The boarding procedure has barely started at Chicago O'Hare airport and Ben Schlappig has already taken over the first-class cabin. It's Valentine's Day and, on Cathay Pacific Flight 807 bound for Hong Kong from the United States, he's passing out 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 20s 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 a hero to an elite group of obsessive fliers whose mission it is to outwit the airlines, 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 and aviation nerds.

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 non-stop-luxury life - one recent flight with a personal shower and butler service, or the time Schlappig was chauffeured across the tarmac in a Porsche. But his fans aren't just travel readers - they're gamers, and Schlappig is teaching them how to win.

“There’s a joke: I’m not heterosexual, I’m not homosexual, I’m aerosexual”

"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 650,000km, 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. 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 pressurised 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 about US$15,000. Schlappig typically makes this trip when he's bored on the weekend. He pays for it like he pays for most things: with a sliver of his gargantuan cache of frequent-flier miles that grows only bigger by the day. Hong Kong, he says, is his favourite 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 pyjama-clad blur of champagne and caviar - or, in Schlappig's terminology, a "two-hangover flight".

"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. "We'll always be one step ahead of them."

Schlappig wasn't so much introduced to his fixation as he was raised by it. Born in New York, he became obsessed with aeroplanes as a small child, endlessly reciting aircraft models and issuing flight announcements from the back of his parents' car.

"Benjamin was always different than my two other boys," says his mother, Barbara. "Teachers told me, 'He's ahead of everything.' He was bored."

At 13, he discovered the website FlyerTalk, a massive free-for-all forum of all things airline, where users meet to strategise over deals, test for cracks in the bureaucracy and share the spoils. There, Schlappig found a global community playing a massively complex game set upon three basic components.

One of the fundamental steps a Hobbyist can take is choosing an airline to compete for top-tier loyalty status; Schlappig chose United. Nothing was free up front - the object of the game was a return on investment. A Hobbyist doesn't spend unless he can get the same or greater value in return. It took Schlappig about a year to master the dozens of convoluted techniques, exploiting mistakes in ticketing algorithms and learning the ins and outs of the frequent-flier programmes airlines had created after deregulation in the US, in the late 1970s. The second leg of the game is credit cards - collecting and cancelling as many as possible, and deploying a series of tricks to reap the reward points that bank-and-airline-card partnerships would virtually give away. As he delved deeper, Schlappig learned about a third level, a closely guarded practice called Manufacture Spend, where Hobbyists harness the power of the multitudes of credit cards in their pockets. Airline-affiliated credit cards award points for every dollar spent, so, over the decades, Hobbyists manipulated the system by putting purchases on credit cards without ultimately spending anything at all. At its simplest, this included purchasing dollar coins from the US Mint with a credit card and immediately using them to pay off the charge. Schlappig read one detailed post after another that insisted Manufacture Spend was the only true way to fly for free - like sliding a coin into a slot machine and yanking it back with string.

Eventually, the best way he learned to visualise this bureaucratic gamesmanship was to see it as a series of table games on a sprawling casino floor - and if the airlines were the house, Schlappig realised, the Hobbyists were the card-counters.

Exceptionally bright and equally motivated, Schlappig saw a way of convincing his parents: by showing them how they could visit family in Germany paying less in first class than they would to fly economy. From there, his parents grew to fully indulge his obsession. By the time he was 15, they were delivering him to the airport on Saturdays and retrieving him on Sunday nights at baggage claim.

"It was an interesting hobby," says his dad, Arno, as cicadas chirp outside the St Petersburg, Florida, condo their son bought them after the blog took off. "I said, 'Hey! Keep it up. It's better than smoking pot.'" On a typical weekend, Schlappig would hopscotch to the West Coast and back - Tampa, Chicago, San Francisco, Los Angeles, never exiting the airports. "Some of his friends knew," Arno says. "The teachers I don't think were aware of it."

Schlappig attended an all-boys Catholic school, where he struggled to fit in. "When his homework was done, he went back to his room on FlyerTalk," Arno recalls. "And he just posted and posted." Hobbyists say the game takes years to master. But at 16, Schlappig became the first known member to fly across the Pacific Ocean six times in one trip - Chicago, Osaka, San Francisco, Seoul and back again - in July 2006. By his 17th birthday, he'd logged half a million miles. That year, Schlappig was elected to FlyerTalk's governing TalkBoard; in 2009, he ascended to the post of vice-president, second to Gary Leff, now 40, one of the Hobby's most popular bloggers.

