Fund/Build/Scale

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 venture capital without losing themselves in the process.  James and Sean also break down what they look for when leading seed rounds, why warm intros function as the first real filter, and how founders can manufacture momentum even without friends-and-family money. This conversation goes deep on: How to position yourself when you don’t start at the same starting line The difference between venture-scale companies and businesses that shouldn’t chase VC Why execution, storytelling, and follow-up matter more than polish How to turn cold outreach into real human capital Why Black founders are uniquely positioned to exploit the current AI moment If you’re an underrepresented founder trying to de-risk your leap, get into the right rooms, or understand why the rules feel unwritten — this conversation names the rules out loud. RUNTIME 54:24   EPISODE BREAKDOWN (1:52)  What motivated Sean and James to start Black Operator Ventures (6:51) Where are they looking for opportunities? (8:27) Top priority: Founders building real-world solutions with few regulatory hurdles (11:44) Why obtaining a warm intro to a VC is a founder's first test (15:20)  Fundraising is theater: Study the audience to learn your role (22:29) Red flags first-time founders should avoid waving (27:00) Tactical advice for aspiring founders who still work full-time jobs (30:24) “ It doesn't seem risky because we're betting on ourselves, and we believe we can do anything.” (34:38) How to find out if you should bootstrap or find a VC (38:30) Which signals tell Sean and James a founder is ready for a check (41:55) Why founders still need to spend some time in Silicon Valley (46:02) Black founders can " 10x ourselves with AI in ways that other people can't." (48:32) One action you can take this week to extend your network LINKS James Norman Sean Green Black Operator Ventures Q2 2025 Black Venture Funding Report, HBCUvc Share Of Startup Funding For Black Founders Hits Multiyear Low, Crunchbase The State of U.S. Household Wealth, Federal Reserve Bank of St. Louis Three in Ten Black Americans Over Age 25 Hold a Bachelor’s Degree, The Journal of Blacks in Higher Education SUBSCRIBE 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw   📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening!    – Walter.

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 walks through how she ran more than 200 customer interviews before committing to a product direction, why product-market fit isn’t real until someone is willing to pay, and how she’s building a 14-person team — plus AI “teammates” — without losing focus or trust. We also talk about fundraising in a tougher 2025 market, why early founders need to resist the urge to build comprehensive solutions too soon, and how organizational design is already changing as AI flattens hierarchies and reshapes work. If you’re thinking about starting a company — or you’re in the messy middle of finding product-market fit — this conversation offers a practical roadmap for what actually matters. RUNTIME 51:45   EPISODE BREAKDOWN (2:01) What Lanai does (5:05) Lexi’s customer discovery process — “definitely 200 interviews” (12:03) Why customer delight should be a founder’s obsession metric (15:36) What “AI productivity” actually means (19:12) Lexi’s framework for managing small, early-stage teams (26:23) Her take on seed-stage fundraising in late 2025 (31:54) How to integrate customer feedback into product strategy (38:00) The most meaningful proof a first-time founder can show an investor (40:53) Why “trust has a code” when it comes to teamwork (44:08) How Lexi stays obsessed with customers in every meeting (48:15) The final question LINKS Lexi Reese Lanai Steve Herrod Juxtapose General Catalyst Splunk Datadog Why You Will Marry the Wrong Person, Alain de Botton SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/   📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening!  – Walter.

