Exclusive: Twitter Founder on the State of Entrepreneurship

Jack Dorsey explains why times have never been better for entrepreneurs—even though the term is overused

Written by Igor Bonifacic

Jack Dorsey says his favourite thing about Square is that it incorporates the best practices it develops as it grows right into its product. The tech startup has grown from a three-employee operation to a multi-location, 600-employee business. “We’ve learned how to attract customers, we’ve learned how to keep those customers, we’ve learned how meaningful analytics can help entrepreneurs to make smart decisions,” says Dorsey. Now, Square provides analytics to its sellers to help answer questions like, “What’s my busiest hour?” or “What happens when I move the biscotti jar down to either end of the counter?”

Dorsey was in Toronto last week to host Square’s Let’s Talk series. The co-founder of Square (and Twitter) took to the stage along with local entrepreneurs. The group shared some of the challenges and rewards of starting a business. Dorsey spoke to PROFIT before the event.

Tell us about the genesis of the Let’s Talk series.

Let’s Talk came out of an internal event we have every Friday, which is called town square, where we talk about our business. We talk about what’s going well, what’s not going so well. We use a simple and friendly Q&A format that allows anyone in the company to ask any question. We thought about what would happen if we exported that to our neighbourhood in San Francisco. So we got a bunch of merchants together, and we asked them to talk about their business; we also invited the local community to come and ask questions.

I think that terms ‘entrepreneurship’ and ‘founder’ are overused, especially in Silicon Valley. If you really look at the meaning of those words, it has nothing to do with starting an organization or company.

The first one was a block away from our old office. We had 70 folks come and listen to these four merchants talk about what worked well for them and what they wanted to improve. As we went from neighbourhood to neighbourhood—first to St. Louis and then to Detroit—we realized that we had an opportunity to improve and strengthen the fabric of the community behind all these sellers.

One of the things I remember growing up was the power of the neighbourhood in terms of the support and mentorship it provided, and that’s one of the things we’ve lost as the country has grown—at least I think that’s the case in the U.S. I always bring that back to sellers. They can always reach back and talk to people in their neighbourhood; they can talk to one another about best practices, what has worked for them in terms of attracting customers, or keeping the ones they already have.

I hope by providing the venue and getting the merchants together that they take it from there by continuing to talk to one another and continuing to share best practices.

Why did you bring the series to Toronto?

The interesting thing about Toronto is that 98% of its businesses are small, so it’s a huge small business economy. That’s something we want to support. Toronto [has a high number of] local businesses really biting to grow—and we’ll do anything we can to amplify that and shine a spotlight on it.

During an interview with Founders Circle Capital’s Chris Albinson at AccelerateTO, you cited a New York Times report that the number of independent coffee shops in New York now outnumbers the number of Starbucks and Dunkin Donuts locations combined. What’s driving that trend?

I think there are a number of things happening.

First, it’s never been easier to start a business. We have all these great tools and technologies, and people are going out with the confidence to do something that they’re really excited about. It’s infectious, because when you go into these places, you realize, “Wait a minute, I can do this, too.”

I also think technology puts more of a spotlight on these folks. Twitter and Foursquare have unlocked the city, in terms of the people that are around you—they’re cool, they have a great aesthetic and they really show it off. What we’ve done with Square Wallet and Square Market has that same effect—you can see all these great merchants around you.

Generally, I think people want more diversity, they want something that is obviously crafted—not just something that’s manufactured—and there is this flight globally towards quality, which we’re seeing and want to support.

On stage at AccelerateTO, you said: “One of the things that we believe at Square—and this is something we’ve tried to live—is that entrepreneurship doesn’t necessarily mean you’re starting a company. Instead, it means that you’re willing to take a significant risk in order to see something in the world, and you can do that by building a company, working for one, working for an organization or even through a government.”

It seems like you have a definition of entrepreneurship that is really inclusive. What has informed that definition?

I think that terms “entrepreneurship” and “founder” are overused, especially in Silicon Valley. If you really look at the meaning of those words, it has nothing to do with starting an organization or company; instead, they have everything to do with having the confidence to take a risk and bring something new into the world. I’ve seen people do that on weekly basis at the companies I’ve worked at and built, and it happens regularly in governments and organizations.

A lot of that has to do with our concept of founders, which places a lot of emphasis on the founding moment, but ignores the reality that there are going to be multiple founding moments for any truly great organization, movement or government. That’s the biggest issue I have with how a lot of people see entrepreneurship.

In the U.S., we had a group of founding fathers who had all these ideas, but their one great idea was expressed in this phrase, “a more perfect Union.” They knew they weren’t going to get it all right immediately, and that there were going to be people that would come later with better answers—because the circumstances had changed, because the country needed to change—and that those people were going to help reshape the country.

I think you see that in the best companies as well; that’s the only way to build something that is timeless and outlives any one particular individual.

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