I Bought My First Limo at 19 With No Money. Here Is What 33 Years Taught Me About Growth

I was 19 and working at a deli when I walked outside and saw a man selling a limousine. It was a 1983 Cadillac, blue with purple tinted windows, and it was not a nice car even by the standards of the day. I had zero dollars, and my family did not have the money to help.

So I went to the bank. Back then you could still walk in and shake someone's hand. The bank president gave me the loan and told me that if I was one day late on one payment, he would personally come repossess the car.

I knew nothing about business. I grew up an hour north of New York City and had never been to the city or to an airport. The first time I drove into Manhattan, I had clients in the back seat. I figured everything out on the fly, and I ran that company for the next 33 years.

Every ceiling required a new lesson

We started in weddings and hit a ceiling. The cars worked two days a week and sat the rest. So we reinvented the business into corporate sedans and SUVs, then buses, then a brokerage model that served clients in 650 cities. That last piece, the one built on relationships instead of equipment, ended up being the most valuable part of the company.

Each ceiling forced an education. At one point we were generating a lot of revenue and not making money, and I had to go back and teach myself finance to understand why. In EOS we say that when you hit the ceiling you have three options: flatline, break through, or fail. I was fortunate to break through more than a couple of times, but never without pain.

Growth does not have to mean bigger

The number one thing I see owners struggle with today is shiny object syndrome. An architecture firm decides to open an ice cream stand. A firm that is full one day a week wants more space. Gino Wickman says you are more likely to die of indigestion than starvation, and I see it constantly.

Growth matters, and your business has to grow. But if you are a $5 million company, you do not have to become a $10 million company to be growing. You can improve margins, tighten your focus, or get better at what you already do. Owners worry about capacity problems they do not have yet, and miss the opportunities sitting in their own backyard.

Solve the one issue underneath the fifty

I sat down with a client for their first meeting and they had 57 issues on their list. We picked the most important one and solved it at the root. When we looked back at the list, about six were left. The other fifty were symptoms of the same problem.

When you are in the trenches, nobody has time to step back and find that one issue. That is exactly why you have to.

What I would tell my younger self

If I could take one EOS tool back to 19-year-old me, it would be the vision work. The vision was as clear as day in my head, and I could not understand why my team did not see it. Communication is the most basic skill in business and the hardest one to do well.

And to anyone starting out: be passionate about what you are building. If you are only chasing the money, you will not make it through the trenches.

More conversations like this on the podcast page, including the Lead Counsel show I co-host.