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The true story of how a pro big mountain skier became the owner/operator -- as in P-I-M-P -- of a million-dollar, high-country escort service. Yes, an actual pimp. [Originally published in the September, 2005 issue of Skiing Magazine]

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The Heidi Fleiss of winter doesn’t wear gold chains or drive a flashy car. He won’t touch cocaine or heroin. He’s loyal to his beautiful wife. A date for the two of them is a shopping trip to the organic market, maybe a movie at home on the plasma TV. For snacks they eat vegan cookies. He can’t stand cigarette smoke. No coffee. His pimp juice is filtered ice water with a slice of lemon. His high-rent apartment smells of peppermint. “Sorry about that,” he says. The mint is prescribed aromatherapy for the chronic hacking cough he caught while living in a dank basement during the South American Extreme Skiing Championships in Las Leñas, Argentina, in the mid ’90s. No apologies necessary. An entrepreneur shouldn’t have to apologize if his pad smells of peppermint.

Call him Bobby Fenton. God help the guy who calls him a pimp. He prefers pleasure broker. In fact, it’s Mr. Bobby Fenton to you. Like Heidi, Bobby trades in a very high-tier commodity. “Mine is the premium, most upscale escort service in the West. We have the most girls and the best girls for sure.” Yes, some of his clients you would recognize. But unlike Ms. Fleiss, Bobby is a professional athlete—a sponsored big mountain skier. And it’s because he’s a professional skier that he’s also a professional pimp.

The word pimp is not a joke, not a euphemism. Bobby’s not cool like a pimp: Bobby is a motherf#*king P-I-M-P. His employees are escorts. The escorts trade in flesh. They have sex with men (and other women) for money. He nets a healthy six figures every year. He’s broken fingers. He knows people who can break bigger things. He doesn’t want to have to call these people, but he’s got their numbers in his speed dial, next to the numbers of his old ski-equipment sponsors.

As a skier, Bobby wants what we all want. His dream is pure: a home in Canada and nothing to do all day but ski. A modest chalet, near the lifts, with room for friends to crash. The plasma television. His treasured photos of his grandfather Vincent—surrounded by olive trees in the old country. A harem of big mountain skis in the corner. Season pass. That’s about it. He’s got all the sunglasses he could ever wear from an endorsement contract back in his hucking days. “I haven’t lost my love for skiing,” he says. “I’m just kinda sidetracked for now.”

“Tomorrow’s gonna be kinda interesting,” he told me on the phone the day before he allowed me to shadow him on the job. “Actually,” he said, “every day is kinda interesting. I’ve gotta run an errand. You can ride along if you want.”

I was expecting maybe a black Escalade. A Hummer with a ski rack. But the pimpmobile is a family car with tinted windows and a trailer hitch so Bobby can tow his snowmobiles to the trailhead. Pantera on the CD player.

He’s wearing a $2,000 leather motorcycle jacket à la Captain America in Easy Rider over an untucked floral cowboy shirt. His jeans flare at the knee in an extreme that neither you nor I could get away with; on Bobby they’re impossibly cool. Black Italian motorcycle boots with silver buckles.

First we swing by his apartment. The gate is malfunctioning, so we drive in the out ramp, past security. UPS has delivered a parcel full of vitamins and herbal supplements. Bobby takes me into his office, where he sweeps several stacks of cash to the side, more money than I’ve ever seen in cash form in one place, money guarded by nothing more fearsome than a cat and the photos of Grandpa Vincent—who looks down on Bobby’s pad as if he’s keeping an eye on things while Bobby’s out.

He shows me—on his custom computer with the dual flat screens—his “girls” on his websites. The women are impressive, especially because the only thing that separates you from them is a credit-card number and a background check. A professional photographer shoots them in lingerie and there’s something of a Playboy biography for each girl—Candi likes “well-groomed men and red wine.” The girls’ working names aren’t important: There’s Candi and Julie, and Randee, there’s also a female “attorney” from San Francisco, in town for a special engagement, one weekend only. But it’s hard to concentrate on breasts that cost $300 an hour because I find myself trying not to look at that pile of money. “It’s none of my business,” I ask, “but how much cash is that?”

