Photo by Alvaro Reyes on Unsplash

Second Time Around: 7 Lessons I Learned from Losing My First PI Firm

Here are some things I wish I’d known when I first pursued my dream to open a private investigations business.

From noir novels to the real-life case grind, one of the reoccurring motifs of the private investigator’s world is the ability to take a hit, get back up, and keep going. While I’ve never been subject to a Marlowe-esque shakedown, I have taken a hit to the proverbial chin. For a time, I lost sight of the dream, and I’m just now getting up for round two.

My road to the private investigation’s world isn’t typical, I came up through the ranks of the auto repossession industry, where I was a skip tracer.  When I obtained my PI license, I immediately joined all the associations and started cold-calling attorneys. Then I sat back and waited for the jobs to roll in — which they did, but slowly. 

Continuing to work full time and building a practice isn’t easy, especially when you blaze past the business development part and figure, if you just focus on doing the work, that’ll be good enough. I’ll bet you know where this story is headed.

Fast forward through a few years of low caseloads, bad advertising money following worse “discounted rates,” Covid, and family growth, I hit my wall, put my license in a drawer, and closed shop. Being a P.I. had been my dream since childhood. The sense that I was losing my chance was devastating. 

I was down but not out. 

In a letter to a fellow scholar, the famous paleontologist William King Gregory wrote, “Planning is simply the result of experience read backward and projected into the future.” A few years of downtime and reflection have brought some new insights and life lessons that I wish I’d understood when I first started on this path:

1. Not being ex-law enforcement can be a huge asset. 

My area is saturated with retired law enforcement folks who have picked up P.I. work as a second career. Their rates are lower, and they carried the big titles: FBI field agent, homicide detective, etc. Certainly, their experience gives them deep insights into the justice system, but it can also lead to a rigid approach that’s often hard to overcome.

What I learned from this: Capitalize on the absence of ingrained bias that a career in law enforcement can embed into your practice. Focus on the ability to find workarounds to roadblocks that law enforcement may not have encountered — i.e., if you never had a badge to open doors for you, you had to learn to open them some other way.

2. Plan your business and follow the plan. 

Be a business owner first, investigator second.  My biggest failing was not creating a solid, workable business plan.  If you’ve never made a business plan – take a class, many are available free through public library resources.

What I learned from this: Put serious effort into where your cashflows come from, where they’re going, and what clients you want to take on. Spend money on market analysis as an investment in future advertising efforts. A little money spent now will save a ton later.

3. Don’t just lurk at industry functions, ask questions and be willing to listen. 

I always had a bit of imposter syndrome at different industry functions. To my mind, these people were the real deal, and they were going to see straight through my lack of experience and write me off as playing at being an investigator.

What I learned from this: Everyone starts somewhere, and most experienced investigators are more than happy to mentor. They’ve all been where you are and can provide valuable insights into how to grow. Most of all: folks mostly don’t write off the newbie who’s suffering from impostor syndrome if he’s curious, respectful, and eager to learn.

4. Not all advertisements are equal.

No matter what popular marketing companies tell you, no one reads postcards. I threw good money after bad on failed advertising efforts that just drained my bank account with no ROI.

What I learned from this: Target your market, go to an industry function, and find out how they’re learning about new business. Invest as much time in getting the facts about your client as you do on a case.

5. Don’t just ask for referrals. Chase them.

I always had a blurb at the end of my case summary emails asking for referrals, assuming a satisfied client might reward my efforts with a comment or star ratings.

What I learned from this: Call your clients after the case, ask them if they’re happy, and politely ask for a referral. Ask them what they thought of your work. Send them a summary statement to approve for use on your website. Ask for referrals to other clients and follow up on those referrals. The worst they can say is no. 

6. It’s okay to acknowledge your weaknesses and ask for clarification.

I can’t count how many times an attorney client assumed I knew what they were talking about, and I didn’t ask for clarification for fear of seeming incompetent.

What I learned from this: Ask the question. Call/email back for clarification. The client is invested in receiving the right material and will be thankful for a question up front instead of after 10 hours of an investigation in the wrong direction. Remember: you’re the expert and should have the knowledge to provide a quality product, but no one knows everything always.

7. If you don’t value your work, your client won’t either.

Giving discounts, free work, not billing all hours may seem like a great way to get a client to sign with you or entice them to throw more work your way. But all it tells them is that the work you’re providing isn’t worth what you say it is.

What I learned from this: Bill what you work and stand up for your fees. You are a professional, and the work you’ve done reflects hard won knowledge and experience.

Final Report

Dipping back into the deep end isn’t easy. But with the lessons learned, I’m looking forward to the future. I’m taking it slower this time as I roll out my PI practice. I pay my bills with a job as a compliance manager for a national skip-tracing company that handles repossession forwarding. Meanwhile, I’m focusing on networking and building my skill base. Lately, I’ve found myself helping more people with their investigations than working cases on my own — a fun and rewarding way to accomplish both networking and skill building, On reflection, it looks a whole lot like what William King Gregory might refer to as “planning.”

For anyone who’s struggling with keeping their dream afloat, keep in mind what the great Yogi Berra said: “It ain’t over ’til it’s over.” 


Shaun Gustavson is a licensed private investigator and an assistant vice president of regulatory compliance for a nationwide repossession forwarder and skip tracing firm. During the past decade, Shaun has served as a subject matter expert for the California P.I. licensing exam, conducted civil and criminal investigations, and continued to pursue a lifelong love of the investigation industry.