Minerva Studio/Shutterstock.com

It's a thin line between loop hole and fraud. These stories take that right up to the edge of that line, and even cross it, a little bit. Sometimes by ripping off - er - "finding a loophole" in a big company's policies or just taking advantage of poorly thought out contests or really, just straight embezzlement that was impossible to trace. These stories paid of big for they storytellers, but might not be the best way to get ahead in a job or in life. Hopefully they don't land anyone in jail.

SNAFU In His Orders
SNAFU In His Orders

"I spent five years on a US Navy submarine. Every two years, we would do a six-month deployment called Westpac. On my second deployment, I got boondoggled with a few guys - the boat goes out for deployment without us, and we got sent to attend various training schools in Pearl Harbor for the first half of the deployment, then catch a flight to meet the boat. So we watched the boat steam off and caught a flight to Pearl Harbor.

We show up with our orders to check in, but there was some miscommunication, and it turned out office personnel messed up. We aren't enrolled in any of our classes. We don't have barracks or meal chits. Nothing at all. They had no idea we were coming. They give us something called a 'non-availability chit,' which allowed us to stay at any reasonably-priced hotel on the government's dime. So naturally, we found a palatial estate a block away from Waikiki. We show up for muster the next day and the PO more or less just told us 'Yeah, I don't want to see you guys again, ever.' We couldn't get a hold of our boat because it was underwater doing secret things. Once the yeomen got their stuff on straight, they realized that our return plane tickets were already paid for, so they just said fine, we'll do it live.

We were getting a per diem and having our housing covered by the navy, never had to muster for work, and never had to check in anywhere. On top of that, we were still collecting our normal pay and allowances, sea pay for three months. I grew a beard, took some stuff and felt completely out of this world as often as possible. I learned to scuba dive, surfed, fooled around with a bunch of international tourists, went on pub crawls every weekend, hiked, and lots of snorkeling. Woke up on the beach a few times with no recollection of how I got there. Best vacation ever. Thanks, Navy."

Was It All Worth It?

Rawpixel.com/Shutterstock.com

Was It All Worth It?

"I used to travel for work. I lived in Greensboro, NC and worked in Boston. I'd book the same flights every week. Out early Monday morning and back on the 5:30PM flight on Friday night. But the thing is, I knew ahead of time that my return flight would be overbooked. In fact, it was usually so overbooked that they needed as many as six or seven seats. And so they offered money/miles/flights as needed.

Every Friday, I'd wait for them to make the first announcement. Usually a voucher. Pfft. Then the second announcement, probably a slightly larger voucher. Double Pffft. But the third announcement, that's when they started offering the good stuff. I'd take that one, usually at least a round-trip anywhere in the continental US. Sometimes they offered a flight and a voucher, and once or twice they even offered a free trip anywhere in the world. Sweet!

Then they'd book me a guaranteed seat on the next flight, which was never overbooked anyway. The best part was that got on the same connecting flight as I would have if I had been on the 5:30PM flight out of Boston. I didn't do it that way to scam them. It was the only connection available for either flight.

I took that route 45-50 weeks a year for two whole years. I lost count of of how many vouchers and free round trip tickets I accumulated. I even got calls from the frequent flier miles rep, telling me that I was 'abusing the system' and that if I persisted I would have my miles taken away. I figured, what the heck? I earned maybe two free trips a year with miles. That was peanuts compared to what I got by simply taking advantage of their weekly kindness. They never did take away my miles. It all ended about a month before my Boston job was over. One Friday, the gate agent announced that anyone who wanted a free round trip ticket in return for them giving up their seat should see her at the podium and then she followed it up by looking at me and saying, 'but not you.'

The fact that I purchased the earlier flight knowing full well that it would be overbooked was seen as gaming the system. I was getting on the same hub-to-destination flight regardless of whether I departed Boston-Logan at 5:30 or 7:30. I was also told that my shenanigans caused extra work for nearly their entire staff, from dispatchers to gate agents to flight crews. True, someone else would have caused the same amount of grief, but it didn't seem fair to them that I should be able to deliberately do so AND get rewarded for it.

