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Gist founder T.A. McCann just completed a successful sale of his startup to RIM. So, why did the Seattle entrepreneur spend a chunk of his time at the University of Washington business plan competition’s annual awards dinner talking about failure?

Well, for one, it is an extremely important part of the startup process.

“To be an entrepreneur takes a tremendous amount of courage, and it takes a tremendous amount of courage to continue to dust yourself off when you fail,” McCann told the room of more than 200 students, judges and UW faculty. “And failure happens in every entrepreneurial company, even the most successful ones almost on a daily basis.”

Here’s the first half of McCann’s talk:

To illustrate the importance of failure, McCann masterfully weaved in another one of his passions: sailing. He showed a video of a $5 million racing sailboat which broke in half, and sunk in a matter of seconds. Obviously, a big time failure.

He also noted how building a startup and sailing around the world — something he accomplished in the 1993 and 1994 — are actually pretty similar. It takes 18 months, requires a decent amount of capital and depends on the person at the helm to constantly test various hypothesis in parallel.

He added: “As sailors and as entrepreneurs, you are trying to create such a sustainable advantage that you could almost give the company to anyone to run it because it is so much better than everything else.”

But there’s another important parallel: Persistence. McCann said that it takes about 10,000 hours of effort to actually become an expert at something, which equates to about 10 years.

“It is going to take a tremendous amount of time,” he said. “You have to be incredibly persistent, and persistent toward a goal that is only yours. A vision that is only yours. A vision where no one can sort of knock you off that goal because you are so passionate about it.”

To help prevent failure, McCann provided several tips. He has some experience in that regard. Until Gist, McCann said that his four other startups (including HelpShare, essentially an early-generation Quora competitor) failed.

“You have to generate a tremendous amount of ideas,” he said. “The more ideas you try, the more ideas you generate, the more often and better you are going to be at seeing the ones that aren’t going to work.”

He added that the best entrepreneurs are generating ideas every minute, constantly testing them and vetting them.

As I was leaving the event, Keith Vernon of Bristlecone Advisors (who each year reads a children’s book to inspire entrepreneurs. This year it was a variation of “The Little Engine That Could”) said that the the UW business school should consider teaching an entire course on failure.

I thought it was a great idea. What do you think?

Here’s the second part of McCann’s talk in which he talks about the importance of building your “tribe.” In McCann’s words, you need to build your “social graph” and work with people who are you friends, noting that it is “absolutely wrong” to separate business and pleasure.

“You really want to be working with people that are your friends. They are your brothers that you can go to war with. Because it is like war. And you want to be able to rely on those kind of people when it is 3 a.m. and everybody’s tired and everybody’s hurting to be able to help you pull through whatever idea you are working on.”

Previously on GeekWire: Clean water startup PotaVida takes top prize at UW business plan competition


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