April 28, 2022 | Eul Basa

These Evil Geniuses Exploited Huge Loopholes

Let's be real: Rules were made to be broken. This means that when we find a loophole, we better take advantage of it. These people have found loopholes in their academics, finances, jobs, and even food. From extreme couponing to earning free gas, read along as these people share their favorite loopholes they’ve ever exploited.

1. The Fruit Loopholes

Back in college, we found a loophole with coupons at Kroger for General Mills cereal. If you bought four boxes of cereal, each box was a dollar. But, if you did the self checkout, you would be printed out a coupon for four dollars off your next purchase. We soon went mad with power. We used the loophole to buy about 300 boxes of cereal.

We only spent 12 dollars on all of it. We would've spent less, but we had to go to another Kroger once the manager got wind of us. We kept around 20 boxes for ourselves and donated the rest to the local food bank. They were so excited when we showed up with three vehicles full of cereal. It was totally worth the 12 dollars and all the time it took.


2. Contacts Through College

I worked in a call center during college. Our main performance measure was the number of donations solicited per contact. So if the person didn't answer or they 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 eight hours a day and quit.


3. Replaced And Refunded

I bought a terrible Sega Genesis game. I think it was some flight simulation, which was the crappiest game I ever played. So, I took it back to K-Mart and was told, "No refunds for open games. We can give you a replacement for the same one, if it’s broken." Annoyed that I couldn't get my money back, I came up with an ingenious plan.

I said it was broken and went for the replacement. They then handed me a new copy of the game and my original receipt. I left and came back an hour later, stating, "I want a refund for this game, here is my receipt and unopened game." I got my money back and went and bought a different horrible Genesis game. Maybe the smartest thing I've ever done.


4. Racking Up The Reading

In elementary school, we had the Accelerated Reading (AR) program. You would read a book, take a test on the computer, and be awarded points based on how well you did. At the end of the year, you could buy things at the bookstore with the points you accumulated. I had just finished reading Harry Potter and the Prisoner of Azkaban and got a perfect score on the test.

The computer was only supposed to allow you to take the test once, but I figured out you could take that specific Harry Potter book unlimited times. I racked up so many points and was never found out.


5. Two Questions For Two Programs

Back when Vista and Office 2007 launched, Microsoft did an online event where you watched some dull-as-dishwater presentations by their evangelists. For each product, there was a simple two question/answer quiz at the end that if you got correct and put in your response quickly enough, you got a free, shrink wrapped copy of the Ultimate version of Vista and the Professional version of Office.

It was implied in the blurb that you could only win one or the other, but I knew just how to game the system. It turned out there was no mechanism in the system or rule in the terms and conditions that prevented you from entering both competitions. So, I did win both and so did many others. I got a free copy of Vista Ultimate and Office 2007 Pro.


6. All Of The Trade-Ins

Last summer, I went up to Northern Michigan with a buddy of mine. He's got a nice summer cabin in a small town called Oscoda. It's a nice little place, with beautiful lake beaches and other fun outdoorsy stuff, if that's your thing. But, there's not an awful lot to do up there otherwise. We walked from his cabin into the town, and walked into a closing K-Mart.

I walked over to the electronics aisle, hoping to find some bargains on video games. Unfortunately, they only had one horrible game: Putty Squad for PS4, and they had an awful lot of copies. I checked the price. They were on clearance for $14, but were marked at an additional 90% off, bringing the price down to a measly $1.40 each.

I did the sensible thing that anyone else would've done and bought 20 copies, even though I had no interest in ever playing any of them nor did I own a PS4. After a weird look from the cashier, he removed the security labels from the games and sent me on my merry way with a bag full of sealed games I spent under $30 for. But I knew just what to do.

I brought them home with me and traded them into GameStop one by one every time I went, getting approximately $7 per copy in store credit. I traded in such a high volume of copies, though, that I was banned from trading in games at GameStop! Fortunately, it's a system-issued temporary ban to prevent people from loading off stolen goods.

I just traded in my last copy last weekend when they were doing a 50% bonus trade-in credit promotion, and got $10 of in-store credit. I made something like $150 in store credit total off of $28 plus tax. I consider this a victory and it makes for a funny story to tell.


7. SoBe And Soda

At my local movie theater, you could get a small drink for $2.50 or a large drink for $3.50, and a large drink allows you to get unlimited refills. As another option, you could get a SoBe tea for $2.50. But, they didn't give you the SoBe bottle because they wanted to avoid any broken glass incidents. So, they poured the SoBe into the large cup. Boom, I got unlimited large drink refills. I saved several dollars that way.


8. Back And Forth

By accident, I found a gumball machine that if you turned the dial really slowly, it would drop the gumball. Then, you could dial it back just enough so the next gumball would drop into the tumbler bits, then slowly dial forward again until another drops, and so on. I got about 20 of them and stopped when I realized that I really didn't want to chew that much cheap gum.


