- A native of St. Louis, Missouri, Dorsey got his start in business at a young age by developing dispatch routing software used by taxi companies.
- With an estimated net worth of roughly $3 billion, his return to Twitter as CEO in 2015 was seen by many employees as similar to when Steve Jobs returned to Apple in the late ’90s.
- Since 2015, Jack Dorsey has served as the CEO of both Twitter and Square. Square’s business is booming, but Dorsey has yet to prove that he can turn Twitter into a thriving company.
- In addition to running two public companies, Dorsey also serves as a board member of Disney and the think tank Berggruen Governance Centerhas. He’s also hinted that he’d one day like to be mayor of New York City.
Many CEOs would say that it’s difficult to run one company. But for the last two years, Jack Dorsey has run two.
As the CEO of both Twitter and Square, Dorsey is one of the most famous and influential names in tech. And while Square’s business is doing better than ever, he’s also had the difficult job of steering Twitter through years of seemingly-constant executive turnover and lackluster growth.
Both CEO jobs present their own unique challenges, according to Dorsey.
“When I started, I just took in as much as possible and then I figured out what I need to focus on and what mattered and where I need to prioritize,” he said when recently asked about rejoining Twitter as CEO in 2015. “And both companies are in very different phases.”
“Square is something I built from day one and I know every single detail of that system,” he explained at The New York Times DealBook conference last month. “[With] Twitter, I had to learn a few things in my absence. I had to learn why we made decisions and what the principles were and how we might change those or how we might evolve those. Both required very different answers.”
While Dorsey benefits from the geographical proximity of Square and Twitter (both headquarters are across the street from each other in San Francisco), he manages his dual-CEO position by strictly regimenting his time during the work week. He spends mornings at Twitter and afternoons at Square. And in 2015, he said he begins his day at 5 AM and ends at 11 PM.
Dorsey explained more about how he manages his time during last month’s DealBook conference:
“I benefit from number one: A lot of structure. Number two: Realizing it’s not about the amount of time I spend at one thing but how I spend the time and what we’re focused on. And are we focused on the thing that truly matters most and is most important? Are we ignoring everything else, at least for now?”
“And then three: Do we have the right team around to do the work and make the decisions and move things forward. Square had been building that team for a long time. And we had to do some resets at Twitter throughout the company. It takes time for a team to gel. It takes time to understand how to collaborate with one another. Meanwhile, we have a lot of things that were not expected that I was coming into that we had to deal with.”
An early ousting – and a triumphant return
A native of St. Louis, Missouri, Dorsey showed an interest at a young age in developing dispatch routing software used by taxi companies. During a 2013 interview with “60 Minutes,” Dorsey explained how as a kid he would listen to police scanners. The short bursts of information he would hear over the airwaves laid the groundwork for the real-time news network that Twitter would eventually become.
The arc of Dorsey’s career at Twitter has been compared to Steve Jobs’s early fall from grace and triumphant return to Apple. After cofounding Twitter with Noah Glass, Biz Stone, and Evan Williams, Dorsey was ousted in 2008 after a power struggle with Williams. It was during this time that he cofounded the payments company Square.
He made his first return to Twitter as executive chairman in 2011. Dorsey then became CEO in 2015 when Dick Costolo stepped down from the role.
Dorsey’s rise to become CEO in 2015 after being kicked out of Twitter in 2008 was seen by many inside the company as similar to when Steve Jobs returned to Apple in the late 90s, according to one former senior Twitter employee. Like Apple when Jobs returned, Twitter’s business was faltering and employee morale was low.
Under Dorsey’s watch, Twitter has continued to weather stagnant growth and undergone multiple failed takeover bids. And while Square’s market value recently overtook Twitter’s for the first time, Twitter’s executive ranks have been a revolving door. Dorsey has an estimated net worth of roughly $3 billion, according to Forbes.
Current and former Twitter employees told Business Insider that Dorsey’s management style can lead him to be closely involved with projects when they’re deemed important but also appear aloof when an issue is raised that’s not in his current orbit. One high-level former employee recalled how Dorsey’s office was plastered with hundreds of variations of the Twitter logo when the company was undergoing a redesign several years ago.
“He’s comfortable high in the clouds and deep in the weeds,” the ex-employee said. “It’s the in-between that gets him tripped up.”
“My goal is to make sure we are building something that outlives me”
- Justin Sullivan / Getty Images
While Dorsey stays busy running two companies, he’s hinted in the past at having aspirations of eventually becoming mayor of New York City. He’s a known donor to the Democratic Party and rallied Twitter’s staff to raise $1.6 million for the American Civil Liberties Union in response to President Trump’s executive order on immigration. Outside of Twitter and Square, Dorsey serves as a board member of both Disney and the Berggruen Governance Center, a think tank dedicated to coming up with new ideas related to governance and globalization.
At Twitter, Dorsey’s main focus is currently on revamping the platform’s abuse and harassment safeguards after years of what people close to the company described as institutional negligence. And at Square, the payments company is focused on onboarding larger businesses for its point of sale system. A couple of months ago, Square filed to officially become a bank with the goal of offering more loans to small businesses.
During a presentation for advertisers earlier this year, Dorsey proclaimed that Twitter would continue to exist “for at least 10,000 years” – a grandiose statement seemingly meant to convey his commitment to the embattled company he helped create in 2006.
“My goal is to make sure that we are building something that outlives me and that endures and that continues to serve generations beyond me,” Dorsey said at the Dealbook conference last month. “That means I need to build structures that aren’t dependent entirely on me. That means I need to recognize leaders who can succeed me. That means we need to get our decision-making rigor and process into the very DNA of our companies.”