VC Fred Wilson says Uber’s ‘ruthless execution’ and ‘swagger’ are key to its success

Speaking on stage at LeWeb 2014 in Paris, Fred Wilson, a partner at Union Square Ventures, said that controversies surrounding Uber aren’t surprising because they are the result of the same attitude that has driven the company to a $40 billion valuation.

“When I think about Uber as a company, I think about an incredible, almost ruthless execution combined with a swagger that is almost unlike anything I’ve seen,” Wilson said. “Early on, they took the approach they were going to beg for forgiveness rather than ask for permission. And that’s the best approach if you’re an entrepreneur.”

Wilson’s firm has invested in two Uber competitors: Hailo and Sidecar. But he said Uber has catapulted ahead because its aggressive strategy means the company hasn’t been afraid to push into markets even if it ruffles some regulatory feathers, or triggers a backlash from traditional transportation companies.

Still, Wilson said that as Uber enters its next phase, it needs to find a way to grow up a bit and recognize that the downsides to its strategy are too great.

“At some point, that strategy stops working,” he said. “If they’re going to be a big, global company, they need to figure out a way to work with the system, and not just say, ‘Screw the system.'”

“I do think they need to figure out how to become a more mature company that doesn’t necessarily have the negative side effects,” he added.

To a degree, Uber chief executive Travis Kalanick, seems to agree. In a blog post announcing the company’s recent $1.2 billion round of funding, Kalanick wrote that Uber is taking a look at its culture.

“This kind of growth has also come with significant growing pains,” he wrote. “The events of the recent weeks have shown us that we also need to invest in internal growth and change. Acknowledging mistakes and learning from them are the first steps.”

Wilson also said it appears Uber is on its way to becoming the dominant company in the mobile transportation market. But he said there should also be room for other players to succeed in the same space.

In response to another question, Wilson noted that he had a chance to invest in Uber and passed.

“These are the things that hurt,” he said.