The latest episode of Outsider, Inc. features Chris Schroeder — entrepreneur, investor, and author who’s spent the last fifteen years chasing a question most people in his position never bothered to ask.

Chris built an impressive career. Harvard. Two presidential campaigns. A State Department tour under James Baker. Wall Street, private equity, and then CEO and Publisher of WashingtonPost.com. He co-founded HealthCentral, backed by Sequoia, Carlyle, and Barry Diller’s IAC, grew it to over 15 million monthly users, and reached a successful exit. The next move was his to pick.

But in November 2010, he went to a startup gathering in Dubai, and something broke open. He realized he’d been living inside his own narrative bias, missing an entire generation of founders building across the Middle East, Asia, and Latin America. Instead of chalking it up as an interesting experience, he followed the thread.

That journey became Startup Rising, the first book on entrepreneurship in the Arab world — built on more than a dozen trips to the region and conversations with 150+ founders, investors, and operators. Chris went on to co-found Next Billion Ventures and backed exits like Careem’s $3.2 billion sale to Uber.

But the credentials aren’t really the point. What makes Chris different is that he actually goes. Millions of miles logged to places most investors don’t think about, asking better questions than the people who stayed home.

In this episode, we get into where the curiosity came from, why he walked away from the obvious path, and what fifteen years on the road has taught him about where the next great companies are actually being built. ⤵️

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Episode Highlights

Chris unpacks the power of being wrong. He illustrates this point with two bookend moments he experienced that made him permanently suspicious of expertise. From experts dismissing the fall of the Berlin Wall weeks before it happened, to others who missed the Arab Spring weeks before it erupted, he makes the case that real insight lives closer to the ground than most people think.

Next, Chris recounts a meeting where entrepreneurs from Latin America, Africa, and Asia told him the Chinese tech community understood them in a way Silicon Valley never has. What follows is a sharp take on why American investors keep missing the mark in emerging markets and what actually shows up in the room when rising markets talk to each other without the American playbook front and center.

And here, Chris lands on one of the hardest-won lessons of his career: if you understand the incentive structure, you can predict with near certainty how people will behave. I pick up the thread with a question I put to founders all the time — do you actually know how your ideal customer earns their Christmas bonus? The answer to that question provides more insight into who buys your product than you might think.

Finally, Chris makes the case that being on the ground is a completely different exercise than consuming information from a distance, because you see behaviors, talk to cab drivers, and catch the 11pm conversations over beers that you'd never get on Zoom. This gives him a more complete picture of what’s happening in the places he’s trying to better understand.

I’m super grateful for this conversation with Chris. What sticks with me about this conversation isn’t just Chris’s resume. It’s what he did in Dubai in 2010 — walking away from a path that was basically paved for him to go chase questions most people in his seat never think to ask.

He traded certainty for curiosity, expertise for exploration, and the last fifteen years have pretty clearly vindicated the call. The story lands not because of the miles logged or the deals backed, but because of the posture underneath it all. Chris has built a career on a simple idea: the most powerful move isn’t saying what you know — it’s owning what you don’t. Humility isn’t soft. It’s exploration. Being wrong isn’t a failure; it’s usually the first honest step toward getting it right-er.

If you take one thing from this episode, let it be this. The best investors, builders, and operators aren’t the ones with the cleanest answers. They’re the ones still asking sharper questions than everyone else in the room. Go. Get on the ground. Push on your own narrative bias. Don’t let the real story pass you by while you’re deferring the hard questions to a third cappuccino. The next great founder or market is almost certainly taking shape somewhere you haven’t thought to look — and the only way to find it is to show up.

Chris’s Library

During our conversation, Chris and I discussed his love of books, and his audacious goal of reading 150 new books each year. He called out a handful by name in the episode. Brief summaries and links to a few of them are below.

Startup Rising. Chris Schroeder’s on-the-ground report from a startup scene most Americans didn’t know existed. After more than a dozen trips to the Middle East and 150+ conversations with founders, investors, and operators, he came back with a simple argument: a generation of young builders across the Arab world — phones in hand, “why not us?” on their minds — was quietly reshaping what was possible in places most Western investors had dismissed. Marc Andreessen wrote the foreword and called it a potentially trillion-dollar question hiding in plain sight. This is a great book on understanding entrepreneurial ecosystems generally, and the Middle East specifically. It made my visits to the region more enjoyable and productive. I highly recommend it to anyone doing business in the region.

The Hard Thing About Hard Things. The honest version of the job of a tech CEO. Famed venture capitalist and former entrepreneur Ben Horowitz writes about the stuff nobody brags about on Twitter — laying off people you love, firing a friend, demoting a loyal exec, keeping your own head on straight when the whole thing is on fire. A lot of it comes from running Opsware through the dot-com crash and eventually selling to HP. Less a business book than a survival manual for founders in the thick of it. This is one of the first books I read on startups and was floored by how different it was from the others (and aligned with my experience working at my first company).

What You Do Is Who You Are. Another Ben Horowitz gem. His core argument is that culture isn’t your values deck or your all-hands slides — it’s what people actually do when you’re not in the room. He makes the case through four unlikely stories: Toussaint Louverture and the Haitian Revolution, samurai Japan, Genghis Khan, and the prison code of Shaka Senghor. The takeaway: culture is built through behavior, and you end up with the one you actually design, whether you meant to or not. This is one of my all-time favorite books on any subject and I recommend it to founders all the time, particularly new CEO’s who are slowly realizing that culture is destiny.

I Deliver Parcels in Beijing. A Chinese gig worker spends eight years bouncing through 18 different jobs — parcel courier, warehouse floor, convenience store, you name it — and writes about all of it. It started as a blog, went viral, and became a book. What makes it great isn’t the big picture; it’s the small stuff. The pace, the ridiculous rules (the no-bathroom-break thing is real), the quiet negotiations workers make with 996 culture and the expectations their parents still carry. Funny, sharp, sometimes gutting. It’s the China you don’t get from the experts.

Chris’s Playlist

I also ask guests what are one or two songs that has inspired them on their journey. Chris shared a vast array of musical styles that have inspired him — from Bach (which he wrote Startup Rising to) to Jazz to Korean hip-hop (he called out the artist Lee Young-ji specifically) to Quincy Jones to Kendrick Lamar. He named one specific song, Rakim’s “Paid In Full”. Chris described Rakim as a personal hero.

Up Next: Jared Polis

Tune in next week with Jared Polis — serial entrepreneur, political leader, and the sitting Governor of Colorado. Before he turned 30, Jared already built and exited three companies for over a billion dollars combined, including BlueMountain.com and ProFlowers. He went on to co-found Techstars, which has backed thousands of companies and changed how a generation of founders thinks about mentorship and community. But public service kept tugging at him. In 2008, he ran for Congress, came out during the race, and won — becoming the first openly gay non-incumbent ever elected to the U.S. House. Ten years later, he came home to Colorado and won the governor’s office, becoming the first openly gay man elected governor in US history. What makes his story interesting isn’t just the firsts. It’s how he actually does the job — more like a builder than a politician, focused on execution, systems, and outcomes. In this episode, we dig into where his entrepreneurial instincts came from, what he saw in the earliest days of Techstars that made him go all in, and where founder principles do — and do not — translate inside government.

The latest episode of Outsider, Inc. features Willy Schlacks, co-founder and President of EquipmentShare, and one of the most intentional builders we’ve had on the show.

Willy’s story doesn’t begin in a startup hub or around venture capital tables. He grew up in a cloistered environment in rural Missouri — a world with no private property, no personal ownership, and strict control over money and agency. Inside that environment, entrepreneurship didn’t show up as ambition or status-seeking. It showed up as curiosity — a way to engage with the world and learn how things worked. Alongside his brother Jabbok, Willy began building real businesses at a young age, learning through necessity how to pre-sell, reinvest profits, and operate with discipline, long before those ideas were fashionable.

When Willy left that environment in his late twenties, he effectively started over. That reset eventually led to EquipmentShare — a company born not from chasing a hot market, but from lived experience as an operator confronting work that was reactive, chaotic, and disconnected, and deciding it didn’t have to stay that way. What began as a Startup Weekend idea in Missouri grew into a vertically integrated platform spanning technology, equipment, and services — scaling into one of the largest companies in its category, and just weeks ago, going public at a $7 billion valuation.

In this episode, we trace how those experiences shape the way Willy thinks about building — from why constraints matter, to how leadership evolves at scale, to what it means to stay close to the work as the stakes grow. ⤵️

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Episode Highlights

In this first clip, Willy goes straight to the heart of what drives him—the relationship between struggle and creation. He argues that comfort, taken to its extreme, doesn't deliver peace. It delivers boredom. And boredom is the death of everything worth building. The real game, he says, looks more like music—rhythm, dissonance, and movement. The only time it stops is when you're dead. Plenty of time to rest then.

In this next clip, Willy reframes what most people call failure, arguing the word itself is the problem. Mistakes aren't wrong turns; they're just movement. His advice to founders is less about tactics and more about orientation: start with yourself, stay authentic to what you actually feel, and stop applying moral wrappers to the things you chase. The path, he says, begins and ends with you.

And here, Willy answers the question most people around him got wrong — why Missouri instead of Silicon Valley. Most thought it was a foolish choice. His answer is almost disarmingly simple: Missouri was home. But what follows is a deeper argument about the difference between a place you land and a place you manufacture from a checklist — and why only one of them has any real roots to it.

Finally, Willy reflects on the unexpected gift of his unconventional upbringing — it taught him early not to conform. The real obstacle, he says, isn't hardship. It's a comfortable, easy childhood. And it's something he worries about with his own kids.

I’m grateful for my conversation with Willy. He’s one of those rare people who has thought deeply about the relationship between constraint and creation—not as an abstract philosophy, but as something he’s lived from the beginning. From early on, Willy developed a clarity of purpose that I think is almost impossible to manufacture later in life. That’s what makes his story so worth sitting with.

What I took most from this conversation is how countercultural his whole orientation really is. In a world that rewards optimization for comfort—the right city, investors, and network—Willy kept choosing the harder thing. Missouri over Silicon Valley. Constraint over ease. Roots over relocation. And the result isn’t just a $7 billion company. It’s a way of building that has integrity all the way down, because for Willy, it was never about chasing the signal. It was always about the work.

If there’s one thing Willy would want you to take away, it’s this: stop waiting for the conditions to be right. Constraint isn’t the enemy of building—it’s the engine. You don’t need everything to be perfect, you just need the discipline to stay in motion and the belief that the friction is the point. The only thing standing between you and what you want to build is the story you’re telling yourself about why today isn’t the day.

Willy’s Library

During our conversation, Willy called out three books he enjoys, mentioning Range specifically as one that founders should read. He also mentioned his admiration for Henry David Thoreau. But since he didn’t offer a specific Thoreau book, I chose one. Brief summaries and links to all four are below.

Range: Why Generalists Triumph in a Specialized World, by David Epstein. A counterintuitive and thoroughly researched argument that generalists, not specialists, are better positioned to thrive in complex, unpredictable domains. Epstein challenges the “10,000 hours” gospel popularized by Malcolm Gladwell, showing through a wide range of evidence that breadth of experience, late starts, and cross-domain thinking are often significant advantages rather than liabilities. The book draws on examples from sports, science, music, and business to make the case that the most creative and adaptable people are rarely the ones who specialized earliest. For founders — especially those who came to entrepreneurship through an unconventional path — it’s both a vindication and a call to lean further into what makes them different.

Team of Rivals, by Doris Kearns Goodwin. The definitive account of how Abraham Lincoln built his cabinet by deliberately surrounding himself with his most formidable political opponents. Goodwin spent years in the archives reconstructing not just the political history but the interior lives of the men involved, and what emerges is a portrait of leadership that is as much about emotional intelligence and self-awareness as it is about strategy. Lincoln’s ability to absorb criticism, subordinate his ego, and hold together a fractious team under the most extreme conditions imaginable is the throughline. More than a Civil War history, it’s a study in what resilience actually looks like when the stakes are civilizational.

Duel: Alexander Hamilton, Aaron Burr, And The Future Of America, by Thomas Fleming. The story of the famous confrontation between Alexander Hamilton and Aaron Burr, but really a window into the founding era’s raw ambition, rivalry, and moral complexity. Fleming brings both men to life with novelistic detail, tracing the long arc of tension between two of the most brilliant and flawed figures of the early republic. What makes the book so compelling is how fully it captures the human dimensions of the story — the pride, the grievance, the miscalculation — in a way that dry historical accounts rarely manage. For anyone who has ever been drawn to the idea that character is destiny, it’s a hard book to put down.

Walden: Life in the Woods, by Henry David Thoreau. Thoreau’s account of two years living deliberately in the woods outside Concord, Massachusetts, stripping life down to its essentials and paying close attention to what remained. It is part memoir, part philosophy, part provocation — a sustained argument against the kind of busyness and conformity that Thoreau believed kept most people from ever truly living. The prose is dense and rewards patience, but the ideas have a way of staying with you long after you’ve finished. It gave Willy one of his favorite framings: that life pursues us more than we pursue it — that the most meaningful arrivals are the ones we never quite planned for.