9. One Man’s Trash

In the 80s, Chuck E Cheese's didn't shred the tickets you get out of their games and used to buy toys and candy. This turned into the best thing in my life. My friends and I were biking one day behind a strip mall practicing our wheelies and jumps. We saw a worker throwing a garbage bag of tickets into the dumpster behind Chuck E Cheese.

We grabbed it and then started circling back about once a week. There were garbage bags and garbage bags full of tickets. We were doing so well, one of my friends' parents got in on it. She would take the minivan behind there and have her kids load up. This is probably why tickets are now shredded. I think I still have a huge stockpile of frisbees and stuffed animals in my parents' attic somewhere.


10. An Ongoing Discount

My college didn't put any dates on our Student IDs. There was no graduation year, no expiration date, nothing. As a result, I kept using it to get student discounts for YEARS after I graduated, mostly the 15% off J. Crew discount.


11. The Neverending Demo

Around five years ago, I used to work as a Sales Rep at a cell phone booth. For 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 two or three 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 typically two or three 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 canceled my personal line and used my work line as my personal one, too. Fast forward to one year later, and the real loophole comes in.

My manager is transferred to another store and we get a new manager.  The new manager has no idea about my work/personal line. I left the company six months later with my demo line and to this day, I still use this demo line. I have not had a cell phone bill for over five years and counting.


12. Mashing The Competition

I was in a trivia bowl type of competition in college. As soon as the announcer began asking the question, you could buzz in and answer. If you got the question wrong, you lost no points and the question was skipped. My team answered the first question correctly and proceeded to mash the buzzer for the rest of the round, effectively blocking out all the other questions. We won the round with a final score of one point.


13. Sad Day For Soda

When vending machines first started accepting credit cards, you could swipe your card, select a drink, and when the little drink pod started moving to collect your drink, you could cancel. The cancel button would stop the card transaction, but not the machine, so you could get free drinks. It was a sad day when it stopped working.


14. Coming To Collect

Back when Hollywood Video was around, they would guarantee new releases to be in stock. If they rented out all of their copies in the store, they would give you a voucher for a free rental. I figured out a way to take full advantage of this. I was in college at the time and would go into the store near my college campus at around 10 on a Friday night.

There was simply no way for them to have any copies left by that time, so I would collect whichever vouchers were available. I would do this continuously.


15. Same Day Copay

My son attends speech and occupational therapy every week. Usually, it is a $35 copay for each therapy, but if I do them on the same day I only have to pay the copay once. Saves me about $140 a month!


16. A Different Frozen Screen

Back in the day of flip phones, I had a Razr that I loved. I learned that if I dipped the screen in water and then put it in the freezer, the screen would stop working, but everything else continued to work fine. The sticker behind the battery was never touched and didn't change color. I would do this whenever my phone got scratched, and then call them saying my screen stopped working.

I would send it back and they would send me a new one for free. I did it about five times. I discovered this because I left it out in the snow by accident once. It was awesome.


17. A Real Jerk Move

I used to play a lot of Backgammon on Yahoo Games and some people were real jerks when losing. Most commonly, they'd stall the game by taking the maximum of five minutes per move, hoping I'd resign. I learned a brilliant way to deal with them. To boot these people off Yahoo for as long as I wanted, I'd try to log into their account.

When I used the wrong password 10 times, the account was locked for 24 hours. They couldn't log in again until I chose to allow it.


18. Forget Or Reset

My university requires that you change your password every few months or so. The new password can't be the one that you've used in the past. Naturally, this sucks because I have to remember yet another password. But, if you "forget" your password and reset it, it can be anything, and it counts towards changing your password. I've had the same password for my entire college career.


19. Free Sandwich Frenzy

I worked at a sandwich shop when I was a young lass. We were allowed one free sandwich for the entirety of our employment there. Being an endless pit of hunger that 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 have them never pick it up. I got free sandwiches every day. It was amazing. If I didn't eat it, I would bring it to school the next day and sell it.


20. Gumballs Or Movies

A Blockbuster near my house had a giant gumball machine near the cash counter that had special gumball-sized plastic orbs. Some of the orbs had a free movie/game rental voucher. So, for 25 cents, you had the chance to win a $4.99 rental. Well, this was around for my entire childhood. Until one day, it all changed. I walked past the machine and noticed it was almost empty.

It looked like the remaining ratio of gumballs to free-passes was probably three to one. See, when they first filled the machine years ago, apparently the employees just tossed all the passes on top and barely mixed it up. I came back with a stack of quarters and for $10, I got 17 free rentals and 23 gumballs. The rentals lasted a few months, the gumballs lasted a few days.


21. Three Out Of Four

I was in 10th grade when rubrics had recently been made mandatory for all school projects. The marks had to be bucketed into different mandatory categories, and teachers were still getting the hang of it all. Anyway, one day for science class, we had to construct a leaflet for the endangered animal we were assigned by the teacher.

I was assigned the leatherback sea turtle, which was quite a majestic soft-shelled turtle and the largest of all turtle kinds. The rubric handed out with the assignment bucketed the grade equally into four categories: overall appearance, the layout of leaflet, use of relevant images, and content. That's some nonsense, right? There were three categories dedicated to appearance, and only one category to content.

