11 min read.Updated: 28 Oct 2020, 12:24 PM ISTKirsten Grind, The Wall Street Journal
The CEO’s management style, delegating most major decisions while pursuing his personal passions, faces one of its biggest tests
Twitter Inc. CEO and co-founder Jack Dorsey found himself in the hot seat two weeks ago, when with little explanation the platform he leads began blocking its millions of users from sharing links to a pair of New York Post stories about Joe Biden’s son, Hunter Biden. Within hours, lawmakers said they would subpoena Mr. Dorsey to explain his decision.
But Mr. Dorsey wasn’t involved in the initial discussions about the move, according to people familiar with the matter. After a public outcry, he posted on Twitter that blocking link sharing with no context from the company as to why was “unacceptable."
Mr. Dorsey’s absence from such a key decision isn’t unusual. At both Twitter and Square Inc.—the financial-technology firm where he is also chief executive—current and former employees say he is hands-off to the extreme, delegating most major decisions to subordinates in part so he can pursue his personal passions.
That management style now faces one of its biggest tests ever, amid growing pressure to address the company’s problems. Starting tomorrow, Mr. Dorsey is scheduled to testify in Washington, along with other tech CEOs, about their handling of the Post articles and other issues related to content moderation.
The enigmatic Mr. Dorsey has worn a nose ring, completed a 10-day silent retreat in Myanmar in 2018 and has said he takes multiple ice baths a day. He has an intense curiosity about people and social issues across the political spectrum, which even his critics say is genuine. Among the many people he has developed relationships with are Scott Adams, the creator of the Dilbert cartoon and a prominent conservative voice on Twitter, and DeRay Mckesson, a civil-rights activist and leader of Black Lives Matter.
Mr. Dorsey has maintained a cordial correspondence with Charles C. Johnson, who was once labeled by the left-leaning Mother Jones magazine as Twitter’s “most infamous right-wing troll" and is permanently banned from the platform.
“Jack Dorsey is a beautiful man with the impossible job of making everyone happy," Mr. Johnson said.
Investors and some employees say Mr. Dorsey should be more focused on solving the major problems facing Twitter, which is valued at $38 billion and has become a central cog in how Americans express themselves online.
At Twitter’s annual shareholder meeting in May, investors questioned Mr. Dorsey about his split time. “When will Twitter obtain a full-time CEO?" one asked. Another added: “Why do you, Jack, think you are the right leader for our company?"
“To me, this is not a function of time, it’s a function of prioritization," Mr. Dorsey said.
Twitter declined to make him available for comment.
Mr. Dorsey has led both Twitter and Square to strong financial performance. Twitter’s stock is up more than 70% since Mr. Dorsey took over as CEO for the second time in the fall of 2015, and is trading around $50 a share today. Square, which Mr. Dorsey co-founded and has led as chief executive since 2009, has seen its stock grow around 14 times since its 2015 initial public offering, to about $170 a share today.
The problems Twitter is grappling with include the proliferation of hate speech, harassment, bullying, disinformation and accusations that it is censoring some users.
Mr. Dorsey has acknowledged these issues and repeatedly pledged to address them. Current and former employees say he often acts at a glacial pace. Twitter took almost two years to increase the 140-character limit on tweets after Mr. Dorsey began asking about it in 2015. Employees developed dozens of variations internally for how to get rid of the limit, but were delayed as they waited for Mr. Dorsey to make a decision, according to people familiar with the efforts.
Earlier this year, the activist hedge fund Elliott Management Corp., unhappy with Mr. Dorsey’s laissez-faire approach to management and lack of attention to Twitter, placed one of its own investors on the company’s board of directors.
The activist is treating this year as a probationary period for Mr. Dorsey, according to people familiar with the matter.
Twitter’s chief financial officer, Ned Segal, has told investors and analysts over the past 18 months that the company is working on acting more quickly. In the past year, the company has rolled out more initiatives than in the past.
Mr. Dorsey’s style is a sharp contrast to that of Facebook CEO Mark Zuckerberg, who has taken a hands-on role in preparing his rival social-media platform for the coming election, including by signing off on high-profile enforcement decisions.
