Napoleon had two reigns as emperor of France, but for Jack Dorsey and Twitter, third time's a charm.
As Twitter’s newly appointed permanent CEO, Dorsey will helm an organization that he not only cofounded but steered from the top (and been ousted from) twice before.
With Twitter’s growth languishing, many are hoping that Dorsey will lead the comeback, giving the company a shot of energy and vision.
But a look back at Dorsey’s previous stints at the company offer a cautionary footnote to the feel-good "Jack's Back" narrative. Dorsey’s first brief term as Twitter CEO, between April 2007 and October 2008, ended in a bitter boardroom coup. And his much-heralded return to the company as product czar in 2011 was so problematic he was “quietly shown the door,” according to one insider.
“When he came back it was such a train wreck,” is how the person describes Dorsey’s 2011 return to Twitter. Among the biggest problems were his difficulty getting along with others and inconsistent product plans.
Since that time, Dorsey has run digital payments company Square, which he also founded, as its CEO. According to a recent profile in Recode, Dorsey has matured a lot as a leader during the past few years. The 38-year-old Dorsey is much better at delegating, communicating, and motivating employees, according to Recode.
So it’s possible that the new Dorsey could fit in much better at Twitter than his past attempts. And some people believe that Dorsey is the best possible choice to lead Twitter at this time. But it’s worth keeping in mind some of the problems that marred his previous stints at Twitter as he launches his latest comeback.
Twitter's first chief
When Dorsey was first CEO in 2007 and 2008, he was much younger and inexperienced.
"Jack is crazy-smart and a product visionary and all that," one person familiar with Jack's early work there told Business Insider in 2013. "But Jack wasn't ready to be CEO at that time."
Dorsey still had dreams of being a fashion designer at the time, and he'd often leave work to take night classes, according to Nick Bilton’s book "Hatching Twitter." He also left early for art and yoga classes. His extracurriculars eventually became such a distraction, Bilton reported, that Williams eventually sat down with Dorsey and said, "You can either be a dressmaker or the CEO of Twitter. But you can't be both."
Dorsey also struggled making the transition from his role as an engineer to being the boss. He wasn't leading teams well, and employees weren't happy working for him. He wasn't hiring new people fast enough.
The site constantly crashed, making the Twitter "fail whale," which appeared when the site went down, a more prominent mascot than Twitter's blue birds. In 2007, the year Dorsey became CEO, Twitter's total downtime was six days. The constant crashing was a source of stress.
In the end, he was replaced as CEO by cofounder Evan Williams after seven months on the job.
Back as product czar
Dorsey’s second coming was equally contentious.
When Evan Williams was in his turn ousted and replaced as CEO by Dick Costolo in 2011, Dorsey was called back to duty to oversee product and to serve as Twitter’s executive chairman.
It had all the makings of a great comeback story, but it didn’t go according to script.
Dorsey quickly caused friction with other employees. He replaced many valuable employees who were perceived as having been loyal to Williams and he was not communicative with people at the company, according to Recode.
One of the biggest product changes he made, a Discover tab to help users find news and other content on Twitter, was gradually de-emphasized and eventually shuttered. After a marketing VP was hired and then left after three months during Dorsey’s tenure, Dorsey himself began to oversee the marketing functions, according to a report in TechCrunch at the time.
During Dorsey’s time overseeing Twitter’s brand, the company ran its first, and only, television commercials. The 15-second ads were produced by a marketing firm run by an ex-Apple executive in which Dorsey was also an investor. The arrangement raised eyebrows and caused whispers within the company, says the Twitter insider. Twitter ultimately disclosed the arrangement in the prospectus for its 2013 IPO, noting it had paid a total of $2.2 million to West Studios, a firm in which Dorsey had a direct ownership interest.
According to one former Twitter insider, Dorsey was eventually “quietly shown the door.”
After a 2012 article in The New York Times described some of the problems with Dorsey’s managerial style, Dorsey published a blog post acknowledging that he was no longer involved with Twitter. Here's what he said:
In Spring of 2011, Dick asked me to take an operational role overseeing product, design, and brand. Our shared goal was to get those organizations back under him as soon as possible, simply because it was the right thing to do for the company. We moved all of my reports back under him in January of this year after leadership was firmly in place. This allowed me to focus on refining our brand and logo, to work more with Dick and the leadership team on our direction forward, and ultimately return the majority of my time to Square, where I’m CEO. I’m back to going to Twitter on Tuesday afternoons, something I started before taking the interim operational role.
