11/08/2013 12:57 pm ET Updated Jan 23, 2014

You Don't Know @Jack: My Visit With Twitter Co-Founder Jack Dorsey on the Occasion of Twitter's IPO

On my last total disruption go-round in the Bay Area, I ended up at Twitter HQ looking to find Jack Dorsey. I was following my crew over from filming at Lyft, via Class Dojo, so I was heads down in my "virtual box" and looked up to instant recognition: This was the site of another (upcoming) ATD episode with Russell Brand. On our tour of Twitter with Russell, we discovered that it's a cozy, bubbling place -- replete with a bar, laundry, showers, and yoga. Russell pointed out that there would be no reason to leave... But Jack had found one. So unfortunately, there was no time to participate in any of the fun that day at Twitter, but instead we tore down the street and several blocks over to find its founder: The sixth youngest billionaire in the United States, who only seven years ago was in debt. @Jack is quite busy helming his newest venture -- the completely disruptive and democratizing mobile payment app and merchant services aggregator, Square.

Soon enough, I found myself face to face with a graceful man, open and ready to engage on any topic I brought forth. I especially enjoyed hearing about how his mother and father fell in love, what moved him as a young man, his personal highs when realizing the power of Twitter, and why he made the switch from Twitter to Square. I had heard rumors that Jack was considering making a move to become the mayor of New York City, and thought to myself that I could see him succeeding in that pursuit. From the bespoke suit and rich blue eyes, to the kind demeanor and electric air that surrounds Internet royalty -- I was struck with the metamorphosis Jack had undergone from the nose ring-wearing punk rocker I'd heard tale of from his former associates.

In this week's episode of Wizard, we got to get personal with the controversial Twitter co-founder and Square CEO about his journey from college dropout to billionaire tech titan:

You Don't Know @Jack

In the recent New York Times piece "All's Fair in Love and Twitter" by Nick Bilton, Jack is portrayed as a fashion-obsessed, self-absorbed backstabber who stole the company from his good friend, Noah Glass, to secure his legacy and reputation as the lone creator of the service. Worse yet, @Noah was going through hard times and a divorce at the time, and confided in Jack that he was being pushed out by Evan Williams -- when Jack was apparently behind the ouster. I can't help but notice the parallels: First there was Steve Jobs who took full advantage of the socially-inept coding mastermind behind Apple, Steve Wozniak; then came Mark Zuckerberg, who had co-founder Eduardo Saverin sign away his stake in Facebook thinking it was a stock offering; and now it's Jack Dorsey and Noah Glass's turn (though it's important to note that @Noah tweeted congratulations and best of luck upon hearing of that Twitter was going public.)

In the run-up to Twitter's successful IPO (initial public offering), it was with a twinge of sorrow that I read all the dirt dished on co-founder, Jack Dorsey. 75% of startups fail, so when an idea hits the jackpot and mega-money floods into the picture, we notice time and again that egos expand rapidly and friends turn on each other. Why does our piece of any pie look smaller to us as that pie gets bigger? Is it the 500 count sheets that allow us to sleep at night after we screw our partners out of the spoils just before that victory lap?

Still, as lawsuits were filed, mud flew around the enormous wealth the IPO generated for its creators, and skeletons got dragged out of the closet -- it's easy to forget that the key to Twitter's success is how it allows people to make connections in real time, creating a virtual map of our hive mind (and the exchange is overwhelming, which is why the 140 character limit is a crucial component.) So, for today, I want to focus on this brilliant disruption, rather than the darker side of human greed.

Twitter may only have 230 million users worldwide, a fifth of the size of Facebook's 1 billion users, but nonetheless it is certainly my first port of call online. What at first was an alien experience to me, navigating the SMS-based etiquette and hashtaggery of the platform has become an extremely efficient, transparent, and powerful vehicle to share and receive the latest news and happenings from around the world. Often times, I take my tweets and "turn them into English" (by removing the @'s and #'s, adding descriptions that won't fit in a tweet, etc.) and then throw it onto Facebook as an afterthought. On Facebook, I have thousands of "friends" who are much more excited about pictures of my son and lizard, or me in a dress on a red carpet, than any posts I make about my my films or web series. It's the opposite on Twitter.

Furthermore, Facebook mediates our interactions with some mysterious algorithm, determining which of our "friends" will even get to see what we're sharing. Whereas with Twitter, what we put out there goes to our "followers" and vice versa, unmediated by some big brother-esque third party. I also appreciate that Twitter didn't degrade the notion of what a "friend" is (however, the word "follower" does conjure up cults in my mind, which is also creepy.) Most importantly, on Twitter, I find a rapid exchange of ideas and the potential to mobilize real, physical world action on a global scale. And I'm not alone in this assessment: Twitter's IPO was already oversubscribed and was more expensive than its social media big brother, Facebook.

