Longreads + Open Thread

Liar's Poker, Neom, AI Economics, Prediction Markets, Writing for AI, Volatility, Diller

Longreads

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Books

Who Knew: Barry Diller was once pretty young to be running an entire movie studio on his own, and is now surprisingly old for a dot-com dealmaker (his corporate mothership, IAC, has owned and subsequently spun off brands like Expedia, TripAdvisor, LendingTree, and Match/Tinder). The first half of his autobiography feels like a Gore Vidal novel: he grew up feeling deeply ashamed of his sexual orientation, and morbidly afraid that his parents would find out (especially since they had their hands full with his drug-abusing older brother). Early on, he seems pretty dysfunctional, and once he joins the workforce at the William Morris Agency through a friendship—the early chapter is peppered with references to partying at Lew Wasserman's house, being friends with Doris Day's son, etc.—he looks like a different archetype, the well-connected but unambitious entertainment-adjacent underachiever.

It's hard to tell what clicked for him. One minute, he's dragging his feet on leaving his mailroom job because he knows he won't make it as an agent. Then he uses yet another connection to get a job at ABC, and suddenly he's a media dealmaker who more or less invented the made-for-TV movie category.

Soon enough he's off the Paramount, which he started running when he was 32. This is the most fun part of the book, especially for someone who doesn't have that much awareness of middlebrow 70s and 80s movies. (The most bizarre concept he mentions is Heaven Can Wait, "a 1978 American sports fantasy comedy-drama" involving a football player who keeps getting reincarnated. It may not be entirely unrelated that Diller finds out his driver, Mario, was also in the business of selling cocaine to Diller's friends.) These chapters give Diller a lot of time to talk about people he mentored, and also to talk about some of his grievances. He's still mad that George Lucas didn't honor his commitment to do a Raiders of the Lost Ark sequel on the terms he agreed to before making the first one a hit.

And that makes sense. The media business is a weirdly fragmented one, where there's extreme scarcity for some things (there are only so many good weekends to launch a movie, actors, writers, and directors are doing one thing at once, and early in Diller's career broadcast time slots were also scarce). And it's a business with unpredictable payoffs. And it's a business with big information asymmetries, and lots of opportunities to strategically close them. So the whole business is basically structured so lots of incredibly egotistical people have numerous opportunities to betray one another, develop grudges, reconcile when it's strategically sound, and top it all off with a pretty fun memoir.

Open Thread

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