“About eight grand.” He considers how this must sound to the uninitiated. “I am so immune to seeing money.”

The word pimp hasn’t come up. If I can ask him about his cash I figure I can ask him about his occupational title. “What do you call yourself? Is ‘pimp’ too loaded?”

He nods. “I’m the owner. I used to do everything. Answer phones, book appointments, take money. I knew all the customers. Now I trade stocks.” He glances at the Nasdaq win-dow above Julie on the screen. “And today I’m losing money.”

It’s early January and a good season in his neck of the West, and Bobby has yet to get on the hill. He hasn’t had time to film a segment for a ski flick in a couple of years, but he keeps his hand in the game by testing skis for a ski magazine. “It’s funny,” says fellow tester and close friend, Scottie Ewing. “He’ll take off a little early every afternoon and show up a little late every morning.” Does Bobby resent that running a business that grosses close to a million dollars a year takes a chunk out of his skiing? “I hate everything about it,” he says of his entrepreneurial success. Then he catches himself. “Except the money.”

Now we’re off to collect some of that money from Angelina, in a procedure called a drop, as in money drop. But not before we make a stop for cough drops. We stroll through Walgreens—past the condoms and lubricants—on the hunt for sugar-free honey lozenges. Bobby is talking to me uncensored—and geriatric women are listening. He peels off a twenty from the wad he keeps in his front right pocket (today, payday for his staff, it’s $3,000 thick) and pays for two bags of cough drops and a bottle of springwater. Outside on the sidewalk is a homeless paraplegic. Bobby fishes in his pocket and drops a five-dollar bill in his cup. “Don’t spend it all in one place,” he tells him.
We wheel into an Embassy Suites in an affluent industrial side of the city. We’re here to meet Angelina. “Leave your notebook in the car,” he says. He grabs a ledger full of checks and a stack of credit-card receipts. We sit on the lobby couches and Bobby does some math. He is polite, professional, friendly even, but there is no mistake that this is a business relationship. For résumé purposes, Angelina is an advertising field rep.

“This is my friend. We’re going skiing.”

“Hi, friend,” she says. She is chewing bubble gum. Her daughter is in the hotel pool—it’s her birthday and Angelina is letting her john pay for the party.

Bobby stands up to get back out on his route. “Tell your daughter happy birthday.”

Angelina smiles. “I will.”

The incall is the workaday name for the place where some of Bobby’s girls go about their business. It’s a gray clapboard house just off a busy street in the heart of the city. In the driveway is Bobby’s ’59 Caddy with tail fins. There is a sign on the door of the house: doorbell is broken please knock. The place smells clean, less of perfume or incense than laundry detergent and sheets warm from the drier.

There isn’t any shopping going on. Girls are flitting about and lounging on love seats, but the Incall operates on a prior-appointment-necessary basis, no walk-ins, please. Some of the girls wear hot pants. There are miniskirts and a couple of less-than-street-legal Victoria’s Secrets. I’m assigned (through bashfulness) to the welcome mat between the washing machine (which never seems to stop) and the refrigerator. There is a notepad on the freezer door: things to do (Bobby has written make money). A microwave. A credit-card machine. A box of doughnuts and a scentless bouquet of supermarket flowers.

Sounds of the throes of lust are coming from the room where Cindy is hard at work—a client ordered the PSE (porn star experience) and now, apparently, has confused the PSE with some extra cuddling-’n’-kissing GFE (girlfriend experience). Bobby is getting anxious because Cindy is going over her hour, grinding for free, twenty minutes of gravy now.

“Charge her,” Bobby’s wife says. “That’s what I would do.”

He thinks on his feet, quickly decides to call Cindy’s cell phone. His wife goes to the red room door to listen. No ring. Just grunts and yodels. All the while Bobby, who needs something to occupy his hands, is impatiently folding towels.

Okay, that’s it—he’s starting toward the parlor when the customer scurries out the front door just in time. In a petite black negligee, Cindy taps into the kitchen sweaty as a tennis pro, opens the oven door, and retrieves a pair of jeans.

Bobby is relieved, but incredulous. “You keep your shit in the oven?”

“Yeah—I don’t want somebody stealing a $150 pair of jeans.” She grabs a doughnut and heads back to the red room to collect the cash, which as protocol requires was placed on a side table prior to the interlude.

