If there’s one thing experience has taught Dennis Eshbaugh and Brian Fairbank, it’s that you can’t be successful in the ski industry without the support of others—and support comes in various forms.

Like many leaders in this industry, Eshbaugh, GM of Holiday Valley, N.Y., and Fairbank, whose company operates Jiminy Peak, Mass., Bromley, Vt., and Cranmore, N.H., both were introduced to skiing by their families at a young age. In part, that sense of family—and shared sense of humor—has made them great friends and confidants. As they have throughout their many years knowing each other, neither is afraid to ask what the other thinks. Nor does one miss an opportunity to play a prank on the other.

While Eshbaugh and Fairbank both scoff at retirement, they also understand the value of what the next generation brings to the table. We sat down with them to talk about how they got here, what they’ve learned, and what the future holds.

Share, if you can, the first time you remember thinking, ‘This is what I love.” How old were you; where were you?

Brian Fairbank: I was six years old and growing up in Buffalo, and my dad took me to Emory State Park. It was an upside down rope tow area, and he said, “All you have to do is put your skis in this wedge and you’ll be fine.” I did it and went probably 150 feet and tumbled, tumbled, tumbled. And I don’t know why, but I fell in love with it. By the time I was 12 I had so much passion for it, I never did get it out of my blood.

Dennis Eshbaugh: I was 14 and I knew I wanted to ski, because I wanted to be like my older brother who was five years ahead of me. My close friend and his sister took me, using my brother’s equipment, of course. I think it was the second trip I was hooked. Even though I was probably going five miles per hour, I couldn’t get enough of the sense of freedom, speed and challenge.

At what point did you think, “I really want to be here” in this industry?

Brian: When I was 12 my parents took me to Lake Placid, and I was fascinated by it. A guy named Charlie Draper, who ironically used to run Holiday Valley a long time ago, was very gracious with me. I subsequently sent him back a topography map of Blue Mountain south of Buffalo with a bunch of questions, and he sent me a response back. That was in 1952, I think. But because he leaned in, and got me even more intrigued with something I was already passionate about, I really wanted to get involved as a skier and became an instructor at Blue Mountain when it opened. I was so fascinated with this and hooked on it, it just ended up influencing my life.

Mr. Draper said that any time a kid takes the time to want to talk about this industry, he finds the time. It goes to show how you can enhance someone’s life just by taking a few minutes. He did it for me. That’s amazing.

Dennis: My first ski industry job was at a university ski slope and we had a rope tow and some equipment. I got what I thought was the best job in the world. I was an instructor, a ski patrolman, a rental shop guy, and I got to run the ski lift as well. It was an incredible introduction to the sport.

Unfortunately, I didn’t last long. We had some bindings that were absolutely unreleaseable in a day and an era when that had already changed—it was 1972. So I had a rather direct discussion with my academic advisor that ran the ski slope and said that it was unacceptable we were breaking two legs per 50 skiers. And, uh, well that was the end of my first job in the ski industry.

I ended up at Holiday Valley in 1974-75 I believe.

It takes a special person to have a long and successful career in this industry. What traits do you see in yourself and in those you admire who have done it a long time?

Dennis: I think the first thing you have to have is understanding the “Wait; what?” question. You have to have curiosity. You have to be able to start progress; find the beginning with, “Can’t we?” or “How can we?” And I think the basis of relationships is, “How can I help? How can I be involved?” and then it wraps up with, “What matters?”

Brian: It’s amazing to me—and I’m sure it’s true in other industries—but when I go to NSAA it’s kind of like a family reunion beyond Jiminy Peak. The common passion for doing this in your life creates a unity and a kind of common bond that says that, while we are not all the same personality, we value the mountains, we value the challenges the weather brings us, we value giving this experience to folks in the world.

Did you have mentors early in your career? Who is it, and what did they do for you?

Brian: I had an uncle who was the ski school director at Glenwood Acres/Kissing Bridge and while I was fascinated with Blue Mountain, he was my idol. He was about 10 years older than me and it was kind of like I was his kid brother. I watched him have a successful life in the ski business doing what he was doing. He’s still close to me today. I have to say, just the excitement of seeing how someone could spend their life doing something they really love made it easy to just keep following this path.

