In the latest episode of Quality Matters, we sat down with Clint Smith, co-founder of the pioneering email marketing platform Emma, to explore this question through the lenses of entrepreneurship, leadership, and education. Emma helped redefine how private and non-profit organizations communicate with their audiences, but Clint’s reflections extend far beyond email or technology. Having spent time around numerous tech founders and Silicon Valley wannabees, I found Clint’s demeanor particularly refreshing. His style is practically nonexistent in the Valley, where capital is raised on hype, not humility.

Clint’s journey into entrepreneurship didn’t begin with a grand vision or a buzzword-filled pitch deck. It began, as many real ventures do, with uncertainty. After an earlier startup was derailed by the dot-com crash, Clint and his co-founder found themselves motivated by a mix of necessity and curiosity. They didn’t set out to build the biggest company possible. Instead, they wanted to build a company they could be proud of—one that treated people well and created something genuinely useful.[1]

That orientation shaped everything that followed.

Metrics That Matter

In Emma’s early days, success wasn’t measured by hype or press mentions. It came down to a few fundamental questions: Are customers signing up? Are they using the product? And—most importantly—are they coming back?

Those questions may sound obvious, but they reveal something critical. Choices drive higher quality. When customers have alternatives, their decision to stay is meaningful. Clint noted that this same idea translates to education. When families actively choose a school (and continue choosing it year after year), that decision tells us far more than compulsory, zone-driven enrollment ever could.

Just as important was how Emma handled data. While email marketing generates endless metrics—opens, clicks, impressions—Clint emphasized the danger of confusing information with insight. Emma worked to simplify complexity, rolling data into clearer, goal-oriented signals that aligned with what customers actually cared about. In education, where data can easily become noise, the lesson is clear: metrics should illuminate purpose, not obscure it.

My co-host Caitlin and I think about this a lot in terms of education. Just as in tech, there seems to be an inexhaustible amount of data that could be reported on in K-12 education. But does that data actually tell decision-makers what they need to know? While it’s fashionable to malign the No Child Left Behind Act (NCLB) as top-down, federally mandated ed reform, critics often forget that prior to NCLB, the data made available to parents was generally useless. Academic measurements were not disaggregated. In other words, a parent might know that a local elementary school was rated an “A” according to the state’s rubric.

But what about the 5th grade?

And what about boys?

And what about boys in the 5th grade with special needs?

That’s an example of a lack of data, but the opposite, as in the case of metrics that Clint described, can be just as pointless. Take the example of the district in which I live. The “About Us” page informs visitors of key district data points. Among them: the district has “160 schools,” “140+ Countries,” “80,600+ Meals Served,” and “37,400+ Miles Driven.”

No context is given.

Are 80,600+ miles driven per day? Per week? By whom?

Likewise, did students visit 140+ countries? Were students in Nashville born in all but 55 countries in the world?

Moreover, how do these bits of information help a parent determine whether the school is best for a specific child? As Clint noted during our conversation, metrics are most meaningful when they provide the end user with actionable information.

Culture Is Not a Poster on the Wall

One of the most compelling parts of Clint’s story is how intentionally Emma approached culture. Rather than importing Silicon Valley clichés or chasing “move fast and break things” energy, Emma focused on transparency, trust, and shared ownership.

Weekly all-hands meetings ensured everyone understood the company’s goals and how their work connected to them. A written culture guide explained not policies, but why the company existed. Peer-driven recognition—like “Kick-Ass Cards” that employees could give one another—reinforced accountability and appreciation without hierarchy.

The result? A brand experience that was consistent throughout the organization. Customers encountered the same competence and clarity whether they spoke to sales, support, or leadership. That consistency was a direct reflection of how people inside the company felt about their work.

For schools, this lesson is powerful. Culture is not what’s printed on a banner or t-shirt. It’s what families experience at every touchpoint. And it always flows from leadership.

A North Star—and the Freedom to Personalize

Clint also emphasized the importance of a clear, shared North Star. For Emma, that meant profitability at one stage and a successful exit at another. Transparently declaring the goal focused decision-making and aligned the team.

