The Real Jack Dorsey

Jack Dorsey

Now it’s not every day Jack Dorsey founder and CEO of Twitter and Square, slips into town. Not only did I get to meet him but he was kind to enough share his advice…and it’s hard not to take his advice, considering Twitter has reached over 500 million users.

So who is the real Jack Dorsey? His public reputation paints him as impassive, impersonal and imperturbable, yet he insists that this is not a true representation. He is capable of heated displays of emotion, which he puts down to his Italian ancestry on his mother’s side.

“I’m half Italian you see. The Dorsey side was always pretty quiet and reserved, but the Italian side, you would often find food being thrown. I’m definitely more the Italian side”.

39-year-old Jack Dorsey’s resume might be considered one that many would be happy to have achieved in a whole lifetime. His first enterprise, Twitter, has an estimated valuation of $20 billion and reaches more than 500 million users. His other business, financial services mobile payments company Square, is valued at over $6 billion making it more valuable than all but the largest American banks.

But Jack Dorsey is no “normal” entrepreneur, and his expectations aren’t either. It’s a mentality that is evident when he discusses his companies and how far they have to go.

“I don’t feel we’re at even 1 percent of our potential with either company”

Considering Dorsey’s opinion of where his enterprises are, it’s hard to imagine what goals he has set for them. If the tripling of transactions on Square in the past 18 months and the estimated 500 million users on Twitter are signs of companies that have yet to fulfil a mere hundredth of their potential, then the question becomes obvious: How far, exactly, does Dorsey expect them to go?

But if confusion is the feeling that follows, it’s likely because Dorsey is doing the dirty work while everyone else is on the outside looking in.

“If you’re climbing on the mountain, it doesn’t look that massive to you”

Listening to Jack Dorsey talk about his entrepreneurial interests isn’t all about head-scratching, though. All it takes is for him to explain how his goals go far beyond what the eye can see for observers to truly understand the massive size of Dorsey’s metaphorical mountain.

“We don’t want this to just be about payments, we don’t want it to be about transactions,”  in regards to Square’s mission, “Those are all mechanical things that should be so intuitive that they disappear.”

His message is clear. He wants Square to be more about the service it provides. The purpose of the device, he says, is all about giving small business the opportunity to focus on selling and growing. Any individual, for example, began selling their services right away without having any traditionally formal setup (cash register, etc.) and can thus focus on growing instead of being held back, Dorsey explains. The knock-on effects of creating and perfecting a product like Square, is the big picture that Dorsey focuses on, adding,

“a lot of people are only looking at parts of the equation, but Square is looking at the entire thing.”

While cynics might think that the entrepreneur is indulging  when it comes to talking about his goals — they might argue that, after all, running businesses always comes down the bottom line, making money — Dorsey says it’s in the nature of those who are in the tech world to think about the way in which products touch people because that’s what advancing technology is all about.

He says he commutes to work by public bus every day, for professional reasons as much as ecological ones—so he can look over  passengers’ shoulders to see which smartphone apps they are using, and how.

“What I think is great about technology, and every technology that exists, [is that] it increases the number of people who can participate, in our case commerce, and it increases the velocity that they can participate.”

The launch of Moments, a curated section of Twitter that organizes tweets into narratives around breaking news events, is part of a changing long-term strategy at Twitter.

“Moments represents a real shift in our thinking, it questions the reverse chronological timeline. Moments is a bold new experience that I think does question a lot of our fundamentals. Moments is one piece that makes all of Twitter better and easier to understand. There will be many more pieces to come.”

So, as Twitter continues, amongst other things, to provide a platform for more organizations and social movements to broaden reach and as Square continues to provide opportunities for the most modest of businesses to grow, the beneficiaries of those services can bank on one thing.

Jack Dorsey will be expecting to deliver more of the same in better and faster ways as he leads the way forward with his companies looking to fulfil the “other” 99% of their potential.

So what can Jack Dorsey reveal about the secret to his success?

Here are ten suggestions he believes will help you stay on track. The last one has the most validity no matter what field you want to venture into!

Don’t be a jerk

Be honest, always

Be true to your word

Respect people’s wishes

Don’t take anyone for granted

Enjoy the moment

Be humble

Be kind

Have a tipple of choice (his is tequila…nice!)

Allow endings

Fail openly

Have an amazing haircut

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