James Sherrett reflects on a career largely shaped by the “tech lottery game” of compensation: salary plus stock options. He spent his early work years in late-1990s online finance media, then in roles helping companies adapt to the internet, then six years running a startup that failed. What did he learn? He declines to disclose his Slack earnings. A number is less interesting than understanding how the game works. Then he describes how outcomes of the Tech Lottery Game vary based on factors like teammates, investors, fundraising strength, and especially cap tables (share counts, ownership distribution, liquidation preferences, and complex clauses). He compares Slack’s cap table and $27.7B Salesforce acquisition with Mobify’s tangled cap table. He concludes that money is a startup “MacGuffin.” Day-to-day motivation came from teammates, customers, and doing quality work.

00:00 Money And startups

01:25 Salary plus options

02:15 No upside to sharing numbers

03:29 Learning the Tech Lottery Game

05:09 Spotting rocket ships

06:07 Cap table basics

08:06 Comparing two acquisition outcomes

09:23 Champagne Problems

10:53 Money as MacGuffin

12:43 What really motivates

14:50 Thank you very much

James Sherrett reflects on unresolved questions from A Slack Story: the role of luck in Slack’s and his own success, culture versus people as drivers of performance, and how to leave before it’s time by building a life to move toward. He argues luck is unknowable but significant. He quotes Michael Lewis on success being rationalized and luck creating obligation to the unlucky. He notes Slack benefited from launching at the right moment amid enabling technologies and market conditions. On culture versus people, he rejects a zero-sum framing, describing a reinforcing cycle where great people build culture and culture attracts great people. He recounts growing less motivated by Slack’s scale and achievements, defining new goals largely outside work. He tells a pre-pandemic story that helped with his decision to leave and plan life after Slack.

01:38 Luck in Slack's success

04:26 Luck lessons in life

06:34 Culture versus people is the wrong framing

08:26 People build the flywheel

09:35 Leaving before it's time

10:54 Seeking a life after Slack

12:28 Farewell to all that

James Sherrett reflects on leaving Slack on June 5, 2020, exactly seven years after joining as the ninth employee, during which Slack grew from $0 revenue and eight employees to over 2,200 employees in 16 offices and nearly $1B in revenue as a NYSE-listed company. He recounts early marketing and positioning work (“Be less busy”), the 2013 invite launch that drew 8,000 signups in 24 hours, early customer development and support, and the shift into account management and the 2014 paid launch with credits, invoicing, and the “Fair Billing Policy.” He describes building teams, opening Slack’s EMEA office in Dublin in 2015, and later leading Executive Briefing Centres and Innovation Tours. He leaves to prioritize the rest of his life, pursuing advisory work, writing, personal projects, and volunteering.

00:00 A farewell to Slack

02:06 Why I had to leave

04:22 Thank You, Slack letter

05:36 Joining as marketer

06:49 Positioning Be less busy

07:55 Launch day signups

09:00 Customer feedback loop

14:00 Saying No Nicely

17:35 Account Management begins

17:55 Paid launch and billing

20:35 Offsite, swag and scale

22:44 Enterprise sales emerges

25:00 Building the Dublin office

28:54 Culture and hiring in EMEA

32:39 Scaling EMEA sales

34:35 Executive Briefing Centers

35:52 Innovation Tours program

38:35 Gratitude and next chapter

41:35 Final reflections and farewell

James Sherrett continues A Slack Story with 3 stories he hadn't told yet. First, how Slack launched its customer conference, Frontiers, starting in 2017 after customers began asking for it. He explains how the conference brought together customers, partners, product, and the Slack team, and how it created business urgency by serving as a deadline, including an on-site executive briefing program by 2019. He shares vivid details from Frontiers and the event’s “Frontiers” name inspiration from a Carl Sagan quote about humanity needing a frontier, noting omitted lines about knowing how to reach “a new world next door.” Second, he recounts a January 2020 warning from his boss, Marnie, that he was trending toward a performance improvement plan. Third, Sherrett reflects on accepting less ambition as he played smaller roles as Slack hired world-class experts to replace functions he initially led. He reframing his trajectory as a generalist pioneer who starts new initiatives until others can do them better. He emphasizes humility, change (“burn the metaphorical boats”), and the value of never underestimating sheer gall. He closes with some thoughts about self-awareness, challenge and selling out to do be the best you possible.

00:00 Intro and Feedback

00:40 Why companies host conferences

01:44 Building Slack Frontiers

03:09 Frontiers moments and meaning

05:11 Almost on a PIP

06:38 Resetting from complacency

07:37 Learning to accept less ambition

10:20 A generalist mindset

12:26 Never underestimate sheer gall

14:06 Finding some self awareness

James Sherrett recounts Slack’s direct public offering (DPO) on June 20, 2019, when shares began trading on the New York Stock Exchange under the ticker WORK, roughly five years after Slack’s first revenue and at a valuation north of $20 billion. Instead of being in New York, he was on a family trip in West Yellowstone with spotty internet, balancing work with family. He describes placing insider sell orders the night before, the DPO mechanics versus an IPO (including immediate insider trading flexibility but greater pricing uncertainty), and a launch-morning panic when his orders hadn’t saved. After spending the day offline biking and exploring with his son, he later catches up on headlines and teammate photos from the NYSE. Sherrett shares Butterfield’s framing of going public as a rite of passage rather than the journey’s peak, then reflects on questions he later received about whether money changed Slack, noting it did through growth, new people, increased conservatism, and intensified competition (especially with Microsoft Teams), while much of Slack’s spirit and customer focus remained. He concludes that the changes weren’t all positive but were overwhelmingly so from his perspective, and teases future stories about finding frontiers, and accepting less ambition.

00:00 Slack goes public as WORK

01:28 Choosing Yellowstone over the NYSE: family, FOMO, and the trip out

03:28 The night before: placing orders and feeling the stakes

04:13 DPO vs IPO: why Slack took the direct listing route

06:09 Launch morning panic: scrambling and the opening bell

07:13 Wall Street movie moment: how the price of WORK got set

08:51 Unreal meets reality: orders fill and WORK starts trading

10:06 Offline celebration: bikes, rivers, and a day away from the news

13:03 Did money change Slack?

15:47 Closing thoughts: next on the journey

In this episode, James Sherrett shares how he created unconventional company swag for Slack. From initial inspiration at Heathrow Airport to collaborating with suppliers and distributing pocket squares as multi-purpose swag, he explores the impact and reception of these stylish silk squares. This off-the-books project showcases the playfulness and high standards Slack aspired to in its executive programs. Sherrett reflects on the innovative culture at Slack, the sense of autonomy, and the joy of injecting a sense of play into his work, all while hinting at future episodes on significant milestones like Slack's public offering.

00:00 Introduction: A Slack Story by James Sherrett

00:05 The birth of the pocket square idea

00:43 Finding the right design

01:51 Partnering with Monsoon Corporate Gifts

02:43 The arrival and reactions

03:24 Covert Marketing operations

04:07 Spreading the pocket squares

06:06 Broader swag strategy

06:55 Standards and challenges

08:50 Conclusion: embracing play and change

James Sherrett narrates the journey of how Slack capitalized on the rising demand for Innovation Tours, turning it into a valuable business opportunity. Initially uncertain about the concept, Slack learned that Innovation Tours vary greatly, with companies, government agencies, consulting firms, and specialized tour companies organizing them. By assessing the benefits of these tours through a decision matrix, Slack hosted tailored visits, sharing their company culture and innovative practices. These tours increased visibility and led to significant business deals. Ultimately, the Innovation Tours fostered collaboration and showcased Slack as a leader in enabling organizational change.

00:00 Introduction: A Slack Story by James Sherrett

00:19 The concept of Innovation Tours

00:54 Understanding the demand for Innovation Tours

01:48 Different types of Innovation Tours

03:26 The value of Innovation Tours?

05:19 Slack's approach to Innovation Tours

06:53 A decision matrix for Innovation Tours

09:37 A memorable Innovation Tour experience

14:53 Lessons from Building a Culture of Innovation

18:37 The Impact of Innovation Tours

James Sherrett discusses some common frustrations with meetings and argues for their potential efficiency when conducted properly. By exploring Slack's approach to transforming meetings into executive briefings, he demonstrates how thoughtful execution can drive business success. He highlights the collaboration between Slack's sales teams, Slack executives, and Slack customers to create effective briefings that help close deals. Key results of Slack's briefing process include a higher win rate for deals and significant contributions to annual contract value.

00:00 Introduction: the dreaded meeting

00:57 The case for effective meetings

01:23 Human nature and meetings

03:31 Steps to better ,eetings

05:04 Reinventing meetings as briefings

05:44 Collaborating with our 3 key groups

08:08 Examples of successful briefings

13:37 Results and reflections

15:33 Conclusion: finding competitive advantages in plain sight

James Sherrett shares his journey of becoming a Senior Technology Strategist at Slack, a role he describes as initially undefined and nebulous. He recounts how he took on the challenge of defining his new role, like with his previous positions at the company. Sherrett outlines the three primary responsibilities he eventually took on: executive briefing center engagements, investor and partner engagements, and innovation tours. Were there personal and professional hurdles? Some. Frequent travel and the need for self-sufficiency on the road. Sherrett's tries to capture the nuance of becoming 'the Slack man' though he never talked about it. He highlights the importance of presenting a coherent future vision, drawing from experiences and lessons in executive engagement. The episode concludes with a teaser on exploring these executive briefings and the balance between vision and reality.

00:00 Introduction: becoming a Senior Technology Strategist

01:19 Defining the role: challenges and opportunities

02:28 Establishing the hob: Executive Briefings and public speaking

03:11 A Portfolio of Activities

04:49 Embracing the Slack Man identity

06:38 Life on the road and time alone

09:40 Changing beliefs and behaviors

11:59 Selling the Future: lessons from Microsoft

13:36 Conclusion: Working on Slack vision for the future

James Sherrett recounts his return to Vancouver and Slack YVR on Canada Day, 2017. Slack YVR is familiar yet changed, with growth from 1 to 3 floors. We spend some time on the exceptional team that made Slack special, the culture, shared mission, and collaboration that fostered excellence within Slack. Key employees advanced within the company. How Slack YVR uniquely provided perspective and a focus on deeper work.

00:00 Returning to Vancouver: a new beginning

02:40 Settling back into Slack YVR

04:25 The people of Slack: at the heart of the company

07:37 Growth and expansion: Slack's global journey

10:18 Balancing work and travel

11:39 Building new programs and enjoying the work

After years of team management, James Sherrett finds himself reporting directly to a new, new, new, new boss, Marnie, while no longer managing a team. This transition leads James to explore the world of Executive Programs and Executive Briefing Centres (EBCs), specialized facilities for hosting executives. James learns to adapt to his new role, focusing on building relationships within sales teams, speaking at various industry conferences, and running executive briefing sessions to advance Slack's business goals. Throughout the script, James highlights key strategies, such as thorough preparation for meetings and public speaking engagements, and emphasizes the importance of learning by doing, illustrating his journey from Dublin to various global cities to advance Slack's outreach and impact.

00:05 New boss, new role: adjusting to changes

02:02 Embracing the essentials and finding core responsibilities

02:59 A tour through Executive Programs

07:29 Public speaking and representing Slack

09:49 The pickle of setting: work and location not aligning

15:08 Learning by coing: leading EBCs in London

17:50 Conclusion: returning to Vancouver

James Sherrett shares his experience working at Slack and living in Ireland from 2015 to 2017, highlighting both personal and societal changes. He observes Ireland's transformation with the legalization of same-sex marriage and a movement to repeal the abortion ban. He shares his family's daily life while he worked at Slack Dublin, noting the company's growth and shift to a sales-focused culture. James reflects on his own career challenges, including hiring a career coach. He emphasizes the importance of people in both his professional and personal life, cherishing the connections made during his time in Ireland.

00:00 Introduction: An Irish Goodbye

00:19 Social changes in Ireland

01:26 Reflections on religion and society

02:48 Brexit and its impact on Ireland

03:28 Personal and professional growth

03:56 Slack Dublin: growth and transition

05:27 It's the people

08:43 Moving forward: new role and reflections

In this episode, James Sherrett tells the story of Slack's journey in launching the Enterprise Grid product. Through a metaphor inspired by Lego platform sheets, Stewart Butterfield, Slack's co-founder, envisioned connecting multiple Slack workspaces to form an interlinked network. The episode explores the motivations behind this new product, including demands from existing and prospective large customers as well as Slack's own growth needs. Sherrett highlights the challenges and changes faced by Slack in appealing to 'BigCos,' such as increased security features and compliance requirements. This shift involved balancing Slack’s original values with those required by large enterprises, ultimately transforming Slack's product offerings and positioning it for substantial growth.

00:00 Introduction to Slack's Enterprise Journey

00:29 The metaphor of Enterprise Grid

01:32 Challenges with large customers

05:43 Prospective customer needs

08:33 Slack's needs and market strategy

10:22 The launch of Enterprise Grid

11:54 Values and technological shifts

14:05 Holistic vs. Prescriptive technologies

17:12 The impact of Enterprise Grid on Slack

18:53 Conclusion and future outlook

In this episode, James Sherrett delves into the starting values of the Slack product and how those values evolved over time. With personal anecdotes and a model of technology from Ursula Franklin's The real World of Technology, James focuses on 3 values of "the system of Slack": default to trust and openness, a shared reality and compassion through service. How were each of these connected to Slack's design and reflecting the original team’s work philosophy? Then, how did they change over time?

00:00 Introduction: The Values of Slack

00:59 The shift to product values

02:01 Personal reflections and Dublin insights

03:55 Technology and its broader context

07:40 The System of Slack

09:20 3 values of the System of Slack

09:49 Default to trust and openness

12:35 A shared reality through channels

15:07 Delivering compassion through service

19:50 Adapting to larger customers

21:10 What to expect in part 2

In this episode, James Sherrett recounts his first Christmas in Ireland, some family traditions and a memorable encounter with Irish neighbors. After being invited for a holiday drink, we discovered the true essence of Irish coffee, a far cry from the mediocre versions previously known. We leave with a deliciously rich and savory homemade Irish coffee recipe. We repatriate the recipe to Canada and it becomes a tradition for family and friends. The episode concludes with the Irish coffee recipe and a cautionary note on moderation.

00:00 Introduction: A Irish Irish coffee tale

00:18 Settling into Irish life

01:20 Meeting the beighbors

03:35 A memorable afternoon

04:43 The perfect Irish Irish coffee recipe

07:07 Serving recommendations

James Sherrett recounts his experience establishing Slack's EMEA offices in Dublin and London. He reflects on his journey, which included recruiting and training his team, finding new office spaces, and scaling the business from 30 to 120 employees. Sherrett focuses on the leadership transition, detailing his meetings with prospective candidates, especially Johan Butting, who eventually succeeded him. And then what?

00:13 Opening Slack's EMEA offices

01:28 Meeting potential new leaders

03:24 Always building, building, building the team

04:07 Rooftop restaurants

08:12 New Dublin office acreage

10:25 Official Search for a New Leader

12:48 Conclusion: Next Steps and Irish Coffees

In this episode, James Sherrett narrates the story of establishing Slack's London office, detailing the company's strategic growth and the beginning of its Customer Success practices. Starting with the first hire, Rav Daliwhal, James recounts the early challenges of locating suitable London office space and adapting to the emerging field of customer success. The narrative explores the evolving complexity of Slack's sales teams, reflecting on the company's gentrification and organizational changes. Significant customer acquisitions, office expansions, and the shift from a startup mentality to a structured enterprise come up. James also shares personal insights about the mistakes he made during this growth phase, shedding light on changes in hiring practices and the balancing act between retaining Slack's unique culture and striving for growth. The episode concludes with a teaser on prospecting candidates and further developments in Dublin.

