Venture Investing is like Dating

On the theme of Valentines Day.

Replace “someone/person” with “company/founders", “relationship” with "investment", “date” with "invest".

  • If you have to convince yourself you like someone, you probably don't.

  • You can look for all the key requirements like age or intelligence or height, and you can meet all of them, but if your instinct isn't there, then it just isn't there. And you will never get there.

  • You may really like someone, but if you don't meet your “make or break” requirements, the relationship will eventually fail because the foundation wasn't there to begin with.

  • Once your instinct is there (or not there), you're going to do everything you can to justify it. Confirmation bias all the way, baby!

  • There is a balance between taking a strategic and smart risk on someone, and being absolutely reckless and dumb. But on the other hand, if your bar is too high, you'll literally never date anyone good.

  • As the person on the other side, they shouldn't let you lead them along because you can't decide. Respect goes both ways - they should also be looking for someone who is really excited to be with them and not spend eons deciding if they actually like them or not.

  • There is again a balance to be struck - sometimes you do have to prove yourself maybe because you had previous bad behaviors or they're just a bit more conservative and guarded. But once you have done your best and given it your all - if they're still not convinced, that's okay. Someone else will be.

  • The younger you are, the more likely your dating choices will be instinct-driven and less requirement driven. Because you're young, there's not much to go off of anyways. And you don't have enough life experience to discern if someone has the fundamentals and you also don't know how people will change nor should you expect them to, even if they try to convince you.

  • That being said, age and experience should not be weaponized, especially in this day and age where information is so easy to access for everyone. Being young doesn't mean you will fail, and being old doesn't mean you will succeed. Experience is important and correlated with success but is not causation.

  • Being self aware is very important. Don't lead people on if you don't like them. Cut them loose. Same thing goes the other way - if someone is leading you on, cut them loose. Find someone who has conviction in you and is willing to bet on you and them together.