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58:26ENGili Raanan on Venture Entry Prices, Growth and Private-Market LiquidityGast: Gili Raanan · Moderation: Harry StebbingsThe Cyberstarts founder explains his approach to cybersecurity investing, when he discusses margins and why secondary sales can help employees and limited partners.
51:08ENThe Transformer Co-Author Who Says Scaling Hit a WallModeration: 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.
1:01:53ENOpen-source models are 5% of enterprise use — and GPT wrappers wonModeration: 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.
51:16ENGoogle 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.
1:15:28ENMike Maples on Seed Investing, Founder Fit and When to SellGast: Mike Maples · Moderation: Harry StebbingsThe Floodgate investor explains his approach to fund economics, exceptional founders, follow-ons and partial exits.
50:08ENDax Dasilva on Bootstrapping Lightspeed, Growth and Returning as CEOGast: Dax Dasilva · Moderation: 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.
39:59ENFrom $6 million to $30 million ARR in three months: Garry Tan on YC’s AI boomModeration: 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.
1:10:18ENTom Blomfield on YC, Fundraising and the Founder’s JobGast: Tom Blomfield · Moderation: Harry StebbingsThe Monzo co-founder and YC partner discusses selecting founders, running a batch and balancing a large vision with immediate execution.
52:54ENVickie Peng on Building Less, Measuring Customer Value and Finding Product-Market FitGast: Vickie Peng · Moderation: Harry StebbingsThe Sequoia product leader explains how to learn with less product, choose meaningful metrics and recognize different customer mindsets.
1:09:17ENGili Raanan on Seed Investing, Founder Selection and Cyberstarts’ Sunrise ProcessGast: Gili Raanan · Moderation: Harry StebbingsThe Cyberstarts founder explains his focus on teams, structured customer discovery and building cybersecurity companies.
1:24:10ENIs the Venture Capital Model Broken? A Debate on Prices, Product-Market Fit and ReturnsGast: Eric Paley, Mike Maples, Jason Lemkin · Moderation: Harry StebbingsEric Paley, Mike Maples and Jason Lemkin debate seed valuations, AI hype, fund returns and the choices founders face after raising too much.
1:10:10ENBrian Balfour on Growth Loops, Channel Fit and Building a Repeatable Growth SystemGast: Brian Balfour · Moderation: Harry StebbingsThe Reforge founder and former HubSpot growth leader explains how to identify constraints, choose channels and avoid mistaking attention for sustainable growth.
1:18:41ENGuy Podjarny on Snyk, Product-Market Fit and Building Durable AdvantageGast: Guy Podjarny · Moderation: Harry StebbingsThe Snyk founder and angel investor explains how to reason about future markets, focus messaging and learn through iteration.
1:33:36ENMike Salguero on Bootstrapping ButcherBox and Subscription EconomicsGast: Mike Salguero · Moderation: Harry StebbingsThe ButcherBox founder explains customer acquisition, per-box margins and the trade-offs behind building without venture capital.
1:03:08ENJag Duggal on Customer Discovery, Product Strategy and Scaling NubankGast: Jag Duggal · Moderation: Harry StebbingsNubank’s product leader explains why clear hypotheses, customer love and small autonomous teams matter as a company grows.
1:03:41ENAdam Grenier on Building Growth into the BusinessGast: Adam Grenier · Moderation: Harry StebbingsThe former Uber growth leader explains marketplace acquisition, hiring, retention and the limits of attribution through lessons from Uber, Lambda School and MasterClass.
1:01:55ENMike Duboe on Growth Teams, Experiments and Paid MarketingGast: Mike Duboe · Moderation: Harry StebbingsThe former Stitch Fix growth leader explains how to choose meaningful metrics, hire for growth and test whether marketing actually creates demand.
48:52ENUsers Wanted a Better Brush. Runway Built One-Click GreenscreenModeration: 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.
2:29:24ENA Hundred Users Signed Up and Never Came BackGast: Brian Armstrong · Moderation: 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.
2:44:38ENPosting a photo of this moment was not a product category yetGast: Kevin Systrom · Moderation: 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.
37:38ENThe Best-Selling Vacuum in America Is a RobotGast: Colin Angle · Moderation: 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.
1:15:29ENThe Zero-Day Marketing Exploits Behind Breakout StartupsModeration: Lenny RachitskyAlistair Croll explains how founders can find unfair distribution advantages by subverting platforms, norms, and regulations—without actually being evil.
1:27:13ENFour Levels of Product-Market Fit: First Round's Playbook for B2B FoundersGast: Todd Jackson · Moderation: Lenny RachitskyTodd Jackson of First Round Capital walks through a staged framework for finding product-market fit, the benchmarks for each stage, and the four Ps you can change when you're stuck.
2:14:15ENEric Ries on the Lean Startup After 12 Years: What MVPs Really Mean, When to Pivot, and Building Companies for Human FlourishingGast: Eric Ries · Moderation: Lenny RachitskyThe author of The Lean Startup revisits misconceptions about MVPs and pivots, offers advice for stuck founders, and argues that governance, not just product, decides whether companies do good.
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