"I was scared at the beginning," Barbara says. "I mean, what mom lets her son fly at such a young age around the country, right?" US air marshals wondered the same thing when they once hauled Schlappig off a plane after glimpsing his baffling itinerary, demanding to speak to his parents.

BEN WAS THREE WHEN his eldest brother, Marc, just days after his 14th birthday, was killed in a horrific accident. He'd been riding a jetski his parents had rented when a drunk driver struck him with a boat. The family was devastated, and for young Ben the loss was particularly hard. His father, who worked for a bank, was home only on weekends.

"Marc had been like a father to Ben," Barbara says. "He was everything."

For the next year, Ben refused to go to preschool and, when he did, the teachers couldn't stop his screaming. Eventually they told Barbara to keep Ben home. On the worst days, Barbara did the only thing that seemed to calm her son. They drove to the airport and sat together in silence, watching the aeroplanes take off and land.

"His eyes were all sparkled," she says, remembering their day-long outings.

Eventually, the family relocated to Tampa, in Florida, where Ben attended grade school and discovered his obsession.

Throughout high school, his jet-setting accelerated, as he crisscrossed the country on United Airlines. For the first time, he had found a place to belong. When Ben was 16, he earned elite status, brandishing his Premier 1K card wherever he flew. He found he connected socially with Hobbyists far better than with classmates, and he started organising meet-ups around the US, advertising them on FlyerTalk.

In the autumn of 2007, Schlappig enrolled at the only college he applied to, the University of Florida, without having visited. He was bored almost instantly, filling the emptiness with travel and FlyerTalk. The following February, Schlappig launched One Mile at a Time, and he began speaking at airline-sponsored events, wonky consortiums where airline employees and frequent flyers can mingle. It was at one such gathering, at San Francisco International, in 2009 that the 19-year-old Schlappig met Alex Pourazari, a teenager who'd become a member of Schlappig's rapidly growing following.

"I was such a fanboy - so embarrassing," recalls Pourazari. "I still have that adoring email I sent him. It cracks me up." The two quickly became best friends, together plotting ever-more-dizzying flight routes to challenge each other's game.

"We were like brothers," says Pourazari, who now lives in Seattle. "It was more like we were best friends than anything. Then we both realised that we were gay. And we grew up together."

They logged hundreds of hours in the air together, rarely leaving airports. This practice - called "mileage running", or flying incessantly on steeply discounted flights to accrue frequent-flier miles - is a foundation of the Hobby. Schlappig and Pourazari took their first mileage run on Valentine's Day 2010. On one run, they hit seven airports from Tampa en route to Hawaii, turning straight back without even breathing the air in the parking lot.

For the next year and a half, as their friendship grew into a romance, they continued to perfect their techniques; one favourite was called "flight bumping". At the time, airlines often oversold their flights, and passengers who voluntarily gave up their seats got a free ride on the next one, plus a US$400 voucher. Oversold flights are supposedly chance occurrences, but using software popularised in the Hobby for collating obscure Federal Aviation Administration data, Schlappig and Pourazari became masters of predicting when flights would bump.

Soon, Schlappig began studying the rules of so-called apology vouchers. As a conciliatory gesture for anything broken on a given flight, United offered coupons to passengers worth US$200 or US$400. Every time he boarded a plane, Schlappig looked for something broken - a headset or an overhead light - and racked up the coupons.

"When a system can easily be exploited, it's tempting to push it to its limits, for the game of it alone," Schlappig says. "Especially combined with the arrogant confidence only a teenager can have."

During his senior year, he carelessly bragged to a New York Times travel reporter that he had amassed more than US$10,000 in bumping vouchers. A few weeks later, Schlappig says, in April 2011, he received a certified letter from United, cheerily informing him that because he had taken advantage of the system his frequent-flier account was permanently suspended. He was banned from flying, he recalls the letter saying, unless he paid the company US$4,755 - the amount it claimed as losses through Schlappig's techniques.