Up Next

Tune in next week with Chris Schroeder — entrepreneur, venture investor, and author who spent the last decade and a half challenging one of the biggest blind spots in global entrepreneurship. Chris built an extraordinary career: Harvard, two presidential campaigns, Wall Street, and ultimately CEO of Washington Post online, before co-founding HealthCentral and leading it to a successful exit. The path forward was well-paved. But in November 2010, at a startup gathering in Dubai, something shifted. He realized he'd been completely blind to the massive wave of entrepreneurship taking shape across the Middle East, Asia, and Latin America — and he chose a different path. That awakening led to Startup Rising, the first book on startups in the Arab world, and investments like Careem ($3.2B sale to Uber). In this episode, we trace where his curiosity came from, what it took to turn toward the places others overlooked, and what fifteen-plus years on the ground has actually taught him.

The latest episode of Outsider, Inc. features David Cohen, the co-founder and CEO of Techstars, serial entrepreneur, and one of the most consequential figures in venture capital and entrepreneurial ecosystems over the last two decades.

Before Techstars, David was a founder himself—building companies, experiencing real wins and real failures, and learning firsthand what early-stage entrepreneurs actually need when the system isn’t designed to help them. Out of that experience came a radically different approach to investing and mentorship—one rooted in trust, long-term thinking, and community, rather than short-term transactions or manufactured hype. What began as a small experiment in Boulder grew into a global network behind companies like DigitalOcean, Zipline, and SendGrid, reshaping how founders are supported in markets that Silicon Valley largely ignored.

Through Techstars Ventures, David was also a first-check investor in Twilio and made one of the largest returns in venture history with a first-round bet on Uber. He recently returned to the CEO role at Techstars at a moment of real change—for founders, for ecosystems, and for the venture industry itself.

In this episode, we trace the full journey—from his earliest companies and influences, to the philosophy behind Techstars, the hard tradeoffs of scale and culture, and the work he believes is still unfinished for the next generation of outsiders. ⤵️

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Episode Highlights

In this first clip, David traces the origin of Techstars to a humbling realization—after selling his first company, the acquirer told him he'd left half the money on the table. That sting pushed him to ask harder questions. What he found was a pattern. The things that worked almost always had experienced people around them. Networks matter. That insight, and a "no" from Paul Graham when David asked to bring Y Combinator to Boulder, set him on a different path—one that became Techstars.

In this next clip, David breaks down his investment framework—team, team, team, market, progress, idea—and why team comes first, second, and third. At the earliest stages, the idea will shift and the market will evolve, but the team is what determines whether founders can feel their way through the dark and stay alive long enough to figure it out. The signal he looks for is intrinsic motivation, where founders are doing it for some reason other than a spreadsheet.

In this clip, David shares the founder trait he thinks the rest of the industry overvalues in founders—experience. At the earliest stages, it can actually be a liability—founders trying to change the world in genuinely new ways don't need to know how everyone else did it before them. In fact, that knowledge can get in the way.

Finally, David gets personal about what the first thirteen years at Techstars cost him—his identity wrapped up in the company, working until three in the morning, traveling too much, a Fitbit chart that told the whole story every time they raised a fund. Coming back as CEO, he committed to doing it differently—exercising, prioritizing family, and building in time for rest. For him, that’s meant padel—a sport he loves enough to have built a five-court club in Boulder, playing almost every day, often in the middle of the afternoon. The lesson he keeps coming back to—you can sprint so hard you lose the marathon. Work-life balance may be a myth, but harmony isn’t.

I’m grateful for my conversation with David. He’s been a mentor to me, and someone whose philosophy has quietly shaped the way I think about this work. David’s story is a reminder that the most durable things in venture aren’t built from pattern-matching; they’re built from relationships, trust, and a genuine commitment to the person across the table. When the ecosystem isn’t there, David didn’t wait for someone else to build it for him. He showed up, gave first, and bet on people before the evidence was in.

What I took most from this conversation is how countercultural that really is. In an industry that rewards speed, scale, and signal, David spent two decades optimizing for something slower and harder to measure—community. Not as a brand, but as a practice. And what he’s modeling right now—returning to lead the organization he built, trading growth for quality, choosing depth over reach—is a kind of discipline that most people only discover after they’ve already lost something important.

If there’s one lesson David leaves us with, it’s this—surround yourself with great people, give before you take, and don’t mistake momentum for progress. And always remember, bigger isn’t better. Better is better.

David’s Library

In the Beyond the Bio segment of each episode, I ask guests a number of quick hit questions that let’s listeners get to know them beyond their resume. One question I ask guests each time is what are one or two books they recommend to entrepreneurs. David named one that he recently came across. And, although we didn’t discuss it in the episode, David co-authored with friend-of-the-pod Brad Feld.

Anyone Builds It, Everyone Dies: a New York Times bestselling alarm bell from Eliezer Yudkowsky, a founding researcher of AI alignment, and Nate Soares of the Machine Intelligence Research Institute, arguing without apology that the race to build artificial superintelligence is not an arms race but a suicide race. The core case is deliberately simple: modern AI systems are grown rather than crafted, their inner workings opaque even to their builders, and a system that genuinely surpasses human intelligence would pursue its own goals with a competence that leaves us no recourse. Critics have called it tendentious and thin on opposing views, and those critiques have merit. But the questions it raises are serious ones the AI industry has not answered to anyone’s satisfaction, and its willingness to call out wishful thinking from prominent figures at the frontier labs gives it a credibility more cautious treatments lack. A direct and accessible statement of the existential risk case yet published. Anyone building companies, allocating capital, or making policy in the age of AI should engage with it.

Do More Faster: a practical field manual disguised as a book, co-authored by Techstars co-founders David Cohen and Brad Feld and built from the ground up out of the hard-won lessons of founders and mentors who actually lived them. The book is structured as a collection of short, direct chapters organized around seven themes: ideas and vision, people, working effectively, product, fundraising, legal structure, and work-life harmony; each is written by founders and mentors from inside the Techstars network, including Tim Ferriss, Eric Ries, and Matt Mullenweg. Cohen and Feld aren’t trying to write the definitive theory of startups. They’re trying to compress the most useful advice into the smallest possible footprint, and hand it to founders who don’t have time to waste. It is refreshingly dense and direct. The book reads like a mentorship session with people who have seen every mistake and want to help you skip the ones that don’t teach you anything. For anyone building at the earliest stages, particularly outside the traditional networks where that kind of mentorship is hardest to find, it remains one of the most honest and useful guides available.

David’s Playlist

I also ask guests what are one or two songs that has inspired them on their journey. David shared what is one of my long-time favorites: Money by Pink Floyd. This song will always remind me of my dad, who gave me my first CD as a young kid—Pink Floyd’s The Dark Side of the Moon, which launched this iconic song.

Up Next

Tune in next week for a conversation with Willy Schlacks, co-founder and president of EquipmentShare, and one of the most intentional builders we've had on the show. Willy grew up in a cloistered environment in rural Missouri with no private property, no personal ownership, and strict control over money and agency. Entrepreneurship showed up not as ambition but as curiosity. When he left in his late twenties and effectively started over, that reset eventually led to EquipmentShare—a company born not from chasing a hot market, but from lived experience as an operator who decided the chaos didn't have to stay that way. What began as a Startup Weekend idea in Missouri scaled into one of the largest vertically integrated platforms in its category, recently taken public at a $7 billion valuation—one of the largest tech exits outside Silicon Valley in recent years. In this episode, we trace how those experiences shaped the way Willy thinks about building—why constraints matter, how leadership evolves at scale, and what it means to stay close to the work as the stakes grow.

The latest episode of Outsider, Inc. features Hernán Kazah—Co-Founder and former COO/CFO of Mercado Libre, Co-Founder and Managing Partner of Kaszek, and one of the foundational architects of Latin America's technology ecosystem.

More than two decades ago, Hernán and his co-founders built Mercado Libre from scratch — an online marketplace for a region where internet adoption was near zero, capital was scarce, and no real tech ecosystem existed to lean on. They survived the dot-com crash, took the company public on the Nasdaq, and built what became one of the most important technology companies ever built outside Silicon Valley — today trading at a market cap north of $100 billion.

But Hernán didn't stop there. After more than a decade as a founder and operator, he stepped away in 2011 to co-found Kaszek — deliberately applying everything he'd learned to backing the next generation of Latin American entrepreneurs at the earliest stages of their journeys. Kaszek has since backed many of the companies that now define the region's modern tech ecosystem: Nubank, QuintoAndar, Creditas, Gympass, and Kavak — becoming the most influential venture firm in Latin America, and helping transform what was once a fragile, fragmented startup scene into something far more sustaining.

What makes Hernán's story different isn't just the scale of what he's built — it's the perspective earned by living through every phase: founder, operator, public-company executive, and venture investor. He's seen firsthand how much of success comes down to timing, discipline, and resilience — especially in markets that don't move on Silicon Valley's schedule.

In this episode, we dig into what those experiences teach you about trust, conviction, and patience — and what it really means to build things that last in markets where the path forward is rarely obvious. ⤵️

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Episode Highlights

Below are a few highlights from my interview with Hernán. In this first clip, Hernán shares what he looks for when evaluating founders — breaking it down into team, business model, and market — with a particular emphasis on that irrational, almost compulsive commitment to solving a problem that separates the founders who survive the hard moments from those who don't.

In this next clip, Hernán explains what makes building in Latin America fundamentally different from Silicon Valley — where infrastructure gaps force founders to solve far more than their core problem, but in doing so, they often end up building something more defensible and valuable than they originally set out to create.

And here, Hernán reflects on a formative moment at Stanford — meeting icons like Steve Jobs, Bill Gates, and Warren Buffett — and how seeing them up close didn't diminish his admiration, but instead made him realize that the distance between himself and greatness was smaller than he'd imagined. At the end of the day, we’re all just people.

Finally, Hernán talks about why Kaszek was built specifically around Latin America — where their operational experience and regional networks gave them a genuine edge — and how in the early days, that meant doing far more than just writing checks, actively guiding founders through the mechanics of building a venture-backed company in an ecosystem that was still finding its footing.

I’m thankful for my conversation with Hernán for sharing his deep wisdom, hard-earned insights, and commitment to the region. Hernán’s story is a reminder that “outsider” isn’t a disadvantage — it’s a forcing function. When the ecosystem isn’t there, you can’t lean on momentum. You have to manufacture it. You don’t just build a company — you build the conditions around it: trust, infrastructure, resilience, and eventually, belief.

What I took most from this conversation is how quietly disciplined that really is — confidence without ego, patience without passivity, ambition with a long-term lens. Because in the end, the people who change a market aren’t the ones with the cleanest plan — they’re the ones who stay standing long enough for the plan to become real. And if there’s one lesson Hernán leaves us with, it’s this: act out of conviction, or don’t act at all.

Hernán’s Library

In the Beyond the Bio segment of each episode, I ask guests a number of quick hit questions that let’s listeners get to know them beyond their resume. One question I ask guests each time is what are one or two books they recommend to entrepreneurs. Hernán suggested two.

The Snowball: Warren Buffett and the Business of Life: is the definitive biography of Warren Buffett, written by renowned financial journalist Alice Schroeder. It traces his life from a numbers-obsessed kid in Omaha to the most celebrated investor in history. Drawing on unprecedented access to Buffett himself, Schroeder paints an intimate and sometimes unflattering portrait of a man whose genius for compounding capital was matched by a complex, often emotionally distant personal life. The book's central metaphor — wet snow and a long hill — captures Buffett's core philosophy: start early, stay disciplined, and let time do the work. Through his partnerships, his acquisition of Berkshire Hathaway, and his relationships with figures like Charlie Munger and Katharine Graham, Schroeder shows how Buffett's investment mind was inseparable from his personality — frugal, relentlessly curious, and single-mindedly focused on the accumulation of wealth, even when it came at a cost to the people closest to him.

Steve Jobs: an authorized yet unsparing biography of one of the most singular figures in the history of technology and culture, by iconic biographer Walter Isaacson. Based on over forty interviews with Jobs himself — who requested no editorial control — as well as hundreds of conversations with family, friends, rivals, and colleagues, Isaacson chronicles the full arc of a life defined by breathtaking creative vision and equally breathtaking personal cruelty. From his adoption and coming-of-age in Silicon Valley, through his early days at Apple, his exile and reinvention at NeXT and Pixar, and his triumphant return to build the iMac, iPod, iPhone, and iPad, the book reveals a man who believed reality was something to be bent to his will — and who was often right. Isaacson doesn't shy away from Jobs' darker qualities: the manipulation, the mood swings, the casual dismissal of people he'd previously championed. But what emerges is a portrait of someone who understood, more deeply than almost anyone, that technology and the humanities were not opposites — and that the intersection of the two was where truly great things got made.