00:00 Introduction: The Slack London Story Begins

00:25 Meeting Rav Dal: The Start of Customer Success

02:21 Establishing Slack London: Challenges and Growth

02:51 The WeWork Experience: Pros and Cons

04:13 Building the Team: New Hires and Roles

04:58 Growing Pains: Transitioning to a Sales Team

06:25 Major Clients and Customization

08:37 Office Expansion: Moving to Ying House

12:50 Reflections on Leadership and Hiring Mistakes

21:58 Conclusion: Embracing Change and Growth

James Sherrett narrates the journey to various European cities, from Dublin to London, Paris, and beyond, to promote and expand Slack. He details the challenges and successes of targeting tech-forward organizations, adapting to the unique nuances of over 20 smaller markets, and overcoming skepticism towards new, US technology. Sherrett emphasizes the importance of talking with customers, shares anecdotes from his travels, highlights internal challenges with hiring, and discusses balancing work with family life. This episode captures some key moments of the mission to introduce Slack to Europe.

00:23 Taking on the Mission: Spreading the Word About Slack

01:43 Carving off European markets: challenges and opportunities

02:33 Establishing a presence in London

03:33 Customer Success stories: Sky News, Ocado, and more

04:18 Hiring challenges and cultural insights

04:49 Meeting GE in Cardiff

06:20 TechCracker conference at Stirling Castle in Scotland

13:44 Struggling with work and family during travel

14:59 Reflections and personal sacrifices

16:22 Conclusion: the shared mission

In this episode, James Sherrett narrates the journey of Slack in its formative years, focusing on the challenge of hiring a VP of Sales. As the company moved beyond its development-driven roots, it realized the need for an experienced leader who could steer the Sales strategy. Despite internal skepticism about Sales, the team embarked on a rigorous interview process, eventually landing on a top 1 candidate, Bob Frati. Bob's readiness to learn and adapt made him a strong fit, and marked a key turning point in Slack's strategy to scale up its Sales functions. This episode is full of the growing pains and excitement of evolving from a startup to a larger commercial entity.

00:23 The Challenge of Hiring a New Boss

01:46 Internal Struggles and Realizations

06:12 The Search for the Right Candidate

10:19 Interviewing Bob: A Standout Candidate

14:47 Bob's Impact and the Future of Slack

15:47 Conclusion: Expanding Horizons

James Sherrett narrates Slack's realization we needed to grow up. But what did that mean? And how did we scale up our sales organization to match the increasingly complex demands of larger customers without losing what made the experience excellent for customers. Sherrett recalls some of challenges faced, solutions implemented, and pivotal decisions made. Key moments include adding specialized roles like solution engineers and customer success managers, then evolving our internal identity during an offsite meeting.

00:17 Facing the need to grow up

03:22 Preparing for change: the latest offsite

04:29 Defining a team identity

07:28 Competency traps and customer matching

12:03 Sales Math: Oh, look, customer expectations

13:49 Becoming Sales finally, an anti-climax

15:34 Conclusion: Hello world

Slack's had its Dublin office, the first outside the Pacific Time zone. Now Slack CEO, Stewart Butterfield, came calling. Also: Hallowe'en. Also: Callowe'en. We reflect on Stewart's growing role and influence both within and outside Slack, including the 'cult of personality' surrounding him. The story finishes by contrasting Slack's values with those of Salesforce after the acquisition.

00:00 Introduction: A Slack Story by James Sherrett

00:48 Halloween in Dublin: riding the leprechaun

01:25 Preparing for Stewart's visit

03:04 All Hands meeting from Dublin

06:13 Changes happening for Stewart and Slack's culture

08:33 The One Mind theory of startups

11:05 Style and substance and sprezzatura

13:40 The Salesforce acquisition and cultural mismatch

James Sherrett recounts his experience of building Slack's team in Dublin from three to 62 employees over 27 months. The journey involved adapting recruitment strategies, localizing the hiring process, and selling Slack to prospective employees alongside customers.

Sherrett highlights the initial successes and subsequent challenges in hiring the right talent, including notable hires like Alia Lamadaar, Paul Murray, and others. He reflects on some of the lessons learned and the unique qualities that made Slack's Dublin team successful. He touches on local recruitment methods, including challengine recruiters and seeking employee referrals, that eventually led to a promising Slack Dublin.

00:00 Introduction: A Slack Story by James Sherrett

00:18 Building the team: from 3 to 62 in Dublin

00:53 The transposed hiring process: screening and interviewing

01:52 Selling Slack to candidates

04:30 Challenges in recruitment

05:56 Adapting Slack to Ireland

08:14 Success stories: small wins and first 5 key hires

11:48 A little from column A, a little from column B

12:11 Walking and talking: the Ciaran Chaney experience

14:36 Conclusion: Slack is made of people

1:22 — Meeting the Irish Prime Minister, cultural observations

2:32 — Media questions: jobs, hiring, and Ireland’s expectations

3:01 — The importance of PR and community in Slack’s early success

3:30 — Expanding the story for a broader audience, tech status in Europe

4:52 — Slack’s recognition in different cities and challenges in Europe

5:24 — What is Slack? Shifting the story to employment and growth

6:02 — Tech industry size in Dublin, yet battling local skepticism

6:49 — Outline of Slack’s European expansion strategy

7:16 — Building teams, market groupings, and EMEA offices

7:43 — Lessons in global market sizing and Europe’s complexity

8:10 — The US market advantage, cultural unity

9:02 — Pockets of Slack adoption in Sweden, Lithuania, Russia, UK

9:23 — Challenges in less receptive European markets

10:13 — Meeting LVMH in Paris, cultural nuances

10:49 — Berlin IT conference: demos, user engagement, and presentations

12:55 — Frankfurt: learning from German family businesses (Tand)

13:09 — Selling to skeptics, Bosch, Volkswagen, and progressivism

13:31 — Flashbacks to early Slack days, present challenges

13:52 — Helping customers build internal cases for Slack

14:12 — Presenting to a secretive client in London

14:33 — The Sovereign Military Order of Malta: unique client, no deal

14:56 — Realization: being used for a “bake off,” lessons learned

15:22 — Lessons: pre-qualify opportunities, know your customer

16:24 — Hostility to new software, communication concerns

16:47 — Relational tactics: comparing Slack to texting and news alerts

17:08 — The Maya principle: recalibrating “most advanced yet acceptable”

17:30 — Flailing, finding footing, and sales challenges in EMEA

18:09 — Next challenges: hiring expertise to change the leaderboard

18:30 — Bonus story: interviewing Ciaran Cheney, Slack’s future office manager

19:13 — Ciaran’s hiring, celebration at The Long Hall

20:09 — Looking ahead: hiring Irish hybrids, finding and addressing biases

00:30 — Adjusting to a new city: Finding housing, coffee shops, and routines.

00:54 — Working from the Guinness Storehouse, feeling like a traveler.

01:21 — Balancing old and new: Letting go of Vancouver responsibilities, focusing on Dublin.

01:41 — "Culture Carrier" role: What it means and why it matters to a new office.

02:51 — The many hats of Culture Carriers.

03:16 — Translating company culture: Connecting Slack’s values to Dublin’s context.

03:44 — Introducing Hanni: Her energy, background, and partnership.

04:33 — The Fridge Incident: The struggle to get a fridge for the new office.

06:11 — Lessons from the fridge: Teamwork, regret, and learning to see others’ needs.

08:19 — Building a Dublin office: Weekly leadership meetings, office culture, and hiring.

09:43 — The challenge of newness: Overwhelm, adaptation, and family life in Dublin.

10:11 — Appreciating colleagues: Hanni’s initiative and the value of partnership.

10:32 — Creating local culture: Adapting Slack’s values, painting the office, and working to create a sense of belonging.

11:06 — Don't call it a remit: Balancing duties with whatever it takes to succeed.

12:16 — Embracing the "yes, and" role: Flexibility, learning, and holding onto essentials.

13:21 — Up next: Preparing to launch Slack in Europe.

Arriving in Ireland, first impressions, and the legacy of the Celtic Tiger.

0:31 — The Celtic Tiger era: Irish attitudes toward the boom years and the real estate bust.

0:59 — The aftermath: Bank bailouts, national debt, and the business context we found as we moved to Ireland to open Slack’s AMEA HQ.

1:22 — Learning Irish business culture: Distrust of wealth and the influence of Catholic history.

1:55 — Money and Irish identity: Tension between enthusiasm for success and fear of collapse.

2:18 — Reading up: Michael Lewis on the Celtic Tiger and the mythic importance of land ownership.

2:42 — The Irish play the field: Land, history, and the new tech-driven boom.

3:04 — The new boom: US tech companies, Slack’s role, and Irish identity.

3:37 — Rich and poor: Tax avoidance, emigration, and the evolving Irish diaspora.

4:30 — A changed Ireland: Return migration, new opportunities, and a maturing economy.

5:25 — Dublin’s transformation: Housing shortages, digital nomads, and Slack’s diverse team.

6:24 — Irish hidden culture: Home counties, accents, and university traditions.

6:54 — Upward mobility: Dublin’s draw, real business, and the flow of venture capital.

7:38 — Tech’s impact: 10–20% of Dublin’s workforce in tech, joining a new world.

8:02 — Real estate stories: House prices before, during, and after the crash.

8:48 — Lingering effects: The Celtic Tiger’s hangover, corporate and personal taxes.

9:14 — Taxes in Ireland: High rates, deductions at source, and a sense of shared burden. An automated tax system: No returns for most, a mix of relief and helplessness.

10:04 — Playground conversations: Meeting locals, signs of a new boom.

11:45 — Exploring Dublin: Buses, the zoo, and the city’s layered history.

12:19 — Glimpses of hardship: North side poverty, abandoned buildings, and urban contrasts.

12:44 — Dublin in transition: The city’s past and future, setting up the next story.

13:20 — Closing: Thank you and a teaser for the next episode.

[0:00] Opening Slack's Dublin offices at the Guinness Storehouse.

[0:21] Reflections on the unique character of The Liberties neighborhood, its working-class history, and vibrant street life.

[0:59] Descriptions of the old Guinness warehouses, cobbled streets, and its transformation into a startup hub.

[1:45] Stories about local shops, markets, and the quirky details of daily life in Dublin.

[3:28] Discovery of a poem, "Stone upon stone upon fallen stone," stenciled on a high wall, and its connection to the area's history.

[5:23] Personal experiences navigating Dublin's winding streets, learning the city by foot and bike, and the challenges of orientation.

[6:22] Observations on the Dublin contrast between The Liberties and the more tourist-oriented city center.

[7:13] Family adventures: playgrounds, bus rides, the Dublin Zoo, and the Viking Splash tour.

[8:16] Insights into Irish culture, including local naming conventions and the spirit of the city.

[8:56] The journey of settling into a new home, embracing both the familiar and the unknown.

Next episode: Learning about Ireland, starting in Dublin, exploring its history—some well remembered, some purposefully forgotten.

00:00 — Introduction: The Big Move, a new position in Dublin, the decision to move, and the challenges ahead.

00:36 — Becoming the First and facing the unknown

The family prepares to be the first to make this kind of move at Slack, with new responsibilities and uncertainties.

01:03 — Family sacrifices

Saying yes to big changes, including my wife leaving her job and our son leaving his routine.

01:29 — Packing up and letting go

Leaving our long-time home, selling possessions, and preparing for a new life.

01:56 — Logistics and unanswered questions

Managing the move, selling items, and dealing with the unknowns about returning and succeeding in Dublin.

02:51 — Arriving in Ireland: new beginnings

Landing in Dublin, adapting to new routines, and the importance of small comforts like the family stroller / buggy.

04:12 — Farewells and reflections

Saying goodbye to colleagues, the emotions of leaving, and the support from the Slack YVR team.

05:47 — Acknowledging inequality

Reflecting on the sacrifices made, the challenges of balancing careers, and the realities of modern work and family life.

07:18 — Looking back, moving forward

Considering the decision in hindsight, the risks involved, and the desire to live and work internationally.

08:22 — Striving for balance

Securing work permits for both, making decisions together, and aiming for fairness in the family.

09:05 — On ongoing journey

Recognizing the ongoing imbalance, the hope to rebalance in the future, and the broader context of gender roles.

09:49 — Up next

A preview of what’s next: opening Slack’s Dublin office, finding poetry in the city, and gratitude for the journey.

Early mornings in Vancouver: Preparing for European calls and the excitement of working with international teams. (0:00)

The value of research: Personalizing client interactions and surprising customers with tailored insights. (0:37)

Slack’s global ambitions: The growing demand from Europe and the decision to expand internationally. (2:43)

The Dublin scouting trip: First impressions of the city, meetings with IDA Ireland, local agencies, and exploring potential office locations. (3:32)

Learning the language of international business: Acronyms, market structures, and the unique culture of Dublin’s tech scene. (6:50)

Why Dublin? Tax advantages, a strong talent pool, and a welcoming environment for tech companies. (9:01)

Comparing European options: Weighing Dublin against other cities like Amsterdam, London, Galway, and Cork. (10:24)

Deciding on Dublin: The team’s growing conviction and the practicalities of relocating. (11:32)

Exploring neighborhoods: Searching for a home, local amenities, and adapting to Dublin’s lifestyle. (12:54)

Observing Dublin’s transformation: The city’s evolving identity, social divides, and the blend of tradition and modernity. (14:07)

The family’s journey: Preparing for the move, embracing change, and reflecting on the adventure ahead. (16:07)

Conclusion: Reflections on the move and what comes next. (16:44)

In this episode, James Sherrett shares the inside story of how Slack’s culture was built and lived, focusing on the daily practices, values, and rituals that shaped the company.

Timestamps & Topics:

[0:00] Introduction

Overview of Slack’s culture journey, the four attributes, and six core values.

[1:37] What is Culture, Really?

Exploring the meaning of culture, referencing The Culture Code by Daniel Coyle.

[3:16] Slack’s Mission: SPP

The origin and impact of “Simpler, more Pleasant, and more Productive” on Slack’s daily work.

[4:39] Never Waste a Crisis

[4:39] The 2015 security breach, how Slack responded, and the values that guided the team.

[7:53] The Power of Affirmations

[7:53] The story behind the “What good shall I do this day?” sign and how small rituals reinforced culture.

[9:56] Rethinking Sales Compensation

[9:56] The debate over how to pay salespeople, insights from Drive by Dan Pink, and the evolution of Slack’s approach.

[13:07] Calle-oween: A Unique Ritual

[13:07] The tradition of dressing as CTO Cal Henderson and celebrating consistency and dedication.

[15:13] Closing Thoughts

[15:13] Reflections on culture, rituals, and the journey.

Notable Quotes & References:

• “Culture is a set of living relationships working toward a shared goal. It’s not something you are, it’s something you do.” — Daniel Coyle, The Culture Code

• “What good shall I do this day?” — Benjamin Franklin

• Insights on motivation and autonomy, mastery and purpose from Drive by Dan Pink.

Takeaways:

• Culture is more than words on a wall—it’s how values show up in everyday decisions, crises, and celebrations.

• Rituals, stories, and even small signs can reinforce shared values and purpose.

• Adapting to challenges and being willing to question industry norms are key to building a resilient, authentic culture.

This episode, 'Eating the Goat,' explores how Slack recognized and addressed rapid hiring issues and built a strong organizational culture. Slack's CEO Stewart Butterfield used the analogy of a snake eating a goat to describe the current state Slack found itself in. To solve it's problem, Slack developed its Six Slack Values — craftsmanship, empathy, thriving, courtesy, playfulness, solidarity — and created stories and onboarding processes to embed these values in daily work. Then Slack made onboarding into a force multiplier for everyone who joined in Slack's growth.

