Weebly CEO David Rusenko offers some of his best business advice: Take fewer risks

David Rusenko

• 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. 

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“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.”