His punk youth, of piercings and colored hairs, contributed to Jack Dorsey, founder of Twitter, the rebel quota to not give up when it seemed that his career was going to bite, while his personality calms down (he meditates and makes silent retreats frequently) led him to shuffle and give again when he thought the story was repeated.It could be said that he shares some characteristics with Steve Jobs - an artist who was expelled from his own creation and returned, redeemed, to reverse his history -, although on a smaller scale."Twitter is like a public square," says Dorsey. The first sketches were by hand and with them I wanted to combine the almost archaic text messages of the phones -SMS- with the idea of ââsharing all real time. "Something that was alive," he outlined in 2000.There was still a lot of water to run under the bridge. In that interim, until the creation of the platform in 2006, Dorsey was going to leave the university, work as a programmer, as a baby sitter, take 1,000 theoretical hours to obtain his card as a therapeutic massage therapist and even be banished from his own startup.In 20 years, the executive reinvented himself again and again. The result was a success: today he directs two of the most famous technology giants in the United States: the aforementioned social network and Square, the total reference of the fintech universe. His fortune, meanwhile, exceeds $ 5 billion.On the edge of failureA bit of mischief led him to get his first job. Bored during one of his classes at the University of Missouri University of Science and Technology, he thought it might be fun to hack a courier company and then show the CEO himself the failures of his system.He did and he offered a position in exchange for leaving his studies. Dorsey accepted. Then he would return to study, this time at the University of New York, although he finished his university stage in 1999 but without a degree in his CV. Then, he chose to move to California and found his first company with Greg Kidd, an executive he had dazzled.From a young age he had been fascinated by programming, however, his enthusiasm had a limit. "I studied other things, not for interest in that particular subject, but because programming is too abstract. I was constantly lost because sometimes you are so in your own head that you even program while you dream," he confesses.That's how he took fashion design classes, something that would later cause serious problems with the founders of Twitter. And he obtained his license as a massage therapist, a practice in which he began as a result of pain in the carpal tunnel.In 2002, the idea of ââthe bird's social network was a seed; Meanwhile, its first web services startup had begun to work. The relationship with its partners, not so much. After several confrontations about the company's direction, the board voted to leave and Dorsey returned to his native St. Louis.Several projects went through his mind. Three years later he returned to California, asked Kidd for accommodation in exchange for taking care of his children, while doing temporary work on Craiglist, the most popular classified website in the US. And as in the movies, a fortuitous encounter would change the countenance.Evan Williams already marked presence on the techie stage. In 2003, he had sold Google Pyra Labs (a company with which he had created the Blogger content publishing service) and was running his new podcast platform, Odeo. Dorsey saw him in a café in San Francisco and came over to talk to him. A little later, I was working in the company.It seemed that everything was going well until it started to go pretty badly, when Apple announced that it would include podcasts in its iTunes player, which completely changed Odeo's business. However, as the proverb says, every crisis contains an opportunity.Out of the cageAfter being in the cat for years, it was time for the Twitter project to come to light. Dorsey presented him in a hackathon organized by the Williams company to define the course he would take. The idea quickly hooked the executives and weeks later the ‘Twttr’ prototype was ready, as it was called at the time.Twelve years it took the social network to earn money. They spent several periods with accounts in red while their executives repeated, almost like a mantra, that he was trying to find the return to monetize it. Finally, in 2018, the numbers turned green.More than $ 1.2 billion of profit the firm achieved last year, a notable growth considering that until 2014 it reported losses close to $ 600 million.As a counterpart, the focus of concern became the fall in total users: last December it registered 321 million assets, almost 10 million less than in the same month of 2017."You can be a designer or the CEO of Twitter, but not both," said Williams snapped at Dorsey. The platform, which debuted in July 2006, gained popularity during its presentation at South by Southwest, the most important innovation festival in the world.Of course, some problems come with fame. For example, that the service is frequently dropped and that the number one of the company does not have any type of backup for its operation. To this was added that Dorsey used to leave early to go to her yoga and design classes.Such a situation led to a point of no return: Williams took over in 2008 and he was relegated to having a chair on the board. It was time for his revenge. First, he began to tell his version of the company's foundation in the media. "I felt that I was being deleted from the Twitter story," he said. The next step was to demonstrate that he was trained to lead his own venture.Perhaps that is why he founded the fintech of payment processing Square, which made it easier for small and medium businesses to pay by credit card: last year he invoiced $ 2,471 million. In turn, he became an investor angel of Foursquare. When he launched this company, he knew that the public only expected it to fail. So he addressed his doubts head-on: in a bold move, he presented to the financiers a list of 140 reasons (alluding to the 140 characters) why the business might not work.The "trick" had an effect: investors joined the startup and now Square is a leader in the mobile payment industry in North America. With that initial list, Dorsey showed that he knew the industry and the potential of his ideas.The return of the prodigal sonMeanwhile, on Twitter, Williams left his position as CEO of Dick Costolo, who would later leave the chair in 2015. And where did all the guns point ...? That was how Dorsey returned to the position he had left seven years earlier, this time as interim executive director.A few months later they would confirm him as permanent CEO, a chair he also occupies in Square. It was not the same as years ago: he had dabbled in the world of meditation, made spiritual retreats in the East and, as part of his daily routine, he took ice baths to wake up. He only consumed one meal a day, which involved frequent fasting.The only thing he kept from his punk era was his nose piercing, which he had set aside when he assumed as CEO of Twitter in 2006. Unlike other directors of large companies, he decided at the beginning of his successful project that he would not receive any compensation of the company.A decade after creating Twitter, the billionaire received his first salary for a symbolic amount: $ 1.40 (yes, one dollar and 40 cents). The amount was a nod to the character limit that Twitter imposed at the beginning of its creation (140), in 2006.A unique managementFor a moment he foresaw his future in politics. The idea of ââbeing mayor of New York prowled his head. Despite the abstractness of programming, he still sees it as a powerful tool to generate change."I can think of a law and its effects would not be felt for another eight years; instead, if I write a simulation, a code, and execute it, the results can be seen in eight seconds," he said.However, life at the head of the "Big Apple" could also get in the almost religious routine of sleeping eight hours a day, something uncommon among executives overworked. In this regard, he said: "I do not want to be a role model saying that I work 20 hours a day. Not only is it not healthy, but it is delusional."Given his controversial decisions, Jack Dorsey may not be the most popular CEO, but he is considered a great leader for his unique management style, which led to both Twitter and Square success.For this type of management to work, follow a series of established routines. The meetings, for example, are "highly regulated" with clear agendas and objectives. It also points topics for each day, such as business leadership or product development.Mondays, for example, convene a leadership meeting where their teams share what they will be working on in the week and the lessons learned from the previous week. On Wednesdays and Fridays, reserve 30 minutes of time to register and receive updates from your employees.For Dorsey, a good leader is someone who guides people in his organization so they can make big decisions, not someone who teaches them from above."If I have to be the one to make a decision, we have an organizational failure," he says. According to their perspective, the good health of a company does not depend on the power of its leader but on that of its members. Another peculiarity of his management style is his relationship with technology: he has no computers in his offices or in his home."I only have one iPhone, I got rid of my computer and my iPad. And the reason I like the iPhone as my only device is that I can disable notifications and it allows me to use only one application at a time. This way , I can concentrate on what I am doing, "he says."I love the freedom it provides and that everything I need is always with me. When I need time to think, to solve some kind of challenge, I know I can turn it off and it won't bother me."Some of their employees work shifts in coffee shops so they can see how the firm's services work in real life. The focus on usability means that customers leave satisfied. And that satisfaction is equal to the success of the company.