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To kick off our celebration of 20 years of the SAMMY Awards, 2016 SAMMY winner Halley O'Brien checked-in with a few past honorees to see where they've been since their SAMMY, what they're up to now, and how often they wash their ski socks.

Read each full interview by clicking on the thumbnail of a SAMMY winner below. Just below the thumbnails, enjoy the entire story—which includes samplings of our interviewees' answers, blended with muse from Halley—as it was published in the January issue of SAM.

Thank you to all of the SAMMY Award winners for taking the time to be a part of this story. To everyone else, nominate a colleague, coworker, friend, or boss who you think is one of the industry's best current and/or future leaders. There is a lot talent in the mountain resort industry right now. Let us know who you think deserves a SAMMY in 2017. 

 CLICK ON THUMBNAIL FOR FULL INTERVIEW

>> CLICK HERE TO CHECK OUT THE COMPLETE SAMMY HALL OF FAME AND GET TO KNOW ALL OUR PAST SAMMY WINNERS

We’ve all had this moment: You’re on a plane settling in to your seat, or you’ve bellied up to a bar, and you start making small talk with a nearby stranger. After exchanging pleasantries, the stranger asks: “So, what do you do for a living?”

A coy smile creeps across your face because you know you’re about to blow this person’s mind. “I work in the ski business. I’m a [insert cool winter-related job here].” 

I absolutely love this moment. The stranger’s response is my favorite. It’s usually dripping with intrigue and sprinkled with a little jealousy. Rightfully so—our industry is freaking awesome. Not just because of the lifestyle and the fringe benefits, but because it’s filled with awesome people.

This year marks the 20th anniversary of SAM’S SAMMY Awards. Since the moment this annual recognition of the industry’s future leaders began, its purpose has been to highlight awesome people. No small task in an industry full of them. After 19 years, we wanted to find out what some of them are up to—and see if we’d made the right call.

As a recent (2016) SAMMY recipient (i.e., awesome person), SAM asked me to speak with several past SAMMY winners about their experiences and what their journey has meant to them. What I found was that no one’s journey was easy, but for all, it’s been worth it.

It Takes a Village

Let’s face it, not every day is a powder day, metaphorically speaking. Nonetheless, many of these SAMMY winners’ best days weren’t made by the conditions, but by the people they surround themselves with. Take Steamboat CEO and 2002 SAMMY winner Rob Perlman, for example. His best day was: “The first day I skied with my wife and two daughters. We had our first family ski day at Steamboat in 2007 while I was still at CSCUSA.”

Burton VP of global resorts Jeff Boliba, a 2004 SAMMY winner, shares Perlman’s sentiment. “My best day came on January 17, 2010, when we were at Park City Resort, and we got to ride the chairlift together as a family for this first time ever! Chloe was 5, Jacob was 8, and Jeffrey was 11. It was a great feeling, being able to take the chairlift together as a family and then ride around the resort in fresh snow.”

Clearly, family is a common theme. Our loved ones being all together on a chairlift, making turns, learning new things, laughing and playing together—that’s what makes this sport and industry so magical. 

The people we work with become family, too. Sierra-at-Tahoe GM and 2001 SAMMY honoree John Rice says, “I have many ‘best days,’ usually when I get news about the growth and promotion of one of our past employees who have moved upward and onward in their career.”

Bill Benneyan, who won his SAMMY in 2003 as marketing director at Mountain Creek in my home state of New Jersey—the same resort where he is now president—brought me back with a vivid description of his best day.

“Scene: Near midnight on a clear, cold starry night February 2004. The next morning, Mountain Creek will host the U.S. Grand Prix of Snowboarding. It was an audacious undertaking for a scrappy New Jersey mountain, requiring an extended all-resort effort, including the massive capital construction of the Superpipe … and it was magnificent.

“The actual event was secondary to the success of simply getting to this point. Standing under the lights in the empty venue, with the pipe shining wedding-cake perfect, was a fully satisfying moment of realizing the vision that had been defined nearly a year earlier. A small band of co-conspirators stand close together and quietly look up at the hill for a long time, and then silently turn and walk away. There’s nothing more to say. This night remains the best, for all the work each and every employee put into being the best hosts possible.”

I remember what that perfectly cut, Broadway-esque superpipe looked like under the lights. I drove up to Mountain Creek after a late afternoon college class for some night riding, and pulled over on Route 94 to watch in awe as pros like Shaun White practiced days before the Grand Prix. I was already in love with the act of snowboarding, but it was that moment I realized I wanted to be consumed by it. All of it.

