From fighting armies of bots to eating only seven meals a week, Twitter CEO Jack Dorsey leads a quirky and sometimes controversial life of privilege. Start with Dorsey’s turbulent career in Silicon Valley. After co-founding Twitter in 2006, he was booted out from the CEO position two years later, but returned to the company and later became permanent CEO again in 2015. Meanwhile, in 2010, he set up a second company, Square, that allows people to make debit and credit card payments with their mobile device. In recent years, he has led Twitter through the tech-lash that has engulfed social media companies, testifying before Congress multiple times. What ultra rich tech entrepreneurs do with their money Dorsey’s personal life and habits have also provoked controversy, with him extolling fasting as part of his daily routine. His existence is not entirely spartan, however. Like many other billionaires, he owns a stunning house and likes to date models. Scroll on to read more about the unusual life of Jack Dorsey. Like other tech billionaires, Dorsey never graduated from college As a teenager, Dorsey tried to start a bike courier company, writing dispatch software that is still used by some taxi companies. When he wasn’t checking out electronics stores or running a fantasy football league for his friends, Dorsey frequently attended punk concerts. Why does nobody talk about the fact that the CEO of twitter, Jack Dorsey, used to be an alternative kid who write poetry? That’s some KING energy. pic.twitter.com/QJwdggRh4N — spookymine (@YasmineSumman) April 7, 2020 Like many of his fellow tech billionaires, Dorsey never graduated from college . He briefly attended Missouri University of Science and Technology, then transferred to New York University, before calling it quits. In 2000, Dorsey built a simple program that let him update his friends on his life via BlackBerry and email messaging. Nobody really seemed interested, so he put the idea away. Who’s the richest entrepreneur to emerge from India’s tech boom? Twitter was born after the death of his first tech company Dorsey started in tech with a job at a podcasting company called Odeo, where he met his future Twitter co-founders. Odeo went out of business in 2006, so Dorsey returned to his earlier messaging idea and Twitter was born. On March 21, 2006, he posted the first tweet, from the simple handle, “@jack”. Dorsey and his co-founders, Evan Williams and Biz Stone, bought the Twitter domain name for about US$7,000 Dorsey took out his nose ring to look the part of a CEO but by 2008, Williams had taken over, with Dorsey made chairman of Twitter’s board. In 2011, Dorsey got the chance to interview then-US President Barack Obama in the first Twitter Town Hall. Dorsey had to remind Obama to keep his replies under 140 characters, Twitter’s limit at the time. Twitter went public in November 2013, and within hours Dorsey was a billionaire. It was revealed in a 2019 filing that Dorsey earned just US$1.40 as Twitter CEO the previous year, but as of November 2020, his shares in the company meant he was worth roughly US$8.5 billion. Why are all these billionaires wearing watches that even you can afford? He owns a BMW 3 Series, but reportedly doesn’t drive it often. He also reportedly paid US$9.9 million for this seaside house on El Camino Del Mar in the exclusive Seacliff neighbourhood of San Francisco. Inside this US$100 million California home, now half the price Before the pandemic, Dorsey said he worked from home one day a week Got you. Here’s my setup. I work from home Tuesdays. In my kitchen. Tweetdeck. No one here with me, and no one connected to my tweetdeck. Just me focused on your questions! #Karajack pic.twitter.com/6fHigDXmWC — jack (@jack) February 12, 2019 In an interview with journalist Kara Swisher conducted over Twitter, Dorsey said he worked every Tuesday out of his kitchen. He also told her that Tesla CEO Elon Musk is his favourite Twitter user. Dorsey said Musk’s tweets are, “focused on solving existential problems and sharing his thinking openly.” He added that he enjoys all the “ups and downs” that come with Musk’s sometimes unpredictable use of the site. Musk replied, tweeting his thanks and “Twitter rocks!” followed by a string of emojis. The many cars of Elon Musk: a ruined US$1m McLaren F1 to 007’s submarine