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How I Became a Private Eye

An Intro to Due Diligence
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My career occurred by accident. I was an early 20-something, college drop-out—an aged-out former hockey player with zero prospects—and had no idea what my future would bring. On a lark, and desperate to find my place in the world, I reached out to an investigative firm owned by a relative in the suburban Metro Detroit area. He said the work was hard, with long sits on targets for hours, even days, and the job had a high wash-out rate. For reasons I’m unable to articulate, this discouraging advice only whet my appetite. 

For three years, I worked under a licensed private investigator—essentially as an apprentice—starting from the ground up and knowing nothing of the industry, the skills required, or the grueling intensity of this new career. At that time in my life I was what is commonly referred to as a “normie.” A suburban white kid with no knowledge or experience working in low-income/high-crime urban areas, virtually no street-smarts as they relate to working in hostile environments, and unknowing of the difficulties of working in predominantly non-white cities.

My first day in Detroit, I dug into a lower-east side suburb with drug dealing, corner lookouts, and all manner of overt criminality. We successfully surveilled a municipal employee committing workers compensation fraud and working under the table for an event promotion company while remaining discreet and unseen. Within a 14 hour surveillance, I changed my clothes and appearance several times, switched vehicles twice, and had to bullshit my way into two different businesses to keep an eye on the target.    

The heightened sense of danger was intoxicating, and the adrenaline from discreetly but aggressively chasing a target was addictive. Every day was an adventure with a new specific case mission, new geographic obstacles, a new target, and a new set of behavioral principles to be gamed-out and anticipated. My education of the human condition had begun. It was an incredible, albeit jarring, shock to the system to learn about lifestyles, tendencies, and hazards of the emergent underclass. 

Fast forward almost 22 years, and I’ve experienced innumerable hair-raising events, observed remarkable behavior, and had a front row seat to the social and societal decay most Americans only read about in the news. I’ve seen guns used in domestic disputes, married suburban women operating as sex workers in low-income Detroit, and an unbelievable litany of affluent married men spending seemingly all their time and money on sex addictions.  

Fast forward almost 22 years, and I’ve experienced innumerable hair-raising events, observed remarkable behavior, and had a front row seat to the social and societal decay most Americans only read about in the news. 

For the purposes of risk management and litigation, I’ve surveilled executives of major household name corporations, adult pornographic actors, politicians, celebrities, and government employees to police officers and postal workers, professional athletes, Union representatives, spouses involved in divorce or cheating situations, and random nobodies defrauding insurance companies. I’ve been shot at twice in the Metro Detroit area, chased more times than I can remember, confronted and physically attacked, and had several other close calls where my life flashed before my eyes. 

A house in a dirt lot.
Photo by J.Z. DeLorean

But the perpetual state of discovery I’ve enjoyed made it all worth it.  I’ve explored the obscure and forgotten areas, towns, cities, and regions of Michigan and the wild and unusual people one encounters operating in the shadows. Laying in wait within a crumbling and dystopian neighborhood of Flint, Michigan, with scarcity of water and a heavy layer of hopelessness in the air. Sitting undercover inside a bustling east-side Detroit burb with chaos occurring minute by minute. Dug deep into the Brightmoor area of Detroit’s west side, where empty fields now sit where subdivisions once existed, and where prescription drugs are sold by locals under the cover of grass that has grown waist high. Surveilling targets in rural northern and western Michigan in high-visibility settings, where everyone knows each other and outsiders easily stand out. 

I’ve encountered police officers working side hustles as sex workers; upstanding conservatives secretly selling drugs; strippers working as medical professionals; public school teachers and administrators with drug, alcohol, and sex addictions; and paranoid people hiding in plain sight. 

Most important to my experience is the destruction of my confirmed priors related to growing up in a normal and boring protective suburban bubble with an “American Beauty” aesthetic. Upper- and middle-class Americans often avoid the urban jungles of major cities out of fear of bad local elements and crime. Very common for suburban southeast Michigan residents to have never entered Detroit—with the exception of driving in, or down from I-96, I-75, or I-94 to attend Tigers, Lions, or Red Wings games—only to quickly escape back to the burbs lest they incur an unfortunate entanglement with a local. 

“You’ve never seen a f***ing mile road south of 10” is a quote for a reason. 

There is an underlying fear about the high crime and tough urban landscape that often scares away the naïve Michigan resident. The good block/bad block, “no-go zone” mindset that is rarely mentioned but everyone knows exists. The fact of the matter is that the uneducated underclass of high-crime/low-income areas of Detroit, Flint, or Saginaw are themselves full of fear and paranoia about anything and everything they don’t know or understand. However, that belies another major issue one must cope with when working in said areas: stupid and uneducated people are prone to react to fear and paranoia in illogical and irrational ways. Factor in the mental illness crisis, high drug use, access to weapons, and lack of police and social services in urban cities, and this makes for quite hazardous conditions for an investigator. 

I’ve encountered police officers working side hustles as sex workers; upstanding conservatives secretly selling drugs; strippers working as medical professionals; public school teachers and administrators with drug, alcohol, and sex addictions; and paranoid people hiding in plain sight.

All these years later, having managed to build a career operating discreetly in the shadows of Michigan, I’ve managed to remain unjaded by the unfortunate circumstances, behaviors, and activities that require my skills. I’ve witnessed glimmers of hope in the poorest neighborhoods, incredible acts of kindness from those I’d least expect, and the framework of stressed and fragile society somehow holding together.

From this platform, I’ll be detailing the many interesting, weird, and unusual cases I’ve worked on. The diamonds in the rough and the horrors hiding in plain sight. Comedies that went bad and tragedies with surprise happy endings. I’ll provide observations and descriptions of areas of Michigan most never see. In addition, I’ll share insight into my processes, tactics, and strategies behind my investigations to give readers the perspective of a regular suburban normie working in a world gone mad, just trying to get home at night.

J.Z. Delorean is a writer for Michigan Enjoyer and has been a Metro Detroit-based Professional Investigator for 22 years. Follow him on X @Stainless31.

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