Dennis: I wish I could be succinct in that, but you know, our lives intertwine with so many people. The earliest in terms of what I learned for work would be a friend who was a retired FAA mechanic. He taught me to believe in yourself and that you can accomplish anything if you do.

The next was actually the guy that had my job before me, Skip Yahn. He showed me that you need to enjoy everything you do, whether it is difficult or easy. And there are three more: John Northrop. He’s on our board today. His parents were part of the founding group of Holiday Valley. John has taught me to be honest and, above all, fearless in the face of problems.

And Pete Widger. He started his ski career here and has been the Holiday Valley snow reporter for 10 or 15 years. At age 78, he hikes every day, skis every day, and I go with him most days. He reminds me of the excitement, the love, the spirit, and what skiing is about.

And probably the most important is our last founder, Edna Northrup. She’s 90 years old. She’s managed adversity in her life and shown me—and others—that the key is to keep showing up and to always stay true to who you are.

I probably would have said Brian, but then I’d be admitting that he’s much older, if he’s old enough to be my mentor.

Brian: Ha! You know it.

Recall a pivotal career moment, whether it was something that went right or wrong, a moment that stands out in your life.

Dennis: I think my pivotal career moment would have been in the summer of 1978 when Bobby Foster called me and said, “Would you like to be the ski school director at Holiday Valley?” At that point, I think I knew I was in it for the long haul.

Brian: Mine goes all the way back to 1969. I was very young, out of school and I got to come interview at Jiminy Peak. The board had told Fred Crane, from the Crane Paper Company, that either you’re going to be head of research and development or you’re going to run Jiminy, but you cannot do both anymore. And he said to me, “I think you can do this. You can talk to me on the phone. You can come see me any time you want.” And Fred held true to that. He became kind of a mentor and a father figure, and was somebody I could turn to.

I think you need people around you to turn to for help, or that you know they support you just with a nod of the head. It’s hard to be in this business and be the Lone Ranger.

Dennis: One of my greatest relationships is with the guy on the other end of this conversation. I have used Brian as a resource and I think I’ve served as a resource at times for him, to exchange information and not be afraid to ask for help. I think Brian actually taught me that lesson a long time ago.

Brian: There’s nobody I have a friendship like I do with Dennis. I have that with my son, too, but in terms to being able to talk to somebody and say, “What do you think?” You cannot put a price tag on it.

Dennis: Is this a good time to ask about the will?

What are you most proud of in your career?

Dennis: To fully appreciate the importance and value of what others contribute. … I’ve always been a technocrat and a strong and independent individual. It took me a long time until I evolved and learned that critical part of leadership. My greatest regret is that it took me 20 years to fully understand that, to fully wrap my arms around the importance of that and appreciate the value. It’s made my life easier and more enjoyable because I actually have that true appreciation of the power of a group.

Brian: If I look at my Jiminy team, I truly look at it as family. I hope I enhanced their lives in some way in terms of career growth, financial stability, challenging them, and the process of recognizing that if you didn’t have those relationships and the mutual respect in those relationships, you’d falter all the time.

I think the ability to have the patience to accept that we’re not all perfect—except for Dennis and me—and to be able to work and tolerate the issues that might not be to your liking, but recognize the benefits that somebody brings to the table is important.

Both of you had intangible answers. It wasn’t the chairlift you put in. It was more about people and relationships.

Dennis: In the ’90’s I might have answered differently.

Brian: I agree! If there was one, though, I’d say getting the wind turbine functioning. That was a big and bold step. I’m proud of that one.

Looking across the industry now, who do you see as the future of the industry? Who are the people to watch?

Brian: (My son) Tyler is committed to the industry; he’s in love with it and I think he’s going to be a good guy to hand the business off to. There is a reasonable amount of offspring in the industry that have decided to follow in their parent’s footsteps. Peak Resorts has family doing it. The Vail’s of the world? I’m absolutely confident they have a war chest of up-and-coming people. But I don’t know who they are.

Dennis: There are many of our contemporaries I look at and admire. But I think the real future is more grassroots than that. I have learned to appreciate the young people. It’s easy to criticize, condemn and complain and judge young people by your standards. But I look at people we’ve hired here, and the men and women who are teaching skiing or selling group programs, and I think it will be one of those people who emerges and ultimately makes a difference in this world. I’m excited about it.

