03/22/2013 12:01 pm ET Updated May 22, 2013

Why Twitter and Square's Jack Dorsey Should Run New York City

When Jack Dorsey's obsession with trains and systems was revealed on 60 Minutes last week, I almost fell over, recalling that I became an admirer of his in the midst of the busiest train terminal in the universe: Grand Central.

It was there that I first met Dorsey's baby, Square, while racing to purchase a pair of fingerless gloves before boarding Metro North to Connecticut so I could navigate another of Dorsey's creations, Twitter, throughout the frigid Manhattan winter. As a roving executive at New York Natives, I tweet my every movement, and I didn't want to have to remove gloves to do so. At a small Lexington Passage shop I selected a grey set, tried them on, then wiggled my digits like a grand pianist readying for a performance at Lincoln Center. "Yes, I thought, these fingers are keypad-ready for hail, wind, freezing rain and snow."

As soon as the pop-up shop's purveyor sensed that I'd committed to the special hand-wear, she approached me with her iPhone, which had an odd plastic attachment. "That's so cool," I muttered, as she showed me how to swipe my MasterCard and use my index finger to sign her phone. Some sort of technological high surged within me. In the midst of buying a simple pair of fingerless gloves, I realized that the world was changing. Before sobbing with delight, I grabbed my purchase and rushed to track 25.

Situated on one of the train's orange pleather seats, right beside the commuter clique, all I could think about was that white plastic square.

I could see how that little contraption could empower anyone with a mobile device to launch a business or to complete financial transactions more securely and efficiently. I also intuited that something bigger was underway. The year before, I hosted a TEDx entitled "New Wall Street", which focused on re-imagining banking for the information age. The truth is that banking today is an information science stuck in a 20th century machine, and even at times a Victorian design. At TEDx, we took to task the outdated use of the written signature, poor accounting practices, unfair and incomplete credit score systems, the dangers of black box trading, the borrowing hold-ups for small business owners and the challenges immigrant workers face in sending money back to their homelands. Maybe these people could use Square, I thought. I knew on some level that, as it evolves, Square could profoundly impact the international flow of capital.

Should I Tweet my Square revelation to the world, I wondered. And then, in the bowels of a tunnel, I lost cell phone service. As fleeting as a Tweet, the moment dropped down the news feed of my consciousness.

Now the man behind two of the greatest technological innovations of our day, Jack Dorsey, has announced that he'd like to be Mayor of New York City. New York City is the world's ultimate example of a civilization with innumerable moving parts operating in sync. In the name of evolving on a systemic level, New Yorkers do everything possible to break old norms and accepted standards of business, society and behavior. With Twitter, Jack Dorsey created a virtual space that facilitates the same kind of systemic harmony, on a global scale. Meanwhile, Square is revolutionizing business development and wealth management, just as Wall Street and the New York Stock Exchange did over a century ago.

Jack Dorsey the programmer was drawn to New York City at a tender age because he has a passion for systems. According to 60 Minutes, "As a teenager he created software that tracked the movements of emergency vehicles on a map." At 19, Dorsey tried to apply for a job with a large dispatch company in New York but he could not find the business' contact information. Instead, he found a security hole on their website, and hacked in to alert them to the problem. A week later, the dispatch company offered Dorsey a job.

Shy and reserved, Dorsey can find it difficult to communicate -- or so it was revealed on 60 Minutes. It even got him kicked out of Twitter for a while. So he may never possess the charisma or the hutzpah to be a Mayor Koch. But like fellow billionaire Mayor Bloomberg, Dorsey is a proponent of shared transparent spaces within his companies' offices. At Square, he doesn't even have an office. Dorsey would not be the in-your-face tough guy on legal issues and security that Rudy Giuliani was. However, Dorsey could very well be the right mayoral candidate to usher New York City into the next era by helping the city confront challenges in innovative ways so it can maintain its position as a world leader in the information age.

As urban populations explode, particularly the five boroughs of New York, Dorsey's interest in the cross section between art, engineering and utility could also serve us well. Dorsey deliberately holds company outings at a place in San Francisco where his staffers are treated to amazing views of the Golden Gate Bridge. His objective is to emphasize that when people stare at the Golden Gate bridge, they don't think about the commuters, but instead admire the structure's beautiful simplicity. Imagine if this philosophy were applied to low income housing and actually made residents feel good. The current design of these buildings makes the blaring statement that we care little about our city's working classes. Imagine if the renovation of our subway system incorporated technological advances out of Silicon Valley courtesy of the man who wrote the code for Twitter.

Of equal import, while Dorsey emoted during his 60 Minutes interview, it became clear that he possesses the intimate sense of humanity -- for the collective and the individual -- that is crucial for any New York City mayor. While discussing Twitter with Lara Logan at one point, he said, "It's so instant... and now I get to see the entire world and how they're thinking and how they're feeling and what they're doing and what they care about and where they're going." He cares.

Dorsey is definitely ready for the mayor's office. The real question: Is New York ready for Dorsey to run, or to win?

A version of this story was originally published on

Camilla Webster is the cofounder of New York Natives, the best selling author of The Seven Pearls of Financial Wisdom, the former anchor for and recently moderated TEDx New Wall Street: Re-imagining Banking for the Information Age in Silicon Valley. She was an invited guest to the first White House Tweetup Briefing in history, which focused on the American Jobs Act.