Thread by @blader

1/ This is the sad story of how I didn’t invest in $UBER after seeing it prelaunch. Or: why early stage investing is hard. Or: why I’m an investing idiot. Thread 👇:

2/ About 9 years ago, I was out with @kamalravikant for drinks at the St. Regis in SF. He starts telling me about this magical app that can summon a luxurious chauffeured black car to pick anybody up, and drop them off wherever you want. He called it: Ubercab.

3/ He does a live demo of it, and it was like magic: press a button, and you get a chauffeur. The primary use case at the time seemed to be for rich people to impress their dates. It seemed like a niche market but I was intrigued.

4/ I had just started angel investing, and got super lucky with my first investment (thanks @flashsoftteam) and I was on the lookout for new deal flow. So as I was sitting there with Kamal, I install it on my iPhone 3GS to try out the app.

5/ Signup goes smoothly. Then I try to enter my credit card number, and I get “internal server error”. I try a few times, same thing. Well that was enough for me - “these guys are idiots, they won’t even let me pay them.” So right there I wrote them off.

6/ Fast forward a few months later and I was using Uber daily to commute to work. Fast forward years later, here we are today. Congratulations to everyone at Uber for building an amazing company, and I would like to apologize to my family. FML.

7/ One of the best pieces of advice I ever got was from @markpinc of Zynga: “It’s easy to imagine what could go wrong, I like to imagine what happens if everything goes right.”

That’s the most important question I now ask myself when evaluating a new investment.