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.

(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

• 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

📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw

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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.

(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

• Lexi Reese
• Lanai
• Steve Herrod
• Juxtapose
• General Catalyst
• Splunk
• Datadog
• Why You Will Marry the Wrong Person, Alain de Botton

📥 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.

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

Ben Borodach

April

Daniel Marcous

april Raises $38M Series B to Embed Tax into Every Financial Decision

April Careers

📥 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