My 2 Best Lessons From the Military for Entrepreneurship

Thinking back to my days at the Naval Academy and in the Navy, I learned some essential lessons through those experiences that have helped me as an entrepreneur. Two come immediately to mind. 

One is the tenacity; the Message to Garcia, the ability to wake up at 5 am and crank. When I first raised money for StoryBox, I remember someone said, “Hey, I like investing in Veterans because they will roll their sleeves up and break through walls.” Tenacity can certainly be a liability. There were times when I’ve broken through a wall when there was a perfectly reasonable window I could have gone through instead. I’ve made some stupid mistakes by brute-forcing. But I think more than a liability, and it’s an asset to say: I’ll figure it out. I can deal with a lot of ambiguity. And I’ll make it work; I’ll find a way to make it work. 

The second is that I saw many department heads that were not successful as a department head. I knew that they were very successful as a junior officer, they were great as an individual contributor, but they couldn’t, at least when I was interacting with them, shift gears to say: What got me here won’t get me to the next level, I can’t do everything, I have to be a manager. Now I have to delegate I have to oversee, which is a completely different skill set.

And I think of that all the time. I think of whether I have the skill set. I fully expect that if Captivate.ai continues to grow, I’m not the CEO. I’m not an optimizer. I’m not a great manager. It’s the constant question for me at every stage: Will this serve me, my company, and the world for me to grow into this next level? Or do I need to say: hey, this is my lane, I’m going to stay there and let someone else do it.  I think about that all the time for those department heads where they grew out of their zone of genius and couldn’t switch gears. Fortunately, unlike in the military, I don’t necessarily have to evolve to that next level. I can stay in this capacity and choose someone to take over as that CEO role at some point.

Share on