Dick Costolo Gave Up On His Dream -- And Now He's Worth $US430 Million

When Twitter filed for an IPO last fall, it revealed that Twitter CEO Dick Costolo owns more than 7.5 million shares in the company.

Today, Twitter shares are worth $US57. That means Costolo stake is worth something like $US430 million.

Obviously, Costolo’s professional life is a wild success.

But it turns out he’s only had this success, because he was once a such failure. We learned this watching a Pando Monthly video

Back in December, Costolo told PandoDaily editor-in-chief Sarah Lacy a funny story about how, after college, he pursued his dreams — and failed.

The story started when Lacy asked Costolo if it was true that he was once a comedian. “Was that like, a class you took, or actually a profession?”

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Costolo, laughed and said: “Well, maybe in retrospect, I should have been thinking about it as a class I took” — but yeah, being an improv comedian was once his job.

He said that when he was senior working on a Computer Science degree from Michigan, he needed Arts credits to graduate.

He said he looked through course catalogue for a class where there would be “no homework.” He found a theatre class. He started doing open mics.

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He said he ended up liking his classes so much he called up his parents and told them he wasn’t taking any of the CS job offers he’d gotten. He was moving to Chicago to do improv comedy.

He told Lacy he got a gig with famous improv group Second City, and later another at The Annoyance Theatre. He did it for years.

Costolo said the job was really hard. He worked with lots of really talented comedians. Some, like Steve Carrell made it big. Others, who were you thought were sure bets to make it on Saturday Night Live, didn’t.

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Costolo said he always got all the invitations to audition that everyone else always got — but he never got the big parts.

Lacy asked him if he looks back on it as a heart-breaking time.

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Costolo said “no, it awesome. I don’t have any regrets…I had no money though.”

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“You’ve got quite a lot now,” Lacy said.

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Costolo said because he was rehearsing during the day and performing at night, he had to have weird jobs. Like at the Crate & Barrell in the wedding registry section, or in the coat check at the Limelight Lounge.

Once, when Costolo was working the coat room an old classmate from the CS program showed up and was like “Whoa. What happened?”

Costolo remembers going to a lunch place and the menu said “soup & sandwich, $US6.95” and he remembers thinking, “wow, that would be awesome if I could do both of those.” He couldn’t afford it.

Costolo said he would get invited to audition for SNL, and he would get all excited — and then he’d show up and there were 60 people there. “You realise it’s not a big deal.”

Lacy asked: “At what point did you feel like this is just not going to happen?”

Costolo said when everybody else started getting hired — getting jobs writing for Conan O’Brien, jobs on SNL. “At some point you’re just like this is not going where it needs to go.”

After trying for five years, Costolo quit. “Going back to technology happened in an instant of me saying, I can’t have no money at all, ever, constantly like this, it’s driving me crazy. I’m going to go put my CS degree to work and get a real job.”

That was 1990. 20-four years later, Costolo is the CEO of a huge Internet company and worth more than $US400 million. Lacy asked him what do his old actor friends think about how his life turned out?

Costolo said he saw Steve Carrell, now a famous actor, at a hospital fundraiser recently. Carrell hadn’t known whatever happened to Costolo after they were in a troup together in 1985. Costolo filled him in that night. Carrell patted him on the back and said: “I’m really sorry it didn’t work out for you.”

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