In the late 1800s, as gold miners moved through the Colorado Rockies, they came upon the would-be ski resort of Aspen, with Mount Sopris as its crown jewel. The land was rich, but also sacred to the indigenous Ute tribe, who cursed their visitors out of despair. Anyone who slept in the shadow of Mount Sopris would be doomed never to leave.
Today, Mount Sopris casts its shadow over a gold mine of a different kind: a tangle of 375 world-class lifts and pistes, frequented by an A-list crowd (Michelle Obama, Antonio Banderas, Paris Hilton, Mariah Carey) still unable to escape the destination’s grip. Nobody appreciates that better than Aspen Mountain’s 135 resident ski instructors—a coterie of Olympians, world-famous alpinists, and members of the National Alpine Team who comprise the Harvard of skiing.
“There’s a fair bit of Darwinism at play at Aspen Mountain,” says Andy Docken, general manager of the Aspen Mountain Ski & Snowboard School. To survive, instructors must adapt to their clients’ complicated needs, both on and off the slopes.
As I realized quickly during a stint on Docken’s team, hosting the best of the best in every field—from New York financiers to Hollywood royalty—is just as much of an expertly coordinated dance as zigzagging down a black diamond. Sure, it’s fun to slay pow at one of the world’s most elite resorts, but I was also taking clients shopping for artwork the price of a house, dodging flurries of airborne Champagne corks, and busting midmountain trysts at the end of each shift. Here’s what I learned about everyone’s favorite winter pastime.
At most five-star hotels around the world, porters and receptionists can learn a lot about guests based on their cars, luggage, or clothes. So how do you make an analysis when your client’s tumbling toward you in a puffy parka and ski boots? “You can tell a lot about how someone’s going to ski by the way they walk in their gear,” says Marc Fernandes, one of Aspen Mountain’s ski school pros.
A seesawing heal-to-toe motion in your boots suggests you’ve got some alpine experience; clomping or marching makes you look like a novice. The way you carry your skis is also telling—pros have nicknames for the different configurations. Hoist them in an X shape in front of your chest and you’ll be called “The Decapitator” (and not in a cool way). Sling your pole straps around alternating ski tips, and you’ll have mastered the slick “Oklahoma Suitcase” method.
Instructors get the lay of their moguls—the business, tech, and real estate variety—on the 15-minute gondola ride up the mountain. Is my neurotic Wall Street banker client looking for a taste of Colorado chill, or are they looking to take advantage of every New York minute? Some self-professed experts have egos that need stroking; others appreciate being humbled by veteran powder-shredders.
Sometimes clients don’t even want to ski. Since instructors are often willing (and eager) to introduce clients to plugged-in friends around town, they tend to do double duty as both high-altitude and high-society guides. “I’ve seen colleagues accompanying their guests on shopping sprees at the art galleries instead of heading up the mountain,” says Fernandes.
Most Clients Want a “Fun Young Guy”…
Docken estimates that the typical ski resort makes 80 per cent of its business from group lessons, but Aspen Mountain only offers private instruction—at a starting rate of US$820 a day. Most guests pre-request teachers based on referrals; the rest use a survey-like form to find the perfect match.
“People are awfully particular about their special requests,” says Olga Lawson, the on-snow coordinator at Aspen Mountain. Among the common asks? “Blond instructors, please,” “Olympic medalists only,” or “Someone who likes to drink.” Once, a sixtysomething skier split up with her coach midmountain, marched back down to the ski school, and asked for a new pro “who was loose.”
Even still, the most frequent request is simple on the surface: People want “a fun young guy,” or as Lawson interprets it, a handsome Australian or New Zealander in his 20s or 30s. (Women want to date them; men want to bro out with them.)
“We also get tons of requests for instructors with French accents,” says Lawson, adding that many clients want to practice their foreign language skills before heading to Courchevel or Megève. She jokes, “It’s like two lessons for the price of one!”
The Unspoken Rules of Attraction
Asking for photos before picking an instructor is a no-no at the Aspen skiing school (though it’s frequently attempted). And yet, there’s still an OkCupid-like quality to pairing students and teachers. Lawson and her team spend an average of 45 minutes on the phone getting to know each skier to find the perfect lid for every pot.