00:00 Introduction: A Slack Story by James Sheret

00:24 The Goat Analogy: Digesting Growth Challenges

04:51 Codifying Slack's Culture: The Four Attributes

05:26 Introducing the Six Slack Values

08:40 Craftsmanship: Painting the Back of the Drawer

10:09 Empathy and Courtesy: Understanding and Helping Customers

14:11 Onboarding as a Force Multiplier

17:30 Conclusion: Reflecting on Slack's Cultural Evolution

In this episode, James Sherrett shares how Slack began to define its company culture by establishing Four Slack Attributes. Learn about the challenges faced due to rapid growth and how founding personalities like Stewart Butterfield impacted the evolving culture. Sherrett recounts the creation of the four Slack attributes — smart, humble, hardworking, and collaborative — and reflects on their role in guiding (or not guiding) team behaviour. Despite being a solid step ahead, the Four Slack Attributes faced limitations and required interpretation for new members.

00:00 Introduction: The Slack Story Begins

00:07 Defining Slack's Culture: The Four Attributes

01:14 Unveiling the Four Slack Attributes

02:14 Smart: The First Attribute

03:11 Humble: The Second Attribute

04:14 Hardworking: The Third Attribute

05:08 Collaborative: The Fourth Attribute

06:18 Reflecting on the Four Attributes

07:28 The Need for Evolution

How did we start to establish a high-performance work culture at Slack? It starts by examining the company's hiring philosophy, rooted in the high expectation of doing the best work of one's life. This expectation acted as a filtering mechanism to identify optimistic and proactive candidates who embraced challenges. Dig into the internal processes and principles of the accounts team, such as decision-making using a 'trinity' of questions and the 'search first' mentality, to maintain efficiency and autonomous problem-solving. These cultural norms fostered trust, transparency, and a commitment to excellence within the team. The episode concludes with a preview of an upcoming discussion on the foundational values that underpin Slack's culture.

00:00 Introduction: A Slack Story by James Sherrett

00:20 The Slack Interview Experience

01:01 Setting High Expectations at Slack

01:46 The Challenge of Doing Your Best Work

04:39 Empowering Decision Making with the Trinity

07:21 The Power of 'Search First'

10:58 What might a Slack culture look like?

James Sherrett recounts the thrilling journey of Slack's growth and wider adoption, from everyday encounters at coffee shops to attracting celebrity investors like Jared Leto and Snoop Dogg. He discusses the company's transition into larger office spaces in San Francisco and Vancouver and touches on the cultural evolution within Slack. The episode provides a glimpse into the remarkable milestones and the increasing recognition that marked Slack's journey to becoming a billion-dollar unicorn.

00:00 Introduction: Slack's Rise to Fame

00:32 Slack in the Wild: Real-World Encounters

01:43 Celebrity Endorsements and Investments

02:41 New Office Spaces: Growth and Expansion

03:59 Defining Slack's Culture and Future

04:26 Conclusion: Building the Future of Slack

In this narrative by James Sherrett, the story unfolds about Slack achieving a billion-dollar valuation. It covers the inner workings of living through a significant fundraising announcement and the emotions and routines within the Slack team during this period.

Sherrett reflects on the sudden shift in their valuation and what it represented, accompanied by media coverage and internal reactions. The script delves into the dynamics of Slack’s growth, highlighting the importance of their PR strategy, their compelling story, and the contributions of their leadership and teams. How does it feel to become a unicorn?

00:00 Introduction: A Day in the Life at Slack

01:01 The Big News: Fundraising Announcement

02:23 Reflecting on the Billion Dollar Valuation

04:29 Understanding the Impact of Fundraising

08:26 The Role of PR in Slack's Success

11:38 Conclusion: Slack's Journey to Fame

This episode, narrated by James Sherrett, focuses on the challenges of adapting to new leadership. James recounts receiving an unexpected call from his boss, Allen Shim, Slack's CFO, informing him of his new boss, AJ. He shares his initial apprehensions, the strategic decision-making process, and the dynamics of working closely with AJ. Through detailed notes and reflections, James highlights the complexities of balancing immediate tasks with future planning in a rapidly growing startup. The narrative underscores the importance of adaptability, trust, and forward-thinking in thriving within a transformative company environment, and how these attributes did not come quickly or easily to James.

00:00 Introduction: A Slack Story by James Sherrett

00:21 The Unexpected Call

01:25 Meeting the New New Boss, AJ

02:05 Navigating Uncertainty

03:31 Reflecting on the Changes

05:10 Allen's Strategy and AJ's Role

07:10 Building the Team

07:53 AJ's Visit to Vancouver

09:08 Adapting to Change

12:34 Future Vision and Strategy

15:12 Conclusion: Lessons Maybe Learned

In this episode, James Sherrett narrates the story of how Slack hired its first five salespeople. He outlines the challenges of hiring salespeople without prior experience, the development of a candidate evaluation process inspired by Daniel Kahneman's work, and the creation of effective job descriptions. He also details a 5-step hiring process including writing assignments, presentations, interviews, and reference checks. Sherrett shares insights into the traits they looked for in candidates and the success of the hires, emphasizing their impact on Slack's growth. Finally, he reflects on the achievements and career advancements of these 5 foundational team members.

00:00 Introduction: The Slack Hiring Journey

00:21 Facing the Challenge: Hiring Salespeople

00:53 Creating an Evaluation Process

01:46 Inspired by Kahneman: Faceted Evaluation

03:28 Crafting the Perfect Job Description

06:19 The Application Process: Writing Assignments

10:48 Evaluating Written Assignments

13:54 Sales Presentations: Zoom Demos

15:46 In-Person Interviews: The Final Step

22:46 The First Five Hires

26:34 Conclusion: Reflecting on the Journey

27:19 Next Up: Selling to Enterprises

In this episode, James Sherrett covers the whirlwind journey of Slack's growth from its inception to hitting $10-million in annual recurring revenue in 8 months. He highlights the overwhelming yet exhilarating experience of managing the rapidly increasing customer base. Then how Slack identified three key customer segments—self-service users, small and medium-sized businesses, and enterprise. James previews his third role as Slack’s first Sales Manager and the key question he faced: who to hire to drive the company's explosive growth from $10-million to $100-million?

00:00 Introduction: A Slack Story by James Sherrett

00:24 The Overwhelming Growth of Slack

01:38 Hiring Help and Customer Segments

03:02 Understanding Our Customers

03:59 Identifying Customer Types

06:42 The Barbell Distribution

08:06 Preparing for Future Growth

08:35 Transition to Sales Manager

10:00 Up next: Hiring Good Hybrids

In this episode, James Sherrett shares the playful and intricate details behind the design of Slack, highlighting how the software incorporates game-like features known as Easter eggs. The narrative explores various hidden gems like custom loading messages, the self-loathing web socket error message, the story behind the introduction of the Shruggy emoticon, and the inventive use of slash commands.

Additional touches include the reordering of emojis for a positive user experience, the surprise animations hidden in the preferences section, and the user-friendly Slack bot. The episode emphasizes how these playful elements make the work communication platform engaging and delightful for users.

00:00 Introduction: The Game of Work

01:31 Easter Eggs in Slack: An Overview

01:44 Custom Loading Messages: Making Waiting Fun

03:10 Web Socket Woes: Connection Troubles

04:50 Slash Commands: Hidden Treasures

06:58 Emoji Decisions: Injecting Fun into Work

08:45 Preferences Menu: Hidden Features

10:08 Slack Bot: Your Friendly Guide

11:04 Conclusion: Share Your Favorite Easter Eggs

James Sherrett narrates the story of Slack's launch video, produced by Sandwich Video in 2014. He explains the significance of having a Sandwich video for a tech startup, detailing the video's production, the script collaboration between Slack's team and Sandwich, and the quest for a fitting title. The final title, 'So Yeah, We Tried Slack,' emerged from a key line in the video. Sherrett also mentions a sequel video created during the COVID-19 pandemic and teases future content on Slack's Easter eggs and unique features.

00:00 Introduction: The Quest for a Sandwich Video

01:21 The Making of the Video

01:52 The Title Dilemma

02:37 The Final Decision

04:04 Aftermath and Reflections

04:37 Easter Eggs in Slack

By 2014, Slack saw consistent weekly growth and recognized that once teams started using the platform, they rarely stopped. There were two main growth drivers – acquiring new customers and expanding in existing customers – and two main tensions Slack faced, particularly the hybrid use of multiple communication tools.

To address these tensions, Slack adopted three key pricing principles: simplicity for new customers, fairness for existing ones, and speed for deployment. Specific tactics like starting with a high pricing point, avoiding unlimited user deals, and offering credits instead of discounts were employed. The highlight is the fair billing policy, which ensured users were only charged for active usage, boosting customer trust and simplifying billing processes.

The story winds up with a nod to Slack's long-term approach to customer satisfaction and its impact on their sustained business growth.

00:00 Introduction: A Slack Story by James Sherrett

00:22 Understanding Slack's Growth Levers

01:12 New Customers: The First Growth Source

01:58 Expansion of Existing Customers

03:32 Tensions in Slack's Growth Model

05:50 Principles of Slack's Pricing Strategy

08:21 Tactics for Implementing Pricing Principles

15:49 The Fair Billing Policy Origin Story

21:40 Conclusion: Reflecting on Slack's Journey and Lazy Computer Programmers

In this episode, James Sherrett recounts his first offsite experience with Slack in Sonoma on May 15th, 2014. The narrative captures the early, intimate scale of Slack's global workforce of around 30 employees, the significance of in-person interactions in a remote-first company, and the excitement surrounding their burgeoning product success. Sherrett shares his initial thoughts and questions about offsites, his reflections on meeting his new boss Allen Shim, and the profound realizations about Slack's potential and future. Highlights include candid moments with colleagues and pioneering discussions on product and customer interaction, illustrating the blend of meticulous work and imaginary thinking that characterized Slack's early growth.

00:00 Introduction: A Slack Story by James Sherrett

00:27 First Offsite Experience in Sonoma

02:26 Meeting the New Boss: Allen

05:43 Getting to Know the Team

07:50 Offsite Activities and Reflections

10:11 The Future of Slack: Aspirations and Challenges

12:45 Conclusion: Embracing Change and Change and Change

James Sherrett recounts his experiences of closing early sales deals at Slack without a traditional sales team. He describes the significance of celebrating wins through dedicated Slack channels and shares a memorable story about negotiating with Sauce Labs, a customer demanding a discount. The narrative highlights the importance of understanding customer needs and being prepared for tough negotiations. Sherrett explains how these early experiences and the detailed pricing proposals were pivotal in refining Slack's approach to sales and customer success.

00:00 Introduction: A Slack Story by James Sherrett

00:19 The First Deal: Celebrating Wins

01:16 Creating the #accounts Channel

03:27 Memorable #accounts Post: Sauce Labs

05:09 The Cannon

09:32 Crafting the Perfect Pricing Proposal

18:14 Conclusion: Lessons Learned

19:28 Teaser: Up Next - Offsite in Sonoma

This episode explores how Slack effectively used Twitter to connect with its tech-savvy audience and amplify customer feedback. It details the creation and evolution of Slack's 'Wall of Love,' a curated collection of positive tweets that addressed customer objections and showcased unsolicited endorsements. The narration emphasizes the significance of customer engagement on Twitter and describes internal processes designed to maximize the surface area of the company to customer feedback.

00:00 Introduction: A Slack Story by James Sherrett

00:22 The Early Days: Twitter as a Key Platform

01:46 Playing the Twitter Game

05:23 Creating the Wall of Love

07:29 Managing and Expanding the Wall of Love

11:06 Maximizing Customer Feedback

14:30 Conclusion: The Importance of Customer Interaction

In this episode, James Sherrett shares the story of how Slack transitioned from a free to a paid product. From the early planning stages, the company knew its business model would be a B2B SaaS offering. The script details the use of credits to ease the transition for customers, and the data-driven approach that helped identify key patterns in user growth and retention. As Slack prepared for its February 12, 2014 launch, the team used customer feedback, analytics, and strategic PR to ensure a successful rollout. The episode also touches on the company's early struggles and the pivotal role of customer stories in achieving long-term success.

00:00 Introduction: Launching Paid Slack

00:23 Defining the Business Model

00:51 Customer Engagement and Feedback

02:41 Analyzing User Data

04:08 Preparing for Launch

10:14 The Launch Day

13:17 Post-Launch Reflections

18:29 Continued Growth and Customer Relations

In this episode, James Sherrett narrates the fascinating journey of how Slack created custom socks as a unique marketing tool. Starting with a small budget, the team decided to use socks featuring their tartan design as company swag. The process wasn't easy and included a 99-email thread just to finalize designs.

Despite initial challenges, the socks became immensely popular, eventually leading to orders of up to 500,000 pairs. The socks not only contributed to brand identity but also symbolized the quirky originality and growing pains of Slack as it transitioned from a startup to a large business. The narrative concludes with reflections on how the company's unique identity evolved and adapted as it grew.

00:00 The Slack Socks Story Begins

00:22 Why Socks? The Marketing Strategy

02:25 Design Challenges and Email Correspondence

05:50 The Popularity of Slack Socks

06:56 Evolving Designs and Internal Impact

10:20 Reflections on Growth and Change

13:02 Conclusion and Transition to Paid Slack

In this episode, James Sherrett starts at Slack in 2014 as full-time Director, Accounts. He discusses the evolving roles and responsibilities in a small startup environment, focusing on customer interactions, providing demos, and collecting feedback.

A key theme is the philosophy of 'saying no nicely,' both to customers and in shaping product strategies. James explores different ways to decline requests respectfully and strategically, the impact of this approach on customer satisfaction, and the overall business operations. Additionally, he touches upon the growth of Slack, its core functionalities, and how it became a pivotal tool for digital communication and teamwork.

00:00 Introduction: Starting in Accounts at Slack

01:33 Customer Interactions: Helping and Selling

02:24 The Art of Saying No Nicely

03:01 Examples of Saying No Nicely

04:50 Learning from Customer Feedback

06:37 The Philosophy of Saying No Nicely

12:24 Slack's Core Functionality in 2014

14:39 The Complexity of Messaging

15:48 Being a Guide and Guard

16:48 Saying No Nicely: A Continued Practice

17:36 Conclusion: Focus Drives Results

18:03 Up Next: Slack Socks

A quick episode to mark the transition of the story from Part 1 to Part 2. A thank you for the audience's support and feedback. A recap of the topics covered so far. A sneak peek into what's coming next, including launching Slack's paid product and creating the Slack Wall of Love. If you're reading this you likely already know about the accompanying podcast.

00:00 Introduction to the Slack Story

00:23 Transition to Part Two

00:40 Preview of Part Two

01:05 Three Things

01:36 Recap of Part One

02:40 Podcast Information

03:07 Feedback Request

03:38 Okay, onwards

In this episode, James Sherrett narrates his tumultuous journey at Slack, starting as a consultant in June 2013, navigating through periods of high demand, strategic pivots, and personal struggles. Despite initial setbacks, including a retracted job offer, James continued to show up for work. His persistence and growing alignment with the team ultimately led to his official hiring as the Director, Accounts at the end of 2013. James shares insightful anecdotes about customer engagement, internal teamwork, and the evolving dynamics of startup culture, providing a behind-the-scenes look at Slack's early days. James' wife Monique also makes an appearance to offer her perspective.

00:00 Introduction

00:28 Early Days at Slack: Joining the Team

01:32 Marketing and Customer Engagement

03:12 Scaling Up: Handling Increased Demand

03:58 The Polite Struggle for Control

07:12 A Turning Point: December 2013

11:12 Monique Shares her Perspective

22:04 Final Decision: Joining as Director, Accounts

In this episode, James Sherrett shares the insights drawn from the first 1,000 Slack invites, from September, 2013. He shares 16 key observations about user behaviour and feedback that contributed to Slack's development and positioning. Despite early challenges, these initial signals of success helped shape Slack's journey to becoming a billion-dollar company. Toward the end, we cover hindsight bias and retaining the context of those formative days. The episode provides a unique glimpse into the embryonic stages of Slack's growth.

