They might think Uber or Zipcar will be the big winners in this space, but as you can see from the performance of those two companies, they are two very different concepts. In the first solution, you are driven door to door, but in the second you take possession of a car for a short period and drive—and park—yourself. The latter is a closer analogy

There are some investors who feel it’s the market that makes the startup. They will look at the size of the insurance, food, or transportation industries and say, “Technology is going to massively impact these industries—let’s find startups who are innovating in this market.”

In another five to ten years, things will change again, and the only way to understand where the market is going will be to study not just the market winners but the market failures—along with doing a postmortem on your own forecasting and behavior. You don’t have to obsess over the losers, but I would certainly meditate on them and look for patter

There are some really, really bad answers to the question “Why are you doing this?” The worst two answers, which you’ll hear often, are “To make money” and “Because INSERT-SUCCESSFUL-COMPANY-NAME-HERE doesn’t do it.”

Those founders don’t need you, they don’t need your money, and they are not going to meet with you. You need to find founders who will become the next Mark Pincus and Evan Williams. The only way you’ll get into a hot deal early on is if you are invited into one or you get lucky. When you first start investing, you should meet with as many people as

I try to choose companies based on the people running them, not the idea or market, because I’ve learned that no one can tell the future but I am an exceptional judge of talent. “I don’t need to know if your idea is going to succeed, I need to know if you are,” is a line from my blog that has been repeated over and over again.

Year two sucks, but the later years of angel investing—specifically years three to seven—tend to be filled with good and sometimes great news.

I’m famous for having invested $25,000 in Uber when it was worth around $5 million—it’s now worth $70 billion in the private markets. When I invested, Uber was operating in one city and they only had a couple of Lincoln Town Cars signed up. It wasn’t clear if the business could scale or make money, but I knew the founder was exceptionally driven an

The world is becoming controlled by the few, powerful, and clever people who know how to create those robots, or how to design the software and the tablet on which you’re reading this. But please don’t stop reading, because I’m going to show you how anyone can get a seat at the table with the digerati, illuminati, and moneyrati and, perhaps, tap in