1. Denis Rubin

A long time ago, when I lived in New York (Manhattan), my car was towed for a parking violation. When I went to retrieve it, I realized that the storage fees at the impound lot were lower than those charged by the private parking garages. Due to work, I wasn’t going to need the car for the next two months, so I left it safely in police custody at considerable savings.

2. Casandra Clements

I was waiting to board a Southwest Airlines flight with my husband and two young children in the family boarding line. For those that have never flown Southwest (do those people exist?), boarding is done in the order in which you checked in to the flight. There are no assigned seats. Families with young children are exempt from this boarding procedure and are allowed to board before the general boarding in order to allow them to get seats together. In front of us in the family boarding line was a dad with his young son. An attractive younger woman with lots of carry on luggage walks up to me and starts chit chatting about Phoenix (the flight destination) and other small talk.

As family boarding begins, she strikes up a conversation with the guy in front of us which continues as they move forward in line and into the jetway. I caught a glimpse of the C49 boarding pass in her hand (late boarding position) and laughed to myself about her clever use of looks and conversation to weasel her way into early boarding disguised as that kids “mom”. I don’t think the dad even realized what had happened as he was too distracted by the beautiful and friendly young woman he was chatting with.


3. Nitin Dubey

I didn’t witness it, but this made the news some time back.

James McElvar, singer for a Scottish boy band called Rewind, was told at an airport that he was carrying excess baggage. It would cost him a £45 fee.

His two options were:

  1. Pay the fee, or
  2. Throw the extra weight away before checking in.

He chose option 3: he wore all the clothes he was carrying. That’s six t-shirts, four jumpers, three pairs of jeans, two pairs of jogging bottoms, a pair of jackets and two hats.

What is The Most Brilliant Example of Taking Advantage of a Loophole You Have Ever Witnessed?

It was like the Friends epiosde where Joey puts on all of Chandler’s clothes.

It was a legal circumvention of a loophole. His luggage had to be within the prescribed weight limits but as long as he fit in the aircraft seat, they could not place restrictions on how heavy he was.

He was allowed to board without having to pay the $45 and still had all his clothes on him. Literally.

The story didn’t end well. McElvar collapsed from heat exhaustion halfway through the flight. He was attended to by an off-duty paramedic on the flight and later recovered in a hospital in Glasgow.

Idea: Brilliant.

Execution: Ermm, not so much.


4. Colin Petersen

In October 2015 I turned over more than a million dollars on my credit card to earn airmiles/rewards points. This loophole has since been closed, I believe at least in part due to my use of it.

In 2015 every bank in Australia treated depositing money into an online betting site from your credit card as a cash advance rather than a purchase, except one.

Also at that time, every Australian online betting site I knew of required you to bet money deposited at least once before you were allowed to withdraw it, except one.

That combination of features allowed money to be moved in a circle from credit card to betting site to bank account and back to credit card at zero cost but earning rewards points.

What is The Most Brilliant Example of Taking Advantage of a Loophole You Have Ever Witnessed? 1

In the morning I would max out my credit card depositing money to the betting site. At lunch I would log in to my betting account and withdraw the money.
At night it would be back in my bank account ready to use the next day.
Rinse and repeat 5 days a week.

Phase2 involved ramping up. Having become comfortable that none of my bank, my credit card issuer, or my betting site seemed to be alert to the issue I added money from my savings to my credit card to give it a positive balance so that I could move larger amounts. I went as high as $50k/day, on ANZ’s rewards program the points from that were worth $400/day if redeemed for cash.

Eventually the betting site changed their rules to require deposits to be turned over before being withdrawn and ANZ changed their T&Cs to reclassify deposits to betting sites as cash advances so the loophole was well and truly closed; all good things must come to an end.

Some of the money I saved, but a large chunk I used on an indulgent wine trip. Return airfares for 2, luxury car hire, accommodation, and many many wine purchases were all paid for by this loophole. Above my desk I keep the credit card statement to remind me of this scheme, and a photo taken enjoying a drink overlooking some of the beautiful vineyards of Margaret River.

Be alert to opportunity. Act with conviction. Enjoy memorably.


