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What happened when VC Fred Wilson met Uber's Travis Kalanick: 'We just didn't like each other'

  • Union Square Ventures investor Fred Wilson had harsh words for Uber on stage at the Techonomy NYC conference.
  • He criticized CEO Travis Kalanick's "win at all costs" strategy and says it "didn't actually work."
  • But he acknowledged that one big insight at Uber, that the economy is shifting toward more gig-based freelance work, is right.

Venture capitalist Fred Wilson said he met with Uber boss Travis Kalanick about investing in the ride-hailing company — but it didn't go well.

"We didn't like each other," Wilson said Wednesday at the Techonomy NYC conference.

Wilson is a partner at Union Square Ventures, an early investor in internet companies like Stripe, Twilio, LendingClub, Etsy, Tumblr, Twitter and Indeed.

Co-founder of Union Square Ventures Fred Wilson
Getty Images
Co-founder of Union Square Ventures Fred Wilson

Uber has been under pressure amid an internal investigation into sexism claims, a trade secret dispute with Alphabet and allegations that the company evaded regulators. Wilson said Uber's "win-at-all-costs" strategy assumed that drivers and consumers would be loyal — rather than adopting multiple platforms to compare prices.

"I think Uber had a strategy that didn't actually work, which was that they were going to run the table on the ride-sharing industry, and they were going to put everybody out of business by raising more money than anybody else," Wilson said. "They thought that they were going to do in ride-sharing what Google has done in search ... and it just didn't work."

Uber's valuation, though, has exploded — it was valued at over $68 billion in its last funding round, according to reports. Union Square Ventures invested in Sidecar Technologies, acquired by General Motors, which collaborates with Uber's rival, Lyft.

But Wilson said because the Kalanick tightly controlled the way the company was financed, most of the money from Uber's business is "only on paper."

"No one has made any money in reality," Wilson said. "Everything that's gone wrong is a function of their strategy to control everything and go very aggressively."

Uber did not immediately respond to CNBC's request for comment.

Uber has championed one trend that Wilson is watching, the so-called gig economy where full-time employment is less and less common. He referenced his favorite lyric from rapper Jay Z: "I'm not a businessman, I'm a business, man."

"That's the future," Wilson said. "If you're measuring the number of companies that are being created or the number of full-time jobs in the economy, you might be measuring the wrong thing."

Wilson noted that trends among young people, like not owning cars, have brought down the cost of living, making it possible for new graduates to take more risks.

"I'm not suggesting that everybody's going to be an entrepreneur," Wilson said. "The age of being able to go find a job and feel secure? I think that's gone. But you can have a job and not have to be an entrepreneur."

Still, Wilson noted, freelancers and entrepreneurs face challenges, including getting affordable health care — since the American health care system relies heavily on employers.

"The only place, possibly, that is more innovative than the United States is China, and there, you do have a government that's probably more interested in amplifying this than here in the U.S. But other than that I think we are doing OK," Wilson said.