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

In month two, you are going to meet with twenty-five founders. You’re going to listen to their pitches and ask lots of short questions and write long notes about their answers. When they ask you if you’re in, you’re going to tell them that you need some time to come to a decision. Again, never say yes in a meeting. Let them know that you need to do

You should dedicate a full hour for your in-person meetings. This signals to a founder that you take them seriously enough to spend time understanding their business. These days, not only do I take a full hour for a meeting, I leave thirty minutes open after it just in case they keep going. I let founders talk and talk until they are tired of talki

If you’re going to meet with a founder, you need to do some research on them. This includes reviewing their product, understanding the market they operate in, knowing who their competitors are, and knowing who else has already invested in the company. Some of this information is freely available, some of it is in their deck, and sometimes it doesn’

These days, I am most likely to tell founders “not yet” when they ask me if I’m ready to invest. It’s an elegant phrase that Roelof Botha taught me and it works like a charm. In addition to telling them that I’m just not there yet, I let them know that I’d like for them to add me to their monthly updates.

Additionally, remember that 80 or 90 percent of our investments fail, and we have to suffer through shutdown after shutdown. It’s depressing for us, especially in years two, three, and four of angel investing (see chapters 28 and 29).

If you’re exhausted from angel investing but you are addicted to startups, you’ll have a nice track record with founders that will allow you to join a venture capital firm with a $500,000 starting salary, making this a fantastic investment similar to getting your undergrad and graduate degrees!

Most of us don’t have three or four decades to build our fortunes. We want to do it in five to ten years, which I think is a reasonable window if you read this book and do what I tell you. If you compare businesses made from atoms (brick-and-mortar shops like Starbucks and McDonald’s) to businesses made from bits (software), there is no comparison.

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.

There are personal questions you can ask founders to get a sense of what they’re about. The one I care about most is, “What did your parents do?” I used to ask, “Tell me about your mom and dad,” but that’s a bit of a biased question since some folks grow up with two moms or two dads or a single parent, so the best way to do this is to ask about the

Everyone wants to be a founder, but they don’t understand exactly what that means. Being the leader sucks because you’re ultimately responsible not only for your performance but also for the performance of your entire team, the market, your investors, your competitors, and even your customers. Most people calling themselves founders today are just