Naturally, I ended up handing in a piece of construction paper folded in thirds, covered in nothing but glitter, turtle silhouette cutouts, and about 15 fancy pictures of sea turtles. There wasn't a single word on that leaflet, barring the construction paper letter cutouts forming the words "LEATHERBACK SEA TURTLE" pasted in an arch shape at the top of the leaflet. I got a grade of 75/100.


22. Now You're Cooking With Gas

I'm not sure if they do this anymore, but many years ago, while I was an employee at HomeGoods, the store had this promotion where employees could get these scratch-off cards that reduced the cost of an item by one or five or 20 dollars each time they found a price sticker on the floor. Each card had three scratch-off areas, and the catch was that you could only scratch off one.

However, if you used a lamp, you could see which scratch-off area was the one or five or 20 dollars, meaning that you could very easily rack up a 20-dollar gift card for every sticker you found on the floor. The idea was that if employees collected these fallen stickers, nefarious shoppers couldn't stick them on something of far greater value and check out at that price.

There were no rules on how many of these employees could have or combine because most folks who worked at that store were middle-aged women who didn’t really care and most of the stuff HomeGoods sells is garbage. But then there was me. A starving, broke college kid who got paid horribly but who worked in the backroom unloading trucks, and who also was occasionally tasked with stocking shelves.

In short, I was the only person who seemed to care about this promotion. My bosses, who wanted to show their higher-ups that they were putting the corporate programs into effect, were happy to oblige each sticker I presented with a scratch-off ticket of my own. HomeGoods, while normally a purveyor of fine garbage, also occasionally has very nice, very high-end, housewares on the cheap.

These items, like cookware, linens, comforters, and more, are more often than not usually much more expensive than the rest of the store's stock, and take a while to sell. For me, the guy who unloaded the trucks, this meant that when I saw something absurdly nice, I could put it very high up into a loading bay and just let it sit for a while, because the senior citizens I worked with would never go up to get it.

At the end of a four-month summer, I'd amassed about $1,100 in these little gift cards. With them, I bought a full set of AllClad copper core cookware, a queen-size down comforter, duvet cover and sheets, pillows, nice flatware, plates, glasses, and a dozen useful kitchen tools. To this day, ten years later, I still have all the AllClad and some of the kitchen tools. It was all for free.


23. Best Vacation Ever

I spent five years on a US navy submarine. Every two years, we would do a six-month-long deployment called Westpac. On my second deployment, I got boondoggled with a few other dudes. Basically, the boat goes out for deployment without us and we get 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 then caught a flight to Pearl Harbor. We showed up with our orders to check-in, but there was some miscommunication. The office personnel really messed up. We find out we aren't enrolled in any of our classes. More than that, we don't have barracks, meal chits, or anything really set up. They had no idea we were coming.

They give us something called a "non-availability chit," which allows us to stay at any reasonably-priced hotel on the government's dime. Naturally, we found a palatial estate a block away from Waikiki. We showed 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 office guys got their work straight, they realized that our return plane tickets were already paid for and paper worked up. 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. I grew a beard, drank as often as possible, learned to scuba dive, did some surfing, went on dates with a bunch of international tourists, went on pub crawls every weekend, did some hiking, and did lots of snorkeling. I also woke up on the beach a few times with no recollection of how I got there. It was the best vacation ever. Thanks, Navy.


24. All For One Grand Prize

A long long time ago, Hostess chips, which were the major brand in Canada at the time, had a Mario Brothers promo. You got a "bingo" card in each bag of chips and every card was a winner. You had to scratch three of nine areas and if you matched the icons, you won. Then one of my friends figured out the key to the whole thing. 

He found out that if you used a tin can with a tiny hole punched in the bottom and then dropped down it onto a 100W light bulb, you could see through the card and find the winning spots to scratch.  This spread around town and a week later, there wasn't a single bag of chips to be found anywhere. They were sold out all over town.

We all had garbage bags of open chips around. I won one grand prize, which was a Super Mario Bros game.


25. Small But Mighty Haul

A couple of years ago at work, I was browsing Dick Smith's website and noticed they had a sale that reduced the price of all items below $50 by $10. I thought to myself, “Hmm…I wonder if I can try to purchase something for less than ten dollars and get it for free. Lo and behold, it works, so two co-workers and I ended up ordering about 15 miscellaneous items between us.

We got 3.5mm extension cables, phone chargers, and all things like that before the store seemingly cottoned on. It was a really interesting experience for us at the time, and we had a good chuckle to ourselves when a few days later there were 15 small, individual packages waiting for us at the reception area in our office.


26. A Physical Limit

My university was trying to encourage people to walk more, so if we downloaded a specific health tracker that's connected to our account, it would convert steps into points. The points would get you stuff like free coffee, mugs, discounts for stuff, and the most expensive prize: a university hoodie that cost about $30. Now, the health tracking app is pretty basic, and it won't let you log your steps manually.

