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59:41EN
20VC with Harry Stebbings· Oct 22, 2026Podcast · 3 speakers20VC: Venture Fund Size, AI Valuations and the Changing Software MarketGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O'Driscoll debate venture concentration, infrastructure risk, code review and the assumptions behind fast-growing AI companies.
1:17:09EN20VC with Harry Stebbings· Oct 15, 2026Podcast · 3 speakers20VC on Pro Rata Rights, AI Pricing and the Changing Software MarketGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate investor rights, model economics and the choices facing software companies and their employees.
1:19:28EN20VC with Harry Stebbings· Sep 17, 2026Podcast · 3 speakersAI Safety, Personal Agents and the Venture Market’s Uneven ExitsGuest Jason Lemkin, Rory O’Driscoll · Host 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.
1:29:42EN20VC with Harry Stebbings· Aug 13, 2026Podcast · 3 speakers20VC on AI Competition, Founder Control and Software ValuationsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate how AI is reshaping software markets, talent, infrastructure and investor incentives.
1:30:48EN20VC with Harry Stebbings· Aug 8, 2026Podcast · 2 speakersDavid Frankel on Seed Investing, AI Winners and the Value of PatienceGuest David Frankel · Host Harry StebbingsFounder Collective’s co-founder debates fund size, valuations and exits with Harry Stebbings, and explains why he expects both transformative AI companies and heavy losses.
1:18:23EN20VC with Harry Stebbings· Aug 6, 2026Podcast · 4 speakers20VC on AI Security, Software Deals and the Economics of ComputeGuest Nikesh Arora, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsNikesh Arora joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to debate software acquisitions, AI security and the infrastructure needed to deploy models.
1:04:36EN20VC with Harry Stebbings· Jul 13, 2026Podcast · 2 speakersWix CEO Avishai Abrahami on Base44, AI and Building for Small BusinessesGuest Avishai Abrahami · Host Harry StebbingsThe Wix co-founder discusses AI-assisted application building, software economics, customer support and leadership through market uncertainty.
1:18:07EN20VC with Harry Stebbings· Jul 2, 2026Podcast · 3 speakers20VC Roundtable: AI Spending, Model Competition and Software AcquisitionsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate enterprise AI returns, prediction markets, SaaS roll-ups and the cost of raising capital.
1:28:19EN20VC with Harry Stebbings· Apr 30, 2026Podcast · 3 speakersAI Compute, Private Equity and the Narrowing Exit: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate reported AI financing, software’s future and what private-equity losses could mean for venture investors.
1:19:18EN20VC with Harry Stebbings· Mar 26, 2026Podcast · 3 speakersSeries A Fund Math, SpaceX Ambitions and the AI Valuation DebateGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll examine AI competition, speculative space infrastructure and the rising cost of venture investing.
1:04:15EN20VC with Harry Stebbings· Mar 7, 2026Podcast · 2 speakersMitchell Green on Software Stocks, Venture Liquidity and Investing Through AI ChangeGuest Mitchell Green · Host Harry StebbingsThe Lead Edge founder explains his approach to buying, selling and assessing retention while debating AI disruption and venture-fund economics.
1:14:16EN20VC with Harry Stebbings· Mar 2, 2026Podcast · 2 speakersEran Zinman on Monday.com’s AI Pivot, Pricing and Software MarketsGuest Eran Zinman · Host Harry StebbingsThe Monday.com CEO discusses AI-built software, agent workflows, sales automation and leading a public company through a difficult market.
1:06:37EN20VC with Harry Stebbings· Feb 23, 2026Podcast · 2 speakersLucas Swisher on AI Growth Investing, Fund Size and the Price of ScaleGuest Lucas Swisher · Host Harry StebbingsThe Coatue growth investor discusses software valuations, concentrated funds, AI economics and the judgment behind follow-on investments.
1:37:01EN20VC with Harry Stebbings· Feb 19, 2026Podcast · 3 speakersAnthropic, OpenClaw and Software Valuations: A 20VC Investor RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate the concentration of AI capital, the pressure on software companies and the risks of autonomous agents.
1:29:46EN20VC with Harry Stebbings· Feb 16, 2026Podcast · 2 speakersKlarna CEO Sebastian Siemiatkowski on AI, Software and the Future of BankingGuest Sebastian Siemiatkowski · Host Harry StebbingsThe Klarna cofounder explains his predictions about software switching costs, customer service and a digital financial assistant, while discussing the pressures of building a public company.
1:24:39EN20VC with Harry Stebbings· Feb 12, 2026Podcast · 4 speakersMike Cannon-Brookes and 20VC on AI, Software Markets and LeadershipGuest Mike Cannon-Brookes, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsThe Atlassian co-founder joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to debate AI spending, legal and support software, advertising and the demands on founders. Their financial figures and forecasts are claims or estimates, not independently verified results.
1:20:02EN20VC with Harry Stebbings· Feb 9, 2026Podcast · 2 speakersAnish Acharya on AI Software, Investment Judgment and the Limits of AutomationGuest Anish Acharya · Host Harry StebbingsThe a16z investor discusses incumbent software, agent products, pricing, margins and the choices founders face in a fast-moving market.
1:37:14EN20VC with Harry Stebbings· Feb 5, 2026Podcast · 3 speakersSoftware Stocks, AI Financing and Autonomous Agents: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss software valuations, infrastructure financing, autonomous driving and the risks of networked agents.
1:18:04EN20VC with Harry Stebbings· Jan 29, 2026Podcast · 3 speakersBrex, AI Inference Costs and the IPO Market: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported deals, AI economics and public-market exits. Their valuations, financial figures and predictions are estimates or reported claims, not independently verified results.
1:13:37EN
Lenny's PodcastPodcast · 2 speakersTen Hot Takes From a Bootstrapped SaaS Founder: Pricing, Retention, Tempo and the Middle of the FunnelGuest Patrick Campbell · Host Lenny RachitskyPatrick Campbell, who sold ProfitWell for more than $200 million without outside funding, runs through ten operating topics, from team culture and bootstrapping to pricing, churn and freemium.
1:06:47ENLenny's PodcastPodcastStop Pushing Customers Through a Funnel: Georgiana Laudi's Customer-Led Growth PlaybookHost Lenny RachitskyHow to replace pirate metrics with customer research, jobs-to-be-done, measurable value milestones, and messaging that actually converts.