But just like in matchmaking, some clients are undateable. Have a habit of hitting on female pros? Chances are it’s highlighted and circled in your unwritten file, and you won’t be paired up with one again.
The worst transgressors even get little nicknames, like DHD. Dick Head Dad hasn’t just been barred from two Aspen hotels for being famously difficult, he’s also paid $685 for a half-day of guiding only to ditch the instructor after the first lift ride. (Being with an instructor enables you to cut the line.) Now when his requests come through, all the instructors tend to be busy washing their hair.
The Best-Regarded Celebrities Are Ones Who Like to Ski
In the staff locker room, celebrity names are dropped with the same excitement or indifference as a real estate titan or Wall Street trader—the only thing the pros care about is whether their clients like to ski.
A certain former first lady is beloved among instructors for her genuine affinity for slaloms. As for the current presidential couple? Not so much. Everyone still snickers about the massive blowup 30 years ago between Donald Trump and his first wife, Ivana, when she discovered he had brought along his then-mistress Marla Maples on their ski holiday. Legend has it that Ivana, who claims to have been an alternate for the Czechoslovakia Olympic team, followed him down the mountain skiing backward, berating him for his marital transgressions.
A lack of discretion is the easiest way to get mocked. One socialite, derided by Cam Short and his fellow ski valets at The Little Nell—Aspen’s most luxurious hotel—has a knack for loudly broadcasting her drug-addled exploits in crowded rooms. (“It probably helps her brand,” he reckons.) There’s the pop diva who insists on swishing around in a red leather bustier with her six brutish bodyguards—even in below-zero temps. Rebel Wilson scored jeers when she decided midmountain that she was done skiing for the day and insisted on a ride down from the emergency toboggan. And then there’s Jeff Bezos, who furrowed brows when he recently skipped a ski day for a shopping spree … on horseback.
Instructors Don’t Want to Catch a Whale
The instances of unruly guests or matches made in hell are fairly rare. Not so rare? Having skiers book an instructor for the entire season. Some families like to nab two—or even four! According to Aspen Skiing Co., the record-setting reservation blocked out three pros for 100 days ($250,000); second place went to a group that retained a personal skiing quartet for about two months (US$184,000).
This pattern is most common among high-ranking members of the finance world, who offer their instructors to family members and colleagues just like they would a summer house. For instructors, this sounds like a pretty sweet deal. But actually most Aspen pros aren’t keen on being winter sports geishas. If their deep-pocketed patron decides to take one ski season off to spend the winter in Tahiti, it can send business plummeting—a risk that’s usually not worthwhile.
How to Predict a Major Windfall
Officially, tipping is off the books, and it’s hardly what motivates most instructors. But it’s an essential part of the gig, offsetting Aspen’s high living costs and contributing to exorbitant dry-cleaning bills—getting drenched in Champagne or hot-boxed in a gondola are common occupational hazards. (Welcome to Colorado!)
A hundred bucks is the unspoken minimum for a day; on Aspen Mountain, the average tip hovers around US$200 to US$250. Especially during the holiday season, generous tippers can push US$1,000 a day—and while most instructors will say life’s too short to spend a lousy day with a fat wallet, two weeks of dull days can be enough to survive on all summer. After all, jackpot payouts, spoken about in hushed tones, hum to the tune of US$50,000.
Noncash payouts can also be a delightful byproduct of long-term relationships. A Saudi prince once gifted an instructor a Jeep. Other clients have shown their gratitude with heli-skiing vacations in the Southern Hemisphere, trips to the Super Bowl, and invitations to weddings and bar mitzvahs. One instructor is even the godfather to his client’s children.
At the Biggest Veuve Vendor in America, Most of the Champagne Ends Up on the Floor
Cloud Nine, the famously rowdy midmountain restaurant, offers surprisingly robust business development opportunities for rookie instructors. Some ski bunnies explicitly hire help to get there in one piece; others need guidance to get home safely.
“I’ve been told by our distributor that we sell the largest quantity of Veuve Clicquot in all of North America for an individual establishment,” boasts Tommy Tollesson, Cloud Nine’s manager. He also claims that Cloud Nine earns the highest revenue per square foot of any restaurant in the U.S., even though it’s only open 135 days a year. (Based on average per-person spend and capacity, he likely makes $10 million a season from his little hut; the top-grossing American restaurant, Tao Las Vegas, reports $42 million in annual sales but has roughly 44,000 square feet to its name.)
