When Glenn Fogel joined Priceline in 2000, the business was worth a few hundred million dollars. One week later, the Nasdaq peaked, eventually sending its stock down to a dollar a share. But over 25 years later, Booking Holdings has scaled over 1000x into an over $100 billion dollar global travel behemoth. Elad Gil is joined by Booking Holdings CEO Glenn Fogel to discuss his career, from law school and Wall Street to working at Priceline through the dot-com crash, and to helping grow the business into a multifaceted, dynamic travel marketplace in the AI era. Glenn explains how leveraging AI and agents such as Priceline’s ‘Penny’ makes travel planning and customer service better, while emphasizing the importance of preserving some human support for some users. He also talks about Booking’s strategy of reinvesting over $700 million into AI and other technologies while still offering stock buybacks and dividends, the durability of their scale and complexities of dealing with a large portfolio physical properties across the world, and why upskilling is so important for employees amid concerns about AI-driven job displacement.      Sign up for new podcasts every week. Email feedback to show@no-priors.com Follow us on Twitter: @NoPriorsPod | @Saranormous | @EladGil | @bookingcom | @priceline Chapters: 00:00 – Cold Open 00:05 – Glenn Fogel Introduction 00:41 – Glenn’s Early Career 06:49 – Lessons from the Early Internet 09:24 – Deciding Factors for Exiting 10:56 – Travel Through the Lens of AI 13:30 – Agentic Travel Planning  18:59 – Agents, Token Economics, and ROI 22:46 – Booking’s Capital Investment Philosophy 25:23 – Scale as Durable Asset 29:40 – Purpose and Choosing Wisely 33:18 – AI’s Impact on Jobs 36:38 – Upskilling in the AI Era 38:36 – Public Perception of AI 40:24 – Conclusion