I just couldn’t relent. In my younger days, I had a horrible habit—back to those habits—of needing to explain to stupid people just how stupid they were. I’ve since learned that the best way to deal with stupid people is not to have them anywhere near your company and, if possible, not even in your life!

Meetings are important and free. You should take a lot of them. Ten one-hour meetings a week is a good target for a professional angel. Half that if you’re doing this part-time.

The big problem with “founders” who build a feature that a market leader will inevitably get to—and I use quotes here for a reason—is that they lack vision. The act of selecting a feature as their life’s work, as opposed to a full-blown product or a mission, disqualifies them from being a true founder.

A startup that has either (a) six months of continuous user growth or (b) six months of revenue A startup that has notable investors A startup that, post-funding, will have eighteen months of cash remaining, commonly referred to as runway (ask the founder and syndicate lead how many months of runway they will have post-funding)

The best you can do in these cases is privately support the heck out of the founders and their management teams and help them resolve their challenges. Never engage the press—unless the founders themselves ask you to. If you see me commenting publicly on an investment of mine, you can be sure that it’s with the blessing of the company. Other

Pro rata rights are a must and you should never do a deal without them. Most founders will give their angel investors pro rata rights. If they don’t, something is off. Why wouldn’t you want your early investors to get rewarded? If a founder has been convinced not to give pro rata, or says you’re too small of an investor to deserve it, I suggest

Folks in the technology industry debate if angel investing is gambling or actual investing, and it depends largely on how you approach it. Every year I place forty bets hoping to win back more in aggregate than I’ve put down.

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).

The businesses that angels invest in are typically less than three years old, have little or no “traction,” and are trying to find something we call product/market fit. If these businesses didn’t look completely crazy, then everyone would want to invest in them and there would be no need for angels. In fact, the term “angel” is used because we are