There’s a very good profile of Jack Dorsey in the recent New Yorker. If you use Twitter as a social media channel or use Square as a form of payment, you may know that he co-founded both. Forbes thinks he is America’s sixth-youngest billionaire.

The writer does a really good job of chronicling his pre-fame years, when his first start-up failed:

This was the era of rampant Web startups. Dorsey and [co-founder] Kidd pushed for a larger presence on the Internet, and wound up leaving the company in frustration. At the end of 1999, they moved to San Francisco and started a Web-based dispatch firm. (Dorsey withdrew from N.Y.U. a semester short of graduating.) Dorsey took on the look of a bike messenger, with dyed dreadlocks that ranged from bright blue to peroxide orange. Things did not go well at the new company. Its emphasis on honing technology ran counter to the board’s push for sales, and soon Dorsey was fired. The company failed during the dot-com bust.

Dorsey moved, in short order, to Richmond, Virginia, and Cambridge, Massachusetts, to be with women he was dating. Neither relationship worked out….

Not wanting to return to the grind of daily programming, he agreed to look after Kidd’s young daughter in exchange for room and board. He moved into a shed behind Kidd’s house, on the Berkeley-Oakland border. Babysitting was an unlikely job for an introverted man in his twenties, but he excelled at it….

He studied figure drawing after reading that Scott Morrison, a jeanmaker he admired, preferred designers who had such training. “He approached denim like it was a living journal,” Dorsey says. Later, he took classes in fashion design at Apparel Arts, in the Dogpatch neighborhood of San Francisco. He designed a pencil skirt and an asymmetrical one. He put them in a closet and, eventually, threw them out.

There you have it. Failed relationships, a shuttered company, and drawing. To Twitter and Square.

Isn’t America great?