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1:35:32EN
20VC with Harry Stebbings· Dec 11, 2025Podcast · 3 speakersSpaceX 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.Venture CapitalInvestingAI Strategy+2
1:11:42EN
20VC with Harry Stebbings· Dec 4, 2025Podcast · 3 speakersEventbrite, 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.Venture CapitalSaaSAI Strategy+2
1:32:23EN
20VC with Harry Stebbings· Nov 27, 2025Podcast · 3 speakersAnthropic’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.AI StrategyVenture CapitalEnterprise AI+2
1:18:29EN
20VC with Harry Stebbings· Nov 24, 2025Podcast · 2 speakersBase44 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.Vibe CodingProduct StrategyAI startups & small teams+2
1:26:40EN
20VC with Harry Stebbings· Nov 20, 2025Podcast · 4 speakersAI 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.Venture CapitalInvestingCoding agents+2
1:17:11EN
20VC with Harry Stebbings· Nov 13, 2025Podcast · 3 speakersAI 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.Venture CapitalInvestingAI Strategy+2
1:18:47EN
20VC with Harry Stebbings· Nov 6, 2025Podcast · 3 speakersNavan’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.Venture CapitalInvestingEnterprise AI+2
1:34:12EN
20VC with Harry Stebbings· Oct 23, 2025Podcast · 3 speakersThe 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.Venture CapitalInvestingAI Strategy+2
1:24:58EN
20VC with Harry Stebbings· Oct 2, 2025Podcast · 3 speakersAI 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.Venture CapitalAI StrategyInvesting+2
1:34:12EN
20VC with Harry Stebbings· Sep 11, 2025Podcast · 4 speakersOpenAI 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.Venture CapitalInvestingAI Strategy+2
1:14:44EN
20VC with Harry Stebbings· Aug 28, 2025Podcast · 4 speakersMarc 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.Venture CapitalEnterprise AIAnthropic+2
1:23:11EN
20VC with Harry Stebbings· Aug 25, 2025Podcast · 2 speakersBessemer’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.Venture CapitalSaaSAI Strategy+2
1:28:36EN
20VC with Harry Stebbings· Aug 7, 2025Podcast · 4 speakersFigma’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.Venture CapitalInvestingCompany Building+2
1:15:40EN
20VC with Harry Stebbings· Jul 3, 2025Podcast · 3 speakersFigma’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.Venture CapitalAcquisition StrategySaaS+2
59:27EN
Matthew Berman· Jul 2, 2025Aaron 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.AI agentsEnterprise AIFuture of Work+2
1:16:16EN
20VC with Harry Stebbings· Jun 26, 2025Podcast · 3 speakersNavan, 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.Venture CapitalInvestingEnterprise AI+2
1:22:59EN
20VC with Harry Stebbings· Jun 12, 2025Podcast · 3 speakersCircle’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.Venture CapitalInvestingAI Strategy+2
1:27:13EN
20VC with Harry Stebbings· Jun 5, 2025Podcast · 4 speakersSam 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.Venture CapitalInvestingAI Strategy+1
1:19:29EN
20VC with Harry Stebbings· May 22, 2025Podcast · 3 speakersChime’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.Venture CapitalInvestingAcquisition Strategy+2
1:20:13EN
20VC with Harry Stebbings· May 15, 2025Podcast · 3 speakersStartup 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.Venture CapitalInvestingAI Strategy+2
1:28:17EN
20VC with Harry Stebbings· May 1, 2025Podcast · 4 speakersSeries 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.Venture CapitalInvestingAI Strategy+2
1:26:55EN
20VC with Harry Stebbings· Apr 24, 2025Podcast · 3 speakersVenture 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.Venture CapitalInvestingAI Strategy+2
1:07:38EN
20VC with Harry Stebbings· Aug 21, 2024Podcast · 2 speakersAman 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.Company BuildingProduct StrategySaaS+2
1:05:48EN
20VC with Harry Stebbings· Aug 14, 2024Podcast · 2 speakersKaz 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.Product StrategyCompany BuildingProduct Management+2
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