How Media Mogul Barry Diller Made His $3 Billion Fortune

Meet the media titan who once paid more than $100,000 to clone his Jack Russell terrier.

They simply don’t make moguls like Barry Diller anymore. Chairman and Senior Executive of IAC and Expedia Group, the billionaire’s portfolio includes a coveted cohort of internet properties, including Vimeo, HomeAdvisor and Investopedia. With a market cap of $30 billion, Match Group (Tinder, Match, OkCupid and other brands) is the largest business IAC has spun off in its 25-year history. At 78, he has united a motley crew of tech ventures into an apparently compatible, profiteering juggernaut. 

Known for his rabid curiosity, spiked with a healthy dose of charm and self-deprecation, Diller, worth an estimated $3 billion, is smooth as Hermès silk. He has systematically mentored other titans—among them Jeffrey Katzenberg, Michael Eisner and Uber’s Dara Khosrowshahi—with such manifest strategy, it all but guarantees his influence in the industry for decades to come. 

It could be argued that the most meaningful bond in Diller’s life is the one shared with his wife Diane von Furstenberg. One of the original New York power couples, it was the divorced designer who initially suggested they get married. This pair has gone from partying at Studio 54, to the friend zone, to husband and wife. The sun-kissed couple love sailing aboard Diller’s superyacht, Eos, which measures 305 feet long and cost an estimated $200 million. 

A child of the ’50s, Diller came of age to the moral compass of Father Knows Best and The Donna Reed Show. How remarkable then, the emotional footprint his dating companies have left on our cultural landscape. The rise of fluid, à la carte hookups was in large part due to his former brands Match.com and Tinder. Such social vehicles encouraged a language of compatibility around shared interests, albeit layered alongside Darwinistic desire, giving us a vocabulary for such experiences.

Raised in Beverly Hills, where his father was successful in real estate development, Diller attended UCLA but dropped out to work in the mailroom of the William Morris talent agency. There he worked alongside future industry icon David Geffen, with whom he remains exceedingly close. He moved to ABC in 1964 and hit pay dirt a few years later, at the age of 25, for ushering in the network’s “Movie of the Week” concept. By 1974, he had landed at Paramount, where he worked for a decade, producing a stream of hits.  

One anecdote sums up late-stage Diller more than any other: he loved his dog so much, he paid upwards of $100,000 to South Korea’s Sooam Biotech Research Foundation to clone her. He has three Jack Russell terriers cloned from implanting his beloved Shannon’s DNA into another dog’s eggs. Has Diller started a trend? Barbra Streisand came out as a cloner in an interview with Variety, inspired by Diller to clone her Coton de Tulear. 

The plucky pup Diller found orphaned on a back road in Ireland brought out a tender side of Barry rarely seen in public. At his and von Furstenberg’s annual pre-Oscars party one year, the playful terrier jumped onto the Spanish-style roof of the couple’s posh ranch house. When Shannon ran too close to the edge, celebrity guests cheered Diller on as the doting dog dad climbed up on the roof to usher his canine to safety. 

The couple, who host a picnic every Saturday before the Oscars on the lawn of their Beverly Hills mansion, have welcomed luminaries including Oprah Winfrey, Bradley Cooper, David Geffen, Valentino, Diana Ross, Jeffrey Katzenberg, and Eric Schmidt. Diller is a generous, loyal, gunslinger in all the ways that matter most. 

Diller has made a name for himself by challenging convention. The ultimate political operative, he has placed Chelsea Clinton on the boards of two of his companies. From jetsetting with Josh Kushner and Karlie Kloss, Diller keeps up a gilded circle of friends stacked with power brokers. 

In one of the last normal society gatherings before COVID-19 changed everything, Diller relished in an evening to fête his wife at one of the Eiffel Tower’s restaurants in Paris. The occasion? The designer being awarded the Légion d’honneur, the highest award for service to France. It was her son, Alexander von Furstenberg, who spearheaded the party in late February with Diller, after generously placing the winning bid on an evening takeover of the Eiffel Tower at an amFAR auction last year. 

The designer was being honored in part for raising over $100 million in support of the Statue of Liberty Museum. At the celebratory dinner, Diller toasted his wife alongside their high-wattage social circle, including Marisa Berenson, Jeff Bezos, Larry Gagosian, Christian Louboutin, Antoine Arnault, Seth Meyers, and British Vogue editor-in-chief Edward Enninful. Diller’s superpower has always been his social skills. His real net worth lies in his sphere of influence.