But clarity of purpose didn’t mean rigidity. Underneath that North Star was a commitment to personalization—treating customers, employees, and eventually students as individuals with distinct goals and strengths.

In education, Clint argued, personalization shouldn’t be a luxury. It’s foundational. As a father, he advocates for helping students imagine futures that reflect their interests and abilities, rather than forcing them into generic pathways. That customization didn’t exist for many of today’s parents when we were young, but the fusion of adaptive learning tools and choice programs is disrupting[2] the education status quo. Our kids needn’t be conscripted to the local, zoned school. States like Florida, Indiana, and Ohio show that thoughtful policies enable families to customize education in ways that were unimaginable even 10 years ago.

In the end, Clint’s story is a reminder that quality is not abstract. It’s built deliberately, sustained through feedback, and expressed through culture. Whether in startups or schools, the work is the same: define what matters, align around it, and treat people like they truly have a choice—because they do.

[1] How I wish Clint had co-founded Twitter.

[2] I couldn’t write an entire piece about tech without using the “d” word.

When Florida State Senator Alexis Calatayud describes her constituents in Miami-Dade County’s 38th district, she paints a picture that challenges current headlines, which center around violence, border security, and lost opportunity. “We have political asylum seekers [for whom] education is the number one thing they want to provide for their child,” she told us recently. “They have no money and they’ll work three jobs, but they want their child to have the highest quality education in the world.”

This isn’t hyperbole. It’s the lived reality of families arriving in Miami from Cuba, Venezuela, Haiti, and beyond. And it should fundamentally reshape how we think about educational opportunity and the people who pursue it most passionately.

The economic diversity of Senator Calatayud’s district is striking. She represents some of the poorest communities in Miami-Dade County as well as some of the wealthiest. Yet there’s a unifying thread: “Regardless of their socioeconomic background,” she explains, their expectation is “this community has to give me and my kid a shot.”

This is one of the core components of the immigrant ethos: the belief that education is the bedrock of upward mobility. And it’s not just immigrant families who hold this value. Families moving to Miami from New York, Chicago, and other cities across the country share this same understanding. They all want to ensure their kids have the best quality education, because that’s what will unlock the same opportunities they’ve had, or in many cases, opportunities they never got themselves.

Senator Calatayud takes pride in Miami still being a place where “you can arrive with the biggest name in the world, or no name at all, and build something.” The bedrock of that possibility? Hard work and education.

E Pluribus Unum is a Great Motto, It’s Not an Education Strategy

Here’s where Miami’s diversity becomes instructive. Senator Calatayud’s constituents include English language learners, gifted children, students with disabilities, and more. Their respective needs are radically different, and a one-size-fits-all approach simply cannot serve them all well.

That’s why Miami has become the ultimate hotbed of choice. Thanks to visionary leadership from former Superintendent Alberto Carvalho, Miami-Dade created the most competitive choice environment in an American urban district. Add to that the explosion of microschools, private school options through universal education savings accounts (ESAs), and hybrid and homeschooling opportunities, and you have a giant range of options for parents.

The key word there is “parents.” Because choice isn’t about ideology—it’s about allowing families to find what works for their specific child. As Senator Calatayud puts it: “If the thing that’s right in front of you doesn’t work for your kid, choice is the one that allows you to find it, and to create that equity of opportunity for that kid’s potential to blossom.”

The Work That Remains

But Miami’s success story isn’t complete, and Senator Calatayud is refreshingly honest about this. “The progress isn’t done until every subgroup is at equal high performance in student outcomes,” she insists. When only 60% of students are reading on grade level, when there are still deviations based on socioeconomic background, “we’re not done yet.”

This is where her vision gets particularly interesting. She advocates for extending school choice all the way down to birth, integrating early learning into the continuum of educational options. Why should school choice begin at kindergarten when we know brain development in those early years is crucial? “If we could get 90% of kids on grade level reading by third grade,” she argues, “we could transform what the rest of their lives look like.”