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 frameworks he and his co-founder developed before they wrote any code. If you’re an early-stage founder deciding what to build — or how to build it — this episode offers a clear playbook for choosing hard problems and de-risking them the right way. RUNTIME 48:00   EPISODE BREAKDOWN 01:08  How Ben and Daniel met + connecting over complex data problems 01:47  Ben’s background: Deloitte, crypto infra, cyber, fintech 02:51  Why pick tax? Choosing a hard, high-impact market 03:44  Outdated incumbents + the opportunity hidden in “don’t touch that” markets 04:57  Why tax innovation is so rare: regulatory hurdles and decades-old engines 05:29  Founder-market fit: complementary backgrounds + AI expertise 06:38  Translating congressional law into code + achieving 20× engineering leverage 07:25  The pseudo-manifesto: conflict resolution, culture, and founder alignment 08:40  What “compound startup” means and why narrow wedges don’t work in B2B 09:57  Stitching data, workflows, and software into a flexible platform 10:39  Building for multiple configurations across financial institutions 11:26  How complexity becomes a moat 13:01  Why compound startups require longer gestation and patience 14:46  Sequencing layers: engine → coverage → interfaces → embedded infra 15:50  The rigid annual regulatory calendar and “Manhattan-style” planning 17:13  Serving customers early: friction with the market by design 18:46  Manual work vs. automation: the constant balancing act 19:27  The early KPI wasn’t revenue  it was proving technical and trust viability 20:46  Running “science experiments” to de-risk assumptions 21:16  Investor expectations vs. seasonal learning cycles 22:47  Surviving four years of annual gauntlets before scale 23:02  Inside the regulatory maze: IRS approval, state forms, arbitrary specs 24:04  Data governance challenges: CCPA, IRS 7216, portability 25:20  Why April participates in the industry’s private governance body 26:18  Why April chose embedded distribution over a consumer app 27:32  The crumbling moats of financial institutions 29:08  Tax as the missing data layer enabling personalization 30:47  How customer discovery differed across banking, wealth, and SMB 31:07  Thousands of conversations across dozens of institutions 32:51  What April had to prove at Seed, Series A, Series B 33:49  Why rigid VC benchmarks can be unhelpful for complex companies 37:02  Headcount growth: seed → A → B 38:20  Why Ben doesn’t interview every employee anymore 39:48  Founder evolution: doing → delegating → maintaining quality 40:55  Resilience, wellbeing, and founder longevity 41:39  The mythology of 996 and why it’s unsustainable 44:07  The most common mistakes first-time fintech founders make 46:14  The one question Ben would ask if he were interviewing a founder LINKS Ben Borodach April Daniel Marcous april Raises $38M Series B to Embed Tax into Every Financial Decision April Careers   SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw   Thanks for listening!    – Walter

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 Timberwolves and North Carolina Courage. In this episode, Jordy explains what it actually takes to break into a closed industry, why he reverse-engineers every funding round before he raises it, and the biggest mistake he refused to repeat as a second-time founder. RUNTIME 53:07 EPISODE BREAKDOWN (1:12) Breaking into pro sports, rebuilding fan experience, and reverse-engineering fundraising. (2:03) How Stella Connect (customer service) laid the foundation for Jump (customer experience for fans). (2:58) What Jump does today: a unified fan experience + data platform for teams. (4:11) The unusual founding plan: 3-4 years of R&D, designed to launch with an NBA franchise from day one. (5:46) Why sports is nothing like building a typical SaaS startup — more like a “car company” level of complexity. (6:48)The true barrier: a near-monopoly in ticketing that stops innovation cold. (7:59) Selling into a market where fans have low expectations — and why demand is obvious but still untapped. (9:54) Early customers as classic early adopters — every team already knows the pain points intimately. (11:25) The first hypothesis they had to kill: incumbents don’t want to integrate or share data. At all. (12:32) Designing for the actual fan demographic: season ticket holders skew 50+, so “cutting-edge UX” isn’t always the answer. (13:25) Jordy’s advice to founders: get out of the building, talk to insiders, but keep your “child’s mind.” (15:06) Sports as an industry you can’t “hack into” — it works more like fashion or Hollywood. (17:31) Moments when he realized he was losing stakeholders — and why being “comfortable in the uncomfortable” is essential. (18:03) Early would-be partners who backed out, the impact on morale, and what they learned from those rejections. (19:45) Jump’s origin as a “dynamic seating” idea — and why they had to build the entire platform instead. (21:03) The “invisible platform” ethos: why Jump melts into the background so teams can own the fan relationship. (23:10) Why NWSL teams and NBA franchises have surprisingly similar needs — and what that taught them about productizing. (24:36) Jordy’s litmus test for platform vs. point solution: how many people in the org depend on you to do their job? (27:01) Seed to Series A timeline — and how the Timberwolves sale collapsing delayed everything by a year. (28:37HaHow Jordy processed a crisis that was public, sudden, and existential. (31:13) The Long Beach pier walk: the moment he decided to pivot the GTM to a crawl-walk-run strategy. (32:49) Effectuation theory, the “bird in hand,” and how it led to NCAA → NWSL → Timberwolves as a survival sequence. (34:39) What he had to unlearn from Stella Connect: stop zooming in — zoom way out to a 10–20-year vision. (37:05) The habit he kept: talent above all else — and why his first call was to a Chief People Officer. (38:45) Minimum viable people function for early founders: fractional HR > junior recruiter. (42:58) High performance without grind culture: intensity ≠ toxicity — and why durability matters more than speed. (45:40) Hiring from big tech: what’s actually transferable, and the dangers of logo-blindness. (50:55) The one answer Jordy would need from a founder-CEO before he’d join their startup. LINKS Jordy Leiser Jump Alex Rodriguez Marc Lore Jump Series A announcement Delivering Happiness: A Path to Profits, Passion, and Purpose, Tony Shieh Effectuation — UVA Darden School of Business SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw   Thanks for listening!  – Walter

