Fund/Build/Scale

In this episode, I’m joined by Jon Callaghan, co-founder and managing partner at True Ventures, and Julie Bornstein — CEO of Daydream, founder of The Yes, and former COO of Stitch Fix — to break down what investors really evaluate in the first 18 months of a company’s life. Drawing from their shared history as investor and founder, we talk candidly about runway, hiring before certainty exists, conviction versus ego, and how trust between founders and investors gets tested when plans change. Julie explains how she approached budgeting and milestones for The Yes as a non-technical founder, while Jon shares how early-stage investors assess learning, decision-making, and leadership long after the pitch meeting ends. RUNTIME 50:28 EPISODE BREAKDOWN (2:43) Jon: “Julie and I met in graduate school.” (4:24) Julie chose a different VC firm for her first seed round at The Yes (10:33) How would Jon have assessed The Yes if he didn’t know Julie? (13:14) Julie: “Runway is your best friend and your biggest gift.” (14:59) How non-technical founders can sketch out a financial model (22:37) Jon: “There’s an immense river of goodness that flows underneath Silicon Valley.” (25:30) How did True Ventures size up SAM for The Yes? (29:00) Only work with engineers who understand your problem (31:25) Some of Jon’s post-check expectations for founders (41:44) What are some questions founders should ask VCs in their first meeting? (45:42) One experiment a pre-seed/seed-stage founder can try next week (48:14) The final question LINKS Julie BornsteinJon CallaghanTrue VenturesDaydreamTop e-commerce veteran Julie Bornstein unveils Daydream—an AI-powered shopping agent that’s 25 years in the makingPinterest to Acquire THE YES, an AI Powered Shopping Platform for FashionStitchFix 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

For years, founders have been told to build a defensible moat. But in AI, where platforms, models, and capabilities can shift overnight, that advice is starting to feel outdated. In this episode of Fund/Build/Scale, Simular CEO and co-founder Ang Li talks about what it actually means to build a company when the underlying technology won’t sit still. Rather than evangelizing agents or predicting the future of work, Ang gets unusually candid about fragility, speed, judgment, and how founders should think when technical advantages may be temporary by default. The conversation digs into small-team execution, founder productivity, decision-making under uncertainty, and the uncomfortable question many AI founders avoid: what if the next platform update eats your product? Note: This interview was recorded before Simular closed its $21.5M Series A in December 2025. RUNTIME 56:44 EPISODE BREAKDOWN (1:52) What is Simular, and how does it work? (6:11) How Ang and co-founder Jiachen Yang connected (9:00) How much time passed between Day Zero and serving their first customer? (13:54) The moment Ang realized " this is gonna be like something huge." (17:21) How he approaches founder-led sales and what he looks for in a GTM hire (26:34) Maintaining cohesion when you're leading a distributed team (32:23) Should you hire a new employee, or build a new agent? (34:50) Why Ang made talking AI gorillas part of Simular's GTM strategy (38:20)"If everyone becomes too cautious there, that actually prevents the innovation part." (43:55) "There's never a moat on anything." (51:16) The final question LINKS Ang Li Jiachen Yang Simular Meet the AI Agent with Multiple Personalities, Wired, 4/16/2025 Simular Raises $21.5M to Build Autonomous Computer Agents, 12/2/2025 What is Robotic Process Automation (RPA)?, IBM 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 most founders look at markets dominated by Google or Apple, they see a dead end. Ariel Seidman saw an opening. Before founding Hivemapper, Ariel helped scale Yahoo Maps during a period when search and mapping were rapidly evolving. That experience gave him a front-row seat to how large-scale mapping systems are built — and how technical, capital, and organizational constraints shape the pace of innovation at scale. In this episode, he breaks down what it really takes to build a startup against giants: why data moats matter more than UI, how to layer products instead of attacking incumbents head-on, and how insider knowledge can become an unfair advantage — if you’re willing to unlearn Big Tech habits that don’t translate to startups. We also dig into Hivemapper’s decentralized approach to mapping, the role of physical AI and real-world data, the tradeoffs behind crypto incentives, and why the future of maps looks more like a spatial intelligence platform than a navigation app. If you’re thinking about taking what you’ve learned inside Big Tech and applying it to your own startup, this is a conversation you’ll want to hear. RUNTIME 46:57 EPISODE BREAKDOWN (2:11) What is Hivemapper? (6:34) Scaling Yahoo Maps: Lessons from an Early Market Leader (9:04) Why Capital and Infrastructure Matter More Than Design (11:49) From Insider to Founder: Deciding to Build Again (15:00) Customer Discovery at Scale: Coverage, Accuracy, and the Long Tail (19:10) Beyond Navigation: Maps as a Spatial Intelligence Platform (22:46) Big Tech vs. Startups: Some Skills Transfer — and Some Don't (27:31) Building Against Giants by Building One Layer at a Time (31:39) Creating a Double Flywheel (and Making it Spin) (45:10) The Final Question LINKS Ariel SeidmanHivemapperBeemapsHivemapper network blogHivemapper Raises $18M From Multicoin Capital to Create the World’s First Decentralized Mapping NetworkBee Maps, Powered by Hivemapper, Raises $32 Million to Scale the Next Generation of AI-Powered Mapping 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.

