Twitter Creator Jack Dorsey Almost Joined Facebook

By David Cohen 

JackDorseyTwitter Creator, Co-Founder, Chairman, and former CEO Jack Dorsey working at Facebook? It almost happened in 2007, New York Times Columnist and Reporter Nick Bilton wrote in his upcoming book, Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal, set for a November release by Penguin/Portfolio.

According to an excerpt from the book in The New York Times Magazine, when Dorsey’s role at Twitter was shifted from CEO to chairman and all of his power over the company was stripped, he spoke with Facebook Co-Founder and CEO Mark Zuckerberg and met with Vice President of Product Chris Cox, but the lack of a defined role at Facebook prompted him to look elsewhere:

When (Twitter Co-Founder and former CEO Evan) Williams asked Dorsey to send a companywide email setting Twitter’s goals, his first draft began with the subject line, “3 things I want for Twitter (Goals),” each goal beginning with an off-putting, “I.” Dorsey often tried to act as if he were in control, posturing that his actions were all part of a bigger plan, but employees saw him frequently pacing in frustration around South Park. He also habitually left around 6 p.m. for drawing classes, hot yoga sessions, and a course at a local fashion school. (He wanted to learn to make an A-line skirt and, eventually, jeans.) His social life, once virtually nonexistent, was becoming a distraction as venture capitalists wooed him at San Francisco Giants baseball games and parties throughout the city. On Dorsey’s watch, Twitter, which had never been completely upgraded from its prototype, was suffering major infrastructure problems that regularly knocked the site offline for hours at a time.

One summer afternoon, Williams asked Dorsey to meet him in the upper-floor conference room that the Twitter gang referred to as Odeo Heights. They opened the door to the small room, pulled back the chairs across from each other, and sat, hands clasped, as they had dozens of times before. “You can either be a dressmaker or the CEO of Twitter,” Williams said to Dorsey, “but you can’t be both.”

Dorsey seethed silently as Williams ticked off his grievances. But their dispute over Dorsey’s management illuminated a far deeper disagreement. Dorsey still believed that Twitter was primarily a service through which people could talk about themselves by updating their at-the-moment status. Williams worried that simply appealing to people’s egos would make Twitter too ephemeral. After seeing how users responded to a series of events that year, including an earthquake and a car crash, he was coming to a different conclusion — one that was much more in line with what (Twitter Co-Founder Noah) Glass had thought from the beginning. Twitter was a service for people to talk about what was going on around them, to share news and information. It was when Williams explained this concept — eventually saying Twitter was about “what’s happening” — that many in the industry, including those who once dismissed it, started to understand its potential.

Williams and Dorsey started meeting for weekly dinners to discuss the problems, but one night Dorsey became defensive. “Do you want to be CEO?” he said abruptly. Williams tried to evade the question, but eventually replied: “Yes, I want to be CEO. I have experience running a company, and that’s what Twitter needs right now.”

Dorsey raced home to try to figure out a plan for his resignation, but the Twitter board instead offered him a three-month window to fix the site and its issues. Not much changed, however, even as text bills mounted, and the site continued to crash. Before the three months were up, Dorsey recalled, (Spark Capital General Partner Bijan) Sabet and Wilson took him to a breakfast at the Clift hotel and told him that they were replacing him as CEO with Williams. Dorsey sat before a bowl of uneaten yogurt and granola as he was offered stock, a $200,000 severance, and a face-saving role as the company’s “silent” chairman. No one in the industry had to know that he was fired. (Investors would not want to be seen as pitting one founder against another anyway.) But Dorsey had no voting rights at the company. He was, essentially, out.

The timing of the departure was particularly fraught. For weeks, Facebook had been quietly exploring the possibility of buying the fledgling company, and while Dorsey was intrigued, Williams was not. The day after he was ousted, Dorsey called Zuckerberg to confidentially share the news. To Dorsey’s surprise, Zuckerberg asked if there was a way to prevent the firing, perhaps in order to save the deal. Dorsey assured him that there wasn’t, and Zuckerberg switched his plan from trying to buy Twitter to trying to hire Dorsey. So Dorsey met with Chris Cox, who ran Facebook’s product division, at a Philz Coffee in San Francisco. The discussions soon became more serious. But they didn’t have a specific role in mind. Zuckerberg wanted Dorsey to simply join Facebook in an unspecified capacity, and they would worry about a position later.

As he weighed Zuckerberg’s offer, Dorsey began considering the consequences. A jump to Facebook might indeed stick it to Williams, not to mention cripple outside investors’ confidence in Twitter. But Twitter’s embarrassment might prompt a leak about what had really happened. Of greater concern was the appearance of joining Facebook without a significant job title. Would that look like a step down? “Let’s just keep talking and see if we can find the right position for me,” he told Zuckerberg. “I’ve got to think about this.” He had bigger plans anyway.

Readers: How do you think Facebook would be different if Dorsey had joined the company?