Jack Dorsey: Uni Drop-out To Twitter CEO

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Written By Mohsen Salami

Web developer and entrepreneur Jack Dorsey has a habit of dropping out of key roles – but is still one of the wealthiest men in the world, with a personal fortune estimated at £4.3 billion.

He left New York University without finishing a degree course and dabbled as a masseur and with fashion design before setting up the online messaging app Twitter, from where he resigned as CEO in 2008.

Dorsey reprised the role in 2015 until 2021, leaving the Twitter board in May 2022.

For the moment, he is holding steady as CEO at online payment processor Block (formerly Square), which he founded with former banker Jim McKelvey in 2009.

Early Years

Dorsey was born in November 1976 in the Missouri city of St Louis. His father, Tim worked in a factory manufacturing scientific devices, while his mother, Marcia was a stay-at-home mum.

He showed an early interest in technology. While only 14 years old, Dorsey developed open-source software for despatching cabs that is still in use today.

After high school, Dorsey attended the University of Missouri-Rolla, leaving after two years to transfer to New York University. He dropped out of the course a term before graduating.

While studying in New York, Dorsey came up with the outline of an idea for an internet messaging app that eventually evolved into Twitter.

The evolution was complicated.

First, Dorsey moved to San Francisco, where he worked on his taxi dispatching app. Then he realised a short messaging app would improve his software, and the germ of an idea for Twitter was born.

After building a prototype short messaging service, private investors realised the potential, and Evan Williams stepped up with Biz Stone and Noah Glass to co-found Twitter with him.


Making money from Twitter was never the guiding principle for the búsiness.

Dorsey’s mantra as CEO was simplicity, constraint and craftsmanship. Under his tenure, the company introduced the infamous 140-character limit on Tweets, the name coined for messages sent across the network.

Dorsey sent the first Tweet on March 21, 2006.

Twitter quickly became a leading social messaging hub.

Dorsey remained CEO until October 2008. He reportedly stepped down for regular work absences to enjoy yoga sessions and Dorsey’s passion for fashion design.

Chip Off The Block

During his time as CEO, Dorsey oversaw Twitter going public in 2013, raising £1.44 billion.

In 2009, Dorsey co-founded Square, which later became Block. Square is a small, mobile smart device that processes credit card transactions remotely.

Between 2009 and 2015, Dorsey spent his wilderness years away from controlling Twitter in many other roles. During this time, he was a member of two US State Department delegations that visited Iran and Russia. He also joined the board of media giant Disney.

In July 2015, Dorsey returned to the CEO’s chair at Twitter as interim CEO. Four months later, he took the post while retaining the role at Square.

In his second stint as CEO at Twitter, Dorsey was criticised for restricting access to the service by US right-wing conservatives.

Dorsey banned then US President Donald Trump from Twitter for Tweets deemed to violate the service’s objectionable content policy. Trump and the government threatened to legislate to ensure conservative voices kept their right to freedom of speech.

Dorsey resigned as Twitter CEO again and left the Twitter board in 2021. He explained that being ‘founder-led’ was ‘severely limiting and a single point of failure.’ However, many commentators believed hedge fund Elliott Management pushed him over the brink when buying £1 billion of Twitter stock.

The billionaire businessman also rues some of the decisions taken about Twitter.

“I don’t believe anyone should own or run Twitter. It wants to be a public good at a protocol level, not a company,” he Tweeted.

Dorsey and Musk have a similar vision for Twitter as a private company offering an inclusive and diverse social media platform. Both believe the current incarnation of Twitter run by suits from Wall Street and pursuing an advertising model to raise funds is the wrong path.


Block launched as Square in 2010 and within two years had enrolled 2 million users in the US.

Overseas expansion started in 2013 with Japan. Block is available in eight countries, including the US, Japan, France and the UK.

The name changed from Square to Block in December 2021 as Dorsey thought the name better represented the company and his interest in blockchain applications.

Dorsey owns 24 per cent of the company and came up with the idea for Block when co-founder McKelvey failed to sell $2,000 of bathroom fittings because he could not take a credit card payment.

Block also includes several other web services, like Cash App, a person-to-person money transfer app, web hosting service Weebly, and media streaming service Tidal, co-owned with rapper Jay-Z.

In November 2019, Block floated in New York with a £2.3 billion valuation.


Dorsey has been a vocal Bitcoin cheerleader and has said if he were not involved in Twitter or Block, he would champion and develop Bitcoin.

Despite his advocacy, Dorsey thinks cryptocurrency needs to address issues like price volatility, fraud and environmental concerns regarding mining before becoming mainstream.

Block is invested in Bitcoin, owning 8,027 coins worth £193 million.

Jack Dorsey FAQ

Is Jack Dorsey married?

Dorsey is single and has no children.

Where does Jack Dorsey live?

He lives in a luxurious £25 million cliff-top home in San Francisco’s Sea Cliff neighbourhood The property commands views of the Golden Gate Bridge. Sea Cliff is celebrated as one of the Californian city’s most prestigious and expensive addresses.

Where did the idea for Twitter come from?

Dorsey was developing software for dispatching taxis when he thought about adding a module for sending short, free text messages. The module became Twitter.

What does Dorsey do to relax?

Yoga and meditation are top of Jack Dorsey’s relaxation activities. He famously parted ways as Twitter CEO for the first time for spending hours each working day meditating.

What did the first Tweet say?

Jack Dorsey sent the first Tweet on March 21, 2006. The message said: “Just setting up my twttr.”
An NFT of the Tweet sold for £2.3 million in 2021. However, the new owner’s attempt to resell the NFT attracted a bid of £222 against an asking price of £38.5 million.

Is Jack Dorsey friends with Elon Musk?

Dorsey and fellow billionaire Elon Musk, CEO of car maker Tesla, are long-standing friends. Both the entrepreneurs share a passion for cryptocurrency. Musk is also negotiating the purchase of Twitter for an estimated £35 billion. Dorsey has endorsed Musk as the right man for heading the social media platform.

Will Jack Dorsey return as Twitter CEO?

Many have asked the question and Dorsey has spoken to quash the rumours.
In Tweets he has said “nah, I’ll never be CEO again” and commented that Twitter doesn’t need a CEO and that the platform would be better as a decentralised service rather than a traditional social media network.
THat move could suit Elon Musk if he finally takes control at Twitter, as the platform would only exist on a peer-to-peer network like a blockchain and would sit beyond any government regulation.