Odille Sánchez leads the Tech and Scientific-Based Entrepreneurship Center of Excellence at Tecnológico de Monterrey, where she works with hundreds of early-stage founders across Latin America. In this episode, she explains how mindset, methodology, and community are reshaping what it means to launch a startup in a region where early capital is scarce and institutional support is fragmented. We also talk about: Whether you're supporting under-networked founders or trying to build in an emerging market, Odille offers a clear-eyed look at what it really takes to go from scarcity to scale. RUNTIME 37:46 EPISODE BREAKDOWN [2:10] Mission-Driven Work at Tecnológico de Monterrey [5:20] Resource Orchestration, Not Acceleration [6:45] " We work with a lot of profiles." [8:47] Bridging The Cultural Gap Around Risk-Taking [11:37] A Founder Success Story: Ricardo Baez + Safe Fruit [14:06] What to Do When You Don’t Have a Network [17:06] The Disconnect Between Capital and Opportunity [20:42] How Latin American Founders Can Engage Global Angel Investors [23:02] The Missing Skillset: Commercialization [30:08] What Silicon Valley Advice Doesn’t Translate [34:43] Odille’s Parting Advice for Outsiders LINKS Odille SánchezCentro de Prensa dl Tecnológico de MonterreyShaping Innovation and Entrepreneurship Ecoystems: An Outcome-based ModelFrom reflection to intention: Rethinking how we build startups and innovation ecosystems 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: 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 NormanSean GreenBlack Operator VenturesQ2 2025 Black Venture Funding ReportShare Of Startup Funding For Black Founders Hits Multiyear LowThe State of U.S. Household WealthThree in Ten Black Americans Over Age 25 Hold a Bachelor’s Degree 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 ReeseLanaiSteve HerrodJuxtaposeGeneral CatalystSplunkDatadogWhy You Will Marry the Wrong Person 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...

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: 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 DobbsHoxton VenturesEurope’s Sputnik MomentAccelerating 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.

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) SUBSCRIBE 📥 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! 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 BernardesCyan BanisterAutographLong Journey VenturesThe Ugly DucklingSISU 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.

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: 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 ----more---- 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 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.

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 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!

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 ParekhJulian LaNeveAstronomerApache Airflow 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.

More startups die from co-founder breakups than from running out of money. Attorney David Siegel, a partner at Grellas Shah LLP, has spent years inside these conflicts, helping founders navigate everything from equity disputes to emotional meltdowns. In this conversation, he explains: If you’re thinking about starting a company with someone else, or already rowing in that two-person boat, this episode will show you what’s at stake — and what to do before it’s too late. If you thought The Social Network had a happy ending, you might want to skip this one. RUNTIME 47:35 EPISODE BREAKDOWN (2:15) Disclaimer: “If you're looking for legal advice, that's something to talk to your own lawyer about.” (4:14) When it comes to equity distribution, “the fifty-fifties are a 5%.” (7:14) What are the most common triggers that lead to co-founder breakups? (11:35) What steps can a minority co-founder take to protect their equity in the earliest stages? (15:23) Ultimately, “the only person the lead investor knows is the majority founder.” (17:06) As long as you document all oral agreements, “you should be in good shape.” (20:04) Draw up agreements for any advisors or consultants you add to the cap table. (22:36) “The initial calls around a co-founder dispute, we play 50% lawyer, 50% therapist.” (25:17) “Breakups where it's not a surprise to the founder being kicked out are usually the smoothest.” (28:05) Once outside money comes in, minority co-founders leave with less than they agreed to. (30:09) How negotiable is retaining the co-founder title after a breakup? (32:32) Pre-agreed severance and other ideas for reducing financial pain and hard feelings. (35:05) “What a minority founder can do: you need face time with the investor.” (38:44) When should the founder with less equity contact a lawyer? (41:15) The most common mistakes founders make during a breakup. (44:43) The one thing David wishes more founders understood before picking a co-founder or investor. LINKS David SiegelGrellas Shah LLP 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.

