Charles Hudson on why investors miss deals by overthinking. He hesitated two weeks on a founder he liked, assuming no rush since other investors weren't circling. By the time he came back, the deal had closed.
I've had one of those cases where I think maybe from an investor standpoint, I just should have leaned into my gut a lot more and just had conviction areas. I waffled a little bit more on a deal that I was like, I really like this person. I like their idea. Maybe I'll take another week to just make sure I understand the market enough. And at that time that I talked to them, no one was interested. Like, no one really started talking to them. So in my brain, I've got time. And then lo and behold, two weeks later, when I come back, I'm like, love to kick off this diligence process. Like, well, it's done now.