00:00 Introduction: A Slack Story by James Sherrett

00:28 The First 1000 Slack Invites: Initial Observations

00:42 Context and Early Success

02:09 Inviting Teams and Gathering Feedback

03:35 Key Observations from the First 1,000 Invites

09:34 Reflecting on the Observations

10:26 The Journey of Slack: From Zero to Success

11:39 Conclusion: The Reality of Startup Success

In this episode, James Sherrett recounts a defining story shared by Stewart Butterfield, co-founder of Slack, about learning the importance of reputation and pride in good work at an early age. The narrative underscores the value of conscientiousness and accountability, pivotal to Slack's company culture. Stewart’s father taught him that every job bears his name, a lesson that extended into Slack's ethos. The episode explores how this principle was embedded into Slack's cultural fabric as it evolved from a small team into a larger enterprise. Next, the show will delve into early observations from Slack's first 1000 invites.

00:00 Introduction: A Slack Story by James Sheret

00:12 Defining Slack Culture Through Stories

00:20 Stewart's Childhood Lesson on Reputation

01:13 The Cord of Wood Challenge

03:27 The Importance of Craftsmanship at Slack

04:26 The Impact of Stewart's Story on Slack's Work Ethic

05:18 Reflecting on Slack's Early Days

05:49 Conclusion: Embracing Accountability and Growth

06:21 Up Next: Insights from the First 1000 Slack Invites

In this narrative, James Sherrett recounts his experiences and observations from the initial customer interactions during Slack’s early days of summer and fall of 2013. He describes his role as a silent scribe during customer calls led by Stewart, where he took notes and shared them with the team. Through interviews and demos, James learned about customer communication habits and helped shape Slack’s positioning as a messaging tool for teams rather than 'chat.' His stories illustrate the iterative process of fine-tuning the product through feedback and the importance of customer conversations in driving adoption and shaping marketing strategies. Key takeaways include the shift from observing to leading demos and the power of validating customer feedback to build a successful product.

00:00 Introduction: A Slack Story

00:25 Early Days at Slack: Listening and Learning

01:40 Customer Conversations: Building Relationships

03:37 Interview Techniques: Asking the Right Questions

09:51 Positioning Slack: Messaging vs. Chat

11:49 Live Demos: Showcasing Slack in Action

19:06 Taking the Lead: First Solo Demo

21:46 Finding a Groove: Patterns in Customer Calls

25:22 Customer Testimonials: The Power of Word of Mouth

28:07 Conclusion: Reflecting on Slack's Journey

In this episode, James Sherrett discusses how the classic text-based adventure game Zork influenced the development of Slack. By turning work into a role-playing game and drawing parallels between Zork and Slack, the team behind Slack incorporated game-like elements to improve user engagement and onboarding. A key feature, Slackbot, was modeled after text-based game mechanics, providing guidance and interaction in a familiar format. This playful and engaging approach to work helped create a unique culture at Slack and contributed to its success.

00:13 The Influence of Zork on Slack

00:34 Experiencing Zork: A Text-Based Adventure

01:11 The Challenge and Reward of Playing Zork

05:17 Zork at Slack: A Team-Building Exercise

07:36 Lessons from Zork Applied to Slack

09:32 The Role of Slackbot in Onboarding

11:27 Conclusion: Work as a Role-Playing Game

11:39 Next Steps: Engaging with Customers

In this episode, James Sheret narrates the story of Slack's initial release to the world on August 12, 2013. Facing enormous pressure, the Slack team embarked on a 'burn down' mission to prepare for launch, coordinating through daily calls and task lists. With fewer than 200 users of their free product and zero revenue, they aimed to see if people would overcome the 'suck hump' of product adoption. The episode details their meticulous preparation, including working with PR agencies and investors, focusing on acquiring influential tech blog coverage, and aiming for ambitious goals such as 25,000 site visitors and 200 new teams. The narrative also explores the status-driven nature of Silicon Valley and how Slack leveraged PR and storytelling to make an impact. As their initial goals were met, the team faced the challenge of sustaining their early success and converting signups into active users.

00:00 Introduction: The Birth of Slack

00:26 The Urgency of Launch

01:22 Preparing for Launch Day

01:42 The Burn Down List

03:42 Preview Release Strategy

04:57 Setting Ambitious Goals

05:47 Silicon Valley's Royal Court

08:37 Executing the PR Campaign

10:44 Achieving Initial Success

11:53 Reflecting on the Journey

Computer says:

This episode, based on James Sherrett's recount of Slack's journey, illustrates the challenges and strategies employed to market Slack without traditional promotional tactics.

The narrative follows the internal discussions and the creation of the essay 'We Don't Sell Saddles Here' by Stewart Butterfield, emphasizing understanding customer needs and aligning them with Slack’s value. It addresses the 'suck hump' — the initial friction users experience — and explores methods to foster user engagement and adoption. The story also highlights Slack's commitment to transforming workplace communication by shifting user beliefs and behaviors, culminating in the successful launch of their product.

00:00 Introduction: The Slack Story

00:27 Defining Slack's Marketing Challenge

00:56 Core Marketing Ideas and Strategies

02:48 Overcoming the 'Suck Hump'

05:06 Email as the Enemy

07:41 Changing Customer Beliefs and Behaviors

12:40 Preparing for Launch

And then, if we got someone interested and keen to learn more, how to answer the immediate next questions: Why should anyone care? Who was Slack for? What did Slack do for them? How did Slack work?

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The brainstorming we had done in SF at the f2f on Day 1 felt like good foundational work to me. Some ideas had started to emerge. We started to understand our problem better. But I felt like we still didn’t have a really solid solution for how to position Slack to someone starting with a fresh perspective. How to start from zero?

And how could we know if our answers to the question of What is Slack? actually worked?

We had a lot riding on whether we could accurately convey the positioning and value proposition. The product could be as amazing as possible but if we couldn’t get people to try it we would have another failure.

The stakes were high. Our survival depended on getting our positioning right.

Testing variants

To test our ideas and get some real evidence of whether they worked, we designed a pretty simple scenario. We’d try different options for answering What is Slack? and let people tell us with their actions and feedback if any of our options worked for them.

From all the ideas Stewart and I discussed we whittled our options down to 5 different concepts. Then we built 5 different landing pages focused on those concepts. Let’s call each of the 5 options a variant.

Each variant of the landing page had its own headline and positioning copy. Each was distinct enough that we felt by testing them we’d have some insight into what was going to work.

We’d measure the number of visitors and their conversion to signing up. Then we’d ask some starting questions to gather more information. That was the shape of our plan, very much drawn from principles of lean startup methodology.

To get rolling, we offered a simple call to action incentive — get $100 credit for signing up. Then to get some traffic to our variants we used Google AdWords (now Google Ads). Those ads you see on Google in response to your search? Those are AdWords in action. We created some small traffic acquisition campaigns to target broad but topical keywords.

We started to send traffic to the landing page variants, in a random order, trying to keep the traffic quality uniform so we didn’t bias any specific variant. We measured each stage of the process — clicks, visits, repeat visits, etc.

We got more confident in our process as it ran. We ramped up our traffic acquisition and found our first significant insight — a ceiling to topical keywords. Interesting! A limit existed to how many people we could invite into our process because a limit existed on how many people were doing searches on our topics. That turned out to be a good thing to know.

As the traffic started to flow, our informed guesses started to have some tangential proof against them. We started to see more patterns emerge.

That’s all pretty abstract, so I thought it would be handy to show the actual 5 variants of the landing pages. They’re below in pretty much their original state.

Landing Page 1: Team communication

Landing Page 2: Kill email

Landing Page 3: Better decisions

Landing Page 4: Infinite brain

Landing Page 5: Less busy

At the bottom of each variant of the web page was the same call to action.

When people completed the email address and company name form above by clicking the Join Now button, we presented a Thank You page. On the Thank You we added a short survey. We figured, these were interested folks who could tell us a lot that we wanted to know. Why not?

The survey was optional and provided a small extra incentive ($100 more credits) that only showed up after it was finished. We didn’t want to create pecking pigeons in a Skinner box trying to max out their credits.

Then a second Thank You page showed up with the extra $100 credit. Surprise!

This let us make a fun joke and set the tone for Slack. We were friendly. We were fun. We were going to be launching with a paid product sometime in the future. But getting in wasn’t a sure thing! So there was a bit of the “line outside the nightclub” effect we were trying to create.

So what did we learn?

If you just want to skip ahead to the answer, go for it. I’m not here to give you mandatory homework. But we could play a little game.

Here is it. If you want to try for a richer experience and to learn a bit more from Slack’s story, scroll back up. Spend a few minutes and make a few notes on your own about what you think worked from the 5 landing page variants above. What was the top performer? The bottom performer? How come?

Bonus marks for really considering the copy in the survey and landing page. Each bit of the work above got lots of scrutiny and consideration and I believe offers some good lessons. The results below will keep.

In the meantime, here are some options we considered for Slack’s logo at the time. These are to keep you busy or just to encourage you to think about the landing page variants and how they might or might not have worked:

Okay, enough stalling.

Results of our tests

First up, people responded pretty well to each of the 5 landing page variants. There were no duds that were much, much worse than the rest and that we could disqualify immediately. Hmm.

So maybe our test wasn’t a solid test of differentiation? Or maybe each of our variants had some merit and attractiveness for people? Hmm again.

Questions like these are pretty hard to answer even when you have lots of time and money and data. We had limited amounts of each of those resources. We wanted to check our work, get some proof and refine our approach. We couldn’t do deep or long research. This would have to do. We decided not to let perfect be the enemy of good enough.

So, the headline results from our landing page variants tests:

* Lowest performing was Landing Page 4: Your searchable, infinite brain. I liked the variant and the promise and I could also see why it didn’t work – too abstract to quickly understand and a step or two removed from the core pain we were trying to address. And what was an infinite brain anyway? Weird!

* Top performing, by a thin margin, was also the most inflammatory variant, Landing Page 2: Kill 75% of your email in 3 days. It was specific and hit a nerve. It had a tangible promise. It had an enemy (email) that everyone knew and no one loved. It worked to get people to sign up.

But if we moved ahead with that Kill Email positioning, where could we actually go with that promise and target?

Sure it was great to make an enemy of email and to share that enemy with everyone who had ever used a computer connected to the web. It was great to name our enemy and be willing and ready to take it on. But did we just want to stand as a negative against something? We did not.

It also begged the question that if our product was successful and reduced someone’s email by 75%, then what? What state of nirvana had we provided? We wanted to stand for something, not just against something. We wanted to run towards a promise in the future, not away from a pain in the past.

Plus, our second place variant scored very similarly and we liked it too — Landing Page 5: Be less busy. The origin of this variant was pretty much verbatim from Stewart, with a few tweaks for brevity and clarity.

And spoiler: it ended up being the copy we used on the single-page website we launched for our preview release a few weeks later, on August 14, 2013.

What we actually learned

To dig a bit deeper, with the context of our results, what did we actually learn? We got out of the building. So what?

Here are 3 of the things that informed our approach to launching Slack, beyond the simple results we measured on the landing page variants.

* Seeking an elusive answer – It proved very hard to satisfactorily answer the question: What is Slack? It was hard at the very outset and it proved consistently hard to answer throughout the company’s history. It’s messaging. It’s a replacement for email. It’s a way of working together. It’s all your tools in one place. It’s a collaboration hub. At the time it was each of those things, and yet it was more than any of them alone.

* Going for a feeling – By elevating the positioning from an answer to the questions of What is Slack? to promising a feeling Slack would deliver (Be less busy) we felt like we could appeal to a bigger, unaddressed need in people. Did they want feature X, Y and Z or did they want a feeling of calm control in their work? Intuitively we knew that feelings drove the most value for people. As a side benefit, we could work our way around the What is Slack? question to try to answer a more aspirational question: how does Slack make me feel?

* Finding a sweet spot – We definitely worked within the MAYA principle: Most Advanced Yet Acceptable. Our initial target audience were going to be tech nerds and developers like us. We wanted to provide them with a solid dose of a familiar experience they could quickly get started using, mixed with new, advanced features they wanted. “A luxury, once enjoyed, becomes a necessity,” famously noted C Northcote Parkinson, and we wanted Slack to be a necessity.

And beyond those 3 things we learned about competition. Our audience knew messaging from consumer chat applications like MSN Messenger, AOL IM and Skype and often used them for work amongst their teams. A few work-oriented messaging apps had started to show up: HipChat and FlowDock and Campfire. Each was fine and they were well adopted by tech nerds, but they seemed somewhat interchangeable.

They also positioned themselves almost exclusively through feature lists. Look at all this stuff this product can do! Look at all these specs and feature names! File sharing, mobile apps, etc., etc. We believed very clearly that while we needed features, 90% of the user experience was simple messaging, and making that really amazing made the biggest difference.

In addition, we learned about who was (and was not) seeking us. In running the AdWords campaign to find traffic for our variants test, we started to get some tangible experience marketing Slack before we actually had to market Slack. And Google provided incredibly valuable insight into aggregated market intent.

It showed us that search volume for keywords around product categories like group chat, business chat and company messaging was pretty much zero. No one was looking for the natural name for our product category. File sharing and file security had some droplets of interest but didn’t fit our product.

How about the function Slack might serve? There was search volume around role-specific areas like project management, software development and internal communications, but these were oceans of intent that included role-specific software, consultants for hire, service providers, educators and more. Perhaps our people bobbed about there, but it was too broad for Slack to swim in.

Where we thought we fit in, somewhere between the rivers of software collaboration and team communication, also felt too broad. We weren’t agile software providers, though you could certainly use Slack for an agile software methodology.

At the time of our launch, a well-trod tactic for startups was to harness existing demand and intent through search engine marketing. Unfortunately, this tactic was not going to work for us. Our market was too broad to accurately target, or too narrow to reach any scale.

It could have spelled doom that no one was searching for Slack (or Slack-like products). That certainly struck me at the time. But we chose to think the opposite. No one was searching for Slack (or Slack-like products) because they didn’t yet know a better option existed. We had to show them something better could be possible.

We knew from the existing customers already using Slack that they believed something better could be possible. They had actually tried our rough product, after all. Hope existed. And that insight from actual users made me a believer that we could find a market too, despite the evidence that seemed to spell doom. Our customers’ feedback confirmed our faith that how software teams worked together wasn’t a non-existent product category, it was instead an undiscovered product category.

And yes, I do mean specifically, “how software teams worked together” because that was the scope of our ambition at the time.

Stewart made a guesstimate of all the software teams on earth and sized the market as $100-million. Pretty big, right? If we could capture all those teams as customers, that could create a sizeable business for us. We hoped. We knew so little!

So what next? Now we knew our challenge. We knew our positioning. To stand out we had to be different. Perhaps an unorthodox tactic to get the word out? Seems about right.

Up next:

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Because washing the dishes was such a chore, each of the 3 of us (Stewart, JR and me) had our own set of cutlery that we kept on our respective desks. When one of us got fed up with the state of the office we gathered all the office dishes to be washed. It was an unspoken agreement that suited how we wanted to work.

About once a week, in the middle of the afternoon lull, one of us would boil water and spend 10 minutes on the task of washing the office dishes. I can still see Stewart up to his elbows in suds in the bathroom sink while talking with the bank on speaker phone set beside the sink.

I had stolen my set of cutlery from a restaurant whose menu featured mainly meatballs. Stewart and I ate lunch there one day. We wanted to get out of the office and have a chat. We had to start making some progress on the marketing tasks that were piling up.

As was our usual pattern, we talked about life, current tech news, travel – anything to set the stage and avoid the real thing that was on both of our minds. I liked asking him broader questions and I think he appreciated getting them. It wasn’t all work all the time. It wasn’t all “businessman things.”