“Our focus should be every child that comes from a low-income background is outperforming the general population because the mission of public education, in my opinion...is to help disrupt generational poverty.” Her clarity of focus is striking, even if early education’s ROI remains somewhat murky.

What We Can Learn

Miami’s story offers lessons for the rest of the country. First, the desire for quality education transcends boundaries. Second, a plurality of needs requires a plurality of educational options. Third, choice isn’t the endpoint. It’s the mechanism that allows us to keep pushing for better outcomes for all children, especially those who have been historically underserved.

When families arrive in America with little more than hope and a fierce commitment to their children’s futures, they’re not asking for perfection. They’re asking for options that will give them a chance to secure a better life for their progeny.

Miami is showing us what happens when we say yes to that ask. The rest of the country should pay attention.

Microschools, hybrid models, and home-based learning communities reflect level of dynamism in education that we’ve never seen before. This movement is due, in no small part, to the wave of school choice programs that allow parents to allocate state education dollars as they see fit. Parents from New Hampshire to Florida to Texas and dozens of places in between are customizing education to meet the needs of their unique children. But it goes beyond public policy. Across the country, parents are reclaiming both the right and the responsibility to shape their children’s education.

Educators, too, are stepping out in faith to launch schools. One inspiring teacher-turned-school-leader is emblematic of this new movement. Kristin Fink, the founder of SKOLA, is not only operating a small, independent school, she is training other teachers to plan and start their own educational experiments.

VELA saw this movement coming early. What began as a hunch—that good people wanted something different—has become one of the largest philanthropic investments in low-cost private and home education in the nation. Since 2019, VELA has welcomed more than 4,600 founders into its network, the vast majority serving low- and middle-income families without relying on large government or philanthropic subsidies.

What makes these microschools work isn’t compliance – it’s trust. Meredith explained that enrollment itself is the most powerful accountability mechanism. Families vote with their feet, and founders succeed by earning repeat enrollment, not by checking bureaucratic boxes.

Perhaps most compelling is what unites these diverse models. Whether classical or progressive, faith-based or secular, the founders share a holistic view of education. Learning isn’t separate from health, family life, or community, it’s woven into them. Education becomes not just preparation for life, but part of living well.

The microschool movement isn’t a trend. It’s a generational shift rooted in agency, courage, and a belief that education works best when it’s built close to the people it serves. Check out the full interview to learn more and don’t be surprised to see more of these innovative schools popping up in where you live.

On this episode we choose songs that remind us of best friends, parenting, and protests. It’s a great conversation full of surprises.

After you listen or watch here and get a taste for how music helps people (even perfect strangers) find common ground, I encourage you to check out the rest of our conversation on their site because we then discuss why music has been such a powerful bonding agent throughout history. I really enjoyed this conversation and appreciate the work they’re doing to inject reasonableness in political discourse.

This podcast is part of the Come Together Music Project, a new 501(c)3 non-profit organization that uses music to deepen existing relationships, create new ones, and bridge ideological, generational, and socio-economic divides. You can find more episodes on Spotify, iTunes, and YouTube.

Stay tuned for more on this project!

Karla reminded us that the Individuals with Disabilities Education Act (IDEA), passed in 1975, was first and foremost a civil rights victory. It granted students with disabilities the right to attend public school. But access alone isn’t the finish line. Nor is compliance. Karla challenges us to move beyond compliance—endless paperwork and IEP meetings—and instead ask the most fundamental question: Are these students gaining ground academically?

In Arizona, just 14% of students with disabilities are reading at grade level by third grade. That statistic underscores a systemic failure, not of students, but of the expectations and supports they’re given. Karla believes under-challenging students is more common than we’d like to admit. Too often, she says, the default is low expectations or assumptions based on visible disabilities—while the majority of students with special needs have “invisible” ones like dyslexia or ADD.

Quality means not just meeting the legal minimum, but building systems where all kids—especially those most overlooked—can be challenged, supported, and seen.

I'd love to hear from readers: If you have experience with the federal IEP process, what’s the first thing you’d change to make the system more effective?

