Author: Charles

Barry Segal: The Comedy That Made His Dream Come True

Barry Segal: The Comedy That Made His Dream Come True

A Wall Street Banker Turned to Comedy for Happiness and a Career Change

A Wall Street Banker Turned to Comedy for Happiness and a Career Change

Barry Segal doesn’t want to be a “banker.” On the one hand, he’s the founder and head of Segal Capital Management, a hedge fund specializing in the high-yield securities that made the American Dream a myth. On the other hand, he’s been selling real estate and serving on the boards of real estate organizations since he was 21.

So when Segal made the unexpected decision to go through with a comedy career in 2015, it meant not giving up his day job, managing money through the market’s ups and downs, and putting his energy into a dream he’d never actually have: turning himself into a funny person in the age of Trump. As part of his efforts to make that happen, he joined the roster of stand-ups he’d been watching for years.

When he got to the first round of auditions, he was surprised to discover how many comics turned him down. “Of those who did go on, there were a bunch of very talented people, but I had no idea where they were going to land,” he says. During the second round, he made his head spin when a guy he called “my favorite” walked across the stage. While everyone laughed and clapped, Segal couldn’t stop thinking about what a strange coincidence it was that the same man had been onstage before, in this very room at this very moment. And he realized what an honor it was to have a fellow stand-up in his corner, someone who he could trust to always be there when he went through some of the toughest times of his life.

“I think comedy is the best medicine,” Segal says. “I went through a breakup a third of my life, and I was a bit broken, a bit beaten down, but I was also very good at being able

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