I worked in Boston as a consultant for a large financial firm. The systems I worked on were critical to the business, so they preferred that I be on-site when working. Not only that, I had to be within 15min travel time in case a system had a problem- so I had to stay at a downtown Boston hotel. Price wasn't an issue. I was staying in $400/night rooms at the Marriott Longwharf. I racked up something like 1.6 Million Marriott points, which I redeemed to pay for vacations in Hawaii (once) and London (three times). With airline miles, the Marriott points paid for hotel, flights, and auto rental (in Hawaii) for my wife & two boys. I worked it out once. Between vouchers and various points, I raked in over $100K in perks.

My employer paid for all of the Boston travel. But of course, the real cost wasn't monetary- I paid for all those perks and points with bedtime stories not read, first steps not seen, and nights not spent with my wife."

Blowing Smoke
Blowing Smoke

"I worked in a call center during college, soliciting donations for a campus Alumni Association. Our main performance measure was the number of donations solicited PER CONTACT. If the person didn't answer or hung up immediately, it didn't count against you.

I discovered a bug where, if I blew into the microphone just as the phone started to ring, it would register in the computer system as a no-answer and dial the next number.

I rode this out for several months before I got tired of blowing my microphone for 8 hours a day and quit."

Ripping Off The Bank
Ripping Off The Bank

"I used to work at a small town bank with an ancient computer system. We had a small stash of Canadian currency that we would occasionally exchange for customers free of charge. To do this, we looked up the current exchange rate and used our teller software to give us the value of CAD to USD or vice versa. I found out one day that this exchange rate NEVER updated and was stuck at 0.72 CAD to every 1 USD. This was back when the USD was lower in value than the CAD.

Being the enterprising individual that I was, I exchanged all of my cash (not much at the time, I was 16) for CAD with the excuse that I was going there over the weekend. Went to a bank down the street and traded that in for an easy 50% gain or something like that. I did this over and over for at least a year until they finally fixed the issue with the computer."

A Free Sandwich And Some Chips
A Free Sandwich And Some Chips

"I worked at a sandwich shop when I was a young woman. We were allowed ONE free sandwich for the ENTIRETY of our employment there. Yup. It would be one free sandwich for the whole 5 years I worked there. Being an endless pit of hunger that most 16-year-olds are, I was determined to get as many free sandwiches as possible.

If someone called in a phone order and never picked it up, the sandwich was fair game for employees after an hour. So I would text my friends to call in the sandwich I wanted and then never pick it up. Everyday I got free sandwiches. It was amazing. If I didn't eat it, I would bring it to school the next day and sell it.

If the chips fell on the floor when restocking, we couldn't sell them. I've never been so careless in my life."

Not Fit For Human Consumption!
Not Fit For Human Consumption!

"During the Gulf War, we had these pills that we were supposed to take, that would supposedly protect us from nerve gas. As an NCO I was required to have all of my troops take the medication. The medication was even labeled not fit for human consumption.

So I would put a pill in my hand. Hold it out. And then tell someone take it. They would take it from me. Then later when the officers asked me did everyone in your unit take the pill, I would answer yes. Our orders were that everyone has to take one pill a day, not that anyone had to consume the pill. If I was asked however if they consumed the pill, I would have had to have honestly answered no.

I think my commanders knew what I was doing, and that I was living up to the letter of the orders, if not the spirit. All the pills ever did was make people sick, no one wanted to consume it."

Early Internet Meant Free Money
Early Internet Meant Free Money

"A web host that I used to work for had an affiliate program. Employees were encouraged to use it and advertise.

Some customers were nervous about putting their card info into a web site, so they would call in and get an employee to do it. I had shown several of my coworkers my affiliate page, which set a cookie making anyone they registered count for me. It was an accident. I didn't realize, at first. I even reported it to the head of the affiliate program, but I guess the payouts didn't come from his budget, and fixing it would have lowered the stats for the program and I got credit (and payouts!) for a LOT of customers."

Free Phone
Free Phone

"Around 5 years ago, I used to work as a Sales Rep at a cell phone booth. Every new smartphone that would be released, the wireless provider would usually send us a demo unit of that phone with a demo line. The demo line would have unlimited talk, text, and data but would deactivate after 2-3 months. This was so we could show customers how the phone works with all of its features.

