Extreme Mileage Hacking: Creative Ways to Earn Flier Miles

By Jason Steele. Last updated 8 December 2016. 3 comments
Photo: Luis Argerich

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Most people have a frequent flier account of some sort, even if they haven’t given it much thought lately. Others have made collecting points and miles not just their hobby, but their passion. While the rest of us sit in awe of extreme couponers when they save a few hundred dollars off of their groceries, these extreme mileage hackers regularly earn tens of thousands of dollars worth of travel. They fly around the world in first and business class, stay in suites at luxury resorts, and barely pay a fraction of what these services would normally cost.

I recently attended a weekend seminar where many of the top mileage collectors in the world gathered to tell their stories and share their techniques. Of all the travel award enthusiasts that I met, three people told stories of extreme mileage earning that were so mind-boggling, they held this well-traveled crowd at the edge of their seats. (See also: How to Maximize the Value of Your Frequent Flier Miles)

The Pudding Guy

Have you ever done anything so cool that a Hollywood director decided to include it as part a movie? That is what happened to a Californian named David Phillips. In 1999, Phillips learned that the Healthy Choice company was offering a few hundred frequent flier miles for the purchase of each of their food products. He realized that by buying pudding, their least expensive item, the miles he earned would be worth more than the product itself. He ended up purchasing $3,380 worth of pudding from distributors across the state. As he ordered the pudding by the truckload, some distributors would ask what he needed it for. Slyly, would just mumble something about Y2K. Upon receipt of the pudding, he donated it to the Salvation Army, which in turn provided volunteers to help him process the paperwork. He thoroughly documented everything he did, making copies of his entire submission.

Although the people at Healthy Choice initially claimed not to have received his voluminous submission, they quickly relented in the face of his evidence, and even enlisted him in a publicity campaign. In the end Phillips earned over 1,250,000 miles from airlines such as American, Northwest, Delta, and United Airlines, as well as a tax deduction for his charitable contribution. This is enough for ten first class trips to Europe. If this story sounds familiar, then you have probably seen the movie Punch Drunk Love, where the character played by Adam Sandler does this exact same thing.

Mr. Pickles

Another amazing speaker at this convention prefers to remain anonymous, but goes by his online pseudonym Mr. Pickles. In 2009, he achieved some measure of notoriety when an acquaintance of his spoke to a reporter and disclosed his obsession with ordering coins from the United States Mint. Although most people would find coin collecting is a perfectly normal past time, Mr. Pickles is no average collector. He enjoyed ordering the new commemorative one dollar coins which are only worth their face value. He used his credit card to place the order under their Direct Ship program, which offered free shipping in order to encourage the circulation of these unpopular coins. Upon receipt, he would immediately deposit the coins at a local bank and use those funds to quickly pay off his credit card balance. Doing so earned him frequent flier miles at no cost to himself.

So far, this story is not very remarkable. Many people, myself included, ordered a few thousand of these coins from the Mint to use around town while earning a few miles on our credit cards. On the other hand, Mr. Pickles ordered well over one million coins during the life of the program. To find banks that would accept deposits of thousands of coins a day, he mapped out every branch location within 50 miles of his home. He would then tell the managers what he was doing and be extra nice to the bank’s tellers. Although the coins were delivered and deposited in rolls, each bank would eventually grow tired of regularly receiving hundreds of pounds in coins. Often, he would bring the staff pizza, donuts, or coffee in order to put off the inevitable day when they told him to take his business elsewhere.

Once his story and those of others like him was leaked to the mainstream media, the United States Mint decided it would no longer accept credit cards for the purchase of coins at face value. Before that happened in mid 2011, Mr. Pickles earned over 1.2 million miles, enough to travel around the world in business class four times.