“I was gonna bake some cookies,” Bobby says. And that’s it. He defuses the situation with humor, still retains his pimphood; everyone is happy; everybody gets paid.

Bobby isn’t abusive to his girls. but he does know wrath, number four on the Seven Deadly Sins list, just ahead of lust. “When I was a teenager I had a terrible temper that mellowed out when I moved to the mountains. Now it’s back and five times worse. I’m sure that once I’m done with all this shit, and I am living an easy, relaxed, fun life, I will return to that balance. But for now I am not a person that takes to getting angry very well.”

Bobby describes for me how he was recently charged with felony assault on a john who was stalking one of his girls. He had the girl set up a phony encounter so Bobby could talk some sense to the guy. But the john copped an attitude. “I couldn’t believe this guy was talking back to me. Here he is, a married man with kids, stalking a working girl. Idiot. I told him to be reasonable and go back to his wife and kids. The guy started cursing me, calling me a ‘pussy pimp.’ When he tried to grab the girl I snapped and beat the shit out of him. The girl took off and the cops came and I got charged with felony assault. But the guy didn’t show up in court so I walked. What was he going to do, explain to the judge who I was and what we were doing?

“I do not like being an angry person,” he says. “But it comes with the job.” Which is one of the reasons why he promised his wife he’d be finished with the escort biz by early summer. Sell high, trade a few stocks, and by winter Bobby may be out of the business and back in the mountains for good. Maybe. “I make more money than the highest-paid executive in the ski industry,” he says. “I know I do. And I have a lot more freedom.”

Bobby eats sparingly and on the run. Out the door of the Incall and around the corner on Main Street is a pizza joint. He uses the place as a satellite office. The brothers throwing dough behind the counter smile and nod when he walks in. “Some days I conduct employee interviews in here all day. I think they know what’s going on but they don’t hassle me. I can only eat so many slices of pizza. So at Christmastime I gave them a nice bonus.”

Bobby tells me—over a slice of cheese and veggie—about interviewing girls. “I hate telling girls they’re too old or too fat,” he says. “So I try to schedule question marks in the afternoon. ‘Look, I can only take two girls and I hired them this morning.’ That sorta thing.” But I can tell the white lies get to him. He’s not a natural, wishes everything could be aboveboard and in the open. “I can’t stand the business. I hate it. I could make more money if I paid attention. I’m just so over it. I just want to ski again.”

If his escort business were “legit”—his word—it would be worth upwards of $1.5 million. This includes the websites, the client list, the escorts, and two incredibly important employees, Kat and Mindy, the phone girls who set up all the appointments and keep track of the escorts like taxi dispatchers. A good phone girl makes $600 a week plus bonuses, but is worth as much as the client list, which includes many attorneys, CEOs, physicians, athletes, and musicians. “We’ve got a congressman,” he says with pride. “A family man.” Nearly all are carefully screened repeat customers; Bobby has their personal information on file, so they tend to behave like gentlemen. When Bobby sells (to another local businessman), he is expecting a decent percentage of the $1.5 million. “I’ve never met him,” Bobby says about the potential owner. “And I never will.”

bobby grew up in a traditional italian family on the east Coast and made frequent trips to Vegas with his grandfather, an avid gambler. When he was 14, his immediate family moved to California. He played high school football—and didn’t get his his first taste of skiing until he turned 17. “I just fell in love with it. It was one of those years in Big Bear when it snowed a lot. It’d be raining hard in the city. I’d sneak my skis into my car and ditch school. But I still kept my grades up. I don’t know how.” He’d go on to squat 400 pounds, bench press 275, and drop out of college after two years, during one of which he played offensive line for the varsity. His future, though, was being forecast by his lust for skiing.

“I literally got snowed in at Big Bear—the roads were closed. I was standing at the urinals next to a guy. He says, ‘Crash with us, we’ve got a big house.’ They were ski instructors. They wanted to teach better—PSIA stuff, really gay shit. I was a dead-on intermediate. I skidded my turns.” Turns out, one of the instructors was from his neighborhood and taught him to ski—on inline skates. “On Rollerblades it’s impossible to skid a turn.”

