I listened to an investor share the best pieces of advice he’s been given. The one he discussed the most was about choosing whom to work with. His mentor told him life’s too short to work with people you don’t love working with. The investor went on to describe how that piece of advice shaped his selection process across the board (LPs, founders, team members, etc.).
I agree with this investor’s mentor. Life is short. You want to spend time working with people you enjoy working with. One thing that the mentor left out, though, is that working relationships are bidirectional. As much as you may want to work with someone, they must want to work with you, too. The feeling may not be mutual—at first, at least. If you’re in this situation (and lots of people are), work to position yourself in such a way that others will want to work with you. And understand that can take time. Sometimes an interim step is working with people who aren’t your first choice so you can gain credibility to set yourself up to work with your first choice. The important thing is to have a target—to know whom you want to work with—and understand what you need to do for them to want to work with you!