Flying High

By Gary Leff 02/11/14

It might not be an addiction, but my obsession with frequent flier programs comes pretty close.

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Hi. My name is Gary, and I'm a Miles-holic. You know, frequent flyer miles. I will go to extreme lengths to earn them. They’re valuable, they can be used for free travel. But it’s more than that. I check my account balances every morning. I scour the internet looking for the next ‘fix’—how I’m going to earn more miles, in a big way. And I get a special thrill out of getting a great deal on miles, earning a lot of them, and doing so at the lowest cost possible.

Some would say that I’m more of a borderline case, because I live a well-adjusted life. I’m normal, even, except that I jet off to the Maldives every year, I visit Paris for New Year's and Australia for Christmas. I’m writing now aboard a Cathay Pacific first class flight from Hong Kong to New York, that I redeemed American Airlines miles for. I’m drinking Krug champagne, and just placed my lunch order—caviar and balk salmon ‘tsar nicolaj’ followed by a prawn main course. I have pajamas to change into and a bed to sleep in. Only I want to keep the pajamas, to save them in my collection, along with the amenity bag they’ve given me. I have hundreds. I don’t use them, but I HAVE TO have them.

I’ve progressed to occasionally helping people redeem their miles for trips. That means I don’t just think about earning miles, I think about redeeming them. All the time. I spend almost all of my waking hours thinking about frequent flyer programs.

And I'm working with someone just as addicted as I am. Steve Belkin discovered loopholes in frequent flyer programs that allow you to assign the benefits of your account to your employer. So why not get someone to do the flying for you, earn elite status and international upgrades, without actually setting foot on a plane? And if it made sense to do, it made sense to find the cheapest way to do it. Back then you could buy flights inside Thailand for about $8 apiece. And if it made sense to do on a small scale, why not do it a hundred or a thousand times over? Steve became a labor broker in Northern Thailand, hiring disabled Thai rice farmers to fly 5 round-trips a day out of Chiang Rai near the Golden Triangle.

This was a great scheme that allowed him to earn 8 international upgrades for $800 plus the cost of labor. The only problem was that the Golden Triangle area is the opium capital of the world, and Steve had a visit one day from the DEA. They thought he must be the stupidest drug runner in the world, with mules doing 5 trips a day out of that area with no luggage. He showed them his spreadsheet and one of the agents was even interested in signing up for the upgrades, but ultimately the run-in with law enforcement convinced Steve this wasn’t a good project.

Until, that is, he discovered that Air Canada’s top elite frequent flyers could book any Air Canada seat they wanted with points—even business class to Australia, any time, and for no extra points. So why not hire New Zealand college students to fly to Europe for the summer… and assign the benefits of their accounts to their employer (him)?

Back in 2002 you could buy 32 subscriptions to Inside Flyer and earn enough Starwood Starpoints that—transferred to Qantas—could be redeemed to fly the British Airways Concorde. In that way a round-trip on the Concorde cost only about $1200. Some people donated their subscriptions to libraries and took a tax deduction.

On Christmas morning 2009 I sat at my computer in my room at the Hilton Garden Inn in Yakima, Washington. I couldn’t do ‘family time’ because the deal in front of me was too good. Skip the holidays; if I made purchases from five different retailers participating in the Dividend Miles online store, then I would earn a 250% bonus on all the miles I earned. And a company that sold stickers to help you find and recover lost items was giving away 40 miles per dollar spent. That meant I could earn 140 miles per dollar with the bonus, or buy miles at just over 7/10ths of a penny apiece. That meant tickets to Hong Kong in business class for under $500 round-trip!  I helped several friends earn a total of 16 million frequent flyer miles that day, and I shut down the company’s American Express merchant account (for good).

Until recently you could buy dollar coins from the US mint and pay with a credit card. They offered free shipping. In other words, you could put money on your credit card, and the purchases would earn you miles. The money would get delivered to you, and you could take it to the bank and use the funds in your account to pay off the credit card. The transaction cost you nothing but your time online and going to the bank (as well as explaining to the bank teller what you were doing with all those boxes of dollar coins, and enduring strange stares from your neighbors and other bank customers). And you could earn all the miles you wanted. Some people did over $2 million worth.

I’m not ready to admit this publicly, but I might even have ‘used’ a microlending charity to earn miles. I’d buy gift cards at an office supply store, using a credit card that earns 5 miles per dollar there. And I would use the gift cards to make charitable loans. Those loans get paid back, I might even withdraw the money… use it to buy gift cards for the miles, and start the cycle over again. I tell myself I’m doing good in the world, but the truth is that I’m just thinking about my miles. In the movie Up in the Air, George Clooney's character orders as much food at meals as he possibly can because his employer will pay for it and he doesn’t want to lose out on earning miles for the purchases. Don’t tell my boss, but…

There’s a true story on, memorialized in the Adam Sandler film Punch Drunk Love, about the guy who bought Healthy Choice pudding and earned over 1 million miles in the process. He donated the pudding to a soup kitchen and got their help removing the UPC codes he needed to submit for the points. 

It’s a true story, the man’s name is Dave Phillips, and he introduced me to an offer several years ago where you could earn 10,000 British Airways miles just for test driving a Jaguar. The key, he pointed out, was that British Airways has family accounts where you could have 4 family members pool their miles. So four test drives would mean 40,000 miles that could be used by a single person. Put another way, “Test drive a Jaguar, get a free round-trip ticket to Europe!”

My wife thinks I have a problem when I am reading about miles instead of talking to her. I tell her that I make up for it when I spend the miles to take her to Paris. And since she’s stayed with me all of these years, she must think I’m healthy, too!

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Gary Leff is a travel writer.

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Gary Leff is a travel writer and one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. You can find Gary on Linkedin or follow him onTwitter.