Fund/Build/Scale

Why Black Startup Founders Have to Play a Different Game

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
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Thanks for listening!
 
 – Walter.

Building an Enterprise AI Startup from Day Zero

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
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Thanks for listening!
 – Walter.

Building in Layers: The Compound Startup Playbook

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
 
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Thanks for listening!
 
 – Walter

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

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
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Thanks for listening!
 – Walter

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

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
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Thanks for listening!
 
– Walter.

The "Marionette Threat" of Generative AI with All Tech is Human’s David Polgar

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. 
RUNTIME 19:50
 
LINKS
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)
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Thanks for listening!
 
– Walter.

Cyan Banister & Cristian Cibils Bernardes: Early Signals, Founder-Investor Fit, and Trustworthy Consumer AI

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!
EPISODE BREAKDOWN
(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?”
RUNTIME 47:19
LINKS
Cristian Cibils Bernardes
Cyan Banister
Autograph
Long Journey Ventures
The Ugly Duckling
SISU
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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.

From Engineer to CEO: Ryan Wang on Building Assembled and Finding Product-Market Fit

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.
RUNTIME 53:40
_
EPISODE BREAKDOWN
(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?
LINKS
Assembled
Ryan Wang
Brian Sze
John Wang
Stripe
Kelly Sims, Thrive Capital
Jack Altman, Alt Capital
Jen Ong Vaughan, Head of Strategic Ops, Stripe
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Thanks for listening!
 
– Walter.
 

The Starting Five: How to Build a Leadership Team That Can Scale

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 someone with a flashy resume can set you back two years.
If you’re building a people-first business, this episode is your blueprint for doing it right the first time.
RUNTIME 35:14
 
EPISODE BREAKDOWN
(2:24) Chris explains how his career path led him to become CEO of Tercera.
(6:18) The most common problems and challenges he helps founders navigate.
(9:17) What stage are the professional services startups Chris typically meets with?
(11:06) How he defines founder-market fit.
(13:31) Red flags that indicate a founder isn’t ready to work with investors.
(16:15) One of the constructs of our fund is [that] none of our investments compete with each other.”
(17:34) After the CEO, “ those five supporting cast members — key lieutenants — are essential.”
(19:11) In most cases, three of the original Starting Five need to be replaced.
(22:29) “ I've fallen into that trap myself — I hired a bunch of those that look amazing on paper.”
(24:29) A framework for finding your first executive marketing hire.
(27:17) Don’t let your board pressure you into making rushed staffing decisions.
(29:37) Managing the ripple effects associated with rebuilding the Starting Five “is really, really hard to do.”
(31:29) Chris shares his preferred format for board meetings.
(33:00) The one thing he wishes every founder understood before they started raising money. 
LINKS
Chris Barbin
Tercera
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Thanks for listening!
 

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

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, Viraj explains what a Field CTO really does, how the role evolved at Astronomer, and when founders should consider creating one. He also shares lessons on customer discovery, team dynamics, and how to turn technical insight into business momentum.
RUNTIME 31:16
EPISODE BREAKDOWN
(2:20) What is Astronomer, and when did the company get started?
(3:51) How the founding team came together.
(6:39) How Viraj collaborated with CTO Julian LaNeve to develop the Field CTO role.
(8:28) Where their roles overlap — and where they each take ownership.
(11:42) “We were at a point where we were really trying to standardize our sales process.”
(13:20) How the Field CTO role is different from a sales engineer or solutions architect.
(15:39) “ Talking to customers is a very humbling thing every day because you just realize how much you have to learn.”
(19:14) “ At a really early stage of customer development, the Field CTO role is almost like an external-facing product manager.”
(21:46) Viraj talks about the processes and tools he uses to share customer feedback internally.
(24:48) How to be a staunch customer advocate without losing your business focus.
(26:55) What’s the biggest opportunity cost associated with not having a Field CTO?
(30:13)  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? 
LINKS
Viraj Parekh
Julian LaNeve
Astronomer
Apache Airflow
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Thanks for listening!
– Walter.