Dorsey’s other venture, Square, the electronic payment service that allows anyone to accept credit card payments via their smartphone, is already processing $1 million in payments each and every day. But it’s the history of Twitter, and Dorsey’s relationship with fellow co-founders Biz Stone and (notably) Evan Williams that is of most interest.
Williams had expected his business to be a directory of podcasts. But when Apple incorporated one into iTunes, Odeo’s plans went out the window. In full reset mode, Williams asked his staff for new ideas, and Dorsey laid out his vision for Stat.us. SMS texting had just begun to take off in the U.S., so the time felt right. “Meanwhile, I was still doing this fashion thing,” remembers Dorsey. “I had about 10 classes where we built, from drawings to construction, skirts. Pencil, asymmetrical, mini. I wanted to make jeans, but you start with skirts because they’re easy. Then Twitter started taking off–and I never got to pants.”
Inside Odeo, Dorsey worked closely with several others on the project, then called “twttr.” Biz Stone, Dorsey’s close friend, did the design and user interface. Stone, aged 32 at the time, had written books on blogging and worked on projects that enabled extra-short posts. Like all great ideas, Twitter had many cooks, but no one disputes that the initial brainstorm grew out of Dorsey’s singular obsession. Shortly, they had a working product, and Dorsey authored the first tweet, cogent and Dorsey-esque: “Inviting co-workers.”
Odeo launched Twitter in July 2006, but it wasn’t until the following March that the world took notice. That’s when thousands of participants at the annual South by Southwest Interactive conference, in Austin, spontaneously began using it to swarm. The best parties that year were the ones people learned about on Twitter. The Twitter feeds defined the event for tech cognoscenti, and at Odeo it became apparent that Twitter ought to be spun off as its own company.
Williams had been struggling with Odeo’s investors and eventually bought the company back from them. Twitter seemed promising, but the firm was drifting. Employees were grumbling. Williams didn’t want to run Twitter, but instead to turn Odeo into an incubator for multiple businesses. He needed a C.E.O. But Dorsey, who had headed the venture so far, was just an engineer initially hired as a contractor. “I thought, It’s a risk, because he’d never even been a manager,” says Williams. “But Twitter wasn’t a huge deal at the time, and I thought, He has the vision. He’s got the technical chops. Let’s put him in charge.”
Dorsey got serious. “I took my nose ring out after our first round of financing,” he says, matter-of-factly. Twitter raised $5 million, largely from a single V.C. firm, Union Square Ventures. But managing a new company from Odeo’s wreckage was daunting. “Suddenly I became the boss of all my peers in a very damaged culture,” says Dorsey. “The morale was low.”
Twitter usage continued growing quickly–too quickly. Dorsey and his staff struggled to keep the service from going down. Looking back, Dorsey admits he was a flawed manager: “I let myself be in a weird position because it always felt like Ev’s company. He funded it. He was the chairman. And I was this new guy who was a programmer, who had a good idea. I would not be strong in my convictions, basically, because he was the older, wiser one.” Dorsey did a poor job explaining where he wanted the company to go.
“It just got a lot bigger a lot faster than anyone expected,” says Williams. “A year and a half later we’d raised $20 million, and the servers were crashing every day It wasn’t so much that the ship was sinking, but more ‘Great job, Jack–we’ve got to up our level of experience and lay some foundation for a much bigger organization.’ ” Others say the two were barely speaking by then, and in October 2008, Williams took the C.E.O. job for himself. Dorsey became chairman, but was no longer an employee.
He was devastated to be ejected again from a company that was building a product he’d conceived. “It was like being punched in the stomach,” he says in a rare moment of candor on the subject. Fred Wilson, who had joined Twitter’s board, puts a more benign spin on the breakup: “Ev and Jack are a little like John and Paul. They made great music together for a while, but then they both kind of got ambitious about things and didn’t see eye to eye anymore.”
Head on over to Vanity Fair to continue reading about who Dorsey reveres for design inspiration (no surprises), his ambitions for Square, and the lessons he learned about what went wrong, for him at least, at Twitter.
(Source: Vanity Fair.)
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