First Time CEO Lessons — Be Fearless

So it’s been a while since my last entry, but that’s cause we’ve been working our butts off while spending our time here at Techstars.

Over the past couple of weeks, we’ve been in get shit done mode. I’m very proud to say that the team has accomplished so much in the past few weeks because we haven’t let a big hurdle get in the way. What’s that hurdle? Fear. Fear of being rejected. Fear of being seen as stupid. Fear of doing the wrong thing.

A lot of entrepreneurs end up not doing anything because of fear. They’re scared that they might do the wrong thing when facing a fork in the road. They’re afraid of the potential outcome that could totally rock their assumptions about the market. In the end, entrepreneurs who are scared just end up kicking the can down the road, staying in their happy little comfort zones, and get absolutely nothing done.

So how do you get out of the space of intention and into the space of realization? Or in other words, how do you get out of planning phase and actually go out there to get shit done.

“Here’s some two by fours, nails, and a hammer. Now go build a bridge to get over yourself.”

I will never forget those words that one of my good friends told me when I told him I was scared of how to move on and what to do. In the end, I had to get over myself. I had to get over my fears. So how did I do that?

I simply asked the following questions:

“What’s the worst thing that can happen if I do X? What’s the worst thing that can happen if I do Y instead? What are the tradeoffs for X to Y?”

I approach every situation in building the company asking those questions. When taking meetings with potential sales, I ask, what’s the worst that can happen if I meet with them?

Literally, the worst thing that can happen is I get told NO. It’s not even a NO that is forever. People can have their minds be changed once they see that other people are using your services (FOMO doesn’t just apply to investors). Rejection isn’t a bad thing. Use it as a learning experience to see where you failed and simply do better next time. Take ample notes and figure out how to better articulate your value proposition.

See? The NO has already been turned into a positive. You’re learning what NOT to do. That’s just as good as learning what to do. It’s part of the process afterall.

So in the end, just be fearless. If you’re feeling scared about a decision, simply ask yourself, what’s the WORST that can happen. More often than not, the worst isn’t really that bad. (NB unless that decision makes you risk your family, etc, then yeah, that’s pretty bad).