I Did Business With Insane People

4 Stories of Psychopathy, Ego, and Ambition

The word insane is drastically overused for everything from mild moodiness and irritability to emotional changes. That's not what this article is about; these are four stories of times I did business with people who were deeply unwell psychologically.

Sometimes, I ask myself whether it's a degree of insanity within myself that has attracted these people and circumstances or whether it's just a matter of dumb luck that I've been quite intimately ensconced in business four separate times with people varying from unstable addicts to genuinely demented. I'm leaning more toward the former than the latter.

In addition to being entertaining, I hope that these stories can educate you on how to identify the tale-tale signs of insanity in the charming, persuasive people you are considering doing business with.

David

David was my best friend for four years, towards the end of that time it became increasingly evident that he was a non-violent, high-functioning psychopath.

David was on the path to become a doctor, he was incredibly hard-working and more devoted to his studies than any other college student I've ever known. David, at any given time, had at least one woman intensely in love with him. He had to pay for abortions at least three times, he told me. To this day, he remains the most charming person I have ever met.

David partied; he loved nightclubs, bottle service, cocaine, and occasionally smoking crystal meth. He had a contagious ability to energize any room. David had a disturbing amount of confidence in his ability to drive drunk - he would, barely able to walk, drive his truck aggressively all the way across town. I remember watching David getting caught with cocaine in a nightclub bathroom and then proceeding to successfully convince the police that it was not his. He had an uncanny talent for getting drugs for free from gay guys. I remember several nights, going to hang out in seedy apartments so he could score drugs for free.

The only other passion that matched his appetite for intoxicants was his religiosity. He came from an intensely religious Mormon family (who I knew well; they were some of the classiest, most generous people I've ever known). Sometimes, in a drunken fervor, he would explain to me how he was one day going to become a god of his own earth (this is part of the Mormon religion).

When I decided to enter the entertainment business at age 21 by organizing my first concert, David was my partner. The last time I saw David, he actually walked in on me having sex with a woman I had just met who had been admiring the brand-new Maserati I was driving.

Most insane moment

David once stole and took on a joyride a tuner fast and furious sports car during a house party. When he returned, the car's owner, drunk on tequila, ripped him out of the driver's seat and beat him up. David then hid in a room in the house with some girls while I tried to convince the car's owner not to kill him.

Ed

A former banker, supposedly worth $12 million, diagnosed with dissociative identity disorder (aka multiple personality syndrome), was the financier of an entertainment start-up I worked for. Early in my career in the entertainment business, a friend called me and told me excitedly that he had an investor who would finance whatever we wanted to do: concerts, nightclubs, clothing lines, football stadium events, etc.

They hired me as the second employee of the company and paid me $35/hourly to organize event marketing strategies and network with potential strategic partners (aka party). Ed had an ugly codependent relationship with my friend, the CEO of the start-up, who gave Ed's darker sides continuous excuses to blow his money frivolously. One week, they showed up with an Escalade (on 22-inch chrome rims). The next week, a brand new Mercedes-Benz SLK350, and then a new Maserati GranTurismo from Ferrari of Denver. They also sent me on all-expense-paid trips to Scottsdale and Cancun, Mexico.

Ed took medication and saw a shrink to deal with his demons. What seemed to trigger Ed's other personalities most consistently was drinking alcohol. One was a woman, one was gay, and one was a reckless young man who just wanted to get drunk and laid. His personalities had a clever method for communicating with each other; they would call his cell phone's voicemail and leave messages.

After several months of this spending, in an uncommon display of maturity and sobriety for a 22-year-old living like a rockstar, I wrote a formal letter to Ed and the CEO stating my serious concern with the spending before the business had made a cent of profit. Their response was a demotion, eventually, we ended up throwing a single event at the Denver Broncos football stadium, it lost probably $15,000 and I resigned.

Most insane moment

After a night of drinking, Ed's most malignant personality emerged while he was driving the company car, a black 2-seater Mercedes convertible, with the CEO. The personality announced to the CEO that he was going to kill him. He then proceeded to run a red light doing +50 miles-per-hour and t-boned a sedan. Amazingly, he didn't kill anyone that day, but he did destroy an almost $70,000 car.

