The second time I ripped off a wounded soldier, I knew I had to quit the car sales business for good.

It was a difficult time in my life but I was making amazing money for a 23-year-old without a college degree. I was working at a new car dealership for a major brand in a prosperous area. I had also done a brief stint at a luxury car brand in the same area, but returned to the first dealership when the high cost but slow build sales didn’t happen fast enough.

The pace picked right back up when I got back to my roots at the first dealership. But I also started to hate myself and those around me. 

Like the majority of car salesmen, I was paid 100 percent by commission. And for my commission on each car to be more than a pittance I would need a customer to pay way more than what the car was worth.

All that leads to an inescapable fact: for me to have a good day it meant someone else was having a bad day. Because they had just been massively-overcharged for a car.

Some background: I spent much of my teenage years and twenties obsessed with hustling. I've been a professional gambler, magician, bartender and a part of all manner of moneymaking schemes. Including, of course, automotive sales.

Really, the only job I’ve ever regretted was car sales.

I will say car sales is an amazing “school of hard knocks.” It truly is a life teacher but I don’t think anyone should do it for more than three months. Which means I did it for about a year too long.

At the time, I was proud to say I fit in surprisingly well. I was a young bohemian-ish Jew surrounded by old Anglo-Irish men with political views ranging from Republican to slightly to the right of Mussolini. 

It was definitely surprising. 

Did I mention I was making great money? Customers who were rightfully wary of the checkered jacket old-timers felt more comfortable with a young guy, I guess.

For awhile I fooled myself thinking I was a Bob Dylan-type working class hero.

I fancied myself an intellectual or journalist living a noble blue collar life. And then I realized there was nothing journalistic or noble about it. I really was just a jerk in a golf shirt, working 10-hour days and 70-hour weeks. Picking up a six-pack on the way home to share with my cat, while my resentful girlfriend with a standard 9 to 5 job was already long asleep. 

I started feeling bad very soon after I started. Sometimes it would be because I sold an overpriced car to someone like me. A young person just starting to make their way in the world. Someone who is really excited to finally be earning a paycheck. Someone who is ready to embrace the icon of middle class success that is a brand new sedan.

I looked for a conscience in the dealership, someone who could tell me that these sales are a balance and a salesman deserves nice commission for providing excellent service. But all I found was the same bloodthirsty “us versus them” mentality.

In fact the few times I mentioned my reservations to a manager I was threatened with being fired. If I didn’t take a customer for all they were worth, I was “holding back money from my employer.”

The more I look back at it, the more I realize how much wealth is destroyed by a monthly car payment.

I mean how much can you really invest and save with a $400 anchor around your neck? Not to mention maintenance, insurance and gas.
Especially amongst the specific groups that the salesmen targeted. Those included:

People who looked like they were from poor communities. Salesmen assumed they would have bad credit score and they could make a nice commission on the finance side of things.

Older people. If they were less internet-savvy they would know less about a fair price, and again, would be easier to rip off.

Women. It was assumed that they wouldn’t care enough to haggle and they would just take the first (terrible) prices to get out of there quickly. 

But the favorite group at my dealership was soldiers.

The dealership was located near an army base and the dealership loved selling cars to military personnel, because they often didn't understand finance too well (having lived on army bases most of their adult lives) and were easy to overcharge.

I sold a fully-loaded sedan to a specific soldier for way more then he should have paid. He was a really nice guy but my manager locked him into the price before I could really think.

The guy came back six months later and said he needed an SUV because he was injured overseas and couldn't get into a sedan with his bad leg. We end up selling him a base model SUV that was actually cheaper than his sedan. But we told him "Great news, we can swap you in to this SUV and your monthly payment will only go up $100 a month."

It’s actually a little difficult for me to type that up, to think about how I helped cost a wounded veteran thousands of dollars, all because he was a bad negotiator.

I can say with ease that it was the last straw.

I got out of the dealership the next week and embarked on an adventure that involved a lot of gambling, traveling and occasionally paying my bills through charm and sheer willpower.

The years after the car dealership were uneven and had some serious low points. Though I’m pleased to say that the only person who faced financial hardship as a result of any of my decisions after that - was myself.

I'm thrilled to put those skills and interests to work in a much safer, happier ways as a writer and marketing guy. 
(I’m also happy to say I no longer drive a car.) But I still want to shed light and help people avoid getting hustled. That’s why I’m writing articles like this and that’s why I answer questions on Twitter or my website.