Jack Dorsey to entrepreneurs: Don’t sell out too soon

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The Globe and Mail sat down with Twitter chairman and Square CEO Jack Dorsey ahead of his recent appearance at AccelerateTO, a startup event from the C100 network. Mr. Dorsey, 36, is expected to become a billionaire when Twitter completes its IPO, but the polymathic coder-cum-entrepreneur has already shifted from communication to commerce with his payment app Square, which has now processed $16-billion (U.S.) in transactions from Canada, the United States and Japan.

He had several bits of counsel for entrepreneurs. In his own words:

Disruptions don't add value

I don't like the word disruption, I don't think that's the right approach … it's just moving things around. It has no order, or values or purpose whatsoever. [Entrepreneurship is] not discovering a market that's underserved or undervalued or underinvested in … it's building what we want to use and then doing whatever it takes to make it real.

Don't sell out too soon

I think there are a lot of companies that shoot for the market but don't shoot for the world. [After visiting Waterloo, Ont., Mr. Dorsey observed] there are a number of companies who have sold early and not really gone after global success, and that's not just Canada, that's a lot of places in Europe as well. It would be good to see some companies out of Waterloo really bring it to a global scale.

How to go global

An Instagram or a Vine can bring their product to the world, and the entire world can use them and you see linear growth, and when they translate it you get this hockey stick [growth chart]. Square isn't like that because we do have to work with the local banks and regulation. So it's a little bit different.

The way we're operating right now is that we're going to serialize markets, and as we get better and have more of those conversations we are going to parallelize them. But we only have so many people at the company … so much ability to focus on the right things. We want to build a really strong platform in a place where we can see it every single day, and then really expand it.

Decision making

You have some folks and companies in the world who operate purely on intuition, and some who are purely data driven. I always find that life is in the balance; there is some balance between those two that will work. We strike that balance in Square, we're going to make intuitive bets because they feel great to us, and then we're going to prove it with the data.

Square's role in the entrepreneur and small-business sector

We've done some compelling data visualization around the impact of small business on the community. No one is having the conversation around what is the small business impact on the economy, and we think it quite large and we think its trending up very, very quickly. If we can help create a very strong network of small business that are increasing their commerce, I think we've done a great thing for the [broader] economy as well.

Entrepreneurial heroes

Definitely respect and admire Elon Musk and everything he's doing. I think it is foundational – transportation both to space and electric vehicles. He's also operating, just like every great entrepreneur, in a very selfish way: Elon wants to go to space, he wants to live on Mars, and he wants to be the first person to do that, and good for him. He also wants to drive really fast and have no emissions, and good for him.

"The spirit of entrepreneurship"

You want to want to see something in the world because you want to use it on a daily basis, and you're making the bet with yourself and the world that other people want to see the same thing. Sometimes you lose the bet, sometimes you win the bet; we won the bet with Twitter and Square.

Entrepreneurship comes in many flavours

Entrepreneurship doesn't necessarily mean you're starting a company, it just means you are taking significant risk in order to see something new. You can do that by building a company or you do that within a company … or an organization or even in government.

His pitch: Square is not about payments, it's about data

We see our business with payments is something we have to do to provide the interesting stuff. Where we find the most meaning, where our sellers find the most meaning, is around analytics: the data about their business. It's knowing what their busiest day is, knowing what the most popular item is.

These are all things we've taken for granted on the web, we get page views and clicks, and all these things. Offline merchants – which are still 94 per cent of commerce in the world – don't have any of this data unless they buy a $15,000 point-of-sale system. We offer it for free [to Square merchants].