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the lunch

Illustration of Jack Dorsey, co-founder of Twitter and Square.ANTHONY JENKINS/The Globe and Mail

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.

During his time in the wilderness, Mr. Dorsey was also spending time starting Square, which provides a flat fee, low-infrastructure tool that gives just about anyone to process credit card payments. It works via a small plastic device that attaches to a smartphone or tablet and reads information on a credit card's magnetic strip. It's great for previously cash-only businesses, but Mr. Dorsey's enthusiasm really sparks when he talks about the data the transactions generate (it's one of the reasons he says it's a mistake to call Square "just" a payment service).

Coffee shops enter here as well. On both occasions I've encountered him, Mr. Dorsey referenced a Times story on independent coffee shops in New York outnumbering Starbucks and Dunkin Donuts as proof of people craving "local, personal neighbourhood experiences." His mother started a coffee shop in St. Louis when he was a young man, and he learned to make espressos and cappuccinos there. Slinging java and muffins is his default metaphor for explaining how merchants can use Square for analytics on their business: In one example, a baker uses Square Register to realize she's not selling all the croissants she's making, her staff are eating a big chunk of her inventory.

"Every time someone swipes a card, we send an e-mail to the merchant saying 'you just made a sale.' This is like a joyous moment for anyone building a business. When they see it working [there's] this sense of," and suddenly he flaps his hands and makes a noise like a machine operating or a balloon rapidly deflating, "jee jee jee jee, all these e-mails suddenly, like, wow, my business is growing … I can see it growing in my inbox … it was stunning."

The sense of how your company is doing is powerful (Web services are spoiled by things like page views and unique visitor counts, it is still very rare in the brick-and-mortar retail to get data like that). His manner is earnest and friendly, but he tells jokes in the same rapid, low monotone with which he compares himself to the Founding Fathers or reels off lines such as this: "We want to build a technology, a service and a company that reaches every single person on the planet." You have to watch the slight smile that twists his lips to know when he's making a joke and when he is dead serious about the potential market for Square.

"… Commerce is fundamental. People all over the world – every single person around the world – goes through at least one transaction a day, usually around food, and we want to make that easy."

Square has processed more than $100-million in payments in Canada since its launch here in October of last year, and gross payment volume tripled from the first quarter of 2013 to the second. Adoption rates in Canada have so far been 25 per cent higher than in the U.S., and our average transaction size is greater (about $120 to $70).

The range of services Square offers for buyers and sellers is broadening all the time in the U.S., but is more narrow in Canada. There's no "pay with your name" Square personal wallet here, for example.

There are barriers to setting up some of the commerce technology Square dreams up here (banks, telecoms, regulators, etc.). And there have been some recent examples – Verizon, Allstream – that suggest Canada is a less than welcoming place for international companies to do business. Mr Dorsey hasn't seen it. "We haven't had the experience where people are saying no to a lot of these things," he says.

"We also operate with the principle that we're not going to go up to Canada and tell them that this is the best solution ever. We're going to show them that this is something that can be very powerful; this is something that people want. We'll let the market prove it themselves."

One of the things he is fond of saying is "Creativity comes from constraint." Most would say successful companies (Square is valued at $3-billion and hasn't needed to raise new money in a year) have fewer constraints, but Mr. Dorsey finds winning creates its own problems: "It's bad because you start developing more bias. 'This is our core business, we don't question the core business, we don't change this.' As companies grow … they don't want to mess with something that works. We always have to have a fight against that.

"No matter how big you are, no matter what you do, your No. 1 concern – whether you're Facebook or Twitter or Square, or the coffee shop around the corner – is 'How do I get new customers?' And then, once I get those customers, how do I retain them? Every business has this same problem, so there's universal threads between all of these that we're just trying to pick away at what's the essential thing to do this."

There he goes again with the coffee shops. So, other than satisfying his café fixation, what's next for Mr. Dorsey? What new billion-dollar startup lurks in his mind? Maybe none, for now, as he seems content with the gigantic scope of his current ambitions.

"I can't think of anything more foundational than communication and commerce – they are two very, very large canvasses," he told a roundtable of journalists in September. "I think if I spend the rest of my life enriching that and going deeper into those two, I think I've done a very, very good thing, for myself anyway, and hopefully for the world."



St. Louis, Mo., on Nov. 19, 1976


2011-present: Executive chairman, Twitter Inc.

2009-present: Co-founder, CEO, Square Inc.

2008-2011: Chairman, Twitter.

2006-2008: CEO, Twitter.

2005: Coder, Odeo (Founder Evan Williams's precursor company to Twitter)

1999: Moves to San Francisco, starts dNet dispatch service (it does not survive the dot-com crash)

Net worth: Stake in Twitter valued at over $1-billion (U.S.), stake in Square is larger by percentage (reportedly under 30 per cent), but privately held company's valuation varies from $2- to $3.5-billion depending on metric used.


1995: University of Missouri-Rolla (later renamed Missouri University of Science and Technology)

1998: New York University

2002: Takes courses in massage therapy


I had him do a word association with some of the leaders in the tech world:

Larry Page: "Innovative."

Mark Zuckerberg: Laughs… "There's so many words … the first thing that comes to mind is social." Him or what he does? "Both."

Jeff Bezos: "Confident."

Bill Gates: "Brilliant"

Elon Musk: Looks at his staff and laughs. "We have a bunch of ex-Tesla people [here]. Risk-taker."

Steve Jobs: "Brilliant. I can use it again."

Tim Cook: "Uhhhhh, focused."

Dick Costolo: "Uhmmm… Funny."

On disruption versus creating something new: "I don't like the word disruption, I don't think that's the right approach … because it's just moving things around. It has no order or values or purpose whatsoever.

"Twitter, for instance, has no reason to be. That's the feedback we got from all of our early investors, or not our investors but the people we [were] pitching to: 'Why should this exist?'

"So that I think was an entirely new creation and it's because we wanted to see it in the world, we wanted to use it."

Heroes: "I really have a bunch of heroes – I really like Richard Branson and what he's done. Both from constantly inventing and innovating, and starting complete left-turn companies.

"A lot of them have failed, a lot of them have succeeded; it doesn't slow the guy down.

"He's still jumping off planes and starting new companies while he's jumping off a plane. Like, he's calling on the way down, 'I have an idea!'"

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