Oct 7, 2015 ยท 3 minutes

A few months ago, I wrote that it was Adam Bain not Dick Costolo who had it the roughest with the recent Twitter upheaval….

Costolo, after all, is departing the company entirely -- leaving the dysfunctional board and washing his hands of the situation. No one can take that 30x appreciation from him…

Costolo has a good shot of coming out of this like the prematurely ejected Jerry Yang who later vindicated himself with Alibaba’s monster IPO-- a deal he brought to Yahoo in the first place-- while his successors flamed out (Carol Bartz) and flamed out (Scott Thompson) and even one of the top superstars of Silicon Valley is not doing so hot at the job (Marissa Mayer.)  

He can sit back and shrug if it gets worse, because it has nothing to do with him. Yet another cautionary tale in why removing the CEO does little to fix a company with a fundamental product and user growth challenge.

What I knew at the time, but was asked to keep off the record, was another reason Costolo’s life is comparatively sweet these days-- he’s jetting back and forth between LA and Silicon Valley writing for the show Silicon Valley. Yesterday, Mike Judge spilled the beans about Costolo’s role during a conference hosted by Vanity Fair.

Said Costolo over email: “It's exhilarating to be In the room with so many remarkably funny people. Their ability to both maintain the structural integrity of the show and its characters while also making it side-splitting funny is incredible. It's frankly also fun to have to show my badge to the security person in the morning.”

There are so few firsts left in the startup world, but this may be one of them: A comedian who quits to become a coder, rises to the top of the tech world, leaves a top public company unceremoniously and then waltzes back into the arms of the comedy world. After all, the rejection he must have felt not getting picked for Saturday Night Live is nothing compared to the glare of the public markets, where even Twitter’s earliest shareholders endlessly concern trolled him

I went back to revisit the story Costolo told us at PandoMonthly just after Twitter went public about his comedy days. (Here’s the story in a format only Business Insider could put together.)

As Costolo told it, he started as a comedian because it was a class he could take in college with no homework. He loved it enough he told his parents he wasn’t taking any of the computer science jobs he was offered and was moving to Chicago to do improv instead. He did well enough to get invited on all the same auditions as others, but he never got picked for the plum SNL-like gigs. He said he didn’t have any regrets but he also had no money.

He told an amazing story about walking into a lunch spot and saw the menu boasted soup and sandwich for $6.95. He remembered thinking, “Wow, it would be awesome if I could do both of those.”

After five years, he quit. He said at the time, “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 put my CS degree to work and get a real job.”

Later he met back up with Steve Carrell at a hospital fundraiser. The (then) Twitter CEO filled Carrell in on all that had happened since he quit comedy, to which Carrell patted him on the back and quipped, “I’m really sorry it didn’t work out for you.”

Carrell was kidding but, in a twist of fate, the ugly ending of Costolo’s CEO tenure has given him back his college dream: He’s back writing on a hit comedy show and he’s got enough cash for all the soup and salad and sandwiches he could ever dream of.

Suck it, Carrell!

There’s almost no one better placed to write about the painful absurdity of post-IPO life.  You have to wonder if, next season of Silicon Valley, there’ll be a new character who bills himself as the next Steve Jobs and has an artisanal beard...
(Costolo is one of our top speakers at next year’s Pandoland in Chicago, where he’ll talk about these and more transitions. Get your super early bird tickets now!)