One of the greatest mistakes of my investing career was passing on investing in Uber in the angel round — twice! Because if I had written a $50,000 check (for Uber), like I normally did at that point in my life, it would be worth hundreds of millions today.

But I had bought my first significant apartment in Manhattan weeks before Uber came across my desk. I was not sitting with the kind of liquid that made me feel comfortable. Don’t forget, I’m an immigrant. You’ve always got to have a little bit of cash under the bed, right?

Uber co-founder Travis Kalanick came and said, “We’d love for you to invest.”

And then Travis decided to run the company. This is somebody I unbelievably believed in. I knew him personally. I was growing up in Web 2.0. We were investing and speaking at conferences together. He had a prior startup in the Napster space, so he was a technologist for a long time at that point. He was ambitious, hungry, and smart.

I was literally in the room when Uber was invented, and yet I still passed on investing in the angel round… Twice.

BUT part of the reason I invested in the next round was because my brother AJ took the first Uber ride in New York City when the founder of Uber came and asked us to test it.

And that was the moment I realized, Uber doesn't sell transportation. Uber sells us time. The reason all this infrastructure matters in an app environment is because it's just seamless, there's less friction.

The number one emerging thing in society in value is time: people value time over everything, which is why convenience and lack of friction win.