Hernán’s Playlist

Also in the Beyond the Bio segment, I ask guests what are one or two songs that has inspired them on their journey. Hernán gave us two classics: Mixed Emotions by the Rolling Stones, and Eye of the Tiger by Survivor.

Up Next

Tune in next week with David Cohen, co-founder and CEO of Techstars, whose conviction that the best founders aren’t always concentrated in a handful of zip codes — and that the right support, built on trust rather than transaction, could unlock them anywhere — quietly reshaped how the venture world thinks about outsider markets. Before Techstars became a global platform launching companies like SendGrid and Digital Ocean, and before David became a first-check investor in generational companies like Uber and Twilio, he was a tech founder himself — learning firsthand what early-stage entrepreneurs actually need when the system isn’t designed to help them. That experience became the blueprint. It’s a conversation about building for the long game, investing in places others overlook, and the work David believes is still unfinished for the next generation of outsiders.

Legacy is one of those words that gets heavier the longer you sit with it.

It’s not about the press release, the valuation, or even the exit. It’s about what happens after you’re gone. What people remember. What they carry forward. What they build because you showed them it was possible.

Most founders don’t think about legacy while they’re in the thick of it. They’re thinking about payroll, product market fit, the next round, the next crisis. Legacy feels like something you earn the right to consider later, once you’ve survived long enough to look back.

But the truth is, legacy isn’t something you think about at the end. It’s something you’re building every day, whether you realize it or not. In the people you hire. The communities you invest in. The barriers you break down. The example you set for someone watching from the outside, wondering if they could do it too.

Inevitably, most episodes of Outsider Inc. wind down with themes of legacy and the impacts they’ve made.

When you think about the ripple effects of your work, what are you most proud of?

What do you most hope endures?

The answers are never about the company alone. They’re about access. Opportunity. Empowerment. The next generation. Some are deeply personal. Others are system-level ambitious. Hearing their answers reminds me why telling their stories is so important.

This compilation brings together these special moments from 17 of our guests. It’s not about what they’ve built. It’s about what they hope outlasts them.

If you’re building something, or thinking about what you want your work to mean in the long run, I hope you hear something here that shifts how you see it.

All of the stories of how they got there are waiting for you, too.

👉 Watch the full video and explore every episode of Outsider Inc.

Listen to Outsider Inc. on: Spotify, Apple Podcasts, Amazon Music

I ask our guest one simple question:

If you could give one piece of advice to someone starting their founder journey, particularly someone who is a bit of an outsider, what would it be?

Across founders, investors, operators, and ecosystem builders, the advice keeps circling the same truths. Start before you feel ready. Don’t wait for permission. Ask for help sooner than you think you should. Build something real for a real person. Stay in it long enough to learn what only experience can teach you.

Some answers are blunt. Some are generous. A few are funny in the way only hard-earned wisdom can be. But together, they form a chorus. A reminder that while entrepreneurship is deeply personal, the lessons don’t have to be learned alone.

This compilation brings together these special “Beyond the Bio” moments from our first twenty episodes. It’s not a highlight reel of wins. It’s a snapshot of what people wish they had understood earlier, when the path was less clear, and the stakes felt impossibly high.

If you’re building from the outside, or even just thinking about it, I hope you hear something here that sticks. And, in Phil Knights words: “Just do it.”

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The latest edition of Outsider Inc. features Seth Levine—Co-Founder and General Partner at Foundry, Co-Author (with Elizabeth MacBride) of The New Builders: Face to Face With the True Future of Business, and the just-released Capital Evolution: The New American Economy, Co-Founder of Pledge 1%, and one of Colorado's most influential voices in entrepreneurship for nearly 20 years.

Seth and his Foundry partners built a firm that redefined what venture capital could look like outside the coasts. They backed companies like Fitbit, Zynga, AvidXchange, and SendGrid from a base in Boulder, demonstrating that a top-tier platform could thrive far from Silicon Valley. Foundry became a blueprint for how an outsider thesis executed with discipline and humility can outperform the status quo.

But Seth's work extends well beyond that. He's advised founders and funds across the Middle East and Africa, helped elevate a new generation of diverse fund managers, and recently co-founded GoodBread, a lending platform built for the entrepreneurs that traditional finance consistently overlooks.

Tune in to learn about the unconventional path that led Seth into venture, how Foundry's outsider mindset became its competitive edge, and what he's learned from spending two decades working across ecosystems in the US and abroad. ⤵️

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Episode Highlights

Below are a few highlights from my interview with Seth. In this first clip, he makes a forceful case for entrepreneurship as a practical engine for job creation and innovation—even if it isn’t a silver bullet for every problem. He also reveals a deeper concern that the U.S. is losing its economic dynamism as access narrows and gatekeepers increasingly reward connections over merit. Seth is optimistic about what founders can unlock, but clear-eyed—and a little alarmed—about the structural barriers that keep too many people from getting a real shot.

In this next clip, Seth tells a humorous, self-aware “bubble burst” story from the IPO whirlwind—one moment feeling untouchable in a stretch limo on the way to Newark airport, the next realizing his flight was actually out of JFK and watching his whole plan implode. What stands out to me is how quickly he turns the mishap into a personal check: a reminder that success can inflate your ego in real time, and life has a way of correcting that. It’s a good insight into Seth—ambitious and in the arena, but grounded enough to laugh at himself and take humility seriously.

And here, Seth reflects on how Foundry’s early belief—that you could help build real startup ecosystems outside the Bay Area and Boston—has largely played out over the last 20 years, as serious entrepreneurial markets emerged across the country. He also makes clear what they were drawn to as investors: scrappy founders who’d been overlooked, had something to prove, and kept pushing even when fundraising was hard. You can hear Seth’s conviction that great outcomes aren’t reserved for the obvious geographies or the “easy” companies, and that backing underestimated people in underestimated places can be both principled and profitable.

Finally, Seth explains what pulled him into telling the story of “the new builders” in American entrepreneurship—how the face of business creation is shifting toward more women, immigrants, and founders of color, yet the capital and support systems haven’t caught up. What started as a plan to spotlight overlooked, non-traditional entrepreneurs became, through research, a much bigger indictment of how resources get allocated—and how distorted our mental image of “entrepreneur” has become because we mostly see venture-backed tech. Admirably, Seth doesn’t just want to observe the gap; he’s intentionally using his platform and credibility to amplify those stories in places that can change outcomes, including policy circles.

I’m thankful for my conversation with Seth; not only for his wisdom and mission, but for the deep motivation behind it. Conversations like this are a good reminder that outsider isn't just a brand. It's a choice about how you show up in the world, with humility, with a bias to give first, and with a stubborn belief that entrepreneurship can expand who gets a real shot. I'm struck by how Seth has lived those values across many different arenas: venture capital, small business, and fostering ecosystems around the world. My hope is that listeners walk away a little more committed to supporting overlooked builders in their own backyard, and a little more convinced that the future of capitalism depends on who we invite in.

Seth’s Library

In the episode, we discussed both of Seth’s published books, as well as two others he recommends for founders to read. Here’s a brief overview of each:

In The New Builders: Face to Face With the True Future of Business, Seth and co-author Elizabeth MacBride give a grounded look at where American entrepreneurship is actually headed—and who’s driving it. They argue that our cultural definition of entrepreneur has narrowed (too much Silicon Valley, not enough Main Street), while the fastest-growing—and most under-supported—builders include women, people of color, and founders over 40. It’s part narrative reporting, part economic wake-up call, and it will change how you think about the future of business. If you care about economic dynamism, you don’t just need more startups—you need more access to the messy, local, durable kinds of companies most people overlook.

In the recently-released Capital Evolution: The New American Economy, Seth and Elizabeth are back with a compelling book that zooms out from entrepreneurs to the system itself: how capitalism is evolving (or failing to), and what a more functional next era could look like. Their core frame is that the future isn’t a binary political choice—it’s about updating institutions, incentives, and trust so the economy works for more people (and stays resilient). The book is built around case-driven storytelling and a practical call to action: less ideology, more iteration, and what would we change if we treated the economy like a product that needs a version upgrade.

The first of two books Seth recommended is Essentialism: The Disciplined Pursuit of Less, by author and strategist Greg McKeown. In it, McKeown puts forward a classic operating system for focus: discern what’s truly essential, eliminate the rest, and create the space to do the right things really well. It’s not a productivity hack so much as a philosophy of tradeoffs—especially valuable for founders who keep saying yes until they’re managing chaos instead of building momentum. If everything is important then nothing is. What you say no to defines you, too.

Seth also recommended Subtract: The Untapped Science of Less, by University of Virginia professor Leidy Klotz. Subtract is a book about a bias most of us don’t realize we have: when something needs fixing, we reflexively add—features, process, people, meetings—instead of considering subtraction. Klotz blends behavioral science and design to show why “less” is harder to see, and how deliberately removing can be the fastest path to better systems, better products, and a calmer organization. Before you add, ask: what can we remove to get the same (or better) result?

Thank you

We’re going to take a short hiatus for the holidays, then we’ll be back on our regular cadence shortly after the new year. Look for the next episode in late January / early February—and yes, it’s a really good one. In the meantime, we’ll share a few pieces that recap Outsider Inc.’s incredible first year. Keep an eye out for those.

To our subscribers, listeners, and guests: thank you. This was an unforgettable inaugural year. We created twenty episodes that didn’t just spotlight improbable outcomes, but also offered a window into the people behind them: their doubts, their decisions, their scars, their grit, their joy. I feel genuinely humbled to have had the chance to host these conversations—and grateful that many of these founders are people I’m lucky to call friends. You made this year truly special.

And I want to close by thanking the team that made this possible: Steve Petchenik and Andy Shore from Spellbinder Media. You exceeded every expectation I had for what we could build in just a few months, and you made the work better at every step—creative, crisp, and relentlessly professional. I truly couldn’t have done this without you. And most importantly, it feels like we’re just getting started.

Thanks again to all of you. Wishing you a happy holiday season—and a healthy, productive start to the new year.

The latest edition of Outsider Inc. featured Gail Goodman, an early SaaS pioneer, small-business advocate, and one of the earliest women to lead a modern software platform from startup to IPO as the founder and longtime CEO of Constant Contact. Gail took the helm in 1999—long before SaaS was a buzzword—with a simple but ambitious mission: help small businesses stay connected to their customers.

Over the next 17 years, Gail led the company to an IPO and ultimately to a $1.1 billion acquisition, demonstrating that you can build a billion-dollar software business by patiently and profitably serving customers that most of the industry ignored. Under Gail’s leadership, Constant Contact grew to hundreds of thousands of customers worldwide, helping normalize ideas now taken for granted: customer-first design, human-assisted onboarding, and a disciplined, data-driven approach to growth.

Since stepping down in 2016, Gail has continued to shape the next generation of entrepreneurs as a board member at Shopify, Mindbody, Jobber, and ShipBob, as a mentor with MassChallenge and Techstars, and through nonprofit work with Entrepreneurship for All (EforAll). Tune in now ⤵️

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Episode Highlights

Below are a few highlights from my interview with Gail. In this first clip, she argues that business is a team sport you only really learn by doing; that too many founders skip the apprenticeship phase, so they never develop the pattern recognition to align a team, set culture, and drive disciplined execution. The idea and market matter, she says, but in a resource-constrained SaaS startup, if everyone isn’t rowing in the same direction, you waste precious runway and never get that great idea to market or keep customers long enough for it to count.

In this next clip, Gail explains how she stopped trying to solve everything alone and built a small peer group of non-competitive SaaS CEOs she could call whenever she hit a problem she hadn’t seen before—trusted partners who were “cracking the same nut” from different angles. Over time, she also learned how to use her investors and, crucially, a great startup lawyer not just as deal people, but as true counselors and thought partners.

And here, Gail shares how Constant Contact grew by obsessing over the real customer journey—watching users struggle in real time, removing friction, and running endless “test, scale, tune” experiments instead of just worshiping dashboards. With a cross-functional team manically focused on conversion and retention and a well-timed “coach” call rather than a hard sell, they created an experience that felt high-touch to customers while still working at SaaS scale.

Finally, Gail describes how selling Constant Contact felt less like a victory and more like a death—she was flooded with “woulda, coulda, shoulda” doubts about every decision that might have changed the outcome. To process that grief and self-critique, she sat down and wrote her “all the things I f’d up” memo just to get it out of her system.

I really enjoyed this incredible conversation with Gail, not only for the inspirational Constant Contact success story, but for the motivation behind it. What lingers for me most isn’t just the NASDAQ ticker tape—it’s the picture of a builder who sat humbly beside her customers, asked open questions, and aligned a team so tightly that execution became a love language. Gail reminds us that small businesses aren’t just a “segment”; they’re a community. And if you truly delight them, they’ll carry you further than any playbook ever could. For the outsiders listening: choose a small beachhead, keep turning the flywheel, and let focus and integrity do their quiet compounding. And always remember, your people gut, may be the most important metric of all.

