Sublime

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.

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.

I ask founders to explain to me every word I’ve never heard of, be it a company or technology or theory. This helps me in three ways. First, I get points for being considerate. Second, I get to hear how well they can explain things. And third, I get smarter. When I meet with founders, they are frequently awed by my knowledge of their business, and

As you go through your angel investing life, take some time to evaluate the person and their motivations. Ask yourself a simple question: “Would I buy stock in this person if I could?” If you wouldn’t buy stock in a founder, you shouldn’t buy stock in their company—because there is no difference between the founder and their company; they are one

If you’re getting into a Series A alongside a powerful VC, you either have a great relationship with the founders, who are demanding you get an allocation, or you provide massive value and the VC thinks that you owning shares in their company will increase everyone’s share value. If one of your startups, that you’ve angel invested in, gets a Series

I’m going to take you through the four most important questions I ask all founders. The goal of asking these questions is not just for you to understand the business but also so you yourself can answer four critical investor questions: Why has this founder chosen this business? How committed is this founder? What are this founder’s chances of