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 $200 to $250. Especially during the holiday season, generous tippers can push $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 $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 $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.