What keeps you up at a night and what motivates you to get up in the morning?

Brian: We all end up having some surprises, I’ll call them mechanical challenges or incidents, that happen. There’s nothing you can do about them. And it can be pouring rain on Friday of MLK weekend and then go to zero on Saturday morning. You just don’t know what frying pan might hit you next. You have to be prepared to have those sleepless nights to figure out how you are going to recover from it.

Dennis: Brian is spot on. We’ve dealt here with a myriad of issues. We’ve had a data breech; we had an ADA website compliance challenge. The list goes on and on.

I had a great lesson three years ago from a bike crash. I broke 15 bones, 20-plus fractures. I learned to appreciate help and care. But I also learned about being thankful that you can wake up every morning and have that opportunity to face those problems. To learn to adjust to the new normal and accept it.

Is there anyone you want to apologize to?

Brian: I have some people whose departure I did not handle as well as I could have. I did not do it face to face. I did it over the phone, or stupidly, through a written communication.

One that stands out is an architect who had been very loyal in creating the theme of Jiminy. Things kind of fell apart, and he went on a surprise vacation for a month when we were in the thick of things. I went and got someone to replace him before he came back. Rather than go to him and explain, “Look, I was in a jam and I didn’t have a choice,” I did it by letter.

And I look at the times when I did not confront someone face to face and be honest with them. If I had it to do over again … some of those people are deceased now, and I’ve gone to their funerals and said, “Coulda, woulda, shoulda.”

Dennis: I can think of times when I could have done the same thing. It’s funny hearing Brian say that, because if there was a person I admire in their ability to deal in those situations and not be afraid to speak their feelings, it’s Brian.

Brian: Thank you for that compliment, but I can tell you, I’m much better at it today than I was 30 years ago. Maybe it’s because I learned my lesson.

Share a funny moment—the story you like to tell that just makes you howl.

Brian: OK. I was flying up from Florida, and the weather got bad and I had to land in Washington, D.C. Dennis had just signed a contract for his food services with my partner, Joe O’Donnell. I had a Blackberry at the time, and the battery was dying. Dennis called me and said, “I’ve got a problem. We’re going to break the contract with O’Donnell and I really don’t know how to do it. Is there any way you might break the ice with us?”

I said, “You cannot do that!” He said that another vendor came back with a better offer … could you make the phone call? I truly had sweaty palms.

So I called Joe’s office and I said, “I’ve got something to share with you and you’re going to get really pissed. Holiday Valley is breaking their contract.” He said he had to take a phone call and he’d be back.

Just then my battery died. I got another one and called Joe back. He said, “That son of a bitch Dennis—I’ll get him. He’ll never sell a hot dog. I’ll go after him until hell freezes over. He’ll be sorry he ever did something like this to me!”

Now, I’ve known Joe forever, and I’d never heard him speak like this. So I called Dennis back and told him the whole story. He let me expound for five minutes, and then he said, “Um, you happen to be on a speaker phone and—we gotcha!” The two of them were sitting there together—it was all a big joke.

What will you do in retirement?

Dennis: Who’s retiring? Has my wife been talking to you?

Brian: I don’t know if Dennis and I are guys who are ever going to be playing golf every day. I think being challenged and being part of a unit, whether we are staying on as board members or consulting, it’s going to be hard to say I’m not going to be doing something that’s making a contribution. You know, I’m 70 years old, and I’m at a lake house in Winnipesauke. And I’m on phone calls and go to meetings all the time. I recognize that if I did not have things to challenge my mind and my soul, I’d be putting one foot somewhere.

Dennis: I’m much younger than Brian, and I don’t own a house on Winnipesauke … but I’m very sensitive to this: You have to get the old out of the way for the new. The last thing I want to become is an obstructionist. I am aware there is a time to move on.

But I don’t want to stop working. I love what I do. I love my life. I feel fortunate and blessed.

My bike accident taught me something important. You get a close brush with life and people ask what you would do differently. My answer: Nothing. I think I can continue the journey as long as I am bright enough to get out of the way of the young people. I hope I am.