However, it does let you connect with other health apps. So I found a health app that would let me add in the steps. I logged an equivalent of 30 miles (50km) a day. In a few days of logging manually, I would get myself a hoodie or two and I didn't get caught. I told my friend about it, and he really perfected the method of getting more steps a day, because apparently there was a hidden physical limit to how far a person can walk in a day.

But, he managed to trick it by setting his height to be one centimeter. The shorter you are, the more steps you need to take to cover the same distance. In the end, he claimed more than 10 hoodies and he would just get them for anyone who asked. The university found it suspicious, so he received an email telling him that the activity had to stop unless he could provide evidence that he walked that much.

Another friend had a different method. See, you get points just by being friends with them on the university health website. He also found that he could access a list of everyone who had an account on that website. So, he made a python script that would automatically send a request to everyone, earning him points without walking at all.


27. Reaching The Limit

They've closed it now, but a couple of years ago I discovered you could charge an American Express "Serve" card with a regular credit card by going to Walgreens. So, I have a credit card with 1.5% cashback. Every month, I put $10,000 on the "Serve" card, which was the limit, and then just paid my credit card bill with it. I cleared $150 per month for free.


28. Forgetful For Free

In college, I bought a pack of coupons for Hungry Howie's Pizza. It had three coupons for a free pizza with no other requirements. It was just a completely free pizza. So of course I had to go and take advantage. I would call and order my pizza, tell them that I had the coupon for a free pizza, and then show up and "forget" to give them the coupon every time.

I always had it on me as a backup, just in case they did ask for it. But, out of the three coupons, they only asked for it once. I kept using them for months, until the coupons expired, which I am sure they were looking forward to by that point. I ended up getting a few dozen free pizzas out of them, which was great for a college student.


29. The Jig Continues

There are these three Dunkin’ Donuts locations in my area that let you buy "Coffee Cards." Basically, you pay $200 for the card and can come through any part of the day, however much you want a day, and get any size coffee for a year. Well, my mom bought one last year and it had expired. She bought another one this year and it looks EXACTLY THE SAME as the old one.

They took no effort into changing the card at all, so my mom gave me her old one and I get free coffee whenever I want now. They're not scannable cards or gift cards. It's literally just a pink piece of paper in the shape of a card that has the Dunkin Donuts label on it and the locations where it's valid and a manager's signature.

It does have the date it "expires" on there, in really small print, but they have never once checked my card. They only ask me to "flash" it at them, so I guess the day they ask to inspect it the jig is up.


30. Gaming The System

There used to be an electronics store called Hastings where I grew up that sold both new and used electronics. They had a deal that if you traded in three used games of a common type, such as all PS2 games, you could get a brand new game for free, no strings attached. They were just free, as long as it was any game of that system.

So, I would go into the store to buy three incredibly cheap used games such as Bass Pro Hunting or whatever it was called for $5. They had dozens of them. Then, I’d just walk out, double back, and then trade those in for a $60 brand new game. I did this constantly for a few months while being harassed by the managers there until they stopped the promotion.


31. Life Was Never The Same Again

I wanted to get cheap coffee filters online as I knew I was going to need them for the foreseeable future and wanted to get a better price on them. So, I found a site that had them at half price, which came out to $1.95 for 100 filters, while they’re usually $3.99 at the store. When I went to check out, it asked me if I wanted to set up an automatic delivery to have them shipped every two weeks and they would reduce the price.

I thought, “Why not?” After all, they were the cheapest I had found, and getting them every week would mean I didn't have to keep ordering them. So, it brought the price down to about a dollar for 100 filters. I was thrilled. Then, it asked me if I wanted to join the Coffee Savers program for more discounts! Again, why wouldn’t I? But even I couldn't have predicted the next development.

After joining the savers program, it brought the price down to $0.00. I was stunned. I still had to add my credit card but I was never charged. So for two years, I got 100 filters delivered to my door for free. I never got charged even once. One day, though, I got a notice that said they were going out of business and my free filters would end.

I was sad. But, the stockpile I amassed lasted me for about two years. Recently, I had to buy new filters. Life will never be the same.


32. Cans For Candy

When my friends and I were in the sixth grade, we were always looking for a hustle. We would collect our parents' empty soda cans to return to the Safeway near us for a few bucks to buy candy. One day, they installed these big machines that automated the process, so the employees didn't have to manually count the cans.

You would put your can in the machine through a wide tube, it would roll the can around until it read the barcode, drop the can into a locked storage bin inside, and you would repeat this until all of your cans were tallied. It would then print a receipt that you would exchange for the cash amount of your cans at the register inside.

My friends and I tied a can to the end of a stick, got the machine to read the barcode, and then pulled the stick out before the mechanism would force our can-on-a-stick into its belly. We did this once a week and got about 20 bucks each time before we would get nervous and stop so we wouldn't get caught.


33. All Kinds Of KoolAid

The grocery store near where I lived had a fuel card you could sign up for. If you bought certain items, you would get $0.01 or $0.02 off per gallon, sometimes more depending on the item or week. One week, they ran a promotion that every one of their store generics would get $0.02 off per gallon, per item. I walk by the powdered KoolAid packets and notice they sell a generic version of that at a rate of 10 for a dollar.

