startup environments.

🔥 The pitfalls of hiring product managers prematurely and how to determine the right timing based on product-market fit.

✌️ How customer behavior can inform product flywheels and lead to sustainable growth.

Risk Doesn't Need a Title

Brendan discusses how risk management should not be confined to a job title but should align with the right person. Leaning into team members' strengths often results in better outcomes.

"I think it's on display at every startup that I've worked at. You need to be flexible and figure out how you fit into the solution."

"Leaning into someone's skills and passions can lead to amazing outcomes, as the team reforms around that individual's idea."

Action Tip:Encourage flexibility within your team by aligning roles with individual strengths and passions rather than strictly defined job titles.

The Flywheel Concept When Deciding Team Topologies

Brendan talks about focusing on the flywheel—a sequence of customer actions and reactions—to streamline growth and optimize product management.

"The idea of having a clear sense of your product flywheel can guide product organization and help plan when to hire new team members."

Action Tip:Identify your product's core flywheel and ensure your team is structured to facilitate its natural progression.

Pitfalls of Early Product Management Hires

Hiring a product manager too soon can stall growth. Brendan suggests waiting until the financial metrics justify the hire, ideally outside VC funding.

"Can you economically support a salary for a good product manager? That's a good indicator of reaching product-market fit."

Action Tip:Evaluate whether your business has generated enough value to invest in a product management hire responsibly.

The Importance of Story:

Creating meaningful work often hinges on the story being told. Brendan highlights how product managers can foster excitement and drive within a team by crafting a compelling narrative.

"People want to do meaningful work and the best product manager helps make the work feel meaningful."

Action Tip:

Focus on the narrative that ties your team's work to broader company goals, fostering a shared sense of purpose and clarity.

Best,

Caden Damiano

caden@hey.com

I recently had a fantastic conversation with Tammy Alvarez (LinkedIn) on the podcast, and she really got me thinking about how we approach our careers. She is also the author of “Escaping the Career Trap,” a guide to taking charge of your career and getting excited about Monday mornings again. Get it on Amazon

Listen now on Apple and Spotify.

Tammy has been through the corporate grind on Wall Street and now runs the Career Winners Circle; they shared game-changing insights on how we can break free from the corporate rat race and really own our career paths, even if it’s in-house.

Here are some of my thoughts from this episode:

Actionable Takeaways

Table of Contents

✅ Failure is only a moment, not an identity

✅ Your personal brand is key to having career agency

✅ Be the CEO of your own career

✅ Build your power base, your personal board of directors

Failure is only a moment, not an identity.

Instead of tying everything to success or failure, she suggests viewing every career move as a chance to try new things and learn. It's all about experimenting, seeing what works, and tweaking your approach until you hit your stride.

"Too often we think we're either success, fail, pass, good, bad, black, white. Whereas when you do everything in your career, in your life, in your business, taking that experimental mindset, knowing that you're going to iterate."

-Tammy Alverez

Takeaway: Failure is only a moment, not an identity; if we define ourselves by our bad moments, we will never achieve mastery.

Mastery takes grit, resilience, and being willing to keep trying until you master your craft.

Your personal brand is key to having career agency

Even if you're not big into self-promotion, your reputation—or personal brand—is constantly being shaped. Tammy pointed out that if you’re not defining how people see you, someone else will. So, why not take charge?

"You always have a brand, whether you want one or not. And so who would you rather influence your brand, you or other people?"Tammy Alvarez

Takeaway: Think about the top three words you want people to associate with you. Make sure your actions at work reflect those qualities every day.

Be the CEO of Your Own Career

Tammy’s advice to treat your career like a business really hit home for me. Imagine you're the CEO of your own life: you set the goals, figure out the strategy, and pivot as needed to reach your aspirations. By taking ownership, you can align what you do with what truly excites you.

"Congratulations, you just got promoted because now you are the CEO of your career and you're the CEO of you incorporated."

Tammy Alverez

Takeaway: Start seeing yourself as the CEO of You, Inc., and make decisions that align with your personal and professional goals.

Every action you take raises or lowers your stock price and your market value. Act accordingly.

Build Your Power Base

Networking isn’t just about LinkedIn connections; it’s about nurturing real relationships with people who have your back. Tammy calls this your power base—the folks who will champion your ideas when you’re not in the room and help propel you forward.

"Who are your sponsors and who are the people who are saying good things in the room when you're not there?"

Tammy Alverez

Takeaway: Identify key allies both inside and outside your organization who can support your growth, and do the same for them.

In short, Tammy’s approach is all about empowerment—finding your voice, nurturing your strengths, and making bold decisions to get where you want to be. If you're itching to shake things up in your career, her insights could be just the push you need.

Catch the full episode if you haven’t already, and feel free to share your thoughts on how you're taking control of your career. Happy exploring!

I'm excited to share my latest conversation with Trevor Nielsen, the design mind behind the popular Chrome plugin for LinkedIn: Kleo. Listen now on Apple and Spotify.Trevor's journey from a traditional nine-to-five job to successful self-employment is inspiring.

This episode dives deep into the nuances of personal branding on LinkedIn, designing a fractional design career, and being a founding designer for Kleo, which just launched its pro plan.

**Trevor’s LinkedIn**

Building Kleo - Fueling Success for LinkedIn Content Creators

In our discussion, Trevor shares his experiences of replacing his previous income post-layoff and nearly doubling it with strategic client work. He's also developing Kleo, a tool designed to assist regular LinkedIn users to get more active on LinkedIn.

Highlights:

00:00 Starting Content Creation for Personal Branding

00:44 Transition to Freelance and Building Kleo

01:36 LinkedIn Personal Branding and Self-Employment Wins

02:42 Journey from Layoff to Self-Sustaining Business

04:16 Challenges and Epiphanies in Freelance Work

08:31 Consistency and Strategy in LinkedIn Posting

19:26 The Importance of Content Creation and Overcoming Barriers

23:47 The Myth of Creativity

24:37 Connecting Ideas for Niche Markets

25:34 Content Creation and Audience Engagement

26:26 The Power of Video Content

27:36 Building a Personal Brand

31:34 Leveraging Community and Feedback

41:29 Final Thoughts and Takeaways

Listen now on Apple and Spotify.

Building a Sustainable Career Path

Trevor has created a blueprint for freelancers who aspire to build a sustainable and rewarding career path by diversifying income streams while working on passion projects. His insights into balancing side hustles and main gigs highlight the importance of planning and perseverance.

Highlights include:

💪 Trevor’s tactical steps in creating a stable income stream post-layoff

🔥 The exponential benefits of engaging consistently and meaningfully on LinkedIn

✌️ The vision behind Kleo and its potential to transform how creators interact and grow on LinkedIn

Actionable Takeaways

1. Embrace Client Work as a Core Commodity:

"Client work should not be viewed as supplementary to a full-time job but can be structured to be full-time through strategic partnerships." - Trevor Nielsen

Action Tip: Methodically assess part-time opportunities to ensure a stable recurring income, equating to a traditional full-time salary. Prioritize recurring partnerships for stability.

2. Utilize LinkedIn for Personal Branding:

LinkedIn isn't just a job board. Developing your personal brand through consistent posting and interaction can open doors you never expected. - Trevor Nielsen

Action Tip: Start posting regularly. Begin by sharing insights from your professional journey, and gradually engage with your network by commenting on posts and joining relevant conversations. The highest impact is providing relevant comments on the people’s posts you follow. Post for exposure and comment for opportunities.

4. Transform Setbacks into Opportunities:

“Following the layoff, I turned to freelancing, redefining my career and turning what could have been a setback into a successful voyage of self-employment.” – Trevor Nielsen

Action Tip: In career transition or upheaval, view unexpected changes as opportunities to pivot and innovate rather than setbacks.

Thank you for tuning in, and I hope you glean as much insight from Trevor’s journey as I did.

