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1:18:23EN20VC on AI Security, Software Deals and the Economics of ComputeGast: Nikesh Arora, Jason Lemkin, Rory O’Driscoll · Moderation: 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.
1:12:41ENAI Security, Revenue Claims and Wearable Economics: A 20VC Investor RoundtableGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI product strategy, security spending, startup valuations and the durability of consumer subscriptions. Their discussion includes reported developments and unverified estimates, as well as O’Driscoll’s disclosure of an indirect Oura investment.
58:26ENGili Raanan on Venture Entry Prices, Growth and Private-Market LiquidityGast: Gili Raanan · Moderation: Harry StebbingsThe Cyberstarts founder explains his approach to cybersecurity investing, when he discusses margins and why secondary sales can help employees and limited partners.
57:04ENMatthew Steckman on Anduril’s Defense Business, Procurement and Product BetsGast: Matthew Steckman · Moderation: Harry StebbingsAnduril’s president explains a $20 billion procurement ceiling, the company’s approach to building military products and his view of the responsibilities of defense suppliers. His forecasts and company claims reflect his position as an interested executive.
49:33ENShardul Shah on Venture Conviction, Outliers and Decisions at IndexGast: Shardul Shah · Moderation: Harry StebbingsThe Index Ventures partner explains how he evaluates founders, revisits follow-on investments and works through disagreement.
50:15ENJason Lemkin on Wiz, CrowdStrike and the SaaS Liquidity CrunchGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder discusses a reported acquisition approach, a major outage and the economics of legal-tech and venture exits.
54:32ENNikesh Arora on Competition, Acquisitions and Leading Through ChangeGast: Nikesh Arora · Moderation: Harry StebbingsThe Palo Alto Networks CEO discusses product advantages, acquisition discipline, communication and the personal tradeoffs of leadership.
1:09:17ENGili Raanan on Seed Investing, Founder Selection and Cyberstarts’ Sunrise ProcessGast: Gili Raanan · Moderation: Harry StebbingsThe Cyberstarts founder explains his focus on teams, structured customer discovery and building cybersecurity companies.
1:18:41ENGuy Podjarny on Snyk, Product-Market Fit and Building Durable AdvantageGast: Guy Podjarny · Moderation: Harry StebbingsThe Snyk founder and angel investor explains how to reason about future markets, focus messaging and learn through iteration.









