Fund/Build/Scale

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 engineering, why customer interviews aren't enough to validate an idea, and why early-stage founders need to spend more time testing demand than perfecting roadmaps. We discuss the case-study approach she uses to find customers, the controversial belief that the only real product validation is money, and what happened when a LinkedIn post generated a 1,000-person waitlist almost overnight. Shanea also shares how she used more than 100 customer calls to shape Empromptu’s direction, why she stopped fundraising when the company took off, and the go-to-market challenges that still keep her up at night. If you're a technical founder trying to figure out whether you're building something people truly want, this episode offers a practical framework for separating genuine demand from wishful thinking. Listen to this episode if you're trying to figure out: why sales validation should happen before you commit to a roadmap how to find your first customers using the case study method what a viral waitlist can teach you about product-market fit how to distinguish customer feedback from customer demand why technical founders need to learn sales earlier than they think which early traction signals are worth trusting — and which aren't how to validate an idea before spending months building it RUNTIME 49:06 EPISODE BREAKDOWN (3:16) What Is Empromptu.ai, and Who Is it For? (6:25) Sales Is Just as Complicated as Engineering (8:14) The Case Study Method for Finding Early Customers (11:56) Why Al Is Rewriting the Product Playbook (13:37) The Only Real Product Validation Is Money (17:10) The S***ty Purple Website That Predicted Impromptu's Viral Launch (21:38) What 100 Waitlist Calls Taught Shanea About Customer Demand (26:28) "We evolved the platform." (34:57) "Ninety-nine percent of VCs are great at one thing." (36:20) The GTM Problem That Still Keeps Shanea Up at Night (39:02) A Process for Selecting Your First Sales/Marketing Hires (40:59) Why She'd Hire a "Scrappy" Marketer Over a Former Meta Employee "Every Time" (44:05) The Early Traction Signal She No Longer Trusts (45:28) A 30-day Experiment Founders Can Run To Validate Their Idea LINKS Shanea Leven Empromptu.ai Empromptu raises $2M pre-seed to help enterprises build AI apps, 12/9/2025, TechCrunch 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

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.

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

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.

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 SUBSCRIBE 📥 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.