Facebook has about 1.8 billion daily users across all of its products, compared with Twitter’s 186 million daily users.
Both Messrs. Dorsey and Zuckerberg are scheduled to testify before a Senate committee on Wednesday, along with Alphabet Inc. CEO Sundar Pichai, about their policies for moderating content. Mr. Dorsey is separately scheduled to testify along with Mr. Zuckerberg before another committee in November about their handling of the New York Post article and the election more broadly.
Mr. Dorsey has said that as leader of two publicly traded companies, he sees his role as asking questions of as many different people as possible. His contacts include Mr. Johnson, a former writer for conservative media outlets including the Daily Caller.
Mr. Johnson was permanently banned from Twitter in 2015 for posting a call for donations for “taking out" Mr. Mckesson, the civil-rights activist, according to a copy of the tweet. Mr. Mckesson saw the tweet as a threat, as did Twitter. Mr. Johnson said the tweet was taken out of context. He later unsuccessfully sued over the ban.
He posted online in at least one instance doubts about the scope of the Holocaust, and was photographed making a symbol for white power. Now largely a tech investor, Mr. Johnson said that he isn’t a Holocaust denier or a white supremacist.
Mr. Dorsey wasn’t CEO at the time of the ban but Mr. Johnson said they got in touch afterward, through mutual friends. Mr. Johnson said the two have discussed the teachings of Satya Narayan Goenka, an Indian teacher of Vipassana meditation.
In June, Mr. Dorsey responded to a series of Signal messages from Mr. Johnson to tell him that Twitter wasn’t censoring conservative voices, and that he had spoken with President Trump about the issue. As for Mr. Johnson’s ban from Twitter, Mr. Dorsey said he was “working on [a] path forward," according to the messages.
After an introduction through Mr. Johnson, Mr. Dorsey invested an undisclosed amount in San Francisco-based ClearLabs, a startup that is trying to use genomics to identify Covid-19, according to Mr. Johnson and people close to the deal. Mr. Johnson said he recently suggested Mr. Dorsey invest in several companies where he is also an investor, including Clearview A.I., a tech startup that has been questioned by lawmakers over the application of its facial-recognition software.
Mr. Dorsey, 43 years old, grew up in St. Louis, Mo. He has said that his father is a Republican, his mother is a Democrat, and that he is somewhere in between. Both his parents use Twitter, and his mother often tweets “Good Morning!" to start her day.
A billionaire several times over, Mr. Dorsey sports a large tattoo of the S-shaped integral symbol used in mathematics on his left arm and typically wears black T-shirts and hoodies. He was fired as Twitter CEO in 2008 in part for leaving work early to go to yoga classes.
He often walks miles across San Francisco from his home in the mansion-studded Sea Cliff neighborhood to his office downtown. Fascinated by the minimalist style deployed by the late Apple Inc. founder Steve Jobs, he owns only a handful of pieces of furniture.
Mr. Dorsey announced on Twitter at the beginning of the coronavirus pandemic that he would give away $1 billion, or roughly 30% of his net worth, to charity, starting with efforts toward global Covid-19 relief.
The rapper Kanye West said in a 2018 interview that Mr. Dorsey is his “favorite founder," and the executive spent time this summer with Jay-Z in the Hamptons.
“There’s a part of him that people don’t see, which is his curiosity outside of tech," said Mr. Mckesson. “He’s deeply curious about how to make an impact with regard to race and justice," he added.
In 2014, Mr. Mckesson met Mr. Dorsey on the street in Ferguson, Mo., where Mr. Mckesson was protesting the death of Michael Brown, the Black teenager who was shot by a white police officer.
Mr. Dorsey invited Mr. Mckesson to join his family’s Christmas Day tradition of meeting at a coffee shop in nearby St. Louis.
Mr. Mckesson said he reaches out directly to Mr. Dorsey with issues related to Twitter or Square, and tells people who want an introduction to do the same.
“Jack approaches problems from a spirit of possibility, which is great," Mr. Mckesson said. “He doesn’t run from ‘the big idea.’ "
Mr. Adams, the Dilbert creator, called Mr. Dorsey a “seeker" who is genuinely interested in the world views of others.
