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20VC with Harry Stebbings· Mar 28, 2026Podcast · 2 speakersGili Raanan on Venture Entry Prices, Growth and Private-Market LiquidityGuest Gili Raanan · Host Harry StebbingsThe Cyberstarts founder explains his approach to cybersecurity investing, when he discusses margins and why secondary sales can help employees and limited partners.
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Unsupervised Learning: With Jacob Effron· Apr 15, 2025PodcastThe Transformer Co-Author Who Says Scaling Hit a WallHost Jacob EffronCohere CEO Aidan Gomez tells Redpoint that a $100 million model is still an amnesiac genius, and that enterprise AI money is concentrating in support, research, and the back office.
1:01:53ENUnsupervised Learning: With Jacob Effron· Mar 28, 2025PodcastOpen-source models are 5% of enterprise use — and GPT wrappers wonHost Jacob EffronLatent Space's Swyx and Alessio join Redpoint to map what actually has product-market fit in AI, and why the application layer is the fight that matters.
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Sequoia Capital· Mar 18, 2025PodcastGoogle Labs Pops Champagne at 10,000 Weekly UsersJosh Woodward on fifty-day sprints, fading paragraph prompts, and why a number Search would never notice is the point of an AI incubator.
1:15:28EN20VC with Harry Stebbings· Jan 6, 2025Podcast · 2 speakersMike Maples on Seed Investing, Founder Fit and When to SellGuest Mike Maples · Host Harry StebbingsThe Floodgate investor explains his approach to fund economics, exceptional founders, follow-ons and partial exits.
50:08EN20VC with Harry Stebbings· Aug 9, 2024Podcast · 2 speakersDax Dasilva on Bootstrapping Lightspeed, Growth and Returning as CEOGuest Dax Dasilva · Host Harry StebbingsThe Lightspeed founder explains how close customer observation shaped its product, why he returned to lead a profitable-growth transition, and what acquisitions left unfinished.
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No Priors: AI, Machine Learning, Tech, & Startups· May 23, 2024Podcast · 2 speakersFrom $6 million to $30 million ARR in three months: Garry Tan on YC’s AI boomHost Sarah Guo, Elad GilThe Y Combinator president tells Sarah Guo and Elad Gil why this batch looks like nothing he has seen in twenty years, and why a weak elephant is good news for startups.
1:10:18EN20VC with Harry Stebbings· May 13, 2024Podcast · 2 speakersTom Blomfield on YC, Fundraising and the Founder’s JobGuest Tom Blomfield · Host Harry StebbingsThe Monzo co-founder and YC partner discusses selecting founders, running a batch and balancing a large vision with immediate execution.
1:02:14EN20VC with Harry Stebbings· Apr 24, 2024Podcast · 2 speakersRujul Zaparde on Building Zip, Hiring for Potential and Moving FastGuest Rujul Zaparde · Host Harry StebbingsThe Zip co-founder explains how a procurement problem became a company, why repeatability matters, and how he balances speed with creativity and careful hiring.
1:44:48EN20VC with Harry Stebbings· Apr 22, 2024Podcast · 2 speakersDaniel Dines on Building UiPath, Risk and Finding PeaceGuest Daniel Dines · Host Harry StebbingsThe UiPath founder traces his path from learning C++ without a computer to finding a global market for automation, and reflects on leadership, money and the costs of growth.
52:54EN20VC with Harry Stebbings· Apr 17, 2024Podcast · 2 speakersVickie Peng on Building Less, Measuring Customer Value and Finding Product-Market FitGuest Vickie Peng · Host Harry StebbingsThe Sequoia product leader explains how to learn with less product, choose meaningful metrics and recognize different customer mindsets.
1:09:17EN20VC with Harry Stebbings· Mar 18, 2024Podcast · 2 speakersGili Raanan on Seed Investing, Founder Selection and Cyberstarts’ Sunrise ProcessGuest Gili Raanan · Host Harry StebbingsThe Cyberstarts founder explains his focus on teams, structured customer discovery and building cybersecurity companies.
