Billionaire Barry Diller has simple advice when it comes to identifying good ideas: “Don’t be a cynic.”
Diller is a big fan of the “Creative Conflict” group’s brainstorming sessions, he said in an interview on an episode of CNBC’s “Leaders’ Playbook” scheduled to air Wednesday. In creative conflict situations, team members passionately discuss ideas and weigh differing opinions no matter how long it takes to reach a decision. Although it can be “loud, argumentative and a bit brutal,” he says, “I think it’s a great environment.”
Mr. Diller, chairman and senior executive of holding company IAC and travel technology company Expedia Group, said that for group brainstorming to be effective and generate top-notch ideas, it requires serious consideration of the opinions of others.
“You have to try and stay naive,” said Mr. Diller, 83, who also co-founded the Fox Broadcasting Company. “Don’t be a cynic. Cynics kill everything. Simplicity must be enforced.”
Don’t miss: How to build a custom GPT and use AI agents
If you’re cynical, you might think your team members are proposing ideas that only benefit them. Or you might think that because you’ve been with the organization the longest, you naturally know more than the next person.
Diller, who has an estimated net worth of $5.5 billion, according to Forbes, said to approach ideation sessions with a beginner’s attitude rather than being negative. It doesn’t mean being stupid, ignorant, or failing easily; rather, it means being open to fresh perspectives, learning something new, and being challenged.
“I’ve always been as stupidly naive as I can be,” Diller said. “As we go through life, humans become more sophisticated and our natural tendencies become more cynical. If you want to use your instincts, you have to practically clean them every day.”
How listening can help you make difficult decisions
The value of considering your colleagues’ unconventional ideas can go beyond brainstorming.
In an interview, Diller spoke about IAC’s purchase of a majority stake in Expedia. In July 2001, Dealer entered into an agreement to purchase a 75% stake in Expedia for approximately $1 billion. Two months later, and before the deal could be finalized, the Sept. 11 terrorist attacks brought a near complete halt to U.S. travel.
Expedia “had zero revenue for a while and recovered relatively quickly, but at a critical moment when a decision had to be made, the business was not there,” Diller said. “Several people were saying, ‘Now is not the time to pay over a billion dollars for something that is completely unpredictable’…But as we were talking about this, someone who was there right in the middle of the discussion said, ‘Where there’s a life, there’s a journey.'”
“As soon as I heard that, I said, ‘Let’s make[the deal]. I’m betting that if there’s a life, there’s a journey…but if there’s no life, who cares anyway?’ That’s it. It was very binary.”
Mr. Diller’s IAC ultimately acquired Expedia in August 2003, and Mr. Diller helped steer the company through the Great Recession and the COVID-19 pandemic. Expedia Group currently owns and operates several other travel sites, including Hotels.com, Vrbo, Travelocity, and Trivago, and has a current market capitalization of $36.44 billion.
Watch Barry Diller on CNBC’s “Leader Playbook” on Wednesday, January 14th at 10:30pm ET/PT. All new Wednesday episodes.
Want to use AI to advance your work? Sign up for CNBC’s new online course, Beyond the Basics: How to Use AI to Supercharge Your Work. Learn advanced AI skills like building custom GPTs and using AI agents to increase your productivity today. Use coupon code EARLYBIRD for 25% off. Offer valid from January 5th to January 19th, 2026. Terms and conditions apply.