Engagement Marketing

Although we didn’t discuss it in the episode, Gail published a book in 2012 on how small businesses can effectively leverage digital media to grow their businesses.

In Engagement Marketing: How Small Business Wins in a Socially Connected World, Gail argues that the real growth engine for small businesses isn’t flashy advertising, but systematically turning existing customers into loyal advocates who bring in new business. Drawing on her Constant Contact experience, Gail frames “engagement marketing” as the art of serving customers so well that they want to stay connected with you online, hear from you regularly, and recommend you to their own networks—essentially industrializing word-of-mouth in an era of social and mobile technology.

The core idea is the “Engagement Marketing Cycle,” a three-step framework: first, deliver a memorable customer experience so people leave with a positive emotional impression; second, invite them to stay in touch by opting into email lists or social channels while that experience is fresh; and third, consistently engage them with useful, interesting, and interactive content that keeps your business top of mind. When customers interact with that content—liking, sharing, commenting, forwarding emails—they not only deepen their relationship with you but also create public signals that expose your business to new prospects. Over time, this cycle compounds: engagement drives social visibility, strengthens all your other marketing, and nurtures prospects until they’re ready to buy.

The book is practical, using case studies and concrete tactics from small businesses and nonprofits that have used these methods to increase repeat sales and weather tough economic conditions. She breaks down what to post, how often, and how to blend education, conversation, promotions, and events so that engagement doesn’t devolve into constant “buy now” pitches that turn customers off. The book is less a theoretical marketing treatise and more a playbook for resource-constrained owners: a step-by-step blueprint for building a simple, repeatable system that converts everyday customer interactions into a steady stream of referrals and repeat business.

Up Next

Tune in next week when our guest is Seth Levine, co-founder and partner at Foundry, co-author of The New Builders and the just-released Capital Evolution, co-founder of Pledge 1%, and one of Colorado’s most influential voices in entrepreneurship.

For nearly 20 years, Seth and his partners built Foundry into a firm that redefined what venture capital could look like outside the coasts. They backed companies like Fitbit, Zynga, and AvidXchange from a base in Boulder, proving that a top-tier platform could thrive far from Silicon Valley, all while championing

founders who weren’t getting a fair shake from the traditional venture capital and allocator worlds. Foundry isn’t just another fund—it’s a blueprint for how an outsider thesis, executed with discipline and humility, can outperform the status quo.

But Seth’s work extends well beyond that. He’s advised founders and funds across the Middle East and Africa, helped elevate a new generation of diverse managers, and recently co-founded GoodBread, a lending platform built for the entrepreneurs that traditional finance consistently overlooks.

Tune in next week to learn about the unconventional path that led Seth into venture, how Foundry’s outsider mindset became its competitive edge, and what he’s learned from spending two decades working across ecosystems in the U.S. and abroad.

The latest edition of Outsider Inc. featured Kyle Porter, the founder and longtime CEO of Salesloft, the Atlanta-based company that pioneered sales engagement as a software category. Under Kyle’s leadership, Salesloft scaled to unicorn status in 2021 and ultimately reached a $2.3 billion valuation the following year with a majority investment from Vista Equity Partners. Along the way, Salesloft became one of Atlanta’s most celebrated startups, known as much for its culture and values as for its technology and business success. But Kyle’s story isn’t just about building a multi-billion-dollar company. It’s also about resilience: from overcoming childhood health challenges to a life-changing turning point in college to balancing the intensity of hyper growth with family life. Tune in now to hear how Kyle turned setbacks into defining moments, what it means to lead with love as a CEO, and how he sees the future of Atlanta’s thriving tech ecosystem.

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Episode Highlights

Below are a few highlights from my interview with Kyle. In this first clip, he describes a turning point where he realized he was wasting his gifts and consciously chose to use his work—and ultimately his company—as a vehicle to serve others and create an environment where people could grow, contribute, and find real fulfillment. Kyle’s story is about redefining ambition—shifting from “how big can my company get?” to “how much human potential can this company unlock”. This clip is a great insight into that mindset.

In this next clip, Kyle shares his belief that strategy has to be anchored in mission: if a company’s “why we exist” isn’t being fulfilled by the current product, you have a responsibility to change course, even if it’s painful. It’s a reminder that purpose isn’t a slogan—it’s a decision-making filter that should force hard choices when the work and the mission fall out of alignment.

And here, Kyle pushes back on the idea that founding has to be lonely or that your entire identity should be wrapped up in your company, explaining how deliberate vulnerability with his inner circle and grounding his self-worth in his faith kept him from being defined by Salesloft. To me, it’s a mental-health blueprint for founders: architect a support system on purpose and anchor who you are in something that won’t rise and fall with your startup’s valuation or success metrics.

Finally, Kyle argues that everyone has a unique edge, and your job is to relentlessly apply it in service of the world—treating setbacks as experience, seeking out tough feedback, and surrounding yourself with people who push you to learn faster than your own trial-and-error. To me, it’s a playbook for compounding growth: purpose plus persistence and a feedback-rich environment shapes individual talent into something close to unstoppable.

I really enjoyed this conversation with Kyle, not only for the Salesloft story, but for the clarity behind it. “Lead with love” wasn’t a slogan but a hard filter. Clear conscience living and purposing his talent into the service of others defined Salesloft’s culture and guided his toughest calls. The Vista chapter reinforced a simple truth: anchor identity to the mission, not the title. The blueprint: define why you exist, let values guide strategy, and keep obsession aimed at the customer. There’s no doubt that Atlanta’s ecosystem is stronger because of Kyle’s example.

Kyle’s Library

In the episode, Kyle name-dropped several books—some of which I have read and enjoyed deeply, others are now on my to-read list. Here’s a brief overview of each, along with Kyle’s commentary from the episode:

Tony Hawk: Professional Skateboarder: In this autobiography (co-written with Sean Mortimer), Hawk tells his story from being a hyper-competitive, often-misunderstood kid to becoming one of the world’s most influential skateboarders, covering the breakthroughs, slam-heavy setbacks, and evolution of modern skate culture along the way. Kyle’s big takeaway from the book: “once you’ve achieved proficiency, take your specialty to a level that fellow specialists can appreciate. Innovate. that’s what will set you apart when you become a pioneer of pioneers. And to me, when I read that, I was like… I just want to keep going and keep going and keep going and never kind of be satisfied that I’ve…. reached the level of what I wanted to achieve.”

Man’s Search for Meaning: Viktor Frankl’s reflection on his years in Nazi concentration camps and the psychological insight that people can endure almost any suffering if they can locate a deeper purpose in it. He then lays out his theory of logotherapy—the idea that our primary drive is not pleasure or power but the search for meaning, which we can find through work, love, and the attitude we take toward unavoidable suffering.

Kyle’s lens: “Here you have someone who has been in concentration camps, beaten, cold, naked, afraid, and Viktor Frankl comes to the conclusion that while there’s things in his life that he cannot change at all, which is what happens to him, he has complete control over how he responds to that moment. I think that’s the most empowering thing in the world, that everything can be taken from us, but the last of our human freedoms to choose our attitude in any given set of circumstances, we choose our own way, and I think that if he can do it, then anybody can.”

The Advantage: Why Organizational Health Trumps Everything Else In Business: this business classic from author Patrick Lincioni argues that an organization’s biggest competitive edge isn’t strategy or technology but organizational health: a cohesive leadership team, clear and aligned purpose, and a culture of trust and accountability. Lencioni lays out a practical playbook for achieving this—build a healthy leadership team, create clarity about why the organization exists and how it behaves, over-communicate that clarity, and reinforce it through every process and people decision. Kyle called it ”the closest thing to a playbook that we used at the company.” He said: “It’s incredible. I think if you just ran a business from that one book, you could do well without reading another book.”

Setting the Table: The Transforming Power of Hospitality in Business: restaurateur Danny Meyer’s memoir-manifesto about how “enlightened hospitality”—putting employees, guests, community, suppliers, and investors (in that order) at the center of every decision—built Union Square Cafe, Shake Shack, and a family of beloved restaurants. He argues that in any business, long-term success comes less from flawless operations than from how you make people feel, and he offers practical lessons on leadership, culture, service, and handling mistakes with grace. Kyle said: “I mean, it’s just so good. You could teach someone to set the table well, but you can’t teach someone to want to set the table well.”

How to Win Friends and Influence People: Dale Carnegie’s classic principles—show genuine interest in others, listen well, avoid criticism, give honest appreciation, and appeal to people’s interests. It’s a handbook on building trust, influence, and strong relationships by focusing less on what you want to say and more on how you make other people feel. Kyle said: “Everyone should just read that like every other year.”

Up Next

Tune in December 3 with Gail Goodman—SaaS pioneer, small business advocate, and one of the earliest women to lead a modern software platform from startup to IPO as longtime CEO of Constant Contact. She took the helm in 1999—long before “SaaS” was a buzzword—with a simple but ambitious mission: help small businesses stay connected to their customers. Over the next 17 years, she led the company from pre-product and pre-revenue to an IPO and ultimately a $1.1 billion acquisition, proving you could build a billion-dollar software business by patiently, profitably serving customers most of the industry ignored. Under Gail’s leadership, Constant Contact grew to hundreds of thousands of customers worldwide and helped normalize ideas now taken for granted: customer-first design, human-assisted onboarding, and a disciplined, data-driven approach to growth. Since stepping down in 2016, Gail has continued shaping the next generation of entrepreneurs as a board member at Shopify, Mindbody, Jobber, and ShipBob, as a mentor with MassChallenge and Techstars, and through nonprofit work at EforAll.

The latest edition of Outsider Inc. features Isaac Saldana, co-founder and former CEO of SendGrid—the leading cloud-based email delivery platform. Founded in Southern California in 2008 and more formally launched out of Techstars Boulder in 2009, SendGrid grew into one of Colorado’s great startup success stories, going public in 2017 before ultimately being acquired by Twilio for $2 billion in 2019. But Isaac’s path to that moment was anything but conventional. Born in the U.S. and raised in Mexico, he returned to California at age 14 without knowing English. By 19, he was married with kids, working two jobs, and putting himself through college full-time to study computer science. After his exit from SendGrid, Isaac has continued to build. He co-founded Joy Labs, a product studio, and recently launched Laneful—an AI-powered messaging platform that reinvents how email and communication infrastructure work at scale. Tune in now for this incredible episode ⬇️

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Episode Highlights

Below are a few highlights from my interview with Isaac. In this first clip, he shares a moment of humility—as a non-native English speaker, he welcomed his board’s small language corrections as evidence that they genuinely wanted to see him grow and succeed. When a founder invites that kind of coaching, precision in words becomes precision in judgment; it builds the type of foundational trust that opens the door to clear start/stop/continue guidance when it matters most.

In this next clip, Isaac recalls ringing the NYSE bell as a ritual that made the dream tangible. Looking down at teammates who’d stuck with him through the journey of building the company, he saw their belief crystallize into something real. The IPO mattered less to him as a market milestone and more as a collective affirmation of endurance—proof that showing up, together, turns vision into reality.

And here, Isaac shares his view that humility and confidence are a flywheel—you signal competence, then openly admit what you don’t know, run experiments, and even conclude something isn’t doable, which paradoxically builds more confidence. Great leaders hold conviction on the goal and humility on the path, turning learning into momentum

Finally, Isaac shares one of his hardest shifts: from an introverted engineer who was still learning English and working alone at home to the cofounder who had to learn to sell. He literally practiced ‘deliverability’ in the mirror for a month, then—three months after launch, with two kids and rent due—learned to sell because he had no choice.

I really enjoyed this conversation with Isaac and am grateful to him for sharing his hard-earned wisdom. What stayed with me wasn’t the IPO so much as the growth that made it possible: a non-native English speaker practicing ‘deliverability’ in the mirror; an introvert learning to sell with his back against the wall; and a founder willing to step aside to welcome a new CEO when the company needed it. A relentless focus on culture got him there—you can see it in that New York Stock Exchange moment, looking down at teammates who’d believed from the beginning. Above all, Isaac reminds us that values aren’t wall art—they’re operating instructions. Confidence and humility belong side by side, and sometimes your most important co-founder is at home, keeping you grounded for the long game.

The Five Dysfunctions of a Team

In the episode, Isaac shared his appreciation for the management writer and thinker Patrick Lencioni’s The Five Dysfunctions of a Team. This classic is a leadership fable about a struggling tech company, DecisionTech, and its new CEO, Kathryn Petersen.

Through her turnaround, Lencioni lays out a pyramid of interlocking failure points: absence of trust (teams won’t admit mistakes or weaknesses), which breeds fear of conflict (no vigorous debate), leading to lack of commitment (ambiguous decisions), avoidance of accountability (peers won’t call each other out), and finally inattention to results (status or silos trump collective outcomes). The core thesis is simple and hard: sustainable performance begins with vulnerability-based trust and cascades upward.