Chatting more broadly gave his mind a short break, something to interrupt the hamster wheel. But the thing we were avoiding talking about was almost always the current work we were doing and how it was or wasn’t getting done.

And in general, Stewart and I hadn’t found ways to work particularly well together when we worked closely together. This came down to the fact that we each wanted control over the work. I tried to obtain that control through process. Stewart held out against the process, or rebelled against it or just generally ignored it. That made for some challenging times.

After all, I was a hired gun on a 3-month contract. He was the boss leading the company. Shouldn’t I have known better?

Silicon Valley lore

There is a classic bit of Silicon Valley lore that all entrepreneurs are missionaries. It gets repeated because it’s flattering and it also contains some portion of truth.

The classic presentation of the Missionary vs Mercenary model comes from John Doerr, the legendary venture capitalist at Kleiner Perkins, who invested in foundational tech companies like Netscape, Amazon, Intuit and Google — an amazing track record. He may have a pretty low profile in the general public but to anyone with a passing interest in the societal and commercial impact of technology, John Doerr is Silicon Valley royalty. Whole books have quite rightly been written about him, and by him.

In Doerr’s 2007 presentation to the Stanford School of Business entitled Entrepreneurs are Missionaries, he outlines his model for thinking about founders in Silicon Valley.

“…an entrepreneur does more than anyone thinks possible with less than anyone thinks possible, in whatever field they're working in, and importantly, at least for my values and those of my partners, entrepreneurs are not mercenaries. They're missionaries.”

…

“More differences between the mercenaries and the missionaries? Well, the mercenaries are opportunistic, always interested in the pitch and the deal and they're kind of sprinting for the short run. As opposed to the missionaries, who are much more strategic. They're focused on the really big idea – in forming a partnership that will last and they know that this business of innovating is something that takes a long time. They look at it more as a marathon.

The mercenary is obsessed on the competition. They create a kind of aristocracy of the founders. They're not inclusive of the rest of a team, and they're really driven by their financial statements. As opposed to their mission and value statements, for example. Or obsessing on the customers.”

The model proposed by Doerr is a classic duality. Either you’re a missionary or a mercenary. It’s black or white. Hot or cold. Left or right. You need to choose your approach (or have the approach choose you). The two approaches are in opposition to each other. The missionary is the hero.

Being a Mercenary

When I started at Slack I was a consultant trying to prove my worth. I had a 3-month contract to do. So, pretty clearly, I was a mercenary — a professional hired to do a job.

Stewart was the CEO trying to balance so many things at once, one of which was managing me, this damned marketing consultant with my questions, my ideas, my demands. As I was coming to learn, he cared so much about everything he had to do. All those “businessman things” he talked about. He knew he had to do them and he wanted them done his way, particularly any kind of public facing communication. Yes, dear reader, it would be safe to say that Stewart angled towards the missionary side of the duality.

So there were many days for me that I would characterize as wandering days — days spent wondering what I should do or could do to get the work done that I had been hired to do. It obviously needed to get done. I obviously had been hired to do it. I obviously also needed Stewart participating and onboard with my work. He had done all the marketing before I’d been hired and wanted to be deeply involved in any new marketing. And yet.

Sure, I found many things to work on in the meantime. There was no shortage of tasks that I could do. I knew how to do consultant work about process and preparation and describing the problem and proposing approaches. Not actual work. Work about prospective work and around existing work.

But my recollection of those early days at Slack is largely waiting for Stewart and waiting to get down to doing the real work I had been hired to do. I think it’s safe to say I was not a great mercenary.

The fate of meatballs

The meatball restaurant we visited went out of business or became something new before we could return. But on that one particular day we visited, alone on that particular patio, after we had gotten through our small talk, I remember eating meatballs and caesar salad with Stewart, and finding that we were in sync.

Perhaps we’d found a third way to bridge the divide between missionary and mercenary? Time would tell. I knew somehow I had to find a new way of working with him. So I was trying new things.

And it helped that by then I had some familiarity with Slack because I had been using it for hours every day. I started to see the really compelling parts of what it could offer to prospective customers. Stewart and I shared articles back and forth on ways of launching, ways of thinking about products. We had ideas we bounced off each other. We started to build a shared topography of what we could do and where we wanted to go. We started working well together.

And pretty quickly I realized we weren’t alone. We had customers. People that we knew and who turned out to really like to use Slack, once they started to use it. We started to hear back from friends and contacts we’d coerced into using Slack. They had tons of suggestions on how to improve the product, and that proved perfect. It meant they used the product and liked it enough to speak up. They were engaged. They had complaints and feedback and it felt glorious, even if they only numbered in the dozens, maybe the hundreds at the time. Despite the missing features or clunky bits, real people were using Slack and kept using Slack once they got started.

The problem was the level of coercions needed to get them started. These were the warmest prospective customers we would ever find, and it still was really hard to get them started. To compound our problem, it took multiple people to get started on Slack at the same time for it to work. As we said internally at the time, the single-player experience sucked.

So we had both the cold start problem (why would I use this if there’s nothing in here to use it with?) and the multi-user problem (who would I use this with if the people I communicate with aren’t on it?). There was a huge amount of friction to get people to begin using Slack and to get their teams using it. They had email. They had chat. They had file sharing. Another tool could be the answer?

But even before that, before we could ask people to use the product and get their teammates using the product, we had a positioning problem. The key problem I’ve mentioned before: what the heck was Slack? It wasn’t email. It wasn’t file sharing. It wasn’t project management software or help desk or task management.

All these crowded software categories existed and bulged with competitors. But we didn’t want to get slotted into those categories. It was like restaurants. Categories existed: pizza, sushi, quick service, casual family. Meatballs? We definitely didn’t want to be a failed meatball restaurant.

Our goal was something both smaller and bigger. Smaller, in that Slack needed to start out and compliment all the other software people were already using. Bigger, in that we wanted to create a whole new category of software and a better way for teams to work together.

So how do you tell people about something new that’s small and big at once? That’s new and familiar? That’s incremental to what they use but then replaces much of the functionality of those tools? How could we give people some compelling story that they could describe to someone else, and that made them look good, and got them to try our product, with all (or at least the majority) of their teammates?

We didn’t know any of those answers, yet. But we knew we had to find out or we were sunk before we’d launched. Our survival hinged on getting our story right.

In many ways, though we didn’t talk about it at the time, Slack had inherited the Glitch problem – a great experience once you experienced it, but an experience that didn’t fit into any of the existing containers in your brain.

Over meatballs on that restaurant patio, Stewart and I didn’t necessarily know the answer to the key questions, What is Slack? We had clues and ideas and needed proof outside of our collective brain space. We needed a way to learn which of our stories would work best, and we needed some proof. We needed to “get out of the building,” as Steve Blank says in Four Steps to the Epiphany.

So we came up with a way to test a bunch of positioning options and get some proof: landing pages. We’d trial our ideas away from the warmest prospective customers with the coldest ones — random people on the web.

How did we do it and what did those landing page look like and how did they perform? We’ll dig into all that in the next chapter.

Menschy

As a sidenote here, I wanted to unpack a bit more an idea I’ll come back to a few times later in this project.

Remember how I hinted at a third way of working in a startup? Not mercenary, not missionary, but something else? It’s an idea I’ve thought about a lot since my time at Slack, since I’ve had a chance to reflect on the bigger picture and how my roles fit in over the years.

And I’ve come to think there is a third way to be that I would call “menschy,” derivative of the yiddish word mensch — “an honourable person.” It’s the best word I’ve found so far to describe the best version of the role I had a chance to play.

Not a missionary. Not a mercenary. A mensch. I don’t want to dress this concept up too much or be too self aggrandizing about it, but it’s the most apt way to describe the approach that worked best. When I did my best work and when that worked served people best, I lived up to a menschy approach.

What I had to do — and what I think anyone in any situation of high uncertainty and high pressure needs to do — was find the work that needed to get done and do it as well as I could. It was to help other people — teammates, customers, prospects. It was to live up to the descriptors of a mensch — strength, integrity and honour or compassion. It was to be human and humane. That’s what I aspired to.

I wasn’t a founder. I couldn’t be a missionary. I’d joined 8 others at Slack who had all been part of the Glitch failure. That experience tempered and dedicated and bonded them to each other and to the larger mission of Slack.

And I also wasn’t a hired gun. Or, at least I didn’t want to be, though that was mostly my role to play at the time. Mercenary values didn’t feel right. I wasn’t going to go on to be a marketing consultant at other startups. I wasn’t looking for the highest bidder. I wanted to belong at Slack and really commit to making it be as good as it could be.

But I found I needed to add elements of both missionary and mercenary into my approach to make it work. I needed to have the dedication and purpose of a missionary. I needed to have the clear headedness and bloody mindedness of a mercenary. I needed to have a focus on a mission. I needed to deliver concrete results. I needed to hold on tightly. I needed to let go lightly.

I didn’t have the word menschy in the early days of Slack that I’m describing in this chapter. But I did have the feeling that I needed to find a better way to work with Stewart, and to work with the Slack team. I needed to serve the mission of the company and I needed to deliver on the goals of my contract. Was I able to balance those opposite demands?

That’s something to cover in the next chapter, where we get down to doing some of the actual work.

Up next:

Inside the glass door, I could see carpeted stairs running up to a second floor. The neighbourhood was called Yaletown and consisted of a few square blocks of renovated warehouses and narrow streets – exposed bricks, thick wooden posts and beams.

A hundred years ago it had been a train yard. Now its street level was full of bars, restaurants, hair salons, boutiques and pet boutiques. Its upper floors housed video game programmers, search engine optimization consultancies and local branch plants for Sony and Amazon and Apple. Surrounding the renovated warehouses towered glass-skinned, concrete-cored condos.

When people visited Vancouver fashionably, this was the neighbourhood they often started their visits in.

Stewart appeared along the sidewalk, in conversation on his phone. He opened the glass door and I followed him up the stairs along a carpeted corridor to the back of the building to a door with a Tiny Speck logo: 250B.

The office was about 20’ x 20’, a room with brick walls and large windows facing south. A model of a white galleon hung from the ceiling and turned out to be a kite. A mounted walrus head hung on the wall. A crocheted circle hung in the corner and read in pink stitching, B***h don’t kill my vibe.

One other person sat in the office with headphones on, typing at a computer, looking focused. Stewart placed his bag on the desk in the corner and sat on an office chair with a padded cross for a backrest. The other person in the office took off his headphones and introduced himself: “Hey, I’m JR.”

Working with Stewart

JR pointed me to the two empty desks and told me to take my pick. I set myself up and pretended for a few minutes to be getting started.

Actually, I was waiting for Stewart to get off his call. When he showed no sign of wrapping up I figured I might as well get started. I’d written a proposal for the work I was going to do. I should assume I had been right with that direction and get started doing it.

And that experience — waiting, trying to get on with the work as well as I could, checking in again — was what working with Stewart was like for the most part in those early days. He had very specific guidance to impart on everything, when he became available to impart it.

I would like to say it was easy. He was obviously incredibly bright and capable. I would like to say it was fun. We were doing hard work on great problems. But the general theme of my early days I recall as mainly a search to find direction. Stewart was super busy and direction was scarce.

Often times, when I was trying to get feedback from him, waiting for feedback from him or looking to book time with him, he’d deflect the requests. “Businessman things,” he once said to me as he shrugged, getting off a call and coming to chat. That became our shorthand for all the other things that occupied him: businessman things.

I had to just keep working on my jobs, do my best with my own judgement and wait.

First Steps to the Epiphany

When I felt stuck on what to do next, I often went back to a book written by Steve Blank called Four Steps to the Epiphany.

I had a dog-eared copy full of notes that I found really useful for structure and process at the early stages of a startup where we found ourselves. Four Steps was useful for structure because Blank had founded and built many huge B2B software companies, and the book reflected an idealized view of how he’d done it.

I’d used the tactics of the book before with good results, and we were definitely still on the first step of the four: Customer Discovery. Here’s the flow chart of the process of Customer Discovery.

The main point of all these boxes is that you need to “get out of the building,” as Blank says. And talk to customers. Test things with them. Listen.

Other times when I needed guidance on the next thing to work on I’d just put on my own businessman hat and ask: what is the next best thing for me to be doing? Or, what is the thing that the business needs me to do? I found it an effective way to get out of my own head, and any frustrations I might be having, to focus on keeping moving ahead. I wished I’d done it more when I had run my own startup.

As a result of waiting and asking what needed to be done, I ended up doing a lot of different things — researching the market, drafting positioning documents, writing website copy. Basically, trying to keep pushing to answer the key question I felt like we needed to answer – What is Slack?

This wasn’t a smooth process. I found many dead ends and I was basically trying to catch up to Stewart. Looking back, I’m sure I have some Stockholm syndrome in my recall, and some survivorship bias in my recollections. (Was it really that bad or just a circuitous way to find the right direction?) But I did learn quickly through taking initiative and either rarely making headway or commonly making mistakes. This didn’t always please my boss, but I think it did show myself and my peers that I was committed and contributing.

And to be honest, in those early days, I really had no sense of what was to come with Slack. The whole operation struck me as held together with bailing twine, dedication and gumption. The team was obviously talented and committed to each other and believed in the promise of their new product.

But I wondered: what had I gotten myself into? I had conversations in the evening with my wife about just that question and the natural follow up: where could this possibly be going? It was not clear at all Slack was headed to any success.

In my job search before agreeing to join Slack I had been close to joining other companies: a well-funded and growing software suite for lawyers called Clio, a social media monitoring company called Hootsuite. They were each prospectively offering me more money and a more mature company, further along in its product development. What, my wife rightly wondered, was the reason to join this failed game company and bet on their new, unproven, weird product called Slack?

I didn’t really have a good, coherent, well reasoned answer. But the main two things that made Slack compelling at the time were the team and the culture.

Team and culture

The reason the team was compelling is easy to unpack. They were simply way better than any team I had worked with before. They were more accomplished. They worked harder. They were smarter. They were faster. They were deeply online people who had been using the Internet and working on the web through the late 1990s and early 2000s and had extensive expertise in how it worked both technically as well as socially. They also really seemed to like each other and had terrific chemistry.

And to unpack the chemistry is really to unpack the culture. Here were people who shared the same values: fun, work, ambition, a collision of high and low brow references, an appreciation for going to the nth degree to get something just right.

They were each mildly weird and unbalanced in their own ways and happy being weird and unbalanced together. An element of fun and humour underpinned everything they did. The tone was serious and light, demanding and humane, focused and wandering, all at once. We posted a sign above the door of our modest office that became a call to ambition: More Holey Moley.

Standards for work were set really high and I responded well to that. Here were people who produced great work and could also recognize great work across domains. Here too was as close as I had come to a meritocratic culture for everyone. I realized I could make copy editing suggestions to Stewart on a piece of writing he’d sweated over, but only if my suggestions were all really well considered, packaged up in an accessible format and actually improved the end product. Praise, when it rarely came, was well earned. There were no workplace equivalents of participation medals.

(Many years later I found myself telling a group of executives I was leading on a tour of Slack’s 10-storey headquarters in San Francisco that the company had always been a liberal arts software company. When puzzled about something not working, no one felt embarrassed quoting Wittgenstein (“It is not how things are in the world that is mystical, but that it exists.”) right beside Homer Simpson ("The lesson is: never try.”). No one had to be convinced that people made decisions based on some concoction of emotion and reason, that artistry mattered as much as technical acumen. No one talked about “soft skills” as if they were on the Nice to Haves list for employees.)

And the culture of Slack came alive in its strongest way for me in those early days in written words, and how written words were evolving. The team really used their own product all day and every day, and beyond into the evenings. Everything was in Slack, organized into channels that acted as streams of communications and events and emotions and jokes.

