What's the shadiest job you've ever worked?

I was 17 at the time and got a job as a bouncer at a pretty seedy place in a very small village out in the countryside (I was there for the summer working at a fish factory and figured I might as well make som extra bucks). The guy whose job I got had been seriously beat up by some Reykjavik crackheads, since apparently he owed them some money.

I, however, loved the job :slight_smile: Got to pull a lot of birds and made some extra cash under the table.

Nothing to add to this, but I absolutely LOVE your writing style wolf-alice.

I worked for one of the larger payday/short-term loan companies. I can’t even remember the name of it, but it was a national chain.

I was the asst. mgr. but the actual mgr was such a loser that when customers came in with problems they’d ask to speak to me, because I looked that much more presentable. We were encouraged to try to flip the loans, that is, if someone was behind we didn’t want them to get caught up. No, we wanted to let them take out another loan to pay off the previous one, and keep getting regular cash flow from them.

The guy that was the branch manager was constantly making shady deals for loans for people to buy cars he’d bought and fixed up. Many of whom didn’t even meet the meager credit. Did I mention many of those cars were repos from people who had finally gotten to the point we took their collateral?

After about 3 months, I left. I’d put in for vacation, and literally the day before I was going to leave, the manager tells me, 'You can’t take vacation. I need that time off for mumbledmumble." I tried to call the district manager and he backed the manager. Being fresh out of college, and having a single bill consisting of a 120/month car payment, I said, ‘Okay’. I let the manager leave on his impromptu vacation that afternoon. On my way out town the next morning I dropped off my Effective Immediately resignation letter. The phone call when I got back was so damn satisfying.

Two weeks later, I was working for an actual financial institution. One of the best calls I ever made.

When I was 13 I worked under the table as a door-to-door newspaper subscription salesman. Basically, what was going on, is I was doing the job of another guy, the one I worked for, who drove me around neighborhoods in a piece of shit Toyota Tercel. I guess he figured a kid knocking on everyone’s door stood less of a chance of being shot than he did, so it’d be more profitable for a kid to be doing the job. It wasn’t all that pleasant for myself either though. I got to meet a fair share of ass holes, usually every 10 doors I went to.

My good friend also did the same thing, except he was a little smarter than I was. FTR, I didn’t find this out until a couple of years ago, but had I known I’d probably have done this. While he went door to door selling the subscriptions he’d also conclude with “Our Middle school is also having a fundraiser for an upcoming field trip and we only ask $1 from you” or something along those lines. He did quite well, most times getting more than a dollar. The money taken in from this little scheme took in 10x more profit than his pay.

Ahh… Another job I remember now. I worked the hot dog stand outside of a nightclub for about 2 weeks once. God, it was horrible. As many chicks as I talked to, actually picking them up was far from possible. The $120-$150 a night wasn’t so bad though so that equated to my misery.

My first “real” job when turning 15 after paper route was a bag/cart/stock boy at a grocery store.
The store manager who interviewed and hired me was kind of creepy but I really wanted this job since it was a real hourly wage job.
On my second day of work I came in to find that manager was fired and 9 of the 12 boy crew no longer worked there.
The new manager asked me if I could work “a lot” of hours till he hired a replacement crew.
Turns out the creepy manager that hired me was having “pool parties” at his house with the underage crew, giving them alcohol, and molesting them. One of the kids blew the whistle on him.
So I dodged that bullet and as an added bonus had immediate seniority over the new crew after only being there a week.

For about 5 months, my programming job was for a company which pretty much just made dialers for porn bulletin boards. I was uncomfortable enough about that, but worse was the fact that if our program detected that the user left the site he had logged on to, it automatically dialed another number to connect to a similar board.

Worst I’ve ever done, I guess, is being a spammer of sorts.

It was all officially “Opt-in E-mail services”. We had a massive farm of servers that sent bulk e-mail very quickly. We, over time, had to develop throttles in the farm for certain address sets because we were fully capable of crashing a smaller ISP (and once a fairly major corporation and a minor island nation). We had contracts with lots of different companies to send newsletters and other subscription-based emails. We usually used listings supplied by the companies for this and our contracts said it all had to be opt-in, verified, etc. We, in the early days, would even (rarely) drop a contract due to abuse of these rules.

Over time, though, as times got worse, we started enforcing the rules less and less. I know that we sent bulk mailings that were 60% bounced. This is what we called a “dirty list” and usually indicated a harvested set of email addresses rather than a 5-10% rate that a good clean list would have.

Over time, I think we lost our moral compass in favor of trying to keep the doors open. FWIW, unsubscription links really worked and we really did have good intentions.

The company is out of business now.

Telemarketer for a home improvement company, for about a week.

Door-to-door enclycopedia sales, also for about a week.

When I was 17, I was in the middle of hitchhiking across country (another story, rather long and quite amusing!) and was picked up by a guy named “T” somewhere outside of Little Rock. He asked where I was going and I gave him my standard “I dunno, that way!” answer. The real answer was “Anywhere but back home” but I never gave that one. He offered me a job on the spot selling squirt bottle cleaner door-to-door. This stuff was made in the back of a semi, in a 55 gallon drum, with a trolling motor to stir it up, out of citric acid and water (mostly). We sold the stuff for $22 a bottle, in 1984. We were “allowed” to do special deals, like 3 for $44, 5 for $65 and so on. Basically we would sell as many as we could in a place and pocket as much as we could! My pay was $7 a day plus my hotel room. I did it for 4 weeks in Dallas, 4 in Houston and 4 in San Antonio. Lots of fun stories in those weeks!! During out last week in Dallas, we returned to the hotel to find the FBI & ATF there to take “T” into custody. Apparently he had some kind of federal firearms violations on his record!