I do the math. My vehicle has a 16.5 gallon tank, so I will need 157 packets of drink mix to get free gas. This will save me $36.11. I should do this. So, I count out 157 little individual packets of drink mix of all kinds of flavors, and go to the checkout. I tried to save the guy some time by telling him how many there are in each flavor, but the manager had walked by and stopped to see what was going on with the generic KoolAid.

So, the poor guy has to scan every single one. The manager makes an awkward joke about the amount of drink mix I'm buying, but when I pull out my fuel card, my ploy becomes clear. The cashier reads off my new fuel discount and I'm on my way to the gas station, where I proudly fuel up my vehicle. I still had to pay $0.16 since they wouldn't let me reduce the price all the way to zero. And then came the twist.

I took all the generic drink mix and donated it to the local food pantry, because I hate KoolAid.


34. Never Told A Soul

At a pool hall with my friends, I noticed a jukebox. This jukebox had tens of thousands of preloaded mp3s for people to take their pick. Late Saturday night was the pool tournament, and the place was packed. I realized you could download an app for your smartphone and sync up with the jukebox, pay with credit card and choose music on your phone.

In the app, I found that with every "new" account made, you would get a free song of your choice to play. I made several throwaway accounts and played "Spongebob's Campfire Song" and "Best Day Ever" on repeat. I almost forgot the grande finale, which was "Raining Blood" followed by "Through the Fire and the Flames." I never told a soul, until now.


35. Looks For Free

Years ago, when online poker was a thing in the US, there were sites that let you look at statistics on other players. They'd give you one free look, but I realized you could just manually change the player's name in the link and get unlimited free statistics from them. I used it a lot to see if someone was a good player or not before sitting down at tables with $20+ buy-ins.


36. Eight To Two

This is the story of how I passed math and graduated from college. So, my university was notoriously awful for its math program. They used MyMathLab and it was just generally horrible. I was terrible at math anyway. However, you had the option of testing out of classes. You would go to the testing center, pay five bucks and take a test. So this was my plan.

To get math credits, I'd go take the test, find out what I got stuck on, and then work on that type of problem until I understood how to do it. Then, I'd go back and take the test again. I probably took the test eight times in a semester. Finally, I passed the test and got my math credit out of the way. The next semester, a new rule was implemented that you could only try and test out of a class twice per semester.


37. Writing Around The Problem

This past semester, I needed to take a biology class with a lab to graduate. I was told that it was one of the easiest classes at my school to take. But, as a literature type, I didn't agree. It was so much information all at once, and I found it really boring, so I didn't do so well on the tests or assignments. I got Cs and Ds, even on the final that I stayed up all night to study for.

We also had a class blog. There were about 120 of us, and we each had to write three posts per semester on anything biology-related. I didn't do well in the lab section, either. I failed the multiple-choice test and the practical, and I assumed I was screwed. However, the professor said that if we made comments on our peers' blog posts, and turned in worksheets to show what edits we made, when, and on what topic, we could get five extra points per edit.

Most kids did two or three. I did 97. I ended up with an A for the semester.


38. But Not You!

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 5:30 PM 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.

So, they offered money/miles/flights as needed. Every Friday, I'd wait for them to make the first announcement. It would usually be a voucher, which I’d scoff at. Then, the second announcement, with probably a slightly larger voucher. I’d double the scoff. But, the third announcement…then came my time to shine. That's when they started offering the good stuff.

I'd take that one, which was 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! Then, they'd book me a guaranteed seat on the next flight, which was never overbooked anyway. And that's not even the best part.

The best part was that I got on the same connecting flight as I would have if I had been on the 5:30 PM flight out of Boston. I didn't do it that way to scam them. It was just the only connection available for either flight. I took that route 45 to 50 weeks a year for two whole years, and I lost count 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 “using 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. Actually, no, by taking advantage of them overbooking every time.

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. Then she followed it up with, "But not you, Mr. Tillerman." OUCH, lady.


39. Discovering A Loophole

A number of years ago, Discover (the credit card company) would run some extra high cashback promotions at certain retailers. One of them was Barnes & Noble, and they'd go as high as 10% cashback. At the same time, Discover would allow you to buy gift cards at a discount using your cashback balance, and they sold Barnes & Noble gift cards at 10% off.

The loophole was that Discover would credit you cashback on a purchase if you had your Discover card as your primary payment instrument on your Barnes & Noble account, even if you didn't actually use it to make the purchase. Starting with cashback I had already earned from other purchases, I bought gift cards, went to Barnes & Noble online, bought Nook ebooks with the gift cards, and got cashback as if I had used my credit card.

Every month for a couple of years, Barnes & Noble and Discover were basically paying me to buy ebooks. They stopped those promotions, so now I just use my cashback to buy stuff at Amazon. I did have a Nook Simple Touch at the time, but even if I didn't it was still worth it because Nook books are epubs, and they have trivial DRM that is easily cracked.

Thus, even if I were a Kindle or Kobo or other user, I could still buy those Nook books, crack them, convert them as needed, and read on my chosen device.


