Schlappig in an upgraded room during his travels. (Photo: @onemileatatime/Instagram)

Ben Schlappig is what you might call an airline rewards savant.

He’s been outsmarting airlines by manipulating their own rewards programs to fly around the world (on his own) nearly for free since he was 13 (his dad reasoned it was better pastime than smoking pot). At 16 he flew across the Pacific six times in one trip (Chicago, Osaka, San Francisco, Seoul, and back), and by 17, he’d flown 500,000 miles.

These days, at the ripe old age of 25, Schlappig traverses the world spending little or none of his own money — it is his life’s work. His business, PointsPros, helps book trips to get the most out of their frequent-flyer miles. Then, last year, when his lease ended after a break up, he decided to get rid of most of his belongings and live out of a suitcase full-time, which he details on his blog One Mile at a Time. “I’m very fortunate in that I do what I love,” Schlappig told Rolling Stone. “An airplane is my bedroom. It’s my office, and it’s my playroom.”

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So how does he do it? Since he was a teenager, Schlappig has been part of a community of like-minded frequent flyer nerds whose pursuits are known as the “Hobby” — these enthusiasts devote their time to using frequent flyer miles, rewards credit cards, and airline loopholes to fly for cheap or for free.

From his adventures in Hobbying, Schlappig learned tricks of the trade, including these:

1. Choose one airline to earn elite status, even it means starting off with a few paid-for flights to create loyalty. Because elite status comes with lots of perks and upgrades. (Schlappig chose United, but then was kicked out of the program a few years ago.)

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2. Sign up for as many of the best rewards credit cards as you can. (One particularly clever trick among Hobbyists is to use these credit cards to buy dollar coins, then use the coins to pay off the credit card bill immediately — so you’re actually buying nothing but reaping the rewards anyway.)

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Even after having flown well over four million miles, Schlappig says he still loves flying. (Photo: @onemileatatime/Instagram)

3. Exploit the airlines’ imperfect algorithms. Maybe not for the novice, but according to coding Hobbyists, it’s shockingly easy. “The people who run these programs are idiots – and we’ll always be one step ahead,” Schlappig once said at a Hobby gathering.

4. Get bumped — strategically. In 2011, Schlappig told The New York Times that he had snagged “well over $10,000” in United flight vouchers in three years by using Federal Aviation Administration (FAA) data to book flights that were most likely to be overbooked and therefore bump passengers. (Of course, this revelation is also what got him kicked out of United’s elite program.)



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It’s a lot for the layperson, but not for Schlappig. These days he says he spends about six hours a day flying, and says he has no plans to stop: “The world is so big, I can keep running. At the same time, it makes you realize the world is so small.”

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