The career rise and wild life of tech billionaire Jack Dorsey

Dorsey began programming while attending Bishop DuBourg High School in St. Louis.

At age 15, Dorsey wrote dispatch software that is still used by some taxi companies, according to a biography on Dorsey. For fun, he attended punk rock shows.

He briefly attended the Missouri University of Science and Technology and transferred to New York University before calling it quits in 1999, one semester before graduation, to focus on his idea for Twitter, according to the biography.

In 2000, Dorsey built a simple prototype that let him update his friends about his life via BlackBerry and email messages.

The experiment with basic code on a Blackberry predecessor – detailed in a 2013 New Yorker article – didn't impress his friends. Around 2002, he became a professional masseuse, The Wall Street Journal reported.

He got a job at a podcasting company named Odeo, where he met his future Twitter cofounders.

Dorsey said he had no interest in podcasting but wanted to learn about the "consumer side of the internet" in a 2011 interview with Stanford's eCorner.

He met Twitter cofounders Evan Williams, Biz Stone, and Noah Glass while working at Odeo, where Twitter began to take shape. He, Stone, and another programmer were given two weeks to write the software that would support Twitter.

On March 21, 2006, Dorsey posted the first tweet.

Dorsey kept his Twitter handle simple, "@jack." He hasn't changed it since. In 2007, Dorsey became Twitter's first CEO.

A year later, Dorsey was already less hands-on at Twitter. By 2008, Williams had taken over as CEO, and Dorsey had transitioned to Twitter's board chairman.

Dorsey immediately got started on new projects. He invested in Foursquare and launched a payments startup called Square that let small-business owners accept credit-card payments through a smartphone attachment.

Dorsey became a billionaire after Twitter went public in November 2013.

In 2014, Forbes pegged Dorsey's net worth at $2.2 billion, and it spiked to $12.5 billion in 2021. However, Dorsey didn't take home a large paycheck from Twitter.

A 2019 filing said Dorsey earned just $1.40 for his job as Twitter CEO the previous year. The $1.40 salary actually represented a pay raise for Dorsey, who in previous years had refused any payment at all.

He purchased a multi-million dollar seaside house on El Camino Del Mar in the exclusive Seacliff neighborhood of San Francisco.

The house, which has a view of the Golden Gate Bridge, cost him $9.9 million, according to Curbed SF.

Dorsey told Kara Swisher in 2018 that Elon Musk was his favorite Twitter user.

Dorsey said Musk's tweets were "focused on solving existential problems and sharing his thinking openly."

He added that he enjoyed all the "ups and downs" that came with Musk's sometimes unpredictable use of the site. Musk himself replied, tweeting his thanks and "Twitter rocks!" followed by a string of emojis.

Both Musk and Dorsey are crypto enthusiasts and have been friendly in the past — even texting each other.

Dorsey's eating habits have raised eyebrows over the years.

In 2019, Dorsey appeared on a podcast run by a health guru. Dorsey said during his interview that he ate one meal a day and fasted all weekend. He said the first time he tried fasting, it made him feel like he was hallucinating.

"It was a weird state to be in. But as I did it the next two times, it just became so apparent to me how much of our days are centered around meals and how the experience I had was when I was fasting for much longer, how time really slowed down," he said.

In a later interview with Wired, Dorsey said he ate seven meals a week, "just dinner."

He has said Mark Zuckerberg once served him a goat he had killed himself. Dorsey told Rolling Stone about the meal, which took place in 2011. Dorsey said the goat was served cold and that he stuck to a salad.

In September 2018, Dorsey was grilled by lawmakers.

Dorsey and Sandberg were asked about election interference on Twitter and Facebook, as well as alleged anti-conservative bias in social media companies.

During the hearing, Dorsey shared on Twitter a snapshot of his spiking heart rate. He was in the hot seat for several hours, and he showed his heart rate peaked at 109 beats per minute.