What do you do when everyone loves your product but no one’s paying for it? That was the challenge facing Beautiful.ai. Founder Mitch Grasso nailed the product, but to build a sustainable business, he brought in operator Jason Lapp as CEO. In this conversation, Jason shares how Beautiful.ai killed its freemium tier, introduced a credit-card-gated trial without losing momentum, and learned to serve both self-serve and enterprise customers at the same time. He also explains how to listen to customer feedback without becoming a feature factory, and why non-technical founders shouldn’t try to know everything about the tech stack. If you’re a founder wondering when to put up a paywall — or how to balance PLG with enterprise sales — here's a playbook. RUNTIME 46:20 EPISODE BREAKDOWN (3:35) “ The timing of us coming together was really fortuitous for beautiful because he had already built the first version of beautiful and put it in market.” (6:28) “ Microsoft and Google report that there's close to a billion people that use presentation software on a monthly basis.” (10:51) “ At a certain point after getting in market, you start to get a different set of signal.” (14:52) The free trial period is a great opportunity to learn about what customers value most. (19:56) Leverage “emotional” feedback to improve the customer experience. (23:46) “ We do have a guiding principle, which is: on the customer side, we generally don't build for one customer need.” (26:17) Beautiful.ai uses NPS surveys to gather feedback from enterprise and individual users. (28:49) Since pivoting to paid, they have separate teams for enterprise and individual customers. (23:02) “ We think about an ICP, and then we think about an IECP, meaning the enterprise as a whole.” (33:57) Capturing behavioral and attitudinal data to understand customer behavior. (37:18) How the broader rise of generative AI has influenced GTM strategy. (42:33) Jason shares some advice for non-technical CEOs. LINKS Jason LappBeautiful.aiAI Isn’t Coming For Jobs, It’s Coming For InefficiencyContinuous Discovery Habits: Discover Products that Create Customer Value and Business ValueEverything You Need to Know About Freemium Pricing 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.

Frontier tech startups don’t fail because the science is bad — they fail because no one needs what they’re building. In this episode, Roadrunner Venture Studios CEO/co-founder Adam Hammer explains how to avoid that fate. We talk about why the U.S. struggles to turn research into startups, why being right isn’t enough, and what it really takes to cross the Valley of Death between lab science and real-world demand. Along the way, Adam shares practical insights for first-time founders, including: If you’re building something deep, hard, or new — don’t skip this one. RUNTIME 41:11 EPISODE BREAKDOWN (2:32) How a career spanning national labs, venture capital, and startup leadership led to Roadrunner Venture Studios. (7:46) “ Our goal is to compress all the mistakes that you would make in a three-year period into a year.” (8:50) The three frontier tech sectors Roadrunner focuses on: advanced energy, advanced manufacturing, and advanced compute. (10:28) Why it’s so hard to translate lab science into sustainable, venture-scale businesses. (13:49) Adam shares ideas for bridging America’s structural gap in commercializing frontier tech. (16:38) “ Roadrunner serves as a de-risking mechanism for ideas and for people.” (21:12) “ In science, you win by being right. But in startups, you win by being useful.” (24:23) What Adam looks for in a pitch deck. (27:15) When it comes to sourcing founders and ideas, “ we are as early as it gets.” (31:54) Why Roadrunner Venture Studios set up shop in New Mexico. (34:16) If he could fix one common founder misconception, what would it be? (36:26) “ There's nothing innate that predetermines whether somebody can or cannot be a founder.” LINKS Adam HammerRoadrunner Venture StudiosThe EngineOvercoming the Valley of Death: A New Model for High Technology Startups 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.

You don’t need a Stanford degree or a flashy deck to raise a pre-seed, seed or Series A, but you do need to show investors that you’ve put in the work. 645 Ventures co-founder Nnamdi Okike shares practical advice for founders who are prepping to raise capital, including what he looks for in pitch meetings, how to uncover “earned secrets,” and why chasing hot categories can backfire. We also dig into how 645 uses outbound sourcing and proprietary software to spot overlooked talent — and what it really takes to stand out if you don't fit the typical founder mold. RUNTIME 58:08 EPISODE BREAKDOWN (2:18) Nnamdi describes his path from operator to investor. (5:00) Stage by stage: What sets 645 Ventures apart from other firms? (12:33) What signals and sectors suggest strong alignment with 645? (21:04) “We do have some solo founders in the portfolio.” (25:49) His take on CEOs who promote a hard-charging, aggressive culture. (31:20) Why he favors founders solving real problems, not just chasing trends. (37:02) One thing he wishes more first-time founders understood about the early-stage ecosystem. (43:55) What kind of proof or evidence he looks for in companies raising capital. (49:20) Which early assumptions he and his team have since modified —or thrown out. LINKS Nnamdi OkikeAaron Holiday645 VenturesPattern BreakersKaren Moon 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.

