Real. Honest. Fear

“I don’t know what I’m doing”

How many times has a founder told that to a board or to his management team?

Rarely, if ever.

How often does a founder feel that way?


(Related: How often does a VC tell his partners that statement? Rarely, if ever, unfortunately.)

The reason why a founder won’t open up and share that fear is because of another fear: the fear of looking weak or clueless. “If I share my fears, I could lose my job or lose control”. 

One way I know I’ve really connected with a founder in our portfolio is when they let me in on their true fears. Not fears about the competition, or fear of not being able to hire the star developer they have been targeting, or fear of missing the revenue target for the quarter. But the real, deep, honest fear: “I don’t know what I’m doing”

It doesn’t always happen even though I can feel it. And that’s fine. Not everyone feels comfortable sharing things with me. But the ones that do share that true honest fear are the ones that I can help the best and the ones I can connect with at a deep level. It’s one of the best parts about this job of mine. 

One useful exercise when a founder evaluates his/her investor should be: “what if I tell that VC my real fears? Will he/she help? Or attack? ”

When I started out as a VC, seven years ago, I really didn’t know what I was doing even though I was beyond ambitious. 

I had confidence on the outside. Yet there were plenty of days when I felt like I was unsure & uncertain. Am I going to be any good at this. What if I’m not?

My partners were extremely supportive and in fact, I led our very first investment after we raised our first fund. I needed & received help from the experienced members of the partnership to do the proper due diligence on the company and think through if the investment was the best for our firm.

We ended up making 3x our money in 6 months. Not bad for a first time VC. But guess what. My next investment failed. It wasn’t a huge investment but it failed completely. 

One moment I felt pretty good about myself and the next: Oy. Ouch. It feels awful because fear can creep back in. It happens so easily.  

Fear is a powerful thing.

Sometimes it brings out the best. I suppose it’s when we deal with it honestly. And in plain sight. With people we trust. People that can help us get our perspective back.  

Sometimes it brings out the worst. I find with me and others I know, it brings out the worst when we haven’t fully faced our fears. Instead we cover them up by blaming others or hiding them away in some deep dark safe place.

The thing I’ll end this post with to all the founders that might be reading this is: you are not alone. We are all working through it. It’s ain’t easy and it’s isn’t a one time affair with a quick fix. Surround yourself you truly trust and let them help. Even if it’s just to air it out and let it fly.