The next season he applied to the ski patrol in Mammoth and got on. “I lied about my skiing ability,” he says. “I had all this confidence. I went from being a really shitty intermediate skier in the fall of ’89 to going pro in ’91.” That winter he drove his Scirocco to a mountain town famous for its burgeoning extreme-skiing movement and lived in a tent for three weeks before settling in. That’s where his skiing—and moonlighting—took off.

Bobby would go on to model winter clothing for big-name casual-wear companies. He would ski for Warren Miller and Steve Winter. Nike shot him on snowshoes for a full-spread magazine ad for its ACG line. Adidas used him in a Kobe Bryant display.

But for all except a handful of top professional freeskiers, the lifestyle is steep, even with sponsorships. For several years he made just enough money to keep doing it, but found himself having to hassle an eyewear sponsor for a hundred-dollar residual.

In 1999, he and fellow pro skier Ewing produced a party for one of their ski friends. There was illegal gambling, complimentary booze. And girls—call them moonlighting strippers. He was good at this sort of thing and moved to Vegas and enrolled in dealer school, graduated with honors, and got a job at the Sahara on the strip. That led him into the underground casino business.

Soon after, he made contact with a cocktail waitress who dabbled in the adult industry as a dominatrix for hire. She knew a lot of girls. The relationship was symbiotic. The girls appreciated Bobby’s being straight with them; he took home a lot of Benjamins. In short order the escort service dwarfed the gambling operation.

“I’m not a washed-up pro skier who wants to string my career along. Worrying about sponsors, not getting paid enough or on time—that taints the purity of what you’re doing. When I go back to my adopted hill and ski there’s no pressure. I enjoy it like I did when I first got the powder bug. I can see why people take vacations. Except when you’re on vacation you can’t stop thinking about having to go back to work. My goal is to not have to go back to work.”

The key to that is diversification. In addition to running his escort service, Bobby produces after-hours parties with a friend that are the hip activity here in a city that will remain unnamed. The party names and locations change. Bobby shows me the guest book for an event he threw when a ski show came to town in 2002. It reads: anybody who’s anyone in the ski industry is here. The secret: girls. “Without girls,” Bobby says, “all you’ve got is a bunch of guys standing around drinking beer.”

When you’re lucky—and cool—enough to be invited to one of these parties, it will be explained to you that there is zero tolerance for drugs. Talk too much about the location and “you’ll be dropped out back and we’ll beat the shit out of you.”

The safety of the girls is paramount, and bobby goes to bat for them when he needs to. He smashed a stalker’s headlights. He went to court to support a girl during a date-rape trial; she had no one else. He fires escorts (even high-earners) on the spot if he hears about them doing drugs.

The 15 or so girls Bobby employs are his “field reps.” He keeps one third of all income (that’s a hundred bucks an hour for those of you keeping score). A girl might make six calls in a good day. The girls pay for their website promo photos, which can be subtracted from their take. There are packages available, including a three-day ski rendezvous. Bobby provides the women, but lift tickets, lodging, and ski rentals are up to the john. When you visit one of Bobby’s escorts and decide to put it on your Diners Club card, the bill your wife gets is going to read $300 for a media company. “One day I was working the phones and this chick calls. ‘What kind of business is this?’ she asks. I paused. ‘It’s a media company. We do advertising.’ ‘Look,’ she says. ‘We’re engaged. Wouldn’t you want to know?’ I told her.”

Bobby rewards loyalty, though he doesn’t always get it. Girls occasionally take off with his investment—the client list—and start freelancing. It’s a violation of trust and street rules. And a pimp who takes it is a pimp who’ll soon be out of work. “So I start fucking with her business. I call and schedule fake appointments. I call the hotel where she operates, tell them what’s going on, and they kick her out.” Bobby doesn’t enjoy this, doesn’t want to have to do this. But he does it for the job, like a plumber unclogging toilets. More than the threat of getting busted, this is the cause of his work-induced stress. “Sometimes what I’ll do when I get frustrated is I’ll go home and look at my pile of money. I have a safe. Looking at the money is kinda like a morale booster.”

we stop by a tattoo parlor to talk with winston. he’s tall, his eyebrows are ink, boasts Maori tribal tattoos, wears a gray suit and tie. He’d have to take out his cheek piercings at airport security. Bobby introduces me. “This is my friend Jon from New Mexico. He’s in town to ski.” If a guy is okay with Bobby, he’s okay with Bobby’s people. His reason for a meeting with Winston, he says, is to drop off one of the new pay-per-use cell phones. I’m still not sure that meeting Winston wasn’t a subtle message for me, for any business acquaintance of Bobby’s. You do not want to be not okay with Bobby.

