When things just don't feel right

I’m on day 10 of this cold. The fatigue is nearly gone, but this cough does not want to go away. This should serve as a reminder that I now need to take it easy when I’m starting to feel sick. Taking a day or two off to rest and recover fully beats being a shell of myself for a week and a half.

One big lesson that I’ve learned at Secfi and investing over my 5 years is that you just need to trust your gut when things don’t seem right.

Early on during my time at Secfi, I was much more hesitant to bring “yellow flags” up for fear of being wrong. At that point, I convinced myself that I was new to this game of investing and that’s just how things were.

Sometimes it would be a odd signal that a bunch of executives were looking to sell out quickly. Or sometimes it would be a group of key engineers on what seemed to be a rocketship looking to leave early and leave a bunch of unvested options on the table.

Of course these are just signals and doesn’t mean necessarily mean the company was in bad shape. But I often found that these yellow flags would add up. Often when that happened, the company almost always turned out to be a bad investment.

Nowadays, it’s pretty obvious when things aren’t going well at a company for me. I can usually tell within the first 10 minutes if the executive or employee believes in the company in the long-term. When things just don’t feel right, we make sure to pass fairly quickly.