It Takes A Mentor

Sometimes you click with someone on a deeper level. A leader who also recognizes something special in you. This person’s guidance helps steer you in the right direction, and toward the growth and opportunity ahead. All of this helps you to capitalize on your own potential.

I’m lucky, I have quite a few mentors in this business and beyond. One stands out among the rest, though—my favorite skiing partner, best friend, husband, 2011 SAMMY winner and founder of SNOW Operating, Joe Hession.

I asked him about his mentors, many of whom I know well and also revere. “I have been so lucky to work with so many amazing people. Charles Blier, Brian Fairbank, and Michael Berry, to name a few,” he says. “But if I had to pick one, it would be Frank DeBerry. Frank taught me a lot about the business and life. But most importantly, he taught me that great leadership can change lives.”

Jody Churich, SAMMY class of 2012 and COO of Powdr-Woodward, didn’t hesitate when it came to naming her mentor. “No question, [Powdr CEO] John Cumming. I’ve learned the very valuable and critical pieces of business acumen from him. He’s humble, honest, smart, and approachable. His story and true character is one that is grounded in a love for the mountains, sports, family, and the environment.”

In Jesse Boyd’s case, his mentors have been there long before he won a SAMMY in 2009 and became VP of operations for Peak Resorts. They’ve literally been there since day one. “My parents Tim and Missi are both ‘ski business’ veterans. I’ve learned the most from them, and they have supported me throughout the best and worst times,” he says.

He may now be the COO of Park City Mountain, but 2005 SAMMY winner Bill Rock credits Dan Fuller at Bristol Mountain for taking a chance on him and giving him his start in the business. Rock says Vail Resorts VP Tim Beck shared his wisdom, experience and vision about mountain planning and managing complex capital projects. “But, the most influential mentor for me has been Blaise Carrig, former mountain president for Vail Resorts. He brought me into the company, provided incredible leadership, and was truly committed to my success and development as a leader,” he explains. 

If Not Skiing, Then What?

If it weren’t for great mentors and the benefits that come with working in one of the coolest industries around, some may have pursued other career paths—including me.

I was a huge band nerd in high school—and I loved it. In fact, it almost materialized into a career in music education. Had I been a music teacher, my desire to connect with and entertain an audience would’ve been the same. The only major difference: my beanie collection would almost surely be far less impressive.

Rice, another “almost famous” musician, still dabbles in playing [including the occasional SAMMY Award night]. He jokes about his repertoire being devoid of hip-hop and house music, which probably limits his audience reach. I told him The Boss never has had a problem without hip-hop and house.

Perlman would get involved in America’s pastime: “I would be an usher in Scottsdale during spring training.” Seems to me an usher’s schedule would still leave time to be involved in snow. Well played, Perlman. Well played.

Cataloochee Ski Area president and 2007 SAMMY honoree Chris Bates would get his hands dirty: “If I worked in another industry, I would like to run a manufacturing plant. I know this sounds crazy, but I like seeing stuff made.” That’s not crazy at all, because he sees a lot of stuff, i.e. snow, being made every winter.

Who knew Bill Rock was a gear head? “I would work with and around racecars. It would be fascinating to be around a Formula 1 team or another highly focused, results-oriented, sophisticated racing program.” Highly focused? Results-oriented? Let’s be honest—he just wants to drive fast cars.

“I probably would have pursued law, but for as long as I can remember I wanted to work in the resort industry. Even while in college, I remember working on projects specific to marketing and public relations for ski resorts. I went to school in Malibu and all I could think about was snow,” says Snow Park Technologies VP and 2003 SAMMY honoree Genevieve Gunnarson.

Perks, Guilty Pleasures, and Laundry

One of the fringe benefits of working in this industry is you get a season pass to the mountain where you work, and usually some nice reciprocal bennies at other mountains. Between working at Mount Snow and Mountain Creek, then doing what I do now, the last time I purchased a lift ticket or a season pass was in college. I asked these SAMMY winners when was the last time they paid for a ticket or pass, too.

Rice made me feel better about my lack of lift ticket purchases. “Wow, I can’t remember … I am going to guess it was back in the mid- to late-’70s in Tahoe, when I was going to college. My roommates at Chico State were all skiers, and we had a few road trips back in the day.”

