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1:35:32ENSpaceX Valuations, Harvey’s Growth and the Risks Behind AI DealsInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 GrowthInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 RaceInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 CompetitionInvité : Maor Shlomo · Anime : 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 MarketsInvité : Tomasz Tunguz, Jason Lemkin, Rory O’Driscoll · Anime : 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 ShortInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 VentureInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 FastInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 MarketInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 GrowthInvité : Jason Lemkin, Rory O’Driscoll, Jeff Lawson · Anime : 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 IPOInvité : Marc Benioff, Jason Lemkin, Rory O’Driscoll · Anime : 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 LiquidityInvité : Byron Deeter · Anime : 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 GrowthInvité : Brian Halligan, Jason Lemkin, Rory O’Driscoll · Anime : 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 InvestorsInvité : Rory O’Driscoll, Jason Lemkin · Anime : 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 BoomInvité : Jason Lemkin, Rory O’Driscoll · Anime : 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 DebateInvité : Rory O’Driscoll, Jason Lemkin · Anime : 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 VentureInvité : Sam Lessin, Rory O’Driscoll, Jason Lemkin · Anime : 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 DisputeInvité : Rory O’Driscoll, Jason Lemkin · Anime : 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 RoundtableInvité : Rory O’Driscoll, Jason Lemkin · Anime : 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 TimingInvité : Rory O’Driscoll, Jason Lemkin, Fabrice Grinda · Anime : 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 2025Invité : Rory O’Driscoll, Jason Lemkin · Anime : 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 PlatformInvité : Aman Narang · Anime : 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 TermInvité : Kaz Nejatian · Anime : 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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