Hustle in the Mailroom: How He Earned a Foothold

Michael shares his aggressive mailroom tactics, long hours, and how he became indispensable to an executive through initiative.

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Episode notes

Every dealmaker in Hollywood has a story. Michael Ovitz has all of them.

From Ghostbusters to Goodfellas, he packaged the films, brokered the talent, and rewrote the rules of power. What started as a rebellion inside William Morris became a $2 billion empire called CAA, and a playbook Silicon Valley still follows.

In this episode of Big Shot, Harley and David sit down with Michael Ovitz, the legendary founder of Creative Artists Agency and the man who redefined power in Hollywood.

From a working-class childhood to representing the world's biggest stars, Michael’s story is one of obsession, reinvention, and relentless ambition. He helped shape more than 300 films, including Jurassic Park, Ghostbusters, Tootsie, Stand by Me, and Goodfellas, while transforming how deals, talent, and ideas move through the entertainment industry.

This episode is brought to you by Firebelly Tea. Use code bigshot15 for 15% off your order https://www.firebellytea.com/

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In This Episode We Cover:

(00:00) Intro

(01:39) Michael’s early years

(02:53) How Jewish mothers blend boundless belief with practical ambition

(06:15) Michael’s advice to a failed businessman

(15:44) How Marc Andreessen pulled Michael into Silicon Valley

(21:00) How early anti-semitism made Eisner’s betrayal cut deeper

(25:37) The Yahoo deal Eisner blocked

(30:25) The story behind the Jurassic Park pitch and Spielberg’s involvement

(34:11) The hit-to-miss ratio in Hollywood, and how Michael’s movies were almost always hits