When it comes to identifying great ideas, billionaire Barry Diller has a simple piece of advice: Don’t be a cynic.
Diller is a big fan of “creative conflict” group brainstorming sessions, he said in an interview for an episode of CNBC’s “Leaders Playbook,” set to air on Wednesday. In a creative conflict setting, team members passionately argue about an idea, weighing differing opinions for however long it takes to reach a decision. It can be “loud and argumentative … and somewhat brutal,” but “I think it’s a great environment,” he said.
For group brainstorming to work effectively, resulting in top-tier ideas, you’ll need to genuinely consider other people’s opinions, said Diller, chairman and senior executive of holding company IAC and travel technology company Expedia Group.
“You have to try and be naive,” said Diller, 83, who also co-founded the Fox Broadcasting Company. “You cannot be cynical. Cynicism kills everything. You have to force naivete.”
DON’T MISS:Â How to build custom GPTs and use AI agents
If you’re cynical, you may think your team member is pitching an idea that only benefits them — or that since you’ve been at your organization the longest, you naturally know more than the next person.
Instead of being dismissive, go into these ideation sessions with a beginner’s attitude, said Diller, who has an estimated net worth of $5.5 billion, according to Forbes. That doesn’t mean being foolish, ignorant or easily steamrolled — rather, you’re open to fresh perspectives, learning something new and being challenged.
“I’ve always held on to being a dopey naive as much as I can,” said Diller. “You know, as you go through life, you just get more sophisticated and the natural tendencies get more cynical. If you want to use your instincts, you have to brush that clean every day practically.”
How listening can help you make difficult decisions
The value of considering your colleagues’ unconventional ideas can go beyond brainstorming.
In the interview, Diller discussed IAC’s purchase of a majority stake in Expedia. In July 2001, Diller made a deal to buy a 75% stake in Expedia for about $1 billion. Two months later, before the deal was completed, the September 11 terrorist attacks halted U.S. travel almost entirely.
Expedia had “zero revenue for a while, and it came back relatively quickly, but at that critical moment, when we had to make the decision, there was no business,” said Diller. “Several people said, ‘This is not the time to pay over a billion dollars for something that, right now, is so completely unpredictable’ … But someone in the room, when we were talking about this, at the height of the argument, said, ‘If there’s life, there’s travel.'”
“As soon as I heard it, I said, ‘Close [the deal]. I’m betting on that if there’s life, there’s travel … and if there isn’t life, then who cares anyway?’ And that was it. It was very binary.”
Diller’s IAC finally acquired Expedia in August 2003, and Diller helped steer the company through the Great Recession and the Covid-19 pandemic. Expedia Group now owns and operates several other travel sites including Hotels.com, Vrbo, Travelocity and Trivago, and currently has a $36.44 billion market cap.
Watch Barry Diller on CNBC’s “Leaders Playbook″ on Wednesday, Jan. 14 at 10:30 p.m. ET/PT. All new episodes Wednesdays.
Want to get ahead at work with AI? 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 boost your productivity today. Use coupon code EARLYBIRD for 25% off. Offer valid from Jan. 5 to Jan. 19, 2026. Terms apply.












































