Entrepreneur, Advisor, & Investor
“Was there a moment when you knew you wanted to start your own company?”
I’ve been asked this question a lot, and looking back, it’s no surprise why. Entrepreneurship has shaped most of my life. My dad launched his first business when I was five years old, and I watched the way he was able to support our family while still making time for us. In high school and college, I took full advantage of any leadership role I could find, often with a compulsive drive to succeed in it. Over the last 30 years, I have built and managed a 9-figure organization and invested in multiple companies that’ve had successful exits.
It all began eleven months into my first job after college
My business partner and I jumped ship and formed our own travel insurance company. It was less about the travel insurance, and more about the thrill of starting a business.
We borrowed $10,000 from my partner's parents, convinced we could scale the business and sell it in three years. This was more than an opportunity—it felt like my destiny.
But destiny doesn’t always go according to plan.
Nothing could’ve fully prepared us for the realities of running a business. We had to take on second jobs, tighten our belts, and double down hard in order to survive that first year. My family was facing financial challenges, and the leadership experience I had gained in school could only take me so far. It seemed that the ships which had brought me here, were burning in the harbor. Still, success was our only option.
We made it through—and little did we know—the real challenge wouldn’t come until 15 years later.
We were now a 200-person company that was trying to run like a small startup. Our customer service was beginning to slip, costs rose, and I became terrified that we were showing signs our our imminent decline.
At the same time, our work place became toxic.
People were constantly undermining one another, and trust in our leadership team began to erode. I raised my concerns, but they were often ignored. I couldn’t pinpoint exactly what was wrong—I just knew we were heading downhill fast and I was losing sleep over it.
A pivotal moment in my entrepreneurial journey:
The turning point for me was when I went on vacation. It was supposed to be my time to separate from the chaos, but the chaos had followed me thousands of miles away. A partner called to tell me one of my directors was upset with a decision I had made. Instead of this director supporting me, he immediately began questioning my decisions, undermining the calls I had made. I was seething with anger for days. This was a company I dedicated my life to. What was I going to do if it failed?
When I came home from vacation, I told my partners we needed to make serious changes. We were just too close to the staff, and we needed an outside person to run the day-to-day operations as our COO.
Looking back, it was the right call, but we made two key mistakes:
First, we didn’t hire the right person. Our toxic work environment was continuing to fester while we stayed busy growing the company. Despite doing extensive research, the COO we hired was either unable to see this, or saw it, and failed to help us improve it.
Second, my partners and I allowed ourselves to creep back into the day-to-day operations of the company, thus undermining the COO we had hired to run it. For years, we struggled to correct this misstep to no avail.
Five years later, everything changed.
A college friend introduced me to Susan, an HR Consultant who had left a fast-growing tech company to run her own firm.
Our initial meeting was supposed to take an hour, but turned it turned two, (which became a reoccuring theme with us). As my partner and I started describing the problems we were facing, she had answers to every single one. I was thrilled.
But it wasn’t just the answers that got me excited, it was that she explained “the why” to me as well. She validated what my concerns had been all along. Finally, we could see what was really happening beneath the surface.
“The problems start at the top,” Susan said.
She pointed out that my partners and I were modeling the wrong behavior for our staff. When she said this, the movie Saving Private Ryan popped into my mind. Tom Hanks' character was in charge of a unit, and a member of that unit asked why they all complained to him, but he never complained to them. Hanks said that he did, but not to them. He complained to his superiors. “You complain up, not down,” he explained.
The problem was that my partners and I had allowed our subordinates to get too involved within our own stuff. Instead of maintaining clear boundaries, they became entangled in our grievances which undermined our leadership.
Susan developed a plan to completely reform the company.
I called it the “Apollo Program,” because it be would be like taking our company to the moon. Of course, we had resistance from day one. We had to choose between educating our directors or replacing them. We chose to educate them, but six months later, we had gotten nowhere and realized it was time to find the right people for the right roles.
In total, it took us five years to transform the company and create a healthy, positive culture.
Now I better understood human nature as it relates to the workplace. I can spot toxic problems early and now how to hire the right people who will fit our culture. In the end, I was able to hand over our daily operations to a key executive who has exceeded our expectations as owners.
Since then, I’ve carved out my niche in the entrepreneurial world, helping people navigate similar challenges, investing in startups, and pursuing new ventures. Over the last 30 years, I’ve realized that entrepreneurship requires a special blend of creativity, adaptability, and determination. Successful entrepreneurs can tolerate embarrassment and know how to embrace risk.
So, was there a moment when I knew I wanted to start my own company?
I can’t think of any singular instance. It was probably always inside of me. Just like the answers were all along. I’ve learned that each challenge we face has an air of mystery to it. Your job isn’t to know all the answers, it’s to stay attuned to the problems. Sometimes, I’ve found it can be helpful to have someone reflect your own beliefs back to, just as Susan did for me. She mirrored my instincts, and affirmed what I already knew: that the solutions were within reach, I just had to take the risk and embrace them.
If you’re a leader who sees the potential for greater success but feels blocked by internal obstacles, or if you’re leading a start-up that’s struggling to find its footing, I’d love to help.
With over 30 years of entrepreneurial experience, I know how to identify what is really going to move the needle in your business. Whether you're a seasoned executive or a founder looking to pivot, I can offer the guidance, support, and investment you need to break through and achieve your goals.