"I mean, how do you define 'taking advantage of'?" Schlappig asks, passing a hand towel back to a doting attendant as we fly over the South China Sea. "Was I seriously inconvenienced to the tune of US$200 every time my audio wasn't working? No. But they create the system." (United officials will not comment on the record on Schlappig's case, other than to say, "We don't take steps toward limiting member engagement with the programme unless we see acts of fraud or other serious violations.") Schlappig has repeatedly offered to send United a cheque but has had no response.

"While it doesn't justify anything, I think it became more about the game in those years," he says. "And while I was far from the only one playing, I thought I was the best."

Just weeks after receiving his banishment letter from United, Schlappig graduated with a degree in marketing. He stayed in Tampa, still dating Pourazari by aeroplane, and after going on a few corporate job interviews, he decided to take a chance and turn the Hobby into a career. That summer, with Pourazari on board, he incorporated PointsPros, a consultancy that helps customers build itineraries out of frequent-flier miles.

"We were just plane geeks, plain and simple," Pourazari says. He stops midsentence on the phone to call out the models of planes as they pass over his balcony. "There's a joke: I'm not heterosexual, I'm not homosexual, I'm aerosexual."

With their inscrutably complex rules, the airlines had created a market of hopelessly confused holidaymakers, and PointsPros immediately found itself in demand. After a year of dealing with a staggering workload and a long-distance relationship, Schlappig decided to move in with Pourazari, in Seattle. During the move, in the autumn of 2012, Schlappig met with fellow Hobbyist Tiffany Funk, and he recruited her to join the company. She arrived to find the pair on the brink of a stress-induced implosion.

"Things grew really fast," recalls Funk, 31, who lives with her husband in San Diego. "And Ben was totally not prepared."

After a year, Schlappig's relationship with Pourazari completely unwound, and Schlappig found little holding him to the ground.

"At that point, I was like, 'Screw it,'" he remembers. "I decided I might as well do this full-time." In April last year, at the end of his lease, he walked into Seattle-Tacoma International Airport. He hasn't come down since.

IN 1979, AS DEREGULATION transformed the airline business from a monitored public good into corporate America's new Wild West, an ad executive named Bill Bernbach hatched a marketing scheme that would change air travel forever, by incentivising sporadic customers to become returning fliers. Bernbach proposed to his client American Airlines that it reward customers with free travel. Two years later, the first frequent-flier programme was born, and the rest of the industry scrambled to join the arms race.

The Hobby followed soon after, pioneered by a triumphant menswear clothing manager and moonlighting aviation nut named Randy Petersen. In 1986, Petersen founded an aviation magazine called InsideFlyer with US$800 and no publishing experience.

"I'm not a business guy, I'm a surfer-dude guy," Petersen, 63, says, wearing a bright-yellow trucker hat over wild bleach-white hair. "I kind of figured out how to earn free travel when these programmes were just starting out."

Early editions of Petersen's magazine featured stories on deals from obscure carriers; instructed fliers on how to duck airline countermeasures; and showed readers how they could win 1,000 free miles by subscribing to magazines such as Esquire. By 1993, InsideFlyer had 90,000 readers. Two years later, Petersen took the community online as FlyerTalk.

Almost at once, FlyerTalk became the singular worldwide hub of airline nerds, and today it claims to have more than 500,000 members. FlyerTalk was where Schlappig launched One Mile at a Time. Immediately he became one of the Hobby's biggest stars and, according to his friends, a millionaire. His revenue comes from three sources: impression-based ads on the blog; the PointsPros consultancy; and "affiliate marketing", which means collecting a commission from credit-card companies each time a card sign-up originates from his blog. Schlappig admits that affiliate marketing gives him a vested interest in the very companies that many Hobbyists game.

Amassing a large cache of credit cards is essential to Manufacture Spend. No topic of discussion produces more worried glances or tighter lips - a code of silence is central to Hobby culture. Manufacture Spend reveals a fundamental but overlooked truth about frequent-flier miles: they've become, in essence, a currency. In 2012, a European Central Bank paper classified airline miles in the same category as bitcoin, citing a 2005 calculation by The Economist that valued the global stock of frequent-flier miles at more than US$700 billion. But if miles are currency, then airlines are like central bankers who can constantly change the rules, devalue the points and close accounts at will.