As JR himself, my first Vancouver teammate beyond Stewart, wrote in The death of Glitch and Birth of Slack:

When I joined the company, I’d been given a crash course in how we worked together on my first day. No email. Everything happened in IRC: a chat protocol from the late 80s. We had a server set up with channels based on topics of discussion: #general for company-wide chat, #deploys for new code releases, #support-hose for inbound customer support requests, and so on.

Alongside this we added a few other things we needed. A simple FTP server which posted uploads into the #files channel. A system that wrote our chat logs to a database so we could search them and read old archives.

A set of integrations that posted updates from other systems into IRC: whenever a new user signed up for Glitch, or bought credits, or wrote in for support, it showed up in a channel. Whenever we deployed code, or got a new review on the App Store, or tweeted from our Twitter account, it showed up in a channel.

Taken together, this allowed us to communicate in real-time, share files, find anything we’d ever talked about at the company, and keep track of everything happening with the business – all while avoiding the unique 21st-century hell of email reply chains and fragmented organizational knowledge.

This was the experience I had too, and so many other early Slack employees had. They were both new to the company and the way it worked.

At first if felt disorienting and overwhelming. Then quickly the work streams became indispensable and I started dreaming in channels. I couldn’t imagine using anything else.

Channels were themed based on the work happening in the company. Anyone could jump into any channel and any conversation in any channel. This was incredibly powerful because you could read and join in any work stream. It was also an incredible responsibility because you could disrupt or derail any work stream.

For us, the channel was the canonical work stream. If something wasn’t in a channel it might as well not exist. Messages from humans and computers mingled together in channels because both were essential to the work. We quoted these messages. We quoted each other. We learned to do Slack as we were doing it. As a result, a style of writing emerged combining the best aspects of each of our individual writings. As I watched and participated, an aesthetic spread.

That’s a bit abstract, so here are some examples.

The parenthetical voice became common because we relied on writing so much that we had to accommodate and show different perspectives at once. Not including the parenthetical in an important message felt like you were making an argument but not showing your work (and I may be totally wrong here but I think it made the whole reliance-on-writing culture possible because it counterpointed and disarmed arguments and objections as well as me vs you arguments). Including the parenthetical made explicit that you had done more work than shown, and were open to other perspectives.

Searching became an expected default behaviour so that people would try to self serve their own questions. Having access to the entire history of communication of the company meant you had a responsibility to use that history. When you had a question, you learned that it was pretty unlikely to be the first time that question had ever come up. So the rule was: seek to solve first through search. Only ask for help, and tax a teammate to answer, if you couldn’t answer for yourself, or had searched and found a partial answer and wanted to confirm it or clarify.

Emojis were simply a more efficient way of acknowledging someone and providing an emotive response than writing. Plus, they were like a game too. Could you come up with a clever emoji that acted as a commentary such as 💸 when you were busy buying ads? Could you complete a 👉 👈 with a teammate in consecutive messages, like a texted high five?

Often times, we quoted things to make sure our messages were clear. (Did you mean when you said .)

We worked at mastering the simple markup syntax in Slack that let us decorate our text for meaning and to show off. We learned keyboard shortcuts to emphasize words, arrange text and build lists. To be any good at Slack the company you had to be good at Slack the product.

Playing the Slack game

When people on the team were going for lunch or getting up to do an errand they would type ‘afk 30 mins’ — meaning, away from keyboard for 30 minutes — to let teammates know they would be out or reach for half an hour. To some folks this small gesture might seem trivial or even nagging. But I found it rather charming.

Here was a team very tightly connected who consistently offered up small signals of belonging and courtesy to each other. ‘afk’ meant more than just ‘I’ll be away from my keyboard for a period of time.’ I read it was meaning ‘You may need me in the next 30 minutes and I won’t be available but I will be thereafter’ and ‘Here are some expectations I can share with you as a small sign of caring’ and even ‘I trust you to tell you what I’m doing and to provide transparency to you.’

No one mandated that we had to type ‘afk’ if we were going to be offline or unreachable. Like all great group rituals, one person started it, another saw it and imitated it, and then it became normalized as a small courtesy. It started before I arrived and I’d guess carried over into Slack from IRC.

Other chat acronyms also populated our communication — OTOH (On The Other Hand), IMHO (In My Humble Opinion) or just IMO (In My Opinion) and YMMV (Your Mileage May Vary) — as ways to humanize and soften messages. But it was afk that struck me as most representative of the type of place Slack could be.

Years later, as the company added new employees at a blistering pace, an official Slack style guide was written and included in training. New employees otherwise tended to be a bit mystified at first and hesitant to jump in to such a fast mode of working. Open felt exposing to them. Transparency felt threatening. What if they made a mistake?

But that was still many years away, and we had to sink or swim for ourselves in the meantime. We were still very much in Customer Discovery and hadn’t even considered Step 2: Customer Validation.

In short, right from Day 1, I found these Slack folks were people who read and wrote and created things in the world and loved to do so. I felt like I wanted to be one of those people rather than someone selling lawyers on revision management. I wanted to belong. These felt like what I hoped could be my people.

Up next:

Notes

Four Steps to the Epiphany is also available as a PDF from Stanford. It’s still a terrific resources for anyone considering or running a startup.

Land midmorning into glorious sunshine. Hello, California! Get the taxi to the freeway to the office to get started. Onwards to meet the team and hopefully show them and myself that I had some clue about how to succeed with Slack. (Slack? Really Slack?) Arrive with a deep breath and try to find the door.

That first Slack office is worth some description. It was on Clementina, a half street that didn’t really go through many intersections but popped up again here and there in SOMA’s grid as a spur line between blocks.

The address I had been given led up an accessibility ramp to a glass door. Inside the door was a kitchen with two stainless steel tables. One table held snacks and cutting boards and kitchen appliances, a bowl of avocados. The second table held a fully stocked bar of liquor bottles and cocktail tools, a rainbow of liquids. I learned later that day that the pair of tables had come to the company through an auction of goods from a morgue. These were cadaver tables.

Through the kitchen was the main work area, a hangar-like cube of space whose ceiling was mostly skylights. The California sun blasted in by 10 am and so the team had stretched a parachute on cords across the centre of the cube to diffuse the blinding light. Desks were arranged somewhat orderly in a grid. A meeting area in a corner hosted a futon and a few chairs. Some folks had erected individual umbrellas to shield their screens from the light and glare.

I met Cal Henderson, the husband of Rebecca Reeve who I had worked with before and who had introduced me to Stewart in the first place. (See the Preface chapter, Pre-Slack: Meeting Stewart.) Cal was a bright, bearded programmer and the CTO.

I met Eric Costello, another bright, bearded programmer, whose focus was front-end engineering. I met Myles Grant, a third bright and affable programmer, but without a beard.

(Later I would learn each of them was remarkable, both at their respective and intersecting programming specialties, but also in diverse ways. Cal literally wrote the book on PHP programming on the bus ride of his daily commute. Eric had an English degree and had invented ways for websites to dynamically update their interface called DHTML that everyone now used and took for granted. Myles was a ranked swimmer and BBQ chef.)

The office was bigger than the team needed it to be and had a bit of a haunted feel. In the Glitch days the team had been three times as large.

In contrast to the empty office space, the people I met had a really nice feel, like a bunch of weirdos bonded through hardship. They had seen some bad days and stuck together. They each had special skills that complemented each other, and broad skills that touched their teammates’ respective areas of specialization. This overlap gave them a huge surface area of shared understanding to lean on. They knew each other well and could relate and interoperate.

The mood was upbeat. The team retained a very strong hope for what they could create together. They were tight. And for good reason. They were very good at what they did and they really enjoyed their work.

Introducing: Marketing

So what was I there for? I was new and had some new expertise to offer the team. I hoped I had an ability to help them succeed where they had failed in the past.

But this was a new product and it needed to find a new market. Glitch had been a game for consumers to play. Slack was a product for businesses to be productive.

We had to learn how to take a business-to-business (or B2B) software product to market. And soon. The clock was ticking. Like all startups, it was a race against time. Until we found our market, the money and the faith and the energy were all being depleted daily.

So we started with a lot of questions. I had questions and doubts about what I could do. The team had much more practical questions about how we could get started. The biggest question we all shared — how were we going to get customers?

First up, I wanted to make B2B marketing real and tangible for them. So we did an exercise that gave them some group work.

They broke into 3 groups and each independently talked about:

* What was the last thing they had bought online? Describe the purchase process.

* When did they first become aware they had a need or want for the product?

* When did they first become aware of the product?

* How did they find the thing they purchased?

* How did they decide to purchase that thing instead of another thing (or nothing)?

Then we got back together as a full group to review the discussions. I liked to hear their answers about buying software or new computing. But I was far more interested to see how diverse and diffuse their respective purchase processes had been.

In our discussion it became clear that some parts of their decision they each knew. Some parts they had to figure out together. The purchase process proved complex, like they each had a piece of the puzzle and the puzzle only revealed itself as solvable once all the pieces had been shared.

I took some notes and we started to see some larger patterns emerge on how they purchased things. From those patterns, we started to create a shared understanding of how customers acquisition and conversion could work for our imaginary customers. After all, it had worked on them.

Throughout the discussion I added in some rough ideas from past marketing work that I thought might be applicable for Slack. It was fun to see how those tactics showed up in their purchase journeys too.

None of these rough ideas was particularly sexy or groundbreaking. But having them as part of the conversation helped to convey some of the basics of how B2B marketing could work.

We talked about public relations, contributed articles, advertising, word-of-mouth marketing, search engine optimization, landing pages, white papers, emails, testimonials, reviews. It all felt a bit like a job interview and a bit like a learning and teaching session, all rolled together.

As we talked, the challenges that we faced started to get clearer for me too.

What was Slack?

To start with, the key question: what was Slack? How could we go to market with a product that people loved but didn’t really know how to describe? Would some standard B2B marketing tactics actually work? If so, which ones, in what order and with what weighting?

The portmanteau word freemium had been coined already but was not yet widely used in B2B software sales. This was 2013. I can’t remember if it was a label we used in discussion that day, but it was certainly the mechanic we started to imagine that would lead our growth. People had to experience Slack to really get it. How could we help them get started?

Stewart flitted in and out throughout the day. He clearly had an idea about what he wanted me to accomplish. Yet beyond meeting the team, that goal was a mystery to me. In hindsight I’d guess that he wanted to show his team there was a new marketing approach to compliment their new business software, and he wanted to see if I was up to the job.

At the time, I had only a slight idea of how masterful Stewart could already be at some of the marketing tactics I would be responsible for starting. He knew the PR game, cold. He was already a very accomplished communicator and storyteller. He had some ideas about how to pitch the product based on conversations he’d had with friends, connections and warm introductions. He wrote very well.

In short, he was going to be my boss and he was already very good at the things I would need to do.

We broke for lunch and the team rose as individuals all clearly accustomed to eating together. Through the narrow SOMA streets we wound to a line of food trucks huddled in the shadow of an underpass. Señor Sisig was the top choice, a Filipino fusion operation with generous portions. I made conversation with my new teammates and went with the recommended option of adding a fried egg to the top of my Sisig Salad.

We trooped back to the office and ate at some vacant desks. I started to get to know the team.

We finished up lunch and settled in for another session, this one on measuring our results. We started with something called the AARRR framework (AARRR = Acquisition, Activation, Retention, Referral, Revenue – a metrics funnel for startups measuring customer acquisition). Then we moved on to working on some draft positioning statements to start to answer the key question: What is Slack?

As we worked on positioning, Stewart appeared and listened in and then started to participate with one group. We shared back our work to the team and I still have the notes from that session when everything was wide open and unknown and speculative. No one knew Slack. We didn’t even know Slack.

Did we answer the key question — what was Slack? Not really. We got closer but it was still pretty fuzzy. We still had much work to do.

We wrapped up and folks dispersed and settled into some individual work at their desks. I wrote some notes to try to capture the details of our conversations and educate myself. I’ve included those notes as an appendix at the end of this chapter, if you’re interested. They’re the real deal from that afternoon, along with some reflections I added in on the flight home.

At 3 pm everyone rose from their desks at once. Something was happening that was clearly understood by everyone and lost on me. Coffee run. We trouped out together to the California sun and walked a few blocks to a high-end speaker shop that happened to also have a cafe in the back — the team’s preferred coffee source.

The last thing I remember of that first day was leaving the office back to the bright sun. Stewart offered to call me a town car using an app on his phone called Uber. I had never heard of this option or service.

As we waited for the car he explained to me how I wouldn’t have to pay when I arrived at the airport. He would be charged for the ride through the app. He had just pushed the button on his screen and then the town car showed up. It was a bit magical.

I got into the car for the return journey home. I remember thinking to myself: okay, I don’t know where this is headed, but I’m going to roll with it. Uber. Sunshine. Filipino fusion. AARRR. Parachutes. California. Let’s go.

Up next:

Day 1: SF f2f Notes

I wrote the notes below on my first day at Slack and shared them with the Slack team, in Slack, the following morning. I’ve included them here, should you be interested. It’s probably only really interesting to deep insiders and / or startup nerds. YMMV. This is how the sausage got made. You’ve been warned!

Buying and Positioning and Marketing oh my!

Notes from our conversation about what is marketing and how marketing can work for Tiny Speck's new Slack product. (Originally would have been written with markdown notations (H2, #, *text*, etc.) for formatting because that’s how we would write in Slack at the time.)

Exercise 1: Buying on behalf of the company

Think of a time when you had to buy a product or service on behalf of a business. Could be a piece of software, choosing a lawyer, finding an office, hiring an employee. Anything where you made a decision to spend the money of a company.

* How did you know you had a need?

* How did you articulate / describe that need?

* How did you find solutions to that need?

* How many options did you consider?

* How long did it take to make a decision?

* Who else was involved in the decision?

* How much did you spend?

Team 1

Bought a continuous integration service called Travis CI

1. How did you know you had a need?

* Bugs in the mobile app that were pointed out to Brady. CI is a common way to fix that issue.

2. How did you articulate / describe that need?

* We had tried it before for private stuff and it hadn't worked but then it was going to work for our situation.

3. How did you find solutions to that need?

* They had a partnership with GitHub. That made us aware of them and gave them credibility. We had used it before as a non-commercial version.

4. How many options did you consider?

* 3 options: Travis, CI Simple, self hosting (Jenkins)

5. How long did it take to make a decision?

* 5 months (total time — very quick and easy to make the final decision because a test version had been set up 5 months prior)

6. Who else was involved in the decision?

* 4 people: Ali, Cal, Myles, Brady

7. How much did you spend?

* $200 / month

Team 2

Bought help desk software called HelpScout.

1. How did you know you had a need?

* Knew they needed a reliable system for help tickets. Easy to use. Build or buy? Not a chance we were going to build it.

2. How did you articulate / describe that need?

* Used Zendesk previously. Established category of products – hosted help desk systems.

3. How did you find solutions to that need?

* Online research - Googling online ticketing systems. Looked at what another company (Lift) does to solve the problem. Referrals / suggestions from Stewart who did search.

4. How many options did you consider?

* 3: Zendesk, HelpScout, UserVoice.

5. How long did it take to make a decision?

* 2 - 3 days to make a decision then a week of testing to make sure it was right. Total time was about 2 weeks.

6. Who else was involved in the decision?

* 5 people: Ali, Stewart, Cal, Myles, David

7. How much did you spend?

* $100 / month

Team 3

Bought scalable hosting from Amazon called EC2.

1. How did you know you had a need?

* Had to host somewhere. Core requirement of what we were building. EC2

2. How did you articulate / describe that need?

* We need to have it. Ability to install any software. Easy to add capacity. Cheaper than hosting it ourselves.

3. How did you find solutions to that need?

* Past experience. Using it on previous projects. Knowing about it in the market. Market knowledge. They are the market leader.

4. How many options did you consider?

* There are competitors – Rackspace, Google Compute Engine, hosting it yourself – but everyone uses EC2 until they grow to a certain size.