car His eating habits have raised eyebrows Appearing on the Ben Greenfield Fitness podcast, Dorsey said he eats one meal a day and fasts all weekend. The comments drew fierce criticism from many who said Dorsey was normalising eating disorders. In a later interview with Wired , Dorsey stated that he eats seven meals a week, “just dinner”. Why Mark Zuckerberg chose to ‘kill what you eat’ and Jeff Bezos ate octopus Dorsey’s look as CEO has changed radically Dorsey used to regularly wear leather jackets and slim suits by Prada and Hermès, as well as Dior Homme reverse-collar dress shirts. More recently, Dorsey seems to care less about looking the part of a traditional CEO, favouring edgier outfits, including the classic black polo neck of Silicon Valley luminaries like Steve Jobs. He also reintroduced the nose-ring and grew a beard. Dorsey’s 2018 choice to go on a retreat in Myanmar was panned by critics Prime Minister Abe met Mr. Jack Dorsey, @jack CEO of Twitter @Twitter at his office. pic.twitter.com/1PxOQdXAvi — PM's Office of Japan (@JPN_PMO) December 6, 2018 Dorsey tweeted glowingly about a holiday 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 have been accused of having been complicit in fuelling hatred towards the Rohingya. However, Dorsey says he doesn‘t care about “looking bad” In a bizarre HuffPost 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 which drew sharp criticism. Billie Eilish’s body-shaming shows fashion still rarely celebrates real women Following the interview’s publication, Dorsey said he doesn’t care about “looking bad”. “I care about being open about how we’re thinking and about what we see,” he said. In September 2018, Jack Dorsey was grilled by lawmakers alongside Facebook COO Sheryl Sandberg. They were asked about election interference on their platforms as well as alleged anticonservative bias in social media companies. During the hearing, Dorsey shared a snapshot on Twitter of his heart rate spiking at 109 beats per minute. Dorsey has also appeared at a Senate hearing on Section 230, a 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. During the hearing, Dorsey once again faced accusations of anticonservative bias, with Republican lawmakers focusing on the way Twitter enforces its policies, particularly the way it labelled tweets from President Trump compared to other world leaders. Dorsey’s facial hair during the hearing attracted comment, being described as his “quarantine beard”, while others said it made him look like a wizard. Dorsey also addressed the way Twitter dealt with a dubiously sourced New York Post story from October 14, 2020, about Hunter Biden, son of Democratic presidential candidate Joe Biden. Twitter blocked users from sharing the URLs of the sources, citing its “hacked materials” policy. Dorsey subsequently apologised, saying it was wrong of Twitter to do so and said the Post’s Twitter account would remain locked until it deleted its original tweet, but that updated policies meant it could tweet the same story again without getting blocked. In 2018, Dorsey was reported to be dating Sports Illustrated model Raven Lyn Corneil View this post on Instagram A post shared by Raven lyn (@theravenlyn) on Sep 10, 2020 at 11:08am PDT 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 include actress Lily Cole and ballet dancer Sofiane Sylve. In early 2020, Dorsey’s job as CEO was under threat again Both Bloomberg and CNBC reported in late February 2020 that major Twitter investor Elliott Management – led by Paul Singer – was seeking to replace Dorsey as CEO. Elon Musk threw his support behind Dorsey. Just want say that I support @Jack as Twitter CEO. He has a good ️. — Elon Musk (@elonmusk) March 3, 2020 “Just want to say that I support @jack as Twitter CEO,” Musk tweeted, adding that Dorsey has a good heart using the heart emoji. The strange histories of our favourite internet companies Finally a deal was struck to leave Dorsey in place. On April 7, Dorsey announced that he was forming a new charity fund, Start Small LLC, that would help in coronavirus relief efforts. Dorsey said he would pour US$1 billion of his own Square equity into the fund. Want more stories like this? Sign up here . Follow STYLE on Facebook , Instagram , YouTube and Twitter . This article originally appeared on Business Insider.