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1:19:50ENSameer Dholakia on AI Investing, Bessemer's Growth Strategy and Company CultureGast: Sameer Dholakia · Moderation: 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.
58:54ENMike Cannon-Brookes on AI Agents, Enterprise Context and the Future of InterfacesGast: Mike Cannon-Brookes · Moderation: 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.
1:15:51ENThe AI Race, Founder Loyalty and the New Rules of Enterprise SoftwareGast: Dev Ittycheria, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Dev Ittycheria, Jason Lemkin and Rory O’Driscoll debate model competition, startup exits and what happens when AI agents choose vendors.
1:20:43ENAI Agents, Venture Pricing and the Tradeoffs Behind the Funding BoomGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI products, high-priced venture rounds, enterprise software and infrastructure risk.
1:19:04ENDaniel Dines on AI Agents, Enterprise Work and the Limits of AutomationGast: Daniel Dines · Moderation: 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.
1:22:31ENAI Assistants, Enterprise Adoption and the Venture Market’s New RisksGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate personal agents, legal AI, autonomous vehicles and the economics of financing AI companies.
1:20:29ENAI Compute, Agent Security and the Race to Build More SoftwareGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss chip demand, personal agents, software competition and how AI may change enterprise buying.
1:29:22ENEno Reyes on AI Model Economics, Enterprise Control and Factory's StrategyGast: Eno Reyes · Moderation: Harry StebbingsFactory's CTO discusses cost per outcome, model routing, open models, enterprise hiring and his expectations for the AI market.
1:28:28ENJulien Bek on Sequoia’s Investment Process, Founder Judgment and AI MarketsGast: Julien Bek · Moderation: Harry StebbingsThe Sequoia partner explains how he develops conviction, evaluates founders and thinks about a market where AI agents may become customers.
1:10:08ENJerry Murdock on AI Financing, Open Models and Technology CyclesGast: Jerry Murdock · Moderation: Harry StebbingsInsight Partners' co-founder discusses credit risk, specialized models, security and how investors might navigate an uncertain AI cycle.
1:09:44ENAndrew Macdonald on Uber’s Membership Strategy, Autonomy and AIGast: Andrew Macdonald · Moderation: Harry StebbingsUber’s president and COO discusses marketplace incentives, autonomous vehicles, the company’s China exit and the challenge of measuring AI’s value.
1:08:25ENAlex Atallah on OpenRouter, Model Competition and AI MarketplacesGast: Alex Atallah · Moderation: Harry StebbingsThe OpenRouter CEO discusses inference providers, open-weight models, enterprise safety and the economics of routing.
1:09:26ENAnastasios Angelopoulos on Arena, Open Models and AI EvaluationGast: Anastasios Angelopoulos · Moderation: Harry StebbingsArena’s CEO discusses real-world model comparisons, enterprise AI control, security and the economics of evaluation.
1:20:22EN20VC Roundtable on Open Weights, AI Spending and Software InvestingGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI safety, chip investment, enterprise budgets and the future of software.
1:06:45ENMatt Murphy on Anthropic, Open Models and the New Venture PlaybookGast: Matt Murphy · Moderation: Harry StebbingsThe Menlo Ventures partner explains his investments in Anthropic, Lovable and Legora, and debates AI margins, model competition and venture fund strategy.
1:02:42ENMercor’s Osvald Nitski on AI Training Data, Product and Customer ConcentrationGast: Osvald Nitski · Moderation: 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.
1:27:39EN20VC Roundtable on Open Models, AI Economics and Payments DealsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss model security, inference investment and a reported PayPal proposal.
1:26:12EN20VC Roundtable on AI Competition, Enterprise Spending and Venture CapitalGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss a reported Apple lawsuit, AI pricing, memory markets and venture financing.
1:00:08ENArvind Jain on Enterprise AI, Open Models and the Future of WorkGast: Arvind Jain · Moderation: Harry StebbingsThe Glean founder debates model competition, enterprise AI returns and whether productivity gains will shrink teams or raise the bar for everyone.
1:27:05EN20VC on AI Regulation, Compute Economics and Enterprise AdoptionGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported AI policy proposals, infrastructure spending, software deployment and startup liquidity.
1:11:53ENSierra Co-founder Clay Bavor on Open Models, Enterprise AI and Building TeamsGast: Clay Bavor · Moderation: Harry StebbingsBavor discusses model selection and compute costs, deploying AI agents for enterprises, and how Sierra approaches hiring and company culture.
1:18:07EN20VC Roundtable: AI Spending, Model Competition and Software AcquisitionsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate enterprise AI returns, prediction markets, SaaS roll-ups and the cost of raising capital.
1:28:02EN20VC Roundtable: Open Models, AI Spending and the Cost of CompetitionGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI talent, model economics, consulting and whether labs should build their own chips.
1:16:37ENNikesh Arora on Enterprise AI, Cybersecurity and Model EconomicsGast: Nikesh Arora · Moderation: Harry StebbingsPalo Alto Networks’ CEO discusses model depth, token costs, security and how leaders can adapt large organizations.
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