One time we got a demo line that didn't expire after the 2-3 months. So my manager at the time told me to use it as my work line. I didn't want to carry two cell phones so I cancelled my personal line and used my work line as my personal too. Fast forward one year later, my manager is transferred to another store and we get a new manager. New manager has no idea about my work/personal line. I left the company 6 months later with my demo line and to this day I still use this demo line. I can upgrade the phone whenever I want but I have to buy new phones for cash, rather than worry about contracts. The talk and text works fine in the US but I am limited to 1 GB of data per month. The line does not seem to work internationally, but I usually use WIFI anyways.

Around 2 years later, my phone got stolen from my car, along with my laptop, hard drive, and tablet. I was utterly devastated, but more for losing my phone line than anything else. After moping around for a few days, I started to think of ideas of how I could possibly get the magical phone line back. I called and texted the phone line non-stop, offering money for just my SIM card back, but no response. I decided to try a different approach. I called my old store I used to work at, pretending to be a customer, I asked for my old manager, but I was told there was a new manager and I got his full name. I called my carrier, remembering the protocol from my working days, pretending to be the new store manager and I gave them our authorization code, which I luckily still remembered.

I told them one of our demo lines was on the fritz and needed to transfer onto a new SIM. They asked for the phone number of the demo line. I give them the number and they say it's some special line that I have to contact some special department for. They transfer me to the special department, I tell the special department dude about the situation and he's like he can definitely do the transfer but only through email requests. So, I have to send him an email request of the transfer through our store email. Oh no! Another dead end, so maybe the magical phone line is gone forever, and looks like I have to pay for a phone line like the rest of you peasants.

But then I had a magical flashback to 5-6 years ago, when I used to work at the wireless store. My then-manager asked me to create a store email for our team to use, for whatever use. I couldn't remember the password of that email, but I did remember I just made a regular gmail account. So I made a new gmail account for my old store and emailed the special department my phone line transfer request onto a new SIM card, under the guise of that store's new manager. The line was transferred within 2 hours and I got my magical phone line back.

I have not had a cell phone bill for over 5 years and counting."

Ripping Off Walmart
Ripping Off Walmart

"Back in 2008, my girlfriend and I were living together and working retail jobs to make ends meet (this was when the recession was first getting started). Gas was $3.50/g and rent was high and making ends meet was a continuous challenge.

I was working at Target at the time, after having recently left Walmart, for the sake of my dignity and sanity. Target (at least back then, and at my store) commonly marked down clearance video games to ridiculously low prices. For about six months, I would buy clearance games at Target for $5-$10 and return them to one of the local Walmarts (where video games were much less often on clearance) for $30-40 in store credit.

That went a long way towards keeping us fed during a very tough financial stretch. Getting a few over on Walmart a little in the process was just icing on the cupcake."

Piling On The Savings
Piling On The Savings

"I worked at RadioShack for about 5 years. We got 50% off ANY RadioShack brand items as an employee. That included cell phone accessories and parts, hard drives, radios, toys, memory cards, and even DIGITAL CAMERAS. Every time you buy something at Radio Shack, we would print this receipt, and if you go online and take a quick survey, it would give you a coupon for an additional 10% off. Then we would get those circular advertisements, which would also contain either coupon or specials.

So I used to regularly get 70-80% off anything I purchased in the store. I got my dad a digital camera, camera stand, case, and a bunch of accessories for it, for around $30 one year. The camera was actually really nice, too. And Black Friday was a gold mine, we got first pick to set aside any items we wanted to purchase ourselves.

The other cool thing is that if the item you buy goes on sale for a cheaper price within 30 days, you can return and get the difference in price back. So in addition to my discounts, I could get cash back if there ended up being a better sale during the next month. Pretty sweet savings on some expensive stuff."

Smoke Up, Johnny
Smoke Up, Johnny

"I used to work at a very popular convenience store chain here in the midwest. This was over 20 years ago, and I used to smoke.

Marlboro Miles. We would stock the single packs from regular cartons, but when the mile program was out, our manager would have us use the 3-pack container that had like double miles on it to stock the single packs. I would then take the container home and cash in the miles. I got two watches (pretty nice ones too, Swiss Army brand,) a huge lumberjack pullover which I still use to this day, a really nice sleeping bag, and various other trinkets.

Marlboro 2: Marlboro had this promotion to buy 3 packs and get 2 free. We had hundreds left over after the promotion was over. The 2 free packs had 'Not For Resale' on them. I was allowed to stock the 3 as singles and take home the 2 free ones. Took home 5 or 6 cartons of Marlboro 100s.

