As a senior at Amherst College,
Win Smith and a few of his fraternity brothers decided to grab some season passes, rent a house, and hit up the ski slopes in Vermont’s Mad River Glen.
The season came to a close and Smith didn’t ski again for almost 14 years.
After graduating from Amherst, Smith went to Wharton for graduate school and later landed a job in New York at Merrill Lynch — a company his father once helped lead.
He started out as an entry-level investment banking associate and ended up working for there for 28 years, rising to the role of executive vice president. In 2014, he wrote a book, “Catching Lightning in a Bottle,” which chronicled the rise and fall of the firm.
He hadn’t given skiing much thought over the years until a serendipitous gathering drew Smith back to the slopes in 1984.
He took his family to Vermont for a reunion with his fraternity brothers and his children became hooked on the sport. Smith bought a house in Warren, Vermont, in 1994, and started spending most winter weekends up there skiing at a resort called Sugarbush.
Then, in early 2001, he got a call from a two businessmen based in the Mad River Valley saying that Sugarbush was teetering on the verge of bankruptcy. They asked Smith if he was interested in buying and resurrecting it.
Smith then approached Joe Riemer — a Merrill Lynch colleague and good friend — to gauge his interest, and together they decided to give it a shot. (
Riemer died of cancer a few months later.)
When the four of them bought the resort in September of 2001, Smith intended for it to be a “passive investment,” so he kept his day job in Manhattan.
A month later, Smith got a new boss at Merrill Lynch.
“He made me an offer to stay as vice chairman but I was really concerned about his direction and I was really distressed that he didn’t seem to appreciate the culture or the history of the firm.”
So Smith left Merrill and went into private equity.
He did that until 2004, when he realised that things at Sugarbush weren’t much better than they had been prior to the sale. He knew if he wanted to see the resort come back to life, he’d have to get more involved.
He was 55 at the time and “was up for the challenge” of making a major career change.
“I don’t believe one should ever ‘retire,'” he says, “I think you just go on to different things.”
Smith’s family was supportive of his decision. However, he says that not everyone understood why he was making such a big career change.
“I think most of my friends thought I was totally nuts,” Smith tells Business Insider.
But he packed up and moved to Warren anyway.
The town of about 1,700 permanent residents doesn’t have traffic lights, billboards, or national chain stores. It looked nothing like his old life, but Smith quickly found that running a ski resort in Vermont really wasn’t all that different from working on Wall Street.
“There’s a lot that’s not under your control, like the weather” he says. “So you have to focus on the things that really can be under your control. You focus on things like customer service and how you build the culture of the firm, how you build the team, and how you motivate people. Another other similarity is how you organise and finance the business. Merrill Lynch failed because it became overleveraged. It had too much debt. A lot of ski businesses fail for the same reason.”
But it wasn’t the easiest transition.
“For the first few days, I really wondered what the hell I’d done,” he says. “I was leaving a lot of money. I was leaving a big company. I was, in many ways, leaving a lot of people I cared for. That was a challenge at first.”
Luckily, the pivot was made easier by the fact that running a ski resort has its perks.
Smith, now 67, spends a good amount of time hitting the slopes in the early morning, before anyone else is out.
“I’ve always loved the outdoors and I live in a beautiful part of the world which is just, environmentally, very clean and rich,” he says.
His ventures up and down the mountain also serve a practical purpose: he can check in with his employees and interact with his guests. The resort employs about 1,000 people in the winter season and draws just under 400,000 winter visitors.
He says running the resort isn’t all snow and games. It has its challenges, too.
Last year, the resort endured what Smith calls “one of the worst winters in the last 50 years.”
“I think part of the excitement of the business is that when you get through the challenging years, it’s also very rewarding,” he says.
When reflecting back on his career, Smith says that running Sugarbush has allowed him to pursue his real passion full-time.
“If you can’t get excited when you wake up in the morning, if you’re not doing something you really love, then don’t do it,” he says.
Smith believes that many people could stand to take a chance and pursue their dreams, once in a while.
“I think at the end of the day too many people rationalize why they should stay, rather than launching out,” he says. “When they launch out, they often find that they’re going to land on their feet.”
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