Diogo serves as the President and CEO of the Foundation for Economic Education (FEE), one of the country’s oldest classical liberal think tanks. What sets him apart, though, isn’t just his title—it’s his journey. From studying law in Brazil to political science in New York, conducting research at Cato and Atlas, completing graduate work in London, and leading Brazil’s National School of Public Administration, Diogo brings rare insight into how systems work—and how they often don’t.

That global perspective informs his belief in cooperation and market innovation. Far from the tired caricature of free markets as ruthless zero-sum games, Diogo emphasizes their cooperative nature, their role in discovery, and their power to increase value—not just shift it. His work at FEE reflects this: He and his team support student thought leaders, elevate education entrepreneurs, and provide fellowship experiences that challenge the status quo.

As education systems around the world—and especially in the U.S.—grapple with complexity, Diogo’s commitment to liberty, pluralism, and meaningful feedback loops offers a hopeful model. He reminds us that great education doesn’t come from rigid standardization but from dynamic and diverse ecosystems. And that freedom, paired with responsibility and vision, is still a powerful formula for human flourishing.

That instruction came from a professional development session for teachers at a charter school network, not from a book about the latest parenting techniques. Not being a classroom teacher, I attended the session out of curiosity. But being a new parent myself, where my most pressing problems dealt with sleep schedules, I tucked away that advice, taught to me by an expert educator, for use at a later time.

Taking lessons from one domain and utilizing them in another is at the heart of “Parallel Entrepreneurship.” This concept, perhaps coined by acclaimed CEO Mark Cleveland, is the topic of the most recent episode of Quality Matters. Mark has led multiple private-sector companies over the years, but he doesn’t affix the label “serial entrepreneur” to his work. “Serial” indicates sequential experiences, and Mark is too active and curious to wait for one idea to complete its life cycle before investigating the next big idea. His pursuits happen simultaneously, which allows him to transpose lessons from, say, the textile industry to a software company.

According to Mark, this method is beneficial in at least two ways:

(1) Faster feedback than more traditional serial entrepreneurship because you don’t need to wait as long to test your ideas. For instance, replicating success in Business A may take a year whereas you could test it in Business B more quickly.

(2) Even negative experiences can be used to your benefit because it might be that your tactic was well-executed but in the wrong context.

Paralleling* in Education Ecosystem

Mark is the son of an educator, and I’d like to think his ideas are just waiting to be scooped up by the broader school community. One immediate parallel that I noticed comes from the proliferation of educational models that go beyond conventional zoned public schools. I am a school choice advocate, and one of the reasons I embrace choice is because I don’t think a single model deserves a monopoly when it comes to educating 60 million children. Over half the children in the country now have access to K-12 choice programs in their states, and if we fold in the idea of parallel entrepreneurship, we might embrace sharing best practices. For instance, a tech-heavy model like Khan Academy need not be at odds with the Montessori method. Both report high degrees of satisfaction and success. So how might they learn from one another? Parallel Entrepreneurship could be a model.

As you might expect from someone interested in pursuing multiple ventures simultaneously, the conversation with Mark was wide-ranging: from socks to solving Nashville’s traffic problem, and many stops in between. I think you’ll appreciate his perspective on taking risks, learning from failure, and being open to the opportunities that will inevitably present themselves.

* Paralleling is a real word, it’s also a real tongue twister.

If you’re the daydreaming type you may wonder what you would do with that kind of wealth. I had the opportunity to sit down with someone for whom this is not just a hypothetical scenario. Katie Everett, the Executive Director of the Lynch Foundation (a philanthropic organization that predates Gates by more than a decade), is charged with considering how to give away millions of dollars each year in a way that encourages people achieve their fullest potential.

Most of us will never sit atop a foundation with hundreds of millions of dollars, deciding which bold new idea gets the green light. But after speaking with Katie, I’m convinced that her lessons are relevant for the masses. For instance, during our conversation she highlights:

* Local context over scale - there is a lot of talk among American foundations and businesses about how quickly results can be scaled at state and national levels, but if we leapfrog the deep understanding that comes with local proximity you can be sure that mistakes will be made.

