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How Jack Dorsey Built Twitter and Square: A Tale of Two Tech Giants

Jack Patrick Dorsey was born on November 19, 1976, in St. Louis, Missouri. Even as a child, Jack was different. While other kids were playing outside, Jack was captivated by the intricate patterns of the world—city maps, computer programs, and the rhythm of life in motion. His father, Tim Dorsey, worked for a company that developed mass spectrometers, which may have sparked Jack’s early interest in technology.


Dorsey’s fascination with the way cities operated led him to discover dispatch systems—those used by taxis, ambulances, and emergency services to coordinate movements across a city. The complexity of these systems captivated him, and by the age of 14, he had already written open-source software for dispatch routing. It was this early exposure to real-time communication and the flow of information that would later become the foundation of his biggest ideas.


After graduating from Bishop DuBourg High School, Dorsey enrolled at the Missouri University of Science and Technology. However, he quickly realized that the traditional academic path wasn’t for him. He transferred to New York University but dropped out before completing his degree. Dorsey was driven by a desire to build something tangible, something that would make a real impact on the world.


The birth of twitter


In the early 2000s, Jack moved to San Francisco, a city that was quickly becoming the epicenter of tech innovation. He joined a small podcasting startup called Odeo, founded by entrepreneur Evan Williams. At Odeo, Dorsey was tasked with developing new ideas. It was here that his early fascination with dispatch systems began to resurface, this time with a new vision—a way for people to broadcast short updates about what they were doing to their friends and family.


Dorsey’s idea was simple, yet groundbreaking. Inspired by the dispatch systems he admired in his youth, he envisioned a platform where users could send short, SMS-like messages to groups of friends, letting them know what they were up to in real time. The concept was pitched to the Odeo team, and despite initial skepticism, it gained traction. Dorsey, along with co-founders Biz Stone, Noah Glass, and Evan Williams, began developing the project under the codename 'Twttr.'


On March 21, 2006, Jack Dorsey sent out the first tweet: 'just setting up my twttr.' With this simple message, Twitter was officially born. The platform allowed users to send messages, or 'tweets,' of up to 140 characters, a limit that was originally set due to SMS restrictions. Little did Dorsey know, this small startup would soon become a global phenomenon.


Twitter quickly caught on, first among the tech-savvy crowd in Silicon Valley, and then spreading like wildfire across the globe. It became a new way for people to communicate—direct, concise, and, most importantly, public. From tech conferences to celebrity endorsements, Twitter began to gain momentum, becoming a hub for real-time information.


But Twitter's meteoric rise wasn’t without its challenges. As the company grew, so did the pressures of running a rapidly scaling tech startup. Dorsey’s leadership style, described by some as aloof and unfocused, began to draw criticism from within the company. In 2008, amid concerns over his ability to lead, Dorsey was replaced as CEO by co-founder Evan Williams. It was a tough blow, but Dorsey wasn’t done with innovation yet.


The birth of square


After leaving his day-to-day role at Twitter, Dorsey found himself at a crossroads. But it wasn’t long before a new opportunity arose. A conversation with his friend Jim McKelvey sparked the idea for Square. McKelvey, a glass artist, had lost a sale because he couldn’t accept a credit card payment. Dorsey realized that small businesses needed a simple and affordable way to process credit card transactions. And thus, the concept for Square was born.


Dorsey and McKelvey set out to create a device that was both elegant and functional. The result was the Square Reader, a small, square-shaped device that plugged into a smartphone's headphone jack, allowing anyone to accept credit card payments anywhere, anytime. The simplicity of the design was its genius—suddenly, small businesses and entrepreneurs had the same payment processing power as large corporations.


Square launched in 2010, and it didn’t take long for it to become a game-changer in the world of finance. Small business owners, who had previously been locked out of the complex and expensive credit card processing market, now had a tool that was easy to use and cost-effective. Square democratized financial services, empowering millions of small business owners across the country.


But Dorsey didn’t stop there. He envisioned Square as more than just a payment processing company. Over the years, Square expanded its ecosystem, adding new products like Square Register, Square Capital, and Square Payroll. Each new offering was designed to solve the problems faced by small business owners, solidifying Square’s position as a leader in financial technology.



Return to twitter


In 2015, amidst growing concerns about Twitter’s stagnation and leadership turmoil, Jack Dorsey made a dramatic return as CEO. It was a critical time for the company, which had struggled with user growth and a clear strategic direction. Dorsey’s return signaled a new chapter for Twitter, one focused on rejuvenation and innovation.


Running one publicly traded company is challenging enough, but Dorsey was now at the helm of two. Balancing the demands of Twitter and Square required extraordinary discipline and focus. Dorsey implemented a strict routine, dividing his time between both companies, ensuring that neither was neglected. Under his leadership, Twitter began to roll out new features and policies aimed at improving user experience and curbing abuse on the platform.


Dorsey’s second stint as CEO saw Twitter achieve several milestones. The platform became a go-to source for real-time news and discussion, playing a pivotal role in global events from elections to social movements. Meanwhile, Square continued to grow, expanding internationally and introducing innovations like the Square Cash app, which made peer-to-peer payments easy and accessible.


Legacy and impact


Jack Dorsey’s impact on the world is undeniable. Twitter has become a cornerstone of modern communication, shaping how we share news, engage in dialogue, and connect with others. It has given a voice to millions and played a key role in movements for social change. On the other hand, Square has empowered small businesses by providing them with the tools they need to succeed in an increasingly digital world. Dorsey’s vision for a more connected and equitable world is reflected in the companies he built.


However, Dorsey’s journey hasn’t been without its challenges and controversies. Twitter has faced intense scrutiny over issues related to free speech, censorship, and its role in the spread of misinformation. Meanwhile, Square has been at the forefront of debates about financial inclusion and the future of banking. Yet, through it all, Dorsey has remained committed to his vision, constantly seeking new ways to innovate and address these complex issues.


Jack Dorsey’s story is a testament to the power of vision, persistence, and innovation. From revolutionizing communication with Twitter to transforming commerce with Square, his impact on the tech world and society at large is profound. But beyond the companies he built, Dorsey’s legacy lies in his relentless pursuit of a better, more connected world. As we look to the future, we can only imagine what new heights he will reach and what new challenges he will tackle. Thank you for joining us on this journey through the life and legacy of Jack Dorsey.

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