And why urban messiness is an important feature of cities
I'm back in Toronto. And another "fresh pow annual" is in the books.
The BC interior is a specific kind of ski and snowboard trip. It's not about dancing on tables in neon onesies while Champagne gondolas fly overhead. It's about chasing champagne powder with like-minded middle-aged men, all pretending that they don't otherwise live a sedentary, low-range-of-motion lifestyle for the balance of the year.
And why urban messiness is an important feature of cities
I'm back in Toronto. And another "fresh pow annual" is in the books.
The BC interior is a specific kind of ski and snowboard trip. It's not about dancing on tables in neon onesies while Champagne gondolas fly overhead. It's about chasing champagne powder with like-minded middle-aged men, all pretending that they don't otherwise live a sedentary, low-range-of-motion lifestyle for the balance of the year.
We stayed in four different accommodations for this trip, and one of the things that became very apparent is that everyone is trying to over-optimize around "good service." In each case, I was getting text messages and emails before the stay, during the stay, and after the stay.
"Here's how to prepare before check-in." "Is there anything we can do to make your stay more enjoyable?" "How was your stay?" "Please share your experience with us here." In one case, I even received a phone call from the front desk as soon as I got to my room: "We just wanted to see if everything in your room is to your liking."
On the one hand, this level of communication and responsiveness is fantastic when you do need something. But on the other hand, it can be overwhelming. Blasting everyone with automated text messages and emails does not, in my opinion, stand out as exceptional hospitality, especially since everyone now seems to be doing it.
Outstanding hospitality is emotional, rather than technical.
In city-building news, Bloomberg recently published an article about why cities should embrace "messiness." In it, they cite a book that was assembled by some fellow Torontonians:
This premise — that urban planning’s efforts to impose order risk editing out the culture, character, complexity and creative friction that makes cities cities — is a guiding theme in Messy Cities: Why We Can’t Plan Everything, a collection of essays, including Thorne’s, gathered by Toronto-based editors Zahra Ebrahim, Leslie Woo, Dylan Reid and John Lorinc. In it, they argue that “messiness is an essential element of the city.” Case studies from around the world show how imperfection can be embraced, created and preserved, from the informal street eateries of East Los Angeles to the sports facilities carved out of derelict spaces in Mumbai.
Messiness and allowing for ground-up urban interventions are themes that I have written a lot about on this blog over the years. I think we have gone overboard with rules and regulations, to the point that we stamp out many of the things that make cities so wonderful.
Top-down planning will never get everything right. It's impossible. And the big thing about over-planning is that, in the end, we don't actually know what we're missing out on. We don't know what might have been possible if only we had allowed for it or were more flexible in our approaches.
Messiness is a feature of cities, not a bug. We should be embracing it.
Whistler is out, the Interior of BC is in. Huge real estate deals are out, powder chasing is in. If you're a long-time reader of this blog, you'll know that I do a ski and snowboard trip with a group of friends each year around this time.
Our last three trips were to Park City (where it snowed so much we lost power); Trois Vallées (which also served as my bachelor party and which involved equal parts snowboarding and dancing on tables); and Hokkaido (where it looked like Toronto looks right now).
This year — for annual number fifteen — we're headed to Revelstoke and Kicking Horse in the Selkirk and Purcell Mountains.
On some trips we like to combine an urban trip with the mountains, so that we can also gawk at architecture and urbanism. That's what we did in Japan last year. But this year's trip is not about that. It's about unadulterated time in the mountains.
It has been a weird season for snow. The west coast has been too warm with not enough of it, and the east coast has been too cold with unusual amounts of it. I have no idea what's in store for us this week, but here's to hoping it looks like the cover photo of this post.
In some related real estate news, Extell Development Company and Hilton just announced that they'll be opening a Waldorf Astoria Resort and Residences in the new Deer Valley East Village.
It's going to have 132 hotel keys and 105 one- to six-bedroom branded residences ranging from 1,099 to 5,155 square feet. Of the 105 branded residences, 56 will be "hotel residences" located above the hotel, and the remaining 49 residences will be in a more exclusive standalone residential building.
Architecture for the project is by KPF and the interiors are by AvroKO.
If you missed my recent post about the East Village and the new Four Seasons that is also currently under construction, click here.
New York-based Extell Development is currently under construction on a Four Seasons Resort and Private Residences in the new Deer Valley East Village in Utah. When I was there in December, Bianca and I went by to check out the overall progress in the village, and the crew was in the midst of laying the decking for the ground floor. ODA designed the architecture, interiors, and landscaping.
The residential offering consists of Private Residences and Hotel Residences. The former are located in an owner-exclusive building and the latter are in the hotel building, where the units can be put into the Four Seasons Rental Program. I'm not sure if this is indicative of their overall inventory, but the remaining Hotel Residences are meaningfully larger than the Private Residences.
As a Park City booster, I think this additional village is exciting. There are now two large interconnected resorts and four distinct villages lining the Wasatch Back: Park City Mountain Resort, Park City Canyons Village, Deer Valley, and the Deer Valley East Village. Visit Utah would say that there's also a third resort in Woodward Park City (which happens to be adjacent to Parkview Mountain House).
