36 Things I’ve Learned During My First Three Months Investing

Here is a short and blunt list of things that I’ve learned transitioning from a founder of a startup to an investor in startups:

1. Invest in amazing people. They will find a way.
2. Make predictions and try to spot emerging trends. Then, find amazing people working in those areas and give them whatever they need.
3. Move quickly. It can be a valuable asset as a new investor.
4. Make introductions. Try to be that person that connects everyone- the more you do this, the more people tend to gravitate and stay close to you.
5. Your portfolio is a representation of who you are as an investor and person. Invest in the best.
6. Try to align yourself with larger funds and experienced investors. Send them deal flow. Give them candid thoughts on deals. But don’t waste their time- curated and relevant deal flow is key.
7. Meet with as many people as possible. Don’t assume that just because a meeting doesn’t have a specific purpose that it isn’t worth your time.
8. When you do meet with people, always buy coffee, drinks, lunch, breakfast, etc. $60 on a few drinks (I live in NYC) have long term benefits.
9. Look out for other people. Karma is big in VC.
10. Establish a focus. Be the best at that space- and then dominate. I try to focus on millenial focused startups with a community aspect. Try to become that expert that other investors value your opinion in.
11. Admit it when you don’t know something.
12. Provide your startups with more than just capital.
13. Understand that all founders are different- and so is the way that they communicate with investors. You have to adapt to them, not the other way around.
14. Introduce your portfolio companies to one another. Social Starts did a great job at that while I was at Sumpto.
15. Randomly ask your portoflio companies specific ways that you can help. Although random, I think (hope) they like it as it shows I’m constantly thinking about them.
16. Ask for second opinions on new investments.
17. Trust your gut.
18. Be willing to invest in a founder after one meeting.
19. Don’t lead a founder on. Don’t waste their time.
20. One of the coolest things a portfolio company can say about you is when they are describing you to someone else “XYZ is an awesome person, they’ve been a huge help to us, they introduced us to big client XYZ and they also invested in us early”. That screams value-add when ‘investing’ comes at the end of a description.
21. Be honest with your portfolio companies. Call bullshit. Don’t sugar coat things. Don’t waste your time with skirting around the issue. You’ll only be hurting them. If you think that you may hurt their feelings, just say ‘Hey, I’m going to be 100% honest here. Take this with a huge grain of salt, I’m neither wrong nor right but….’
22. Respond quickly.
23. Leverage your strengths differently in each of your investments. The sooner you understand how you specifically can help each portfolio company, the better your relationship will be with each company.
24. Read. A lot.
25. Learn from the best- read blog posts from people like Mark Suster and Fred Wilson.
26. Ask people for help.
27. Provide people with help when they ask. Go above and beyond on this.
28. Try to keep in touch with amazing people. I reach out to Ben Lerer every few weeks and give him an update. Does he ask for it? No. But the guy is a legend and I want to keep him updated.
29. Keep people updated with what you are doing, thinking, seeing, observing, debating, etc.
30. Keep it casual.
31. Find mentors. I don’t think this is an apprentice industry (although a lot of people do and I’m coming from a different angle) but it does help a lot to learn from more experienced investors.
32. Differentiation as an investor is key.
33. If you can, leverage your age as a strength.
34. Inexperience can be a strength. Understand it.
35. Recent startup experience helps.
36. Invest in amazing people. They will find a way.