The Most Incredible Ways People Outsmarted the System

35. Conned the Con Men

One day when I was in college I was walking through one of the on-campus parking lots back to my dorm when I saw these two guys trying to sell “high quality” surround sound systems out of their car. I recognized one of them from my high school, he was a grade older than me and a general putz. Out of curiosity, I listened to their spiel, it was some obviously bogus pitch about how they were installing them in the Whittemore Center but they ordered too many by accident and blah blah blah. Just looking at the boxes you could tell they were cheap Chinese knockoffs and worth probably nothing. I could clearly tell they were excited they had “hooked” me so I told them I just had to run over to the ATM to get the $300 they wanted. After a few minutes, I went back and told them I only had $301 dollars in my checking account and I needed $3 to deposit first so I could withdraw the $300 and not get hit with an overdraft fee because of the different bank ATM charge. So foaming at the mouth they give me $3 and I wander back over to the ATM. I ducked around the back and across campus to my dorm, $3 richer but mostly just entertained that I conned the con men.

36. Rich families

Private schools are notorious for accepting cash from parents paying for their kid’s tuition. And I’m not talking about monthly. I’m talking about dropping a year’s tuition in cash. Wealthy families will do this because the cash is undeclared and would be taxed otherwise.

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37. Don’t Judge

About four or five years ago I had a friend that worked at a grocery store. Whenever we would go grocery shopping he would act like he was scanning everything but only scan the cheap items. We would get like $70 worth of food for $15-$20. We never asked him to do this, he took it upon himself to. I never argued because I’m poor. Don’t you judge me!

38. Respect Him

Back in the day in high school, we had our “huge” junior term paper to do. Our teacher absolutely required that we have some ridiculous amount of like 100 note cards all with individual quotes on them, and citations from the numerous sources we were supposed to have collected and read for this research paper. Most of us in the class hated this teacher and she hated most of us, I think.

None of us was actually making the 100-note card citations and keeping them in little boxes and then organizing them. It was ridiculous. So when the note card deadline came up in like February or whatever, almost no one had all the note cards. I got busted in class for not having them and she called my parents and told them to talk with me because she thought I was a druggie burnout who didn’t do anything. Actually, I had done like 50 legit cards.

But one kid in class had made zero note cards. The night before he just made up a sh*t-ton of quotes and fake names and put them on cards and put them in his box.

The teacher thinks he’s a goody-two-shoes, so pulls out his box from the pile in front of the whole class, flips to a random card, and reads the quote, which is 100% made up the night before. It was something like: “We are the Molemen, we must make it over that hill. We are the greatest warriors to ever live.” – General Mole (1942). We were all like, ‘Oh, he is f*cked.’

Teacher raises an eyebrow, ‘General Mole,’ Jonathan? And I kid you not, without skipping a beat kid replies: “Yeah! Do you mean to tell me you don’t know who General Mole is? One of the greatest French generals in World War 2?” And she’s like ‘Oh,’ puts the card back in the box, and moves on to the next person to bust.

We all hated him for that cause he didn’t do any of the work we were supposed to. But I still respect him for pulling the wool over that lady’s eyes so easily. Wish I could b*llsh*t like that…

39. Gets an A

My friend is a college student and is pretty much the laziest person I know. He purchased dragon, that one program where you speak and the computer writes down the words automatically. He installed a microphone-type thing and hid it underneath the professor’s podium. All the notes he needs are transferred to his laptop, and he doesn’t do sh*t in class. Then he just reviews his “notes” and gets an A. I hate him for it, but I am a little impressed with his simple cheating.

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40. Friendly Assistance

41. Not Once

FREE FIRST CLASS. Every. Single Time.

Wait to be the very last person to get on board a flight. If there is an open seat in first class, just sit down. I used to fly to and from Denver and ATL all the time and not once did I even get questioned. They don’t have a first-class manifesto (or don’t check it). Worked maybe 15-20 times.

“Yeah, I’ll take a Jack and Coke, please.”

42. Hot Tub

When I quit a job over a decade ago, my boss forgot to submit my termination form. I kept getting paid for over 3 months. And I was a manager, making pretty good coin.

I knew they’d eventually catch it, and I thought they’d ask for the money back, so I banked every check and didn’t spend a cent.

So the paychecks eventually stopped after 3+ months, and I waited for the call or letter asking for the money. It never came.

Two years later I used the money to buy my hot tub. Now my *ss gets massaged by bubbling water thanks to my incompetent ex-boss.

43. Without Any Payment

I get a large cup of iced coffee from Starbucks every day for free.

Starbucks has this policy where you can get refills at $.55, or free if you have a Starbucks card. Now – normally they’ll ask you for your cup and your receipt, and then mark your cup when you receive a refill so that you can only get one refill per purchase.

Here’s the catch: every drive-thru Starbucks location I have been to never even bothers to ask for your cup, and will rarely ask for your receipt, so I’ve been asking for large ‘refills’ every day for the past three months without any issue at all and without paying a dime.

Enjoy your newfound source of free coffee (and not that sh*tty office breakroom kind).

44. A Few Weeks Later

Had a guitar broken at the neck (and briefly lost, but that’s beside the point) on an Air Canada flight back in 2008. Got a quote from a local music store for how much it would be to replace it. Called Air Canada and told them that not only could it not be repaired, but that I needed it for school (not a lie – I was getting my BMus in jazz guitar at the time) and expected them to reimburse me. Took the guitar back home, and got it fixed for about $90 (still plays and sounds great almost 4 years later). A few weeks later, I get a check in the mail from AC for about $1100 and promptly use said check to buy two new guitars.

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45. Present Every Day

When I was still in high school I was dumped by my first love; fell into depression and started skipping school to lay in bed. I know, lame, whatever I don’t do that anymore. Anywho, I skipped about half of my junior year of school. I achieved this by erasing the answering machine when messages were left and throwing out the letters that were sent home to my father about my attendance; he worked swing shift so most of the time he was at work when I was supposed to be getting myself up for school and then when he came home from work I would already be at my job in Burger King. So, after skipping about 50 days or so I decided it was time to get my sh*t together and go back to school. I get to school and my first-period teacher asks me what I was doing there and then says that I should probably head down to the principal’s office. Once there I was informed that I was expelled for missing school, but could sign up for summer school if I would like. So I went home and enjoyed the rest of my junior year off. I told my father that I was going to summer school in order to take some extra classes that seemed interesting and to “get ahead.” Once summer school started I found out that the only requirement to pass the summer was to get 100 percent on every test on every makeup chapter for every class. The make-up classes were super easy substitutions, though; for example, Earth Science was used for me to make up my Chemistry classes credit, while Algebra was used to make up my Trigonometry credit and so on. I had the most make-up work out of any student in there, but I was the only one that figured out that instead of reading the chapters and then taking the test over them, one could just take the tests over and over again until one received a 100 percent. This was made possible by the fact that they were all multiple choice answers and once you failed the tests you were told which answers were wrong. By process of elimination and common sense, I passed many, many tests over the course of an 8-hour day of summer school. It took me two weeks to make up my year’s worth of work. I had 7 classes to makeup, I finished them before any other student, most of which had only 1 or 2 courses to make up for. Now, when I was done I was informed that I was supposed to be stuck in school the entire summer because I was attendance based, however, there was no work for me to do. So the teacher in charge told me that “if anyone asks, you were here every day for the summer, but you don’t have to return.” She marked me as being present every day for the summer. I started my senior year of classes as if nothing ever happened and graduated school on time. Wouldn’t have been possible if the teachers hadn’t liked me so much, but hey it all worked out in the end.