What-if certainty 3/5 debate potential 3/5

Senra: Ovitz would have made more money and avoided hatred in finance

David Senra · Inside the Minds of the Most Successful Founders | David Senra · Feb 19, 2026 · at 31:03

Founders podcast host David Senra analyzes CAA co-founder Michael Ovitz's ruthless Hollywood dealmaking career and relational regrets.

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“I think almost if he took his exact same skill set, because he essentially the world, what is an agent? Agent is a salesperson. He was like the world's greatest agent. So it was like world's greatest salesperson and literally just moved it to the East coast and just worked it because he was running the fund and he's been like, he's one of the greatest fundraisers I've ever seen. And he's got all these crazy connections. And I just think one, not that he made enough money. He's got, he's a multi-billionaire. He's fine over there. He would have made more money, but I think he would have been He just wouldn't have been universally hated”

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