Chicago Booth alumni on the annual group ski trip

Living the High Life

A casual ski trip among friends has grown into a decades-long tradition for one Booth class, full of bonding on and off the slopes. 

  • By Michael Blanding
  • February 24, 2022
  • Community

Some business school students walk out the door at graduation and see their old classmates only sporadically. But for the class of 1992, getting together is an adrenaline-producing event—an epic, weekend-long ski trip that takes place every winter. 

The tradition began in the mid-1990s when a small group of friends including Dan Hoskins, ’92; John McBain, ’92; Ed Ryder, ’92; and Jim Tuchler, ’92, took a trip out to Beaver Creek Resort in Colorado.

“It was probably a core group of 10 of us for a number of years, and then it started to grow as more people started hearing about it,” says Ryder, managing principal and real- estate investor at BayRock Partners in Chicago, who serves as the official coordinator of the yearly outing. 

Now in its 26th year, the Booth Class of 1992 Ski Trip typically draws between 20 and 35 classmates. Most years, the group travels to Lion Square Lodge, a ski-in, ski-out condo resort in Vail, Colorado, to hit the slopes, share dinners, and reminisce in the hot tub. 

“I think there is a very human desire to keep up with people you’ve known for a long time, and who remember you when you were younger,” Ryder says. “And when we get together, it’s like nothing has ever changed.” 

Ryder admits he’s not the most accomplished skier himself. Originally from Long Island, New York, he worked as a financial analyst in Florida before coming to Booth. His first time on the slopes, he was so inexperienced that it took seemingly forever for him to get down. “I was literally the last person to come off the mountain,” he laughs. “I had the ski patrol guys right behind me.” But he fell in love with the sport, especially with pristine glade skiing. “I love going out into the trees, especially when there is fresh powder, and just cruising along,” says Ryder. “It is so peaceful and beautiful.”

Ryder treats the Booth trip like a real-life B-school case, creating a complicated spreadsheet with all of the costs for beds, meals, and lift tickets, which are then split equitably between participants. In the beginning, accommodations were spartan, with classmates sharing beds and sleeping on pullout sofas. When John Greener, ’92, now chief human resources officer of online pet retailer Chewy in Dania Beach, Florida, was forced to sleep on a pullout one year and was kept up until the wee hours by rowdy classmates, the group instituted the Greener Rule, declaring each participant must get a real bed. “We’ve reached the point of maturity where sofa beds are off limits,” says Ryder, noting most participants are in their 50s. “That’s a bright line now. We always get a big expensive room right by the gondola that we call Base Camp. The refrigerator is stocked with food and beer and wine, and everybody goes there for breakfast in the morning and happy hour before dinner.”

 

Keeping the group together on the trip can be like herding snow cats, especially at such a large resort. Oftentimes, the crew breaks into smaller groups, which might meet for lunch in the middle of the day at the mountaintop Two Elk Lodge. Time off the slopes, Ryder says, is just as important as the time on them. Because it can be hard to make a restaurant reservation for 25 people, the group caters meals, or members volunteer to cook—like the time McBain grilled up dozens of New York strip steaks. Après-ski, the group gathers in Lion Square’s enormous hot tub, which can hold upward of 20 people. “We have so much fun in that hot tub,” Ryder says. “We put on our bathrobes and walk down the hallways with a 12-pack of beer under each arm. We bring music and hang out.” 

The ringleader of the group is Hoskins, cofounder and managing director of private equity firm Glidepath Capital Partners, based in Los Angeles. “He’s a larger-than-life personality with this great booming voice,” says Ryder. Hoskins has contributed to legendary memories over the years, such as the time he came flying without warning to do a cannonball in the middle of the hot tub. Another year, he challenged Tuchler, a world-class swimmer, to a swimming competition (although there were a couple extra rules in their contest). Hoskins won, and the group has never let Tuchler live it down. “We’re like, you’ve got all these world records, and you can’t even beat Hoskins!” Ryder says.

Other participants have made their own unique contributions to the trip. Tuchler, president of GiftsForYouNow.com, based in Burr Ridge, Illinois, brings a different personalized keepsake every year—from baseball caps to coasters to cutting boards. Nanci Fastre, ’92, senior liquity advisor at Santa Clara, California-headquartered Silicon Valley Bank, is also an amateur craft brewer. She ships a new brew for the group to sample every year. Everyone finds time to network, offer career advice, and foster connections. “Especially as everyone’s moved up in their companies over the years, a number of us have invested with each other,” Ryder says. “People are always picking my brain about what’s going on in real estate.”

Over the years, the skiers have developed tight bonds, counseling each other through challenges at both work and home, and laughingly recounting happy memories from their time at Booth. 

“We all have so much history together. There’s a continuity to it that I have come to really appreciate,” Ryder says. “Everyone looks forward to it. I’ll start getting emails in July, asking ‘Have you picked a date yet?’ No one wants to miss it.”

Ed’s Tips

Planning a group ski trip? Here’s how to make it successful:

No cheapskates. “We divide everything up evenly, and no one questions the cost. You may get a king bed one year and a twin bed the next. I think people appreciate throughout the years that they can just come and don’t have to think about money—all they have to worry about is putting aside the dates.”

Designate one purser. “Somebody’s got to pay for the dinner and lay down the money for the rooms, because you can’t collect cash for every little thing. We were supposed to rotate every three to four years, but I just wound up being the guy who does it permanently. I kind of regret that a little bit, but with Venmo and PayPal, it’s gotten a lot easier!”

Make sure you like each other. “You’re only on the slopes from maybe 9 to 2, so you’re not really skiing all the time. The evenings are really key. So starting a ski trip like this with a core group that really likes each other is really important. Had we not had that, I don’t think it would have lasted this long.”

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