Tuesday, July 21, 2015

Up in the Air: The Man Who Flies Around the World for Free

The boarding procedure has barely started at Chicago O'Hare, and Ben Schlappig has already taken over the first-class cabin. Inside Cathay Pacific Flight 807 bound for Hong Kong, he's passing out a couple of hundred dollars' worth of designer chocolates to a small swarm of giggling flight attendants. The six suites in this leather-bound playpen of faux mahogany and fresh-cut flowers comprise the inner sanctum of commercial flight that few ever witness. They're mostly empty now, save for two men in their twenties who seem even giddier than the flight attendants. The two stand to greet him. "This is so cool!" exclaims one, and soon Schlappig is ordering champagne for everyone.

This sort of thing happens to Schlappig nearly everywhere he goes. On this trip, his fans will witness Schlappig's latest mission: a weekend jaunt that will slingshoot him across East Asia — Hong Kong, Jakarta, Tokyo — and back to New York, in 69 hours. He'll rarely leave the airports, and when he does he'll rest his head only in luxury hotels. With wide ears, Buddy Holly glasses and a shock of strawberry-blond hair, Schlappig resembles Ralphie from A Christmas Story if he'd grown up to become a J. Crew model. Back beyond the curtain in business class, a dozen jowly faces cast a stony gaze on the crescendos of laughter and spilled champagne — another spoiled trust-fund kid, they've judged, living off his parents' largesse. But Schlappig has a job. This is his job.

Schlappig, 25, is one of the biggest stars among an elite group of obsessive flyers whose mission is to outwit the airlines. They're self-styled competitors with a singular objective: fly for free, as much as they can, without getting caught. In the past 20 years, the Internet has drawn together this strange band of savants with an odd mix of skills: the digital talent of a code writer, a lawyer's love affair with fine print, and a passion for airline bureaucracy. It's a whirring hive mind of IT whizzes, stats majors, aviation nerds and everyone else you knew who skipped the prom.

Schlappig owes his small slice of fame to his blog "One Mile at a Time," a diary of a young man living the life of the world's most implausible airline ad. Posting as often as six times a day, he metes out meticulous counsel on the art of travel hacking — known in this world as the Hobby. It's not simply how-to tips that draw his fans, it's the vicarious thrill of Schlappig's nonstop-luxury life — one recent flight with a personal shower and butler service, or the time Schlappig was chauffeured across a tarmac in a Porsche. But his fans aren't just travel readers — they're gamers, and Schlappig is teaching them how to win.

"I'm very fortunate in that I do what I love," says Schlappig, stretching out in an ergonomic armchair as we reach 30,000 feet and just before the mushroom consommé arrives. In the past year, since ditching the Seattle apartment he shared with his ex-boyfriend, he's flown more than 400,000 miles, enough to circumnavigate the globe 16 times. It's been 43 exhausting weeks since he slept in a bed that wasn't in a hotel, and he spends an average of six hours daily in the sky. He has a freewheeling itinerary, often planning his next destination upon hitting the airport. Just last week, he rocketed through Dallas, Dubai, Oman, Barcelona and Frankfurt. Yet for all his travel, it would be a mistake to call Schlappig a nomad. The moment that he whiffs the airless ambience of a pressurized cabin, he's home.

"An airplane is my bedroom," he says, stretching to reach his complimentary slippers. "It's my office, and it's my playroom." The privilege of reclining in this personal suite costs around $15,000. Schlappig typically makes this trip when he's bored on the weekend. He pays for it like he pays for everything: with a sliver of his gargantuan cache of frequent-flyer miles that grows only bigger by the day. Hong Kong, he says, is his favorite hub, and "the only city I could ever live in." The 16-hour trip has become so routine that it's begun to feel like a pajama-clad blur of champagne and caviar — or, in Schlappig's terminology, a "two-hangover flight."

As the sun descends over the polar circle, a recumbent Schlappig loses himself in a 2 Broke Girls marathon playing on a free-standing flatscreen. "The fact is, we are beating the airlines at their own game," he said last year at a gathering of the Hobby's top talent. "The people who run these programs are idiots." Then he paused. "And we'll always be one step ahead of them."

by Ben Wofford, Rolling Stone |  Read more:
Image: Bryan Derballa