Best,

Caden Damiano

caden@hey.com

Listen now on Apple and Spotify.

Here’s what really stood out to me:

Actionable Takeaways

Table of Contents

✅ Rethinking Product Management Roles

✅ The Power of Team Chemistry

✅ Embracing Continuous Learning

✅ Simplifying Technology Adoption

✅ Rethinking Product Management Roles

We dove into the actual role of a product manager, debunking the myth that they should act like CEOs of their products. Jason explained how the essence of effective product management lies in influence and collaboration rather than authoritarian control.

Takeaway: Influence is Key

"Ultimately you have to get a team oriented around a vision and they have to buy in on their own. You can't force them to..."

-Jason Monberg

Action Tip:

👉 Build a collaborative atmosphere where team members feel heard. Your job is to have a vision and sell it.

👉 If you can’t sell it, return to the drawing board; don’t promise things to the leadership team of customers that you can’t sell internally. 👉 If you can’t sell it, you may not be the right person for that role. Product Managment is a leadership position. Make sure you make sure you are pointing everyone is the right direction.

✅ The Power of Team Chemistry

Our talk emphasized the importance of team chemistry and dynamics. Successful projects often hinge on how well team members communicate and work together rather than just the tech stack they use.

Takeaway: Foster Team Cohesion

"If the chemistry with the leadership of the product management team isn't spot on, that's always going to be a mess."

-Jason Monberg

Action Tip: 👉 Keep tabs on team dynamics and encourage open communication to ensure everyone is moving in the same direction.

✅ Embracing Continuous Learning

Continuous learning came up as a must for staying competitive in tech roles. Jason highlighted the importance of viewing yourself like a professional athlete, always training and upskilling for those pivotal moments.

Takeaway: Keep Learning

"Think about yourself as an elite athlete... take pride in yourself no matter what you're doing."

Jason Monberg

Action Tip: 👉 Make it a habit to explore new skills and tech platforms weekly. Staying informed helps keep you agile and relevant.

👉 Read “Chop Wood, Carry Water” to learn more about this philosophy.

✅ Simplifying Technology Adoption

We discussed the balance between tech adoption and business needs. Sometimes, the best tech decisions involve simplifying rather than complicating your processes.

Takeaway: Simplify for Success

"I'm excited to see a simplification of technology... You don't need all the technology all the time."

-Jason Monberg

Action Tip:

👉 Review your tech setup regularly to streamline operations and align them more closely with business goals.

Listen now on Apple and Spotify.

Seamus MacIsaac offers a wealth of experience. Having transitioned from a small-town upbringing in Nova Scotia to spearheading product management in various industries, including construction and payments.

Table of Contents

✅ What Empathy Looks Like in Product Management

✅ Don’t Over-Engineer Before You Have Demand

✅ Digital Transformation Isn’t Just About Adding Technology

✅ Iterate with the “Scooter, Honda Civic, Ferrari” Framework

Taha's journey from Director at Tableau Public to an accidental author is filled with insights about curiosity, the power of storytelling, and the intersection of technology and nature.

Chapters

00:00 The Value of Curiosity and Exploration

01:12 Introducing Taha Ibrahimi

03:09 Taha's Eclectic Career Journey

04:36 The Birth of a Book During COVID

10:06 Challenges in Identifying Trees

12:51 Combining Data and Drawing

15:22 Validating Data with Field Work

26:08 The Role of AI in Video Editing

26:46 Empowerment Through Technology

29:23 Cultural Significance of Trees

30:50 The Unexpected Success of the Book

33:10 The Power of Storytelling

37:49 Curiosity and Data Visualization

45:10 Exploring Seattle's Diverse Tree Collection

46:58 Conclusion and Final Thoughts

47:56 Special Offer for Listeners

I’m thrilled to share my latest interview with Adam Nash, the Co-Founder and CEO of Daffy, a fintech company dedicated to making charitable giving more accessible and impactful.

* Adam’s Linkedin

* Donate $25 to any cause of you choosing using this link

Adam has a full-stack background in managing, designing, and engineering products, having held key roles at companies such as Dropbox, LinkedIn, and eBay and recently as CEO of Wealthfront. Highlights

👉 The multidisciplinary approach to innovation in technology he developed in his career where His experiences span notable companies such as Apple, LinkedIn, and Dropbox,

👉 The importance of combining engineering, design, and business insights and how he used his diverse skill set to drive innovation.

👉 Adams career advice: How to be fluid and adapt roles to create impactful solutions.

👉 We get tactical in designing to promote a desired behavior. It’s fun to talk shop with a CEO with excellent design taste.

Adam’s latest venture

Daffy stands for the Donor Advised Fund for You. It’s a unique platform inspired by the belief that everyone should have a straightforward way to put money aside for charity, much like a 401(k) for retirement.

Daffy is designed to automate the giving process, making it easier for people to commit financial resources to causes they care about.

Highlights include:

💪 Daffy’s mission to help people be more generous by simplifying the giving process

🔥 How their latest launch of Daffy Campaigns campaigns encourages more people to donate.

✌️ How Daffy leverages technology to create a communal space for philanthropy.

Chapters:00:00:00 Adam Career From Apple to CEO of Wealthfront

00:05:37 The Importance of Multidisciplinary Innovation

00:11:35 Pushing the Creative Process at Apple

00:15:28 Donor Advised Funds

00:22:49 Daffy is like Acorns for giving

00:29:12 Solving Emotional Problems with Design

00:36:28 Problems, especially with software, are emotional

00:39:54 Daffy and the Future of Giving

This episode explores the intersection of technology, strategy, and the essence of building communities within products.

Bryan brings a wealth of experience from his tech strategy consulting firm and shares his unique approach to building scalable and engaging products.

In this episode, he credits much of Goldfish’s success with his “motivation-driven design” process, which highlights the importance of aligning user motivations with business goals.

We discussed:

(04:41) Bryan’s background and the genesis of Goldfish Code

(08:11) Insights on the role of a virtual CTO and strategic consulting

(12:01) Building products with a motivation-driven design (15:18) The importance of community in product strategy

(19:47) Effective client relationship management

(24:30) Real-world examples of automation and efficiency improvements

(30:18) Custom builds vs. leveraging existing solutions

(35:45) The evolving role of AI in software development

(41:04) How human needs drive business solutions

Interview Takeaways:

Understanding Motivation-Driven Design

Bryan’s approach focuses on user motivations to drive product development, such as loss avoidance and community belonging.

Using behavioral psychology techniques, Goldfish Code ensures that products meet functional requirements and engage users emotionally.

Community as a Core Element

Bryan believes that effective products foster a sense of community among users.

Whether it’s a FinTech application or an e-commerce platform, building features encouraging users to feel part of a larger group can drive engagement and loyalty.

The Role of a Virtual CTO

A virtual CTO brings strategic insights that can make or break a product. By starting with a minimum viable workflow and iterating based on real user feedback, Bryan’s team helps businesses avoid common pitfalls and build scalable solutions.

Balancing Custom Builds and Existing Tools

Rather than reinventing the wheel, Bryan emphasizes leveraging existing tools and frameworks. This approach not only speeds up development but also allows for more focus on the unique aspects of the product that differentiate it in the market.

Chapters

01:00 Meet Allison Nulty: Product Leader at Contra

03:06 The Vision and Mission of Contra

06:46 Challenges and Strategic Decisions at Contra

08:16 Building a Marketplace and Community

09:11 Contra's Unique Business Model

11:59 Scaling with Freelancers and Flexible Talent

14:29 Customer-Centric Product Development

22:20 The Power of Customer Feedback

24:27 Customer Obsession and Building Relationships

24:51 The Journey of Starting a Podcast

26:30 From Consulting to Product Management

28:06 Lessons from Working as a Managment Consultant to Product Management.

