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Illustration of Jack Dorsey, co-founder of Twitter and Square. (ANTHONY JENKINS FOR THE GLOBE AND MAIL)
Illustration of Jack Dorsey, co-founder of Twitter and Square. (ANTHONY JENKINS FOR THE GLOBE AND MAIL)


Twitter’s Jack Dorsey: The startup king plugs his newest venture, Square Add to ...

Jack Dorsey has a thing for coffee shops.

When 60 Minutes did a segment on him last year, he brought the television crew to the shop around the corner from his office to demonstrate how easy it was to use Square, the payment and commerce company he started during – what shall we call it? – a break from the other company he founded – Twitter Inc.

When he agreed to meet me, it was at a coffee shop in Toronto’s Junction neighbourhood, where I’m met by a crowd of people shivering near the door, wondering if there’s any room inside. That’s because there’s a CNN crew there – Mr. Dorsey is in demand. He’s visiting Toronto for a day to talk about Square Inc., but CNN and most other journalists just want to talk about his first startup, the one on its way to a $1.8-billion (U.S.) initial public offering: Twitter.

I am invited inside Hula Girl Espresso Boutique (a Square Register client, naturally) as CNN wraps up, breaking down lights and tripods. Mr. Dorsey is sipping a bottle of Odwalla juice (he was a vegan, but reportedly is now a paleo dieter). He joins me at a standing table made of one big cross-section of a tree trunk.

Mr. Dorsey is a ground-floor founder of two of those rarest of unicorns in Silicon Valley – the billion-dollar startup. By some reckonings, there have only been a few dozen such firms to reach a 10-digit valuation in the past decade (the company was valued at more than $22.6-billion Friday afternoon), among them such public companies as Facebook, LinkedIn, Groupon, Yelp and even the once-mighty Zynga. He got there by making things he wants, and betting others want them too. In Twitter’s case, he and his co-founders wanted to create something that resembled the dispatch radio systems he had worked on in the past, and with Square, he wanted to give small merchants the ability to take credit cards for homemade goods or services.

Mr. Dorsey’s part in Twitter’s founding has been the focus of some debate.

The company’s first CEO, he was forced out in favour of co-founder Ev Williams in 2008, but staged a comeback three years later when the board flipped on Mr. Williams, named Mr. Dorsey executive chairman and partnered him with a new CEO, Dick Costolo. Some say he painted an overly generous picture of his place in the company’s founding myth, edging semi-tragic figures like Noah Glass completely out of the picture. When Twitter went public on Thursday, priced at $26 a share, Mr. Dorsey didn’t get the biggest payday – Mr. Williams is the largest founding shareholder.

An entire book could be written about who really started Twitter (one was recently published, by New York Times reporter Nick Bilton), but “it’s not the story,” according to Mr. Dorsey.

“I think companies have to have multiple founding moments, not just one. There’s way too much emphasis placed on the initial one. I don’t think it’s fair or realistic,” he says.

By way of explanation, he mentions the Founding Fathers, canonized in the United States as near infallible constitution-writers. They “had some good ideas about creating a nation … but the best idea was captured in the phrase ‘A more perfect union.’ ” To Mr. Dorsey, that suggests Thomas Jefferson, John Adams and Benjamin Franklin knew “they were not going to get everything right, that other people were going to come up and refound a nation.”

He talks about how the lack of analytics played a role in what was happening with the exploding “hockey stick chart” growth of Twitter in the mid-2000s. “From the earliest days of Twitter, when we just didn’t have a lot of analytics … and we just didn’t know what was going on. That creates a lot of speculation in the company, and then that creates a lot of contention, arguments and debate.”

Business analytics may just end up being his next startup’s killer app.

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