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)

 

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.

 

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.

 

 

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.