14 Lessons Learned from Year #1 as a Startup Investor

Lessons I’ve learned investing so far:

1) FOMO is real. You have to make a conscious effort to not let it affect your thinking and maintain your own intellectual independence.

2) Investing downstream of YC at Demo day is both awesome and terrible. Awesome because the companies are amazing. Terrible because you have no time to decide and the entire dynamic encourages you to be viewed basically as a commodity.

3) If it doesn’t feel right, don’t do it. For me personally, I often have accurate gut feelings that I am not able to articulate until later. I am getting better at articulating the source of my feelings faster, but not in real time.

4) Be decisive. If I’m on the fence, just pass. Don’t string yourself or the entrepreneur along.

5) The best entrepreneurs learn really effing fast and will get better before your eyes. If something doesn’t feel right, ask yourself “is this founder learning fast?” If the answer is no, pass.

6) Have a clear investment thesis and criteria. This makes life soooo much easier for you and the entrepreneurs. It took me a while to get here, but now I have a simple pitch: I invest in outsiders doing crazy shit that, if it works, will solve an important social problem. Awesome people is #1. World changing is #2. Crazy is #3 and something I’m willing to flex on, whereas #1 and #2 are “must haves.”

7) Life is easier when you commit to saying what you actually believe, even if the message hurts. I still always try to be kind, but now that I’ve committed to being truly honest, I feel better and freer. It’s great!

8) Slow down. Have a process. This helps build deep rather than shallow conviction.

9) Investing is about feelings. How does the company make you feel in your gut? Listen to that feeling. Numbers matter, but it’s all fucking guesswork and no one really know. While there is value in fundamental analysis, there’s no value in false precision.

10) Truth > fact. Facts you can prove. But there’s a lot that is true that is not provable.

11) My best decisions come from when I listen to my gut.

12) Leave everything on the field. Act with decisiveness, passion and conviction. Hold nothing back. Regret nothing.

14) Don’t doubt yourself. Fight for what you believe, even when other people think you’re wrong or stupid. Just because you might sound stupid doesn’t mean you’re wrong.

Also published on Medium.