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It should be no surprise that their long-time friendship and professional dealings has been peppered with jokes, big moves, and more than a few got-your-back moments. After all, Mammoth chairman Rusty Gregory and former California Ski Industries Association executive director Bob Roberts bonded over a $6,000 bar tab that, to this day, neither of their then-bosses may have realized was pushed through.

It was in London, where the two were at the Daily Mail Ski Show (then a massive event), and they had none other than Sir Richard Branson on the hook, ready to partner to send gobs of British ski enthusiasts to California.

“I was buying stuff from Napoleon’s day, literally. I knew I had spent too much when they awarded me a certificate and took my picture at the end of the night. I spent $6,000. Not a chance the McCoys would reimburse me for alcohol, much less at that price. Bob understood the import of it all. We knew we were kindred spirits,” says Gregory.

Today, with Roberts “repotted” (he prefers that over “retired”) and Gregory leaning toward that time, the two still share regular phone calls and meet-ups to talk business, and still pepper each talk with laughs. We asked them to sit down and think back—and ahead—on the industry they love.

MM: To start, I want to know the moment you knew this industry was right for you. That moment when you thought, “This is where I belong and this is where I need to be.”

BOB ROBERTS: Oh boy, you’re asking about ancient history here. It was back in 1969 when I had moved to Mount Shasta and I owned a restaurant there. A gentleman walked in who happened to be the manager of Mount Shasta Ski Bowl, and he said, “Bob, would you like to come up and run the area for the last couple of months?” I felt like Sophia Loren had just walked into my restaurant. I mean, it was absolutely mind-boggling. And it all started there.

RUSTY GREGORY: It may sound trite, but I moved to Mammoth on the way to law school, and put my acceptance offer off just for a year, so I could learn how to ski. I’d skied a few times in college, and I just wanted to live that life for a year. After, gosh, about three or four weeks, I realized I was just an out-of-towner, and I was never going to be a local unless I got a job here. So I got a job as a lift operator. The first day I had a blast. Everyone was happy and I was part of that, and I realized that the probability of returning to law school would be diminishing on a daily basis. In fact, I never went back.

MM: I think it takes a special kind of person to not just survive but thrive in this industry. Do you agree? And what are the most important traits one needs?

RUSTY: At least here in Mammoth, you have to love uncertainty. You have to be able to wake up in the morning and appreciate nine feet of new snow, all of which you have to shovel off your driveway. And yet somehow you have to appreciate, and I really mean it, you have to appreciate that Mother Nature owns the place and you just rent it. If deep down you don’t really like the changes she throws your way, this is not the right business to be in.

BOB It’s always a bit of a crapshoot as to what Mother Nature is going to do to you. But you’ve got to be tenacious. It requires patience and tenacity to run a mountain. You’ve got to have a pretty strong sense of humor, too, just to sort of roll with a lot of the various punches Mother Nature and the general public will throw at you.

MM: Through the years, did either of your have a mentor? Who was it and what did they do for you?

BOB: I had a pantheon of mentors. If I have to distill it down to the ski industry, it has to be three. Luigi Foeger, who came up in the ’70s because we were trying to expand. He came on a day when it was blowing 60 mile an hour and we had all our equipment out because we didn’t have a place to store things. He looked around and he said, “Bob, you’re not in the ski business. You’re in the equipment repair business.” Out of that we became very good friends, and for the next 20 years he taught me a whole lot about reading a mountain and running a ski area.

Another was Nick Bedami, who came along in about ’76. Nick introduced me to high stakes poker with both the Forest Service and the various folks in Washington. He was a wheeler and dealer. I learned a great deal about business in the real world and politics from Nick. [Ed. note: Badami went on to own and run Park City, making it the home to World Cup racing and the U.S. Ski Team.]

And obviously—and probably the same for Rusty—Dave McCoy [Mammoth founder] was just a genius for me. If we had an operations problem, he had the patience of Job to just listen and make suggestions. It was fabulous.

RUSTY: I had countless mentors. In the beginning it was those people of all ages who had been in Mammoth for a year or for 30 years, that knew how to live the life and enjoy the mountains every day, which did not just mean great powder skiing. It meant enjoying the whole experience.

My most obvious and memorable, though, was Dave McCoy, whom I met while I was working on Chair 16 at Mammoth as a lift operator. You know, it’s questionable what kind of chairman and CEO I am, but I was a good lift operator. I was a fairly entertaining fellow at the bottom of chairs, and I met this attractive middle-aged couple that skied up onto my lift. I said something completely inappropriate to this guy’s wife, but I was friendly—very friendly! I was told by the people behind them that the couple was Dave McCoy and his wife, Roma. It took me 38 years to recover from that, I think.

Dave was my mentor because he really knew how to do that. He would walk around and say to people, “God, isn’t it a great day?” It could be blowing 180 miles an hour and raining at the same time. And I realized after some years that he wasn’t kidding: he really thought it was great. He thought that kind of big Mother Nature experience was what skiing was all about. He infused that in the company and in me, and I had a low enough IQ to believe it, and still do.

MM: We talked about when you realized the industry was right for you. Can you think of a pivotal career moment? A time when things shifted for you in a way that surprised, delighted, or scared you?

RUSTY: For me it was the first time I had a major disagreement with Dave McCoy. And it was pivotal because I survived it, and also learned a lot about Dave and about leadership. Bob, you will remember this. We had built two lifts at Mammoth with Jan Kunczynski that were very innovative lifts. One was called the QMC, a quad monocable tram that was built over at June Mountain shortly after we bought June in the 1980s. Another was the People Mover, we called it, which was sort of Mammoth’s version of the Chicago L Train, except it was a little less reliable. It ran from the main lodge all the way down to Chair 2, with four stops.

