Uber made its early investors billions. But some had a chance to invest early — and missed an incredible opportunity.

The book Super Pumped details how some investors won the Uber deal, and how others missed out. This fascinating tale of one of the decade’s best startups taught me a lot as an investor.

Sequoia’s Miss

Sequoia Capital, long considered the finest venture firm in the world, passed on Uber repeatedly.

We don’t know why they didn’t invest. But I suspect they were concerned about Uber running afoul of taxi regulations.

However, the initial product was entirely legal. UberCab was simply software to order a black car.

In the past, you did it with a phone call. Now, you clicked a button. Either way, it’s legal.

For a firm betting on early stage moonshots, Sequoia was too cautious.

Skate to Where the Puck Is Going to Be

“I skate to where the puck is going to be, not where it has been.”

Wayne Gretzky

When UberCab launched, it was a rather unattractive desktop app, not the slick mobile platform it is today.

But early investors like Jason Calacanis saw past that.

They knew Travis’ vision was to be able to get a car anytime, anywhere using your phone. Their bet was that he could do it — and the bet paid off.

When Uber was founded in 2009, smartphones weren’t yet widespread. The iPhone was just two years old.

But a good investor can spot a trend. And iPhone sales were skyrocketing.

Soon, there’d be one in every pocket. If that iPhone had the Uber app on it, Uber would make billions.

The Best Deals Don’t Come Easy

Other than the first few angels, every investor had to fight to get into Uber. Bill Gurley and Travis Kalanick made the Uber deal in a San Francisco bar on a Sunday night.

You have to chase the best deals, even in your off hours.

That’s why I found myself in a quiet corner of a hotel lobby in Barcelona one night in 2021.

It was almost midnight local time. But this was a deal I couldn’t miss.

The meeting went great and I made the investment.

Today, that company, Deft, has created one of the most exciting multimodal search engines in the world. They just got featured in TechCrunch!

What to Look For

Above all, what made Uber was Travis’ tenacity.

If an investor asked him about his prior experience as an entrepreneur, they’d find out he sold Cutco knives door to door. They’d also learn that his first startup got him sued for $250 billion.

And still, he kept going.

A founder that dogged attacking a huge problem is a great bet.

I find myself looking for the same things Gurley does: strong traction in a giant market. And if the startup takes advantage of a huge platform shift, like AI today, that’s chef’s kiss.

Wrap-Up

For an angel like me, Uber would be the ultimate score. All day, every day, all I try to do is find one.

Super Pumped shows me how important it is to back gritty founders. And they don’t come grittier than Travis.

Uber also taught me to accept some risks, like regulatory issues, if the upside is big enough.

What did you learn from Travis? Leave a comment and let us know!

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More on tech:

Super Pumped (Part One)

Super Pumped (Part Two): The Rise and Fall of Travis

WeWork’s Bankruptcy: A New Beginning?

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