How to Learn from Your Startup’s Mistakes

I started a podcast about four years ago called Beyond The Uniform, and it was all about helping people in the military figure out what they want to do when they leave the military. That came out of my own experience where I was on submarines. I love the culture; I love the people. I love the work. But I knew I didn’t want to do it long-term. And my decision-making process when I left submarines was as simple as I like managing people. I like teams. So there’s probably something in business to do with that. Let me go to business school and figure it out. 

In my first quarter at Stanford, I was having coffee chats with classmates and saying, Look, you’re an investment banker isn’t like a teller at a bank; I just had no concept of what career opportunities were. And during my time in business school, I realized companies come from startups. Baby companies grow into big companies, and you can find a pain point, solve it, and start your own company. And so I took a big bet on myself and left the consulting world to start StoryBox. 

I think it was probably just as simplistic as my decision to leave the Navy. It was just really a love for the art of creating something new. And I think what became addicting to me was when I had sketched something out on a piece of paper of what my first website would look like and hired some developers to build it. And weeks later, I’m interacting with something that just came out of my head, and it was brought to life. And it started to solve problems. 

The artist in me was drawn to that thought of just finding creative solutions to problems. And that’s what ultimately led me down the path of StoryBox. It’s been going for ten years now with many mistakes along the way. Still, I don’t know if there’s a way to learn more efficiently in entrepreneurship than just getting your hands dirty and making mistakes and hoping to leverage the mistakes of others and learn from them. But it’s funny because now that I’m on to my next startup Captivate. Many of the mistakes that I made with StoryBox are informing the way I approach things with Captivate. You zoom out far enough, and it feels like every error leads to an insight that hopefully is course correction down the road.

You could read every textbook in the world, you could go to Stanford, but you never know what it’s like until you do it, until you have success, until you have the failures, and everywhere in between. It’s like, I use a military term, earning your stripes. I mean that you could talk, you could tell me what it’s like to be in the military, but I will have no idea until I’m earning those stripes myself. Right. The story is that you continue to move forward. Inevitably you’re going to make some mistakes. There’s no doubt about it. If you’re not trying, you’re not going to make any mistakes.

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