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

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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.

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

• Payton Dobbs
• Hoxton Ventures
• White paper: Europe’s Sputnik Moment
• NVIDIA partnership: Accelerating the UK’s AI Startup Ecosystem

📥 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.

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 just trying to understand where this whole industry is headed, his perspective is a valuable counterweight to the hype cycles.

************

On this episode of Humans of AI, presented by Writer, we’re joined by David Polgar, founder of All Tech is Human, a non-profit and community dedicated to bringing together people, organizations, and ideas to grow and strengthen the Responsible Tech ecosystem. David shares some harrowing stories from the early days of social media that led him to where he is today – at the intersection of tech and human rights, AI and ethics. A lawyer and educator at the forefront of a movement “altering the DNA of tech development,” David is determined to create spaces and communities for human conversations and connections so that together we can shape the future of AI.

Subscribe now so you don't miss an episode!

Check out Writer’s Youtube channel to watch the full interviews.

Learn more about Writer at writer.com.

David Ryan Polgar

Humans of AI: Presented by Writer (podcast)

Navigating the ethical implications of generative AI with All Tech Is Human’s David Polgar (Writer blog)

Alaura Weaver

Communicating Your Vision with May Habib (CEO, Writer) and Gaurav Misra (CEO, Captions)

📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://www.linkedin.com/newsletters/7249143254363856897/

📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/

Thanks for listening!

– Walter.

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 indicators, and a trust-by-design stance; Cyan unpacks the decision rules and behaviors that earn a second meeting. Together, they outline small-budget experiments and the frameworks they use to create products that stick. For first-time founders and early operators, this episode delivers concrete steps you can start taking tomorrow.

Thanks very much to Jenna Birch and the team at SISU for co-hosting and making this live recording possible!

(1:54) Why Cristian named Autograph’s AI agent “Walter.”

(3:37) When they connected, Cristian saw “a bunch of synchronicities along the way that just kept pointing in this direction.”

(4:59) Cyan: “When he showed up and we were sitting together having coffee, I immediately was like, ‘yes.’”

(6:03) The sheer number of coincidences linking these two is unsettling — “quantum entanglement” comes to mind.

(8:18) Cristian and Cyan share their non-consensus takes on consumer AI.

(10:53) Cyan describes the framework she’s using to assess early signals as an investor.

(12:51) “I will not look at your résumé. I won’t look at what you did. Whatever you tell me in that interview is what I’m going to go off of.”

(14:42) “Fundraising is grueling. It was 50 conversations before I met Cyan, and then I had, I think, another 30.”

(16:53) Cyan’s framework for backing vs. passing.

(18:26) The three essential ingredients Long Journey Ventures seeks in founders.

(22:00) What a “magically weird” founder looks like — and why they’re so valuable.

(26:15) A red flag that ensures you won’t get a second meeting with Cyan.

(27:52) A behavior that virtually guarantees a second meeting.

(29:45) Cristian describes Autograph’s moat.

(34:40) “This whole thing doesn’t work if the trust element isn’t there.”

(38:08) What founder-investor fit looks like in their working relationship.

(41:57) One experiment founders should run this week.

(43:10) The most underrated founder superpower.

(44:10) “If you were interviewing for a job at an early-stage startup, what’s one question you’d have to ask the CEO before you could take the offer?”

• Cristian Cibils Bernardes
• Cyan Banister
• Autograph
• Long Journey Ventures
• The Ugly Duckling
• SISU

📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/

📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/

Thanks for listening!

– Walter.

***********************************

This event and recording are independently produced by Fund/Build/Scale and co-hosted with SISU. We are not affiliated with, endorsed by, or sponsored by TechCrunch or TechCrunch Disrupt. “TechCrunch” and “Disrupt” are trademarks of their respective owners.

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 mindset
• What it takes to lead through AI disruption and build for adaptability

Whether you’re building your first team or figuring out your second act, Ryan’s story is a masterclass in scaling deliberately while staying flexible.

_

(2:35) “ I was employee number 80 or so at Stripe, working on machine learning for fraud detection.”

(5:08) If you’re doing diligent customer discovery, working harder does not get you ahead faster.

(7:27) How Assembled’s founding team, er, assembled.

(8:47) “ There was a period, maybe the first year and a half or so, where there was no CEO.”

(10:33) Ryan explains the mindset that took him from software engineer to CEO.

(12:30) “ ‘Brother mode’ is both a feature and a bug at the same time.”

(14:58) How Assembled arrived at workforce management as its unique value proposition.

(17:48) Ryan talked to more than 100 prospects during the customer discovery process.

(19:00) The exercise they used to develop their initial customer personas.

(22:24) “ We took a really, really long time to hire for product. It was probably four or five years into the company.”

(25:00) Who was Assembled’s first design hire?

(27:26) To acquire product-market fit, “ we started with just a simple automation value proposition.”

(30:26) “ A lot of folks wanted to invest in Stripe alums, and Stripe led our seed.”

(33:35) Why customer support ops is — and will continue to be — such a huge opportunity.

(36:41) A good mission statement defines the change you want to see in the world.

(41:41) “ People who really do feel committed to a large mission, they understand that to get there is gonna require a lot of schlep.”

(43:55) How Assembled used a startup-within-a-startup mindset to innovate.

(48:47) “ We reassigned folks internally, and the key really was the order of operations.”

(51:31) If you were interviewing for a job with an early-stage startup, what’s one question the CEO would have to answer before you could take the offer?

Assembled

Ryan Wang

Brian Sze

John Wang

Stripe

Kelly Sims, Thrive Capital

Jack Altman, Alt Capital

Jen Ong Vaughan, Head of Strategic Ops, Stripe

📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/

📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/

Thanks for listening!

– Walter.