Twitter’s Jack Dorsey wants Square to be hip

It was probably not the kind of advice students at the University of Waterloo were expecting to hear from the co-founder of Twitter. “Don’t be late. Don’t interrupt. Don’t send so much e-mail. Stand up straight. Say hello to as many people as possible. Don’t have hard liquor during weekdays.”

These are some of the items from the “Dos and Don’ts” list that Jack Dorsey keeps stored on his phone and available at all times. This practice, he told students during a speech on Thursday, could be as important a tool for them to use as anything they’ll find online.

“It will bring you significant focus, so you can iterate and do whatever you want,” he said. “You can build companies around it, build organizations around it, so the organization has a clear sense of what it’s doing and what it’s not doing.”

Establishing such clarity is important for Dorsey because, unlike the Mark Zuckerbergs of the world, he is in the awkward position of being famous for one thing while trying to become more successful with something else. Every introduction, and most of the media coverage surrounding him, is focused on his origins with Twitter, especially after recent news of its possible IPO. However it is Square, the startup he founded a few years ago to enable financial transactions in a more seamless manner, that has become his true day job.

This must be what it was like for Steve Jobs (to whom Dorsey’s visionary sensibility is most often compared) when he had left Apple and went on to found NeXT, a startup that never came close to capturing as much of the public’s imagination. The difference here is that Dorsey is still running both companies, and can leverage the interest in Twitter to create opportunities to discuss Square, and try to make it sound sexier than it is.

“We are not a payments company,” he told the audience in Waterloo, which he was visiting in part to open Square’s first Canadian office. “We are a commerce company. Payment is just one tiny little piece of that. This is a conversation.”

By that Dorsey means that Square will make buying things not only easier and more intuitive, but social. You’ll walk into a store and wireless networks will identify you based on your phone or tablet and simply charge things to your credit card, leaving those at the coffee shop with little to do but verify your details and smile a friendly greeting.

“We’re giving time back to people,” he said. A favourite example is being at a restaurant with his best friend or a girlfriend and wanting to leave to catch a movie or a concert and frantically trying to wave down the waitress for the bill. Another analogy is that a service like Square is like the San Francisco bridge. “A bridge is there to get people from point A to point B and not fall down.” A great commerce platform should do the same thing.

Yet even the best commerce platform -- and Square may be that -- produces nothing except the transfer of money and products or services. It’s not writing a funny Tweet, or retweeting a link to an incredible video, or talking directly to a famous person over Twitter. Commerce by itself does not allow for new modes of expression or even necessarily lasting connection.

Square’s audience is also more niche than Twitter’s. It may enable commerce for consumers but its big target is small entrepreneurs who have difficulty processing payments. It’s a startup for other startups, and Dorsey’s biggest challenge in marketing Square and attracting the bright minds at places like Waterloo is selling the idea of an organization whose most lofty goal is to replace the traditional cash register.

“Everyone in our company is a designer,” he said. And I bet that when they finish using Square to pay for something, one of the first things they do is take out their smartphone and check Twitter.