Buying Expedia and Timing After 9/11

Barry tells the Expedia acquisition story, negotiating with Microsoft and closing despite 9/11's impact.

Play episode from 38:05

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Episode notes

Barry Diller started in the mailroom at the William Morris Agency, but he had no interest in becoming an agent. He didn’t hustle the way others did. Instead, he spent his time in the file room, reading everything he could and learning how the business actually worked. By his own account, he likely would have been fired if not for one thing: his connection to Danny Thomas.

In this episode of Big Shot, Barry sits down with Harley and David to reflect on the path that took him from that mailroom to running studios, building networks, and shaping modern media. He shares how his ambition came later, not as something he chased but something he discovered, and how his career was shaped as much by timing and luck as by intention.

Along the way, Barry walks through the decisions that defined his career, from rising quickly through ABC and becoming chairman of Paramount at 32, to building the Fox network alongside Rupert Murdoch, and later taking control of IAC and acquiring companies like Expedia.

This is a conversation about instinct, timing, and the willingness to walk through the door when it opens.

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In This Episode We Cover:

(00:00) Intro

(03:32) Barry’s early heroes and influences

(05:16) Where his ambition came from

(06:50) Getting his start in the mailroom at the William Morris Agency

(08:53) What he learned from reading client files at William Morris

(12:10) Working as an assistant at William Morris

(14:00) How he got a job at ABC

(16:32) Barry’s thoughts on serendipity

(19:20) Developing The Movie of the Week and miniseries at ABC