Jack Dorsey-Overstretched? – Business Leader Biography

6 min

Born on November 19, 1976, Jack Patrick Dorsey is the co-founder and CEO of Twitter. Born and brought up in St. Louis, Dorsey is of Irish, English, and Italian descent. Very few people know that in addition to heading Twitter, Dorsey is also the founder and CEO of Square, a mobile payments company.

Early life

Born to an engineer father and homemaker mother, Jack got fascinated with computers and communications at a very young age and started programming during his formative years. During those days, car rental companies and players in the transportation industry were having a tough time managing their drivers and vehicles. Fascinated by the challenge, Dorsey wrote a dispatch software at the age of 15. The open source software that he created is still used by some operators to coordinate their fleet and taxi drivers.

From 1995-97, Dorsey went to the University of Missouri-Rolla. Later he took a transfer to New York University but didn’t complete his graduation, dropping out in 1999. It was during his time at NYU that the idea of Twitter first came to his mind.

After leaving college, Dorsey started working as a programmer and moved to California. In 2000, he started his first company in Oakland. His focus was mainly on dispatching couriers, taxis, and emergency services from the web. During his early days as an entrepreneur, Jack also came up with the idea of creating a frictionless service market.

In 2000, Jack came up with the idea of a web-based real-time status or short message communication service. When he first came across the implementation of instant messaging, Dorsey was curious to know whether the software’s user status output could be shared successfully among a group.

To get answers to his questions, Dorsey approached Odeo which at that time was working on ‘text messaging.’ Within a couple of weeks, Dorsey and Christopher Isaac Biz Stone created a prototype of Twitter. The idea got many takers. The initial investment was provided by Evan Williams, a computer programmer and Internet entrepreneur who is credited with founding several Internet companies.


Biz Stone, Dorsey, and Noah Glass, an Odeo executive, co-founded Obvious Corporation, that was later renamed Twitter. Dorsey was appointed as the CEO of the startup. He saw the company through the initial two rounds of funding by venture capitalists. On March 21, 2006, Dorsey announced the arrival of Twitter by posting the first tweet on Twitter that read “just setting up my twttr.”

A couple of years later, Dorsey was replaced by Williams as the company’s CEO. Dorsey was now the chairman of Twitter. It is widely believed that Dorsey’s habit of leaving office early to pursue other interests including fashion designing and yoga cost him his position.

The first few years were very difficult for Twitter. Many people ridiculed the concept, deriding it as a tool for self-centered people who are eager to share the intricacies of their lives with strangers for social approval. Frequent service outages didn’t help either, and Twitter soon became the butt of jokes.

As prominent personalities including celebrities and presidential candidates started taking to the platform to Tweet, things started taking a turn for the better. In 2008, the then Presidential candidates Barack Obama and John McCain used Twitter extensively to update their supporters on major developments. In June 2009, Twitter vaulted to international prominence when thousands of Iranians took to the streets to protest the claimed victory of the then president Mahmoud Ahmadinejad. When the government blocked text messaging and satellite feeds, Iranians started flooding Twitter with live updates. Twitter claims that a US government spokesperson called Dorsey requesting him to postpone the scheduled maintenance so that Iranians can continue tweeting.

When Twitter started becoming popular, Dorsey focused on improving uptime rather than creating more revenue. Dorsey firmly believed that API and commercial use of Twitter are two separate things. Dorsey says his three guiding principles are simplicity, craftsmanship, and constraint.

In 2011, Dorsey was appointed as the executive chairman of Twitter, while Dick Costolo replaced Williams as the company’s CEO. In 2015, Costolo resigned from his position. Costolo’s departure from Twitter led to Dorsey’s appointment as its interim CEO. A few months after Costolo’s resignation, Dorsey was appointed as Twitter’s permanent CEO.

After being elevated to the company’s top spot, Dorsey announced the top management’s decision to reduce the workforce at Twitter by 8 percent. Twitter claimed that the move was a part of its strategy to organize around the company’s top products and drive efficiencies.