5. Elizabeth Muller

My parents came to visit me in Paris, and wanted to visit Notre Dame.

There was a very long line of people waiting to go inside. I asked them if they wanted to visit Notre Dame the American way, or the Parisian way. They said, of course, the Parisian way. So I took them straight to the front of the line and we walked inside.


6. Ben Faubion

It’s not really abuse, but if you are self-employed there is a world of discounts awaiting you. The trick is, your personal life and spending habbits need to be tightly aligned with your profession. For example, I am a designer and artist.. you wouldn’t believe all the legitimate write-offs someone like me can get. For example – movie tickets, travel, books, electronics, heck..even office furniture. If you tally it all up from your business debit card purchases at the end of the year, your tax savings might just be fantastic. The trick is to purchase with a separate debit card so you can easily track the write-offs, and don’t overspend.

My taxes have been lower than employed people for years.. the humble “sole proprietor” status saves you so much in taxes, and it’s all legal. People think self-employment taxes suck.. I was shocked how much tax an employer was paying to the government on top of my other taxes. Self-employment taxes don’t suck at all, when you know how to make it work for you.


7. Snehdeep Bahadure

This was during year 2003. I had recently shifted from pre to post paid connection on my cell phone connection.

While the GPRS was newly introduced it was super costly. But it was like once you get hooked with using internet on the go you are ready to pay the cost.

So internet was default activated on my cell. But one day casually while checking the data cost incurred, it went beyond the whole pocket money and so had to deactivate before bill cycle ends.

Now when the bill was received i found that data wasn’t charged even a single paisa. I enjoyed it and tried to experiment it again.

So then I tried it again in next month by activating internet on second day of bill cycle and deactivating a day earlier to bill cycle end. Again no charges. Experimented again and got same result.

Unfortunate for me that the service provider found this loophole somewhere in 2011. And yes till then I literally EXPLOITED this. Sorry and thanks dear service provider. Do remember ‘An !dea Can Change Your Life.’


8. Teresa D

It’s not too crazy, but it’s def a loophole…

Right now in my area there seems to be an explosion of those mail delivery meal kits companies. Basically they ship food ingredients to make meals to your house along with recipes. For example, blue apron, hello fresh etc. Since there seems to be so much competition and new ones in the market, they have crazy good promotions, like $60 worth of food for the price of $20, or sometimes just for the cost of shipping.

A friend was detailing to me how he has signed up for a bunch of them, getting all the different brands for the promotional price, then cancelling after the ‘cheap’ one. Not really a loophole so far. But then he did it again except to his work address with his work credit card. Another round of super cheap promotional prices and subsequent cancellation. Then got his roommate to do it too, to the same address but with a different name and credit card again, so round 3 (they shared the food). I don’t know if he’s still going and devising a round 4 or if he gave up now.

To be honest I feel a bit guitly posting his strategy here as I don’t want a whole lot of people copying and ripping off these places! But it’s pretty funny and took quite a bit of strategy on his part.

Oh, and one other trick he told me that I wouldn’t feel bad passing along is apparently if you ‘half’ sign-up and given them your email but don’t actually purchase and pay, they may send you an even better offer in a day or two to entice you!


9. Graham Pearson

A friend discovered that the Royal Mint were selling commemorative £5 coins by mail order for £5 each, with free delivery. The coins were legal tender. So he bulk-ordered them, paid using his credit card, then paid the commemorative coins into his bank account and repeated the whole process, at no cost to him (apart from the hassle); in practice he was getting a free loan until he paid his credit card bill.. The loophole was: by spending money using his credit card, he was earning air miles.


10. Kevin Howells

When visiting Vegas a few years ago my wife and I signed up for a cheap tour of the grand canyon. It was cheap because you had to attend a vacation ownership presentation afterwards. My wife became sick on the morning of the trip so I went in to cancel. I was told I couldn’t have a refund of my money as cancellation policy was 24 hours notice or forfeit money. I then asked if I could rebook for the next day instead . The lady said yes and went ahead and gave me a new booking receipt. As soon as I had the receipt in hand I went to the lady at the next kiosk and asked to cancel my trip – full refund received but the best value was the look on their faces.