MY ENTREPRENEURIAL JOURNEY

A series of well-intentioned decisions, some better than others.

People often look at successful entrepreneurs and assume they had some magical roadmap. They imagine a perfectly planned journey filled with strategic decisions, flawless execution, and a steady climb to the top. I’d like to officially clear that up. My entrepreneurial journey has been more like driving a race car while simultaneously building the engine, reading the owner’s manual, and trying not to hit a wall. Somehow, it worked.

Growing up, I was surrounded by entrepreneurs. My father sold custom clothing, worked harder than anyone I knew, and taught me one lesson that permanently rewired my brain. When I asked him how to balance a checkbook, his answer was, “If you need more money, make more money.” Now, to be fair, that was a terrible answer to the actual question. But it was fantastic life advice.

While other people worried about whether there was enough pie to go around, I grew up believing there was always another pie. If I wanted more, I could create more. That mindset has probably been responsible for both my successes and at least a few of my more questionable business decisions.

Over the years, I’ve built companies, sold companies, bought companies, started new ventures, and occasionally made deals that had my advisors staring at me as if I had completely lost my mind. Sometimes they were right.

One thing I’ve never been afraid of is taking a risk. I’ve always believed that if you wait until you have all the answers, somebody else has already taken your opportunity. So, I’ve jumped. Sometimes I landed gracefully. Sometimes I landed face-first.

One of the biggest surprises in my career was learning that business isn’t really about selling. It’s about listening. Some of my best deals happened because I shut up long enough to hear what was actually going on. People love to tell you everything if you let them. Suppliers told me things. Customers told me things. Competitors accidentally told me things.

A shocking number of people practically handed me multimillion-dollar opportunities because they couldn’t stop talking. Meanwhile, I sat there nodding, asking questions, and taking mental notes. It’s amazing how much easier business gets when everyone else is giving away the answers.

I’ve also learned that growth requires getting comfortable with being uncomfortable. Every major leap in my career started with me feeling completely unqualified for whatever I was about to do. Start a business? Terrifying. Sell a business? Terrifying. Buy a manufacturing company? Also terrifying. Sign the paperwork anyway? Apparently, that’s where the magic happens.

The funny thing about entrepreneurship is that people see the successful outcome but not the hundreds of moments when you’re convinced that you’ve made a horrible mistake. They don’t see the sleepless nights. The bad hires. The expensive lessons. The deals that almost happened. The deals that absolutely should not have happened. Or the moments where I’d walk into work thinking, “Well, this seems like a problem for Future Courtney.”

Then Future Courtney shows up and discovers Present Courtney has once again left her a mess.

I’ve become convinced that age is one of the greatest scams ever sold to entrepreneurs. People ask me when I’m going to slow down. Slow down? I finally know what I’m doing. Well, … more than I did at 30. At 30, I had ambition and stress. Today I have ambition, experience, confidence, and enough scar tissue to recognize trouble before it introduces itself.

The older I get, the surer I become that entrepreneurship has no expiration date. In fact, I think it gets more fun. You stop worrying about what everyone thinks. You trust your instincts more. You understand that mistakes won’t kill you, and sometimes the biggest opportunities come disguised as complete disasters.

When I look back at my career, I’m proud of the businesses I’ve built, the people I’ve worked with, and the opportunities I’ve created. But what I’m most proud of is that I never stopped learning. I’ve never believed I was the smartest person in the room. I’ve just been willing to stay in the room long enough to learn something.

The truth is that entrepreneurship isn’t about perfection. It’s about resilience. It’s about getting knocked down, getting back up, and occasionally pretending you knew what you were doing all along.

So, if there’s a secret to my success, here it is: Work hard. Listen more than you talk. Take the shot. Learn from your mistakes. And if all else fails, remember my father’s advice. If you need more money, go make more money. Just don’t ask me how to balance a checkbook.