Jack Dorsey: The Determined Mind Behind Twitter and Square

Some entrepreneurs hold great ambitions in early childhood. They’re turning over sports cards on the playground or setting up a lemonade stand in front of the house. Not Jack Dorsey. As a kid, Dorsey never imagined himself as a CEO, entrepreneur, or public figure. In his flights of fancy, Dorsey saw himself as the Wizard of Oz, the man who pulled the levers from behind the curtain.

Who knew that the quiet boy who buried his head in maps and computers would one day found and lead Twitter and Square, becoming a multi-billionaire in the process? Oh, no one ever doubted that Jack Dorsey was brilliant — when Jack was a teenager, his boss, a man called Jim McKelvey, nicknamed him Jack the Genius — but he was just so unconventional!

Like all great business stories, though, Dorsey’s rise from shy computer nerd to global titan of technology came from his own determination, genius, and ambition, not from following anyone else’s lead.

Childhood Hobbies Shaped the Future

Born in St. Louis, Missouri in 1976 to Tim and Marcia Dorsey, Jack grew up in a comfortable, middle-class Catholic family. Tim Dorsey worked as an engineer of medical equipment and was employed at the company that made the mass spectrometer. Marcia served her family and community as a homemaker.

Young Jack’s family may have looked like the all-American household, but as a boy, Jack himself was anything but typical. For one thing, he rarely spoke to other people due to a pronounced stutter. Medical interventions proved futile, but Jack eventually cured his stutter by forcing himself to participate in oratory competitions.

Also unlike many kids who enjoy sports or video games, Jack’s childhood hobbies took a decidedly unusual turn. He loved maps, trains, and the voices on the police scanner. “I loved couriers,” he later said. “You had this transfer of physical information happening throughout the city and the world. Someone picking up the package, putting it in a bag, going somewhere, taking it out of the bag, giving it to someone else. I thought that was so cool. I wanted to map it, to see that flow on a big screen.”

By high school, Jack had joined the fledging computer club, which helped him turned this unusual collection of interests into a single idea — creating a dispatch software. He did it, and in fact, some taxi companies still use Jack’s program to this day. Now thoroughly in love with computers and the possibilities they offered, Jack graduated from Bishop DuBourg High School and enrolled at the Missouri University of Science and Technology.

College Proved a Dead End

Like his soon-to-be friend and peer, Mark Zuckerberg, Jack found that college stifled rather than fed his innovative spirit. Besides, when you’re spending your nights hacking into a bike messenger dispatching company, who has time for English 101? That’s exactly what Jack was doing. But as a white hat guy, Jack didn’t hack into Dispatch Management Services for illicit gain. In fact, he let the company chairman, Greg Kidd, know about the flaw in his company’s security. Kidd was so impressed, he offered Jack a job in New York.

“What I love about New York,” Jack would later tell interviewers, “is the electricity I feel right away.” He went to work with Greg Kidd and enrolled in New York University (NYU) to keep his traditionalist parents off his back. Apparently, neither his parents’ expectations nor the electricity of New York proved reason enough to stay in school.

Jack dropped out of NYU before completing his degree. Besides, Greg Kidd could see that New York wasn’t the cradle of the technological revolution. California was. So he invited Jack to join him there. Despite leaving New York without a diploma, Jack’s experience at NYU wasn’t entirely in vain. While there, he’d hit up on an idea to share short messages with his friends using the internet.

 

Getting Started in California

In 1999, Jack moved to California to join his mentor Greg Kidd. The two men intended to co-found a startup that would dispatch taxis, couriers, and emergency services over the internet. Jack threw himself heart and soul into the new company. In his off time, though, Jack also began tinkering around with a new idea that he’d come up with while blogging on LiveJournal, an early platform for bloggers.

Wouldn’t it be great, Jack thought, if he could update his friends about his doings in short, live spurts instead of waiting to write a whole blog post after the fact? The idea fascinated him so much that Jack built a simple prototype that let him keep his friends abreast of his life and happenings on their BlackBerries or through email. That prototype turned out to be the precursor of Twitter.

Jack’s time with the new dispatch company didn’t prove as fruitful as his off-season work did, however, and in 2002, the board fired him. Dot coms everywhere were going belly up, and Silicon Valley’s once-bright image as the shining wave of the future was looking a bit tarnished. So, Jack headed home to Missouri.

In true Jack fashion, he handled his disappointment by getting an S-shaped tattoo, a nose ring, and a blue dye job in his hair. He also got licensed as a massage therapist. Of course, being Jack, he didn’t set up a massage shop; instead, he tried to invent a chair-massage service to help programmers cope with aching wrists. It went nowhere.

 

From Failure to Freelancer

Failure figures into the story of every great entrepreneur, and Jack was no exception. Back in St. Louis, Jack had little more than his massage therapy license and a history of failed technology innovations on his resume. He didn’t even hold a college degree. Maybe the unconventional road didn’t lead to success, after all? Maybe the road to success ran straight through ordinary? It was starting to look that way.

