The Untold Truth Of Jack Dorsey

You might not recognize the name Jack Dorsey, but you definitely will recognize his greatest achievement: Twitter. Since 2015, Dorsey — one of Twitter's co-founders — has held the CEO role in the social media company. Plus, he's also the co-founder and CEO of Square — a credit card payment service. This "43-year-old multibillionaire is one of the only CEOs on the S&P 500 who oversees two public companies, Twitter and Square, with more than 8,000 employees, and is an angel investor or adviser to start-ups," Vanity Fair summarized in 2020. What else is the man good at? According to his Forbes bio, Dorsey is also a certified masseur.

The success of this rockstar in the tech world has spilled over into other industries as well. And you'll be surprised at one of Dorsey's early passions. But not everyone approves of this CEO's story, proving it can be lonely at the top.

What would you do if you were in charge of Twitter? In much more than 280 characters, this is the untold truth of Jack Dorsey.

What was life like before Twitter? In the early aughts, a few smart tech minds started thinking of connecting people online. Facebook already existed at the time, but these four men — Jack Dorsey, Noah Glass, Evan Williams, and Biz Stone — dreamed of a different experience. In 2006, Dorsey and Glass talked about a solution so people "could feel less alone with a steady stream of conversation percolating online," per The New York Times. The two guys presented their idea at the Odeo office the next day, a podcasting company where the four worked. The big idea was "a status updater that could be used to connect friends." Right away, "Glass soon took charge of the project" while "Dorsey and another programmer, Florian Weber, did the coding." As the project developed, the service needed a name. One original idea of "Friendstalker" was fortunately removed from consideration. Glass searched through a dictionary and found the perfect word to summarize the future chatter of users: twitter. 

The collaborative effort of all the co-founders then rolled into the site that became a worldwide phenomenon. And part of the reason for success was due to politics. "Twitter really took off during the presidential election because the campaigns took to it," Dorsey explained to New York Magazine. During the 2008 presidential election, Twitter was only two years old. And thanks to "instant feedback" from tweets, "Democracy is now operating at the pace of real-time," Stone told NBC.

Jack Dorsey co-founded Square, a mobile payment system, with his business partner "Jim McKelvey in 2009, then took it public in 2015," as revealed by Forbes. At this point in Dorsey's career, he had already founded Twitter and was the CEO of the company. But, he stepped down as the head of Twitter, and in the off-time, Dorsey started building a second company. 

Even with his name recognition, Dorsey admitted he had difficulties getting Square off the ground. "It was much harder the second time, actually, because everyone only saw what I did with Twitter," he told New York Magazine. Dorsey claimed people in the financial industry didn't think he had the experience in the field to excel. And like many tech hopefuls, Dorsey believed he could positively disrupt the system. "That's exactly why we're going to do so well — the financial industry is built around blockers and people saying no," Dorsey said in 2012. And thanks to a few high-profile accounts and users that year — like Mitt Romney and Obama's presidential campaigns — the app's popularity increased.

A few years after starting Square, Dorsey returned to Twitter. But he also kept his role as CEO of Square, "shuttling between two offices, running different companies, and remaining hands-on at both jobs." While this work ethic is admirable, not everyone was happy with the time split. "We're like the uglier but more successful stepchild," a Square employee told Vanity Fair about Twitter.

Prior to starting Twitter, Jack Dorsey explored many different career paths and passions. For a brief time, he was a model for vintage clothing. Dorsey tweeted a black-and-white fashion photo of his younger self wearing a Diesel jacket and screen printed t-shirt. And this wasn't the only instance of Dorsey staying close to the fashion industry. In a column for The New York Times, Dorsey reportedly would leave work early for hobbies like hot yoga and to take a "course at a local fashion school." Supposedly, the fashionista "wanted to learn to make an A-line skirt and, eventually, jeans." And in the darkest moments of frustration in the tech industry, Dorsey once again returned to the idea of working with clothing. According to Dorsey's former co-worker and friend Noah Glass, the future Twitter CEO once said, "I'm going to quit tech and become a fashion designer."

Though Dorsey never pursued the path of fashion, he at least tried to incorporate some of that spirit into tech. Dorsey admitted he was a big fan of punk rock and told New York Magazine he used to sport a "nose ring and dreadlocks." The entrepreneur revealed that he kept the piercing in the early days of Twitter when he tried to secure initial funds to grow the business. But when he saw someone else at lunch rocking the same look — a business suit plus a nose ring — he took out his jewelry "that night."