40. Running Through School

Washington state high schools have a program called Running Start. It allows juniors and seniors to attend community college classes for both high school and college credit. I was not enjoying my high school experience. I already knew the material as the Colorado schools I came from were ahead of the Washington state curriculum, and there were a lot of disruptive students that led to half of the teacher's time being dedicated to discipline.

I was rapidly losing interest, and my grades started to show it. One day, I was called into the guidance office and offered a summer job as a tutor for my peers. I told him how much I hated the classroom environment, and he dusted off a few books and I started the Running Start program. The only class I attended at high school was a homeroom, then I'd walk to the bus, grab a coffee, and spend the rest of my day at a community college that was right next to my house.

Some classes had only a semi-final and final, so I could freely skip them and sleep or play video games at home. In another class, the teacher had quit and it became an online course. It paid off for me, big time. I did very well, and by the next year, I didn't even have to show up to high school. By the time I graduated, I got an associate's degree as well.

The loophole aspect is that the school hadn't used the program in many years, and the guidance counselor had no idea what he was doing, as I was supposed to be limited on the number of classes I could take in substitution for high school classes. I got away with a logic course being counted as statistics, a forensic anthropology class as lab science, and took a full college load when I should have only been allowed two classes. Also, my day should have started and ended at the high school.


41. Along For The Ride

When I was in grad school, I moved into an apartment complex that had promised me free shuttle rides to the nearby train station. It was a big factor in deciding whether to move there because I didn't own a car. Well, a couple of months after I moved in, they started charging for the bus rides. They had these punch cards, which were $10 for 10 punches.

The problem was that these punch cards had no security features in them. They were just cards made out of colored cardstock. So, I used Photoshop to mimic the cards as best as I could and had several sheets printed at a local print shop. I carefully cut them out and started using them. I had to be careful that I didn't let the bus driver punch the 10th slot, though, because then he would take the used-up card.

I didn't want those cards to be returned to the office and have them notice a discrepancy that the driver wouldn't. I did this for about a year before I moved out.


42. All For The Show

There's an app called Viggle where you can earn gift cards for watching TV and answering questions. I started using it very early when there were still some bugs. I exploited the heck out of these loopholes. At my height, I had 10 accounts running at once and made about $250 per day just from four to five hours in the evenings.

All told, I made about $20K from that app. The best part was the questions, but they eventually ran out and you needed to wait one or two hours until you could answer them again. Well, if you logged out and logged back in, you could answer them again immediately. Also, the app listened to the audio and detected what show you were watching.

C-Span, the tennis channel, and HLM would often have 10- to 12-hour shows. If you checked in once, you were good all day.


43. Missed The Memo

A few years back, when Activision decided to pull the plug on Guitar Hero, Toys R Us decided to sell all their copies of the game for $10. The guitar/drum set was going for $30. I saw the article online and hit up every single store in my area. They were sold out that afternoon. I sat there, defeated. I had always wanted the entire set, and I had owned previous copies, but I never wanted to dish out the cash for the entire kit. Then it dawned on me.

It was an idea so far-fetched, it could only be genius. I decided to go for a Hail Mary. So, Best Buy has a price-matching policy. I didn't even think about it. I shot out towards the nearest store. I walked in and saw all the games and kits were still full price. Come on, it's Best Buy, there’s no way they were gonna lose out on that profit.

I walked into the game section and asked one of the representatives about the price matching guarantee. The guy looked at me like I was bonkers. I had printed an ad for the sale. I took all the games and a full band kit to the register and asked to see the manager. This tall douchey-looking white guy came up to me with a grin.

He told me that the ad was probably fake, and that he was not going to honor their policy. I didn't even think about it. I just said, “Okay, call them." He picked up the phone with a suspicious look, and he got in touch with a local store. He asked about the promotion. He went pale when he heard the voice. Immediately, there was a look of fury in his gaze.

The manager then turned around and could barely mutter the words to the cashier, "Honor the discount." She just stood there, thinking he was joking. The manager said, "Do it," and just proceeded to walk away. Even his stride told a story of his anger. The cashier gave me the discount, and in a cocky tone told me it was still going to be around $50.

I then smiled and took out a rewards coupon for $50. They still have to give the items a price, so I could use the coupon. I paid cents for everything and I went home a proud man. I beat the system. A few days later, I met a guy that worked at one of the Best Buy stores. I told him my story. He started to laugh. It turns out Best Buy sent out a memo to NOT honor the price-matching guarantee unless the competitor had the items in stock. The idiot manager didn't bother to ask that simple question.


44. The Final Wager

In geography class for fourth grade, our class was split into groups of four and given a book full of sheets of questions. Some examples of questions would be "What is the largest mountain chain in South America?" or "How many continents border the Mediterranean Sea?" Each sheet was supposed to be done at home individually and then on Friday you were supposed to go meet with your group and share the answers.

Then, the teacher would go over the answers and keep score for all of the teams. There were eight to 10 questions per sheet with 10 points per correct answer. Every six weeks, we would do a competition to earn more points. It was Jeopardy-style where the teacher would read a question and you had to press a button first to be able to answer.