Gunnarson, on the other hand, makes me look bad. She purchased one just last winter because she didn’t want to call in a favor. *eye roll*

Whistler Blackcomb VP of business development and 2013 SAMMY honoree Rob McSkimming bought a ticket recently, too. “Ironically, I purchased a ticket to check Vail out a couple of years ago—it was really expensive.” #EpicPass. 

My favorite response, though, came from Matt Mosteller, who was awarded his SAMMY in 2000 and is now senior VP of marketing, sales, and resort experience for Resorts of the Canadian Rockies. “I never have. I was a fat kid whose life was saved by a chiseled-face, big-life-smile ski instructor who shared ‘freedom’ with me. Thanks, mom and dad, for making this all possible, as they paid for my first ‘racer pass’ and from there, the rest is ski bum history. (I can’t share all of my secrets.)”

We all have guilty pleasures, though I would argue mine is not something I feel guilty about. If your ski resort has a karaoke night, I’ve most likely hoarded the microphone and shamelessly subjected you to the entire Queen or Disney discography. I’m not sorry.

Churich considers her guilty pleasure a shaken dirty martini, while Gunnarson is wrapped up in all kinds of TV medical dramas. Ladies, I feel a girl’s night coming on.

Mosteller admits to losing his SAMMY award the night he won it. He thinks it went home with the cab driver. So, congrats on winning a SAMMY award, Mr. No Name Cab Driver. 

Because ours is a personable business, we asked how often everyone washes his or her ski or snowboard socks. I was pleasantly surprised by the answers. Nearly everyone confidently says they wash their socks after one day of using them—even after just one run. I’m not sure I believe them, but I’m not about to start throwing stones in this glass house, either.

Still, this is a practical matter. “If I wear a pair of socks for more than one day, bad things start to happen,” says Perlman. Amen to that. 

The fear of bad things happening clearly doesn’t faze Chris Bates: “I never wash my ski socks until spring.” Let this be fair warning; if you ski with Bates more than a month into the season, be far away when he’s changing out of his boots.  

Another exception to the daily washing of ski socks is McSkimming, who lets the climate decide his sock laundry schedule: “Depends on the freezing level—couple of days if it has been warm, double that during cold snaps.” 

Thoughts on the Future

I love how the open-endedness of this question leaves so much possibility for dreaming, innovation and creation. Our SAMMY winners ran with it.

Benneyan was reminded of an old Mark Twain quote: 

“’When I was a boy of 14, my father was so ignorant I could hardly stand to have the old man around. But when I got to be 21, I was astonished at how much the old man had learned in seven years.”’ 

Experience has taught Benneyan not to underestimate—and in fact to embrace—the younger generation. “Where some of us may have succeeded with confidence and passion, the new crop seems smarter, faster, and a great joy to teach, create, and share learning with every day,” he says.

Churich sees the way we communicate with guests, and who is communicating with them, as a next step—and one that’s happening now. “Marketing in the social media era is vastly different than it was just a few years ago. I have seen first-hand how effective a strong, relevant marketing team can power growth and thrive. Mobile phones are the new television sets. The future is about recognizing change as an opportunity to stretch and grow.”

Marketing has come a long way, but according to Gunnarson, it seems many are stuck in a rut of only marketing lift ticket sales, real estate, and equipment, rather than focusing on what’s important—the experience of skiing and riding, and the impact it has. “As hopefully a wiser and more experienced marketer, I hope that the future pushes us to find new and creative ways to share authentic mountain experiences with a broader audience,” she says.

It’s time to shift our thinking about how we market, sell, and fulfill our product. We’re in the middle of an exciting time when it comes to technology—from the way we create and consume content, to cloud-based solutions that help operate our business. There are so many opportunities for growth and maturation ahead of us.

Boliba views our youngest participants as key to growing our sport. “There is great opportunity for resorts to go after young, soon-to-be snowboarding kids that have snowboarding parents who can’t wait to introduce them to the sport. Snowboarding families are going to help us start replacing all of the Baby Boomers,” he predicts.

It was an absolute privilege getting to know each of these SAMMY winners, learning their stories, and taking a moment to reflect on my own journey. 

If one of my college professors told me I would get to create funny, feel-good content for one of the most beautiful, energizing, and invigorating industries, I would say … You’re damn right. Life’s too short to sit in a cubicle and only ski on weekends. In jeans. Which, for the record, I’ve never done, despite being from Jersey.