Ten years ago this month, I was about to take the biggest risk of my life: starting my own business. And I was doing so with a mix of excitement and exhilaration, along with a healthy dose of fear and terror.
It was also kind of bittersweet. I was leaving a firm where I had formed so many important relationships and I had literally learned everything I had known up until then about this business, having started as a complete schlep.
I wasn’t just any schlep, though; I was the boss’ son, which always complicated things. I always felt I needed to prove something. I never wanted anyone to think I was handed anything. And was constantly fighting the urge to prove everyone wrong, including the boss.
I always had the bug to start my own business. I’m not totally sure why. Maybe it was the entrepreneurial bug that I always read about? Or just the idea of running my own business? Or not having to take orders?
But I do remember thinking that I wanted to be able to do whatever I wanted to do and wanted more freedom to escape from regular work hours.
And despite my confidence (or complete ignorance, depending on how you look at it) that I can make a living on my own, looking back, it might be one of the dumbest things I have ever done.
I’m not exactly sure what I was thinking.
I had two small children under my roof.
If you are 33-year-old private investigator who suddenly has to fend for himself, you better have some qualifications up your sleeve other than the fact that you worked for your father’s private investigation firm.
My wife was a stay-at-home mom and my salary was the sole source of our income.
And I had only been a private investigator for eight years, which puts me somewhere between an infant and a toddler in this business.
I also had zero law enforcement experience. Which is not at all necessary in this business, but if you are 33-year-old private investigator who suddenly has to fend for himself, you better have some qualifications up your sleeve other than the fact that you worked for your father’s private investigation firm.
Lastly, having only worked for one firm for my entire investigative life, I really had no idea whether I was really any good at what I did. I was pretty confident I knew what I was doing, but I didn’t know how well I stacked up against everyone else.
I was about to find out.
With $10,000 of my own money, I set up an S corporation; designed a logo; registered my domain; applied for a New York private investigator license; bought a Dell desktop computer, two monitors, and a laptop; and built myself a home office in the basement of my condo.
It was mid-August and about five days into my new adventure, with dozens of “feeler” emails having been sent to old friends and colleagues, when I got a call from an old colleague of mine that his firm needed assistance on a case that was about to go to trial.
Monday, August 24, 2009, I started my first case, helping to prepare for a trial. For the next few weeks, I commuted from my suburban New York home into New York City. For two and a half weeks, I worked long days and nights, including a 17-hour day on Labor Day.
I noticed the irony in my circumstances on working on that Labor Day almost immediately. I was trying to have more freedom and escape regular work hours by going out on my own, only to be stuck in a Manhattan high-rise for 17 hours while my family barbequed the Labor Day away.
But by the end of September, I was turning a handsome profit.
The next month, I hooked up with some other investigators working on the Bernie Madoff case.
A few months after that, I was spending weeks at a time in Alaska, working on a high-profile case.
As I look back, it was probably the most exhilarating few months of my professional life.
I got to work on cases that I would only read about in the newspaper.
But more important, I learned pretty quickly that I belonged.
And I’m still here…