Episode 41: Booking.com with Jetsetter & Room 77 CEO Drew Patterson

Acquired trains its lens on the “second or third best acquisition of all-time”, Priceline’s 2005 purchase of Booking.com. Our heroes are joined by friend-of-the-show and former Jetsetter & Room 77 CEO Drew Patterson to help understand how this little-known startup from The Netherlands grew into the largest travel company in the world, with nearly $8B in annual revenue. Was this deal even better than Instagram??? We debate, hotly.   

Sponsors:

• WorkOS: https://bit.ly/workos25
• Intapp: https://bit.ly/intappceleste
• Sentry: https://bit.ly/acquiredsentry
• Anthropic: https://bit.ly/acquiredclaude25

More Acquired!

• Get email updates with hints on next episode and follow-ups from recent episodes
• Join the Slack
• Subscribe to ACQ2
• Merch Store!

© Copyright 2015-2025 ACQ, LLC

Topics covered include: 

• The biggest startup you’ve never heard of (in the US), Booking.com, and its parent company Priceline (yes, the William Shatner Priceline)
• Booking’s founding in Amsterdam in late 1996: by recent college graduate Geert-Jan Bruinsma
• Skift.com’s Definitive Oral History of Online Travel 
• The travel industry's GDS's (“Global Distribution Systems”) and the development of Sabre 
• How Bruinsma raised the initial money for Booking: by emailing anyone he know who had an email address 
• OTAs ("Online Travel Agencies”) and how they operate; the "merchant model" versus the “agency model"
• The role of search in online travel 
• Bill Gurley on  Conversion: The Most Important Internet Metric of All
• Expedia’s early flirtation with Booking, and decision not to acquire the company
• Priceline head of M&A Glenn Fogel’s vision for how powerful the agency model for OTAs could become in Europe
• Priceline and Glenn's 2004 acquisition of Active Hotels in the UK, followed by the 2005 acquisition of Booking for $133M and the combination of the two businesses into Booking.com 
• Booking’s incredible growth in the decade since the acquisition, from less than 20M room-nights to over 500M, and $7.8B in revenue in 2016

  The Carve Out: 

• Ben: Scott Forstall talking about the original iPhone at the Computer History Museum
• David: The Big Sick
• Drew: Bloomberg’s Money Stuff by Matt Levine