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20VC with Harry Stebbings· Oct 26, 2026Podcast · 2 speakersSatya Nadella on Zero Trust for AI and Why Every Company Should Own Its IntelligenceGuest Satya Nadella · Host Harry StebbingsThe Microsoft CEO argues that capable agents need security boundaries even as alignment research remains unsettled, and explains why firms should retain the value created by their own AI use.
1:19:50EN20VC 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.
58:54EN20VC 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.
1:19:04EN20VC 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.
1:29:22EN20VC 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.
1:28:28EN20VC 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.
1:10:08EN20VC 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.
1:09:44EN20VC 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.
1:08:25EN20VC 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.
1:09:26EN20VC 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.
1:06:45EN20VC 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.
1:02:42EN20VC 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.
1:00:08EN20VC 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.
1:11:53EN20VC 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.
1:16:37EN20VC 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.
1:25:00EN20VC with Harry Stebbings· Jun 13, 2026Podcast · 2 speakersMatan Grinberg on AI Coding, Token Costs and Building FactoryGuest Matan Grinberg · Host Harry StebbingsFactory’s CEO discusses enterprise AI budgets, model choice, engineering culture and the uncertain effects of automation on work.
1:14:30EN20VC with Harry Stebbings· Jun 8, 2026Podcast · 2 speakersRoman Chernin on AI Compute Demand, Inference and InfrastructureGuest Roman Chernin · Host Harry StebbingsNebius’s co-founder discusses customer demand, GPU economics, managed inference and the risks of a concentrated market.
57:42EN20VC with Harry Stebbings· Jun 6, 2026Podcast · 2 speakersJacob Lauritzen on AI Engineering, Legal Work and Building LegoraGuest Jacob Lauritzen · Host Harry StebbingsLegora’s CTO discusses code review, token budgets, enterprise adoption and how legal workflows might change.
1:13:48EN20VC with Harry Stebbings· May 11, 2026Podcast · 2 speakersPatrick Forquer on Selling Legal AI and Scaling Legora’s Revenue TeamGuest Patrick Forquer · Host Harry StebbingsLegora’s chief revenue officer explains how his team runs pilots, trains salespeople and forecasts rapid growth, and shares company-reported performance figures.
54:54EN20VC with Harry Stebbings· Apr 20, 2026Podcast · 2 speakersAaron Levie on Enterprise AI, Software Value and the Future of WorkGuest Aaron Levie · Host Harry StebbingsThe Box CEO discusses how agents could reshape enterprise workflows, token budgets and software markets while humans remain involved.
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.
1:00:33EN20VC with Harry Stebbings· Feb 28, 2026Podcast · 2 speakersJerry Murdock on Autonomous Agents, Software Investing and Adapting to ChangeGuest Jerry Murdock · Host Harry StebbingsThe Insight Partners co-founder discusses agent infrastructure, investment judgment, employment and lessons from previous technology cycles.
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.Load moreShowing 24 of 48