All Images: Courtesy of The Ski Monster
Ski shop owners typically worry about thin snow years and late inventory. George Michaelsen, owner of The Ski Monster (TSM), never thought he’d have to worry about Elon Musk. But when a real estate trust’s Twitter-occupied building stopped generating rent, the fallout set off a chain reaction that pushed his shop off Boston’s Canal Street. A new location was built out on Boston Common, only to find a serious safety issue overhead, which would force another move within the city. All while opening a second, Minnesota location in the middle of the chaos.
A Real Estate Nightmare
In 2023, the building housing TSM went into technical default and was repossessed by the bank. As it was explained to George, another building owned by the same real estate trust was tied to the same loan. That building was occupied by Twitter (now X), which had stopped paying rent. When The Ski Monster's building was purchased again in 2024, the new owner neglected to maintain it, forcing TSM to find a new home.
Michaelsen and his business partners, Brady Page, Dylan Lavoie and Neil Soucy, found another location on Tremont Street and began building out the shop in the spring. Inventory was moved in, tuning equipment was in place and everything was on track for the upcoming season. Then George got a call from Lavoie at the end of August.
Turns out, the parking garage directly above their new shop had serious structural issues, including the possibility of large chunks of concrete falling through the ceiling. Not exactly ideal for a ski shop, especially with winter approaching.
Table for Two
With the clock ticking, Michaelsen and his team had to relocate The Ski Monster once again, this time to 10 High Street in Boston’s financial district. While they intend to move back to 151 Tremont Street next winter, the shop’s temporary home is an old Italian restaurant converted into a specialty ski shop, where customers now get fitted for boots while sitting in old-school dining booths. BYO-cannoli, though.
Most business owners would have taken a break after such a chaotic move, but not Michaelsen. He and his partners had previously decided to expand the business and they weren’t going to let this hold them back. Looking at his hometown of Plymouth, Minnesota, and the greater Twin Cities area, he saw a well-established but highly underserved ski community and decided to do something about it. The Plymouth shop opened in September, offering a wide selection of gear for skiers (and snowboarders) of all levels and upholding the personalized service the Boston shop has become known for.
Both locations offer access to local skiing and major airports, allowing skiers to chase snow out west regardless of their local winter conditions.
“When you want to have a good time, you might not want to spend your ski vacation chasing down gear,” Michaelsen says. “You’d rather get that done at home, and then when it’s time to go rip it up on your ski vacation, just ski and do all the things that go along with it: drinks, a good lunch outside, après, that whole thing.”
He views the Minneapolis-St. Paul area as an underserved market full of skiers who appreciate high-quality gear and knowledgeable service. That attention to detail is central to TSM’s approach, summed up by the motto: “We lose sleep over making sure we get it right.”
It’s (Almost) All About The Boots
Nowhere is that approach more apparent than in the bootfitting process. The TSM crew has catered to tens of thousands of feet over the years. Both locations specialize custom bootfitting, footbeds, liners and post-purchase boot work to ensure you find the right fit for your feet and skiing style. Even if you didn’t buy your boots from them, they’re happy to put in the work that will make your ski days better. Michaelsen views boots as an “extension of your foot,” and a team member works with each customer throughout the process. That philosophy seems to work; the Boston location alone sells roughly 4,000 pairs of boots a season.
TSM operates on a hybrid model, welcoming walk-ins but recommending appointments to minimize wait times. While the process takes time up front, the goal is to eliminate unnecessary return visits and boot issues down the road. Ideally, that means more time on snow and less time wondering why your feet hurt or whether you bought the wrong boots.
Stay Awhile
Michaelsen draws inspiration from the ski, snowboard and skate shops he visited as a kid, thinking about what would have made him stoked to walk through the door. While Boston’s temporary shop occupies a former Italian restaurant, Plymouth is closer to Michaelsen's original vision: a cool, living-room vibe with comfortable chairs, a beer fridge, DJ booth and a boot lab surrounded by floor-to-ceiling windows. It's the kind of place where you can hang out long after your bootfitting is over, talking about gear, snow conditions and your favorite ski movie segment of the season.
And that's what ski culture is all about. If you want to see it for yourself, The Ski Monster offers ski bootfitting in Boston and ski bootfitting in the Twin Cities , with appointments available online at both locations.
