Advice for High School Seniors from a Private Investigator Who Nearly Failed High School

For the past three years, around this time of year, I’ve been visiting Putnam Valley High School to speak in front of a class of seniors. The class is run by Bob Baker, whom I’ve known since I was 9 years old.

Mr. Baker, as I have been asked to call him in class, teaches math, but once a year he gives a math-applications course where he teaches seniors about applying some of the math they have learned in school to real-life situations like paying taxes, obtaining a mortgage and making investments.

The class also has a bit of career, entrepreneurship and business advice thrown in; the students listen to a few guest speakers in class, go down to Wall Street and attend a career day at MetLife Stadium.

I truly love speaking to this class every year, and I’m not really sure why. First off, who doesn’t like talking about themselves for about an hour?

But I also feel like I have an interesting story to tell, one that high schoolers can relate to.

I think it’s also because by my own definition, I’ve had a pretty successful career and I think I have the best job in the world. When I talk to the students, I share some of my past about how I got to where I am, some of the things that helped get me there and some stories of my most interesting cases.

I also talk to them about being careful what they post on social media, but hopefully I’m not the first one to do that.

While we all have a story, I can totally relate to where they are as high school seniors. This investigative story seems to be the fan favorite.

Here are a few things that always seem to resonate with the students.

Be a Writer

I was a horrible writer in grade school and high school. I literally couldn’t put a few sentences together. I couldn’t collect my thoughts or write anything cohesive. I remember my father literally throwing an entire draft “book report” in the garbage because it didn’t make any sense. I know that probably frustrated my family members; after all, I am the grandson of a novelist and screenwriter.

Things started to change in college. I’m not sure what happened, but I do recall one class where we were required to write no more than two pages for anything that we handed in. I remember being forced to write more succinctly and clearly, and without jargon, fluff or extra words.

Also at that time, I started to read a lot more. I started mostly with the newspaper, which I have been reading religiously every day since. (I think I picked up that little nugget from Rick Pitino’s book Success Is a Choice: Ten Steps to Overachieving in Business and Life, which I highly recommend.)

Ironically, today I write a lot, including this blog, which is up to about 300 posts. I also write investigative reports and memos on a daily basis; for those, I need to be to-the-point, factual and jargon-less.

I still don’t think I am a great writer, but I do know one thing – writing takes work. Lots of it. So my advice is to write. Whatever it is – poems, emails, journals, fiction, fantasy or haiku – just keep writing.

And read too. Whatever floats your boat. (Maybe start with a newspaper.)

Build a Network

There are two things that I credit my “success” to. The first is hard work. I have never pretended to be the smartest person in the room, but I can outwork just about anybody. And that doesn’t require any special skills or superpower.

The other thing that I credit success to is networking. Ten years ago, when I left my cushy salaried desk job with medical benefits to start my own business, I had a wife, two young kids, a fairly substantial mortgage to pay and a whole lot of confidence (also known as ignorance) that I was going to make a living on my own.

One thing I did have was a good network of people I had come to know and trust over the years. When I sat down on day one of my entrepreneurial venture, I called and emailed everyone I had come across in my professional and personal life.

Shortly after, I began my first case, helping my client prepare for a trial. For two and a half weeks, I worked long days and nights, including a 17-hour day on Labor Day. That first client has turned into a 10-year client. The rest, as they say, is history.

What I didn’t know then, but know now, is that my network literally started my business. I had always treated people with respect and made it a point to keep in touch with them, help them out when needed and ask for favors when appropriate. I did it to be a decent human being, not because I wanted to be a good networker.

What I have come to realize is that every interaction you have is literally building your network. A network that might be able to help you in the future. That person next to you at your lunch table might be able to help get you a job in the future or maybe even inspire you to do something that you hadn’t thought of.

So go ahead and be kind to people, take an interest in someone else’s life, or just be a good listener.

You never know when you might need someone in your “network.”

Perseverance

I am a competitor at heart. My younger brother would frequently let me beat him in basketball just so I wouldn’t quit playing. I’ve also been known to get a little too amped-up during family game night.

Early in my career, I was told that I wasn’t a very good investigator. People openly doubted that I would make it when I opened my own business. They doubted that I could run a business since I was insecure, not mature enough or lacked the skills to be a manager.

Sure, I needed to grow up a bit, and some of that criticism was well deserved.

But all the doubters did was put a bit of a chip on my shoulder, making me want to prove them all wrong.

Athletes like to call that finding an edge.

Whatever it’s called, I like to push my own personal boundaries.

It’s worked out pretty good so far.

High School and College

I was a terrible high school student. I broke my arm in the ninth grade and thought that was a good excuse not to do any homework or study for any tests during the six weeks my cast was on (I think I failed every class that semester).

I got kicked off the baseball team in my senior year because I hadn’t shown up to my first-period biology class in months.

I finished exactly 106 out of 212 students in my class, just between the biggest burnout and the class clown.

I applied to exactly one college, 30 minutes from my house, only because all my friends were going to college and I didn’t want to be left behind. After a year, I dropped out, realizing that I had exactly zero ideas about my future.

I ended up working in the sports industry for a local photography firm that licensed professional sports photos. That led me to pursue a degree at the University of Massachusetts at Amherst, which at the time had (and maybe still does) the best sports management program in the country.

I graduated cum laude and ended up working in the sports industry for a few years before determining that wasn’t for me either.

All this experience led me to work as a private investigator at the age of 25, and I’ve been doing it ever since.

I was 17 years old when I graduated from high school. I had no idea what I wanted to do, which scared the hell out of me.

The reality is that most graduates really don’t know what they want to do. My colleague just found his passion at the age of 40.

I love what I do, but frankly, I could have loved 30 other things too. Who knows?

If you are 17 or 18 years old, you have time to figure things out, so be patient, don’t settle, work hard, persist, hustle and keep following your passions until you find one that sticks.