33:23 Empowering Teams with Ownership

39:43 The Importance of Communication and Transparency

43:13 Final Thoughts and Reaching Out

45:31 Outro and Special Offer

You read that right; Harry has a wide range and can bridge the gap between experienced design leadership and operational excellence. Harry has led at DreamWorks, Hewlett-Packard, Rackspace, and Apple. 

We dive into the complexities of balancing operations and design, the challenges faced by product leaders, and the political nature of leadership and decision-making. Harry introduces his highly practical DEGAP framework for prioritization, emphasizing the importance of intentional decision-making and guiding me through the tangible steps involved. 

Finally, we explore how prioritization plays a crucial role in the lives of individual contributors, teams, and organizations. He aims to equip you with practical tools to significantly enhance your decision-making and leadership skills.

20% of Harry Max’s book “Managing Priorities”: mp-twop

You can buy his new book “Managing Priorities” through this link

Chapters

00:20 The Unique Role of a Fractional Executive

00:58 Bridging Operations and Design: A Dual Competency

03:04 The Challenges of Product Leadership

08:19 The Art of Prioritization in Leadership

08:24 Unpacking the Book on Managing Priorities

15:19 Real-World Prioritization: A Case Study from Rackspace

27:22 The Five Steps of Effective Prioritization

30:30 Unpacking the Prioritization Process

31:01 Exploring Decision-Making Tools and Techniques

35:47 Deep Dive into the D-GAP Methodology

40:18 Applying Prioritization in Personal and Professional Contexts

40:57 Insights on Individual Contributor Prioritization

47:36 Concluding Thoughts on Prioritization and Productivity

We touched on:

* Why corporate meetings are mostly a waste of time, and how to fix your approach to meetings.

* Prioritizing which meetings to attend and gaining buy-in for design projects.

* I walk through my approach to working with cross-functional partners using an underrated methodology.

* Meeting one-on-one with key stakeholders early on to understand their concerns and bring them along on the design journey.

* Different working styles and mindsets, from perfectionistic craftspeople to systems thinkers who embrace problem-solving.

Building trust and credibility with stakeholders is crucial, and I highlighted the significance of making people feel understood and involved in the creative process.

I emphasized the importance of competencies like good judgment over specific skills when aiming for higher levels of influence.

Overall, the discussion provides excellent strategies for product people, designers, and creatives looking to protect their time, have a more significant impact, and shape company decisions.

Learn how to design a business and subscribe to the Way of Product

In this episode, Norma, a veteran in the video conferencing industry with 19 years of experience, shares her journey from starting in Hamburg and Cisco to becoming the Head of Product at Neat.

This company blurs the line between the office and remote workers. I am in awe of what goes into seamless videoconferencing experiences.

She discusses the magic of creating products that facilitate human connection across distances and the collaborative effort it involves, especially the intricate balance between design, technology, and user experience.

Norma emphasizes the importance of design-driven approaches, the complexities behind the simplicity of video conferencing products, and how balancing various considerations like audio quality, compliance, and aesthetics leads to products highly valued by customers.

She highlights the role of psychological safety and trust within teams, facilitating effective cross-functional collaboration, and the impact of directly engaging with customers and sales teams to understand better and meet their needs.

Norma also touches on her reasons for joining Neat, the excitement of working in a startup environment, and the recent launch of Neat's second-generation video conferencing bar, encapsulating her passion for innovation in the industry.

00:00 Welcome and Introduction

00:05 Norma's Journey in the Video Conferencing Industry

01:02 Inside the World of Video Conferencing Tech

04:53 The Magic of Product Development and Design

10:25 Learning from Mistakes: A Product Launch Story

13:11 Building a Culture of Psychological Safety and Trust

18:00 The Power of Inclusive Product Strategy

23:51 Transitioning from Cisco to NEAT: A New Chapter

26:51 Understanding Business Through Product Leadership

28:18 The Role of Design in Product Success

33:07 Collaboration Across Departments: A Key to Success

People will spend $200,000 on a Pokemon card, and the team at Rally understands that.

On #wayofproduct this week, Rob Petrozzo, co-founder and Chief Product Officer at Rally, shares his journey of creating a groundbreaking platform like a collectibles stock market. Rally has become a hub for trading everything from dinosaur fossils and classic cars to modern NFTs and trading cards, fostering a community of shared interests and passion.

Here's what we're diving into:

⭐ The inception of Rally and how it evolved from a concept to a thriving community around unique and emotional collectibles.

⭐ Rob's personal journey and how his passion for tangible art and design influenced Rally's development.

⭐ The challenges and strategies in making high-value collectibles like classic cars and Warhol paintings accessible to more people.

⭐ Insights into the storytelling aspect of products, emphasizing that it's not just the item but its story that creates value and captivates people.

⭐ How Rally's approach differs from traditional financial platforms by focusing on user experience, akin to exploring a museum, rather than just transactions.

⭐ The importance of authentic marketing and design that resonates with consumers on an emotional level, especially in a world where traditional advertising methods are becoming less effective.

⭐ Rally's strategy to build a strong community by offering a platform that's as engaging and informative as it is transactional.

Subscribe and listen to The Way of Product at www.wayofproduct.com

————————————————————

Hi! I'm Caden Damiano, I'm an interaction designer, collaboration coach, and lifelong student of the craft of product development.

I believe that product development is a liberal art, meaning you must experience multiple disciplines and perspectives to know how to make something that customers tell their friends about.

In short, I believe great products have free word-of-mouth marketing.

Follow me here on LinkedIn for daily clips from my interviews with product professionals and insights on making great products.

AI is “autocomplete” on steroids in its current form.

On #wayofproduct this week, we're thrilled to have Michael Tinglin back on the show!

Michael is a design leader who has worked at places like 7-Eleven, and Fannie Mae, and recently was Head of Design at Confluence.

He taught me about the non-linear career path, where you can jump between management and IC work depending on your interests.

A designer from Dallas, Texas, Michael has a passion for UX and product design.

Michael brings his unique insights into AI and product design, emphasizing that AI is not “a magic bullet” but a tool that, when utilized thoughtfully, can be transformative.

In this episode, we dive into:

⭐ The state of AI in the media and marketing world and how it's not as “new” as many think.

⭐ The importance of not just adding AI for the sake of it but ensuring it adds real value and ROI.

⭐ How AI might be the next phase of true personalization in e-commerce, moving beyond creepy ads to genuinely valuable recommendations.

⭐ The conversation around strategy in design and product management and how agile is often a tactic rather than a strategy.

⭐ Michael's perspective on innovation as a business growth mechanism and how companies like Berkshire Hathaway transformed from furniture stores to investment giants through innovative thinking.

Subscribe and find where to listen to “The Way of Product” at

way+of+product+dot+com (LinkedIn will throttle this post for sharing a link)

———————————————————

Hi! I'm Caden Damiano; I'm an interaction designer, collaboration coach, and lifelong student of the craft of product development.

I believe that product development is a liberal art, meaning you must experience multiple disciplines and perspectives to know how to make something that customers tell their friends about.

In short, I believe great products have free word-of-mouth marketing.

Follow me here on LinkedIn for daily clips from my interviews with product professionals.

#UXDesign

#AI

#ProductDesign

#Innovation

#WayOfProduct

#CreativeStrategy

In this episode, we explore:

⭐ The origins of design thinking from engineering and its practical applications in business and design.

⭐ Bryan's extensive experience in helping companies like Netflix, Hulu, and Disney craft great things through design.

⭐ The evolving role of design in product development and the shifting dynamics between product design and UX design.

⭐ The importance of system thinking in design and how it influences the creation of user experiences.

⭐ Bryan's approach to design as a tool for facilitating organizational change and producing impactful products.

⭐ The role of intuition in the design process and the balance between gut feelings and structured testing.

⭐ A deep dive into understanding customer needs and integrating feedback loops into design and product development.

⭐ Bryan's insights on successful product development despite team dysfunctions and the focus on creating great products.

