What keeps me up at night

What keeps you up at night?

One of my favorite questions asked on almost all our due diligence calls we have with companies. We used to ask it quite a bit back in my consulting days as well.

It came up on a big diligence call we had earlier this week and I thought about how I would answer it if an investor asked me that question.

Truth is that a lot of things keep me up at night. Husky football woes. Hunger. FOMO on stocks that I didn’t buy. But when it comes to Secfi, it’s a really good question.

I get a lot of friends who aren’t at startups who ask me if I’m ever worried that we’ll fail. That doesn’t really keep me up at night. I came in with the expectation that joining a startup is risky and that I’d be happy no matter what happened. I know a lot of founders and employees unfortunately do wrestle with that reality quite often.

While I don’t fear failure, what keeps me up at night is letting my team down. The last few times I recall waking up in the middle of night and resisting every urge to open my laptop has been related to worrying if I got something done for someone on the team.

Are they going to be stuck for a day because of me? Are we going to lose the deal because I forgot to do something? When you’re part of a small team, everyone is such an important cog in the machine. There’s seldom someone else on the team that can do what you do. This is the nature of startups and something that every great team player deals with.

I’m okay with failing, but if we go down, I want to be known as a great teammate who gave it his all.