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PODCAST

Fund/Build/Scale

Walter Thompson

After working for years in early-stage startups and as a journalist, here are three hard truths I’ve learned: 1. Success in Silicon Valley hinges on connections, hard work and luck. 2. Startups often fail because founders lack fundamental business knowledge. 3. Real, actionable advice comes from those who’ve actually done it. There’s no such thing as “founder DNA.” If you’re willing to take on risk and invest years of your life in something that has maybe a 10% chance of paying off — less if

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All Episodes

52:37

Don’t Wait for the IPO: How Tech Employees Actually...

Fund/Build/Scale ·

2026/02/20

Startup employees are encouraged to believe in the mission. But IPO timelines now stretch well past a decade — and many never happen at all.In this episode, Ben Black, co-founder and managing director of Akkadian Ventures, explains how tech workers can think more strategically about the equity they’ve helped create. Drawing on more than 750 secondary transactions, Ben walks through how employees can evaluate a company’s liquidity posture before accepting an offer, exercise options intelligently,

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37:20

Turning Utility Into Habit: Beyond Basic Gamification

Fund/Build/Scale ·

2026/02/11

I interviewed Play Ventures General Partner Phylicia Koh to explore what founders outside of gaming can learn from two decades of game design.Play Ventures began as a gaming-focused VC fund. Today, it also invests in what Phylicia calls “playable apps,” consumer products that combine utility with the engagement mechanics of games. That doesn’t mean slapping on points and badges. It means understanding motivation, social dynamics, retention loops, and in-app economies. We talk about: What actually

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55:40

The Day You Raise Money Is the Day You Stop Focusing...

Fund/Build/Scale ·

2026/02/06

In this episode of Fund/Build/Scale, Sentry co-founder David Cramer joins host Walter Thompson for a candid, wide-ranging conversation about what founders actually struggle with — and why so much conventional startup advice falls apart in practice.David shares how he dropped out of high school, taught himself to code, and turned a side project into Sentry, the error-tracking platform now used by millions of developers. From there, the conversation moves into the realities of venture capital,

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31:28

Selling Unproven AI to Skeptical Enterprise Buyers

Fund/Build/Scale ·

2026/02/04

Building an early-stage startup isn’t just about the technology — it’s about earning trust before the proof exists.In this episode of Fund/Build/Scale, I’m joined by Jeff Smith, CEO and co-founder of 2nd Set AI, a startup building generative image and video tools for media, entertainment, and sports organizations. Jeff is a repeat founder navigating a familiar but uncomfortable phase: selling complex, unproven AI into large enterprise organizations that are curious about generative technology — and

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46:36

From Seed to Growth: What African Founders Need to Know

Fund/Build/Scale ·

2026/01/31

As African startups mature, the leap from seed to growth brings a new set of challenges — longer fundraising cycles, institutional expectations, governance, and the realities of scaling across fragmented markets.In this episode of Fund/Build/Scale, I sit down with Ngetha Waithaka, partner at Norrsken22, one of the continent’s leading growth-stage funds. We talk about how investors evaluate African startups as they approach Series A and beyond, how founders can tell whether their business is truly

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50:28

What Investors Actually Look For in the First 18 Months

Fund/Build/Scale ·

2026/01/29

In this episode, I’m joined by Jon Callaghan, co-founder and managing partner at True Ventures, and Julie Bornstein — CEO and co-founder of Daydream, founder of The Yes, and former COO of Stitch Fix — to break down what investors really evaluate in the first 18 months of a company’s life.Drawing from their shared history as investor and founder, we talk candidly about runway, hiring before certainty exists, conviction versus ego, and how trust between founders and investors gets tested when plans

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56:44

Is the Defensible Moat a Myth in AI?

Fund/Build/Scale ·

2026/01/23

For years, founders have been told to build a defensible moat. But in AI, where platforms, models, and capabilities can shift overnight, that advice is starting to feel outdated.In this episode of Fund/Build/Scale, Simular CEO and co-founder Ang Li talks about what it actually means to build a company when the underlying technology won’t sit still. Rather than evangelizing agents or predicting the future of work, Ang gets unusually candid about fragility, speed, judgment, and how founders should

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46:57

Building Against Giants: Turning Insider Expertise...

Fund/Build/Scale ·

2026/01/22

When most founders look at markets dominated by Google or Apple, they see a dead end. Ariel Seidman saw an opening. Before founding Hivemapper, Ariel helped scale Yahoo Maps during a period when search and mapping were rapidly evolving. That experience gave him a front-row seat to how large-scale mapping systems are built — and how technical, capital, and organizational constraints shape the pace of innovation at scale. In this episode, he breaks down what it really takes to build a startup against

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37:46

From Scarcity to Scale: Building Startups in Latin...