5. How long did it take to make a decision?

* A week. A day is what was remembered. It was understood that this was what they were going to do. There were really no alternatives.

6. Who else was involved in the decision?

* 4 partners: Cal, Stewart, Sergei, Eric, Myles

7. How much did you spend?

* Couple of hundred a month. Over 5 years about a million.

Observations and Notes

* Everyone mentioned the short-term cost of the product (/month) as the default answer to how much did we spend with the full lifetime value of the purchase (/month cost * # of months of use) only coming up with Amazon EC2

* Body language – when asked to explain the purchase process it makes us feel anxious because we made decisions based on emotional reactions then have to make sense of them with reason / logic

* We had some discussion about Aspirin-type products that relieve a pain and seem necessary to buyers vs. vitamin-type products that augment / increase something existing – we want as much as possible to move Slack towards an Aspirin-type product because it makes it an essential purchase vs. a discretionary purchase

Classic 4 Ps of Marketing

Derived from a physical world.

* Pricing

* Promotion

* Placement

* Product

5 Ps of Software Marketing

Iterate through these steps in sequential order. Once you have the first right, move to the second and so on.

* Positioning

* Product

* Placement (distribution)

* Promotion

* Pricing

(Startups don't work this way because they build the product based on what they want to build, then find the positioning to take it to market.)

2 notes on software pricing

* Pricing is last because no one knows what software should cost and everyone changes what their software costs as they learn what it should cost.

* There is a traditional Valley of Death in software pricing ($5000 or less / year sells itself <-> $100000 or more / year and it's sold to you)

Exercise 2: Working on a Slack Positioning Statement

Positioning Statement Template

Answer these questions in order then string together the answers to create a positioning statement. Next, test your positioning against prospective customers. Does it resonate? Does it work? Do they want to try the product? Do they stick with the product?

* For (who is the customer?)

* Who need (what is their pain?)

* Product X is (what is your product?)

* That provides (how does it solve the pain?)

* Unlike competitors (what competes with your product?)

* Our product (what makes your product superior?)

* The company also provides (what added punch is provided to seal the deal?)

Example from Mobify

For e-commerce leaders with more than $20-million in annual revenue who have 5% of customers visiting their website on mobile devices, Mobify is a mobile web platform that delivers an ROI in new revenues in less than 100 days.

Unlike proxy-based competitors like Usablenet and Moovweb that create a separate, m-dot website for mobile customers, Mobify works with responsive design and adapts any website to mobile devices (and any device).

In addition, Mobify is open source and built from open web standards – HTML, CSS and JavaScript – so inhouse development teams have the power and control to easily build with their existing knowledge base.

Team 1

* For: Autonomous teams that do not have an adequate communication solution.

* Who need: Information visibility, archive, and retrieval.

* Product is: Team Communication Software.

* That provides: Real-time, transparent communication and file sharing among all team members with easy information retrieval.

* Unlike competitors: Unlike email, unlike IM, unlike Skype, everyone is together, sees the same information at the same time, and is simultaneously available.

* Our product: More attractive, convenient, and faster to use.

* The company also provides: All content if fully searchable.

Positioning Statement:

For autonomous teams that do not have an adequate communications solution, Slack offers information visibility, archiving and retrieving of all your team’s communication.

Slack is team communication software that provides real-time transparent communication and file sharing among all team members with easy information retrieval.

Unlike email, IM and Skype, everyone is together in one application, sees the same information at the same time, and is simultaneously available.

Slack is more attractive, convenient, and faster to use than other enterprise communication solutions, and all content in Slack is fully searchable.

Team 2

1) For (who is the customer)?

* knowledge workers (people who use computers for most of their work day)

* startups, new companies, technical teams

2) Who needs (what is their pain)?

* distributed teams that need to be in close contact

* friction of team communication

* information overload, overhead of messaging

* too many different moving parts

3) Product X is (what is your product)?

* a hosted web service with mobile and desktop clients

4) That provides (how does it solve the pain?)

* real-time communication with file-sharing: centralized, persistent, and searchable

* easy tools that provide better communication for your team

* coordination of team efforts

* a persistent archive of all of your team's decisions and communication

5) Unlike competitors (what competes with your product?)

* everything that you put into slack is easy to find and always available

* you never lose your place in the flow of team communication

* the more you use Slack the more valuable it becomes (avoid information decay/noise)

* who merely provide more ways to communicate, we provide better ways to communicate

6) Our product (what makes your product superior?)

* combines the strengths of persistent, asynchronous communication (email) with real-time,

* lightweight instant messaging (chat)

7) The company also provides (what added punch seals the deal?)

* easy integrations with your existing company services

* slack becomes the centre for your company's communication needs

* a pleasant and well-designed user experience

Statement

Slack is a hosted real-time communication platform for teams that rely on computers for their everyday communication. It provides real-time messaging and easy file-sharing in a format that is centralized, persistent, and searchable.

Unlike with other communication solutions, everything that you put into Slack is easy to find and always available. We make sure you never lose your place in the flow of team communication. Additionally, the more you use Slack, the more valuable it becomes as it archives your team's decisions and conversations.

Slack combines the strengths of persistent, asynchronous communication (email) with real-time, lightweight instant messaging. It also integrates with your company's existing services and tools so that it can become the centre for your company's communication needs.

Team 3

Statement

For teams of up to 150 people who need to simplify their communication systems, Slack is a messaging and file sharing platform that provides archiving, search, sync and real time notifications.

Unlike chat-centric competitors, Slack's emphasis on search and file management brings more of the team's communication into the same place, saving time and effort.

In addition, Slack makes integrations with your existing systems simple, amplifying the value of every tool in your organization.

Value Proposition

* need to identify attributes of target customers

* need to find their points of promiscuity - what tantalizes them and makes them want to try a new product? what is the reward we can offer?

* assumption: once one small team in an organization uses the product for X days it will spread

In a 500-person sized prospect company:

* have freedom to access any website on the web

* have freedom to install their own applications on their machine

* have freedom to choose their own applications for workflow

* price must be expensable to avoid budgeting process (< $500 / month)

* have a BYOD strategy in place for people to use personal devices

* trust people and not necessarily institutions - are developers or technical and so understand how distributed authority / credibility is (HN culture)

* it's much easier to see in hindsight a company's positioning and value proposition

* it also skews perception because of a survivors' bias - we only talk about the companies we know about that have reached some market traction

Could we use a rotating homepage strap statement from people who are already using the product to show how variable it is by showing their answers to the question:

What is Slack to you?

* IRC on steroids

* The fastest way to collaborate I've ever discovered.

Additional reading on marketing

Customer Development

* Steve Blank's book, Four Steps to the Epiphany

* Steve Blank's blog on customer development (his approach that's a companion to product development)

* Steve Blank videos from his lectures at Stanford

* Longer Steve Blank presentation on customer development called Why Accountants Don't Run Startups

Pricing and Segmentation

* Iterative Path by Rags Srinivasan is a terrific resource that's a little roughly written: http://iterativepath.wordpress.com

Behavioral Economics

* Rory Sutherland on how advertising creates value (YouTube)

* Rory Sutherland in an interview (YouTube)

Positioning

* Positioning – The battle for your mind

* Positioning is also a pretty good Wikipedia entry

One day, around 2018, back when I travelled a lot for my work at Slack, I read an article in the New York Times about the first woman to translate Homer’s epic poem The Odyssey into English from the original Greek.

The translator’s name was Emily Wilson and her story of the process of translation stuck with me. The process itself struck me as epic, and a few years later I did something about it.

In particular, the story of Emily Wilson’s choice on how to translate the fifth word of the poem – polytropos – stuck with me. From the NYTimes article, a few passages:

“One of the things I struggled with,” Wilson continued, sounding more exhilarated than frustrated as she began to unpack ‘polytropos,’ the first description we get of Odysseus, “is of course this whole question of whether he is passive — the ‘much turning’ or ‘much turned’ — right? This was —”

“Treat me,” I interrupted, “as if I don’t know Greek,” as, in fact, I do not.

“The prefix poly,” Wilson said, laughing, “means ‘many’ or ‘multiple.’ Tropos means ‘turn.’ ‘Many’ or ‘multiple’ could suggest that he’s much turned, as if he is the one who has been put in the situation of having been to Troy, and back, and all around, gods and goddesses and monsters turning him off the straight course that, ideally, he’d like to be on. Or, it could be that he’s this untrustworthy kind of guy who is always going to get out of any situation by turning it to his advantage. It could be that he’s the turner.”

…

“So the question,” Wilson continued, “of whether he’s the turned or the turner: I played around with that a lot in terms of how much should I be explicit about going for one versus the other. I remember that being one of the big questions I had to start off with.”

…

“I want to be super responsible about my relationship to the Greek text. I want to be saying, after multiple different revisions: This is the best I can get toward the truth.”

πολύτροπος

I knew The Odyssey lightly before I read this article. A few years earlier still, around 2010, I had listened to the story as an audiobook while driving thousands of kilometers across Canada, from Vancouver where I lived, to Winnipeg where I grew up.

The startup company I had founded and sunk my savings into was flailing and reaching its end of life stage, though I hadn’t totally recognized it yet.

On my return journey to Vancouver I dipped southward from Calgary into Montana. I followed a route called the Road to the Sun. I met with our biggest customer in Missoula. I left that meeting disappointed. They were happy with what we’d done for them and might buy from us again, someday. That was the moment I realized my company was done. If we couldn’t get them to buy again, what hope did we have?

I drove back north into Canada and into the valley of Kootenay Lake, listening to The Odyssey. The road and the story together pulled me onwards. The mountains, sharply sheered up against the blue sky, were still capped with snow. In the air around me I heard of Athena, the bright-eyed goddess.

Now zoom ahead with me to a decade later, to the summer of 2020. After 7 years at Slack, I had just left the formal world of work and all that travelling to stay put and start something new.

One of the first projects I worked on turned out to be born from many of the ideas I’d had rolling around in my head — journeys, translation, beginnings, the durability of ideas and materials, home. I felt like perhaps I had been carrying all these ideas with me as I travelled. Together, they started to take shape in a new kind of project I thought of as my own polytropos.

In short, here’s what I wondered. What if the complicated and many turning or many-turned idea of polytropos could be made into an object — a sculpture inspired by an article about a translation of an ancient story? What if that sculpture were cast of bronze, the dominant material of the age of the Odyssey? And what if the object was itself many turning, like a pendant on a necklace or coin on a string?

In that mix of echoing ideas is where I started to cast about. That is where I tried to find my own new beginning to life after Slack.

Casting

If you want to cast something in bronze today, how do you do that?

After a few searches and speaking with two foundries, I learned that to start you find a designer and production house. I also learned that almost all bronze sculpture now gets done for the dead — as headstones and commemorative plaques. Only occasionally is there a commission for a statue or sculpture.

After a few more calls I met Evie Katevatis from Century Monuments.

“Fun fact,” she said in her first email, once I’d described the idea. “My dad is from the island where Odysseus is from!”

Evie reported the island to be Ithica, which used to be known at Thiaki, and now has been officially renamed Ithake. And though some scholars argue with this certainty, to Evie, the line of the story is clear — this is where Odysseus is from. So I’m going to repeat that here too.

By email, I told Evie my idea.

I imagine a bronze sculpture that resembles a large coin with a hole in the centre. The diameter of the coin would be ~25 cms and the diameter of the hole in the centre would be ~7.5 cms. It would hang from a strap and be able to turn in the wind.

On one side would be all the synonyms for the greek word polytropes (many turning) that have been used in the opening sentence of translations of The Odyssey over the years. There are about 40 of them.

On opposite side would be the opening lines of the most recently translation of The Odyssey by Emily Watson (the first woman to translate the poem into English).

Those opening lines are:

Tell me about a complicated man.

Muse, tell me how he wandered and was lost

when he had wrecked the holy town of Troy,

and where he went, and who he met, the pain

he suffered in the storms at sea, and how

he worked to save his life and bring his men

back home. He failed to keep them safe; poor fools,

they ate the Sun God’s cattle, and the god

kept them from home. Now goddess, child of Zeus,

tell the old story for our modern times.

Find the beginning.

I’m not a designer and I have no experience as a sculptor or working with bronze, so I’m seeking help and expertise. I always thought of using bronze because the age of Odyssey was the Bronze Age, so that symmetry was nice.

So that’s the outline of the project. Does that sound like something you’d be interested in learning more about?

Evie proved to be interested and excellent. She listened and coached me. Her expertise guided the sculpting process: sizing, fonts, lettering, design.

Soon enough we had a PDF mock up that we emailed back and forth. We agreed on details. The PDF got output to a polymer casting that the foundry would use to form the bronze sculpture. I signed off on my parts and hoped.

The foundry

A few weeks later, we had a production date at OBRONZE in Richmond, BC. Another week later and I got a call. The finished piece was ready to be picked up.

I dropped my son to school and drove out to get it. The address for OBRONZE led me to a series of warehouse fronts on a dead-end cul-de-sac behind a collection of auto body shops. Some of the warehouse doors gaped open. Others stood rolled shut. Signage was minimal so I parked and started to walk. Eventually I found a bronze plaque next to one of the gaping doors that read OBRONZE.

The acrid darkness inside smelled of fire and the bloody tang of metal. I knocked on the frame of the door, “Hello?”

From the darkness a voice answered. Then a man appeared in a heavy apron seasoned with soot. He held metal mandibles. I introduced myself and why I was there. He told me he knew my piece. He pointed with the mandibles to a glass door behind me. “Pay at the office and bring me the receipt.”

I crossed to the glass door and pushed it open. The venetian blind on the back side of the door clattered. Before me was pretty much every industrial office I’d ever visited: foam-panelled suspended ceilings, veneer walnut desks, a grid of security bars, dust.

“Hello?” I called out. The venetian blind tinkled back against the glass. A voice answered and I pushed through another door. A small woman with silvering black hair said she knew my piece. “I came from over there,” I told her, pointing back to the darkness.

“The foundry,” she said, and this was remarkable to only me.

She had a bill for the agreed-upon price. I handed her a credit card that she fitted into a manual impression device — chuck-chunk it went as she rolled the plastic bar, and this was also only remarkable to me. She waved the duplicate impression at me with little time for chit chat. “Take this to Irv.”

With my receipt in hand I returned to the darkness of the foundry. Irv in the apron was waiting just inside the door. He had my piece boxed up in his hand. He wanted to know what I was going to do with it.

I told him I planned to hang it from a rope as people used to hang coins that they carried. He turned the piece over in his hands, as if imagining it hanging from a rope. He handed me the small rectangular box.

“You know it will turn when you hang it, right?”

“Yes, I hope so.”

A silence stretched out between us. He grinned but didn’t ask any more. I wanted to tell him more, but resisted. I took the piece and weighed it in my hands. Twelve pounds of dense mass. I didn’t know how to tell Irv about the intention of the piece, or the origin of polytropos, or the story and the ideas and the translation of the meaning. All that felt like it would gush out at once. I hadn’t even had the chance to see it yet!

“Good luck with that,” he said finally and turned back to the darkness.

“Thank you,” I called.

I found my car and opened the tailgate and put the box down. I unfolded the flaps that held it closed. Inside was a film of bubble wrap surrounding a round shape. I peeled back the plastic and saw the piece for the first time. I turned it over in my hands. The edges felt sharp under my fingers and its golden lustre reflected the light in angles. It still smelled of the acrid darkness, of fire and the bloody tang of metal.

I wondered how long the edges would stay sharp. How long before the bright shine dulled? How would time pass and change this piece? I wanted to find out.

Coda: So, I’m asking you about home

One more thing to add as a kind of coda to this project. From the excellent podcast, that I recommend listening to in its entirety, Conversations with Tyler: Emily Watson on Translations and Language, episode 63.

