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Jack Dorsey recounts how he almost became a massage therapist after his first startup failed

May 24, 2024

Jack Dorsey’s first company—a web-based dispatch company called DNet—was, as he puts it: “a complete and utter failure.”

After the company folded in 1999-2000, Jack took on various contracting jobs, and his wrist started hurting. Fearful that he was developing carpal tunnel, his friends advised him to get a massage:

“But I’m not someone who just goes to get the massage. I want to learn how to give massages… I decided I’m not just going to get a massage, but I’m going to become a massage therapist.”

After a thousand hours of massage therapy, Jack was a licensed therapist and ready to move back to San Francisco in 2005:

“I was actually going to dedicate my life to it… I thought I had the best idea ever. My idea was that I would go out to California and I would do chair massage for programmers. And while I was massaging their shoulders and their wrists, I would also give them advice on their code… it was not only massage therapy, it was code therapy… I started telling people my idea and they’re like, that is the stupidest thing I’ve ever heard. I said, no, just give it a chance.”

When he moved back to San Francisco, Jack realized there were already a ton of massage therapists and it would be hard to compete, so he went back into programming.

One year later, he would invent Twitter, and three years after that, he cofounded Square.