Once Silicon Valley took off as the creative hub of America, the rich and famous lifestyle no longer just applied to musicians and actors. Fortunes were made overnight, and some of the most influential people in business were tech founders. Following in the steps of famous tech stars like Steve Jobs and billionaire Bill Gates, Jack Dorsey's ascent from Twitter and Square turned him into a bonafide celebrity. Some people considered him "the greatest founder of a generation," according to Vanity Fair. And with this high praise, Dorsey fit right into Hollywood. "He spends a large amount of time in Los Angeles, hanging out with celebrities, like Kanye West and Kim Kardashian, basking in Rick Rubin's hot tub in Malibu, or attending dinner parties with Brian Grazer," the article revealed. In an Apple Music interview with Zane Lowe, Kanye West called Dorsey his favorite founder in tech. "Just incredibly smart. Visionary," West said about the CEO. West also credited Dorsey with treating him with respect and willing to invest in West's business ventures.

Not all celebrities give a positive endorsement of Dorsey. Seth Rogen talked privately with the Twitter CEO to discuss the platform allowing questionable users, like white supremacists. On the platform Dorsey created, Rogen tweeted, "after all the exchanges, I've reached a conclusion: the dude simply does not seem to give a f***."

In the '90s, Jack Dorsey enrolled at the Missouri University of Science and Technology. During his junior year, Dorsey became "bored" and decided to put his computer skills to the test. As described by The Verge, the college student hacked his way into a "bike messenger dispatching company" all the way in New York. Dorsey then pointed out "the security flaw to the company's chairman, Greg Kidd, who is impressed with Dorsey and asks him to drop out and move to New York to work with him." Dorsey accepted the offer and headed east to New York. While there, he enrolled in "NYU to appease his parents," according to the article.

Dorsey remembered his early years in the new city, far away from his hometown of St. Louis. "I should have gone to Columbia," he confessed to New York Magazine. "But I didn't want to be on the Upper West Side. I wanted to be downtown," Dorsey explained. Maybe things would have worked out differently if he attended a different college. But as for NYU, Dorsey decided to drop out of college for a second time. He and Kidd then moved out to Oakland with hopes of growing a business. His work wasn't as thrilling as he hoped. For a few months, Dorsey was a code writer "for an Alcatraz boat-tour outfit," The New York Times revealed. After that, he was "turned down for a job at Camper, the shoe store."

Facebook or Twitter — which do you prefer? Though both are an integral part of many people's daily lives, business-wise, the two are rivals. And as it turns out, the two were almost combined into one company. Billionaire Mark Zuckerberg, in control of Facebook, at one point, looked into buying Twitter, but the deal never went through. And around this same time, Dorsey was voted out of his own company. With the smart mind now available in the tech market, Zuckerberg tried to hire Dorsey to work for Facebook. "Zuckerberg wanted Dorsey to simply join Facebook in an unspecified capacity, and they would worry about a position later," according to The New York Times. But the super tech team was not meant to be. "I've got to think about this," Dorsey reportedly said, which really meant "no thanks."

Even though the deal never worked out, the two men remained amicable. "For a time, Zuckerberg and Dorsey met regularly for dinner. When they got together, Zuckerberg cooked," The New Yorker reported in 2013. "During the meal, they warily conversed about technological trends," the article continued. And Zuckerberg expressed why he enjoyed spending time with a fellow tech superstar. "The hardest thing as a founder is to keep your ... vision as a company grows. Jack has been clear and disciplined," Zuckerberg said. And Dorsey remembered the Facebook co-founder liked to dream big. "He'd ask me if I had any ideas," Dorsey explained.

Many tech hopefuls in Silicon Valley aspire to think of the next big idea and change the world. People like Mark Zuckerberg and Jack Dorsey started from humble beginnings to creating social media empires. But similar to Zuckerberg and the rise of Facebook, Dorsey made a few enemies on his way to the top. Earlier in his career, Dorsey worked for Odeo, a podcasting company co-founded by Noah Glass. Dorsey and Glass quickly became friends, and "After work, they would go on bike rides around the city or to live music shows and drink late into the night, usually talking about technology," according to a column in The New York Times. Glass and Dorsey also began discussing and expanding on the idea that would eventually become Twitter. And, according to the article, Glass was the one who came up with the name Twitter.

The friendship didn't last, and business ultimately split the two up. The two both moved to work at Twitter, but Glass was kicked out of the company. "What Glass didn't know was that Dorsey was the one who wanted him out," The New York Times claimed. As a result, Glass left Twitter before the site's massive popularity. And for the two men, in the end, it was estimated that "Dorsey will make $400 million to $500 million when Twitter goes public. Glass stands to make about as much as Dorsey's secretary at Square."

