2000s
Diller was the Chairman of Expedia and the Chairman of IAC/InterActiveCorp, an interactive commerce conglomerate and the parent of companies including HomeAdvisor, Match Group (until 2020), Citysearch, and Connected Ventures, home of Vimeo and CollegeHumor (until 2020). IAC/InterActiveCorp is also the parent company of Tinder, Urbanspoon, The Daily Beast, and more. In 2005, IAC/InterActiveCorp acquired Ask.com, marking a strategic move into the Internet search category. He stepped down as chief executive officer of IAC/InterActiveCorp on December 2, 2010.
The new headquarters for the IAC/InterActiveCorp, the IAC Building was designed by Frank Gehry and opened in 2007 at 18th Street and the West Side Highway in Manhattan's Chelsea neighborhood. The western half of the block is dedicated to the building, which stands several stories taller than the massive Chelsea Piers sporting complex just across the West Side Highway. The extra floors guarantee a panoramic Hudson River view from Diller's sixth-floor office.
Diller has been on the board of Coca-Cola since 2002.
In 2003, on the PBS program NOW with Bill Moyers, Diller voiced a strong warning against media consolidation. In the interview he referred to media ownership by a few big corporations as an oligarchy, saying the concentration strangles new ideas.
Diller was "the highest-paid executive [of fiscal year 2005]", according to a report by The New York Times on October 26, 2006, with total compensation in excess of $295 million (mostly from stock).
Since 2013, Diller has co-produced more than ten Broadway shows in partnership with Scott Rudin, including To Kill A Mockingbird, West Side Story, Carousel, The Humans, Three Tall Women, Gary: A Sequel to Titus Andronicus, and A Doll's House, Part 2. IAC Films has also backed numerous films produced by Rudin, including Uncut Gems, Lady Bird, Eighth Grade, The Meyerowitz Stories, and Ex Machina.
In October 2019, Diller had a $4.2 billion fortune in technology companies, after investing early on in companies such as Match.com and Vimeo. In 2012, Diller became an investor in the streaming service company Aereo. Aereo went out of business in June 2014 after the United States Supreme Court ruled that its method of streaming media content violated copyright laws.