For a year or so when I was 13, I put together 4,000 copies of the Sunday NY Times in a garage in Oceanside NY. 5 sections on Friday night, 5 on Saturday night. $40 a week for A LOT of hard, dirty work. Obviously, no W-2!!

For 3 days in LA, I did that “Hey mister, we’re selling a bunch of extra stuff we got, they sent us a double shipment of briefcases!!” gig. I’m surprised any of that crap held together long enough to get sold.

Most people would assume working as a collector and courier for a bookie would be mine. It wasn’t even close. The bookie I worked for was an honest businessman who just happened to have chosen an illegal profession. He even prevented me from actually getting rough with deadbeats, since adding a doctor’s bill to their list of woes wouldn’t actually get him paid faster. Made perfect sense to me.

I’d have to say the shadiest was working as head of security for a biker-owned strip joint. Of course they used it as a laundry for their drug sales, but it was relatively decent for a dive strip joint, and the security staff was paid well. I quit, turned the manager in to the police and offered to testify when I found out they were hiring underage and turning some of the girls out as part of an outcall prostitution ring. I found out when the manager asked me to drive/cover one of the girls who was going on her first trick. The guy they regularly used had gotten arrested for something minor and wasn’t available. The manager didn’t give me much detail about why I was driving her, but talking to the girl get me all the info I could have possibly wanted before we were halfway down the block. She told me she’d gotten upside down on what she owed from buying drugs through the manager and was being forced to work off her debt.

When the cops raided the joint, they found more than enough evidence that I didn’t need to testify or even have my name in any way associated with the case; so that was nice.

Lulz

I’ve had a few in my much younger days.

I sold religious signs, little 8 x 10 cardboards with a bible verse and glitter on it, door to door, they cost about $.05 and I got as much as $2.50 for them. I probably sold 600 in one year in 1967, I was 14.

I also sold a miracle salve that cured damn near anything for 50 cents a 2 oz can. Basically bees wax and turpentine.

The worst, was a roach ridder, that we made in the kitchen out of candle wax and green food dye, sometimes we would get a complaint and we would give them another one for free but sometimes sold them the “deluxe” version for a little bit more. It was bigger.

These were all jobs for my uncles that used my youth and straight arrow looks as sales assets.

The really shady one, from Uncle George, was when he hired me to ride around in his old caddy to help empty soda vending machines, he had keys but I found out later he had stolen them from the seat of a pepsi truck and didn’t have the rights to any of them.

When I turned 18 I left home.

I worked in the back rooms (cleaner, prepper, boxer, etc) of a major supermarket chain. The one I worked at didn’t want to pay the expense of liquid waste removal or recycling, and routinely had me pour their waste (oil from cookers, degreaser from cleaning, etc) down the storm drains after-hours. When I first complained, it got bumped up the chain until the district owner/manager himself personally told me to keep using the storm drains.

When I was 18, I had a summer job selling ice cream from a truck. Fun job, actually, but after about six weeks, I showed up for work and the place was swarming with cops. Turns out I was one of three employees that weren’t selling dope along with bomb pops.

In the eighties, I worked as a PC technician for a very shady company run by “squirrel” Scientologists.

I spent quite a bit of time replacing clock-speed ocillators on motherboards with faster ones, so that lower-rated CPUs would run faster and sell for more. (Of course, they’d burn out faster, too.)

Me and another tech lived on the premises (not zoned for that) and were frequently paid in equipment (that were probably never actually paid for.)

That job ended when the sherrif’s department showed up and hauled everything (including my stuff) away, and I spent a few nights in an SRO in Vancouver’s notorious Downtown East Side, where for the second time in as many days I had uniformed men bust into my room - this time because someone had been shot in the hotel, and they were looking for the shooter.

Good times.

For about a year in college and for a little while after graduating, I sold popcorn, hotdogs and soda for a guy in town. The business was legit in that everyone got what they paid for, and they only paid standard killer overcharging you get when buying from a cart in a place with no other options. What made it shady is that he paid in cash from the all-cash take, and he was paranoid about the IRS. He also had stories ready for the health inspectors, because he didn’t want to have to bother with squeeze bottles for condiments. I just gave up and never bothered mentioning the income to the IRS. These things were why we ended up quitting.

I had a roommate who responded to a job ad and was taken around in a van selling “overstocked speakers”. He quit that day.

At that same house, a previous roommate I never met had been taking flyers that he was paid to distribute to houses, and just leaving them on the side of the house. They were never delivered.

WTF is a bomb pop?

Also commonly called “Rocket Pops.” You know, coloured ice on a stick, red on top, white in the middle, blue on the bottom.

Bomb Pop

For almost 20 years* now, I’ve been in the business of obtaining subversive literature for and delivering same to children.

Just the other day, I helped a minor find a copy of Animal Farm.

*Minus 4-1/2 when I worked for the real evil-doers. Investment bankers.