Aspen, January 2026

Ahhh, Aspen.  Just spent 4 days skiing there with a small group of skiers from around the country and literally world champion instructors.  The goal was to improve some fundamentals so I can ski more safely and more efficiently for the next two decades. Mission accomplished.

Wednesdays high school basketball game was between the Aspen Skiers and the Coal Ridge Titans.  Everyone tells you their wealth story and Aspen real estate story in less time than it takes the gondola to travel the bottom of the slopes at the Gorsuch Cafe to the Sun Deck at the peak.  Real estate stories abound, mostly buying early and holding on, with an acceleration over the last 7 years that exceeded all expectations.  In one gondola ride the rider and a lawyer who didn’t know each other were talking real estate transactions (that cost $20k-$30k for legal fees alone) and the gentleman described it as the ‘immoveable vs the indestructible’.  

Aspen is an old silver mining town, it’s heyday in 1880’s or a bit before, with 12,000 persons employed in the mining industry and the related bars, brothels, hotels, eateries and what have you.  Then you had the Sherman Silver Act which set a floor on silver prices, prompted a rush on silver mining since a price floor had been established with the government as the buyer of all things silver, to the repeal of that very same act a few years later when the unintended impacts of the act became clear, and with that repeal a crash of the price of silver when the artificial price and demand were removed, spelling the end of Aspen as a silver mining town.  

Then you had the quiet years, when the population dipped to just over 1000 hardy farmers working a short season, and then the 40’s when the skiing and tourism industry emerged, slowly then all at once.

It’s hard not to hear about ‘Aspen’ but it’s easy to stop your understanding of the place with the superficial ‘billionaire club’.  It’s that, but it’s also hard to get to, limiting the crowds, it’s small with the silver mining days and architecture still defining the cityscape, with buildings no higher than 40’, and many of the original hotels, bars and even miner shacks still standing (now worth $12m for a tiny little spec of Aspen).

It’s the first time I’ve ever been somewhere where I see how comfortable and comforting the insular club of wealth and connections and confidence of position is so cleanly in view.  I've been to plenty of places where this is true - Martha's Vineyard comes to mind - but never with the reach and touch it attainability. You just aren’t doing anything without running into opportunity or network or advancement.  That strata where social and affluence mobility is assumed, tangible.  I could see how an interloper, a fraudster, an Anna Delvey (Sorokin) type character could quickly assimilate with tall tales of nobility, generational trust fund wealth and gilded lifestyles - it’s so quickly a topic of conversation among the Aspen crowd, a crowd that crows with accomplishment and privilege and its parallel track of hitching your wagon to other’s success, that if you play the part well, spend freely (even if it's debt), have a lot of energy, and remember your lines, I can see how fraudsters quickly assimilate.

On the other hand, I’m reading a book written in 1999 by my friend Nina Burleigh, A Very Private Woman, which details upper class American life in the 30’s-60’s, through the eyes of one of JFK’s lovers, and interesting, this woman is a Pinchot, a local Milford family of lore and owners of the Grey Towers where I volunteered for a winter organizing and catoluging old books.

So the day in day out hob-nobbing, cheek-rubbing, back-patting, leisurely life of lunches, colleges, horse riding, travelling within your little club of privilege provides a very firm footing for where you belong, where you are going, and a sure-footed way of getting there.  It’s just all laid out for you, and there is an entire social construct that provides soft guardrails and red carpets, introductions and soft-landings.

The Colorado ski resorts are getting almost no snow this year, and leading up to my trip it was worrisome, but then two storms in the weeks prior that dumped a foot each provided a decent base when combined with cool temps and snow-making efforts. 4 straight ‘bluebird days’, with crisp bright skies and sun.  The typical 4-5’ base of snow is more like 9” - it’s extreme, worked out well for us, but not many other weeks of ski plans, and will be a problem for the plains and farms and ranches and reservoirs that depend on the melt for their annual reup of moisture and irrigation - a snow pack is like a reservoir, since the soil can only hold so much water before it is saturated, so the snow pack lies above, slowing leeching into the ground during the spring, allowing maximum absorption.

I stayed a little outside of Town near the Buttermilk mountain, - Aspen is actually made up of 4 mountains, not reachable from each other.  A little outside of town, a little lower cost, and since I was 1, alone, and 2, beat after skil lessons each day, I didn’t have much exposure to the ultra high cost of goods and services you hear about.

Fur, real and fake, was everywhere, and I guess this year's jeans look ('denim trends') is a ‘baggy’ blue jean with a loose cut.  Maybe this is old news but I don’t get out that much.  High platform Ugg-like shoes.  It’s a happy place of success and leisure.  I liked it.  Lots of private jets in and out of the airport, and at least the public building of the airport is a bit surprisingly worn and threadbare, like the town is trying to ‘keep it real’, at least at the airport.  With one runway for both incoming and departing flights and unpredictable weather it can quickly become a mess of delay, cancellations and frustration.  Not sure where in the Northeast you can fly directly into Aspen, but it’s not Newark, and regardless of where you are coming from, it’s on a smaller jet, and at least in the case of American Airlines, this felt like not their serviced and high-end line of aircrafts.

So, all in all, a 10 out of 10.  Learned to ski better, got to see Aspen, the weather cooperated, and now I’m home safe and it’s snowing, so my dog and I are just lounging around in my comfortable and quiet home. I'm definitely good at picking a random place to go to, find lodging and logistics and what-have-you, and have a jolly old time.

And as expected, my team in the office and field held down the forts.