How I Started A Private Investigations Business

In late 2015, I couldn’t take it anymore. 

I was 32 years old, newly married, and living in Cincinnati, OH working as a full-time private investigator. 

Yet, I was unhappy with my job. I loved what I did, don’t get me wrong, managing a small team, but I had this urge to strike out on my own. 

I had to scratch the itch, you know, be my own boss, build a business, and leave a legacy. 

But I just didn’t know how to do that.

I Had to Make the Move 

Leading up my disillusionment with my job, I’d been finishing up my Master’s degree, and reading every business book I could get my hands on searching for the answer. 

One book, in particular, sold me, the 4-Hour workweek.  

If you’ve not read it, the author, Tim Ferriss, describes liberating yourself from your 9-5 job, living a globe-trotting life, becoming a part of the “new rich” as long as you can develop a product or service that will fund your lifestyle. 

And, I was immediately hooked, as many had been on starting a “lifestyle business.” Could I do that?

Well, behind my company’s back, I started putting the pieces in place, got my own business license, and then my own P.I. license. 

Eventually, I’d start a side hustle to earn some extra cash, then quit my job, and travel the world with my beautiful wife.

But, my bosses weren’t dummies, they sensed that I was on the way out, and as anyone would, they gave me the boot. 

They fired me.

Now What?

So, although I wanted out, not in this way mind you, I was now forced to figure out this business like right now. 

I immediately got on the phone and started trying for new clients. 

I would actually do this daily, mostly getting nos, for months on end. 

It led me to have doubts, you know. Could this new business earn revenue? Could it get clients? Could I make sales? Even with all the reading, I still had no idea what I was doing.

Then something changed. My wife got a new job offer, where she’d work on rotation at various locations around the world, essentially auditing businesses for this multinational company she worked at. And, I could tag along. We’d live out of hotels and her company would pay our living expenses.

I was like “hell yes!” – while traveling the world, I could finish my graduate degree online, I could test this online business I wanted to start, and the two of us would tour the world. Awesome!

So, we pack up and embark on this adventure and start to live out the dream.

Entering Italy

One of our first stops was Florence, Italy, the land of fantastic food, delicious wine, and incredible architecture and history. What a wonderful life!! 

We get to tour areas I’ve always wanted, like Rome, seeing the Colleseum, even making a wish at the Trevi Fountain. It was great.

But, I realize it’s not all it’s cracked up to be. That finding clients is really hard. Who would hire a P.I. they’ve not heard of from a new business? One that is not even in the country. I realize quickly that sales and marketing is hard. You know nothing, Jon Snow. 

I’m working 8 hours a day to get this business rolling, another 4-6 per day to finish off my degree, and my wife’s working 12-16 hours a day at her job. I realize very quickly, that this isn’t the life that I had envisioned. This isn’t the 4-Hour workweek at all.

This Changed Everything

And then this happens. As I’m cooking my wife breakfast in our little Italian hotel room, she emerges from the bathroom holding a small plastic thing in her hand. I remember the look on her face at the moment – it was of pure panic.

She holds out her hand, and there is a pregnancy test. I look down and read it. It’s positive. 

We’re going to have a baby.

And although, she’s panicked. As anybody would be in that situation, I’m happy. I’ve always wanted to be a father. 

Though in the back of my head, I thinking “What the hell are we gonna do?” 

Where are we gonna raise this child? Where’s the nearest doctor? Is my wife even okay right now? Is this baby gonna be healthy? We don’t even speak Italian? Do we have insurance over here?

And, then later I ask other questions too. Like, can I even afford this child? Even having never had a baby before, I know diapers and formula are expensive. Will this business even survive as a result?

Making the Change

And, again I’m forced into action, I’m focused to learn as much as I can about this baby we’re gonna bring into the world, all the while trying to pull together a business and keep my marriage strong.

And then it hits me. Not at first, but later. Sure, for selfish reasons I wanted to be my own boss and start a business. But, I really was doing this to leave a legacy for my family. A family which was about to grow by one.

And, all this hard work, the reading, the studying, the late nights, they all started paying off. Not right away (the business wasn’t successful at first), but after a while.

The money came in – I’d doubled my yearly income. The clients came in even having never met me or seen my face or known my work.

And, we cut our world travels short, moving back home to Cincinnati, where we would raise our first child, a baby boy. 

That was 2016. So, as of 2021, we’re now a party of five. The business is thriving, even exceeding my expectations.

And, what I didn’t know was that my wife, who’d made a wish at the Trevi Fountain had actually wished for? Was to start a family.