Steve Belkin

It was appropriate that Steve Belkin gave a closing address to the conference, as he was one of the most engaging and enthusiastic speakers there. For him, earning a mere million miles is just child’s play. Belkin, who goes by the name BeauBeau on various travel forums, treats frequent flier miles like a Wall Street investment banker treats stocks. He has figured out exactly how much each company’s points and miles are worth, and he will heavily invest his money in any scheme that allows him to acquire them at rates that are below his pre-determined values. When an airline offers bonus miles for traveling on a certain route, he doesn’t just buy himself a ticket, he pays for other people to fly as long as they agree to let him use their miles. He told stories of paying Asian farmers to fly around Thailand and American students to travel through Europe, so he collects bonus miles being offered on particular routes.

Like the Pudding Guy, Belkin is constantly looking for opportunities to make purchases that earn more miles than the item is worth. In late 2009, he and I both purchased large quantities of the TrackItBack Lost & Found Recover Service, when we learned that US Airways was temporarily awarding 140 miles per dollar spent on this product during a holiday promotion. According to their website:

TrackItBack provides its customers with uniquely coded ID labels that come in various sizes, shapes, and languages. Customers affix the ID labels to their personal items and register them online at TrackItBack's website or by phone. When an item is lost, the ID label instructs the finder to "Return for Reward" and TrackItBack facilitates the return of the lost device at no charge to its customer. The finder is rewarded with a pack of TrackItBack product and any optional cash reward that the owner of the item has chosen to provide.

After thoroughly reading the terms and conditions of the offer and consulting with others online, my wife and I eventually decided to purchase $3,000 worth of this product. We carefully considered the possibility that US Airways would not honor the terms of the deal, but we were reassured when the company responded to customer’s concerns in public online forums. Although we eventually received a 475,000 US Airways miles, Belkin earned millions of miles to be used by his family and friends, potentially worth tens of thousands of dollars more than he paid.

Although less tasty than pudding, I love the TrackItBack system. Better yet, I was also able to realize a tax deduction by donating my surplus product to a non-profit organization. Most of it went to the NTEN, the Nonprofit Technology Network, which was able to distribute it to other worthy charities that needed such a tracking system. After our tax deduction was taken into account, we essentially purchased miles for approximately one half of a cent each. We later redeemed 360,000 of these miles for our family to fly in business class to Italy and Israel this fall. I donated the remainder of the miles to my parents who traveled to visit family in a Williamsport, Pennsylvania, a town whose airport only has service from US Airways.

What We Can Learn

I have been earning miles my whole life, but really started spending time researching award travel within the last four years. Although I was previously aware of some of these stories, I was still thrilled to meet these people hear their experiences first hand. But I also tried to learn something from each of them. For example, the Pudding Guy only received his million miles because he kept meticulous records of his compliance with the terms of Healthy Choice’s offer. This is a great habit no matter how many miles are at stake. Likewise, you should always save your boarding pass in case your mileage is not credited. In addition, Steve Belkin’s experiences show how you can always find creative ways to earn miles without ever leaving the ground. Finally, Mr. Pickles proves that just being extra nice to the people you meet will encourage them to go out of their way to help you out. If there is one lesson that I learned from everyone I met at this conference, it is that the only limit to the amount of points and miles that can be earned is that your own determination and creativity. There is no doubt that these opportunities continue to present themselves, and I will do my best to share them with you as soon as I learn about them.

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Extreme Mileage Hacking: Creative Ways to Earn Flier Miles

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Meg Favreau's picture

Punch Drunk Love is one of my favorite movies -- I love that Barry's pudding plan was so true to life.

Guest's picture

This is some impressive planning ahead and time management. While I love to get free stuff, but I also try and balance how much time I put into it. Other than using a rewards card, I don't see the value in all that time into getting miles. At this phase in my life, the amount of travel needed to actually use the miles is not an option. Although you can use some miles on products, they always seem to be more miles versus money. Personally I would rather spend time on increasing income, investments and saving on daily purchases.

Nora Dunn's picture

I took advantage of the same frequent flyer mile promotion with TrackItBack! It was my own start to travel hacking with frequent flyer miles. Now, when I fly long-haul, I do it in business class, and for (WAY) less than the price of an economy ticket!