How I Became a Private Investigator #160

Not everyone becomes a private investigator the same way. There are many different and unique paths that people take on their road into the investigation industry.  Many police officers find themselves becoming private investigators after they retire or leave law enforcement.  Some people come from a Loss Prevention background when they enter the industry.  And others enter the private investigation industry with little experience at all.  I felt it only fitting to share how I became a private investigator.

There is no one path to get into this industry and there is no one path you must take once you’re in this industry.

I think I have discussed how I became a private investigator on a podcast long ago but I think sharing my career path over the years might shed some more light and maybe inspire some to keep pursuing an investigation career.

After High School

I think it would only be fitting to start this story after I graduated high school.  I thought I knew everything (like all young adults) and I thought I was going to make a ton of money with no skills or experience in anything (except for maybe painting).

My first 3 years out of high school were mixed with being a painter (houses, businesses), delivering pizzas, working for a temp agency, and working in a warehouse.  

I also did a semester of college somewhere in that mix of time. I only went to college because I wanted to continue wrestling.  Since I really didn’t care for school I didn’t do that well in my classes and dropped out after wrestling season concluded.  

During this time I didn’t know what I wanted to be or do for a living and  I didn’t have any real aspirations regarding my career.  

I basically wasted 2 years after graduation with no real direction.  I had turned 21 years old, I stayed up late every night and slept until the afternoon every day.  And then one day my father called me from work and he gave me an ultimatum of sorts to get me moving in some direction; any direction. The conversation wasn’t mean.  It was loving and matter of fact.  

He gave me three options to pursue during our conversation and they were:

  1. Resume college full time and get a degree
  2. Find a full-time job making over $15.00 an hour
  3. Join the military

The College Option

On that day I made my way to two different colleges to see when classes would be starting.  The two local colleges wouldn’t be starting new classes for several months.  In my mind, this meant that college just wasn’t going to be an option.  And truthfully I really didn’t want to return to college at that time.  I just didn’t like school.  

Find a Job Making Over $15.00 an Hour

In 1998 the internet was not as sophisticated as it is now.  And in those days when someone was unemployed, they found jobs in the newspaper or the unemployment office.  These were the trusted ways to find jobs at that time.  Now newspapers are the last places people look for jobs.

I looked in the newspaper and didn’t see anything I could do or was qualified to do.  I drove to the unemployment office and scanned through jobs using their computers.  I left feeling concerned and disheartened that I did see anything I could do or was qualified to do.  

Join the Military Option

In Antioch, California there were three recruiting offices for the Army, Marines, and Navy all next to each other.  I found myself in the Army recruiting office speaking with a recruiter.  I spent 4 hours straight talking to him about the Army.  

He told me how the Army had the most jobs to choose from, how I could pick my job as long as my test scores qualified me for the position and how there were approximately 200 different jobs to choose from. He told me that other branches of the military either didn’t let you pick your job or there weren’t as many to choose from.  I would also have an option of where my first duty station would be.

I came home and told my parents about it and spent the rest of the day writing more questions to ask the recruiter the following day.

The following day I returned to the recruiter’s office and spent another 4 hours with the recruiter again and decided that joining the Army was the route I was going to take.

After some test taking (ASVAB), I qualified for nearly every job in the Army.  After some careful consideration, I choose the be a 31F which was a Network Switching Systems Operator. With technology and cell phones gaining momentum at that time I figured I would have the skills needed to land a quality job when my time was over in the Army.  

Army before I became a private investigator

I spent 2 months in Fort Benning, Georgia for Basic Training (learning how to fight).

I spent several months in Fort Gordon, Georgia for my Advanced Training (learning my job)

And then I arrived in Fort Hood where I spent the next 3 ½ years of my Army career.  I met life long friends and had experiences that I might not have ever had if I didn’t join the Army.  My time in the Army told me a lot about what I did and didn’t want in a career and the type of people I wanted work for.

Many friends in the Army found great telecommunications jobs with companies like Sprint as Sprint was a big dog in the cell phone industry back then.  However, the closer I got to getting out of the Army the fewer jobs seemed to be available.  

POST ARMY (Newspaper Delivery, Law Enforcement, and Loss Prevention Options)

By the time I got out of the Army I couldn’t find a job and I returned home with only a couple of months to find a job because my saving would be exhausted by that point.

To add some future context to this timeline I had also met my future wife who lived in the state of Washington.  This plays a role in my decisions as you will see later.

Many of my friends were becoming police officers after leaving the Army and thought that would be a natural transition and a good career to go into.  So I started applying for different police departments including the California Highway Patrol.  The process and the testing process for police departments are very long and I had to get a job while I pursued a law enforcement career.

At the time brother worked for GAP Inc at an Old Navy store as a Loss Prevention Agent.   Loss Prevention Agents catch shoplifters and he was very good at his job.  I asked him to get me an interview with another GAP Inc brand that might be looking for another Loss Prevention Agent.  I didn’t want him to get me the job, I just wanted an interview.  

