Startup Secret: Break Out of Your Comfort Zone Often

With Twitter and Square under his belt, you could say that startup entrepreneur Jack Dorsey is on fire. He’s also probably not getting a ton of sleep since he’s playing high-profile positions in these two very large, industry-leading startup companies.

Twitter is the microblogging social media platform that helped turn social networking on its head by restricting the number of characters a user could tweet and by allowing asynchronous following.

Asynchronous following was a stark contrast to the friend relationships that MySpace and Facebook made commonplace. With those two slight innovations, Twitter established itself as one of the leading platforms for tracking the real-time conversations of the collective web.

Dorsey was part of the team of Twitter founders back in 2006, along with Biz Stone, Noah Glass and Ev Williams, and served as the company’s original CEO. Now, he’s the company’s executive chairman but still plays an important role as one of the more prominent faces of the company.

As if the disruption Dorsey achieved with Twitter wasn’t enough, he’s now doing the same with his mobile payments company, Square, where he is CEO. He recently successfully inked a major deal with Starbucks, massively increasing the company’s footprint in one fell swoop.

So how does Dorsey, who’s looking very Steve Jobs–like as he helms two innovative companies at the same time (as Jobs did with Apple and Pixar), keep finding new sources for innovation?

He revealed his secret at the Techonomy Detroit conference earlier this month: He rides the bus every day.

The Innovative Power of Serendipity and New Surroundings

When most people strike it big, they isolate themselves further from society. They buy big mansions that they fill with expensive furniture and expensive toys. They also usually move to remote or exclusive neighborhoods and hire a staff to run their house and cater to their every whim.

In short, once you’re rich, it’s easy to cut yourself off from the average Joe. In fact, it’s not only easy, it’s expected.

But Dorsey uses his daily bus ride as a way to stay in touch with reality. He explained his rationale to reporters at the Techonomy Detroit conference, which the Detroit Free Press reported on.

After his speech, Dorsey said that workers who live in suburban neighborhoods and drive to Silicon Valley office parks every day “don’t really see the problems facing a lot of Americans every single day.”

“And I think that’s a real wasted opportunity,” he said. “So I take the bus to work every day and every day I can see what people are using on their phones, what people have to put up with every single day and exactly what people have to go through just to live their lives. That encourages me and gives me a stronger purpose, sense of purpose about what I want to change and how my work might apply to that change.”

And Dorsey’s not the only startup entrepreneur willing to mingle with the people.

Groupon Founder and CEO Andrew Mason recently put himself in merchants’ shoes by serving as a headwaiter for a Japanese restaurant in Chicago. Bloomberg Businessweek profiled Mason’s experiment, and he crystallized why the experiment was important to his role as the leader of a startup company:

“In addition to actually greeting customers as they come in,” says Mason, “I’m running between the front of the house, where we have one system, and the back of the house, where we have another system, entering redundant data from one into the other. I’m just managing the mess that is this technology infrastructure for the business.”

Mason says his hosting gig, which he agreed to discuss on the condition that the establishment not be named, helps him understand what makes local merchants tick—how they book reservations, accept payments, and manage inventory. It’s all the stuff businesses do behind the scenes.

“I didn’t realize how hard it was to run a small business,” he says.

Mason and Dorsey’s experiences have taught them that throwing out proclamations from the ivory tower is no way to innovate. The best way, it appears, is to start from the ground up.