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1:35:32ENSpaceX Valuations, Harvey’s Growth and the Risks Behind AI DealsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll examine private-market prices, a proposed media deal, AI applications and fintech competition.
1:11:42ENEventbrite, Databricks and the Search for Durable Software GrowthGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate software-market limits, AI pricing and what makes a venture investment last.
1:32:23ENAnthropic’s Financing, NVIDIA’s Chip Risks and the Enterprise AI RaceGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss infrastructure commitments, customer-support software, AI marketing and IPO valuations.
1:18:29ENBase44 Founder Maor Shlomo on AI App Building and CompetitionGuest Maor Shlomo · Host Harry StebbingsShlomo explains why he joined Wix, how he thinks about app-builder defensibility and why the future of software remains contested.
1:26:40ENAI Coding Valuations, NVIDIA Risk and the Future of Private MarketsGuest Tomasz Tunguz, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Tomasz Tunguz, Jason Lemkin and Rory O’Driscoll debate coding tools, infrastructure risk, venture financing and secondary liquidity.
1:17:11ENAI Defensibility, Venture Risk and the Difficulty of Timing a ShortGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate fast-moving AI markets, investment risk and how founders approach fundraising.
1:18:47ENNavan’s IPO, Harvey’s Valuation and the New Economics of VentureGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss liquidity, AI software growth, public-market competition and board oversight.
1:34:12ENThe Venture Capital Cycle: AI Markets, Compute and the Cost of Moving Too FastGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll join Harry Stebbings to debate AI market size, infrastructure spending and how venture investors can survive a boom.
1:24:58ENAI Burn Multiples, Infrastructure Financing and the Venture MarketGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll join Harry Stebbings to debate funding, energy demand and the risks behind rapid AI growth.
1:34:12ENOpenAI Secondaries, Ramp and the Price of AI GrowthGuest Jason Lemkin, Rory O’Driscoll, Jeff Lawson · Host Harry StebbingsJason Lemkin, Rory O’Driscoll and Jeff Lawson join Harry Stebbings to debate AI funding, founder incentives and the risks of moving too fast.
1:14:44ENMarc Benioff on Enterprise AI, Anthropic’s Funding and Klarna’s IPOGuest Marc Benioff, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsThe Salesforce CEO joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to discuss AI agents, software growth and the economics of today’s venture market.
1:23:11ENBessemer’s Byron Deeter on AI Growth, Venture Scale and LiquidityGuest Byron Deeter · Host Harry StebbingsDeeter discusses AI software economics, follow-on investments and the trade-offs facing venture firms and their limited partners.
1:28:36ENFigma’s IPO, Executive Pay and the Price of AI GrowthGuest Brian Halligan, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHubSpot co-founder Brian Halligan joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to unpack IPO pricing, public ownership and venture strategy.
1:15:40ENFigma’s IPO Filing, Melio’s Sale and the Pressure on Software InvestorsGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin examine software valuations, venture returns and the AI market’s changing economics.
59:27ENAaron Levie on AI Agents, Jobs and the Future of Enterprise SoftwareMatthew Berman, Aaron Levie · Forward FutureBox’s CEO explains his AI-first strategy, why he expects demand to grow and how humans may direct and review agents.
1:16:16ENNavan, Canva and the AI Investment BoomGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll join Harry Stebbings to debate AI talent, legal software, public listings and enterprise platforms.
1:22:59ENCircle’s IPO, Anduril’s Funding and the AI Budget DebateGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin discuss public listings, venture concentration and the outlook for software and Musk’s companies.
1:27:13ENSam Lessin, Jason Lemkin and Rory O’Driscoll Debate DPI and the Future of VentureGuest Sam Lessin, Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsThe investors examine cash distributions versus paper marks, fund size, AI spending and the changing economics of startup investing.
1:19:29ENChime’s Planned IPO, Venture Liquidity and the Rippling–Deel DisputeGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin discuss late-stage financing, contested litigation and AI software competition.
1:20:13ENStartup Funding, OpenAI and AI Competition: A Venture Investor RoundtableGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss financing, FTX-related investments, AI business models and the future of work.
1:28:17ENSeries A and B Investing in an AI Market: Risk, Liquidity and TimingGuest Rory O’Driscoll, Jason Lemkin, Fabrice Grinda · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll, Jason Lemkin and Fabrice Grinda debate returns, fund strategy and competition in a fast-changing market.
1:26:55ENVenture Liquidity, Endowments and AI Investing in 2025Guest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin discuss private-market liquidity, fund construction and the economics of AI businesses.
1:07:38ENAman Narang on Building Toast: Speed, Focus and Scaling a Restaurant PlatformGuest Aman Narang · Host Harry StebbingsThe Toast co-founder explains how the company pivoted to point of sale, learned to scale its team and expanded into payments and lending.
1:05:48ENKaz Nejatian on Shopify: Building Complete Products and a Company for the Long TermGuest Kaz Nejatian · Host Harry StebbingsShopify’s COO explains its product culture, internal tools and partnerships, and reflects on remote work, information flow and leadership.
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