Only a tiny fraction of society are born with a hustler gene. Not only do these people find ways to bypass the rules, they seem to rewrite them altogether. And what for? If not for the thrill, then for getting what they want.
Call it a selfish code in their DNA or a Wolf of Wall Street phenomenon, you can’t help but wonder how it’d be different if we too could learn a little bit from them. Turns out, it all starts with spotting the loopholes, big and small, and learning to use them to your advantage.
“What is a loophole that you found and exploited the hell out of?” someone asked on Ask Reddit, and the thread got people sharing how they managed to milk the system, to get away with things, to attain something that wasn’t theirs and so on and so forth. Read below for the most interesting stories!
#41
This pizza place local to us had a glitch in their online ordering service for a while. You could technically combine 2 deals of 50% off. One was 50% off for any XL pizza of an order that was normally $30 or more, and the other was 50% off on a XL Pizza, with two 2-liter drinks, wings, and cheese fries at regular price.
If you put both of these coupons in, you only paid for the wings, cheese fries and pop which would be about $18. With delivery charge + tax it would be about $25. Plus 2 Extra Large Pizzas for literally free.
Normally this would be $70+. Any other coupon you could not combine, but this one worked together for some reason. For some other reason it would mark 50% off 2x on each pizza. We discovered this when we were ordering food the day we moved in. Feeding our friends that helped us move in. We thought it was a 1-time thing. Tried it a few weeks later and it worked. We did this at least once a month for the year or so we lived there.
We always gave the driver a $10-$20 tip and he knew what we were up to. The place never said anything about it for years. Eventually they updated their site a couple years ago, and we had moved out by then.
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56points
#42
The Starbucks subsidiary Teavana (now out of business) would let you use your Starbucks rewards ("stars" or whatever they're called) to get loose tea by the ounce. However, there was an error in their point-of-sale system that only deducted 1 reward point, no matter how many you spent in a given transaction.
My wife and I spent 32 rewards on a couple pounds of the most expensive loose tea they had. She checked her rewards balance the next day, and holy s**t, she still had 31 reward points left.
So we drove to a different Teavana and got a bunch of loose tea from them, and then another, and then another. We were in Los Angeles, so there were a lot of Teavanas within driving distance.
At retail price, we took a thousand bucks or so of free tea off their hands before the loophole was closed.
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54points
#43
There’s software that generates credit card numbers. Now you can’t actually buy anything with these numbers, because when the system tries to charge them, it gets rejected.
However, there was a website (like many others) that would give free amazon gift cards (via email) for trying out partnered subscription services that offered free trials.
You’d click the offer link, get redirected to the partner site, fill out all the information and use the fake number, and it would confirm on the offer site before getting rejected by the partner site. About a week later, you’d get a digital amazon giftcard in your inbox.
Got enough to buy a PS2. Long time ago, haha.
However, there was a website (like many others) that would give free amazon gift cards (via email) for trying out partnered subscription services that offered free trials.
You’d click the offer link, get redirected to the partner site, fill out all the information and use the fake number, and it would confirm on the offer site before getting rejected by the partner site. About a week later, you’d get a digital amazon giftcard in your inbox.
Got enough to buy a PS2. Long time ago, haha.
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53points
#44
Sears has a program called Shop Your Way Rewards. They had some electronics items back in the day that would give you roughly the same amount of points back that the item cost. So a $40 pair of headphones would come with $30-$40 worth of the SYWR points. Well a group of enterprising folks found out how to generate as many coupons as we wanted and that $40 item became $25-$30 and the $30 in points became $40 by using coupons. You could also use points to pay for the item in question as long as you spent $0.01 in cash. So I was getting +$9.99 for every order placed. Sometimes it was order 5 of these things for $200, use 2 awesome coupons and you’d get back $250 for $160 in points spent on the items. I bought so much stuff from Sears over the course of 2 years. Made roughly $50,000 selling the junk electronics on amazon/eBay. And was able to stock up on craftsman tools, clothes, new appliances, and a couple of recliners using the points I acquired. I ended up on a first name basis with Shelley (or Sheila maybe?) the SYWR rep that ended up banning all of my accounts lol.
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46points
#45
I used to have a Suntrust debit card that offered Delta Skymiles rewards with every purchase ($1 purchase = 1 Sky Mile). Walmart would let you buy a $1500 money order for 70 cents. I would drive around, buy $10000 worth of money orders, fill them out, deposit it into my bank account, and then buy more money orders. I would often have to call Walmart managers and ask them to refill the ATM machine with money orders.
I bought a few million dollars worth of money orders and got a few million Delta Skymiles that I've used to travel across the world that cost me almost nothing (time + gas + $0.70 money order fee). One day I got a random call from my bank asking "what's going on with all these transactions?". I didn't have a good answer and they presumably thought I was a drug dealer or money launderer and canceled my account.
The Skymiles are probably worth a few hundred thousand dollars. A few years later I applied for a credit card from Suntrust and I was rejected due to "previously unfavorable business relationship". I took that to mean they finally figured out what had happened.
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46points
#46
The first three SimCity games:
* Build a modest-sized town
* Set tax rates to something high, but not high enough that it reduced the population
* Turn off disasters
* Set speed to super-fast
* Go to sleep
* Wake up a zillionaire
* Set tax rates to something high, but not high enough that it reduced the population
* Turn off disasters
* Set speed to super-fast
* Go to sleep
* Wake up a zillionaire
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44points
#47
In college I worked at a dining hall with a parking deck right next to it. Parking pass would have been several hundred dollars a year, and to park in the deck without a pass would have been $10/day for the hours I would be at work and in class.
But it wasn’t automated, and the booth workers went home at 11pm, so after that they had to leave the gates open for residents to get in and out. Being a college kid, staying on campus until 11 was easily doable, so I parked for free for two years.
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43points
#48
At my work, if you want to purchase more holidays they calculate the cost via what they pay you per day and then spread the total cost over a 12 month period to make the purchase easier for you. So if you buy 1 extra day and your rate is £50 a day, you only pay £4.16 a month for example.
If your pay increases the cost scales with it which gave me an idea.
I knew i was in for a pretty big payrise so I bought 10 holidays just before it happened and asked if I could pay for them upfront, they agreed but thought I was mad.
I got the payrise but all the holidays were paid for upfront on my old salary and they didn’t clock on so I saved about £400.
Noice.
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42points
#49

When searching for sources on essays teachers warned not to use Wikipedia.
On the other hand,he said noting about Wikipedia's own sources.The final product is so different that not even an software can make find similarities.
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38points
#50

Dating myself here, but in the late 80s, soda machines had just begun accepting dollar bills. You could take a bill and apply a piece of clear packing tape to it. Once the machine took the dollar, you could pull it back out using the tape. Free coke, but the best part was that you got change back! Paying you to drink a coke.
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31points