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 founders fail their first go-to-market quiz before the conversation even begins. He also talks about category creation, how to hire in the U.S. if you’re coming from Europe, why pricing is a strategic weapon, and the number-one question he asks every founder — the one that quietly decides whether you’re playing at venture scale or not. If you’re an early-stage builder, this episode will help you level up before you start meeting with VCs. RUNTIME 1:00:46   EPISODE BREAKDOWN 02:12: Payton Dobbs’ background and the value of building presence in key markets 03:25: Not all good ideas are venture scale: how to assess billion-dollar potential 04:01: Why new category creation is crucial for venture scale startups 06:35: What VCs look for in a pitch deck: TAM, SAM, and logic behind the numbers 08:06: Case study: Deliveroo and building new markets from small segments 09:07: Identifying pain points and leveraging founder expertise 10:57: Advice for technical founders: the value of complementary co-founders and commercial skills 12:23: Building frameworks: due diligence on markets, competitors, and learning from others’ mistakes 13:54: Adapting go-to-market strategies for different business models (B2B SaaS, consumer, etc.) 15:00: The importance of having a perspective and being able to debate your point of view 15:50: Solo founders vs. teams: most are teams, but solo founders can succeed too 13:28: The state of the AI ecosystem in Europe and why it’s accelerating 17:18: Navigating US immigration and talent: why keeping dev teams in Europe can be strategic 20:34: Common mistakes when entering the US: “If you build it, they will not come” 21:21: Do you need to reboot customer discovery in new markets? Sometimes, but not always 22:24: The importance of understanding the competitive landscape and customer needs in each market 24:54: Hiring in the US: cultural differences and what to look for in team members 27:33: Payton’s parting advice for founders expanding to the US: grind, network, and be relentless 28:36: Building sales ops from scratch: tools, systems, and process before people 32:05: Understanding and accruing value in the business value chain 34:45: Signals that a team can move from tech to traction: agility, speed, and adaptability 36:37: Pricing as an art and a science; lessons from Nest and Apple 40:00: Metrics: NPS, customer surveys, and forward-looking indicators 44:42: What Payton hopes to unlock for founders by being based in the US LINKS Payton Dobbs Hoxton Ventures White paper: Europe’s Sputnik Moment NVIDIA partnership: Accelerating the UK’s AI Startup Ecosystem SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening!   – Walter.