For a variety of reasons, the lifts were difficult to run safely on an ongoing basis, and at one point they had not run for some years. The Forest Service was putting pressure on me to take them down if we were not going to run them. The Forest Service didn’t have the guts to tell Dave McCoy that to his face, and Gary McCoy and I didn’t, either. So I sat down with Dave and he went over with me … the virtues of those two lifts and that we could just live with them. 

He left on a trip to some place, maybe Europe with Doppelmayr. So while he was gone, we began the process of taking out the lifts. When he left, he basically said to me, “I completely disagree with your view that we should take the lifts out.” But between the lines he gave me the confidence that I should do what I felt was right. So, the People Mover was gone when he got back, and he was very upset.

It never affected my employment, but it was a pivotal moment. I realized that what Dave needed at that time was someone who was less impressed with his legendary persona and more focused on giving him an honest assessment of the world. It was a change in our relationship. I still get a little sweaty when I think about it. Dave was and is a very powerful guy in many ways.

BOB: One pivotal moment for me happened on Oct. 29, 1971. We were just about ready to open for the season, and I got a call from a young kid I had living up in the lodge. He said, “Bob. The lodge is on fire.” It burned to the ground.

I was just incredulous. I thought, “We are ready to go here, and I have no lodge.” The really amazing thing was the way the whole town turned out. We had everyone under the sun help us rebuild. This was before all the environmental rules that absolutely would have stymied us for two years. We could do that kind of thing in that era. … almost everybody in town pitched in in some way, and in 68 days, we opened. Understanding that hey, there’s an incredible importance and resilience in your community, that was a pivotal moment.

Another was, and Rusty you were there, when we had dinner with Richard Branson. We had gotten a grant to rebuild our international markets after a drought. Now, we never really had international markets, but … we got the grant anyway, about $440,000.

We knew the biggest market was in the U.K. So we went over to London for the Daily Mail Ski Show. But we couldn’t get an appointment with anybody. We had an event down in Pickadilly and all these swells with their bespoke suits wouldn’t talk to us, but they drank our liquor and ate our food.

So I walk up to this guy in a sweater, and he says, “Hi, I’m Richard Branson, and I love to ski at Mammoth!” We ended up having dinner—and listen, having dinner with Richard Branson is like having dinner with Thomas Jefferson. He can talk knowledgably about so many subjects. Finally, somewhere about the main course, he says, “Look, Bob, I’ll put up 25,000 quid and you put up 25,000 quid and let’s see how we do.”

Well, I didn’t even know what a quid was, but you know, if you are in that kind of a poker game, it had to be less than the $440,000 we had at stake. So, that started it. And by the time we got the dessert, I said, “Hey, we’d love to have you as a speaker back home.” He said, “Brilliant! Spot on! I’ll do that. But we’re in a big trial with British Air, so if I’m in the dock I won’t come.” He came, and out of that, by the time we were in high gear, we were doing about 9,000 guests a winter from Britain.

MM: You two have so much experience. If you could tel your younger self something, what would it be?

RUSTY: There are a lot of things someone should have told my younger self. But you know, it’s something Dave McCoy did tell me: in the end, it’s about the people. As pretty as we think Mammoth is, everybody in the business has green trees, white snow, and blue skies. What matters is how you treat your people. How you treat your guests, your employees, and your investors in the company. And at the end of the day, everybody in town has an investment in this, and it’s about your relationship with all of them. I know that now, and I learned it sometimes the hard way. But that’s the thing I would like stamped on my forehead if I was going to start over again.

BOB: I would probably say that patience is power, and by and large, tenacity will serve you better than intelligence.

MM: In that vein, is there anyone either of your want to apologize to?

RUSTY: There were a lot of people who were affected by my young and brash style of management when I first moved into a position of some authority on the mountain. I was a finance guy, but my job was human resource director, which is a little like letting someone with a match into the gasoline factory. I came in and thought my job was to cut budgets, and you know, a lot of people felt the impact of the misplaced priorities of my earlier days. I hope I’ve made up for that.

BOB: We had a sophisticated marketing system back at Shasta. Basically, I’d get up in the morning and call the guys on the mountain to get the report on how good or bad it could be. Then I would get on my phone with a cup of coffee and make calls to all the radio stations around the area. The weather often changed by the time I was done babbling on the air, and there were an awful lot of skiers who would drive about an hour-and-a-half based on my reports and who were really unhappy. I apologize to those guys.

MM: You were only doing the best you could do, though.

BOB: My wife found it amusing.

MM: Now, looking forward, who do you see as the person to watch in the industry?

BOB: I’ve got three. Kevin Mitchell of Homewood—as an operator he is really impressive. Amy Ohran at Boreal—she’s very talented and has a tremendous business sense. She’s no-nonsense and knows how to run a business. And of course the third is a guy Rusty knows very well, [Mammoth chief administrative officer] Ron Cohen. I think Ron is one of the brightest guys in our industry, period.

RUSTY: Ron is a very smart guy who is passionate about the business.

There are a lot of up and comers, and—this will seem like an odd comment—but the guy I’m most interested to see what he will do next is Rob Katz. He’s not that young anymore, but he’s certainly still a comer. Some people think of Vail as the Evil Empire, but if you look at what Rob has done to revolutionize the industry (because a lot of us are following in bits and pieces what he is doing), I think it will be very interesting to see what he does next. What he does might be the most important thing that happens in the industry in years to come.

BOB: I would echo that.

MM: Can you share something interesting about one another?

RUSTY: I just want to go on the record that Bob has the bushiest eyebrows I have ever seen.

BOB: I inherited them from Dukakis.