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1:27:39EN
20VC with Harry Stebbings· Jul 23, 2026Podcast · 3 speakers20VC Roundtable on Open Models, AI Economics and Payments DealsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss model security, inference investment and a reported PayPal proposal.
1:26:12EN20VC with Harry Stebbings· Jul 16, 2026Podcast · 3 speakers20VC Roundtable on AI Competition, Enterprise Spending and Venture CapitalGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss a reported Apple lawsuit, AI pricing, memory markets and venture financing.
1:17:01EN20VC with Harry Stebbings· Oct 20, 2025Podcast · 2 speakersDeel CEO Alex Bouaziz on Fundraising, Acquisitions and Global PayrollGuest Alex Bouaziz · Host Harry StebbingsBouaziz discusses Deel’s financing, hands-on leadership, acquisition playbook and the company’s ambitions amid a dispute with Rippling.
51:06EN20VC with Harry Stebbings· Jul 18, 2025Podcast · 2 speakersScott Wu on Cognition's Windsurf Deal and the Future of AI CodingGuest Scott Wu · Host Harry StebbingsThe Cognition CEO explains the fast-moving acquisition, the role of AI agents in engineering, and his predictions for software development.
1:22:54EN20VC with Harry Stebbings· Jul 17, 2025Podcast · 3 speakersWindsurf, Google and Cognition: A Deal Breakdown and the AI Coding MarketGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin discuss a complex set of transactions, AI coding tools, retention and model competition.
1:12:57EN20VC with Harry Stebbings· Jul 10, 2025Podcast · 3 speakersMeta’s AI Talent Drive, Microsoft Layoffs and the Economics of Startup GrowthGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin examine talent competition, stock compensation, acquisitions and the changing market for venture-backed companies.
1:15:40EN20VC 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.
1:19:29EN20VC 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.
1:26:55EN20VC 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.
1:20:50EN20VC with Harry Stebbings· Jun 3, 2024Podcast · 2 speakersJason Lemkin on SaaS Valuations, Private Equity and the Liquidity ProblemGuest Jason Lemkin · Host Harry StebbingsThe SaaStr founder discusses slowing software growth, AI budgets, venture returns and why the next exit may be harder to find.
54:32EN20VC with Harry Stebbings· May 20, 2024Podcast · 2 speakersNikesh Arora on Competition, Acquisitions and Leading Through ChangeGuest Nikesh Arora · Host Harry StebbingsThe Palo Alto Networks CEO discusses product advantages, acquisition discipline, communication and the personal tradeoffs of leadership.
59:00EN20VC with Harry Stebbings· May 1, 2024Podcast · 2 speakersMark Suster on Venture Fundraising, Liquidity and Exit PricesGuest Mark Suster · Host Harry StebbingsThe Upfront Ventures partner explains his fundraising approach, investment reserves and view of private equity as a buyer of venture-backed companies.
1:08:30EN20VC with Harry Stebbings· Apr 8, 2024Podcast · 2 speakersBastian Lehmann on Selling Postmates, Starting Again and the Future of AIGuest Bastian Lehmann · Host Harry StebbingsThe former Postmates CEO recounts the Uber stock deal, discusses his approach to investors and shares predictions about personal AI and new devices.
1:02:30EN20VC with Harry Stebbings· Mar 15, 2024Podcast · 2 speakersLuca Ferrari on Bending Spoons, Acquisitions and Learning From RiskGuest Luca Ferrari · Host Harry StebbingsThe co-founder explains how his company buys and improves established products, allocates capital and evaluates talent.
1:08:17EN20VC with Harry Stebbings· Mar 1, 2024Podcast · 2 speakersFrank Quattrone on Technology M&A, IPOs and the Amazon Pricing DebateGuest Frank Quattrone · Host Harry StebbingsThe Qatalyst founder recounts deals involving Qualtrics, LinkedIn and Amazon, and explains how markets, financing and regulation shape transactions.
1:14:40EN20VC with Harry Stebbings· Jan 10, 2024Podcast · 3 speakersEd Sim and Jamin Ball on Startup Exits, IPOs and the 2024 Funding ResetGuest Ed Sim, Jamin Ball · Host Harry StebbingsTwo investors discuss the consequences of high private valuations, founder and investor incentives, acquisition markets and the path to an IPO.
1:13:41EN20VC with Harry Stebbings· Jun 5, 2023Podcast · 2 speakersTJ Parker on Building PillPack and Selling to AmazonGuest TJ Parker · Host Harry StebbingsThe pharmacist and founder recounts the early customer-acquisition challenge, network disputes, leadership decisions and acquisition process.
48:44EN20VC with Harry Stebbings· Mar 27, 2023Podcast · 2 speakersDara Khosrowshahi on Leading Uber, Marketplace Trade-offs and Learning from MistakesGuest Dara Khosrowshahi · Host Harry StebbingsUber’s CEO discusses the move from Expedia, the company’s bets on delivery and acquisitions, and why reversible decisions deserve a different pace.