Fund/Build/Scale

A lot of founders assume raising venture capital is just part of the process: you have an idea, build a deck, find some investors and start pitching. But what if you don't actually need the money yet? Elia Wallen is the founder and CEO of Engine, a business travel platform valued at $2 billion. He bootstrapped his first company and resisted raising outside capital for Engine until the business was...

Most startup fundraising advice focuses on how to get investors interested. Ryan Ziegler sees the process from the other side of the table. As a General Partner at Edison Partners, Ryan evaluates startups that have already survived one of the hardest phases of company building: finding customers willing to pay for what they've built.  By the time founders reach him, the question is no longer wheth...

Conventional wisdom says the hardest part of building a startup is building the product. Shanea Leven says the harder challenge is figuring out what customers will actually pay for. Before co-founding Empromptu.ai, Shanea spent more than 15 years building products at companies including Google, eBay, Docker, and Cloudflare. In this conversation, she explains why sales is every bit as complex as en...

If you're building a startup, there are easier industries to choose than healthcare. Sales cycles are long, regulations are complex, and earning the trust of providers and patients takes years. In this episode, Mayo Clinic Platform Accelerate Director Jamie Sundsbak explains how healthtech founders can improve their odds of success. We discuss what Mayo looks for in founding teams, why the program...

Most startup advice assumes the biggest challenge is finding customers. But what happens when the demand is obvious and the real question is whether the technology can actually work at scale? In this episode of Fund/Build/Scale, I sit down with Stanford professor and Inception Labs founder and CEO Stefano Ermon to discuss how a breakthrough research paper evolved into a venture-backed AI company s...

Most technical founders can explain how their product works. Far fewer can clearly explain why a customer should care. In this episode, Cribl CMO Abby Strong shares what she has learned from building go-to-market teams and helping scale one of the fastest-growing companies in data infrastructure. Drawing on her background in IT operations, product, and marketing, Abby explains why founders often s...

What does it actually mean to build an AI-native company? In this episode of Fund/Build/Scale, I talk with True Ventures Managing Partner Puneet Agarwal and Gather CEO/co-founder Mayank Mehta about how the startup evolved from an AI-powered customer feedback idea into a broader research and content platform for marketing teams. We get into founder conviction before product-market fit, what investo...

For this episode, I interviewed Eugene Malobrodsky, partner at One Way Ventures and former founder of AnchorFree, the company behind HotSpot Shield, one of the first consumer VPN products to scale globally. Before becoming a VC, Eugene spent 15 years building and scaling a startup through the 2008 financial crisis, painful layoffs, difficult fundraising environments, and the long grind from idea t...

A lot of early-stage founders can explain their company five different ways — and all five might be technically correct. The problem is that often, those answers don’t fully line up. That gap in a startup’s narrative creates friction.  Investors may understand the problem but still don’t feel like the story lands. Candidates may understand the product, but they’re not fully on board with the missi...

Hiring is one of the hardest things for first-time founders to get right, especially if you’re building a distributed team that spans the globe. For this episode, I spoke to Isaac Saul Kassab, co-founder of Pearl Talent, a recruiting firm that helps startups hire offshore teams. We break down the underlying hiring frameworks founders can actually use, whether you’re hiring locally or globally. We...

Technical founders don’t usually struggle with what they’re building. They struggle with explaining it clearly, quickly, and in a way that makes someone want to invest. In this episode, I spoke with Sheena Jindal, Managing Partner and Founder of Sugar Free Capital, about how technical founders can de-risk themselves before they ever get on a call with a VC. Sheena meets hundreds of founders each q...

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...

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 understa...

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...

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 com...

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 Africa...

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 certai...

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 th...

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...

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 al...

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 po...

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...

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 e...

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 Ti...

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 you...