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A CEO who sold his company for $365 million offers some of his best business advice: Take fewer risks

David Rusenko CEO Founder of Weebly

  • Weebly CEO David Rusenko recently sold his company to Square for $365 million.
  • Now, Rusenko is offering advice to other entrepreneurs: Take fewer risks.
  • Rusenko says entrepreneurs aren't so much risk takers as they are eternal optimists. 

"I think I am demonstrably not a risk taker," says David Rusenko, CEO of website software company Weebly. "Anyone who has worked with me would back me up on that."

Rusenko, who sold his company to Square earlier this year for $365 million, says there's one enduring mythology about entrepreneurs that he'd like to set straight: Entrepreneurs, it's largely held, are risk takers.

But according to Rusenko, this is a mischaracterization that's not only inaccurate — it's also damaging. 

"Taking risks is important," says Rusenko, "but people's conception of entrepreneurship as this inappropriate, cavalier risk-taking is draining."

Rusenko cautions that entrepreneurs should take as few risks as possible. Rusenko speaks from experience: He's spent more than 10 years working on his San Francisco-based company. Along the way, there's been plenty of ups and downs. For Rusenko, being a successful entrepreneur is less about hair-trigger decision making, and more about diligence, persistence, and patience. 

"I take as few risks as possible," says Rusenko. "It's more about having conviction in what you're doing. It's about seeing a need in the marketing and going out and building it. People along the way will tell you that it won't work, that it won't be successful, that the market doesn't need this. If you have the evidence, you have to continue to believe in your company."

Entrepreneurs aren't so much risk takers as they are eternal optimists, says Rusenko: "Entrepreneurs don't see risks where other people see risks. They're optimists."

Of course, there's some risk-taking involved, says Rusenko, but less than you might think. Appropriate risks are calculated risks, Rusenko says. 

"The risks are principled," says Rusenko. "But it's more about the optimism to believe that what you're doing is going to work."

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