Before He Built Twitter, Jack Dorsey Applied for a Job at a Shoe Store. He Got Rejected.

Jack Dorsey in 2008

Jack Dorsey in 2008

Jack Dorsey / Flickr

The New York Times today has an excerpt from tech reporter Nick Bilton’s forthcoming book about the early days of Twitter. Those in search of juicy anecdotes and a Zuckerbergian antihero figure in the Twitter origin myth will not be disappointed. I won’t keep you in suspense: It’s Jack Dorsey.

In the course of Bilton’s excerpt, Dorsey goes from a shiftless NYU dropout with a nose ring to a backstabbing climber to a disastrous manager to being forced out of Twitter and considering a job at rival Facebook to … well, just read the thing.

But what stuck out to me about Dorsey, amid the parallels to Steve Jobs and Mark Zuckerberg, was that his is a more quintessential Silicon Valley rags-to-riches story than either of theirs. And it’s a quintessentially Millennial story, at that. Jobs was out of Reed College just a couple years before founding Apple at age 21. Zuckerberg founded Facebook from a Harvard dorm room at age 19. Dorsey, on the other hand:

… was a 29-year-old New York University dropout who sometimes wore a T-shirt with his phone number on the front and a nose ring. After a three-month stint writing code for an Alcatraz boat-tour outfit, he was living in a tiny San Francisco apartment. He had recently been turned down for a job at Camper, the shoe store.

Then Evan Williams, the Blogger co-founder and then-CEO of Odeo, the startup that would become Twitter, walked into the coffee shop where Dorsey was blaring punk rock on his laptop headphones.

Dorsey, who was shy after battling a speech impediment as a child, was reluctant to introduce himself personally. Instead, he opened his résumé on his computer, deleted any signs of his desire to work for Camper shoes, found Williams’s e-mail address online and sent a message to see if Odeo was hiring. Williams, whose investment in Odeo had turned him into the company’s C.E.O., soon called him in for an interview. He and [co-founder Noah] Glass, both college dropouts themselves, preferred rabble-rousers to Stanford grad students and Dorsey, with his nose ring and disheveled hair, seemed like a perfect fit.

Dorsey was hired, worked with Glass to develop Twitter, brutally betrayed Glass, and eventually remade himself as the dashing public face of the hottest social-media startup since Facebook. He’s now Twitter’s chairman and the CEO of Square, the mobile-payments company. When he tweets that he’s in New York, Michael Bloomberg tweets “Welcome back!”

Good thing he didn’t get that gig at Camper shoes.