1:24:10EN20VC with Harry Stebbings· Sep 20, 2023Podcast · 4 speakersIs the Venture Capital Model Broken? A Debate on Prices, Product-Market Fit and ReturnsGuest Eric Paley, Mike Maples, Jason Lemkin · Host Harry StebbingsEric Paley, Mike Maples and Jason Lemkin debate seed valuations, AI hype, fund returns and the choices founders face after raising too much.
1:10:10EN20VC with Harry Stebbings· Aug 16, 2023Podcast · 2 speakersBrian Balfour on Growth Loops, Channel Fit and Building a Repeatable Growth SystemGuest Brian Balfour · Host Harry StebbingsThe Reforge founder and former HubSpot growth leader explains how to identify constraints, choose channels and avoid mistaking attention for sustainable growth.
1:18:41EN20VC with Harry Stebbings· May 24, 2023Podcast · 2 speakersGuy Podjarny on Snyk, Product-Market Fit and Building Durable AdvantageGuest Guy Podjarny · Host Harry StebbingsThe Snyk founder and angel investor explains how to reason about future markets, focus messaging and learn through iteration.
1:33:36EN20VC with Harry Stebbings· Apr 5, 2023Podcast · 2 speakersMike Salguero on Bootstrapping ButcherBox and Subscription EconomicsGuest Mike Salguero · Host Harry StebbingsThe ButcherBox founder explains customer acquisition, per-box margins and the trade-offs behind building without venture capital.
1:03:08EN20VC with Harry Stebbings· Mar 29, 2023Podcast · 2 speakersJag Duggal on Customer Discovery, Product Strategy and Scaling NubankGuest Jag Duggal · Host Harry StebbingsNubank’s product leader explains why clear hypotheses, customer love and small autonomous teams matter as a company grows.
1:03:41EN20VC with Harry Stebbings· Mar 15, 2023Podcast · 2 speakersAdam Grenier on Building Growth into the BusinessGuest Adam Grenier · Host Harry StebbingsThe former Uber growth leader explains marketplace acquisition, hiring, retention and the limits of attribution through lessons from Uber, Lambda School and MasterClass.
1:01:55EN20VC with Harry Stebbings· Feb 16, 2023Podcast · 2 speakersMike Duboe on Growth Teams, Experiments and Paid MarketingGuest Mike Duboe · Host Harry StebbingsThe former Stitch Fix growth leader explains how to choose meaningful metrics, hire for growth and test whether marketing actually creates demand.
48:52ENNo Priors: AI, Machine Learning, Tech, & Startups· Feb 9, 2023Podcast · 2 speakersUsers Wanted a Better Brush. Runway Built One-Click GreenscreenHost Sarah Guo, Elad GilRunway CEO Cristobal Valenzuela on why a model is not a product, why filmmakers hacked a four-frame-per-second tool, and why 80 percent is enough when nobody dies.
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Lex Fridman· Jul 29, 2022Podcast · 2 speakersA Hundred Users Signed Up and Never Came BackGuest Brian Armstrong · Host Lex FridmanCoinbase CEO Brian Armstrong on the buy button that found product-market fit, why he wants customers to leave his platform, and a company that refuses to be a political square.
2:44:38ENLex Fridman· Nov 23, 2021Podcast · 2 speakersPosting a photo of this moment was not a product category yetGuest Kevin Systrom · Host Lex FridmanKevin Systrom tells Lex Fridman how Instagram began as a failed check-in app, hid a slow upload behind a caption screen, and later sold a thirteen-person company to Facebook for a billion dollars.
37:38ENLex Fridman· Sep 19, 2019Podcast · 2 speakersThe Best-Selling Vacuum in America Is a RobotGuest Colin Angle · Host Lex FridmaniRobot CEO Colin Angle on why most robotics companies die, why a Roomba is costed by weight, and why printing privacy promises on the box would hurt sales.
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Lenny's PodcastPodcastThe Zero-Day Marketing Exploits Behind Breakout StartupsHost Lenny RachitskyAlistair Croll explains how founders can find unfair distribution advantages by subverting platforms, norms, and regulations—without actually being evil.Load moreShowing 24 of 64