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1:19:47ENScott Kirby on United’s Fleet Bet, Starlink and Airline EconomicsGast: Scott Kirby · Moderation: John Collison, Ben ThompsonUnited Airlines CEO Scott Kirby explains how he thinks about investing through downturns, building technology and running an airline network.
1:00:39ENAmazon CEO Andy Jassy on the $220 Billion AI BuildoutGast: Andy Jassy · Moderation: Ben Horowitz, Erik TorenbergEven at roughly $220 billion of 2026 CapEx, Jassy says Amazon is still turning away AI demand. He tells Ben Horowitz and Erik Torenberg why AWS could become a trillion-dollar run-rate business, and why inference cost, custom chips, and smaller teams matter more than squeezing old customers.
56:49ENAlfred Lin on Building in the AI Era: The Diffusion Gap, Founder Conviction, and Fire and IceAlfred Lin, Jason Zhang, Tanvir Bhathal · Sequoia CapitalAt Stanford AI Club, Sequoia’s Alfred Lin explains where he sees opportunity in AI and why learning, human understanding, and operating discipline still shape enduring companies.
1:20:28ENAI Valuations, Talent Wars and the Venture Capital Tradeoffs Behind ThemGast: Jack Altman, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jack Altman, Jason Lemkin and Rory O’Driscoll debate large early-stage bets, open-weight models and the changing market for exits.
1:19:28ENAI Safety, Personal Agents and the Venture Market’s Uneven ExitsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate oversight of advanced AI, the economics of personal assistants and what a weaker software exit market means for investors.
1:26:43EN20VC: AI Funding, Model Competition and the Economics of AgentsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate capital intensity, AI company economics and where agents may create value.
1:17:47EN20VC: AI Acquisitions, Model Costs and Software ValuationsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss reported deals, frontier-model economics and the challenges of valuing software in a fast-changing market.
1:23:34EN20VC on Enterprise Sales Hiring, Compensation and AIGast: Chad Peets, Chris Degnan · Moderation: Harry StebbingsChad Peets and Chris Degnan discuss building sales teams, forecasting revenue and competing for talent while AI changes enterprise markets.
1:23:12ENVenture Returns, OpenAI Litigation and the Economics of AI GrowthGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate public software prices, research talent, AI advertising and late-stage venture valuations.
1:32:50ENKaz Nejatian on Opendoor, AI Financing and the Cost of GrowthGast: Kaz Nejatian, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsOpendoor’s new CEO explains his housing strategy; Harry Stebbings and investors examine AI infrastructure commitments, software margins and the return of IPOs.
1:14:45ENAnthropic, Statsig and the Economics of AI Growth: Cliff Obrecht and 20VCGast: Cliff Obrecht, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsCanva’s Cliff Obrecht joins Harry Stebbings and investors to discuss AI financing, employee liquidity and the real cost of putting models into software.
1:34:20ENGPT-5, Palantir and the Economics of AI GrowthGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI competition, the price of growth and what leaner companies could mean for workers.
1:28:36ENFigma’s IPO, Executive Pay and the Price of AI GrowthGast: Brian Halligan, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHubSpot co-founder Brian Halligan joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to unpack IPO pricing, public ownership and venture strategy.
1:28:12ENApple, Google and the Race to Fund AI GrowthGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate venture-fund scale, AI infrastructure and how large technology companies can respond to new competition.
1:09:30ENChime’s IPO, Scale AI’s Deal and the Return of Public-Market LiquidityGast: Rory O’Driscoll, Jason Lemkin, Garrett · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll, Jason Lemkin and Garrett from Handshake discuss AI suppliers, venture exits and the IPO market in June 2025.
1:19:24ENOpenAI’s Jony Ive Deal, YC’s Scale and the Math Behind Venture ReturnsGast: Rory O’Driscoll, Jason Lemkin · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate hardware, IPO terms, dilution and the changing economics of venture investing.
1:19:32ENBenchmark, a16z and the Math of Venture Capital in the AI EraGast: Rory O’Driscoll, Jason Lemkin · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate stage focus, large funds and how AI could reshape software and employment.
34:07ENOla Källenius on Mercedes-Benz’s Next Transformation: EVs, AI, and Modern LuxuryGast: Ola Källenius · Moderation: 张小珺Mercedes-Benz CEO Ola Källenius describes a century-scale shift driven by zero-emission powertrains, software, and AI. He explains why the company is expanding electric models while protecting the craftsmanship, safety, and desirability that define its luxury position.
1:35:02ENa16z, Founders Fund and the Risks Behind Venture’s Biggest FundsGast: Rory O’Driscoll, Jason Lemkin · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate fund size, late-stage returns, AI uncertainty and delayed liquidity.
44:53ENKeith Rabois and Eric Glyman on Ramp, Execution and Building MomentumGast: Keith Rabois, Eric Glyman · Moderation: Harry StebbingsThe investor and Ramp CEO explain business equations, time audits and management practices, while discussing the company’s finance automation ambitions.
1:00:45ENChristian Hecker and Johan Brenner on Trade Republic’s Fundraising and GrowthGast: Christian Hecker, Johan Brenner · Moderation: Harry StebbingsThe founder and investor discuss early financing, customer acquisition, board relationships and their long-term savings thesis.
1:23:43ENThomas Plantenga and Alex Taussig on Vinted’s Turnaround and Marketplace GrowthGast: Thomas Plantenga, Alex Taussig · Moderation: Harry StebbingsThe Vinted CEO and Lightspeed investor discuss pricing, cross-border expansion, acquisition economics and the limits of simple metrics.
1:06:44ENKeith Rabois and Mike Shebat on Work Ethic, Startup Culture and Founder JudgmentGast: Keith Rabois, Mike Shebat · Moderation: Harry StebbingsThe investor and Traba CEO discuss demanding schedules, hiring, advice and the trade-offs behind building an ambitious company.
57:16ENJack Altman, Auren Hoffman and Jason Lemkin Debate Founder-Led Venture FundsGast: Jack Altman, Auren Hoffman, Jason Lemkin · Moderation: Harry StebbingsThe operators and investors discuss founder advice, limited-partner obligations, time trade-offs and whether their model can scale.
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