Schlappig is giving me this economics lesson while he waits in the spa of the first-class Virgin Atlantic Clubhouse in New York's JFK Airport. He is chatting through a complimentary massage, enjoying the elbow in his back from a plump spa therapist and straining occasionally to sip his dry gin with crème de mûre. She chats with him, smiling, and asks how he's been - Schlappig knows almost the entire staff here by name, and he schedules his globe-trots to make a pit stop here every few weeks.

He's treated equally well by flight attendants, who are among his rowdiest fans. When a chief steward recognised him on one superluxury carrier, Schlappig stepped into his onboard shower to find a bottle of Dom Perignon on ice waiting for him. On a recent international flight, an attendant manoeuvred an unwitting Schlappig into an empty row, administering what he delicately terms a surprising and unwanted hand job.

Despite his success, many in the Hobby think the days of hopscotching across the globe are numbered. Paranoia is the lingua franca of all Hobbyists, and now is a good time to be pessimistic. Earlier this year, Delta and United both switched to revenue-based reward systems: frequent-flier miles are now awarded by total dollars spent, effectively ending the practice of mileage running. Schlappig seems unconcerned.

"I've been at this for 10 years," he says. "And there's not a single year where I didn't hear at one point or another, 'This is coming to an end.' But every year, we find new opportunities."

For some, the game has evolved from a wonkish pastime into an ends-justified obsession with beating the airlines - less Rain Man, more Ocean's Eleven. While the game's traditional methods remain technically legal, these Hobbyists use tactics that routinely violate airline terms and conditions, techniques that can span a gradient from clever and harmless to borderline theft. (Schlappig concedes that he pushes the rules but insists he is careful not to break any laws.) Take the practice of "hidden-city ticketing" - booking your destination as a layover, like buying a ticket from Point A to Point C, then sneaking away at B - or "fuel dumping", a booking technique that confuses the price algorithm to deduct the cost of fuel from a ticket, often at an enormous discount. In this strange and risky world, black markets exist where brokers buy and sell miles, and Hobbyists pay others to fly in their names.

They also write custom code to hunt the web for "mistake fares" posted accidentally by airlines and hotels.

"These people have the ability to cause serious financial harm," says Henry Harteveldt, an industry analyst and former airline loyalty-programme manager. Harteveldt has spent decades studying the Hobby and the airlines - a war of attrition, he says, between two equally obsessive tribes with very long memories. "No one's hands are clean in this fight," he adds. "The gamers have dirt on their hands, and airlines have dirt on their hands." For now, the Hobby's principal advantage remains its size - tiny enough, he says, to avoid the attention of the airlines' gargantuan bureaucracy. But for Hobbyists tempted by dreams of mastering the game and beating the house, Harteveldt offers a warning. "Ultimately," he says, "the house always wins."

For more than 30 years, the commercial airline industry has been mulling how to solve a problem like the Hobby. "The airlines basically thought they could manage it down," Harteveldt says. "Today, they'll never be able to shut it down entirely." For years, a de facto stand-off ensued, with each side equally invested in keeping the travel-going public none the wiser.

In multiple interviews, airline representatives insist that Schlappig and FlyerTalk represent little more than a portal for passionate customers. But mention the Hobby's darker side - anonymous players around the world who use secure servers and private email groups to communicate - and they turn grave.

"If any members of these groups were particularly effective, they could have a catastrophic effect on an airline," says Jonathan Clarkson, director of Southwest Airlines' rewards programme.

A new perception has grown that it might be airlines, and not Hobbyists, that are in over their heads. If true, it's a development that wouldn't lack for poetic justice, says Tim Wu, a professor at Columbia Law School and a frequent writer on airline policy.

Before deregulation, the price for a given seat remained fixed. But today, says Wu, the range of prices customers might be charged for the very same seat is spectacularly wide. "They made a normal activity suddenly like going to a casino. A lot of people get shafted. But it also creates an opportunity for people who can break the system and live like Schlappig."

IT'S AFTER MIDNIGHT IN Wan Chai, and after crossing the Pacific on another 16-hour flight, raccoon-eyed and hair mussed, Schlappig looks like he has just been let out of school for the day. He's riding a buzz equal parts champagne and coffee, and he has found himself in his favourite city once again. Tonight, a cab has dumped him curbside at the Grand Hyatt.