Lencioni pairs the model with practical application: personal-history and strengths exercises to normalize vulnerability; mining for conflict to surface the real debate; explicit decision capture and cascading messages to secure buy-in; public goals and peer-to-peer accountability to keep promises real; and a visible scoreboard plus team-based rewards to anchor attention on shared results. It’s intentionally prescriptive and a bit reductive, but that’s the point—leaders get a crisp diagnostic and playbook.

The book’s enduring value is giving operators a common language for diagnosing why a talented group is underperforming. It also echoed in my conversation with Isaac: his willingness to invite correction signaled vulnerability-based trust; that trust enabled healthy conflict, clearer commitments, and the peer accountability he described as start/stop/continue guidance. Humility set the foundation, and the results were the outcome of a team putting the pyramid into practice.

Up Next

Tune in next week with Kyle Porter, the founder and longtime CEO of SalesLoft, the Atlanta based company that pioneered sales engagement as a software category. Under Kyle’s leadership, SalesLoft scaled to unicorn status in 2021 and ultimately reached a $2.3 billion valuation the next year with a majority investment from Vista Equity Partners. Along the way, SalesLoft became one of Atlanta’s most celebrated startups, known as much for its culture and values as for its technology and business success. But Kyle’s story isn’t just about building a multi-billion dollar company. It’s also about resilience: from overcoming childhood health challenges to a life changing turning point in college to balancing the intensity of hyper growth with family life. Hear how Kyle turned setbacks into defining moments, what it means to lead with love as a CEO, and how he sees the future of Atlanta’s thriving tech ecosystem.

The latest edition of Outsider Inc. features Aaron Slodov—founder, engineer, and a leading voice in America’s industrial revival. As founder and CEO of Atomic Industries, Aaron is rebuilding the ancient craft of tool-and-die with software and generative AI from the heart of the Midwest. Aaron’s path runs from soldering circuits as a kid in Cleveland, to earning a physics degree while working full-time, starting his career as part of Google‘s self-driving effort, and co-founding Remesh, where he saw both tech’s promise and its potential pitfalls. After a tough exit and a stalled hardware attempt, Aaron hit America’s broken manufacturing system—launching Atomic to turn tribal knowledge into scalable infrastructure. Along the way, he also co-founded the Reindustrialize Summit and the New American Industrial Alliance. In the episode, we discuss overcoming short-termism and why rebuilding heavy industry is the defining project of our time. Tune in below.

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Episode Highlights

Below are a few highlights from my interview with Aaron. In this clip, he argues for building like an anthropologist: stay pragmatic, root decisions in real human behavior, and keep things grounded in reality. He urges leaders to ditch rote playbooks, and instead, design the company, product, or event they’d genuinely want themselves:

In this next clip, Aaron frames the founder journey as exhilarating but bruising, and says the antidote is a strong peer support system. He provides a practical tip: urging founders to start small group chats with other founders to grow together, swap advice, and say the things you can’t say publicly:

And here, Aaron argues that armchair views of manufacturing collapse the moment you watch a CAD file become G-code and a block of metal get machined—without firsthand exposure, you miss the system’s real constraints. He says the costly reps of the physical world have left a huge old-vs-new knowledge gap. Legacy players hold critical tacit know-how that isn’t transferring to the next generation, which is both the problem and the opportunity:

Finally, Aaron calls out American complacency about cheap goods, arguing that globalization’s comparative advantage often masked exploitation of people in far-off places. He says accepting brutal labor conditions so we can buy low-cost products isn’t progress—it’s a moral failure:

I really enjoyed this conversation with Aaron and am grateful to him for sharing his candid, hard-won story. Curiosity took him from Cleveland to Google X, and the scars from Remesh sharpened his views on control, incentives, and building for the long term. Instead of retreating, he ran at our broken manufacturing system—all while convening builders through the Reindustrialize Summit and the New American Industrial Alliance. What stuck with me most is Aaron’s posture: choose the uphill problem, respect the craft, and align stakeholders for the long game. If we want resilient supply chains and a stronger middle class, that’s the mindset it takes.

Kochland

In the episode, Aaron shared his admiration for Kochland: The Secret History of Koch Industries and Corporate Power in America, by investigative journalist Christopher Leonard. I was not aware of this book before, but I’m glad Aaron mentioned it—once I began reading it, I couldn’t put it down. It’s a non-fiction that reads like a drama novel.

Kochland is a sweeping history of Koch Industries and the rise of Charles Koch’s private empire from a Midwestern refinery into one of the largest, most influential companies in America. Told through episodes—a crude oil syphoning scandal on Indian lands, labor showdowns at the Pine Bend refinery, high-stakes energy trading, and serial acquisitions like Georgia-Pacific—the book argues that Koch’s distinctive operating philosophy, plus the advantages of being private, created an organization optimized to exploit market inefficiencies, regulatory shifts, and commodity cycles.

Koch’s approach to management translated into everyday behaviors: building world-class trading and risk systems, mastering vertical integration in energy and chemicals, and institutionalizing extreme cost discipline. Koch’s edge came from information and optionality: measuring flows better than rivals, arbitraging complex rules, and moving faster because they didn’t have to manage quarterly optics. The narrative makes clear that, structurally, Koch behaves more like a sophisticated capital allocator and control-systems company than a conventional industrial firm.

Kochland is also a critique of concentrated private power, cataloging the company’s numerous environmental violations, anti-union tactics, and relentless regulatory warfare. It links Koch’s business strategy to a parallel political apparatus that shapes tax, climate, and regulatory policy. Together, operating prowess and political influence form a reinforcing loop—applying market-reading skills to the rules themselves and raising hard questions about accountability inside an opaque, privately held empire.

For operators and investors, the book is a double-edged playbook. On the positive, long-termism, cash compounding, deep process control, and culturally encoded decision rights can produce durable advantage. As a caution, systems that maximize efficiency and control can externalize costs, erode trust, and invite backlash when the stakes are high. If nothing else, Kochland is a gripping and entertaining read.

Up Next

Tune in next week with Isaac Saldana, co-founder and former CEO of SendGrid—a cloud-based email platform that delivers transactional and marketing emails reliably and at scale. Founded in 2008, SendGrid grew into one of Colorado’s great startup success stories, going public in 2017, before ultimately selling to Twilio in a $2 billion acquisition in 2019. But Isaac’s path to that moment was anything but conventional. Born in the U.S. and raised in Mexico, he returned to California at 14 without knowing English. By age 19, he was married with kids, working two jobs, and putting himself through college full-time. After his exit from SendGrid, Isaac has continued to build. He co-founded Joy Labs, a product studio, and recently launched Laneful—an AI-powered messaging platform designed to reinvent how email and communication infrastructure work at scale. Tune in next week for this incredible episode.

The latest edition of Outsider Inc. features Guillaume de Zwirek, the founder and CEO of Artera—a platform that helps patients navigate their care while reducing staff burden by unifying communication across text, email, phone, and chat. Since 2015, Artera has grown into a leader in patient communication, used by nearly 1,000 health systems to facilitate over 3 billion patient interactions per year. But Gui’s path was anything but conventional. He trained as a classical guitarist, competed as a world-class Ironman triathlete, and a health scare during one race pulled him into the healthcare system as a patient—sparking the idea for Artera. Gui’s journey is a masterclass in conviction with consequences. He’s shown the resilience to keep going and the discipline to choose partners over price, grit over optics, and action over theatrics. Tune in now to hear how Gui turned personal frustration into a category-defining company, why Santa Barbara became the unlikely home of a digital health breakout, and where he sees the future of health tech heading in the age of AI.

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The Ride of a Lifetime

In the episode, Gui shared his admiration for Bob Iger’s bestselling book, The Ride of a Lifetime, a memoir-playbook that traces his path from a young ABC staffer to CEO of Disney. The book’s narrative revolves around three priorities he pitched on day one—invest in high-quality branded content, embrace technology, and expand globally. It then shows how those principles drove key moves: repairing relations with and buying Pixar, acquiring Marvel and Lucasfilm, and laying the groundwork for Disney+, among others. It weaves deal stories with personal vignettes (especially his relationship with Steve Jobs) to illustrate how trust and taste shape corporate strategy.

Iger frames leadership as a handful of habits—optimism, courage, focus, fairness, curiosity, and decency—applied to creative enterprises at scale. The deal stories are instructive not just for price or timing but for structure and autonomy: Pixar kept its culture, Marvel retained decentralized creative control, and Lucasfilm safeguarded canon. Each acquisition plugged Disney’s characters and worlds into a flywheel spanning film and TV, parks, merchandise, and streaming. Iger’s negotiating style is low-ego and relationship-first: reduce surprises, move fast once the logic is clear, and pay up for quality when the strategic upside compounds across platforms.

As analysis, the book’s core value is showing how to convert a simple strategy into irreversible actions: mend a broken partnership (Pixar), buy what you can’t build fast enough (Marvel/Lucasfilm), and use distribution and experiences to amortize creative risk. Founders and CEOs will find portable lessons in board communication (three crisp pillars), crisis response (be visible, decide quickly), and talent stewardship (protect creators so the brand stays scarce and premium).

The limitations are mostly those of CEO memoirs: the lens is success-forward and lighter on misses, and succession is treated more as a cautionary aside than a post-mortem. Still, as a leadership text for creative, brand-driven businesses, it’s unusually concrete: a case study in taste, timing, and trust—and in paying real money for assets that make your strategic pillars non-negotiable.

One Fun Thing

I was able to dig up an interview of Gui on YouTube (of course) from 2013 outside of the Ironman event in Texas. It was fun to see Gui, more than a decade ago, being as methodical about triathlons back then as he is building Artera today:

Episode Highlights

Here are a few highlights from my interview with Gui. In this clip, he describes how founders must grow into bigger problems the way kids grow into adulthood—you can’t rush the maturity. He also reflects on how being a CEO has changed him— repeated hard calls built the scar tissue to handle today’s crises, even as it’s made him a bit less empathetic than he once was:

In this next clip, Gui describes the survival-mode hustle of early sales—cold-calling hospitals, hacking his way to the right buyer by name-dropping EMR integrations, and even hiring a rep who slept in the office—until one working pilot lit the fuse. It wasn’t a playbook; it was do-anything-ethical experimentation to create value and get traction:

And here, Gui describes why the remix of “World on Fire” (his favorite reggae song) is his entrepreneurial anthem—the audacious “who set the world on fire? it was me” chorus captures a burn-the-ships mindset. For him, it’s about owning the outcome, risking comfort, and lighting a path forward:

Finally, Gui talks about the origin of Artera, in particular how a sudden health scare forced him to stop training and bounce between specialists, exposing the 8–5, phone-first dysfunction of healthcare customer service. That lived frustration—and the conviction no one was solving it well—became the spark to start the company:

I really enjoyed this conversation with Gui and appreciate his willingness to share his fascinating perspectives and experiences. His journey is a master class in conviction with consequences. First burn the ships, then do the work. From collapsing mid race and getting back up, to building Artera outside The Valley, he’s shown the resilience to keep going and the discipline to choose partners over price, grit over optics and action over theatrics. What strikes me most is his evolution. Trust first, verify fast, make the call, and use scar tissue as a tool, not a shield. If his AI native vision lands concierge level care at Medicaid cost, we’ll look back and call this messy middle the moment it all clicked and changed the game for the better.

Up Next

Tune in next week with Aaron Slodov—founder, engineer, and a leading voice in America’s industrial revival. As founder and CEO of Atomic Industries, he’s rebuilding the ancient craft of tool-and-die with software and generative AI from the heart of the Midwest—training models on-site with a custom supercomputer to make producing physical goods as scalable as code. Aaron’s path runs from soldering circuits as a kid in Cleveland, to earning a physics degree while working full-time, starting his career as part of Google’s self-driving effort, and co-founding Remesh, where he saw both tech’s promise and its misaligned incentives. After a tough exit and a stalled hardware attempt, he hit America’s broken manufacturing system—launching Atomic to turn tribal knowledge into scalable infrastructure. He also founded the Reindustrialize Summit and the New American Industrial Alliance. In the episode, we’ll talk about beating short-termism, and why rebuilding industry is the defining project of our time.

The latest edition of Outsider Inc. features Jon Lensing, the co-founder and CEO of OpenLoop, a telehealth infrastructure platform headquartered in Des Moines, Iowa. Since its humble beginnings in 2020, OpenLoop has scaled to serve more than 2 million patients annually with 16,000 clinicians across all 50 states. The company has raised over $120 million in funding and was recently valued at over $1 billion. Jon’s path to becoming a tech founder was anything but typical. After growing up in a small town in rural Iowa, he trained as a physician and was on track for a career in surgery before deciding to forgo residency and instead build a tech company. From recruiting doctors out of a grocery store café to navigating a pandemic pivot that completely reshaped the business, Jon’s story is a powerful example of the perseverance and resilience required to build big outside the traditional tech hubs and founder profiles. Tune in now for this incredible episode ⤵️.