Dan Lee co-founded what would become Nooks while on leave from Stanford. He wasn’t solving sales. He was exploring remote collaboration during the pandemic. But when they noticed that some of his most active users were in sales development — and that investors were starting to reach out — he followed the signal. Today, Nooks is a sales AI platform used by teams at Seismic, Fivetran, and Modern Health, with $70 million in funding from Kleiner Perkins, Lachy Groom, and others. In this episode, we talk about how Nooks evolved from a virtual office for remote collaboration into a fast-growing AI sales assistant platform. Dan shares what it’s like to raise a $43M Series B after an unplanned Series A, why he believes sales needs AI assistants, not agents, and how he built conviction in a space he had no background in. If you’re an early-stage founder wondering how to navigate a pivot, build for an industry you’ve never worked in, or generate investor pull instead of push, listen in. RUNTIME 36:32 EPISODE BREAKDOWN (3:01) “ It started as a project, obviously became a company.” (5:13) “ Everyone here is smarter than me in some way.” (5:46) Which early signals indicated Nooks could be more than a side project? (8:01) “ And then, investors approached and said, ‘oh, you should raise some money.’” (10:11) “ I think it's a misconception to think that in the early days it's hard to do much without raising money.” (11:15) Pivoting Nooks from a virtual collaboration platform to serving sales teams. (14:26) “ At the time, it felt more like a focus than a pivot.” (16:56) “ Coming from an engineering background, it's easy to think, ‘oh, sales, that's like a dirty job.’” (20:50) “ We've been fortunate to have a very strong feedback loop with our users.” (22:20) If you don’t have domain expertise, “ build a mental model of what is true north in terms of product value.” (23:22) Nooks’ work culture is underpinned by two values: “ask why,” and “earn customer love.” (26:25) Customer satisfaction ≠ Customer delight (30:36) Why Nooks is building AI assistants, not AI agents. (32:41) When it comes to hiring, Dan looks for people with “motivations that align well with Nooks.” (34:39) One question Dan would have to ask a CEO if he were interviewing for a job with an early-stage startup. LINKS Dan LeeNooksNikhil CheerlaRohan SuriNooks raises $43M Series B from Kleiner Perkins and launches AI Sales Assistant PlatformForbes 30 Under 30 AI 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.

Transforming breakthrough research into a sustainable company is never simple — especially in hard tech. In this episode recorded in December 2024, Zero Emission Industries CEO/founder Dr. Joseph Pratt and Chief Strategy Officer John Motlow share what it takes to move hydrogen power systems from the lab to the marketplace. We talk about raising money in tough conditions, why government grants can be both a blessing and a constraint, and how to build teams that thrive under pressure. Along the way, they offer candid lessons on funding, hiring, and navigating timelines that rarely go as planned. RUNTIME 51:52 EPISODE BREAKDOWN (2:11) “ I knew the path on how to solve it and knew that there was demand for it, and took the jump out of the national lab to start the company.” (6:36) “ I didn't jump into this with a big network of investors.” (8:57) How ZEI produced the world’s first commercial fuel cell ferry. (10:56) Why the company’s first hire was a Chief Strategy Officer. (12:53) John Motlow says he wanted to join ZEI “because it was incredibly risky.” (17:06) Crafting ZEI’s GTM strategy for the FCV Vanguard, a hydrogen-powered, high-performance speedboat. (21:55) Is ZEI a transportation company, or a clean tech startup? (24:20) When it comes to deep tech, customer requirements are wayfinders for PMF. (29:47) “Government funding and their insights is sort of half the picture.” (35:30) “ To be clear, we talked to a lot of investors who did not agree with our TAM.” (39:09) Why they overindexed on hiring employees who have a background in motorsports. (42:19) Joe’s advice for building specialized teams in a competitive market. (47:38) “ Don't slot someone in there and then forget about it: Where are their strengths?” (49:27) What’s next for ZEI? LINKS Zero Emission IndustriesDr. Joseph PrattJohn MoslowFCV Vanguard — Live DemoZEI Raises $8.75 Million in Series A Funding SUBSCRIBE 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ Thanks for listening! – Walter.