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Jack Dorsey: Twitter co-founder, Square CEO, punk

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Update June 11, 2015Twitter CEO Dick Costolo is stepping down July 1, and Jack Dorsey, one of the original founders of the company, will fill in as interim CEO.

You have about a 0.00006 percent chance of starting a billion-dollar business. Jack Dorsey didn’t just start one — he’s got two.

Dorsey was 29 when he launched Twitter with his pals Evan Williams, Biz Stone and Noah Glass back in 2006. His handle, @Jack, is Twitter’s first personal account.

Since then, he has launched Square, a mobile payment company that he hopes will change the way we pay for thngs. You’ve probably used Square at an independently-owned store or restaurant. It’s a little white minimalist card reader that plugs right into an iPad or iPhone. The company has also gotten into organizing, and even lending. It’s hoping to be a one-stop-shop for small business owners.

Dorsey talked about Square and his life since Twitter at Dig Wines, a wine shop in San Francisco — where, by the way, Square readers are at the cash register.

Square’s “aha!” moment:

It was really our founding moment when our co-founder Jim McKelvey, who was my boss when I was 15 years old back in St. Louis Missouri, called me and said he just lost a sale of his glass art because he couldn’t accept a credit card. And he was calling me on his iPhone which was a super computer… We have all this power in our hands, but why couldn’t we do a simple thing, or something that seemed as simple, as accepting a piece of plastic? Which is far more convenient than cash, far more convenient than a check. Why isn’t that possible? The company is an answer to that question.

On how Square works:

The insight really came from looking at the back of the credit card and the back of the credit card is a magstripe. And a magstripe is really the same technology that a cassette tape is. It’s audio. If you listen to the audio on a magstripe, it sounds like a squirrel screeching really loudly. You know, if you put a read head next to that, then you can decode that audio into numbers and those numbers you can send up to processors. All that was required was an audio jack that didn’t just put sound out but also had mic in, and every iPhone at that time had a mic in ring that we just plugged into. Suddenly, we were able to push that audio into and decode those into numbers.

On what he does as a CEO:

First, assembling the right team. (That means) hiring, certainly, but it also means parting ways with folks that just aren’t cutting it…making sure that we’re paying attention to that team dynamic and [that] it’s collaborative and it’s really challenging itself. Number two is making sure decisions are being made. I say that if I have to make a decision, we have an organizational failure. (That’s) because I don’t have the same context as someone who is working day to day with the data, with the understanding of the customer. I definitely see the organization and the people in it as the ones to make the decisions, because they have the greatest context for what needs to be done.

On how his experience with Twitter affected how he started Square:

I was a first-time CEO. It’s not a position I necessarily wanted to be in. It’s a position that I was grateful for but was put in, and we were growing extremely extremely fast. But what I took from all of that is how important it is to really focus on the fundamentals. And the fundamentals that I found were the company and the team, and Square was interesting because we definitely made new mistakes, because I wasn’t going out and saying “Well I’m going to get into microblogging again.” We did something completely different and we got into finance. When I started Square, I was in credit card debt. I had a terrible FICO score. I lived all the pain that our merchants live every single day. We took those lessons and we baked it into the product.

On the connection between emotion and finance:

When I walk into a place like this (wine shop), there’s an emotion. When I take this bottle of wine home after I purchase it, there’s an emotion. No matter how much of our life moves online, we will always have places like this where we come together. We trade stories. We communicate. We see each other, and I think it’s a mistake to extract the soul from commerce because it enables a lot of these experiences that we treasure for the rest of our life. 

On Square’s legacy:

I definitely want Square to have a massive impact, and I think it has the potential to be that. I’m going to work as hard as I can to make sure that’s the case. Really what that means is that that’s accessible to more people.

Predicting the first line of his obituary:

Jack Dorsey, punk.

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