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I enjoyed this conversation with Jon and appreciate his willingness to share his unique experience and perspectives. Jon reminds us that constraints create diamonds, that great co founders are complimentary, not carbon copies, and that the best decisions often come as much from instinct as data. And there's a quieter lesson too. Success in outsider places doesn't come with fanfare. It's earned in the spaces between big moments. Dollars when the term sheet falls through, when payroll is tight, or when you decide to pivot before the market validates you. Jon's story is proof that staying the course in the face of steep odds can pay off big.

Episode Highlights

Here are a few clips from the interview with Jon. In this first video, he talks about how the capital constraints OpenLoop has faced throughout their journey has shaped the company’s culture, and ultimately, made the company stronger:

Next, Jon describes the importance of success stories to inspiring future generations in less active ecosystems, and his hope that the success of OpenLoop will play that role in Iowa:

And here, Jon talks about the biggest advantage of being based in Iowa despite the many challenges that go along with it—being close to customers. He also shares the bigger mission that he and his co-founder Christian are on, which is to put Iowa on the map for tech talent:

Finally, Jon talks about the importance of being able to make the tough decisions in the face of a lack of data, and how to take a methodological approach to filtering the choices to be more strategic about opportunities:

Up Next

Tune in next week with Guillaume de Zwirek, founder and CEO of Artera, a platform that helps patients navigate their care while reducing staff burden by unifying communication across text, email, phone, and chat. Since 2015, Artera has grown into a leader in patient communication, used by nearly 1,000 health systems and federal agencies to power 3 billion patient interactions a year. Gui’s path was anything but conventional. He trained as a classical guitarist, competed as a world-class Ironman triathlete, and a health scare during one race pulled him into the healthcare system as a patient—sparking the idea for Artera. Along the way, he built his career at Google and data platform Graphiq, gaining a front-row view of how technology can scale products and transform industries. Tune in next week to hear how Gui turned personal frustration into a category-defining company, why Santa Barbara became the unlikely home of a digital health breakout, and where he sees the future health tech heading.

The latest edition of Outsider Inc. features Jimena Pardo, one of the few people in Latin American tech who’s built from every seat—startup founder, big tech operator, and venture capitalist. Jimena became a pioneer in Mexico's startup movement in 2012 when she co-founded the car-sharing platform Carrot, leading the company through six years of growth and navigating numerous challenges before selling the business. After Carrot, she made a major shift—moving to Silicon Valley and joining Facebook, now Meta, to lead product growth for Spanish-speaking Latin America. After four years in Silicon Valley, she returned home to Mexico in 2022—launching Hi Ventures alongside her longtime friend and mentor Federico Antoni. As co-founder and managing partner at Hi, Jimena backs globally ambitious early-stage companies, with a sharp thesis centered on AI and local data. Her journey is a reminder that great ecosystems are built by people willing to take risks, help others, and open doors for the next generation. Tune in now ⤵️.

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Mexico’s Tech Ecosystem

In 2012, when Jimena launched Carrot, Mexico’s tech startup ecosystem was just getting started. Since then, the ecosystem has grown significantly. To visualize this, I plotted the annual number of venture deals in the country since 2010:

In 2010, there were about a dozen Seed deals—prior to then, there were none—which grew significantly to around 80 by 2012, along with the broader Seed/startup boom accelerating worldwide. Since then, activity continued to grow, and in the last decade, Mexican companies have raised around 20-25 deals per month—or about one deal per business day—outside of the historic boom that took place in 2021 and 2022. Things have settled down since then, but it’s been a reversion to the pre-boom level, rather than a shift downward to a lower rate of startup activity moving forward.

To place this growth in context, the chart here shows Mexico’s venture deals relative to three larger groups—Latin America as a whole (including Mexico), the world as a whole (also includes Mexico), and for good measure, relative to the United States (does not include Mexico). The data provide a few interesting insights.

To begin, Mexico’s share of global startup activity is small (0.3% worldwide) but has remained relatively steady for more than a decade, demonstrating its growth and resiliency through the various cycles the last decade and a half—a time when annual venture deals worldwide have grown more than 200%.

Second, Mexico’s pace of venture deal activity is growing faster than is deal activity for the United States. Mexico’s deal activity a decade and a half ago was equal to about 0.5% of the US level, but that number has doubled by 2024. The growth in that number has also been consistent—as evidenced by the steady upward-sloping purple line—which means that Mexico’s growth relative to the US has been durable (albeit, from a much smaller base).

Finally, at 13%, Mexico’s share of venture deal activity across Latin America is the second highest behind Brazil (41%), and just ahead of Chile (which rounds up to 13% of the region). However, Mexico’s share of deal activity in the region reached as high as 25% in 2016, and has declined ever since—occurring at a time when its absolute number of deals grew significantly. What explains this apparent discrepancy? Brazil—it is large and fast growing—accounting for more than 50% of the region’s growth in venture deal activity over the period. In short, Mexico grew, by a lot, but Brazil grew even more—and it was already so much bigger to begin with. With Brazil, Mexico was responsible for 12% of the regions change in activity in 2012 versus 2024—the largest source of non-Brazil growth in the region. Without Brazil, that number jumps to 23%.

One Fun Thing

I was able to dig up some early promotional footage of Carrot on YouTube (of course). In this video—one of many I could find—from July 2013, Jimena provides viewers with a demonstration of how Carrot works. It reminds me of my days using Zipcar in San Francisco (where I lived at the time) and other cities I visited around the US. It was fun to see Jimena, more than a decade ago, sharing the early vision for more efficient transportation within Mexico City (Spanish language):

Episode Highlights

Here are a few clips from the interview with Jimena. In this first video, she talks about the importance of helping founders who are overlooked—particularly the outsiders who are aspiring for greatness, but who don’t look the part or fit the typical mold:

Next, Jimena reminds us that the best global fintech company is from Latin America (Nubank), and shares her vision for the region to produce the next great global tech companies across other categories as well—health tech, e-commerce, real estate tech, and so on. She hopes that every founder in Latin America can build their companies as if they were in the US, and that capital and other barriers faced by founders in the region will be removed.

And here, Jimena reflects on her time at Facebook (now Meta) as being restorative after experiencing burnout as a startup founder—physically, emotionally, economically—even referring to it as her “startup rehab.” But, over time, the entrepreneurial itch became hard to ignore—which is something that many founders who follow a similar path will face and need to overcome.

Finally, after returning home to Mexico City from Silicon Valley, Jimena also returned to her business home—the venture firm that seeded her journey as a founder, then ALLVP, now Hi Ventures. In this clip, Jimena recalls her mental journey evolving from founder and operator to investor, and the role that community played in her decision to make that evolution:

I enjoyed this conversation with Jimena and appreciate her willingness to share her wisdom and journey—one defined by exploration, ambition, and constant reinvention across every seat in the startup world. What struck me most is her humility and ability to stay grounded in who she is. I left the conversation inspired by her conviction that Latin America can build not just regional champions, but global tech giants. I look forward to following her journey—and the region’s—in the years ahead.

Up Next

Tune in next week when we’re joined by Jon Lensing—the co-founder and CEO of OpenLoop, a telehealth infrastructure platform headquartered in Des Moines, Iowa. Since its humble beginnings in 2020, OpenLoop has scaled to serve more than 2 million patients annually with 16,000 clinicians across all 50 states. The company has raised over $120 million in funding and was recently valued at over $1 billion—the first company in the state’s history to reach that milestone. Jon’s path to becoming a tech founder was anything but typical. After growing up in a small town in rural Iowa, he trained as a physician and seemed headed for a career in surgery before deciding to forgo residency and build a tech company instead. From recruiting doctors out of a grocery store café to navigating a major pandemic pivot that completely reshaped the business, Jon’s story is a powerful example of the perseverance and resilience required to build big outside the traditional tech hubs and founder backgrounds. Tune in next week for this incredible episode.

The latest edition of Outsider Inc. featured Melodie van der Baan—retail entrepreneur, tech founder, and CEO of Max Retail, a platform helping thousands of independent retailers efficiently turn unsold inventory into new revenue. Melodie's path defies the usual script. She skipped college to dive into real estate as a teen, then crisscrossed the country in a Sprinter van selling designer apparel to boutiques. She later opened her own retail shop in South Florida, where the sting of unsold inventory sparked the idea for Max Retail. Melodie launched the company while raising two young children during the COVID-19 pandemic, before completing Techstars LA, raising $20 million in venture funding, and now, scaling the platform to serve over 2,000 retailers across all 50 US states. Melodie’s story is one of perseverance, customer obsession, and building from lived experience. We discuss betting on yourself, breaking into tech on your own terms, and never taking no for an answer. Tune in now ⤵️.

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Healthy Habits

In the episode, Melodie mentioned two books that have been influential to her. In the first, Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones, author James Clear argues that tiny, consistent improvements can compound into big results. Two big ideas anchor the book: identity and compounding.

Instead of chasing goals, build systems—routines and environments that make progress automatic. Habits follow a feedback loop (cue → craving → response → reward), so changing the loop changes behavior.

Clear’s posits four laws of behavior change:

1. Make it obvious (design cues; use implementation intentions and habit stacking);

2. Make it attractive (bundle with something you enjoy; leverage social norms);

3. Make it easy (reduce friction; the two-minute rule; automate); and

4. Make it satisfying (track, celebrate quick wins).

To break bad habits, you invert the laws.

In the second book Melodie recommended, Win the Day: 7 Daily Habits to Help You Stress Less & Accomplish More, author Mark Batterson argues that the path to less stress and greater accomplishment is won in 24-hour increments. Rather than obsessing over distant goals, Batterson urges you to narrow the horizon to today, to stack small wins, and to reframe setbacks so they become fuel. Master the day, repeat, and momentum compounds.

He organizes the playbook into seven daily habits:

1. Flip the Script (rewrite the story you’re telling yourself);

2. Kiss the Wave (embrace adversity instead of avoiding it);

3. Eat the Frog (tackle the hardest task first);

4. Fly the Kite (start small and build);

5. Cut the Rope (take wise risks);

6. Wind the Clock (steward time with presence and priorities); and

7. Seed the Clouds (act with expectancy—plant actions today that produce tomorrow’s outcomes).

The throughline is practical hope: tiny, repeatable behaviors beat grand intentions. By shrinking the change to what you can control now, ritualizing mornings and evenings, and letting adversity sharpen focus, you reduce anxiety and create compounding progress—one ordinary day at a time.

Episode Highlights

Here are a few clips from the interview with Melodie. In this first video, she shares how important obsession with the problem—not just a desire to build a company or raise capital—is for founders who need to put it all on the line to go out and solve it:

Next, Melodie talks about the experience of getting accepted into Techstars, and how her perseverance—a refusal to take no for an answer—was essential to turning doubt into reality. This is key: Melodie credits Techstars with paving the road to her success as a founder and for the success of the company in making it to the next stages.

And here, Melodie talks about striking the balance between staying the course in what you believe is the right answer—even in the face of resistance—with staying flexible to change when the market signals a new approach is needed:

Finally, Melodie shares her hope that her failures—not just her successes—inspire and educate other founders in their pursuit of the improbable:

I really enjoyed this conversation with Melodie. Her story is built on lived experience, bold choices, and a refusal to be defined by limits. What stands out to me most is how she’s succeeded by betting on herself, solving real problems, and thinking from first principles. Her advice—to know who you are beyond your business, protect your focus, and be radically transparent—is a powerful counter to today’s cultural obsession with highlight reels. Melodie reminds us that the messy middle, the hard days, and even the failures can be what shape us most. Being an outsider isn’t a setback—it’s an edge, if you’re willing to work, live your values, and keep showing up.

Up Next

Tune in next week when we’re joined by Jimena Pardo—tech founder, operator, and investor helping shape the future of Latin America’s tech ecosystem. In 2012, Jimena co-founded Carrot, Mexico’s first car-sharing company and a pioneer of the country’s modern tech movement. She led Carrot for six years before stepping down and selling the company. Jimena then moved to Silicon Valley to join Facebook (Meta), where she led product growth for Spanish-speaking Latin America. Four years later she returned home to the firm that once wrote both her—and its—first check. As co-founder and manager partner of Hi Ventures (formerly ALLVP—Mexico’s first institutional venture capital firm), she is backing early-stage, global companies from Latin America with a sharp thesis around AI and local data. Few leaders in the region have built from every seat—founder, big-tech operator, angel investor, and now venture capitalist.

The latest episode of Outsider Inc. featured Jewel Burks Solomon—visionary founder, investor, and community leader. She was the founder and CEO of Partpic, a startup that enabled users to identify and replace industrial parts using a photo. After raising venture capital, Jewel later sold the company to Amazon, where her technology was leveraged to reach millions of users worldwide. After Amazon, Jewel led Google for Startups in the United States, where, among other things, she launched the Black and Latino Founders Funds, deploying more than $45 million in non-dilutive capital to underrepresented founders. Now, she's building Collab Capital, a venture fund rooted in Atlanta and built on a different model—one that centers trust, ownership, and long-term wealth creation in underserved communities. This is an incredible episode that you won’t want to miss. Tune in now ⤵️.

