Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode!

Expedia launched inside Microsoft on October 22, 1996, under Rich Barton, its name blending exploration and speed. A low-margin travel agency did not fit a software company, so Microsoft spun it off in 1999. Barry Diller’s IAC took a controlling interest in 2001, bought the rest in 2003, and spun it off again in 2005. Expedia then bought rivals rather than building: Trivago for 477 million euros in 2012, Travelocity for $280 million and Orbitz for $1.6 billion in 2015, and HomeAway for $3.9 billion, later merged into Vrbo. Now based in Seattle with 16,500 employees, the group earned $14.7 billion in revenue in 2025 across 3.5 million lodging properties and over 500 airlines.

Expedia also runs physical stores: Expedia Cruises began as CruiseShipCenters International in Vancouver in 1987 and had 260 franchise locations by 2024. In 2011 the South Carolina Supreme Court ordered subsidiary Travelscape to pay $6.3 million in back sales taxes, ruling that furnishing hotel rooms created a physical presence. In early 2020 Diller called the company sclerotic and bloated, and 3,000 jobs were cut that year, followed by 1,500 more in 2024. Lawsuits over hidden ranking practices came from independent hotels in California and regulators in Australia.

• One Key, launched in 2023, links loyalty points across Expedia, Hotels.com and Vrbo, and Travel Shops in 2024 let influencers earn commissions.
• During the 2020 pandemic, customers faced hours-long waits and disconnections seeking refunds, sparking multiple lawsuits.
• A February 2020 UN Human Rights Council list of companies in West Bank settlements included Expedia Group.
• In the Buckeye Tree Lodge case, Expedia showed non-partner hotels as sold out and steered users elsewhere, settling in 2021.
• Australian proceedings found Trivago highlighted a higher-priced room over 66 percent of the time based on pay-per-click bids, leading to a $32.91 million fine.