At the end of the competition, you could wager the points as you do in Final Jeopardy. The teacher seemed to try to divide the class into fair groups. Each group had equally smart kids and not-so-bright kids. However, I felt like my team was definitely the rejected team. I had one girl who always brought in completely wrong answers on her sheets.

One kid wouldn't even do his sheets, and the last girl tried her best but wasn't quite up to par. One team, however, had two students that were very bright. They were honor students all the way through high school. So, after the third six-week Jeopardy competition, we were in last place by a fairly substantial margin. The dream team was first, of course.

However, I was the last one on my team chosen to do the six-week Jeopardy competition. That was what allowed me to find the loophole in the competition. The questions that the teacher would use for the Jeopardy competition were from the questions in the previous six weeks, but the Final Jeopardy question was always one random question from the sheet exactly four weeks ahead of the sheets we used.

So, the first Jeopardy competition questions were from weeks one to six, but the final question where you can wager all of your points was one question from week 10. So, all year long, I have to answer all the questions on our sheets since none of my teammates were capable. I had to sit there and watch my teammates go into the Jeopardy competition and come out in last place.

To top it off, the teacher kept this huge shiny scoreboard created with colored construction paper updated each week. It was hung by the front door of the classroom so you could see it on the way out. So, going into the final Jeopardy competition, I went ahead in the sheets and studied all of the questions on the sheet four weeks ahead of the current week.

By the time we got to the final wager, I had built up a decent sum of points to wager. To add to that, the teacher let us wager all of the points we had accumulated the entire year on the final question of the Final Jeopardy. I remember the entire class being shocked because this was a brand new rule she threw in at the last second.

So of course, I wagered all of my team's points from the entire year to try and double up. I remember we had something like 1,700 points, whereas the top team was like 4,000 to 5,000 points. The teacher reads the Final Jeopardy question. When I heard what she said, my eyes lit up. I knew the answer. I had figured out the loophole and was about to cash in big time.

I was the only team representative to answer the question right. However, it was only enough to propel us into second place because the top team did not wager many points or they were so far ahead that it simply didn’t matter. I'll still never forget the smile on my teacher's face when she saw my answer to the final wager with all my team's points on the line.


45. Rinse And Repeat

My brother got free parking for pretty much his entire time at university. It was that golden period when the pay parking kiosks were able to accept credit cards, but before they were actually connected. They'd read a card and check it against a locally stored list of banned numbers. Once a month, the meter maid would download the transactions, process them, and update the blacklist.

My brother found that they'd accept those prepaid gift cards if they were backed by Visa or MasterCard, but they couldn't check the available balance. So, he'd buy one, use the balance up on whatever, then use the card for parking until the end of the month when it'd get processed, found to not have funds, and banned. He’d rinse and repeat. The guy saved probably $2,500 over his degree.


46. Beats Traditional Work

My roommate at the time bought a car with his Best Buy bucks. How he did it was amazing. He sent in a ton of self-addressed stamped envelopes to get game pieces. Each game piece had at least $1 of Best Buy money, but some had $3. There's a law in Vermont that doesn't require the sender to provide postage for the return envelope on a SASE.

So, he had all his game pieces mailed to a PO box in Vermont, thus saving $0.37 per entry. Then, he had all the game pieces bulk shipped to his home. It was much cheaper than spending $0.37 per entry. Once he got his game pieces, he peeled all of them, collected his Best Buy bucks, and went around buying MP3 players from stores.

Best Buy got wise to this pretty quickly and had a $200 spending limit per day, so he'd travel around the entire metro area, hitting every single Best Buy and spending $200 at each one. Then, he sold them on eBay as new in-box for maybe $10 to $20 off the retail price. I think he made around $10,000. It was a lot of work, but it beats working I guess.


47. A Pretty Smart Cheater

When I was in high school, I applied for a summer job with the county. As part of the "unbiased" application process, each applicant was asked to take an intelligence test. The test consisted of about 80 questions. Each question was four or five line drawings, and you had to put an X in the box next to the one that didn't belong. It was pretty easy.

I happened to notice, though, that the test paper was two-part, which is two sheets of paper that are attached together back-to-back with a sheet of carbon paper in between. So I could peel the sheets apart and look inside. The second sheet just had a bunch of boxes printed on it, and I could see from the first few questions that I'd answered that the Xs I'd marked ended up in the printed boxes on the second sheet thanks to the carbon paper.

So, I did all of the questions with obvious answers, and if I was unsure, I just peeled the paper apart, noted where the box was printed on the second sheet and made sure I got it right. Of course, I got 100%. I figure that if you can cheat on an intelligence test, you're pretty smart.


48. Nonsense To New Names

I coach a high school team. We recently bought airfare with Spirit Airlines to take nine students to a competition. Two of the students canceled about a month out from the trip, and we had to replace them with two different students. Spirit Airlines had a stupid policy: no name changes. You can't even pay a fee to change the name.