Here’s how all that money gets spent. During each of Cloud Nine’s daily parties, an average of 120 bottles of Veuve will be cracked open. Most ends up on the floor … by way of the ceiling. By the end of the season, 1,000 cases will have been squeegeed off the walls. Booking more than a month in advance requires a minimum spend of $300; that means plenty of seafood towers, caviar, and bubbles on top of the standard, $49-per-person raclette feast.
It helps that people are here to indulge. During my stint, Tollesson arranged 100 bottles of Veuve for a single client who was going through a rough divorce. (The bill for that alone: $13,000.) “None of it will end up in his mouth” Tollesson told me. “He only drinks Dom Perignon.”
Aprés-Ski Is Crazy Fun, But the Private Club Scene Is Even Better
Ski-and-be-seen is the absolute rule in Aspen’s private clubs. What’s more fun than blowing by an Oscar-winning actress whose name wasn’t on the guest list? It happened to one instructor in the off hours.
Hidden beside the Sundeck canteen at the top of Aspen Mountain, the eponymous Aspen Mountain Club is an haut monde enclave capped at 350 memberships. Joining the club literally means replacing a member who has died or aged out of skiing, assuming you can also gather four references and cut a check for the US$250,000 induction fee. Easy.
If that’s a bit too formal, the Caribou Club in the center of town is more like an Ivy League secret society, with a dance floor, dining hall, and lounge. “The Bou” has more than 1,000 members—“everyone from past presidents to ski bums,” says communications director Krissy Bills. Lucky for you, weekly passes can be had for $500 and up.
Ski Pros Have Secret Societies, Too
In most places, ski pros last two or three seasons before moving on. Not Aspen. Remember the Curse of the Ute? Instructors stay here for decades, which means that likeminded cliques—or gangs—start to form. Yes, gangs.
Think of them less like Bloods and Crips and more like the Sharks and the Jets—breaking out into slalom turns instead of jazz hands. “There’s a tribalistic quality to them,” says ski instructor Ted Mahon. “They’re like college fraternities, each with their own reputation.” Names like the Bell Mountain Buckaroos, Powder Sluts, the Umbros, and Flying Monkeys all find their way into regular conversation in Aspen. The Freaks are currently the fastest group on the mountain; unsurprisingly they’re mostly made up of millennial-age Instagram aficionados. Want to pledge? Remember: These are professional ski bums. They’re too relaxed for that nonsense. (But if your street cred checks out, you might get an invite to the gang’s morning runs.)
Learning their lingo can help you fit in. Aspen gang slang goes beyond industrywide vocab terms like “yard sale” (noun: when you wipe out so hard that all your gear falls off) and refers more to local terrain. “We have a lot of secret names for mountain areas that are passed down like folklore,” says Julia Hedman, one of Aspen Mountain’s youngest instructors. Following her lead might mean taking Copper to Yankee Stadium to the Nose—though none of these are listed on official trail maps.
Also popular: using celebrity names to inform secret codes. According to Hedman, a John Wayne Bobbitt is when you ski a certain cutoff (get it?), and the long face of Aspen Mountain is called SJP. Poor Carrie Bradshaw …
Ski Patrols Are EMTs and Bouncers All Rolled Into One
For a sport that involves speeding down frozen mountainsides, surprisingly few people sustain serious bodily harm while skiing. On their busiest day this season so far, Aspen’s 18-person ski patrol reported just nine incidents—despite having more than 4,000 skiers on the mountain.
Thirty-three-year veteran ski patroller Art Nerbonne mostly sees knee and shoulder injuries; he’ll get occasional calls about altitude sickness as well. “Intermediate skiers are the ones getting hurt most often,” he says. And some people need rescuing over and over. “I’ve actually saved the same guy from a heart attack on two separate occasions, two different years,” Nerbonne says. “It was like a little reunion.”
As for the nonmedical aspects of being a ski patroller? “Every morning we punch in at 7:30 a.m. and check for obstacles and avalanche risks,” he says. At day’s end, they morph into bouncers, kicking off sloppy revelers stumbling through their last runs. “We’ve found all sorts of strange things during the last sweep,” says Nerbonne. “Even two people having sex.” Hope they didn’t get frostbite …