Barry Diller: Building IAC

My guest this week is Barry Diller, one of America’s most successful businessmen. At 83, he chose to publish a deeply personal book and open up about his successes and failures.

With surprising candor he details the rules he’s lived by: trust first, confront directly, and make the call when the clock starts. In our conversation, he shares why success teaches you nothing, why failure is essential, and why instinct still beats algorithms in a data-obsessed world.

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Featured clips

17:58

Changes In The Entertainment Industry

22:35

Instinct Vs Data

52:39

Accountability During Conflict

Available Now: Apple Podcasts | Spotify |YouTube | Transcript

This episode is filled with Hollywood lore and business acumen. 

Takeaways:

1. The clock starts the moment you know.
2. Money is a byproduct, not a motivation.
3. No job is below you.
4. If you want responsibility, take it.
5. Don’t run from confrontation.
6. If you don’t get what you want, be prepared to walk away.
7. The best way to learn is to start something, where each step teaches you every task.
8. Instinct beats algorithms.
9. “Data can tell you what has happened, not what can or will happen.”
10. Don’t treat your job as a stepping stone.
11. It’s far better to be underestimated than overestimated.
12. Make decisions as an optimist, not a pessimist.
13. “The daily drip of cynicism that this business generates in carloads has to be constantly exorcised.”
14. Decision-making shouldn’t be peaceful.
15. The outside of picture-perfect mansions and the inside rarely resemble each other.
16. Curiosity is the only success metric that matters.
17. Hire for hunger.
18. Don’t get into contests.
19. Don’t look back at what might have been. Keep your eyes on the horizon.
20. If you like the idea, start. Don’t over-analyze.
21. Act like a principal, even if you’re not one.
22. “You either are or you are not capable of being on your own.”
23. “The world belongs to the discontented.” – Robert Woodruff
24. Start with trust.
25. Conventional wisdom is uninteresting.
26. “Either you are or you’re not.” Independence is binary.
27. Read everything with a detective’s eye.
28. To get the job you want, master the one you have.
29. Risk without reward is charity.
30. Conflict is better than consensus.

Lessons

1. The process: “One dumb step in front of the other, course-correcting as you go, is the only process I’m any good at.” Diller bounces off walls to find doors. Makes mistakes. Find what works. Repeat. This is the process.
2. The dark hours matter. Nobody wanted the William Morris file room job. Diller took it. He read every contract from Hollywood’s 70-year history. “I’m no good unless I understand everything down to the smallest molecule.” His peers networked upstairs while he studied in the basement. They became agents. He became a mogul.
3. The clock starts the minute you know. Two executives were stealing from Diller’s company. Someone suggested burying it. The thief even tried blackmail. Barry discovered his most important principle: the second you know about a problem, you own it. Before that moment, nothing is your fault. After that moment, every second is yours.
4. Start with trust. Diller starts with trust. “I’ve been in situations where it’s been misplaced, to say the least.” He forgets the betrayals. No vengeance. Just forward motion. Others waste fortunes on safeguards and lawyers. He moves at the speed of trust. Paranoia is expensive. Trust is profitable.
5. Instinct over Algorithms. Netflix knows the exact second you stop watching. None of it matters. “Predictive research is worthless for making forward decisions,” Diller says. Data tells you what happened, not what will happen.
6. Make decisions as an optimist, not a pessimist. “Every time I’ve made a decision out of cynicism, it’s been poor.” Experience breeds sophistication. Sophistication breeds cynicism. Cynicism kills instinct. After decades in Hollywood, Barry still fights to stay naive.
7. No job is too small or below you. “There was no task I wouldn’t do, tiny or large, no length to which I wouldn’t go.” While peers positioned for promotions, Diller did everything. He worked the hours nobody worked, doing the things nobody wanted to do. His job wasn’t a stepping stone to something else; he was all in. Excellence where you are creates opportunity where you’re going.
8. If you don’t get what you want, be prepared to walk away. Les Wasserman taught Diller negotiation in one sentence: “Be fully prepared to call the whole deal off if you don’t get what you asked for. Otherwise, you never will.” Power comes from needing nothing. Leverage comes from walking away.
9. Conflict is better than consensus. “I love confrontation,” Diller admits. Not to be difficult. To find truth. Calm meetings produce consensus ideas. Explosive meetings produce advantageous divergences. If you listen through the noise, you’ll hear what matters. Friction creates fire.
10. Become a life-long learner. At 83, after running studios and building empires, what’s success? “Remaining curious. If I’m curious, then that is success.” Curiosity compounds forever.