Dorsey has faced his share of controversy. In 2018, a tweet about his vacation in Myanmar provoked an outcry.

Dorsey tweeted glowingly about a vacation he took to Myanmar for his birthday in December 2018. "If you're willing to travel a bit, go to Myanmar," he said.

This came at the height of the Rohingya crisis, and Dorsey was attacked for his blithe promotion of the country, especially since social media platforms were accused of having been complicit in fueling hatred toward the Rohingya, a Muslim minority ethnic group.

Dorsey has said he doesn't care about "looking bad."

In a bizarre Huffington Post interview in 2019, Dorsey was asked whether Donald Trump — an avid tweeter — could be removed from the platform if he called on his followers to murder a journalist. Dorsey gave a vague answer that drew sharp criticism.

Following the interview's publication, Dorsey said he didn't care about "looking bad."

"I care about being open about how we're thinking and about what we see," he said.

Dorsey testified before Congress once again in 2020.

Dorsey appeared via videoconference at the Senate hearing on Section 230, a part of US law that protects internet companies from legal liability for user-generated content, as well as giving them broad authority to decide how to moderate their own platforms.

In prepared testimony ahead of the hearing, Dorsey said stripping back Section 230 would "collapse how we communicate on the Internet" and suggested ways for tech companies to make their moderation processes more transparent.

During the hearing, Dorsey again faced accusations of anti-conservative bias.

The accusations from Republican lawmakers focused on the way Twitter enforces its policies, particularly the way it has labeled tweets from Trump compared to other world leaders.

Dorsey took the brunt of questions from lawmakers, even though he appeared alongside Facebook CEO Mark Zuckerberg and Google CEO Sundar Pichai.

He appeared at another hearing a few weeks later alongside Zuckerberg, facing questions from Republicans who were displeased with how the platforms had handled Trump's social media accounts.

Dorsey's dating life has sparked intrigue. In 2018, he was reported to be dating the Sports Illustrated model Raven Lyn Corneil.

Page Six reported in September 2018 that the pair were spotted together at the Harper's Bazaar Icons party during New York Fashion Week. Page Six also reported that Dorsey's exes included the model and actor Lily Cole and the ballet dancer Sofiane Sylve.

Twitter said Dorsey had stepped down as CEO in 2021.

Dorsey posted on his Twitter account in 2021 saying: "Not sure anyone has heard but, I resigned from Twitter."

In his tweet, he included a screenshot of the email he sent to Twitter staff announcing his resignation.

In May 2022, his time on the board of directors also officially ended, an anticipated move that coincided with the company's stockholders' meeting.

Two days after Dorsey stepped down as Twitter CEO, Square changed its name to Block.

"The name change creates room for further growth," the company said in a statement.

"Block references the neighborhood blocks where we find our sellers, a blockchain, block parties full of music, obstacles to overcome, a section of code, building blocks, and of course, tungsten cubes," it added.

The line about tungsten cubes was an apparent reference to a craze among crypto enthusiasts of paying as much as $3,500 for novelty tungsten cubes.

In April 2022, Dorsey changed his official title at Block from CEO to "Block Head." The title change was made official in a regulatory filing with the Securities and Exchange Commission on April 20, 2022.

"There will be no changes in Mr. Dorsey's roles and responsibilities," the filing said.

Block's website was also updated to list his new title as Block Head.

Dorsey is a big believer in cryptocurrency.

In particular, Dorsey is a fan of bitcoin, a cryptocurrency he described in early 2019 as "resilient" and "principled." He told the "Tales of the Crypt" podcast in March that year that he was maxing out the $10,000 weekly spending limit on Square's Cash App to buy up bitcoin.

In October 2020, he slammed Coinbase CEO Brian Armstrong for forbidding employee activism at the company, saying cryptocurrency is itself a form of activism.