But as a real estate developer and snowboarder, I do wonder about two things.
First, Deer Valley East Village is located in an area on the Wasatch Back that receives noticeably less snow compared to other areas because of its lower elevation and broad east exposure. If I refer back to Jim Steenburgh's book, Secrets of the Greatest Snow on Earth, the average annual snowfall at the base of the Jordanelle Gondola (located just north of the East Village) is probably less than 150 inches. This compares to 350+ inches at higher elevations in Park City and 500+ inches in the Cottonwood Canyons.
Because of this, the East Village has obviously invested heavily in snowmaking equipment. But artificial snow is not the same as natural snow. The higher elevations will be just fine, but the lower elevations will likely see marginal conditions. So why build a new village here? And was and is this a consideration for buyers at this new Four Seasons? Or are the luxury amenities and après events the real deciding factors? I'm not their target demographic, but from my perspective, this is reason enough not to buy here.
On the topic of the target buyer, my second question is about Deer Valley's "no snowboarding" rule (which is another reason why I'm not their target demographic). There are only 3 resorts in the United States that ban snowboarding. One of them is Deer Valley, and the other two are Alta (Utah) and Mad River Glen (Vermont). This seems to be a wildly popular rule among resort guests, and I support Deer Valley's decision to weed out "riff-raff" like me. Deer Valley is also known for capping daily lift tickets to keep the crowds down, so they don't seem to be hurting for patrons.
But according to recent data from Snowsports Industries America (SIA), the rough participation split in the US between skiers and snowboarders is somewhere around 60-70% and 30-40%, respectively. There are also many instances where families have a mix of skiers and snowboarders. If you're the Four Seasons at Deer Valley, this segment of the market is excluded. Oh well. The rich snowboarders have Park City, The Colony at Canyons Village, Powder Mountain, Aspen, and many other locations.
My assumption is that the ban on snowboarders is an unapologetic feature of Deer Valley and developments like the Four Seasons. It creates an air of exclusivity and differentiation. Some data also suggests that snowboarders tend to be a more ethnically diverse group compared to skiers (SIA reports show that among female snowboarders, 25% are Hispanic, and among males, 13% are Black — the highest diversity rates in winter sports), so one could argue that it's not just about the type of device used to get down the mountain. And, it seems to be working.
In July 2025, the Extell announced that they had closed a $600 million construction loan for the project from JVP Management and that 60% of the hotel residences were already sold. This is believed to be the largest construction loan on record for a hotel and residential condominium project in Utah.
At the same time, I'm also certain that the Four Seasons lost sales to certain buyers, perhaps a wealthy Boomer or Gen Xer with kids or grandkids who snowboard. Extrapolating this demographic trend, it is also believed that Millennials represent the first generation in the US with near-parity between skiers and snowboarders. So what will this mean for luxury real estate as these Millennials become the dominant buyer segment? My prediction is that the real estate market will respond.
Would you buy at the Deer Valley Four Seasons? Or have you already?
We stayed in four different accommodations for this trip, and one of the things that became very apparent is that everyone is trying to over-optimize around "good service." In each case, I was getting text messages and emails before the stay, during the stay, and after the stay.
"Here's how to prepare before check-in." "Is there anything we can do to make your stay more enjoyable?" "How was your stay?" "Please share your experience with us here." In one case, I even received a phone call from the front desk as soon as I got to my room: "We just wanted to see if everything in your room is to your liking."
On the one hand, this level of communication and responsiveness is fantastic when you do need something. But on the other hand, it can be overwhelming. Blasting everyone with automated text messages and emails does not, in my opinion, stand out as exceptional hospitality, especially since everyone now seems to be doing it.
Outstanding hospitality is emotional, rather than technical.
In city-building news, Bloomberg recently published an article about why cities should embrace "messiness." In it, they cite a book that was assembled by some fellow Torontonians:
This premise — that urban planning’s efforts to impose order risk editing out the culture, character, complexity and creative friction that makes cities cities — is a guiding theme in Messy Cities: Why We Can’t Plan Everything, a collection of essays, including Thorne’s, gathered by Toronto-based editors Zahra Ebrahim, Leslie Woo, Dylan Reid and John Lorinc. In it, they argue that “messiness is an essential element of the city.” Case studies from around the world show how imperfection can be embraced, created and preserved, from the informal street eateries of East Los Angeles to the sports facilities carved out of derelict spaces in Mumbai.
Messiness and allowing for ground-up urban interventions are themes that I have written a lot about on this blog over the years. I think we have gone overboard with rules and regulations, to the point that we stamp out many of the things that make cities so wonderful.
Top-down planning will never get everything right. It's impossible. And the big thing about over-planning is that, in the end, we don't actually know what we're missing out on. We don't know what might have been possible if only we had allowed for it or were more flexible in our approaches.
Messiness is a feature of cities, not a bug. We should be embracing it.
Whistler is out, the Interior of BC is in. Huge real estate deals are out, powder chasing is in. If you're a long-time reader of this blog, you'll know that I do a ski and snowboard trip with a group of friends each year around this time.
