Jack Dorsey’s Wealth and the Family Office Managing it

The Makings of a Prodigy

Jack Dorsey was born to Tim and Marcia Dorsey in St Louis on November 19, 1979. His father worked for a company that produced instrumentation equipment while his mother was a homemaker. He completed his primary and secondary education at Bishop DuBourg High School, graduating in 1995. Subsequently, he enrolled at the University of Missouri-Rolla to study Electrical and Computer Engineering before transferring to the prestigious New York University in 1997. However, he dropped out a semester short of graduating to focus completely on his entrepreneurial goals.

Dorsey developed a keen interest in computer science and programming from a very young age. By the age of 14, he began working on dispatch and logistics routing and developed a few open-source programs that are still used by various taxi companies. In hopes of scaling up his ideas, Dorsey moved to California and in 2000, started his own Oakland-based logistics company to dispatch cabs, couriers, and emergency city services.

The Dawn of the Microblogging Era

While working on dispatching software, Dorsey became fascinated with Instant Messaging (IM) like LiveJournal and AOL Instant Messenger and conceived the idea to develop a real-time, web-based, short messaging website that would use the broad reach of dispatch routing software to implement a seamless IM experience. He pitched this idea to his former Odeo employers and along with Biz Stone, Evan Williams, and Noah Glass started a company called ‘Obvious’ but later changed the name to ‘Twitter’.

The first Twitter prototype was designed as a website where users can instantly post short messages or “tweets” of 140 characters or less. The company was registered on March 21, 2006, with Dorsey as its first CEO. At the time of its inception, Twitter was not designed as a revenue-generating service and Dorsey focused more on improving its uptime instead. For the next two years, Twitter underwent several managerial changes and began gaining traction in 2008 when many prominent politicians, celebrities, and CEOs started joining the microblogging platform. However, Twitter first gained mainstream popularity when the platform was used by Presidential Candidates in the 2008 US Elections to provide regular updates to their supporters.

Twitter received a total of $760 million over its 7 per-IPO investment rounds with the company valued at $9.25 billion in 2011. It had its IPO on November 7, 2013, but its stocks struggled over the next months. At that time, Dorsey owned a 4.7% stake in the company.

By 2012, microblogging had essentially become an integral part of social media culture with Twitter counting over 500 million active users, with over 340 million daily tweets and over 1.6 billion daily search queries. Following its surge in popularity, Dorsey was reinstated as Twitter’s permanent CEO in 2015 and continued to serve in that capacity till November 2021. At the time of his exit, the company was valued at approximately $50 billion with him retaining $850 million worth of shares.

However, the legacy of Dorsey’s tenure as the founder and CEO of Twitter has been marred by allegations of dissemination of misinformation through the platform for years. A study by Nature outlines the effect that fake Twitter news had in the 2016 presidential elections. During the 2020 US Presidential Elections, Twitter also took the controversial decision to ban the then US President Donald Trump from using the platform citing the promotion of violence and the spread of misinformation.

Twitter was acquired by Elon Musk in October 2022 for $44 billion. Jack Dorsey publicly expressed support for Musk’s takeover, stating that he believed Musk was the right person to lead the platform into the future. However, he later criticised some of Musk’s decisions regarding Twitter’s direction and leadership.

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“Squaring” Up His Millions

After stepping down as Twitter’s CEO in 2008, Dorsey conceived the idea of developing a digital payment interface for smartphones and began working on his new venture “Square, Inc” along with his friend Jim McKelvey out of a small office in St. Louis. Square allowed users to receive credit card payments through a square-shaped card reader that could be plugged into the headphone jack of smartphones.

Square secured $10 million in Series A funding and tested its first product in May 2010. Within a year, the company saw rapid adoption, processing millions of dollars in transactions weekly. By September 2012, Square’s valuation had surged to over $3.2 billion, cementing its position as a major player in the digital payments space.

Square underwent seven rounds of funding before its IPO in November 2015. The company expanded its services in 2017 by introducing Bitcoin trading for select users, a move that contributed to a significant increase in its stock value. In 2018, Square acquired Weebly, a web hosting and website-building company, to strengthen its e-commerce capabilities. The following year, it divested Caviar—a food delivery service acquired in 2014—selling it to DoorDash for over $410 million.

The majority of Dorsey’s wealth is tied to his shareholding in Block, Inc., though the precise percentage fluctuates due to share structure and dilution. He remains the company’s largest individual shareholder and key strategic figure. He is also an angel investor and has made a total of 26 personal investments (and 6 exits) in early-stage startups. Dorsey has also invested in fintech platforms such as Movii, leading its $17 million Series C round, part of his broader interest in financial inclusion and decentralised payments. However, the majority of his portfolio is managed by ICONiQ Capital.

ICONiQ Capital is a multi-family office and investment fund with an estimated $70–85 billion in assets under management as of 2025. The firm was founded in 2011 as a Limited Liability Company (LLC) by ex-Goldman Sachs analysts, Divesh Makan, Michael Sanders, and Chad Boeding in San Francisco, California. ICONiQ ‘s clientele consists of 257 HNWI – Mark Zuckerberg, Satya Nadella, Blake Lively, Ashton Kutcher, among others – and 45 charitable organisations.

In December 2021, Square rebranded as Block, Inc., reflecting its broader focus beyond payments, particularly in cryptocurrency and blockchain-related services. Jack Dorsey has long been an advocate of Bitcoin, frequently emphasising its potential to revolutionise finance. While he previously suggested that cryptocurrency could play a role in Twitter’s future, his departure from the company in 2021 shifted his full attention to advancing Bitcoin-centric initiatives within Block.

In 2022, Dorsey’s division TBD unveiled the concept of Web5, aiming to build a decentralised web layer on Bitcoin. However, by late 2024, Block shelved its Web5 initiative in late 2024, redirecting resources toward Proto (its Bitcoin mining hardware venture) and Bitkey, a self-custody Bitcoin wallet. Dorsey continues to focus on expanding Block’s Bitcoin infrastructure and mining ecosystem.