William

A mild-mannered tech start-up founder client of mine with a dark past. Early in my career operating a web strategy firm, I met a man with a great idea for an eCommerce marketplace. I agreed to develop his online platform in exchange for a four-figure payment and a piece of equity in his start-up.

In the beginning, he came across as smart and easy to deal with. He told me he had recently gone through a tough divorce. As is common in the start-up development world, we ran into all kinds of technical challenges and delays. We actually ended up having to sue a 3rd party vendor. I remember picking William up at his dad's place for a long, awkward ride to the courthouse. About a year into the partnership, William had significantly changed the project scope of what he wanted the website to do, so he released me from my development responsibilities and had me focus on business development of future customers of the service, which I did, building a list of over 100 potential customers.

I had a base of small business clients ready to use the service, but William was lost in a perpetual cycle of second-guessing and redesigning the technical side of things. I urged William to simplify the development side so we could begin serving the clients and generating cash flow. He started making me all kinds of promises about increasing my equity, infusions of investment capital, licensing the business model in other countries, etc.

He was kind of a weird guy; he never went out to socialize or date, he lived with his dad, and he was singularly focused on his start-up. Out of the blue, one day, a woman on Facebook wrote to me, informing me of his history of domestic violence. Apparently, they had a kid together a long time ago, and he had done a bunch of weird stuff to her mother. She provided me with police and court records to verify everything. Then I did something I hadn't yet done up to this point: I Google searched my client, William. The top result for his name was a news story identifying him as the "Craigslist Stalker of Boulder," and there were other news stories about his weird and sometimes violent past.

Four years later, his website isn't even up; no investment capital ever arrived, and the customers I gathered were never served. In business, William wasted a huge amount of my time, but I'm mostly just disappointed that this smart guy, with such a good idea, worked so hard and never made it happen. From this episode, I learned that a great idea counts for nothing; even a great idea plus hard work is pretty useless without a clear way to scale into cash flow. I also learned to Google search the people I'm considering doing business with. Finally and probably most importantly, I learned that the kind of character that mistreats women is the kind of broken person who will never produce consistent results in business.

Patrick

My business partner of a few years displayed frequent psychopathic tendencies. Patrick should have had a revolving door installed on his bedroom; he was a classic womanizer. As opposed to embracing polyamory, he always had a girlfriend who was committed to him that he would cheat on at every opportunity. Patrick had a need for speed; he was passionate about fast, performance cars, and he always had some kind of tuned-up car that he drove like a demon.

Patrick had many redeeming qualities that made him a good partner. Any business I introduced him to, he would learn fast and do better than me. He was a master networker; he would find ways to catch the attention of people more successful than us and land them as clients. He had high standards for the business and the quality of the products and services we sold. As partners, he always made more money for the business than I did.

Towards the end of our business partnership, we became roommates for a short time, and he was abusive to me, his girlfriend, and our pets. I was astounded by his ability to not understand how his insanity affected those closest to him. The last time I saw him, we took a brand new BMW on a wild test drive through the foothills of Colorado. Patrick's fast living and vices eventually caught up with him, and he died in 2016.

Most insane moment

Late one night, after seeing one of our favorite DJs at a nightclub, we got into an extended high-speed car chase. Patrick was drunk, driving his racecar of a Honda Accord. He pulled into a restricted parking lot near the nightclub, and security guards approached the car. But as opposed to apologizing, he screeched out of the parking lot, as he did the security guards bashed out two of the windows of the car with their batons. He clipped the fender of another car as he tore out of the parking lot, attracting the attention of two vigilantes in a white Jeep, who took up hot pursuit of us. We raced around the downtown area, running red lights, and eventually got on the highway. Usually, one of Patrick's cars could easily outrun a Jeep, but the transmission of his Accord was going out as a result of his high-speed habits. The guys in the Jeep kept trying to run us off the road. They were not cops; they were people (probably friends of the driver of the car we had hit and run) who wanted to do bad things to us. About 20 miles north of Denver, we finally lost them by taking an offramp and killing our lights simultaneously.

The entrepreneur must dance with risk.

That's the game we signed up for. And "in the light of risk, all Earthly colors meet heavenly flame" (to paraphrase my favorite line from my favorite novel), but as I would learn, doing business with insane people or those lacking in character was not a risk worth taking. There are all sorts of interesting risks you can take in business, but dealing with those who exhibit a bunch of mental health red flags should not be one of them.