Fund/Build/Scale ·

2026/01/21

Odille Sánchez leads the Tech and Scientific-Based Entrepreneurship Center of Excellence at Tecnológico de Monterrey, where she works with hundreds of early-stage founders across Latin America. In this episode, she explains how mindset, methodology, and community are reshaping what it means to launch a startup in a region where early capital is scarce and institutional support is fragmented. We also talk about: Why resource orchestration — not acceleration — is what most founders need How cultural

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54:24

Why Black Startup Founders Have to Play a Different Game

Fund/Build/Scale ·

2026/01/10

When you don’t have generational wealth or a built-in network, the startup path isn’t just harder — it’s different.In this episode, I’m joined by James Norman and Sean Green of Black Operator Ventures for a candid conversation about what early-stage founders actually need to understand to raise capital and scale companies when they’re coming from the outside. We talk about why fundraising is a power-dynamic game, not a meritocracy — and why underrepresented founders have to master the theater of

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51:45

Building an Enterprise AI Startup from Day Zero

Fund/Build/Scale ·

2026/01/07

Lexi Reese has scaled companies at every stage — from building Google’s programmatic advertising business, to helping Gusto grow revenue from $10M to $300M. Now she’s co-founder and CEO of Lanai, an enterprise AI startup tackling a problem most companies don’t even realize they have: they can’t actually see how AI is being used inside their organizations, or whether it’s driving real outcomes. In this episode, we unpack what it really looks like to build a company from scratch in the AI era. Lexi

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48:00

Building in Layers: The Compound Startup Playbook

Fund/Build/Scale ·

2025/12/23

April co-founder and CEO Ben Borodach joins Fund/Build/Scale to break down how he built a compound startup in one of the hardest markets in fintech: U.S. taxes. We talk about why some problems can’t be solved with a simple wedge product, how to sequence engineering, compliance, and distribution, and what it takes to operate inside complexity for years before the market catches up. Ben shares the early customer discovery work, the “science experiments” that shaped April’s product, and the cultural

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53:07

How to Build in a Market That Won’t Let You In

Fund/Build/Scale ·

2025/12/01

In most industries, if you’ve got a solid idea, a few engineers, and a working prototype, you can at least get in the game.Professional sports is not one of those industries. When Jordy Leiser co-founded Jump with Alex Rodriguez and Marc Lore, he wasn’t just building software — he was trying to rebuild the entire fan experience from the ground up, in a business dominated by legacy players like Ticketmaster. Four years later, his company is powering the digital backbone for teams like the Minnesota

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60:46

How to Prove You’re Building a Venture-Scale Company

Fund/Build/Scale ·

2025/11/23

Most founders think VCs want a pitch deck full of market numbers, a roadmap, and a feel-good story about the future.Hoxton Ventures Partner Payton Dobbs isn’t looking for any of that. He wants to know if you actually understand the game you’re trying to play. In this conversation, Payton breaks down the tactical stuff founders almost always get wrong: why TAM slides don’t matter how to define your real market what early signals prove you have a painkiller and not a vitamin and why most technical

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19:50

The "Marionette Threat" of Generative AI with All...

Fund/Build/Scale ·

2025/11/18

Today’s episode is something a little different. I’m doing a feed swap with Humans of AI, a podcast from the team at Writer. What you’re about to hear is their conversation with David Ryan Polgar, the Founder and President of All Tech Is Human, a leading organization in the Responsible Tech movement. He’s a pioneer in tech ethics and responsible innovation, and someone who’s been thinking about the societal impact of AI long before it was mainstream. If you’re building in AI, investing in it, or

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47:19

Cyan Banister & Cristian Cibils Bernardes: Early...

Fund/Build/Scale ·

2025/11/07

Recorded live in San Francisco during TechCrunch Disrupt 2025 week, this Fund/Build/Scale session brings together Cyan Banister (Long Journey Ventures) and Cristian Cibils Bernardes (Autograph) for a practical look at building consumer AI and the investor-founder dynamics that make it work. We dig into pre-traction signals that actually predict momentum, how to validate a weird idea, raise smart money, and ship products people return to. Cristian shares Autograph’s first moment of value, retention

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53:40

From Engineer to CEO: Ryan Wang on Building Assembled...

Fund/Build/Scale ·

2025/10/27

I interviewed Ryan Wang, co-founder and CEO of Assembled, in his San Francisco office to unpack how he turned lessons from Stripe into a fast-growing startup that powers customer support teams at Robinhood, Canva, and Notion.We talk about: Finding the right co-founders and surviving a CEO hand-off Discovering product-market fit by asking one powerful question Turning a “sleepy” support category into a $200 billion opportunity Launching a second product with a startup-within-a-startup

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35:14

The Starting Five: How to Build a Leadership Team...

Fund/Build/Scale ·

2025/10/09

When startups fail to scale, it’s rarely because of bad code or bad luck. More likely, it's because they didn’t hire the right people at the right time.Chris Barbin, founder and CEO of Tercera, shares a playbook for assembling your “Starting Five” — the essential leadership roles every professional services startup needs to grow from $10M to $100M and beyond. Drawing from decades as an operator and investor, he explains how to spot founder-market fit, when to swap out co-founders, and why hiring

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31:16

From Code to Customer: The Strategic Power of a Field...

Fund/Build/Scale ·

2025/10/07

I’ve explored different aspects of product-market fit on the podcast, but when you’re scaling an open-source business with enterprise customers and a global developer community, you also need customer–engineering fit — the ability to translate between what’s being built and what the market actually needs. At Astronomer, Viraj Parekh is that bridge. He is part engineer, part strategist, and part customer advocate, working across product, sales, and engineering. In this episode of Fund/Build/Scale,

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47:35

Dead Weight on the Cap Table: Inside the Ugly World...

Fund/Build/Scale ·

2025/09/20

More startups die from co-founder breakups than from running out of money. Attorney David Siegel, a partner at Grellas Shah LLP, has spent years inside these conflicts, helping founders navigate everything from equity disputes to emotional meltdowns. In this conversation, he explains: Why greed and mismatched expectations trigger so many founder breakups How minority founders can protect themselves before they’re pushed out What departing founders can realistically expect to walk away with Why VCs

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