How Jack Dorsey Made $10 Billion From Microblogging

Many entrepreneurs have great ideas, and many have great strategies. Some, though, have an idea or strategy that is so groundbreaking that it takes on a life of its own. Jack Dorsey, the founder of Twitter and Square, has had a highly controversial career with several highs and lows. His brilliant insights into needed tech and his programming knowledge stand in an odd juxtaposition to his occasionally lackluster leadership. However, despite several setbacks and outright failures, he has grown steadily in wealth and influence.

Dorsey is no stranger to business— it’s in his blood. His father was also entrepreneurial from a young age, cofounding a pizza restaurant where he ended up meeting his wife, Dorsey’s mother. She, too, had a love for enterprise and started a successful coffee shop. After leaving the pizza shop to his friend, his father established a small business selling medical devices.

Jack Dorsey dropped out of school to build his first company

Dorsey’s parents pushed him to explore his interests and find his passion. After a few false starts, he discovered a love of programming. At age 15, he was fascinated by the complexities of coordinating numerous vehicles through dispatch systems. After studying the technology in use, he created a more efficient system and attempted to start a bicycle courier business to use it. The venture never took off. The software itself, though, was so groundbreaking that many taxicab companies still use it today.

Dorsey was accepted to the Missouri University of Science and Tech after high school but quickly grew impatient and bored with the coursework. While playing around with his dispatch hobby, he discovered a security flaw in a New York bike messenger company. When he pointed it out to the chairman, Greg Kidd, he was invited to work for the company. He accepted the offer and transferred to New York University.

In 2000, Dorsey decided to drop out of college again and moved across the country to California to start up an internet business selling his dispatch software with Kidd. After only two years, however, he was fired from his own company by board members tired of wrangling with him. Feeling defeated, he sought gigs on Craigslist and experimented with ideas for a new business.

The partnership that changed Jack Dorsey’s life forever

A few years of failed jobs and ventures left Dorsey frustrated and desperate, but his luck turned around in 2005 when he met Evan Williams at a café. Williams, another tech entrepreneur, needed programmers for his podcasting startup, Odeo. He offered him a job as a low-level coder and Dorsey accepted, eager to re-enter the software industry.

Soon after he entered the company, though, Odeo was put in jeopardy by Apple adding a podcast feature to iTunes. Williams held a company hackathon to choose where the company would go next. Dorsey proposed a system that combined the live updates of a dispatch system with the social aspect of SMS. Odeo’s cofounder Noah Glass loved the idea and pushed for its adoption.

Dorsey’s idea won. He coded the prototype in two weeks and named it Obvious. The name was changed to Twttr, and the site was quietly launched in 2006.

Twitter was not an overnight success

For a while after Twttr launched, most of the attention it received on a national scale was derisive. For the first nine months after it opened to the public, its users totaled in only the tens of thousands. After a short period of time, Twttr was ultimately renamed Twitter.

In March 2007, the company made its first major public debut at South by Southwest (SXSW), a major conference for tech startups. Dorsey and Williams decided against a trade booth at the convention. Instead, they opted for the unconventional choice to pay the venue to set up live screens on the trade show floor. The screens displayed a rolling view of tweets as they went up, and the convention-goers went wild for it. New user registration skyrocketed, and within months the number of users had jumped to hundreds of thousands.

In April 2007, Twitter separated from Odeo and became a freestanding company. As the company continued the rapid growth rate, Dorsey launched and completed two rounds of funding. The first round only brought in $100,000 based on a company valuation of $220,000. By October 2007, though, that valuation had jumped to an astounding $35 million.

Jack Dorsey was fired as CEO

Despite the rapid growth of the company, though, the board members were not pleased with Dorsey’s leadership. He became increasingly uninvolved with the company physically and mentally and often argued with Williams. In 2008, he was replaced as CEO by Williams and took a back seat as a board member himself.

Disheartened but undeterred, Dorsey immediately turned his attention to other projects. A few ideas came and went, but when he invested in Foursquare, he had another business epiphany. Seeing the struggle of small businesses to compete for sales with customers carrying cash less and less, he came up with Square in 2009.

The small gadget connected to the vendor’s device and allowed them to accept card payments, and financial pundits went nuts for it. After a 10-month limited pilot program, Dorsey launched the system for the public in late 2010. As predicted, the company grew at a startlingly fast rate. By 2012, it was bringing in over $200 million annually, a number that has continued to grow substantially each year since.

Square put Jack Dorsey back on the map

After unrest within Twitter’s upper management ousted Evans from the CEO position, Dorsey was invited to return as executive chairman. He did so while maintaining his CEO position at Square, a feat that few tech entrepreneurs have managed. He had learned focus and restraint at his other company, although he still struggled with taking action when needed.

Dorsey’s method of slow, careful progress has arguably paid off for both companies, however. When he took Twitter to a public offering in 2013, it jumped to an initial valuation of $31 billion. With a 5% stake in the company, he became a billionaire overnight. By 2014, his net worth had grown to $2.2 billion.

At this point, both Square and Twitter were growing at a viral rate. Square went public in 2015 with an IPO valuation of $2.9 billion. Shortly afterward, Dorsey was selected to lead Twitter as CEO again after the poor leadership of Costolo galvanized the board to action.

By 2019, Square was a force to be reckoned with, generating an annual revenue of $4.714 billion by collecting small percentages of transactions. Twitter’s advertising revenue that same year was $3.46 billion. These companies are both massive powerhouses within their industry, and their common denominator is their founder.

Jack Dorsey’s net worth

Jack Dorsey has a net worth of around $10 billion. He is something of an enigma to many business analysts to this day. Unlike most Silicon Valley tech founders, he enjoys hobbies, vacations, and balance rather than a 24/7 work mentality. The consensus seems to be that his ideas simply are too good to die, but many believe that his unconventional leadership and personality are exactly what makes him succeed.


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