The tickets were basically lost, so I have to buy new tickets. This is where it turned into a nightmare. Spirit's customer service is overseas, and they plainly don't care at all about customer service because they don't actually work for Spirit, but just work in a general call center. However, I found out that Spirit Airlines DOES allow passengers to correct misspellings.

And, these folks don't really recognize nonsense names. So over four calls, I change the names of the canceled students to the names of the new students, two letters at a time. No one at Spirit customer service made a note because they really didn’t care, and no one ever noticed that the "correct" names during the intermediate steps were nonsense.


49. All Well Worth It

My buddy and I were playing one of those "ball dropping" machines, quite similar to Japanese pachinko games, in a theme park that gave out tickets that were redeemable for prizes like huge teddy bears, stationery, souvenirs, cheap gadgets, and stuff like that. After about five minutes of playing, we hit the "jackpot bonus."

The machine started going crazy and spat out tickets as if it were having some sort of ticket diarrhea. We tried collecting as much as we could and it just kept giving out tickets. So we started giving them away to kids who were nearby. This went on for close to an hour and we were like Santa Clauses, making it rain tickets on many very happy children, parents, and even a few young couples who wanted those big teddy bears.

By the time the machine ran out of tickets, we had almost emptied out the prize booth and the park attendants didn't seem to mind at all, seeing how happy all those kids were. It was a really awesome day and some of the parents came to thank us for making their kids happy, all misty-eyed. At the end, we didn't even get to claim a single prize for ourselves that day.

It was worth it seeing all those smiles and laughs. The best part was that the park crew seemed like they knew what was going on but they didn't care enough to stop it, even though we saw them getting chewed out by their manager for not stopping the machine earlier. We had a chat with one of them later that day and she said she knew the machine was broken, and it shouldn't have been operating, but they hate that the management tweaks the machines to make winning really hard and this was the park crew's way of getting back at them.

So, every so often, they would stuff that machine full of tickets and just let it run.


50. Supply And Demand

The online community that played Diablo 2 created its own form of currency by trading valuable in-game items for rare rings called SOJs, or Stones of Jordan. For instance, if you wanted that rare +attack power armor, you would buy it for 12 SOJs. Anyway, I figured out that there was a discrepancy between the worth of an SOJ in-game and its actual monetary worth on eBay.

This was the same with magic items, but in reverse. I would buy SOJs on eBay for cheap, go in-game, and trade them for rare magic items. Then, I would sell those magic items on eBay for way more than I paid. The results shocked even me. I made enough money to pay for college, and other living expenses. Honestly, incredible.


Sources: Reddit,


The Yawn-Inducing Hall of Fame: Top 15 Most Boring Jobs

Take a humorous dive into the top 15 most boring jobs in the world. From watching paint dry to counting cars, discover the less-than-thrilling day-to-day of these necessary, yet yawn-inducing roles, along with what they entail and what they pay.
November 14, 2023 Allison Robertson
worst employees

The Worst Types Of Employees In The Workplace

Navigate the minefield of workplace dynamics with our guide to the worst types of employees. From procrastinators to gossip mongers, discover why these characters can disrupt the harmony of any workplace and how to handle them effectively.
November 27, 2023 Sammy Tran
Gerald Ratner Editorial

Doing A Ratner: Honesty In Business And The £500 Million Gaffe

Gerald Ratner built a massive jewelry empire from the ground up by himself—then, in just a matter of minutes, he destroyed it all.
January 19, 2024 Samantha Henman

These People Shared The Worst Moments Of Their Lives…And They’re Utterly Brutal

From cheating spouses to catastrophic accidents, there are times when life throws brutal punches...and these people have firsthand experience.
March 1, 2021 Eul Basa

World Travelers Share Their Best Travel Tips and Tricks

Being a savvy traveler is something that only comes with experience. These frequent flyers share their best tips and tricks to help you travel seamlessly. 
November 15, 2019 Eul Basa

Dear reader,

It’s true what they say: money makes the world go round. In order to succeed in this life, you need to have a good grasp of key financial concepts. That’s where Moneymade comes in. Our mission is to provide you with the best financial advice and information to help you navigate this ever-changing world. Sometimes, generating wealth just requires common sense. Don’t max out your credit card if you can’t afford the interest payments. Don’t overspend on Christmas shopping. When ordering gifts on Amazon, make sure you factor in taxes and shipping costs. If you need a new car, consider a model that’s easy to repair instead of an expensive BMW or Mercedes. Sometimes you dream vacation to Hawaii or the Bahamas just isn’t in the budget, but there may be more affordable all-inclusive hotels if you know where to look.

Looking for a new home? Make sure you get a mortgage rate that works for you. That means understanding the difference between fixed and variable interest rates. Whether you’re looking to learn how to make money, save money, or invest your money, our well-researched and insightful content will set you on the path to financial success. Passionate about mortgage rates, real estate, investing, saving, or anything money-related? Looking to learn how to generate wealth? Improve your life today with Moneymade. If you have any feedback for the MoneyMade team, please reach out to [email protected]. Thanks for your help!

Warmest regards,

The Moneymade team