He's also said he hopes bitcoin can help bring about "world peace" in a panel alongside Musk and Ark Invest CEO Cathie Wood called "The B Word" on July 2021. He said he loves the bitcoin community because it's "weird as hell."

"It's the only reason that I have a career — because I learned so much from people who are building bitcoin today," Dorsey said.

Dorsey was questioned over Twitter's sale to Musk.

In August 2022, Twitter's former head of security, Peiter Zatko, filed a whistleblower complaint with the SEC, alleging the company participated in negligent security practices under Dorsey.

In his 84-page report and subsequent testimony, Zatko made a number of allegations against the company, including claims it had "egregious deficiencies" around security protocol and that Dorsey experienced a "drastic loss of focus" in his last year as CEO of Twitter.

A month later, Dorsey was deposed and questioned under oath for another issue: Musk's legal battle with Twitter over his proposed $44 billion takeover.

Musk's team accused Twitter of misleading investors and intentionally "miscounting" spam accounts.

Dorsey had tried to add Musk to Twitter's board.

In the texts, Dorsey explained why he left the company and said he previously pushed to get Musk involved with Twitter.

"A new platform is needed. It can't be a company. That's why I left," Dorsey wrote to Musk, adding he thought Twitter should be an "open-sourced protocol" and couldn't "have an advertising model."

Dorsey also told Musk he had advocated for the Tesla CEO's addition to the Twitter board a year earlier. But his request was denied, which he said he thought "was completely stupid and backwards."

Dorsey launched a Twitter rival called Bluesky Social in 2022.

The blockchain-based company's beta launch raked in 30,000 signups in two days. According to Bluesky's website, the company is intended to support "a new foundation for social networking which gives creators independence from platforms, developers the freedom to build, and users a choice in their experience."

As of 2026, the company said it had over 40 million users.

Dorsey apologized for what happened at Twitter after Musk took over.

After Musk ordered mass layoffs at Twitter after taking over in November 2022, Dorsey tweeted an apology: "I own the responsibility for why everyone is in this situation: I grew the company size too quickly. I apologize for that."

"Folks at Twitter past and present are strong and resilient," he wrote on Twitter. "They will always find a way no matter how difficult the moment. I realize many are angry with me."

He continued: "I am grateful for, and love, everyone who has ever worked on Twitter. I don't expect that to be mutual in this moment...or ever…and I understand."

Dorsey says running Twitter is "hard" after backlash to Musk changes

In 2022, Dorsey criticized Musk's decision to rebrand the social media site's Birdwatch feature to Community Notes, dubbing it the "most boring Facebook name ever."

In April 2023, the Twitter cofounder also openly criticized Musk's leadership in a series of social media posts, writing that "it all went south" and Musk "should have walked away" from the acquisition.

In July 2023, however, Dorsey said "running Twitter is hard" after Musk sparked a backlash by announcing "rate limits" on viewing tweets.

"I don't wish that stress upon anyone," Dorsey tweeted. "I trust that the team is doing their best under the constraints they have, which are immense. It's easy to critique the decisions from afar … which I'm guilty of … but I know the goal is to see Twitter thrive. It will."

Dorsey also urged "calm" when Musk rebranded Twitter to X last year.

Dorsey announced that Block is laying off 40% of its staff.

Block laid off 4,000 employees on February 26. Dorsey addressed staffers in a memo, writing, "i had two options: cut gradually over months or years as this shift plays out, or be honest about where we are and act on it now. i chose the latter."

Dorsey wrote that although Block was not in financial trouble, "something has changed."

"we're already seeing that the intelligence tools we're creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company. and that's accelerating rapidly," Dorsey, who shared the memo on X, wrote.

In a separate X post, Dorsey wrote that his company overhired during the Covid-19 pandemic, but that wasn't the only factor at play.

"I incorrectly built 2 separate company structures (Square & Cash App) rather than 1, which we corrected mid-2024, but this misses all the complexity we took on through lending, banking, and BNPL," he wrote.