⭐ An introduction to Helio, Bryan's continuous discovery tool, and its impact on gathering rapid customer feedback for digital products.

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺 Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

📲 Watch Episode Clips on X - https://twitter.com/Caden_Damiano

📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Don't miss this opportunity to gain insights from Bryan Zmijewski's vast experience in design and technology on The Way of Product. Subscribe now for more thought-provoking conversations and cutting-edge strategies in product development.

#DesignThinking

#ProductDesign

#UXDesign

#Innovation

#WayOfProduct

#Technology

#CustomerFeedback

#Helio

#ContinuousDiscovery

Here's what we're diving into:

⭐ Mitch's unique journey from a small basement startup, Simple Nexus, to its acquisition by nCino, valued at $1.2 billion.

⭐ The critical role of design vision and strategy in propelling a company's growth and maturation.

⭐ How continuous user-focused design and customer listening shaped Simple Nexus's success and acquisition appeal.

⭐ The power of sharing and collaborating on design visions company-wide, creating a unified direction and excitement.

⭐ Mitch's transition from hands-on design to empowering and leading a team of designers in a larger corporate environment.

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺 Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

📲 Watch Episode Clips on X - https://twitter.com/Caden_Damiano

📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Who is Mitch Clements?

Mitch Clements is a dynamic leader in the world of product design, whose passion for creating impactful user experiences has driven his career from a hands-on designer to a strategic manager. Starting at Simple Nexus, a small basement startup, he played a significant role in the company's rapid growth and eventual acquisition by nCino. Mitch's approach goes beyond aesthetics; it's about deeply understanding user needs and crafting strategies that align with the company's vision. His journey is a testament to the power of design thinking and its role in transforming not just products but entire companies.

For more of Mitch's inspiring story and insights into leading design in the tech industry, check out the episode and don't forget to subscribe to The Way of Product for more enlightening conversations.

#ProductDesign

#StartupGrowth

#Leadership

#WayOfProduct

#Innovation

Connect with Mitchell Clements https://www.linkedin.com/in/mitchell-clements/

00:00 The Journey of a Startup

01:08 Acquisition by nCino

01:28 Transition to a Manager Role

02:03 The Importance of Design in Unconventional Industries

03:56 The Challenges of Scaling a Startup

05:31 The Role of Design in Streamlining the Home Ownership Journey

06:45 Creating a Vision for the Future

08:16 The Impact of Design on Acquisition

09:01 The Importance of a High-Level Vision

10:30 The Role of Design in Company Strategy

12:36 The Power of Collaborative Vision

23:59 The Transition from Designer to Manager

29:15 Conclusion

Here's what we're exploring:

⭐ How AI is reshaping the landscape of content creation, making it more accessible and efficient for everyone.

⭐ Ajay's journey from founding startups at 17 to spearheading a revolutionary platform that integrates design, video, and AI.

⭐ The challenges and opportunities in navigating the saturated social media planning and creation landscape.

⭐ The transformative impact of AI on small businesses and individual creators, enabling them to produce content at scale.

⭐ Insights into the evolving nature of work and collaboration, especially in a post-pandemic world where remote teams are the norm.

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺 Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

📲 Watch Episode Clips on X - https://twitter.com/Caden_Damiano

📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Who is Ajay Yadav?

Ajay Yadav is more than just an entrepreneur; he's a visionary who's been building companies since his teens. Now, with Simplified, he's turning the tide in content creation by harnessing the power of AI to streamline and enhance the process for marketers and creators alike. Ajay's passion lies in breaking down barriers and democratizing content creation, making it possible for anyone, anywhere, to share their voice and build their brand.

For more of Ajay's revolutionary insights and to learn about Simplified, check out the episode and don't forget to subscribe to The Way of Product for more inspiring stories and strategies.

#CreativeIndustries

#FutureOfAI

#ContentCreation

#WayOfProduct

#InnovativeEntrepreneurship

Connect with Ajay https://www.linkedin.com/in/yadavajay/

Start your content creation journey using a free account at www.simplified.com

00:00 The Power of AI in Small Businesses

00:38 The Importance of Online Presence

01:10 Leveraging AI for Content Creation

01:47 The Future of AI and Creative Industries

02:10 The Evolution of Content Creation Tools

02:21 The Challenges of Collaborative Work

02:37 The Role of AI in Streamlining Workflows

02:57 The Impact of Content Creation on Personal Branding

04:40 The Journey of Building a Startup

09:16 The Shift in Content Creation

10:38 The Role of AI in Content Repurposing

25:13 The Impact of AI on Traditional Businesses

27:35 The Power of Content Creation in Building Trust

29:12 The Rise of TikTok and Staying Relevant

29:35 Promoting the Podcast and Upcoming Book

30:22 The Power of AI in Content Creation

31:25 The Role of Consistency in Content Creation

32:18 The Impact of AI on Design Thinking

32:56 The Challenges of Content Creation and Marketing

34:43 The Role of AI in Streamlining Content Creation

35:42 The Importance of Authenticity in AI-Generated Content

38:20 The Power of AI in Personal Branding

45:06 The Future of Small Businesses and AI

46:12 The Challenges of Building End-to-End Workflow Software

52:39 The Importance of Trying AI Tools

54:11 Closing Remarks and Sponsor Message

Here's what we're unpacking:

⭐ Curt's perspective on Apple as a benchmark for multi-stakeholder design and how they've successfully integrated their mission with profitability and environmental sustainability.

⭐ The importance of designing for multiple stakeholders and how this approach has evolved from Curt's early days in annual report design to current global strategies.

⭐ The role of systems thinking in business and design, considering the broader ecosystem in which they operate.

⭐ Insights from Curt's collaboration with Yale's stakeholder innovation and management program and how businesses are rethinking their approaches to stakeholder engagement.

⭐ Reflections on the dynamic between solving big global issues and addressing immediate, smaller challenges, and how this impacts long-term value creation.

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺  Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

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📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Who is Curt Schreiber?

Curt Schreiber is not just a designer; he's a visionary thinker who has been shaping the world of design for over four decades. As the Chief Creative Officer at VSA, Curt has steered the firm through evolving landscapes, always with an eye on how design impacts and is influenced by various stakeholders. His work is not just about aesthetics but about creating meaningful connections and driving innovation.

For more of Curt's profound insights and to understand the future of multi-stakeholder design, check out the episode and don't forget to subscribe to The Way of Product for more enlightening conversations.

#MultiStakeholderDesign

#PurposeDrivenOrganization

#InnovativeThinking

#WayOfProduct

#BusinessStrategy

Connect with Curt: https://www.linkedin.com/in/curtschreiber/

00:00 The Success of Apple in Multi-Stakeholder Design

01:33 Conversation with Kurt Schreiber

02:45 Introduction to the Podcast

03:45 Interview with Kurt Schreiber

04:40 Discussion on Stakeholder Management

05:11 Insights from Yale Business School

12:11 Discussion on Electric Vehicles

16:18 Apple's Approach to Multi-Stakeholder Design

17:56 Discussion on Organizational Structure

21:52 Challenges in Identifying the User

23:52 Reflections on Steve Jobs and Apple's Brand

25:21 Unpacking the Concept of Brand

25:44 The Role of a CEO in Upholding a Brand's Enduring Idea

27:16 Intermission: A Special Request for Podcast Subscribers

27:56 Exploring Successful Companies and Their Brands

28:53 The Evolution of IBM's Brand

42:57 The Importance of Systems Thinking in Design

43:53 Closing Remarks and Recommendations

46:15 Post-Show Announcements and Offers

Here's what we're getting into:

⭐ Michael's philosophy on design as a brand exercise and his approach to creating iconic, beloved products.

⭐ Insights from his time working with Michael Jordan and how those experiences shaped his approach to design and collaboration.

⭐ The importance of understanding your brand's identity and audience to create relevant and resonant products.

⭐ Michael's journey from major brands to an independent consultant, and the lessons he's learned about effective collaboration and respecting a brand's purpose.

