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TopicEnterprise AIPersonHarry StebbingsLengthOver 30 min
1:19:50EN
20VC with Harry Stebbings· Oct 19, 2026Podcast · 2 speakersSameer Dholakia on AI Investing, Bessemer's Growth Strategy and Company CultureGuest Sameer Dholakia · Host Harry StebbingsThe Bessemer partner explains his approach to pricing fast-growing AI companies, backing founders and building teams, while discussing the risks behind his optimistic forecasts.Venture CapitalAI StrategyLeadership+2
58:54EN
20VC with Harry Stebbings· Oct 12, 2026Podcast · 2 speakersMike Cannon-Brookes on AI Agents, Enterprise Context and the Future of InterfacesGuest Mike Cannon-Brookes · Host Harry StebbingsAtlassian's CEO argues that agents make product design more important, explains the trade-offs in enterprise AI, and makes the case for slower thinking.AI interface designEnterprise AIAI agents+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
1:19:04EN
20VC with Harry Stebbings· Sep 21, 2026Podcast · 2 speakersDaniel Dines on AI Agents, Enterprise Work and the Limits of AutomationGuest Daniel Dines · Host Harry StebbingsThe UiPath co-founder argues that companies need a map of work and reliable automation alongside AI, while Harry Stebbings challenges his assumptions about how fast jobs will change.Enterprise AIWorkflow automationAI agents+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
1:29:22EN
20VC with Harry Stebbings· Aug 29, 2026Podcast · 2 speakersEno Reyes on AI Model Economics, Enterprise Control and Factory's StrategyGuest Eno Reyes · Host Harry StebbingsFactory's CTO discusses cost per outcome, model routing, open models, enterprise hiring and his expectations for the AI market.Agent engineeringEnterprise AIAI cost & performance+2
1:28:28EN
20VC with Harry Stebbings· Aug 24, 2026Podcast · 2 speakersJulien Bek on Sequoia’s Investment Process, Founder Judgment and AI MarketsGuest Julien Bek · Host Harry StebbingsThe Sequoia partner explains how he develops conviction, evaluates founders and thinks about a market where AI agents may become customers.Venture CapitalCompany BuildingAI agents+2
1:10:08EN
20VC with Harry Stebbings· Aug 22, 2026Podcast · 2 speakersJerry Murdock on AI Financing, Open Models and Technology CyclesGuest Jerry Murdock · Host Harry StebbingsInsight Partners' co-founder discusses credit risk, specialized models, security and how investors might navigate an uncertain AI cycle.Venture CapitalAI cost & performanceEnterprise AI+2
1:09:44EN
20VC with Harry Stebbings· Aug 17, 2026Podcast · 2 speakersAndrew Macdonald on Uber’s Membership Strategy, Autonomy and AIGuest Andrew Macdonald · Host Harry StebbingsUber’s president and COO discusses marketplace incentives, autonomous vehicles, the company’s China exit and the challenge of measuring AI’s value.MarketplacesProduct StrategyAutonomous Driving+2
1:08:25EN
20VC with Harry Stebbings· Aug 10, 2026Podcast · 2 speakersAlex Atallah on OpenRouter, Model Competition and AI MarketplacesGuest Alex Atallah · Host Harry StebbingsThe OpenRouter CEO discusses inference providers, open-weight models, enterprise safety and the economics of routing.Model routing & gatewaysInferenceOpen-weight models+2
1:09:26EN
20VC with Harry Stebbings· Aug 3, 2026Podcast · 2 speakersAnastasios Angelopoulos on Arena, Open Models and AI EvaluationGuest Anastasios Angelopoulos · Host Harry StebbingsArena’s CEO discusses real-world model comparisons, enterprise AI control, security and the economics of evaluation.EvalsOpen-weight modelsEnterprise AI+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
1:06:45EN
20VC with Harry Stebbings· Jul 27, 2026Podcast · 2 speakersMatt Murphy on Anthropic, Open Models and the New Venture PlaybookGuest Matt Murphy · Host Harry StebbingsThe Menlo Ventures partner explains his investments in Anthropic, Lovable and Legora, and debates AI margins, model competition and venture fund strategy.Venture CapitalAI StrategyInvesting+2
1:02:42EN
20VC with Harry Stebbings· Jul 25, 2026Podcast · 2 speakersMercor’s Osvald Nitski on AI Training Data, Product and Customer ConcentrationGuest Osvald Nitski · Host Harry StebbingsMercor’s head of product discusses how the company supplies expert data to AI labs, designs its marketplace and plans to reach more enterprise customers.Data quality & curationProduct ManagementEnterprise AI+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
1:00:08EN
20VC with Harry Stebbings· Jul 11, 2026Podcast · 2 speakersArvind Jain on Enterprise AI, Open Models and the Future of WorkGuest Arvind Jain · Host Harry StebbingsThe Glean founder debates model competition, enterprise AI returns and whether productivity gains will shrink teams or raise the bar for everyone.Enterprise AIAI agentsOpen-weight models+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
1:11:53EN
20VC with Harry Stebbings· Jul 4, 2026Podcast · 2 speakersSierra Co-founder Clay Bavor on Open Models, Enterprise AI and Building TeamsGuest Clay Bavor · Host Harry StebbingsBavor discusses model selection and compute costs, deploying AI agents for enterprises, and how Sierra approaches hiring and company culture.Enterprise AIOpen-weight modelsAI agents+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
1:16:37EN
20VC with Harry Stebbings· Jun 22, 2026Podcast · 2 speakersNikesh Arora on Enterprise AI, Cybersecurity and Model EconomicsGuest Nikesh Arora · Host Harry StebbingsPalo Alto Networks’ CEO discusses model depth, token costs, security and how leaders can adapt large organizations.Enterprise AIAI securityAI cost & performance+2
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