Dorsey: A billionaire businessman 

In 2013, when Twitter went public, Dorsey’s personal wealth skyrocketed. Initially traded at $26, Twitter shares soon hit the $45 mark. Within hours, the value of Dorsey’s 23.4 million shares went up the roof, and he became a billionaire the same day. As of January 2019, Dorsey’s net worth is estimated to be $5.5 billion.

In 2016, some users claimed that Twitter was planning to bring a new algorithm, which created a huge controversy. A day after the news surfaced on the Internet, Dorsey cleared the air saying that it was a hoax.

In January 2016, the number of tweets dropped to 300 million from close to 500 million in 2013. As a part of the company’s efforts to entice new users, Dorsey, in May 2016, announced that Twitter wouldn’t count photos and links in the 140-character limit.

In 2016, Dorsey’s Twitter account was suspended for a brief period. After his account was restored, Dorsey tweeted that the suspension was a result of an internal mistake.

In 2017, Dorsey and Executive chairman Omid Kordestani donated $530,000 to American Civil Liabilities Union. The amount of donation matched the amount raised by staffers, bringing the total amount to $1.59 million.

In 2018, Dorsey announced that the team at Twitter is working on and will soon come up with an improved version of the verification system. Twitter claims the purpose behind the move is to let people verify more personal facts about themselves. In September, Dorsey, along with Facebook’s COO Sheryl Sandberg, testified before the Senate Intelligence Committee about Twitter’s role in meddling with the 2016 presidential elections. Following the testimony, Twitter shares fell by 6 percent.


Dorsey, along with Jim McKelvey, a renowned American businessperson, entrepreneur, and philanthropist developed a platform for small businesses to accept card payments. The platform was named Square and was released in 2010. To send payments, users need to attach a tiny device that serves as a mini card reader to their smartphone or computer. Square can also be used for paperless receipts through text or email. The Square app is available on Google Play and Apple Play Store.

In December 2009, Square had ten employees. In 2011, the number of people working at the organization crossed 100. The company went public in 2015. Square’s office is located on Market Street in San Francisco. Dorsey holds around 25 percent shares in Square and is its CEO. In 2017, Square’s estimated revenue was around $3.2 billion.

Other projects 

On December 24, 2013, Walt Disney announced the appointment of Dorsey as a member of its board of directors. In the press release by Disney, Dorsey was hailed as a talented entrepreneur. The company said that Dorsey was fit for the role as his experience aligned with Disney’s strategic priorities. In 2018, Dorsey said that he wouldn’t seek reelection due to a clash of interests with the board.

In addition to holding the position of CEO at Twitter, Dorsey is a board member of the Governance Center managed by the Berggruen Institute.


Ex-Twitter CEO, Costolo described Dorsey as a very calm and thoughtful leader. Charles Whiteland, a professor at Cornell Law School says Dorsey has the unique capability of appealing to investors who share his vision and employees whom he wants to retain.

Personal life 

In 2012, Dorsey moved to the Sea Cliff neighborhood in California. The area is known for its lavish, big properties that offer breathtaking views of the Golden Gate Bridge, the Pacific Ocean, and the Marin Headlands. Some famous current and ex-residents of the neighborhood include Robin Williams, Ansel Adams, Eugene Levy, Sharon Stone, and Kirk Hammett. In the past, Dorsey has been linked with many women including yoga instructor Kate Greer and British model Lily Cole.

Dorsey is a Kendrick Lamar fan. In his free time, he likes tuning in to FIP, a French radio station. Dorsey walks to work every morning. He claims the 5-mile walk helps clear his head. Dorsey is an avid yoga enthusiast. In 2017, he completed a Vipassana course taught by the disciples of S.N. Goenka, a late Burmese-Indian teacher of the technique.

Awards and recognition

In 2008, Dorsey was included in the list of top 35 innovators in the world under 35 compiled by MIT Technology Review, a magazine owned by MIT.

At the 5th chapter of the Annual Crunchies Awards that were held in 2012, Dorsey was named the founder of the year.

In 2018, CEO World Magazine ranked Dorsey 404th in its list of Best CEOs in the World.

In 2012, he won the Innovator of the Year award for technology by Forbes.

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