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Atlanta’s Tech Ecosystem

After the episode’s release, I became curious about the growth and evolution of the Atlanta tech ecosystem, so I took a look at the data. Below is the annual number of venture deals—an accessible but somewhat narrow proxy for tech startup activity—in the Atlanta metropolitan area between 2006-2024 (green bars) and the region’s share of the US total of such deals (blue lines—actual and smoothed).

At around 2% of total US venture activity, Atlanta it is one of the largest ecosystems in the country outside the Tier 1 regions (San Francisco Bay Area, New York, Boston, Los Angeles). Funding rounds in Atlanta have grown substantially in the last two decades—along with, and about the same pace as, the country as a whole. Atlanta’s share has held more or less steady for nearly two decades—signifying its establishment as one of the leading tech ecosystems nationwide.

Moreover, there have been a number of large tech exits in recent years. According to an analysis of PitchBook data, Atlanta has produced 35 venture-backed exits of $100 million or more since 2006—five of those have been over $1 billion. Another 28 tech companies that did not raise venture capital exited for over $1 billion. Here are a few highlights of major exits in Atlanta in recent years:

• MailChimp: an email marketing platform for individuals and small businesses, that fully bootstrapped to a $12B acquisition by Intuit in 2021.

• GreenSky: a lending platform for small businesses that IPO’d in 2018 before later being acquired by Goldman Sachs in 2022 for $2.2B.

• SalesLoft: an enterprise revenue orchestration platform that raised $200M+ in venture capital before being acquired by Mubadala and Vista for $2.3B in 2021.

One Fun Thing

In the early days of building Partpic, Jewel was quite active in pitch competitions, accelerator programs, and generally hustling across the country to tell the story of Partpic wherever she could. One particular highlight was the Techcrunch Disrupt SF conference in 2014, where Partpic won the “Enterprise Disruptor Award” amongst a group of impressive competition. I managed to track down a video of Jewel pitching the company at the conference more than a decade ago:

Episode Highlights

Here are a few clips from the interview with Jewel. In this first video, she describes her desire to close the gap between the realities that founders are living and what some investors perceive to be true. This mission is driven by her own experience as a founder, when investors she was pitching didn’t believe the tangible milestones the company achieved were actually true:

And here, she conveys her view that superior investment returns can be generated by focusing on spaces and founders that are receiving less attention from the investment community, and then bolstering outcomes through a support-led model at Collab:

I really enjoyed this conversation with Jewel. Her story is a reminder that resilience isn’t just about pushing through—it’s about staying grounded in what matters most. Throughout her journey, Jewel stayed rooted in her values, stood firm in the face of doubt, and kept community at the center the whole way through. What stuck with me most is how she leads—with heart, with integrity, and with a vision bigger than herself. She’s not just making space for the next generation of founders—she’s showing them what it looks like to lead on your own terms.

Up Next

Next week, we’re joined by Melodie van der Baan—retail entrepreneur, tech founder, and CEO of Max Retail, a platform helping thousands of independent retailers turn unsold inventory into new revenue. Melodie’s path is anything but typical: she skipped college to start in real estate as a teen, crisscrossed the country in a Sprinter van selling designer apparel to boutiques, and later opened her own retail shop in South Florida, where the sting of unsold inventory sparked the idea for Max Retail. After Techstars LA and raising $20 million in venture funding, she’s scaled the platform to serve 2,000+ retailers across all 50 states. Melodie’s story is one of perseverance, customer obsession, and building from lived experience. We’ll talk about betting on yourself, breaking into tech on your own terms, and never taking no for an answer. Tune in next week.

The latest edition of Outsider Inc. featured Sean O’Sullivan—digital mapping pioneer, deep tech investor, humanitarian, and one of the most relentlessly original minds in tech and venture. Sean co-founded MapInfo with three college friends in upstate New York and took the company public at the age of 28. He later coined the term “cloud computing” before taking the mother of all left turns—procuring a bulletproof vest, forging press credentials, and sneaking into Iraq as a freelance war journalist. What began with the intention to film a documentary, Sean ended up launching JumpStart International, a humanitarian organization that cleared rubble and rebuilt destroyed buildings. Back in the States, after making early bets on companies like Apple, Netflix, and Harmonix, Sean launched SOSV, which is now the world's most active deep tech investor. From humble beginnings to mapping the world and investing in the future, Sean's story moves through invention, conflict, and capital. Tune in now ⤵️.

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SOSV's Global Reach

SOSV was officially born in the mid-1990s to facilitate Sean’s investing activities, but evolved since the late 2000’s into what it is today—a multi‑stage venture capital firm that provides founders with pre‑seed and seed capital alongside intensive company building programs (e.g., HAX for hard tech, IndieBio for life sciences) to accelerate deep‑tech startups focused on human and planetary health.

The firm claims to be the world’s most active investor in deep tech startups and its reach is truly global. The chart below shows the country of origin for the SOSV portfolio since 2010 (according to the venture capital database, PitchBook).

Janet Speaks French

During the episode, we touched on Sean’s two-year stint as the singer/songwriter of a band called Janet Speaks French, following his departure from MapInfo in 1992. The band released two albums, Ne me Parlez pas d'Amour and The Planet Janet, selling about 8,000 copies, and reaching an audience of more than 280 radio stations across the United States. Although the band never broke through, at one point they did reach #5 in Detroit radio and #1 in New Hampshire for a weekend.

Sean stated in the episode that he didn’t think any Janet Speaks French tracks could be found online, however, I was able to find this 30 second demo on YouTube. I can only guess, but that must be Sean on the vocals.

Episode Highlights

Here are some highlights from the interview with Sean. In this first clip, he talks about his experience at MapInfo in creating an entirely new category of product.

And here, he talks about the importance for founders to separate the success or failure of the business from the individual—that aligning personal self-worth around the success or failure of a company can be dangerous:

I really enjoyed this uniquely deep conversation with Sean. His journey is a testament to the remarkable ability of people to reinvent themselves through purpose. Further, Sean demonstrates that purpose is not something you find; it's something you build, often in the aftermath of failure, tragedy, or deep reflection.

Up Next

Tune in next week when we’re joined by Jewel Burks Solomon—a visionary founder, investor, and community builder whose journey defies convention. After co-founding Partpic—a breakthrough visual search tool for industrial parts inspired by her firsthand frustrations—she became one of a small number of Black women to lead a venture-backed startup to successful acquisition when Amazon bought the company and integrated its technology. Jewel later led Google for Startups in the US where she helped distribute $45 million in non-dilutive capital to underrepresented founders. Now, she’s leading Collab Capital, a venture capital firm she co-founded to create long-term wealth in underserved communities. In this episode, Jewel opens up about the highs and lows of startup life, reclaiming identity after an exit, designing systems rooted in trust, ownership, and purpose, and why she’s excited to be leading a startup community movement in Atlanta.

Last week’s episode of Outsider Inc. welcomed Shegun Otulana. He’s best known as the creator of TheraNest (now Ensora Health)—a vertical software platform for mental health practices he founded in 2013 in Birmingham, Alabama, and scaled to a $1.2 billion acquisition by KKR in 2021, all after raising a modest $250K in angel capital. Born and raised in Lagos, Nigeria, Shegun arrived in the United States at age 18 with no network, no safety net, and no blueprint. He bootstrapped product launches with personal credit cards, sculpted and scaled a remote workforce, and quietly built one of the most significant tech companies the state has ever seen. Today, he’s backing the next generation of entrepreneurs in the region through Harmony Venture Labs, a venture studio and investment firm, and leading Copysmith, a content platform driven by AI. You won’t want to miss this incredible episode. Tune in now ⤵️.

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Birmingham's Tech Ecosystem

After visiting Shegun and other local leaders last month—headlined by Birmingham’s flagship tech conference, SLOSS Tech—it became clear to me that the region’s tech entrepreneurship ecosystem is thriving. It is still nascent in terms of overall activity, but the connectivity and culture are strong. To quantify one dimension of its maturity, the chart below plots the number of annual venture deals in the Birmingham metro area between 2006 and 2024 (green bars). The dotted blue line indicates the region’s share of total US venture deals each year, while the solid blue line smooths the blue dotted line for volatility (applying a Kalman filter).

While overall venture funding in Birmingham may still be quite limited, the region has generally been growing faster than the rest of the country—tripling its share of US venture deals between 2006 and 2022. The number and share of deals have dipped in the last two years of data, but not enough to reverse the overall trend—yet.

More importantly—particularly for its long-term prospects—the region has already experienced several breakout successes. In addition to TheraNest’s $1.25B exit to KKR, three other breakout tech companies have emerged in Birmingham:

• Shipt—online grocery marketplace founded by Bill Smith in 2014; raised $60M in venture capital funding; sold to Target in 2017 for $550M.

• Fleetio—fleet management software founded by Tony Summerville in 2012; raised more than $600M in venture capital funding; was valued at $1.5B in 2025.

• Landing—corporate accommodations marketplace founded by Bill Smith (yes, the same Bill Smith behind Shipt) in 2019; raised more than $300M in venture capital funding; was valued at nearly $600M at its last round of funding in 2022.

I’ve written before about the criticality of entrepreneurial recycling, or what Endeavor calls the “multiplier effect”, to the development and acceleration of an entrepreneurial ecosystem—whereby the success of breakout companies can stimulate the creation of additional breakout companies when the people, wealth, and wisdom behind those initial successes double down on new efforts. After visiting Birmingham last month, I was happy to see that Bill, Shegun, Tony, and others are quite active in mentoring and investing in upcoming startups—in addition to building new companies themselves. These are signs of a great emerging ecosystem. Keep your eye on Birmingham—it’s early, but all the right things are happening.

The Gift of Global Talent

As an immigrant to the United States, Shegun had me thinking about the long-running benefit that immigrants and immigrant entrepreneurs have brought to this country. No resource better summarizes and articulates this benefit than The Gift of Global Talent: How Migration Shapes Business, Economy & Society, written by Bill Kerr of Harvard Business School, and published in 2018.

In the book, Kerr argues persuasively that the United States has been the unique beneficiary of global talent flows for many decades, but that the US risks squandering its long-held gift of global talent, due to changing economic conditions abroad and a series of missteps at home. As Kerr states at the outset:

I happily admit to being hopelessly confused on many hot button issues. But not on global talent. America’s surge to preeminence over the past 250 years is due to the promise of the “American dream” and the talent it has welcomed to its shores… [but] America has neglected global talent for more than a decade, starting well before the 2016 election… Ceding U.S. talent leadership would hurt Middle America as much as it would harm Manhattan or Silicon Valley.

America’s posture towards global talent has not gotten better since Kerr published those words—they have gotten worse. Much worse.

The book follows four propositions:

1. Talent is the world’s most precious resource

2. Talent as a resource is highly mobile

3. Talent is shaped to a large degree by the environment that surrounds it

4. Global talent flows are important to every country, business, and individual (whether they are aware of it or not).

While most people are generally aware of the US’s unique place in attracting global talent flows, and it receives from them, what may surprise is the sheer magnitude of that dominance. Here are two graphics from the book that make this point.

The table below shows the percentage of three high-skill categories of individuals—Nobel laureates, patent investors, and college graduates—that (i) migrate to another country and (ii) of those that migrate to another country, the percent that migrate to the United States. The third row shows what percentage of those three categories of high-skill individuals located in the United States migrated from another country.

For example, 5% of college degree holders worldwide migrate to another country—but of those that do, a staggering 41% come to the United States. More than 50% of Nobel laureates or patent inventors who migrate internationally choose to come to the United States. That is an astonishing transfer of human capital to one country.

Similarly, immigrants disproportionately drive entrepreneurship in the United States. The chart below shows that immigrants are prominent among entrepreneurs (new business owners). More than 25% of entrepreneurs are immigrants—compared with about 12% of the total population during the same period, meaning that immigrants are twice as likely as the native-born population to start new companies.

This matters to all of us because new businesses are the lifeblood of productivity growth, economic growth, and job creation. Said differently, immigrants, like Shegun and countless others, are critical to national economic prosperity—not just for the people directly involved in those companies, but for all of us.

Episode Highlights

Here are some highlights from the interview with Shegun. In this first clip, he talks about the importance of founders maintaining the “soul” of a company as things scale.

And here, he describes that founder obsession with serving the customer as being more important than unique market insights or experience in the customer’s role:

I really enjoyed this conversation with Shegun. His story is as much about what he built as it is about how he built it—with clarity of purpose and a deep respect for people that shaped every decision. It’s a powerful reminder that building a great company isn’t just about what you do, but who you are.