⭐ The power of storytelling in design and how understanding narratives can drive better product development.

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺  Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

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📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Who is Michael DiTullo?

Michael DiTullo is a design force to be reckoned with. Having worked with some of the most recognizable brands in the world, Michael's expertise spans from creating iconic sneakers at Nike and Jordan to pushing the boundaries in industries like audio equipment and architectural systems. His unique approach to design is not just about aesthetics; it's about understanding the core of what makes a brand tick and delivering products that embody that essence. Michael believes in the power of design to transform everyday experiences into moments of joy and inspiration.

Join us as we dive into Michael's world of design, storytelling, and innovation on The Way of Product. Don't forget to subscribe for more captivating stories and insights into the world of product design.

#CreativeVision

#DesignLeadership

#BrandStorytelling

#WayOfProduct

#InnovativeDesign

Connect with Michael: https://www.linkedin.com/in/michaelditullo/

00:00 Introduction and Career Journey

01:15 The Art of Iconic Design

02:03 The Apple Aesthetic and Branding

05:03 Understanding Your Target Audience

08:21 The Importance of Product Love and Belief

09:10 Creating for Specific Audiences

09:33 Working with Michael Jordan

21:51 The Role of Design in Different Industries

25:28 The Power of Personal Branding

26:16 The Impact of Personal Definition

31:08 The Power of Defining Yourself

31:23 Transitioning Careers: From Nike to Frog Design

32:13 The Art of Interviewing: Storytelling and Control

32:47 Defining Your Professional Identity

33:19 Collaboration and Leadership in Design

35:27 The Impact of Directness and Honesty

36:27 Understanding Your Brand's Perception

36:57 The Importance of Consumer Perspective

40:48 Learning from Mistakes: The Polk Audio Story

43:40 The Principle of Maya in Design

45:38 Designing for Digital First Companies

55:13 Designing an Electric Speedboat

59:01 The Role of Intuition in Design

01:00:20 Maintaining Integrity in Design

𝗨𝘀𝗲 𝗧𝗵𝗶𝘀 𝗣𝗿𝗼𝗰𝗲𝘀𝘀 𝘁𝗼 𝗣𝗿𝗲𝘃𝗲𝗻𝘁 𝗥𝗲𝘄𝗼𝗿𝗸, 𝗕𝘂𝗹𝗹𝗲𝘁𝗣𝗿𝗼𝗼𝗳 𝗣𝗿𝗼𝗱𝘂𝗰𝘁 𝗔𝗿𝗰𝗵𝗶𝘁𝗲𝗰𝘁𝘂𝗿𝗲, 𝗮𝗻𝗱 𝗨𝗻𝗰𝗼𝘃𝗲𝗿 𝗙𝗶𝗿𝘀𝘁 𝗣𝗿𝗶𝗻𝗰𝗶𝗽𝗹𝗲𝘀

On hashtag#wayofproduct this week, Sophia V Prater, a trailblazing UX educator, consultant, and the founder of the object-oriented UX methodology, joins us to dive deep into her innovative approach to user experience design. She shares her journey from her childhood passion for design to revolutionizing UX with her unique methodology, emphasizing the need for harmonizing design, engineering, and product management.

Here's what we're unpacking:

⭐ The transformative philosophy of object-oriented UX and how it helps prevent unnecessary rework and disruption.

⭐ Insights into Sophia's journey from industrial design to UX and her mantra of "Teach what you need to learn."

⭐ The vital role of object-oriented UX in building a bulletproof software architecture and information architecture.

⭐ Strategies for UX professionals to communicate effectively with developers and stakeholders, ensuring a user-centered approach.

⭐ An exploration of the ORCA (Objects, Relationships, Calls to Action, and Attributes) process and its impact on designing intuitive and effective systems.

Subscribe and listen to The Way of Product on...

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𝗪𝗵𝗼 𝗶𝘀 𝗦𝗼𝗽𝗵𝗶𝗮 𝗣𝗿𝗮𝘁𝗲𝗿?

Sophia Prater is more than a UX consultant; she's a visionary who has mastered the art of transforming complex systems into intuitive and user-friendly experiences. With a background in industrial design, she's spent years perfecting her object-oriented UX framework, helping teams worldwide to prioritize effectively and build products that resonate with users on a deeper level.

Sophia's approach isn't just about making things look good; it's about making them work seamlessly and meaningfully.For more of Sophia's revolutionary insights and to learn about her framework, check out the episode, and don't forget to subscribe to The Way of Product for more inspiring stories and strategies.

Connect with Sofia: https://www.linkedin.com/in/sophiav/

00:00 Introduction to Intelligent Iteration

00:16 The Importance of UX Language

00:37 Introducing Sophia Prater: UX Educator and Consultant

00:45 The Impact of Object Oriented UX Design

01:02 Personal Experiences and Insights into UX Design

01:15 Promotion and Benefits of the Course

01:40 Introduction to The Way of Product Podcast

01:49 The Challenges of Being a Prog Leader

02:14 Invitation to Join the Newsletter Crew

02:39 Interview with Sophia Prater

02:56 Sophia's Journey into UX Design

06:43 The Evolution of Sophia's UX Design Process

08:27 The Impact of Object Oriented UX on Career Growth

20:19 The Importance of Cardinality in UX Design

31:49 The Value of OUX for Businesses

36:21 The Role of OUX in Defining Project Scope

37:47 The Art of Snarky Responses

38:00 Understanding Purchase Order Deliveries

38:26 Assessing Risks in Assumptions

39:14 The Power of Asking Deep Questions

40:04 Podcast Intermission: A Special Request

40:43 The Importance of Articulating Design Instincts

41:33 The Airbnb Example: A Lesson in Object Oriented UX

47:02 The Challenges of Growing a Business

49:56 The Power of Object Oriented UX in Product Team Collaboration

51:45 The ORCA Process: A Deep Dive

56:42 The Benefits of the ORCA Process

01:03:08 The Future of Object-Oriente UX

01:09:28 Closing Remarks and Special Offers

Here's what we're talking about:

⭐ The significance of trust and shared values in fostering healthy, productive disagreements and biases within teams.

⭐ The impact of remote work on collaboration, efficiency, and the sourcing of diverse ideas.

⭐ The balance between the need for in-person interactions and the benefits of virtual collaboration.

⭐ The importance of aligning company operations with values and the mission rather than conforming to rigid frameworks.

⭐ Sharif's personal journey from discovering computers to overcoming dyslexia and leading a global design agency.

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺  Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

📲 Watch Episode Clips on X - https://twitter.com/Caden_Damiano

📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Who is Sharif Matar?

Sharif Matar is a visionary at the intersection of design and technology. Growing up in Hawaii with a passion for creativity sparked by overcoming dyslexia, Sharif discovered the transformative power of technology early on. Today, as a leader at Product Inc., he navigates the complexities of global product design and champions remote work's potential to tap into diverse talent and ideas. Sharif believes in leveraging technology to connect ideas and people across geographical boundaries, driving innovation and growth.

Join us as we explore Sharif's insights and journey on The Way of Product. Don't forget to subscribe and immerse yourself in the conversations shaping the future of design and technology.

#GlobalDesign

#RemoteWork

#CreativeTechnology

#WayOfProduct

#ProductManagement

Connect with Sharif

00:00 The Power of Disagreements and Biases

02:59 Interview Begins: Sharif's Journey

03:35 The Impact of Technology on Learning and Connection

07:04 The Nuances of Remote Work

11:06 The Power of Diverse Teams

28:01 Podcast Break and Request for Support

28:41 The Challenges of Hiring and Retention in Tech

28:41 Resuming Conversation: The Myths of Hiring

30:39 The Importance of Building Relationships in Business

33:29 Optimizing for Metrics vs. Providing Value

33:37 The Importance of Tribalism and Human Connection in Business

34:10 The Role of Hormones and Relationships in Business

36:21 The Impact of Company Policies on Social Issues

39:23 The Importance of Alignment Over Agreement in Business

39:45 The Role of Belief in Business Success

40:14 The Power of Owning Something Valuable

44:11 The Importance of Diversity and Disagreement in Business

51:10 The Role of Designers in Business Leadership

51:30 The Impact of Business Design on Success

56:30 The Importance of Working on the Business, Not in It

59:01 The Role of Questioning and Healthy Conflict in Business

Here's a sneak peek of our conversation:

⭐ How agile methodologies in software development impacted the speed and approach of research.