I eventually got my interview opportunity and was hired by the Banana Republic Regional Manager.  Within the first week I was able to find fraudulent transactions being made in the store I worked for that hadn’t been discovered by the previous loss prevention agent and I was able to find patterns in some return fraud scams that were taking place.  I had a knack for looking at information and connecting dots that others weren’t connecting at the time.  

By the end of 2002 I had proposed to my future wife and we were to be married in 2003.  I was making about $12.50 an hour with Banana Republic and it just wasn’t enough to pay for a wedding or to live off of.  So I did what any person would do and picked up a second job delivering newspapers in the morning..7 days a week.  I think I made something like $650 dollars a month extra having the paper route.  

In 2003 I was married and was still working two jobs and it was killing me and it was taking its toll on my wife as well.   I would never see her and I was always working.  I never seemed to have a day off.  

How I Became a Private Investigator

While working for Banana Republic I came to know a manager from another store who was previously a private investigator.  I was getting desperate by early 2003 to find one job that provided as much income as the two jobs I was working.  So I started asking him about the job and life as a private investigator. After some conversations I thought it might be a good fit for me, so I started applying for investigation companies hoping to get out of the hole I was in.

I remember talking to a potential private investigation employer who said he was looking to hire someone that was interested in starting their own company in the future. I told him I wasn’t interested in having my own company. He said I wasn’t the guy he was looking for.  I said something stupid like, “You’re missing out by not hiring me.”  I didn’t get hired.

I applied for other investigation companies as well and finally got a call back from the trainer at Omega Insurance Services who was interested in me as they had found that hiring people with Loss Prevention experience worked well for them as many of their top employees were Loss Prevention Agents before getting hired on.  After filling out all the application paperwork there was a long wait before I got an invitation for a ride along which was the determining factor before getting an offer with the company.  In fact I kept calling the company and asking when I could get my ride along with another investigator.  

It should also be known that about this time in 2003 I had passed all the testing for the California Highway Patrol and I was just waiting for an invitation to the California Highway Patrol academy.

Anyways, I eventually got my chance for a surveillance ride along with an Omega Insurance Services investigator.

I arrived dressed up fancy for this ride along interview.  My interviewer was this nice guy and about my age. During the surveillance, I asked questions and picked his brain about the job.  He asked me many questions as well.  And during that time in the car somehow our faith came up and we just happen to share the same faith.  

After hearing about the company and the job I felt like I would be a good fit and he felt that way as well.  

A few weeks later I was offered a position as a surveillance investigator in the state of California.  I was then flown to St. Petersburg, Florida to attend a week of classroom and field training.

Let me just say I was extremely paranoid and didn’t know what to expect.  My first night there (the day before the first class) I literally thought the Omega Insurance Services had stuck spy cameras in my hotel room to watch me.  I didn’t know any better.  And by the first day when the class received all of its surveillance equipment I felt secure believing that this company wasn’t spying on me.

This is the equipment each new investigator received:

  • A video camera
  • 8mm tapes
  • Cell phone
  • Computer
  • Spy Camera
  • Training material
  • Fake company pretext material (business cards, door hangers)

The training I received was very practical and I believed was a great foundation for the job.  

After the training, I returned home and then spent the next 4 or 5 days sitting in a vehicle with another investigator who continued to train me on actual cases that he was working.  On the last day, we walked around a neighborhood pretexing people trying to find out random information. Pretexting wasn’t fun but it was part of the job and something I needed to get comfortable with.  And I was eventually released to work my own files.

I, of course, had to check in with supervisors and managers.  And I had to ask for help all the time early on in my career.  

Over time I became a pretty good surveillance investigator.  I also began to learn how to be a claims investigator as well.  

By the end of 2004 I received a call from the California Highway Patrol telling me I was invited to the academy which was a live-in academy.  My wife was pregnant and my daughter was going to be born during the time of academy.  After a variety of things were considered I decided to pass on the academy and law enforcement as a career in general and continued to be an investigator.

I eventually became and Alternate Field Agent in Charge (alternate field supervisor).  I was then promoted to Field Agent in Charge and I eventually got promoted to a Territory Manager which basically covered the Northwest.

Between 2003 and 2010 I worked for a couple of companies.  There were some good financial times and some bad ones.  I also earn an AA in Criminal Justice and BS in Business Management through the University of Phoenix.

In 2010 I applied for my agency license for my own company (Fortified Investigative Services) and I was also hired on with a different company as an employee.  This was great because I was either busy with my company or the company I worked for as an employee.

I launched this blog in 2011 to share my journey of starting a private investigation business.

How I became a private investigator after many years

Final Thoughts

From 2010 to now my priorities have shifted a bit but I still enjoy different parts of the private investigation career and life.  I still don’t enjoy other parts of this career but those are the things I try to avoid.

I think one of the outcomes I am most proud of is the P.I. Advice website, the videos and the podcast.  I love teaching.  

I hope to share other journeys of private investigators in the future in addition to how I became a private investigator to show you that there is not one path that leads to this industry.  

If you have any questions about how I became a private investigator feel free to ask in the comment section and I will answer what I can.  



  1. Im in the security business and would like to start my own pi business

  2. Great piece, Andrew. Thanks for sharing!