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Invest Like the Best with Patrick O'ShaughnessyAuthor: Colossus Investing & Business Podcasts
Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com Language: en Genres: Business, Investing, Technology Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App - [Invest Like the Best, EP.476]
Episode 476
Wednesday, 3 June, 2026
My guest today is Dara Khosrowshahi, the CEO of Uber. Before Uber, Dara ran Expedia for thirteen years. We start with why he took this job in 2017, and a big part of that story is Daniel Ek, who told him that life is not about happiness, it is about impact. We talk about what the chaos felt like on day one, and how his family leaving Iran when he was nine shaped the way he handles pressure today. We spend most of our time on autonomous vehicles and Uber's role as the demand aggregator in a world of physical AI. Dara explains why Uber is a supply-led company, what it will take to win, and why he expects many winners in AVs rather than one. We also discuss Uber's $10 billion in free cash flow, the push toward a single app for everything, and what he has learned from Allen & Co, Barry Diller and Reed Hastings. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at colossus.com/subscribe. ----- Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to ramp.com/invest to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ridgelineapps.com. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Timestamps: (00:00:00) Welcome to Invest Like The Best (00:02:29) Intro to Dara Khosrowshahi (00:03:37) How Daniel Ek Convinced Dara to Take the Uber Job (00:06:54) Bringing Order to Chaos (00:09:20) Managing Stress as a Leader (00:11:22) The Chip on His Shoulder (00:12:53) Parenting Lessons (00:17:01) Mandate for AI Adoption (00:21:21) Uber's Role in Physical AI (00:22:48) Winning the AV Demand Race (00:27:41) Partnering vs. Competing with Waymo (00:32:05) AV Success Unlocks New Markets (00:35:09) Why Drones Haven't Arrived Yet (00:36:27) Regional AV Rollout Differences (00:37:35) Uber Eats International Winning Formula (00:39:44) Key to Aggregating Supply Well (00:44:34) Adding Hotels to Uber Platform (00:50:46) Lessons in Marketing at Scale (00:52:59) Apps vs. AI Agents in Seven Years (00:54:08) What Dara Learned from Barry Diller (00:56:52) What Dara Learned from Allen & Co (01:00:09) Buybacks vs. Growth Investing (01:04:17) Lessons from Reed Hastings (01:05:49) The Kindest Thing
