Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000

Think about angel investing as a decadelong pursuit.

Most angels I meet are salty dogs, broken-down warriors who want to be in the arena but don’t have the stamina and energy to fight anymore. They are backing young gladiators like you because they know you’ve got a better chance than they do to win.

It was at that point I realized that I didn’t need to know if the idea would be successful. I only needed to know if the person would be.

As far as I’m concerned, angel investing is a vocation or a calling. It’s like teaching or being a Jedi. You should take it seriously because your actions can help create massive change in the world.

2. Why are you doing this?

Pro rata rights are a must and you should never do a deal without them.

Third, I set the tone that monthly updates are something I like to see before I give the founder my money. Life is one giant test, and interacting with investors is one of those tests. Seeing a person execute on their plan over time is the best way to decide if you should invest.

When someone tells me they have a founder they want to introduce me to but they’re worried because the person is a wild card, I set that meeting up for the next day. Angel investors are looking for wild cards, because the best founders are typically inflexible and unmanageable, pursuing their visions at the expense of other people’s feelings.

Rule number one if you do a big hit is to keep your head down and not do any conspicuous consumption.