After a certain point, more money cannot add much to improve the quality of life — especially for billionaires, who would struggle to spend their fortunes completely. So, some of the wealthiest people in the world, like Bill and Melinda Gates and Jeff Bezos' ex-wife MacKenzie Bezos, pledged to give away part of their fortunes. Jack Dorsey similarly gave away part of his huge net worth. The CEO unselfishly decided to distribute a third of his stock in Twitter to all the other employees in the company. In a 2015 tweet, Dorsey said, "As for me: I'd rather have a smaller part of something big than a bigger part of something small. I'm confident we can make Twitter big!" The following year, the company's shareholders approved the deal, and his 6.8 million shares, worth about $98 million, went to employees, Forbes reported.

Years later, Dorsey stepped up again when the world was in crisis. As a result of the COVID-19 pandemic, he promised to donate to "relief programs related to coronavirus research," according to Vanity Fair. And this was no small offer. Dorsey pledged a massive "$1 billion, around 28% of his total wealth" to help in the global effort against the virus.

In late 2020, Jack Dorsey and Mark Zuckerberg — two of the wealthiest and most influential men in tech — testified in front of the Senate Judiciary Committee. Both men were responding to questions by politicians regarding the moderation processes of their social media companies — Facebook and Twitter. At the time, both companies allowed "elected officials and world leaders, respectively, to make claims on their platforms that would otherwise violate the companies' policies," CNN reported. But, as Dorsey clarified, "If an account is not a world leader anymore, that particular policy goes away."

Following the frightening storm of supporters on the Capitol Building in Washington D.C., Dorsey needed to address the policy once again. As a result, in Donald Trump's last month in office, Dorsey made the shocking decision to ban the president from Twitter — his favorite communication tool during his tenure. Dorsey posted a series of tweets to explain why he blocked the president, starting with, "I do not celebrate or feel pride in our having to ban @realDonaldTrump from Twitter, or how we got here. After a clear warning we'd take this action, we made a decision with the best information we had based on threats to physical safety both on and off Twitter."

Jack Dorsey may be one of the richest and most eligible bachelors in the world. As of 2021, the tech star has never been married and has no kids. Would you date this CEO? As far as his dating history, Dorsey was reportedly linked with "British model and actress Lily Cole ... and ballet dancer Sofiane Sylve," according to Page Six. Dorsey also had a complicated, "four-year on-again-off-again relationship with artist and popcorn maker Kate Greer." The two eventually split, but Greer stayed in the tech industry for her next romantic interest: Peter Fenton. Per Vanity Fair, Fenton, who was one of Twitter's "early investor[s] and board member[s]," decided to leave "his wife and started dating" Greer. By 2017, "Fenton left Twitter entirely" and was still with Greer — with a child along the way.

Dorsey moved on too, relationship-wise, and started dating Raven Lyn Corneil, a model. He even bought her a $4.5 million home in Los Angeles, the Daily Mail reported. The romance didn't last forever, and once the relationship ended, Dorsey put the house up for sale.

A common practice in Silicon Valley is a complete dedication to health and wellness. Contrary to the Cheetos and Mountain Dew stereotype that so many programmers have, the tech elite are highly regimented in their daily lives. Often, successful business heads "wake up before the crack of dawn," according to Inc. 

But no routines may be as intense as Jack Dorsey's. In a 2012 interview with New York Magazine, his mornings consisted of "waking up at 5:30 a.m. for meditation and a six-mile jog." However, as both technology and Dorsey's influence evolved, so did his daily activities. Reportedly, the CEO alters his program often, "so what he's doing now likely doesn't align with what he talked about months ago," via Vanity Fair. By 2020, Dorsey was using a "sleep-tracking ring" and taking ice baths first thing in the morning.

Taking a dip in ice is more than most people would ever consider in the morning, but Dorsey is just getting started. After meditating in a "warm tent sauna," the CEO works out then drinks an awful-sounding combination of water, salt, and lemon. He calls the drink "salt juice," and it's the only thing he consumes until dinner time. After his one meal of the day, Dorsey once again goes into his sauna, meditates, and jumps in the ice bath, "back and forth three times for an hour."

According to Forbes, in 2021, one needs to be worth "at least $2.1 billion" to rank as one of the 400 richest people in America. Jack Dorsey easily ranks in the top 90 as the owner of two major companies — thanks mostly to Twitter, one of the most used social media platforms in the world. In addition to his companies, Dorsey also plays the role of an angel investor, bringing in additional income. Altogether, as of January 2021, Dorsey was worth $12.2 billion, according to Forbes.

What does he do with all this money? According to Vanity Fair, "each day Dorsey wakes up in his multimillion-dollar glass mansion with postcard views of the Golden Gate Bridge." And though that would be more than enough for many people, Dorsey has plenty of money to spend. As reported by Variety, Dorsey expanded his real estate empire in 2019 by buying a $22 million home. Plus, it was right next door. Back in 2012, the CEO purchased a "flat-roofed midcentury modern" in the "Sea Cliff neighborhood of San Francisco" for $10 million. With his newest purchase, he could expand his estate in a city where space is a premium.