Squawk Pod Leaders Playbook: Billionaire Barry Diller 1/21/26
8 snips
Jan 21, 2026 
In a captivating conversation, Barry Diller, the dynamic Chairman of IAC and Expedia Group, shares insights from his illustrious six-decade career in media and tech. He discusses his buy-grow-spin strategy at IAC, the lucrative potential of online dating, and the importance of 'creative conflict' in decision-making. Diller emphasizes the value of direct communication with employees, the risks he took with Expedia, and the significance of curiosity in his success. His leadership playbook merges instinct, willfulness, and execution for sustained innovation.
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Build An Anti-Conglomerate To Scale
- Barry Diller builds IAC as an "anti-conglomerate" that spins companies out once they reach scale.
- He believes independence and transparency help businesses thrive after incubation.
Seeing The Obvious In Online Dating
- Diller saw online dating as an obvious replacement for bars and being fixed up by friends.
- He was glad competitors hadn't pounced, so IAC moved quickly on Match.com.
Use Creative Conflict To Test Ideas
- Encourage "creative conflict" by plumbing passionate, conflicting views in a room.
- Push the debate past exhaustion to surface the strong, actionable ideas.