Up Next

Tune in next week when we’re joined by Sean O’Sullivan, a true original whose career has defied every convention. Sean co-founded MapInfo in the 1980s, putting digital street maps on computers before most people had even used one, and later coined the term “cloud computing” with his startup NetCentric. But his journey took a radical turn when he left tech to enter a war zone in Iraq, eventually founding a humanitarian organization from the rubble. Sean went on to create SOSV, now the world’s most active deep tech venture firm, backing thousands of startups in climate and human health. Along the way, he moved his family and business to Ireland, chairing the country’s national entrepreneurship forum, and staring on Dragon’s Den—Ireland’s version of Shark Tank. This conversation traces Sean’s life through invention, conflict, capital, and an unwavering sense of purpose. It’s an episode you won’t want to miss.

The latest episode of Outsider Inc. welcomed Dug Song, co-founder and former CEO of Duo Security, and a leader in Michigan’s tech ecosystem. Dug founded Duo in Ann Arbor in 2010 with the mission to democratize information security for businesses of all sizes. He quickly scaled the company to more than $100 million in annual recurring revenue, selling it to Cisco in 2018 for $2.35 billion—the largest tech exit in the state’s history at that time. Then, Dug doubled down on Michigan’s innovation ecosystem through investing, philanthropy, and policy advising. The episode traces Dug’s roots from learning to code at age eight in his father’s Baltimore liquor store, to his community-first ethos born out of the punk and skateboard communities, to his involvement in the legendary w00w00 hacker collective, and beyond. This episode was a lot of fun to record. Tune in now ⤵️.

Listen: Spotify, Apple Podcasts, Amazon Music, YouTube

Follow: LinkedIn, Instagram, X, TikTok

The Tao of Wu

In the episode, Dug discussed his affinity for The Tao of Wu, a New York Times bestselling book by The RZA—founder and spiritual architect of the Wu-Tang Clan. Part memoir, part philosophical guide, RZA blends Eastern philosophy, Five-Percent Nation teachings, Christianity, martial arts, and hip-hop to reflect on seven key pillars of wisdom that shaped his evolution from a struggling youth in Staten Island to one of the most influential figures in entertainment. The book offers a personal lens into how he found meaning and discipline through creativity, knowledge, and spiritual practice.

In our conversation, Dug discussed his belief that Duo’s success was attributable to being built in Michigan—that the unique conditions there were foundational and that the company wouldn’t have become what it did anywhere else. RZA makes the same point about the Wu-Tang Clan’s unique brand of success. Despite the fact that Staten Island had no basis in hip-hop, which originated in the Bronx and thrived in Brooklyn, the “Wu-Tang Dynasty” (referring to the group’s collaborative approach that led to a broad sphere of influence) couldn’t have emerged anywhere but Staten Island.

RZA uses the geography and isolation of Staten Island as both a literal and symbolic foundation for Wu-Tang's origin story. Here are three key concepts around this point:

• Isolation as fertile ground: RZA describes Staten Island—nicknamed “Shaolin” by the Clan—not just as a place, but as a kind of creative exile. Being physically and culturally cut off from the rest of New York City gave the Wu-Tang members both freedom and hunger. They weren’t part of the Manhattan industry scene or operating in already-established rap networks in Brooklyn or the Bronx, which forced them to build something of their own.

• A unique mix of influences: Staten Island was a strange brew of working-class struggle, street violence, and spiritual searching. Wu-Tang combined gritty street experience with esoteric teachings, kung-fu cinema, chess, and comic books—all of which were absorbed in part because they were not immersed in a scene that dictated what hip-hop had to be. This separation allowed RZA to develop a philosophy and sound that didn't have to conform to industry expectations.

• Outsider unity: Because they were from Staten Island—and overlooked even within New York—there was a chip on their shoulder, and a powerful bond among them. They weren’t just trying to break into the industry; they were storming the gates together. That collective insurgency became part of the Wu-Tang identity.

In sum, RZA portrays Staten Island as both a constraint and a crucible. It wasn't a coincidence—it was core to the emergence of Wu-Tang Clan. The book makes a strong case that Wu-Tang could only have been born in a place like that—remote, raw, and ready to prove itself. It’s also an approach that aligns with this show’s theme and is aligned with my views on ecosystem-building more broadly.

Ann Arbor’s Small Giant

Dug also referenced how much he learned about building company culture and with community in mind, not from other tech companies, but from Ann Arbor’s famed Zingerman’s Delicatessen. As Dug described Zingerman’s impact on Ann Arbor and his own thinking, I was reminded of an inspiring book I read years ago that profiles the Zingerman’s story—among other high-performing, values-minded, local companies.

In Small Giants: Companies That Choose to Be Great Instead of Big, Bo Burlingham profiles Zingerman’s not for explosive growth, but for choosing a different path to greatness. Instead of franchising or chasing outside capital, founders Ari Weinzweig and Paul Saginaw built a “community of businesses” rooted in deep values, employee ownership, and obsessive customer experience. Their refusal to conform to typical growth playbooks made Zingerman’s a model for entrepreneurial integrity—proving that staying small can be a form of staying true. It’s a quiet rebellion—and it worked.

Small Giants is a study of successful companies that made a conscious choice: to be great instead of big. It’s a collection of companies led by founders who rejected the traditional growth-at-all-costs path in favor of building businesses that reflect their values, serve their communities, and prioritize craft, culture, and purpose. From Clif Bar to Righteous Babe Records to Union Square Hospitality Group to Anchor Brewing, each story challenges the assumption that scale is the ultimate goal.

What makes these companies compelling isn’t their restraint—it’s their intentionality. They’re deeply profitable, often beloved institutions in their communities, and they’ve found ways to thrive without outside capital, high-growth mandates, or compromising their mission. Small Giants shows that success can come from focus—from doubling down on what matters most rather than chasing what matters to others. Even in the hyper-growth world of tech startups, the lessons from these stories are plentiful.

Episode Highlights

Below are some of my favorite moments during the episode with Dug Song. Here, he describes the fulfillment he receives from sharing the fruits of his work for the benefit of others, the joy he experiences from seeing others do well—”Mudita”—and his role as a “steward” for helping to create a new generation of builders.

And second, Dug talks references The Tao of Wu, and the unique factors in a place that can combine in unexpected ways to produce original forms of creativity—tying that back to Duo’s success due to the unique factors in Michigan’s ecosystem.

I was deeply inspired by my conversation with Dug. What stands out to me most is his insistence that building a company should also be an act of public service. Whether it's mentoring founders, shaping policy, or investing in Michigan’s economic future, Dug has stayed relentlessly focused on using entrepreneurship as a tool for inclusion, justice, and long-term value. His legacy won’t just be measured in wealth generated or jobs created, but in the people and ecosystems he’s lifted up along the way.

Up Next

Tune in next week when we’re joined by Shegun Otulana, the founder and former CEO of TheraNest—a vertical software platform for mental health practices he scaled from Birmingham, Alabama to a $1.2 billion acquisition by KKR. Shegun didn’t just build a billion-dollar company—he built it with intention, grit, and humility. He’s now backing the next generation of entrepreneurs through Harmony Venture Labs. Shegun’s story is as much about what he built as it is with how he built it—with clarity of purpose and a deep respect for people that shaped every decision. It’s a powerful reminder that building a great company isn’t just about what you do, but who you are. I look forward to sharing this with our listeners. Tune in next week.

The latest edition of Outsider Inc. welcomed Brad Feld, co-founder of Foundry and Techstars, and a champion of outsiders everywhere. His prolific writing on venture deals, startup communities, and company building made entrepreneurship more accessible, and his openness on mental health, relationships, and leadership helped shape a more human and sustainable vision for entrepreneurial life. His latest book, Give First: The Power of Mentorship, distills the philosophy that has guided his career—that by helping others without knowing what you’ll get in return, we build stronger companies, relationships, and communities. “Give First” is not just a hashtag—it’s a way of operating that has created ripple effects far beyond what any single company or career could achieve. This is a great episode packed full of wisdom from Brad’s decades of experience in the trenches. Tune in now ⤵️.

Listen: Spotify, Apple Podcasts, Amazon Music, YouTube

Follow: LinkedIn, Instagram, X, TikTok

Give First

Brad’s new book, Give First: The Power of Mentorship, is a heartfelt and intellectually grounded guide to mentorship in the entrepreneurial world. Drawing from his decades of experience as a founder and investor, Brad argues persuasively that the key to strong startup communities lies not just in capital or connections, but in mentorship given freely, without an expectation of immediate return, nor with transactional parameters established as a precondition. Brad’s personal storytelling makes the book compelling—moments of failure, renewal, insight, and emotion that vividly illustrate the strength of non-transactional relationships in a highly transactional world.

Using the Techstars “Mentor Manifesto” as a guide, Brad deconstructs key mentoring best practices, including active listening, honesty, separating fact from opinion, and emotional presence. Each is bolstered by anecdotes from Brad’s years of professional experience and his personal reflections. These sections function as a mentorship manual—both accessible and nuanced—for founders, investors, and operators alike.

What sets Give First apart is its emotional depth. Brad reflects not just on success stories, but on burnout, boundaries, and the downsides of over-giving. His openness and vulnerability about success and failure add credibility to a critical message: that how you treat others, especially during hard times, defines your legacy. In a world obsessed with ROI and exits, Brad’s advocacy of giving as its own reward is refreshing.

Give First is a timely and timeless contribution to the canon of startup wisdom. It challenges readers to decouple help from personal gain, thereby fostering a more generous, resilient, and interdependent entrepreneurial culture. Whether you’re a first-time founder or a seasoned investor, this book is a blueprint for leading with empathy, authenticity, and long-term commitment.

The Other Eight

Brad is a prolific writer, not just on his Feld Thoughts blog (which I highly encourage readers to peruse), but with his book writing. Give First is his ninth. Here’s a brief overview of the other eight:

Do More Faster: Techstars Lessons to Accelerate Your Startup (with David Cohen). Based on lessons from Techstars, this book distills startup wisdom into actionable advice across product development, fundraising, team building, and more. It's structured as a series of short, candid essays by mentors and founders.

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist (with Jason Mendelson). A practical guide to understanding how venture capital works. From term sheets to deal structures, Brad and Jason demystify the fundraising process for entrepreneurs and empower them to negotiate with confidence.

Startup Communities: Building an Entrepreneurial Ecosystem in Your City. Brad introduces the "Boulder Thesis" and argues that thriving startup ecosystems must be entrepreneur-led, inclusive, and built with a long-term commitment. He draws from his experience in Boulder to offer a framework that can be adapted to any city.

Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur (with Amy Batchelor). Co-written with Brad’s wife Amy, this book offers an honest look at maintaining a healthy relationship while living the intense life of a startup founder or investor. It offers tools and reflections for balancing love and work.

Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors (with Mahendra Ramsinghani and Matt Blumberg). A comprehensive guide to building and managing effective startup boards. It covers board composition, founder responsibilities, and how to turn a board into a strategic asset rather than a formality.

Startup Opportunities: Know When to Quit Your Day Job (with Sean Wise). A hands-on framework for assessing whether your business idea has real potential, emphasizing early customer feedback and opportunity realism. It helps founders decide when (and if) to take the entrepreneurial plunge.

The Startup Community Way: Evolving an Entrepreneurial Ecosystem (with Ian Hathaway). This follow-up to Startup Communities applies complexity theory to entrepreneurial ecosystems. It shows how communities grow organically through dynamic, interconnected relationships rather than top-down planning.

The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors (with Dave Jilk). Brad and Dave use 52 Nietzsche quotes as launching points for short entrepreneurial essays in five core areas: strategy, culture, free spirits, leadership, and tactics. Each week’s chapter includes modern interpretation plus real-world startup stories.

They’re all really good and cover a wide range of topics that are essential to the entrepreneur’s journey. I of course have my favorite (😉), but several others I’ve really enjoyed are Startup Communities, Startup Life and Nietzsche.

Episode Highlights

Below are some of my favorite moments during the episode. Here, Brad describes the essence of effective mentorship, and critically, what it is not:

And second, Brad comments on the meaning and evolution of “Give First”, which he defines in his new book thusly:

“Give First” means being willing to put energy into a relationship or a system without defining the transactional parameters. However, it’s not altruism. You can and should expect to get something back. But you don’t know when, from whom, in what form, or over what time frame.

I was deeply inspired by our conversation. What stands out most to me is Brad’s willingness to invert the spotlight—to make the work not about himself, but about the people and systems he’s helped shape. Listeners will hear that behind all of Brad's success and impact is a deeply thoughtful and generous human being who takes joy in the success of others.

Up Next

Tune in next week when we’re joined by Dug Song, a cybersecurity visionary who built Duo Security in Ann Arbor, Michigan into a multi-billion-dollar company by taking an unconventional, design-first approach to making security accessible to all. Following a $2.35 billion acquisition by Cisco—then the largest tech exit in Michigan’s history—Dug doubled down on supporting Michigan’s startup ecosystem through investing, philanthropy, and policy advising. In this episode, we trace Dug’s roots from learning to code at age eight in his father’s Baltimore liquor store, to his community-first ethos born out of the punk and skateboard communities, to his involvement in the legendary w00w00 hacker collective, and beyond. You won’t want to miss this episode.