Lessons in Bravado from a Rock Star Entrepreneur

You've got a great business idea. Now what? Follow Square founder Jack Dorsey's lead: don't fear failure

Written by Mira Shenker

Jack Dorsey knows how to answer the toughest question a tech startup—or really, any startup—will be asked: if it’s such a great idea, why couldn’t one of the big guys do it?

The founder of Square (and co-founder of Twitter) is a rock star as far as the 800 or so delegates at yesterday’s AccelerateTO were concerned. Organized by non-profit The C100, the one-day event featured founder of Kobo Mike Serbinis and president of the Treasury Board Tony Clement, plus two pitches from promising startups Bionym and Finmaven. But the crowd was clearly most excited about seeing @Jack. “Waiting for @jack to make his appearance at #accelerateTO feels almost like waiting at a rock concert for the band to come out,” tweeted @MarioCantin.

At the end of the day, Dorsey is just a programmer with cool boots. But this crowd idolizes him because he saw a need, built the solution, then took the risks necessary to make a commercial success of it.

There’s nothing wrong with salespeople, but you’ve got to have something to sell.

It’s not easy, and it’s perhaps harder for Canadians, who are more afraid of failure than their American counterparts. According to Ernst & Young’s G20 Entrepreneurship Barometer, 35% of Canadian entrepreneurs see failure as a barrier to future business prospects, compared to only 20% in the U.S. (Read the full story: The Weakness That’s Hurting Canada’s Entrepreneurs.)

Canadians also lack some of the bravado that has helped Dorsey sell his ideas. It’s one of the reasons that, as PROFIT columnist Chandra Clarke says, Canadians suck at marketing. Dorsey acknowledges that failure is a very real possibility; he doesn’t hide from it, not even when potential investors ask that tough question.

Dorsey told the crowd about a meeting he took with an investor while trying to launch point-of-sale tool Square. He showed two slides: one listing the many reasons his venture could fail—including the possibility that Google would come up with its own version—and another listing all the reasons it would succeed.

It sounds obvious, but many entrepreneurs haven’t thought about why they could—and probably will—fail. They’ve only thought about how great their product or service is going to be.

Dorsey readily admits that he’s made mistakes. In the early days of Twitter, they hired a slew of salespeople before they even had a solid product to offer. “There’s nothing wrong with salespeople,” he clarified for the crowd, “but you’ve got to have something to sell.” What they really needed at the time were more programmers.

Some of his success despite these missteps has been sheer serendipity. But he survives due, in part, to his willingness to pursue his business ideas wholeheartedly, even while they’re still percolating. When Dorsey took that meeting for Square, the product was still called Squirrel, an early iteration that they designed the entire venture around, down to the acorn-shaped reader. He changed his mind during the meeting when he realized Canadian company Squirrel Systems already existed.

This was Dorsey’s first trip to Toronto—but it will likely not be his last. He announced yesterday that Square would be opening an office in the Kitchener-Waterloo area. It already has a temporary workspace set up in the Breithaupt Block in Kitchener. This permanent space will employ 30 engineers. I don’t doubt that there will be a line of eager grads looking to work with the programmer-turned-CEO who compared open source to punk rock.

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