⭐ Ari's unique journey from law enforcement to leading research in major tech companies.

⭐ The critical role of research in the business environment and how researchers can serve as strategic advisors.

And there's a lot more insight into where that came from!

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

Who is Ari Zelmanow?

𝗔𝗿𝗶 𝗭𝗲𝗹𝗺𝗮𝗻𝗼𝘄 𝗶𝘀 𝘆𝗼𝘂𝗿 𝗴𝗼-𝘁𝗼 𝗲𝘅𝗽𝗲𝗿𝘁 𝗶𝗻 𝘂𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱𝗶𝗻𝗴 𝗰𝗼𝗻𝘀𝘂𝗺𝗲𝗿 𝗺𝗮𝗿𝗸𝗲𝘁 𝗯𝗲𝗵𝗮𝘃𝗶𝗼𝗿. 𝗪𝗶𝘁𝗵 𝗮 𝗯𝗮𝗰𝗸𝗴𝗿𝗼𝘂𝗻𝗱 𝗮𝘀 𝗮 𝗽𝗼𝗹𝗶𝗰𝗲 𝗱𝗲𝘁𝗲𝗰𝘁𝗶𝘃𝗲, 𝗔𝗿𝗶 𝗮𝗽𝗽𝗹𝗶𝗲𝘀 𝗵𝗶𝘀 𝗶𝗻𝘃𝗲𝘀𝘁𝗶𝗴𝗮𝘁𝗶𝘃𝗲 𝘀𝗸𝗶𝗹𝗹𝘀 𝘁𝗼 𝗺𝗮𝗿𝗸𝗲𝘁 𝗿𝗲𝘀𝗲𝗮𝗿𝗰𝗵, 𝗵𝗲𝗹𝗽𝗶𝗻𝗴 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀𝗲𝘀 𝘂𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱 𝗵𝘂𝗺𝗮𝗻 𝗯𝗲𝗵𝗮𝘃𝗶𝗼𝗿 𝗿𝗲𝗹𝗮𝘁𝗲𝗱 𝘁𝗼 𝘀𝗵𝗼𝗽𝗽𝗶𝗻𝗴, 𝗯𝘂𝘆𝗶𝗻𝗴, 𝗮𝗻𝗱 𝘂𝘀𝗶𝗻𝗴 𝗽𝗿𝗼𝗱𝘂𝗰𝘁𝘀.

Connect with Ari: https://www.linkedin.com/in/zelmanow/

The Influential Researcher Newsletter: https://influentialresearcher.com/

00:22 Ari Zelmanow's Journey from Police Detective to Market Detective

01:31 The Importance of Research in Business

02:34 The Sherlock Holmes Influence

04:01 The Magic of Research and the Sherlock Holmes Persona

05:37 The Role of Researchers in Business

06:07 The Challenges of Democratizing Research

07:08 The Value of Experienced Researchers

08:17 The Problem with Research Templates

08:31 The Difference Between a Discussion Guide and an Interview Template

09:06 The Role of Research in Startups

10:32 The Experience of Building a Research Function at Twitter

16:14 The Future of Research

16:27 Lessons from Police Detective Work Applied to Research

18:56 The Importance of Abductive Reasoning in Research

20:41 The Difference Between Deduction, Induction, and Abduction

26:25 The Burden of Proof in Business

27:48 Understanding Usability Testing and Decision-Making

28:03 The Role of Certainty in Decision Making

28:44 The Importance of Research in Decision Making

29:20 The Impact of Research on Product Development

29:38 The Research Process and Its Challenges

30:02 The Role of a Researcher: Delivery Person vs Consultant

31:07 The Shift from Traditional Research Reports

31:33 The Power of Observations and Customer Insights

33:50 The Concept of a Top Line Report

34:03 The News Organization Model for Research

34:17 The Role of Researchers in Interrogating Evidence

35:57 The Importance of Ethical Reporting in Research

37:37 The Challenges and Future of Participant Recruitment

42:43 The Role of Researchers in Decision Making

53:01 The Role of Researchers in Interpreting and Delivering Data

53:47 The Importance of Storytelling in Research

54:19 The Influential Researcher Course and Final Thoughts

Here's what we're unpacking:

⭐ Why sometimes stopping is the best way to move forward
⭐ The Swedish 'Feca' and the art of slowing down
⭐ How leaders can create workplaces where everyone thrives
⭐ What 'practice spotting' is and how it can guide your career
⭐ The role of narratives in the workplace and their impact on your day-to-day

There's more to the story, so tune in!

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺  Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

📲 Watch Episode Clips on X - https://twitter.com/Caden_Damiano

📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Meet Justin Dauer:

Justin is the guy who's rethinking how we approach work. At Anomaly by Design, he's helping teams find the sweet spot between creativity and fulfillment. He's not just talking the talk; his book and his work with CVS Health have shown he's all about making work matter.

Anomaly by Design's motto? Finding fulfillment in your work is crucial, and Justin's here to show you why.

Check out the full conversation on YouTube and find out where you can follow Justin's journey.

#RealTalk
#MindfulWork
#CreativeJourney
#WayOfProduct
#LifeByDesign

Connect with Justin: https://www.linkedin.com/in/pseudoroom/

Buy “In Fulfillment: A Designers Journey”: https://www.in-fulfillment.com/

CHAPTERS

00:28 Justin's Journey and Career Background

03:09 Discussion on Justin's Book and Personal Fulfillment

03:37 Brief Interruption and Personal Anecdotes

04:15 Deep Dive into Personal Values and Career Evolution

05:25 Exploring the Concept of Fulfillment in Design

05:38 The Transition from Individual Output to Team Output

10:05 The Importance of Humility and Growth in Design

11:23 The Role of Storytelling in Understanding Personal Values

20:31 The Power of the Blank Canvas and the Value of Challenge

23:18 Practice Spotting: A Tool for Understanding Personal Narratives

30:51 The Importance of Authenticity and Empathy in the Workplace

33:06 The Power of Empathy in Productivity

33:40 The Impact of Empathy on Office Dynamics

34:07 The Role of Fulfillment in Work Culture

34:39 Understanding Adversarial Relationships in the Workplace

35:25 The Consequences of Pushing Agendas in Meetings

36:39 The Importance of Active Listening and Empathy in Problem Solving

36:59 The Power of Storytelling in Building Confidence

37:57 The Impact of Empathy on Work Environment

38:37 The Consequences of Avoiding Deeper Understanding in the Workplace

39:08 The Importance of Evolving in the Workplace

41:07 The Role of Leaders in Fostering Fulfillment

42:17 The Importance of Slowing Down and Pausing with Intent

42:45 The Influence of Swedish Work Culture on Productivity

43:46 The Power of Connection in the Workplace

56:48 The Importance of Prioritizing Fulfillment in Work

Teresa Torres shares her invaluable insights into the intricacies of product discovery and the vital role of user research in product development.

Highlights include:

⭐ The distinction between user research and product discovery

⭐ The importance of building fast feedback loops with customers

⭐ The impact of implementing continuous discovery habits

⭐ The evolution of product teams' understanding of their customers

⭐ Practical tips for enhancing discovery practices and driving better outcomes

Plus, much more!