But Jack Dorsey could never be ordinary. After freelancing — and massaging — to make ends meet in Missouri, Jack decided he’d be better off back in California. He agreed to look after Greg Kidd’s children in exchange for free living space in the Kidd family’s backyard shed. Around the babysitting gig, Jack found time to apply to a job listing he saw on Craig’s List, a chance to build a ticketing app for tourists going to Alcatraz. He took it.

But working for someone else, even short-term, wasn’t in Jack’s DNA. He itched to get back into what he loved. And an opportunity was waiting for him at the Caffe Centro in the South Park section of San Francisco.

Early Days of Success

The freelance jobs were running thin, and the babysitting gig didn’t offer a future. So Jack applied to work at a shoe store, but his application got rejected. He decided to drown his sorrows in a cup of joe at Caffe Centro. That’s where he literally bumped into Evan Williams, the tech entrepreneur who had sold Blogger to Google. Evan told Jack about a new company he was setting up, a podcasting production enterprise called Odeo.

Jack, in turn, pitched Evan his idea to combine easy instant messaging with broad reach to Evan and his business partner Biz Stone. The two men liked it, and they liked Jack, but they weren’t as sure of his idea as they were of theirs. So they hired him to work at Odeo as a low-lever coder.

Odeo, however, failed to neutralize its major competitor, Apple Podcasts, and Evan finally sold the company to Sonic Mountain. In 2006, seeing the handwriting on the wall for Odeo, Evan and Biz turned their attention back to Jack Dorsey and his quirky idea. Maybe — just maybe — the kid was on to something. Another Odeo co-founder, Noah Glass, and a German engineer named Florian Weber worked with Jack to prototype his idea. In two weeks, they had an MVP. And at 12:50PM on March 21st, 2006, Jack sent the first public tweet: “just setting up my twttr.”

Twittering

Noah Glass had plucked the name “Twitter” out of the dictionary, but Odeo executives though “twttr” would be cooler, since Flickr had made a splash using the same spelling convention. In October, the new company set up operations and named 30-year-old Jack Dorsey as CEO. Now an executive, Jack removed his nose ring and set to work leading a fast-growing social media company. And “fast growing” hardly describes the situation.

Twitter’s ramp up was off the charts. In 2007, the company saw 400,000 tweets per quarter. In 2008, that number grew to 100 million tweets per quarter. The site was popular externally but struggled to keep pace with growth internally.

Never at his best in a conventional role, Jack was struggling with his new responsibilities. He loved yoga and fashion more than hard-nosed business. So Evan Williams assumed the CEO role, and Jack moved into what was described as a “passive chairman role and silent board seat.” While Twitter flourished under a steadier hand, Jack was floundering. At first, he toyed with the idea of going to work for his friend Mark Zuckerberg at Facebook.

When that didn’t work out, Jack began a new venture in 2009. He called it Square.

 

Founding Square

Square is a payment system that aggregates merchant services and mobile payments in a single service. Jack got the idea for Square from Jim McKelvey, his old boss from St. Louis days, who said he needed something like Square when he couldn’t sell a piece of art out of his apartment. The concept gained traction in its target market.

Within 10 years, small business owners had downloaded Square 33.5 million times and were using it to accept credit card payments, manage inventory, track sales, and obtain financing. “I think Twitter is the future of communications and Square will be the payment network,” Jack said.

Square was as big a success as Twitter in its own way, but Jack still smarted over his treatment at the social media company he had founded and that had made him a billionaire.

Feeling like Steve Jobs, who was famously dismissed from Apple, Jack began to adopt Jobs’ personal characteristics. He even wore the black turtlenecks that Jobs made famous, snagged Apple employees, and quoted Gandhi and the Beatles. The public criticized Jack for aping Jobs, but Jack knew what he was doing. Jobs, after all, had been dismissed from Apple, founded Pixar, returned to Apple, and then ran both companies simultaneously. Jack believed he could do the same. He was right.

In 2015, Twitter’s board replaced Evan Williams with his COO Don Costolo. Jack returned as Executive Chairman. He would be CEO again within months.

 

The Return of the King

Twitter needed Jack Dorsey’s creativity more than ever. After blasting past 600 million tweets per day, the number had dropped by nearly half. And while Don Costolo had proven to be an exemplary business executive, he could not articulate Twitter’s overall vision or differentiate it from other media platforms. But Jack could. “Twitter has to be the most powerful microphone in the world,” he said.

Jack Dorsey seems to be the CEO who can make turn that vision into reality. He’s more comfortable being himself this time around, keeping the nose ring, growing a mountain-man beard, and talking openly about his unusual diet (he eats once a day and fasts on weekends). He’s also turning Twitter around. So far, Jack has helped Twitter to purchase Niche, Periscope, and an artificial intelligence startup called Magic Pony. He’s also led the company through a successful IPO and a popular redesign.

Square continues to flourish as well, and Jack’s presence at both companies gives investors confidence that neither corporation will grow too ordinary. The man walks five miles to work three days per week and spends his other two workdays at home, after all, and he once ate a goat killed and served by Mark Zuckerberg.

The quirky boy from St. Louis has found his footing as both an innovator and a leader. He’s brought two mega-successful companies to fruition and become one of only a handful of self-made billionaires. Who knows what Jack Dorsey will make next? Whatever he devises, it’s sure to defy convention.