Glenn Fogel, CEO of Booking Holdings, has built a $170B travel empire that includes brands like http://Booking.com, Priceline, Kayak, and OpenTable. Glenn shares insights into how Booking has grown into a global powerhouse, weathering challenges like tsunamis, wars, 9/11, and the COVID-19 pandemic. We dive into the strategy behind the transformative acquisition of http://Booking.com, which now drives 90% of the company’s revenue, and the key lessons Glenn has learned about M&A success. Glenn also discusses how AI could revolutionize travel, from automating customer service to creating seamless traveler-first experiences.

(00:00) Intro

(01:37) Overview of Booking Holdings

(02:31) Early Days of Priceline and Joining the Company

(03:33) Dot-Com Boom and Financial Challenges

(07:28) Travel Industry Resilience

(07:47) Cultural and Economic Factors in Travel

(09:17) Stock Splits and Employee Incentives

(13:34) Acquisition of Booking.com and Active Hotels

(24:20) Growth and Integration of Acquired Companies

(29:11) Artificial Intelligence in Travel

(30:57) Future of Travel and AI Integration

(38:54) The Greatest Acquirers in History

(39:16) Teamwork in Business Acquisitions

(40:48) Challenges in M&A and Regulatory Hurdles

(41:49) Patterns in Successful and Failed Deals

(46:06) Cultural Alignment in Mergers

(50:31) Brand Management and Integration

(54:14) Regulatory Environment and Smart Regulations

(01:00:11) Post-COVID Business Travel Trends

(01:08:24) Leadership Through Crises

(01:15:33) Technological Advancements in Travel

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.