Twitter's genius was that it pointed out the inefficiency of receiving top-down information and the irrelevance of bloated media behemoths ossifying in glass studios. Nearly 1 in 10 adults in the US now gets news from Twitter. They are younger, more educated and more mobile than news consumers overall. A whole generation is growing up and piecing together their news and information diet in bursts of 140 characters. This burst serves as a headline quite often, with a link available in which to take a deeper dive. During the Arab Spring and recently in Syria, Twitter was the revolutionary vessel by which the powerless communicated, coordinated, and challenged political authority. As Jack Dorsey says, "Twitter is great at providing that man on the street account. The flavor of what's happening. The roar of the crowd."

From a young age, Dorsey, a Saint Louis native, wanted to see the "city living and breathing in real time." A self-taught programmer, he filched his parent's police scanner and began building crude city maps on his home computer, first simulating the paths of ambulances, and later adding data sources like police cars, taxis, and trucks.

Eventually, he moved to New York City and continued his obsession with mapping at a dispatch routing company, "I could see the city. I could see it live, I could see it breathe, but I was missing one key element. I was missing the people. Where were they? What were they doing? Where are they going?" It would be years until he added that component with Twitter.

Timing is everything, but so is persistence. Dorsey tried to build a simple system in 2001 that accepted an email from a BlackBerry pager that would then go out to a list of all his friends. He quickly discovered two things: 1. Nobody cared and 2. Nobody had a BlackBerry. The concept didn't die there, it just went dormant until the technology could catch up.

Like most ideas that come out of Silicon Valley and captivate the world, Twitter began as something entirely different -- a podcasting service. It's a classic pivot story. Around 2006, after dropping out of two colleges, Dorsey was out in San Francisco and joined Odeo, a company founded by Evan Williams and Noah Glass. It was the first time Dorsey had written a resumé and taken a real job. He explains why he jumped at the chance to join Odeo: "I took it because I was inspired by the people working there. And I was not inspired at all by podcasting. I wasn't a podcaster. I had no interest in the service. And I quickly learned that no one else in the company had an interest in podcasting either." Odeo was on its last legs, and during one of their "Hack Days," Dorsey shared his idea with Glass who made it more about communication and obsessed over it until he landed on its name. They introduced the long-germinating concept to his fellow team members, and Twitter was born.

Twitter didn't set out to just change communication, but to democratize the way we connect with each other. Dorsey and team chose 140 characters, because they wanted to build a service that anyone on the planet could use, with any device. Someone in Kenya with a $5 cellphone could have the same conversation as Justin Bieber on his iPad. Not just that, but Dorsey believes that the constraint of 140 characters produces greater creativity while allowing people to express themselves more freely: "140 characters allows people to be more of the moment. Off the cuff. And less shy. Less composed. So they can really say what they feel."

One day after @Jack moved from CEO to Chairman of Twitter, he reconnected with his first technology boss, glass artist, Jim McKelvey. It was a practical annoyance that his old friend encountered that would trigger Dorsey's next big idea, "Jim called me one day in frustration and said he had just lost a sale of a piece of his glass art, because he couldn't accept a credit card." Dorsey thought that was ridiculous, and also saw an opportunity to avoid being a one-hit wonder.

So Jack and Jim teamed up and launched Square -- a platform to accept debit and credit card payments on a mobile device like an iPhone, which has jump-started a small business revolution. Dorsey enthuses: "Square enables anyone to start a business -- to do what they want. It's the difference between doing something you love and doing something you have to do. And the number of small businesses, the number of independent businesses...has never been growing at a faster rate."

Amid all the accusations and criticism that swirled around Twitter's IPO, Dorsey, who added around $1.05 billion plus option to his fortune, remained relatively silent, instead focusing on the future of Square, which processes $15 billion annually in credit card transactions -- not to mention a deal cut last year to handle all of Starbucks' card payments. Who knows what's next for this massively successful disruptor: Maybe his love for cities will ultimately push him to throw his hat in the ring for his dream job, and he'll follow the newly-elected Mayor Bill de Blasio in running New York. After watching Tony Hsieh work magic in Downtown Las Vegas, I am inclined to support more badass tech entrepreneurs guiding city planning -- that's for sure.

Many people have ridiculed this idea, but @Jack has triumphed over the naysayers before: "We were being told no constantly for both Twitter and Square. With Twitter it was 'Why should this exist in the world? No one needs it.' With Square, it was 'This can't exist in the world.' So I operate by the principle that if I believe in something, I fight like hell for it."