“Nice to meet you, Jon.”


Winston is a crowbar man. A fixer. He solves problems. Bobby has a new one. A guy skipped town owing him nearly $20,000. “I hear he moved to Miami.”

“Moved to Miami,” Winston says. “Or is visiting Miami?”

“I don’t know. You know anybody in Miami?”

“Sure,” Winston says. “I’ll make some calls.”

“We’ll talk on Sunday.” Bobby works Sundays.

Bobby also has designs on art.

“Oddly enough,” he says, “this was way before any of this.” He’s queued up a videocassette and is pointing a remote at the plasma TV. There’s a sonic assault of Pantera-like metal and then a skier who goes by the name J-Bird explodes onto the screen. He gets face shots in a narrow chute and then is popped against the rock wall face-first. “J-Bird,” Bobby says, “is an incredible skier who had a terrible day.” But, Bobby agrees, the scene makes for a titillating intro. “When you think about it, you can pimp anything. Laundry soap, anything.”

The movie—at this point it’s still a trailer, a teaser—is called Snowpimps. Bobby started this project in 2001. He declined money from legitimate ski sponsors because he didn’t want to sacrifice vision. “I just thought, I’m gonna document what I do: Hook up with chicks, go to strip clubs, and ski. That’s it.” The skiing alternates with shots of girls seducing metal poles, face shots, more poles. Most of this footage was taken in the Beehive State. “This one chick got really freaky on us while giving us lap dances. In Utah of all places.” He smiles. “So I don’t know. It’s a good concept. Ski films think they’re edgy. They have no idea where the edge is.”

It’s midnight—bobby’s five o’clock. but first he has some payroll business and we pick up the phone girls, Mindy and Kat. Mindy is a goth chick and peppers her talk with
f-bombs while telling funny stories, except when she answers the customer phone and then she turns into Donald Trump’s personal receptionist. We go to a bar and grill, but only for the grill. There’s water with lemon and Bobby orders the skinless chicken breast pasta, green salad, no dessert. He peels off some payroll cash and Mindy scratches some figures in her ledger book. Talk is of which girl is getting augmentation surgery, which girl can work an extra day, which girl had some personal business and clocked out early.

He’s good at what he does, so how can Bobby just abandon the profession? When it doesn’t snow and his stocks are down and his competitive instincts are up, won’t Bobby be tempted to supervise a couple of beautiful Canadian girls as they separate international tourists from the money in their trousers? “Once I am out of the business, I am out. No going back. … Although I was recently hired as a consultant for a couple who want to start an escort agency.” Bobby charged $10,000 for the consultation. “I set them up with the necessary paperwork, how to keep from getting busted, hooked them up with the proper dirty attorney, how to hire girls, everything.” Still, he’s emphatic. “As for being in the business again, no way. I know plenty of ways to make money now that I have money.”

We’ve pulled up at the incall, behind the Caddy and the garage full of discarded stained and threadbare mattresses, and Bobby smells of honey cough drops and is telling me over Pantera and the breath of the defroster about a particular powder day last year. He skied bell to bell by himself. That day put everything in perspective. There was an innocence about it. It was like being 17 at Big Bear again. No crew shooting ski-porn from an $800-an-hour helicopter. No having to throw air for competition judges. No pimping himself. Then the door of the Incall swings wide under the flaccid glow of the 40-watt porch light. A male silhouette bounds down the steps and skips across the street—careful not to slip on the sidewalk ice—and disappears like a ghost in the pall of midnight. Bobby grins. “Another happy customer,” he says, and the conversation turns back to snow.

[editor ’s note: On June 1, Bobby reportedly sold his escort service and moved to Canada. His cough has since cleared up.]