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://lnkd.in/ghs99F-G

🎧 Spotify - https://lnkd.in/g2YU_eX4

🎧 Google Podcasts - https://lnkd.in/gaXS6i_4

🎧 Audible - https://lnkd.in/gy5EWw-r

How to tune in for the new releases:

📺  Watch the podcast clips - https://lnkd.in/g-UVCNrN

📲 Watch Episode Clips on TikTok - https://lnkd.in/gaEgR-ws

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📸 Follow me on Instagram - https://lnkd.in/gEzmaFS4

Who is Teresa Torres?

Teresa Torres is a renowned product discovery coach, author, writer, extensive blogger, and the author of "Continuous Discovery Habits." With over 12 years of experience, she has worked with numerous teams helping them make better decisions about what to build and how to build it.

Teresa Torres believes that - in her own words - “Product teams need to move fast; we need to get fast answers. Some answers, even if they're less reliable than what we're getting from project-based research, are better than no answers.”

Before becoming a prominent figure in the product discovery domain, Teresa has worn many hats, including research and product management roles, always striving to bridge the gap between customer needs and product development.

Connect with Teresa at www.producttalk.org to access her course training and hire her to coach your team.

05:04 Distinguishing User Research and Product Discovery

07:36 The Role of User Researchers in Product Teams

08:26 Ideal Structure of a Product Team

11:08 The Misinterpretation of the Book's Message

12:28 The Importance of Externalizing Thinking in Product Discovery

19:52 Real-life Application of Continuous Discovery Habits

28:22 The Origin and Development of Continuous Discovery Habits

30:55 Understanding Success and Working Backwards

31:09 The Importance of Measurable Outcomes

31:23 Exploring the Skill of Design Thinkers

31:58 The Role of Expert and Novice Designers

32:25 The Evolution of Understanding in Design

33:05 The Importance of Teamwork in Product Discovery

33:46 The Influence of Academic Research on Design Thinking

34:59 The Challenge of Identifying Assumptions in Teams

35:29 The Use of Story Mapping in Surfacing Assumptions

36:33 The Practical Application of the Book's Content

37:56 The Development of the Book's Methods

38:12 The Iterative Process of Developing a Coaching Curriculum

43:43 The Role of Luck and Process in Business Success

51:23 The Journey to Becoming a Coach

54:16 Final Thoughts and Resources for Further Learning

Highlights include:

⭐ How to pivot strategy in the rapidly changing fintech market

⭐ Balancing creativity and regulatory compliance in financial services

⭐ The importance of diverse skill sets in product development

⭐ The relationship between product design and product management

⭐ Learning from mistakes and adapting strategies for continuous improvement

Plus, much more!

Subscribe and listen to The Way of Product on...

🎧 Apple Podcasts - https://itunes.apple.com/us/podcast/pivot/id1442980948?mt=2&uo=4

🎧 Spotify - https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV

🎧 Google Podcasts - https://www.google.com/podcasts?feed=aHR0cHM6Ly9hbmNob3IuZm0vcy81ODQxMTc0L3BvZGNhc3QvcnNz

🎧 Audible - https://podcasters.amazon.com/podcasts/9ed01fe7-2dbd-4eb6-a114-12ed367e371f

How to tune in for the new releases:

📺  Watch the podcast clips - https://www.youtube.com/channel/UCrBZL31DoAT7vW2vbYkeXhw

📲 Watch Episode Clips on TikTok - https://www.tiktok.com/@caden.damiano?is_from_webapp=1&sender_device=pc

📲 Watch Episode Clips on X - https://twitter.com/Caden_Damiano

📸 Follow me on Instagram - https://www.instagram.com/caden.damiano/

Who is Glendy Kam?

Glendy Kam is a forward-thinking Chief Product Officer at Tessit, specializing in blockchain fintech solutions. With a rich history at JP Morgan and a deep understanding of product management, Glendy is known for navigating the complexities of the financial services market and leading teams toward innovative solutions.

Glendy believes that - in their own words - "Innovation and agility are key to staying ahead in the ever-evolving financial landscape."

Before her current role at Tessit, Glendy spent over a decade at JP Morgan, where she played a pivotal role in launching open banking and API initiatives.

#UX

#UXDesign

#UXResearch

#ProductDesign

#DesignRecruitment

#WayOfProduct

#ProductManagment

00:30 Background and Journey into FinTech

02:14 Career Progression and Industry Focus

05:30 Transition from Consulting to In-house Roles

07:16 The Role of Product in an Organization

09:37 The Importance of Continuity in Product Development

11:01 Learning from Mistakes and Adapting Strategies

18:26 The Role of Communication and Negotiation in Product Management

30:57 Understanding the Relationship between Product Design and Product Management

43:58 Final Thoughts and Contact Information

On #wayofproduct this week, Derlen Chiu shares his perspective on resolving the creative tension between cross-functional team members.

It's no secret that PM and PD have an industry-wide tension. We break that down in this episode.

Highlights include:

⭐ Why focusing too much on the job title blocks good work, especially in a startup, and why Derlen doesn't enforce "staying in your lane" with his team.

⭐ How to decide when PM, PD, and Engineering should take the driver's seat in a project.

⭐ How Dungeons and Dragons is a great metaphor for a well-balanced team. Trust me; it will make sense when you listen to it.

⭐ Derlens Take on Developing a Product Strategy by Thinking in Games.

Plus, much more!

Listen to Derlen's Interview on...

🎧 Apple Podcasts - https://lnkd.in/ghs99F-G

🎧 Spotify - https://lnkd.in/g2YU_eX4

🎧 Google Podcasts - https://lnkd.in/gaXS6i_4

🎧 Audible - https://lnkd.in/gy5EWw-r

📺  Watch clips on YouTube - https://lnkd.in/g-UVCNrN

📲 Watch Episode Clips on TikTok - https://lnkd.in/gaEgR-ws

📲 Watch Episode Clips on X - https://lnkd.in/gSTC5SRU

📸 Follow me on Instagram - https://lnkd.in/gEzmaFS4

Who is Derlen Chiu?

Derlen is a VP of Product at April, a tax software made for accounting agencies but designed to provide an amazing end-customer experience.

Before April, Derlen was part of the financial services industry, where he eventually began working in products at places like Plaid!

Interesting Fact: He also maintains a 14-year-old blog on the soccer business at TheSoccerCEO.com!

Don't forget to subscribe to the LinkedIn page The Way of Product | A Podcast on Product Team Collaboration for clips, new releases, and updates!

Connect with Derlen: https://www.linkedin.com/in/derlen/

Follow April: https://www.linkedin.com/company/apriltax/

02:04 Guest's Journey from Finance to Tech

04:30 Understanding the Role of Product Management

07:54 The Importance of Defining the Game in Product Management

10:21 The Role of Strategy in Product Management

18:20 Resolving Creative Tension in Product Teams

20:03 Incorporating Subject Matter Experts in Product Design

22:28 Practical Example: Automating Payments in Agriculture

23:25 The Role of Product Managers

23:57 Driving the Tax Filing Product

24:55 Balancing Roles in Product Development

25:18 Switching Drivers in Product Management

26:04 The Game Metaphor in Product Management

26:34 Understanding the Role in the Game

26:38 Tracking Product Development

27:57 The Role of Design in Product Success

28:47 The Marty Cagan Model 

29:31 Understanding When to Drive as a Designer

31:13 The Game of Product Management

31:58 The Challenge of Entering the Tax Market

32:44 The Strategic Challenge in Product Design

33:46 The Role of User Experience in Product Success

38:00 The Importance of Building Relationships in Agriculture

42:04 Closing Thoughts on Product and Design Partnership

42:49 Final Words and Sign Off

Connect with Danny: https://www.linkedin.com/in/danny-morrow/

Careers at Extend: https://www.paywithextend.com/careers

Subscribe to the Way of Product Newsletter: www.wayofproduct.com

00:36 The Journey from CTO to Chief Innovation Officer

03:12 The Role of a Chief Innovation Officer

03:22 The Intersection of Design and Technology

03:59 The Evolution of a Career in Technology

04:31 Building a Team and a Company Culture

05:13 The Role of Creativity in Technology

10:13 The Journey to Founding Extend

11:09 The Challenges and Rewards of Starting a Company

11:58 The Importance of Curiosity and Learning in a Startup

12:13 The Magic of Design and Technology

21:58 The Story of Extend's Inception

26:52 The Importance of Founder-Market Fit

28:40 The Excitement of Learning a New Industry

29:22 The Importance of Building a Strong Team

30:27 The Art of Delegation and Trust

32:48 Building a Positive Company Culture

34:11 The Evolution of a Startup

38:09 The Role of Creativity in Business

40:55 The Journey of Building a Product

43:15 The Importance of Feedback and Continuous Improvement

46:17 The Process of Marketing and Sales

54:56 Reflections on the Journey and the Future

wayofproduct.com

If so, join my newsletter at wayofproduct.com! My podcast is now focused on book research, and I want to share my progress with you. By subscribing, you'll get free updates on the book and receive a draft of the introduction sent to your inbox.

