Day: September 24, 2025

• Billionaire Barry Diller said he liked bringing in people “without any experience” at their “earliest stage.”
• “You find out who swims and who doesn’t,” the IAC and Expedia Group chairman said on the “Invest Like the Best” podcast.
• Diller has mentored executive talent like Uber CEO Dara Khosrowshahi and former Disney CEO Michael Eisner.

Media titan Barry Diller puts his young workers to the test: sink or swim.

The IAC and Expedia Group chairman has mentored some of the biggest names in business, from Uber CEO Dara Khosrowshahi to former Disney CEO Michael Eisner. On the “Invest Like the Best” podcast, Diller shared his strategy for guiding early career hopefuls.

Diller said that he liked bringing people in “without any experience” or “expertise” at their “earliest stage.”

“Then you give people more responsibility than they qualify for, because, in that forge, you find out who swims and who doesn’t,” he said. “If you have that kind of environment, out of it is going to come pretty good people.”

Diller started his career with little experience. He dropped out of UCLA and began working in entertainment in 1961 through the William Morris Agency’s mailroom.

A few decades later, Diller boosted Paramount Pictures with hits like “Raiders of the Lost Ark” and “Saturday Night Fever,” and co-founded Fox Broadcasting Company with Rupert Murdoch.

“I was totally unprepared, and I had no reason for anyone to give me any responsibility, because I had no experience about anything,” Diller said on the podcast.

Diller’s bosses also assigned him more than he was qualified for: “I got dropped in the deep end of the water, and I figured out how to swim,” he said.

As for more senior-level talent, Diller isn’t a fan of hiring them. In 2018, Diller shared his one rule for hiring top talent: “If you hire people at senior positions, you are a failure.”

“I have always believed to hire people, bring people into your organization who are young,” Diller said.