Serial Entrepreneurship, Cyclical Success

As an early founder, I thought about when (not whether) things would stop going well at my company. It was a bit of founder paranoia, which sounds crazy but is healthy and common (only the paranoid survive). It didn’t mean my behavior changed. It meant I was aware that continued success was not a given and had to be earned.

As I’ve reflected on this more, I’ve realized that there was something deeper in the back of my mind that was more personal. Since high school, my trajectory had been mostly up and to the right. Most of the things I tried, I succeeded at—some minor hurdles, but no material failures. I was appreciative of but also concerned by this trajectory. I couldn’t put my finger on why, but I can now.

Success isn’t indefinite. It’s cyclical. Anyone who has achieved outsize success has also experienced a setback or major failure. Said differently, they’ve experienced highs and lows, or a cyclical journey.

At CCAW I was pushing for more success, but subconsciously I was bracing for an inevitable setback. As crazy as it sounds, that mindset ended up being helpful.

I didn’t know when failure would happen, but I knew it would happen. So, when I encountered a setback, I wasn’t surprised. Instead, I looked at it as a necessary part of the cyclical journey to success. I wasn’t thrilled by the setback but made sure to look for the positives in the situation. I focused on identifying what I could learn. I tried to figure out how what had happened could position me for a bigger win. That mindset helped me navigate the setback and come out on the other side better positioned for bigger things.

My big takeaway from this is that I can be a serial entrepreneur, but my success will be cyclical. Said differently, serial entrepreneurs have cyclical success. I will try things, and some of them will fail miserably. Instead of thinking I’m winning or losing, I now view it as winning or learning.