Dorsey began programming while attending Bishop DuBourg High School in St. Louis. At age 15, Dorsey wrote dispatch software that is still used by some taxi companies.
Source: Bio.
When he wasn't checking out specialty electronics stores or running a fantasy football league for his friends, Dorsey frequently attended punk rock concerts.
Source: The Wall Street Journal
Like many of his fellow tech billionaires, Dorsey never graduated college, though he briefly attended Missouri University of Science and Technology and transferred to New York University before calling it quits.
Source: Bio.
In 2000, Dorsey built a simple prototype that let him update his friends on his life via BlackBerry and email messaging. Nobody else really seemed interested, so he put away the idea for a bit.
Source: The Unofficial Stanford Blog
He got a job at a podcasting company called Odeo, where he met his future Twitter cofounders. Odeo went out of business in 2006, so Dorsey returned to his messaging idea, and Twitter was born.
On March 21, 2006, Dorsey posted the very first tweet.
https://twitter.com/mims/statuses/20
just setting up my twttr
Dorsey and his cofounders Evan Williams and Biz Stone bought the Twitter domain name for roughly $7,000, and Dorsey took out his nose ring to look the part of CEO. He was 30 years old.
But Dorsey was already on his way out from Twitter. By 2008, Williams had taken over as CEO, and Dorsey transitioned to chairman of Twitter's board. Dorsey immediately got started on some new projects. He invested in Foursquare and launched a payments startup called Square that lets small business owners accept credit card payments through a smartphone attachment.
In 2011, Dorsey got the chance to interview President Barack Obama in the first ever Twitter Town Hall.
Source: Twitter
He might have been worth more had he not given back 10% of his stock to Square. This helped out Square employees, giving them more equity and stock options. It was also helpful in acquiring online food delivery startup Caviar.
Source: Business Insider and Caviar
Dorsey does not often flaunt his billions and reportedly even takes the bus to work. He told the New Yorker he uses the commute to do market research: "I saw the rise of Instagram here. I saw the rise of Vine and Snapchat, and how many more people were using Facebook versus Twitter, and it’s amazing. Like, look — anyone reading magazines, newspapers, books?"
He does own a BMW 3 Series, but he doesn't drive it all that often. "And now he’s able to say, like, 'The BMW is the only car I drive, because it’s the best automotive engineering on the planet,' or whatever," Twitter cofounder Biz Stone told the New Yorker in 2013.
Source: The New Yorker
He apparently does not have a desk; he just works on an iPad. He's also a licensed masseur.
Source: CBS News and The Wall Street Journal
In the early days of Twitter, Dorsey aspired to be a fashion designer, and he's still considered by many to be one of the most stylish men in tech. He regularly dons leather jackets and slim suits by Prada and Hermès, as well as Dior Homme reverse-collar dress shirts, a sort of stylish take on the popped collar.
He told the New Yorker he has a strict schedule for eating out. On Monday, he goes to Aziza, on Tuesday he goes to Zuni, on Wednesday it's Mint, and on Thursday it's Tiburon. "I’m always looking for the one thing for me, rather than tasting everything I can," he said.
https://twitter.com/mims/statuses/329417703427305472
Dinner with my favorite entrepreneurs @levie @8en and @dickc. https://t.co/PXhJM6n608
He also loves art and design.
https://twitter.com/mims/statuses/515695836966445056
For @aiww https://t.co/cuiSlqzxA8
Dorsey frequently travels all over the world and shares his photos with his more than 3 million Twitter followers.
https://twitter.com/mims/statuses/338615743816032257
https://t.co/aqMK29eSNr
Flying is one of his favorite hobbies.
https://twitter.com/mims/statuses/351425472388808704
I love flying. https://t.co/fw1kECtZiT
He also reportedly paid $9.9 million for this seaside house on El Camino Del Mar in the exclusive Seacliff neighborhood of San Francisco.
Source: Business Insider
That view is certainly nothing to scoff at.
https://twitter.com/mims/statuses/336192833188937728
https://t.co/g6ro40Gckj