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1:00:39EN
a16z· Oct 23, 2026Podcast · 3 speakersAmazon CEO Andy Jassy on the $220 Billion AI BuildoutGuest Andy Jassy · Host Ben Horowitz, Erik TorenbergEven at roughly $220 billion of 2026 CapEx, Jassy says Amazon is still turning away AI demand. He tells Ben Horowitz and Erik Torenberg why AWS could become a trillion-dollar run-rate business, and why inference cost, custom chips, and smaller teams matter more than squeezing old customers.AI StrategyInfrastructure & deploymentSemiconductors+2
1:15:51EN
20VC with Harry Stebbings· Oct 8, 2026Podcast · 4 speakersThe AI Race, Founder Loyalty and the New Rules of Enterprise SoftwareGuest Dev Ittycheria, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Dev Ittycheria, Jason Lemkin and Rory O’Driscoll debate model competition, startup exits and what happens when AI agents choose vendors.Enterprise AIFoundation ModelsStartups+2
1:20:43EN
20VC with Harry Stebbings· Sep 24, 2026Podcast · 3 speakersAI Agents, Venture Pricing and the Tradeoffs Behind the Funding BoomGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI products, high-priced venture rounds, enterprise software and infrastructure risk.Venture CapitalAI agentsEnterprise AI+2
1:22:31EN
20VC with Harry Stebbings· Sep 10, 2026Podcast · 3 speakersAI Assistants, Enterprise Adoption and the Venture Market’s New RisksGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate personal agents, legal AI, autonomous vehicles and the economics of financing AI companies.AI agentsEnterprise AIAI Safety+2
1:20:29EN
20VC with Harry Stebbings· Sep 3, 2026Podcast · 3 speakersAI Compute, Agent Security and the Race to Build More SoftwareGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss chip demand, personal agents, software competition and how AI may change enterprise buying.AI agentsInferenceAI security+2
1:20:22EN
20VC with Harry Stebbings· Jul 30, 2026Podcast · 3 speakers20VC Roundtable on Open Weights, AI Spending and Software InvestingGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI safety, chip investment, enterprise budgets and the future of software.Open-weight modelsAI SafetyInference+2
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.Open-weight modelsEnterprise AIInference+2
1:26:12EN
20VC 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.Enterprise AIAI cost & performanceVenture Capital+2
1:27:05EN
20VC with Harry Stebbings· Jul 9, 2026Podcast · 3 speakers20VC on AI Regulation, Compute Economics and Enterprise AdoptionGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported AI policy proposals, infrastructure spending, software deployment and startup liquidity.AI StrategyVenture CapitalEnterprise AI+2
1:18:07EN
20VC 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.AI cost & performanceVenture CapitalEnterprise AI+2
1:28:02EN
20VC with Harry Stebbings· Jun 25, 2026Podcast · 3 speakers20VC Roundtable: Open Models, AI Spending and the Cost of CompetitionGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI talent, model economics, consulting and whether labs should build their own chips.AI cost & performanceOpen-weight modelsVenture Capital+2
1:28:10EN
20VC with Harry Stebbings· Jun 18, 2026Podcast · 3 speakers20VC Roundtable: AI Policy, Software Valuations and RoboticsGuest Rory O’Driscoll, Everett Randle · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Everett Randle debate reported AI restrictions, enterprise software competition and the practical challenges of robotics.AI RegulationVenture CapitalEnterprise AI+2
1:27:44EN
20VC with Harry Stebbings· May 28, 2026Podcast · 3 speakersAI Spending, Layoffs and IPO Speculation: Jason Lemkin and Rory O’Driscoll on the Economics of AgentsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsA 20VC roundtable examines how businesses weigh AI tokens against human work, and how investors assess infrastructure startups amid uncertain valuations and reported IPO plans.AI cost & performanceVenture CapitalEnterprise AI+2
1:27:17EN
20VC with Harry Stebbings· May 21, 2026Podcast · 3 speakersAI Funding, IPO Expectations and the Politics of Layoffs: Jason Lemkin and Rory O’DriscollGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsA 20VC roundtable examines reported Anthropic financing, AI spending, software valuations, chip infrastructure and speculative IPOs, then considers the politics of job losses.Venture CapitalAI cost & performanceEnterprise AI+2
1:19:05EN
20VC with Harry Stebbings· May 14, 2026Podcast · 3 speakersAI Compute Deals, Cerebras’s IPO and the Cost of Building: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate AI infrastructure, software competition and IPO valuations, then discuss the personal demands of founding a company.Venture CapitalAI cost & performanceEnterprise AI+2
1:36:35EN
20VC with Harry Stebbings· May 7, 2026Podcast · 3 speakersAI Spending, Software Stocks and IPO Speculation: A 20VC Earnings RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll assess technology earnings, software growth and reported AI funding, then debate how leaders and workers adapt to AI.Venture CapitalAI cost & performanceEnterprise AI+2
1:28:19EN
20VC 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.Venture CapitalAI cost & performanceEnterprise AI+2
1:50:05EN
20VC with Harry Stebbings· Apr 23, 2026Podcast · 3 speakersCursor Deal Claims, AI Valuations and the Enterprise Agent Race: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll weigh a purported Cursor transaction, design software and enterprise agent infrastructure, while debating IPO and valuation risk.Venture CapitalEnterprise AIInvesting+2
1:30:31EN
20VC with Harry Stebbings· Apr 16, 2026Podcast · 3 speakersAI Security, Software Valuations and SpaceX IPO Speculation: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate AI security claims, enterprise software and the assumptions behind reported private-company valuations.Venture CapitalAI securityEnterprise AI+2
1:32:21EN
20VC with Harry Stebbings· Apr 9, 2026Podcast · 3 speakersAI Financing, Model Routing and Security Risks: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate reported OpenAI and Anthropic finances, model routing, database infrastructure and security, with attention to uncertainty and conflicts.Venture CapitalModel routing & gatewaysEnterprise AI+2
1:19:18EN
20VC 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.Venture CapitalInvestingEnterprise AI+2
1:56:33EN
Matthew Berman· Mar 14, 2026The Future Live: Agents at Work, Persistent Memory and AI for HealthMatthew Berman, Nick Wentz, Rob Seaman, Varun Vummadi, Charles Packer, Dominic King · Forward FutureMatthew Berman and Nick Wentz speak with leaders from Slack, Giga, Letta and Microsoft AI about practical uses and unresolved risks.AI agentsEnterprise AICustomer support automation+2
1:21:20EN
20VC with Harry Stebbings· Mar 12, 2026Podcast · 3 speakersAnthropic’s Pentagon Dispute, AI Infrastructure and the Venture Investors’ Market DebateGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate an unresolved government dispute, the economics of compute, junior hiring and software valuations.Venture CapitalAI StrategyFuture of Work+2
1:21:53EN
20VC with Harry Stebbings· Feb 26, 2026Podcast · 3 speakersCitrini’s Hypothetical 2028 Scenario, AI Agents and Figma: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI adoption, employment, security and software valuations, separating a hypothetical crisis scenario from their investment views.Future of WorkEnterprise AIInvesting+2
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