Don't miss out on this opportunity to be the first to know about my book's progress and any other project I have lined up.

Join the newsletter now at wayofproduct.com!

In this episode, I chat about the UX Architect role and what it entails with Jeremy Miller, a UX architect for GE Aerospace.

Connect with Jeremy

Jeremy's podcast "Beyond UX Design"

• The future of knowledge management.


• Difference between research reports and an insight repository.


• What the Dualo team is doing to close the insights/decisions gap.

Connect with Nick

Connect with Dan

Learn more about Dualo's insights repository product

Today I chat with Larry Cheng about how to progress in the IC path, and what is required on the staff designer career trajectory.

Connect with Larry

In this episode, I chat with the CEO and Founder of Mobilo, a smart business card about evaluating pain points and how to be decisive in your product roadmap.

Connect with Pieter

Learn more about Mobilo

For the 100th episode of the show, I'm bringing my friend and longtime coworker Clay Walter to talk about his growth into the VP of Design role.

We discuss what you have to unlearn to become influential as a designer in your org and what is looked for in a VP of Design.

Connect with Clay

We talk about abandoning the term designer in favor of "product development specialist" and what we need to focus on to increase the odds of success for our product in the market.

Learn more about Design 1st

My guest is Justin Tan, Cofounder and Design Leader at Turtle Design.

In this episode, we chat about helping companies get the right design hires for any stage of growth.

Connect with Justin

Turtle Design

Connect with Noam

In this episode, we talk about the most proven and effective style of management: Coaching.

Connect with Jared

Anjali Deswandikar talks about hiring and establishing a design culture. We discuss diversity and how to foster it and scale something larger than yourself.

Connect with Anjali

Buy "The Laws of Creativity"

Connect with Joey

If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect with Anthony: https://www.linkedin.com/in/anthonyarmendariz/

Work at Funsize: https://www.linkedin.com/company/funsize/

Listen to Anthony's podcast



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect with Richie: https://www.linkedin.com/in/richielokay/

Work at Wunderkind: https://www.wunderkind.co/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect with Peter: https://www.linkedin.com/in/peterloving/

Work with UserActive

If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect with Ian: https://www.linkedin.com/in/ianpeterman/



Work with the Peterman Firm



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Download Fathom 



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect with Pek: https://www.linkedin.com/in/pekpongpaet/

Careers at Impekable: https://www.impekable.com/



Listen to Pek's Podcast 



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

In this episode I learn about excelling in your career by talking to Taylor Palmer.

Taylor has found that he grows most quickly on teams and in environment where there is a culture of experimentation. He tries to set aside 20% of his time to always be working on something that's not on the roadmap.

Taylor has had a steep growth curve since starting at Lucid fresh out of college. Within 5 years he became a director of UX there, and helped build a team of 20 designers. He also started an awesome side project called UX tools which is now the go-to resource for showing the top UX tools in the industry. 

Connect with Taylor: https://www.linkedin.com/in/taylor-palmer-6264a171/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

In this episode, I talk with co-creator of UX tools, Jordan Bowman, about the real day to day of a product designer. 

We discuss:

-The job is not a linear process, so your methods change based on the problem.

-The best way to learn about UX, by breaking down methods and using scenarios to practice them.



-How to do consistent customer interviews by reducing your planning to a single focus you need solved right now. 

Connect with Jordan: https://www.linkedin.com/in/jrdnbwmn/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

William talks about how he learned to take control of his career from that day forward, so it no longer took "3 months" to find a new job.

William is the author of "101 Random UX Facts" and a Senior Designer at PayPal and former designer at Home Depot. This episode is a masterclass on hustling to get better career prospects. 

Get Williams book: https://101randomuxtips.com/



Connect with William: https://www.linkedin.com/in/williamntim/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

I chat with Bobby Lloyd, a Principal at United Health and a former UX/UI Strategist at Goldman Sachs, about what needs to happen to become relaxed as a designer.

Bobby calls it being "organic" and a lot of it has to do with practice and getting over imposter syndrome. We dive deep in this one. 

Connect with Bobby: https://www.linkedin.com/in/bobby-lloyd-52a8b35/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Find Janet here: https://www.linkedin.com/in/janplee/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

George Serediuc is a Principal Designer based in Romania. He runs a consultancy gig to help companies & institutions build inclusive digital products that are purposeful & human-centered. 

We talk about the philosophy of user-centered design and I make a prediction of the end of free trials, as more regulation is created in digital products. Connect with George: https://www.linkedin.com/in/georgeserediuc/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

I bring on an old guest, Bryan Mortensen, to talk about our recent discussions on why we both are considering moving into Product Managment one day. 

We discuss designers losing influence at the business seat of the table, how product management is taking over aspects of design thinking we both like doing, and why having a solid PM is a game changer for a company.  

Connect with Bryan: https://www.linkedin.com/in/bryanmortensen/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Carey Jenkins is CEO of Substantial, a world-class product development studio based in Seattle, serving a diverse set of clients - from Fortune 50s like Google and Amazon to emerging start-ups and social impact organizations. (They are also hiring remote friendly positions) 

Connect with Carey here: https://www.linkedin.com/in/careyvjenkins/

Check out Careers at Substantial Here: https://substantial.com/careers



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

In this episode, I chat about the pitfalls of UX's rising popularity with Michael Tinglin. We also talk about the non-linear career, which is giving yourself the freedom to jump back and forth between IC and management roles as a design professional. 

Michael has a lifetime of experience in the field, and provides some awesome nuggets of wisdom based off his decades of experiences working on innovative products and services for companies like 7-Eleven and Fanny Mae.

Connect with Michael here: https://www.linkedin.com/in/michaeltinglin/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

- If all design leaders have everything together.

- Leadership and Culture lessons.

- Diversity.



Connect with Adam here: https://www.linkedin.com/in/adamfp/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect with Terrell: https://www.linkedin.com/in/terellcobb/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Patricia is a content designer on Intuit's Platform Design team, and shares what the design challenges are in a platform environment. 

Anyone interested in how design contributes to huge architectural efforts should give this a listen. 

Connect with Patricia: https://www.linkedin.com/in/patriciabdwyer/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect with Tian: https://www.linkedin.com/in/tntyzhao/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

We talk about what it takes to actually solve complex problems, how to map complex problems and how to effectively plan your work for maximum impact. 

Find next level UX here: https://www.nextlevelux.me/



Connect with Drew:  https://www.linkedin.com/in/abridewell/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.

Connect Johnathan: https://www.linkedin.com/in/jonathanshariat/



Buy Tragic Design: https://www.tragicdesign.com/



If you get any value out of this show, or if it has helped you in any way, please subscribe to “Thinking Out Loud About Design” for free to get the distilled learnings on being a staff-level individual contributor.