Jack Dorsey charts new chapter for Twitter, Square

SAN FRANCISCO — First, Twitter CEO Jack Dorsey got straight to the point, telling employees in a frank memo he was cutting hundreds of jobs so he could put the social media company on a “stronger path to grow.”

The next day, before Silicon Valley could catch its breath, Dorsey put on his Square CEO hat, announcing the mobile payment startup’s plans to go public.

And it was only his second week as a dual CEO.

Soft-spoken yet persuasive, Dorsey — who was ousted as Twitter CEO in 2008 amid complaints about his management style — emerged as a wild card in the social media company’s search for its permanent leader, convincing board members in a few months he could accomplish what many tech moguls never attempt to do. Even in Silicon Valley, where entrepreneurs take risks and investors pump money into “unicorn” startups valued at more than $1 billion, Dorsey’s role leading two companies simultaneously is viewed as a roll of the dice. Twitter, Square and Dorsey, who was named Twitter’s permanent CEO on Oct. 5, declined to comment for this story.

The 38-year-old billionaire typically stays out of his employees’ way unless something goes awry, using data to guide decisions, former employees say. He doesn’t have a desk at Square and engages in face-to-face conversations with his workers, scribbling notes in a Moleskine notebook and rapidly firing off emails on both an iPhone and Android.

“One of the most impressive changes I’ve seen in Jack is his aptitude for analytics. Everybody knows the image of Jack the gifted speaker, the quirky guy, the artist, the tattooed design geek. But perceptions lag reality,” J. Bryan Scott, who led analytics, risk and a business financing arm at Square from 2011 to 2015, said in an email.

Scott recalled his one-on-one job interview with Dorsey on a Sunday afternoon in 2011. Walking from Square’s headquarters to Sightglass Coffee, Dorsey asked Scott a single question: “What are the risks to us hiring you?” The question was simple, yet clever and rapport-building, Scott thought, especially since the job candidate had probed Square leaders earlier about strategy and risks.

“He was looking for humility, earnestness and salesmanship. He unequivocally trusted his team’s opinion of me for everything else,” said Scott, who left Square this year to start his own company. “I like leaders who trust their team. I started work the next day, on Monday.”

The tall and bearded chief executive, who once dyed his hair blue and wore a nose ring, has spent his life going against the grain, defying even his own childhood expectations.

On his forearm is a black tattoo of an elongated S, which Dorsey told The New Yorker represents three things that interest him: an integral in calculus, an F-hole in a violin and what he called the most beautiful bone in the human body, the collarbone.

Growing up in St. Louis, Dorsey never wanted to be an entrepreneur or a computer programmer, he has said, aspiring instead to become a sailor, tailor or even a surrealist painter.

His mom ran a coffee shop and his dad, Tim, opened a pizza restaurant and then a mass spectrometer business, career moves that may have ignited his entrepreneurial spirit, according to an essay his mom, Marcia, wrote in The Wall Street Journal in 2013.

To Dorsey, who is unmarried, running a business is more than just about making money. He talks about technology as if he’s creating a work of art, emphasizing the importance of the creative process, tugging at a customer’s emotions and often bringing up the construction and design of the Golden Gate Bridge.

“The most important thing for me to do is to see a picture of where I want to go, see a picture of what I want to do in the world, and then figure out how to work backwards from that,” Dorsey told Stanford Graduate School of Business students in 2013.

His high school friends, drawn to Dorsey because of their mutual love for music, recalled he was quiet and laid back, but that he also had a sense of humor, even jokingly dressing up as his religion teacher one day. Overcoming a speech impediment as a child, Dorsey didn’t stray from public speaking and would deliver the morning news in a television show broadcast to his Bishop DuBourg High classmates.

“We weren’t picked on by any means. But we weren’t jocks or lady’s men or anything like that. Just a bunch of misfits, some who were into music,” said Tim Brouk, now a media specialist at the Purdue University College of Science.

Even then, Dorsey was fascinated by maps and well versed in technology, reciting facts like a walking encyclopedia. “We used to go to music stores and he could tell you what any of the devices did. He taught me the whole background of keyboard synthesizers at one point,” said Charlie Kelly, who works at a health care IT company.

After dropping out of college, brief stints studying fashion design and massage therapy, starting a Web-based dispatch company and more moves in between, Dorsey helped start the microblogging site Twitter with Evan Williams, Biz Stone and Noah Glass in 2006.

He was the company’s first CEO and the man behind Twitter’s 140-character limit. But he struggled to keep the site from crashing as complaints about his management piled up, including his tendency to leave work at 6 p.m. to attend fashion design, drawing and yoga classes, according to the book “Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal” by Nick Bilton. In 2008, he was booted from the position in what he later told Vanity Fair felt like being “punched in the stomach.”

Between the firing and his return to power at Twitter, Dorsey grew as a leader, observers say, teaming up with Jim McKelvey in 2009 to start Square, a company aimed at making it easier for businesses to accept credit card payments through the tap of a mobile app. He has given more than 15 million shares of Square back to the company and the Start Small Foundation, a new organization he created to help artists, musicians and local businesses in underserved areas. But Dorsey didn’t forget about Twitter, recently announcing that he’s giving one-third of his 22 million shares, valued at $200 million, to the company’s employee equity pool.

Elite Audio Systems, an electronics store that also houses a coffee bar, was one of Square’s early adopters, but when the business tried to use the white credit card reader it wasn’t working.

One day three men walked into the store, asking to pay using Square, said store owner Michael Woods. He quickly learned from his wife that one of them was Dorsey, whom he often spotted walking between Square and Twitter on Market Street.

“The very next day we had a crew over here and Square was working. He made sure that it worked,” Woods said.

Amid the fame and fortune, Dorsey still finds time to tweet to his family and even returned to his hometown in August 2014 to march in the Ferguson protests with his parents and friends. Few recognized him. One protester asked the billionaire to snap a photo of him in the crowds, then wondered afterward if he was on Twitter.

Though he does take a lot of Vine selfies, Dorsey’s Twitter bio isn’t about himself. Instead, there’s a hashtag promoting the Malala Fund, an organization aimed at empowering girls through education.

“He could have been a spoiled kid, and that’s not at all who he was,” said St. Louis Alderman Antonio French, who marched in the protests alongside Dorsey. “He seemed to be a very humble person who despite his success at a relatively young age is still inspired to reach higher and do even bigger things,”

Contact Queenie Wong at 408-920-2706. Follow her at Twitter.com/QwongSJ.