Our last three trips were to Park City (where it snowed so much we lost power); Trois Vallées (which also served as my bachelor party and which involved equal parts snowboarding and dancing on tables); and Hokkaido (where it looked like Toronto looks right now).
This year — for annual number fifteen — we're headed to Revelstoke and Kicking Horse in the Selkirk and Purcell Mountains.
On some trips we like to combine an urban trip with the mountains, so that we can also gawk at architecture and urbanism. That's what we did in Japan last year. But this year's trip is not about that. It's about unadulterated time in the mountains.
It has been a weird season for snow. The west coast has been too warm with not enough of it, and the east coast has been too cold with unusual amounts of it. I have no idea what's in store for us this week, but here's to hoping it looks like the cover photo of this post.
In some related real estate news, Extell Development Company and Hilton just announced that they'll be opening a Waldorf Astoria Resort and Residences in the new Deer Valley East Village.
It's going to have 132 hotel keys and 105 one- to six-bedroom branded residences ranging from 1,099 to 5,155 square feet. Of the 105 branded residences, 56 will be "hotel residences" located above the hotel, and the remaining 49 residences will be in a more exclusive standalone residential building.
Architecture for the project is by KPF and the interiors are by AvroKO.
If you missed my recent post about the East Village and the new Four Seasons that is also currently under construction, click here.
New York-based Extell Development is currently under construction on a Four Seasons Resort and Private Residences in the new Deer Valley East Village in Utah. When I was there in December, Bianca and I went by to check out the overall progress in the village, and the crew was in the midst of laying the decking for the ground floor. ODA designed the architecture, interiors, and landscaping.
The residential offering consists of Private Residences and Hotel Residences. The former are located in an owner-exclusive building and the latter are in the hotel building, where the units can be put into the Four Seasons Rental Program. I'm not sure if this is indicative of their overall inventory, but the remaining Hotel Residences are meaningfully larger than the Private Residences.
As a Park City booster, I think this additional village is exciting. There are now two large interconnected resorts and four distinct villages lining the Wasatch Back: Park City Mountain Resort, Park City Canyons Village, Deer Valley, and the Deer Valley East Village. Visit Utah would say that there's also a third resort in Woodward Park City (which happens to be adjacent to Parkview Mountain House).
But as a real estate developer and snowboarder, I do wonder about two things.
First, Deer Valley East Village is located in an area on the Wasatch Back that receives noticeably less snow compared to other areas because of its lower elevation and broad east exposure. If I refer back to Jim Steenburgh's book, Secrets of the Greatest Snow on Earth, the average annual snowfall at the base of the Jordanelle Gondola (located just north of the East Village) is probably less than 150 inches. This compares to 350+ inches at higher elevations in Park City and 500+ inches in the Cottonwood Canyons.
Because of this, the East Village has obviously invested heavily in snowmaking equipment. But artificial snow is not the same as natural snow. The higher elevations will be just fine, but the lower elevations will likely see marginal conditions. So why build a new village here? And was and is this a consideration for buyers at this new Four Seasons? Or are the luxury amenities and après events the real deciding factors? I'm not their target demographic, but from my perspective, this is reason enough not to buy here.
On the topic of the target buyer, my second question is about Deer Valley's "no snowboarding" rule (which is another reason why I'm not their target demographic). There are only 3 resorts in the United States that ban snowboarding. One of them is Deer Valley, and the other two are Alta (Utah) and Mad River Glen (Vermont). This seems to be a wildly popular rule among resort guests, and I support Deer Valley's decision to weed out "riff-raff" like me. Deer Valley is also known for capping daily lift tickets to keep the crowds down, so they don't seem to be hurting for patrons.
But according to recent data from Snowsports Industries America (SIA), the rough participation split in the US between skiers and snowboarders is somewhere around 60-70% and 30-40%, respectively. There are also many instances where families have a mix of skiers and snowboarders. If you're the Four Seasons at Deer Valley, this segment of the market is excluded. Oh well. The rich snowboarders have Park City, The Colony at Canyons Village, Powder Mountain, Aspen, and many other locations.
My assumption is that the ban on snowboarders is an unapologetic feature of Deer Valley and developments like the Four Seasons. It creates an air of exclusivity and differentiation. Some data also suggests that snowboarders tend to be a more ethnically diverse group compared to skiers (SIA reports show that among female snowboarders, 25% are Hispanic, and among males, 13% are Black — the highest diversity rates in winter sports), so one could argue that it's not just about the type of device used to get down the mountain. And, it seems to be working.
In July 2025, the Extell announced that they had closed a $600 million construction loan for the project from JVP Management and that 60% of the hotel residences were already sold. This is believed to be the largest construction loan on record for a hotel and residential condominium project in Utah.
At the same time, I'm also certain that the Four Seasons lost sales to certain buyers, perhaps a wealthy Boomer or Gen Xer with kids or grandkids who snowboard. Extrapolating this demographic trend, it is also believed that Millennials represent the first generation in the US with near-parity between skiers and snowboarders. So what will this mean for luxury real estate as these Millennials become the dominant buyer segment? My prediction is that the real estate market will respond.
Would you buy at the Deer Valley Four Seasons? Or have you already?