Finally Marlboro 3: Double Bonus: When the Saturday newspaper came out, it was called the 2-Star Edition. Then the Sunday paper would come out, and they called it the 3-Star edition. We always had 2-Star editions leftover, and if I knew there were coupons in there, I would clean out all of the 2-Stars. Coupons counted as cash in our drawers. I could buy Marlboro's with any coupon, the same as cash. And if the Marlboros had manufacturer coupons on the carton, we could stack on top with those. It almost made them free!"

Making Money In His Sleep
Making Money In His Sleep

"I used to work for a delivery company that delivered 24/7. When they were starting up, they paid hourly because there weren't enough deliveries to guarantee a decent salary. So I would take a shift from like 1-7 in the morning, turn on my delivery app, just go to bed and make money while I slept.

No one was ordering food at 4 in the morning. There were no deliveries to perform at all."

Cheating One While Working For Another
Cheating One While Working For Another

"I am an Uber Driver and last year, Uber cut their rates and it hurt really bad. What was once a decent job became one where I was making below minimum wage if I was lucky. I wanted revenge. So I used a little hack to collect money from them...

There was no way to request yourself as a driver (without getting caught), but it was easy to use another phone with another profile to request yourself. Since Uber had so many drivers and so few employees to monitor shenanigans, I figured I would fly under the radar. So I created a fake passenger account and would request myself to meet their hourly fare guarantees. Uber always runs these 'guarantees' after the price cuts to get drivers used to driving for less money. Since the app saw that I was logged in for the hours, I would get paid Uber's guarantees while I went out and did Lyft rides.

At the end of it, I ripped Uber off for about $6,000 and quit. I can tell people that Uber literally paid me to go drive for Lyft. It felt so good to get my revenge from a company that had done everything in its power to completely ruin the lives of its drivers. Every driver I knew was suffering after the cuts.

Fast forward one year, and they cut their rates once again. I don't know how they survive. Please tip your driver, they can't admit that they are suffering because it leads to low ratings. I assure you they are."

Scamming The Credit Companies

Dusan Petkovic/Shutterstock.com

Scamming The Credit Companies

"I work with cell phones and we do credit checks on people activating new lines. This sucks for me because some people have bad credit. However, I'm a genius. Basically if someone fails a credit check, they have to put down a ridiculous deposit, so this is how I bypass the credit check.

A. When entering the driver's license, get a couple digits wrong. (This won't show any credit)

B. Find the most expensive neighborhood in town, set customer up with a postal code of that neighborhood. (Postal codes affect your credit, now the customer has positive credit)

C. Sign the customer up on the cheapest device in store. (Value of device affects the deposit amount)

D. Return the device and sell them the device that they initially wanted. (Since we set up the account we don't need to run credit again)."

Dialing For Dollars
Dialing For Dollars

"I worked in a call center, it was really horrible and management micromanaged hardcore, so basically any time you were not in a 'talking' status unless it was for breaks or lunch, you were getting yelled at and write-ups threatened. They basically wanted us to constantly be on a new call, regardless if the previous customers issue was even fully handled.

I figured out that you could dial your own extension, and it would display talking for roughly 5 minutes before kicking you back to whatever status you initiated the call from. Also these self-calls did not get reported in the reports or in the stats.

So for about one and a half years, I would come into the office, and do literally nothing the entire day except dial my own extension, and take a call every now and again to make my monthly numbers. I would take smoke breaks whenever I felt like it, restroom breaks, coffee breaks, etc. I would spend probably half my shift not anywhere near my desk, just messing around for five minute intervals at a time.

They never caught it, and I left for different reasons, but for one and a half years I got paid to stare at a screen and look busy."

Scamming A TV
Scamming A TV

"As a teenager, I used to deliver the local newspaper. Part of the job entailed receiving piles of pamphlets (flyers) that you needed to slip in to the newspaper before you folded/rolled them for delivery.

Anyway, every year we have a local show/carnival that came to town. You know, the kind with rides, animals and entertainment. In the week following up to the show, I had to 'deliver' a pamphlet that was actually an entry to a raffle to win a TV. The entry barrel was at the show, and drawn on the last day.

Needless to say, nobody received their raffle entries that week, but I received a TV. Also, my hand hurt from writing."

Subscribe to the RateMyJob Newsletter!

Get hand-picked stories just like these delivered straight to your inbox!

Cookie Settings