"There's something indescribable in the air, here," he murmurs.

Schlappig has barely stepped into the hotel's glistening VIP lounge when someone shouts, "Is that who I think it is?" Two stout men and a blonde see a beaming Schlappig heading towards them, all hugs and first names. In the Hobby, a run-in like this is an occasion for yet another bottle of champagne.

One hour in, and the three are swapping stories about the time they met the teenage Schlappig at a Hobby party he organised in Sausalito, California. The woman at the table is a corporate lawyer from New York, one of the Hobby's few female participants.

"I met him, and I was like, 'Oh, my God,'" she recalls. "'This kid is, like, in high school.'" Each person at the table has concocted a story for their co-workers or friends about where they disappear to on weekends. But this evening, they've found one another in Hong Kong. Schlappig spills champagne on himself as he raises his glass for a toast: "So much for lonely, right?"

The next morning, Schlappig is fighting off a hangover as he trudges through Hong Kong International for a flight to Jakarta. He sighs.

"I don't really physically associate anything with being home," he says, "but this is about as close as it gets." Bag in tow, he pauses to gaze at the sprawling indoor pavilion. "The Hong Kong airport, the Virgin Atlantic Clubhouse at JFK - I do feel at home there," he muses. "It's weird."

Somewhere over the Indian Ocean, though, for the first time, he betrays a note of sadness in his blank smile.

"Absolutely, it's isolating," he admits. "There are nights where it's 3am in Guangzhou, and you're like, 'Oh, I could actually be in LA having fun with friends.' And there's nothing to do here."

Or anywhere: his trip reports betray a theme, in photo after photo devoid of human companionship: empty lounges, first-class menus, embroidered satin pillows - inanimate totems of a five-star existence. On our next flight, a seven-hour run from Jakarta to Tokyo, Schlappig tries to get himself motivated about the champagne selection, holding forth on the best meal pairings with a US$200 bottle of Krug. But there are no fans waiting to surprise him here. An elderly Japanese couple sleep in the corner. Otherwise, the cabin is deserted. Many air carriers long ago made the judgment to let first-class suites go unfilled, to protect the marketable aura of exclusivity.

"I do what I love," Schlappig whispers, perhaps more to himself, trying not to wake the couple. "You have to understand: this has always been my passion." His words trail off, and he closes his eyes.

Rolling Stone

 

FLIGHT CLUB …

Right of reply

Ben Schlappig wasn't happy with the article in Rolling Stone magazine published here in amended form. "I don't travel for free, and don't 'game' or 'take advantage' of the banks and credit card companies," he tells Post Magazine. 

In particular, he says, the article misrepresented him when it comes to manufactured spend. "I don't participate in manufactured spending, really have no idea how it works, and never write about it or endorse it," he says. "I operate within the rules of the programmes, and encourage my readers to do the same."

Schlappig posted a response to the original article on One Mile at a Time that voiced his irritation and explained what he "actually stands for":

  • "Loyalty programmes and travel credit cards are incredible. They allow me to have amazing experiences I couldn't otherwise afford. That being said, it's far from free. Where do we even begin?

"There's a huge time investment needed to truly understand miles, points, and loyalty programmes. I have someone do my taxes because I don't really understand the tax code. Could I understand taxes if I wanted to? Absolutely. But it would take a lot of time to learn, and it's just not something I'm passionate about. You need that passion to get into this hobby. You can't say, 'I want to travel the world for free tomorrow … show me how to do it.'"

  • "You'll never travel the world for 'free'. There's no such thing. Even if you travel exclusively on points, there's an opportunity cost to every point you earn, and beyond that, at a minimum there are taxes, fees, etc. There are other bloggers who promote travelling being free. I'm not one of them, and never have been."
  • "There's a difference between gaming loyalty programmes and maximizing them. I would rather redeem my American AAdvantage miles for travel in Cathay Pacific first class than at the expensive award level for a domestic flight. Conversely, I'd rather redeem my British Airways Avios for travel on short-haul domestic American flights than for Cathay Pacific first class. That's simply a function of the relative strong points of a programme."