COWEN: Here’s another reader question about translation: “Could you please ask her about home? Her translation pulls this word to the foreground more than I remember other translations doing, and that decision made me read the text differently. It also made me realize that home is not a concept that I interrogate nearly as much as I should.”

So, I’m asking you about home.

WILSON: I love that question. The Greek text has a lot of uses of the noun nostos, from which we get nostalgia, the journey of homecoming, the event of homecoming, and then of cognate words. I wanted to use the word home as a way of signaling the centrality of the concept of home, and of defining the concept of home in the poem.

It’s already a very loaded word in English, I think. It’s a word which means so much more than just house or place where you live. The Odyssey is fascinating in the ways that it defines home as something which involves both a living space, a particular kind of community, and a space where at least one member of the household has the choice about who to keep in, who to keep out.

Up next:

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On a bright spring morning in 2009 I stood outside the Forestry Sciences Centre at Vancouver’s University of British Columbia waiting for Stewart Butterfield to arrive.

Inside the building, the MC of a conference I had helped organize was on stage kicking off the program. Stewart had, through a loose mutual acquaintance, committed to doing the morning’s keynote talk. The keynote talk was set to start in less than 10 minutes. Stewart was yet to arrive.

Did I feel nervous? Yes. Water is wet. I tried to stay calm and replay the steps that had brought me to that point. Perhaps I could find a hole in the process to patch in 10 minutes? Day dreaming didn’t hurt or help.

The conference was called Northern Voice and felt very much of the time, started by a collection of geeks, technologists and idealists who wanted to build an event that met them at the intersection of their interests. It was run by volunteers through a non-profit called the Northern Voice Conference Society.

No one talked about ‘Web 2.0’ but that label probably fit it best. It was earnest and inclusive and community driven. There was a general trust in connecting technologies, transparency and the enablement of more voices to be heard. Our collective default setting was optimism. We had hopes.

When we had brainstormed ideas for keynote speakers, Stewart’s name had come up. He was from Vancouver, mostly. He seemed thoughtful and successful and like he would have something interesting and different to say.

But he’d been a reach. Could we get him? Would he be available? Would he say yes and show up and do a great job? Our honourarium was exactly zero dollars. For out of town speakers, we covered their travel. The commitment from Stewart that we’d received second hand felt tenuous. Maybe we should have planned for an alternate keynote speaker that morning? We had not.

Already a star

At the time, Stewart was already a star in the business-tech-geek niche that mattered to us. He had co-founded Flickr and sold it to Yahoo! for many millions. He’d been on the cover of Newsweek and The Guardian and Business Week. He’d written a widely circulated resignation letter when he left Yahoo! that starts out, “As you know, tin is in my blood.” He’d done it all with an authenticity and style that cut through cynicism and felt real. He’d sold his company but not his soul.

So yes, he could be afforded a broader patience, I told myself as I waited. The loose mutual acquaintance who had secured Stewart as a speaker had proven to be eventually reliable in the past. We had promoted Stewart’s talk through channels that he would have likely seen. But the nagging and obvious question remained: would he show up and would it be vaguely on time?

A silver Audi whipped into the parking lot. I could see it was Stewart and waved to him. He grabbed his shoulder bag and hustled inside. I paid his parking and followed. We stood together backstage while the MC finished the set up of the day’s program.

“I’m not really ready for this,” Stewart said.

“What’s your talk about, Flickr?”

“No, the Internet.”

“Well that’s big enough.” I took a pause. “People will like that. They’re a good audience.”

“F**k it, here we go.” And he walked on stage.

I don’t remember the talk much because I basically watched the audience, who had no clue of my personal scheduling drama, and were keen to see the star. They responded well and it was an imagined crisis averted in total. Okay, onwards. I got ready for the rest of the program.

That moment of anxiety I’d held in the parking lot before Stewart arrived blurred into that social rush of details and problem solving and “hey, great to see you again” of a conference day.

But one of the advantages of running a conference for tech geeks at that time is that everyone memorialized important events. So it’s easy to find posts describing Stewart’s talk on blogs. And I’m happy to report, people loved it.

The Internet, a love story

The talk was called, The Internet, a love story. It stands up very well to time, and I think provides some foundational insight into how Stewart saw the web and software, and the nature of technological progress for humans.

An excerpt from the live stream of popular tech blog, Miss604:

Stewart’s keynote begins as a photo story, from an image of a shack in the woods to illustrate his home town of Lund, to black and white hippie photos of him and his parents, and a young Stewart in a “Radio Shack Computer Camp” trucker-style hat.

“Back then, in 1992, the internet was a way to keep in touch with people going to university in other places,” mentions Stewart while sharing some of his old usernames and email addresses (that, at the time, were at least 20 characters long). He’s also showing some postings he’s made to groups online (circa 1993) including his first online community rec.music.phish.

…

Stewart moves on to “this is who I am” and shows images of various ways people express themselves and who they are, from bumper stickers to hairstyles and clothing. “People tend to pick up more adhoc bits of culture,” A photo of a crowded auditorium pops up with Apple notebook symbols glowing (and a little red arrow points out the single PC user).

“In the early days, photography was about memory preservation,” notes Stewart as the Flickr logo spins up on to the screen. Trends Stewart highlights include: Ubiquity of capture devices, Spread of the network, Change in perception and attitudes — participating is no longer weird.

…

Stewart address the changing role of computing over the years including, ‘Relationship-based computing’ which replaces document-based computing which replaced application-based computing (from Stewart’s slide).

Update: The presentation ends with “Anyway, this is why I love the internet.”

In short, Stewart was a local boy from Lund (literally, the end of the road just 128 kms north of us in Vancouver, population 287). He’d gone out and made good in the wide world, and done it with style and without losing his credibility. I don’t think it’s too far reaching to say that he was a small hero to us in that Northern Voice crowd.

Did it matter that his talk was a redo of other materials he’d already delivered? Did it matter he improvised? Nope. People rooted for him. He was a legitimate headliner to kick off the conference. So what if he wasn’t as polished as others? He was a star.

A newer new thing

I’d like to say at this point that Stewart and I lost track of each other for a few years, but that wouldn’t be true, because we never really had much track of each other to begin with.

Sure, we recognized each other. We shared a few other brief conversations in passing at events like the launch of his next initiative, Glitch. But we were not close or even casual friends. I didn’t have his email address. Time passed.

Then a few years later a mutual friend introduced me formally to Stewart. I was looking for a new job. Stewart was looking for help for his newer new thing, which he did not name.

It was May, 2013 and my son had been born in February. The software company where I had worked wanted to offer me parental leave. Actually, they had to by law. But in reality I was the oldest person at the company (at 37 years old) and no one else had children. It was one of the many startups around where the employees were not much more than salaried children themselves.

Going back to work after 5 weeks at home, I soon found that my now much-less-flexible home life clearly clashed with my work life. Expectations became irreconcilable with reality. There was only so much time each day and I had to prioritize.

So I had left the company in April and started reaching out to trusted folks I knew, looking for a better option.

One of those folks I trusted was Rebecca Reeve. I’d worked with Rebecca on a number of projects and we’d found good success. She introduced me to Stewart, by email, copying Stewart, just like this:

James, just told Stew you've recently become available and he wanted me to send a quick intro. Tiny Speck is working on a new workplace comms tool. I'll let you two take it from here.

And Stewart wrote back one minute later:

Thanks Rebecca :)

James — I know you.

This was the start, and it started to give me a glimpse into the story of the guy I was going to work closely with for the next few months and years.

Stewart was Stew to friends (at the time). He worked with people he liked and trusted. He used text as a playground for expression (check that em dash!). He used both emoticons and formality in business communication. He valued and knew the value of his own voice and seeing people. What else? There was so much that I would have to find out. We were off to the races.

Stewart and I met for coffee at the JJ Bean on the corner of Davie and Homer in downtown Vancouver. We talked briefly for context (here’s what I’ve been up to, what have you been up to?) and he demoed a new product for me.

As he demoed, I had what seemed to be such an embarrassing lot of questions about the basics – why did the text scroll from bottom to top? Did people really use emoji in their work communication? Could anyone really join each of the #channels and see the full archive of what everyone was saying? Were people really going to pay for this when they didn’t pay for other chat tools?

Somehow those total noob questions didn’t sour things. Stewart asked me for a proposal to do some marketing work for Tiny Speck’s new product on a 3-month contract. I typed up a proposal and sent it to him. A few reference calls later and I had a start date to kick off my work in their office: June 5, 2013.

Okay, great. Now, what was I actually going to be doing?

Call it marketing

From my conversation with Stewart and some press coverage I found, I had a rough idea of what was going on, but I really knew so little.

After leaving Yahoo! to get back to his first love of tin smithing, Stewart had gotten many key members of his Flickr team together again. They’d raised $16-million of funding from A-list venture capitalists to build an online game. They’d launched Glitch.

Glitch had been cool and lightly fun, “a virtual world that looked and behaved like a Dr. Seuss book as re-imagined by Cheech and Chong, in which players helped the eleven sleeping giants in whose dream this world existed by carrying out acts of creativity and cooperation.” But it had been a commercial failure and closed down 6 months earlier, in December, 2012.

When the Tiny Speck team (the company behind Glitch) closed down the game and broke the news to their investors, they had offered them two options: they could give back the money they had left ($2 to $3-million) or they could pivot to work on something they had cooked up internally – a team communication system called Slack. The investors didn’t want their money back and urged the team to push on with Slack.

Why not cut their losses? The larger picture, which I would guess was in the mind of all the investors and employees and drove the decision, was the hope that Glitch could repeat a pattern of pivoting from failure to victory.

Glitch’s predecessor, Flickr, had been born from another failed game called Game Neverending. The photo sharing feature of Game Neverending took off because it launched just as smartphones with embedded cameras hit the market and as digital cameras rose to prominence. Stewart and the team saw that uptake and refocused the company to build solely for photo sharing. They had pivot precedence.

So Flickr had been a huge hit born from a failed game. Could Slack follow the same course and become a hit from a failed game? That was the question.

And that was the situation I started with at Slack: big expectations, a small team, a prior hit, some money still in the bank and a looming, palpable, practically haunting fear of another failure.

Thanks for reading A Slack Story! Subscribe for free to receive new posts and support my work.

Up next:

After Slack, a new project. A sculpture inspired by an article about a translation of an ancient story. Finding home.

It's the day Slack shares start to trade as WORK on public markets, and I’m on a family vacation with spotty wifi.

So I'm up before the alarm. I check in. The orders I carefully set the night before to turn my speculative Slack shares into real US dollars are missing.

No panic. I have a backup. I set them up again, step by step. The numbers I type into the empty boxes on the screen both unreal and too real. Those sell orders poised to slightly change my life and the life of my family. I have no clue what to expect. It’s tense.

Zoom out

Now zoom out here for a sec with me. Pull back to the big picture.

The years of 2010 to 2022 marked the largest bull market of fundraising in human history. There was simply no better time to raise money for a new speculative venture, perhaps ever. If you had the right story, the right team or the right metrics, money was incredibly cheap and easy to get.

“This is the best time to raise money ever. It might be the best time for any kind of business in any industry to raise money for all of history, like since the time of the ancient Egyptians. It’s certainly the best time for late-stage start-ups to raise money from venture capitalists since this dynamic has been around.”

– Stewart Butterfield, Is Slack Really Worth $2.8-Billion, Apr 16, 2015

And nowhere was money cheaper or easier to get than in software.

"Software is eating the world" wrote the prominent venture capital firm Andreessen Horowitz (a16z) in the Wall Street Journal’s 2011 article that laid out their theory and became received wisdom.

Every company was becoming a software company because every part of every company ran on software or was touched by software. Banks were software companies. Manufacturers were software companies. Advertising agencies and nurses and farmers and drivers all of a sudden were parts of software companies.

And it was also somewhat true: software was eating the world, and is still. “The future is already here, it's just not very evenly distributed,” wrote William Gibson and that phrase has stuck with me as it perfectly describes how changes moves through society.

As computers ran an increasing number of the processes of organizations, the software called business-to-business software became the most attractive of all the speculative venture investments. Software ran payroll. Software ran project management. Software ran the doors of the office and the inventory of the snacks and the ordering of furniture and the coffee machine and the HVAC systems to keep the coddled employees comfortable.

Smaller or richer or younger or more innovative companies generally led the way toward Gibson’s uneven distribution of the future, but all companies were on a similar path to more software. And the path’s progression showed no sign of changing or slowing. Organizations kept adding more software for narrower niches or slower-to-adopt areas of the business. New companies got invented. Very little was untouched or untouched for long.

I know because from June 5, 2013 to June 5, 2020, I worked at a company called Slack Technologies that was at the forefront of software eating the world. My five official roles at Slack gave me a bird’s eye view into the changes happening – the huge sums of money exchanged, how the work of entire national economies transformed, how people, their relationships and workplaces and identities were being revolutionized by software. That’s the big picture here.

Zoom back in

Okay, zoom back in to that morning in Yellowstone and the personal picture.

I’m at the kitchen table of the cabin. The minutes count down to the opening bell of the NYSE. I check the orders, again, again. Everything is ready. I have spent years working at startups, including one I founded and failed at for 6 years. I have spent my personal savings and borrowed and paid off loans and lived with risk for a long time, all in pursuit of a dream of success. I take a breath, and let it go. The hour ticks over and it starts.

My screen refreshes and the numbers have all shifted. The orders are filled, the shares transformed from hope to dollars, the dollars more than I have ever considered holding.

In those moments, what happens? The world has changed for you, for your family, your future, your relationships.

What do you do when the startup myth comes true?

That question – and all the questions that preceded it to get to that point and followed after – I will try to answer in A Slack Story.

It’s actually 3 stories

In the following chapters I’ll try to knit together 3 stories that I believe provide some inside perspective into the times and places where Slack lived and where software was eating the world.

The first story is a big economic story. I mentioned that above in the zoom out: the businesses, funding, fundraising, venture capitalists and capitalism that helped create hyper-growth companies like Slack that ended up worth $28-billion dollars in less than 9 years.

The second story is a comeback story. Slack didn’t start as a success. It started as a failure riddled with burned cash, layoffs, disappointment and tears. Then, nearly the same band of outsiders regrouped from that failure, learned a totally new industry, and transformed a failed video game into a blockbuster workplace tool.

The third story is a personal story. It’s my story as the ninth person to join Slack. It covers a journey of 7 years through 5 jobs and multiple continents and many airports. It’s a story of relationships and doubts, rollercoaster emotions and learning to do what needed to be done by often just doing it.

My intention in all 3 stories is to peel away the media coverage and hype to hopefully reveal some of the magic that made Slack a global phenomenon and huge success.

Some chapters will describe how we did things in details, and share some lessons we learned. Some chapters will sketch the big changes happening in the world around us. Some chapters will reflect the smaller changes happening on my journey, for me and the many people I cared about.

Throughout I’ll try to include source materials and multiple voices in addition to my own. Many of those voices will be from folks who I worked with at Slack. They’re the primary sources. They were in the room when decisions were made. They are an incredible group of bright, humane, funny and talented people.

Together I believe these voices will tell a untold story.

So, why now?

For a few years after I left Slack I considered writing about the company and my experience there. I didn’t act on that consideration until after Stewart Butterfield, the guy who hired me and the former CEO and co-founder of Slack, had left at the end of 2022.

By then most of the other folks I had worked with and considered essential to my experience had also left. In short, while those folks were still with Slack I felt loyal to them, and telling the stories of our journey would have felt a bit like telling tales out of school.

But now that’s over. The company is a different organization, acquired by Salesforce in July 21, 2021, and now part of a company with 50,000+ employees. It’s changed, man, like everything changes.

And with that as context, let’s get started. Find the beginning.

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Up next:

A first memorable talk with Stewart Butterfield at Northern Voice, 2009. A connection from a mutual friend. A failed game called Glitch. A newer new thing called Slack.