A prolific user of Twitter and its video app, Periscope, Mr. Adams said he connects with Mr. Dorsey about site-specific issues, but also to talk about books. He said he believes that Mr. Dorsey struggles with coming to terms with his own success, as does Mr. Adams.
“He will never be done trying to figure out this reality thing," Mr. Adams said.
In early 2019, as Twitter came under attack for its treatment of conservatives, Mr. Dorsey gave interviews to a series of conservative media hosts, including Joe Rogan and Sean Hannity.
Some Twitter employees and executives objected to the move, saying that some of the shows were more invested in stoking claims of anticonservative bias at Twitter than presenting facts, and didn’t make good-faith efforts to find common ground, those people said.
Over the years, Twitter has faced growing calls from users to address harassment on its platform that targeted women and people of color, such as when the actress Leslie Jones was attacked with racist and sexist memes.
Mr. Dorsey also faced internal opposition in 2016 when he suggested bringing Mr. Mckesson on to the company’s board, according to people familiar with the matter. That same year, he tried unsuccessfully to give a board seat to Malala Yousafzai, a Pakistani activist who was a co-recipient of the Nobel Peace Prize but had little business experience.
Employees at both Twitter and Square have complained about Mr. Dorsey’s absences, particularly as it has slowed down decision-making, current and former employees and executives say.
As Square prepared to go public in 2015, Mr. Dorsey took on the additional job of leading Twitter. He defended his frequent absences by comparing himself to billionaire Elon Musk, who also runs two companies, Tesla Inc. and SpaceX. “You are no Elon Musk," one Square executive told Mr. Dorsey.
The issue of what some called “absentee management" appeared to come to a head after Mr. Dorsey announced on Twitter in late 2019 his intention to work remotely from Africa while still running both companies.
After a trip there to study how people in Africa used the internet, Mr. Dorsey decided he wanted to immerse himself in a country where the web was still new, said one person familiar with his thinking.
Mr. Dorsey has long been a proponent of working from home, pushing for employees to be able to work remotely even before the pandemic, this person said. The company announced in May that staff would be able to work from home permanently if they chose, well before other major tech companies followed suit with similar announcements.
The Africa plan, however, sparked the ire of Elliott, which had taken a roughly $1 billion stake in Twitter. In October 2019, Twitter’s stock price dropped 20% in a single day after a disappointing earnings report.
Elliott undertook a quiet review of Twitter’s leadership, with current and former executives telling the investor about the challenges of Mr. Dorsey’s leadership style and his juggling of two companies, according to people familiar with the matter.
Elliott threatened to oust Mr. Dorsey. Employees defended him on Twitter with a #webackjack campaign. Mr. Musk, a frequent user of the platform, also tweeted his support. The activist compromised by taking a board seat, along with another investor, Silver Lake.
Egon Durban, co-chief executive of Silver Lake, said in a written statement he has developed “a deep appreciation for Jack’s leadership and strategic vision" and looks forward to continuing to work with him.
When the New York Post issue erupted on the platform in mid-October, Twitter initially said it was blocking users from posting links to the articles due to a potential violation of its rules about hacked materials.
The Post said its stories were based on email exchanges with Hunter Biden found on a laptop given to allies of President Trump by a computer-repair person. News Corp, the corporate parent of Wall Street Journal publisher Dow Jones & Co., also owns the New York Post. Mr. Biden’s campaign has denied allegations made in the articles.
Twitter then quickly reversed course by changing its antihacking policy from 2018. The company said it would no longer remove what it considers “hacked content," unless it’s directly shared by hackers. It also said it would label such tweets.
Mr. Dorsey did provide guidance on those policy changes, according to people familiar with the decision. He usually doesn’t weigh in on user-specific enforcement actions, instead trusting his team to make them.
In an investor conference earlier this year, Mr. Dorsey defended his workload. “I have enough flexibility in my schedule to focus on the important things and I have a good sense of what is critical on both companies," he said.
This story has been published from a wire agency feed without modifications to the text