* Honest power dynamics - Katie is clear-eyed about the inherent power imbalance between funders and grantees and stresses the importance of transparency, mutual respect, and truth-telling.

All to say, Katie’s been doing this work for nearly three decades and she’s seen trends, buzzwords, and silver-bullet solutions come and go. But what hasn’t changed is the Lynch Foundation’s clarity of mission, and its ruthless commitment to proximity. Her team gets in the weeds with doers, not grifters and clout-chasers.

Katie told us, “I’m not here to make friends.” That’s not arrogance. That’s focus. That’s a lesson for school boards, district leaders, and nonprofits alike: know what you're about. And maybe more importantly—know what you’re not about. At a time when education policy can feel like a long-winded group project, I find that kind of clarity refreshing.

I hope you’ll watch the full Quality Matters episode because there are too many great takeaways to cover in this note.

The episode is available on YouTube and podcast streaming services.

Enjoy!

Join us for a thought provoking discussion that reimagines what quality education can truly mean.

Here’s a homework assignment for you (see poll below):

This question drives the work of Kerry McDonald, who leads the Education Entrepreneurship Lab at the Foundation for Economic Education and hosts the LiberatEd Podcast. During our Quality Matters conversation, Kerry gave the relatable example of a shopper choosing between an array of breakfast options: cereal, organic granola, eggs, and even yogurt.

Baylor University’s Erik Ellefsen, a veteran of school network development, brings a perspective that might surprise traditional educators. Through years of observing and building successful school communities, he's discovered that the secret sauce isn't found in perfect test scores or flawless curricula. Instead, it's in the invisible threads of relationships that bind a school community together – the trust between teachers and students, the engagement that sparks genuine learning, and the sense of empowerment that transforms passive students into active learners.

Erik’s friend Ben Bajarin, a business and technology strategist, helps us find parallels between high-performing educational environments and successful corporate teams. His insights from Silicon Valley's most successful companies reveal a fascinating truth: whether you're building a breakthrough product or nurturing young minds, the fundamental principles of organizational culture, human development, and collaboration remain constant.

Our conversation weaves together two worlds and what emerges is a vision of educational quality that goes beyond a simple, flash-in-the-pan test. It's a vision that recognizes schools as complex systems where relationships and meaningful professional development ought to be prioritized.

This episode of Quality Matters is also a reminder that when we seek the best outcomes for students, we must also consider the adults who are in room because if they aren’t growing and innovating, children will ultimately suffer.

Dr. Wolf’s emphasizes that schools must do more than improve test scores; they should instill civic virtues such as political tolerance, engagement, and respect for differing viewpoints. His meta-analysis of private and charter school effects on civic outcomes found that students in these environments often demonstrate higher levels of political knowledge and tolerance—qualities that are essential to maintaining a democracy where power transitions peacefully.

Our conversation highlights the complexities of measuring quality across diverse educational environments and examines whether families are pushed out of traditional schools or pulled into emerging ones.

Dan’s insights offer a fresh perspective on the evolving education landscape, emphasizing the need for nuanced evaluation and a deeper understanding of what parents truly value in education.

On each episode Caitlin and I speak with leaders like Chad and take the lessons they’ve learned and see how we might weave them into the K-12 education space. During this conversation we talk about keeping innovation at the forefront and we learn strategies for building consensus among your constituents. I hope you’ll give this a listen!

Gerard is a distinguished professor at the University of Virginia, bringing a wealth of expertise in education policy, criminal justice, and economic mobility. Notably, he is one of the few individuals in the nation to have held cabinet-level positions in multiple states, serving as Florida’s Commissioner of Education and Virginia’s Secretary of Education. Recently, Gerard shifted his focus toward prison reform, dedicated to enhancing educational opportunities for incarcerated individuals and advocating for a more equitable justice system.

This time we wonder what practices you’ve employed to convey your high expectations - whether for students, employees, or other people who you want to see perform at a high level?