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If you have to ask how much it costs to live in Aspen, Colorado or Jackson Hole, Wyoming, you probably are also secretly asking yourself, “Should I move there?”

And it’s a natural question. I recently caught a glimpse of some of the trails that our contributor Paddy O’Connell runs on near Aspen and my first thought was how staggeringly gorgeous they were. And how jealous I was. Jackson Hole is a place I try and visit friends in every other year or so and it’s hard to sip hot cocoa and watch the elk migration without thinking: what WOULD it take to live here?

But one of the perennial, never-ending stories we’re also always covering at ���ϳԹ��� is the increasing inaccessibility of these kinds of high alpine communities. In 2017, a print story by Tom Vanderbilt, “Did AirBnB Kill the Mountain Town?” raised the possibility that the short term rental app would eventually price out not just ski-bums and dirt bags, but you, me, everyone. Last year, in “To Save the Soul of a Mountain Town” we looked at what Aspen has already lost with the construction of so many ten-million-dollar second homes.

Our stories are, essentially, chronicling the five stages of grief. And recently, Paddy O’Connell and Frederick Reimers, who goes by Rico, reached the stage where you just sort of complain and argue over who's got it worse.

Paddy O’Connell: Aspen and Jackson Hole are two of the best known ski towns in the country, and for good reason.

Rico Reimers: They both have world class skiing, extensive trail networks, and beautiful rivers running through their valleys. Oh and super avid outdoor communities.

Paddy: There's only one, small, incy wincy, teeny tiny problem...it's damn near impossible to live in either place if you're just a regular human that does not have several trust funds. I am such a regular, mere mortal of a dude, who lives in the Greater Aspen Area. And so is my buddy Rico here, who lives in Jackson Hole.

Rico: Let's just say neither Paddy or I own a Fortune 500 company. I did just sell a couple of pairs of rock skis at the ski swap, though, so I've got a little money in my pocket.

Paddy: Ohh, nice! We're talking literal tens of cents, people. But when it comes to living in these famous ski towns, near impossible isn't impossible, and we love it. Sure, it's challenging as hell to make it work, but primo skiing in our backyard makes it all worth it. But that's not exactly why we're here today.

Rico: We have a score to settle.

Paddy: That's right. Because Rico and I were chatting recently after having both taking epic wiggles out our backdoor, we started to wonder: as members of our respective towns, who has it worse? I mean, we obviously know Aspen has the better skiing, but I'm here to argue that the wealth factor in Aspen is just way more absurd than in any other ski town. And it's getting worse.

Rico: Woah, woah. First off, Jackson's skiing beats Aspen any day of the week, But I have to put up with way more big dumb hats than you do over there in Aspen, paddy. I think Jackson residents have it way worse.

Paddy: Then let the debate....begin. First topic to prove that I am right--rich people fashion sense. And for that, I'm going to call my first expert witness.

Rico: We can do that?

Paddy: Yeah, dude. This is podcasting. We can do whatever we want. I don't even have pants on right now. - Pause for Rico reaction - Anyhwo, I call to the stand my good friend Gordy.

Rico: Wait a sec, Gordy's my good friend. He lived in Jackson for a decade.

Paddy: True. But in 2021, he moved to Aspen and subsequently ripped up your friendship contract. Ok, here's Gordy on Aspen's tres gauche fashion.

Gordy: walk down the streets and , it's like the, the outfits that the guys wore in Dumb and Dumber when they, you know, found out that they had a briefcase full of cash. Like being dressed in a certain way, seems to be a big deal around here.

In Aspen, you go to a bar, , after skiing, and, people are, wearing those crazy Bogner outfits and like fur boots and cowboy hats and whatever. And that's what they want to be seen in that light. They want to be seen as, you know, one of these people who are, you know, they're almost like a caricature of a person visiting Aspen.

Rico: Ok ok, sure, Aspen gets a little cartoony, I'll give you that. But I was part of that conversation, and a little cross examination will show that Gordy had a few points to make about the absurdity of Jackson's dress code, too.

Gordy: in Jackson Hole, what I noticed and I always thought was kind of funny, was people, you know, coming down from skiing the pass and going into the coach and like, they still had their beacons on.

And, like, that's what they wanted you to know, that they were out, like, you know, skiing in the backcountry and they were hardcore. Maybe they moved from New York a year ago, but this is what they're doing now.

 

Paddy: At least those folks in Jackson Hole are actually skiing. I'm going to take this point, because the cartoon fashionistas in Aspen are just playing “ooh, look how big my credit card is”  in all the fancy shops in town. They don't actually ski. And Gordy agrees.

Gordy: what I always thought of Aspen is like, this is where the very, very wealthy people come to party, you know, and I think that Jackson is catching up in that department But, like, Aspen was always, to me, like, where Hollywood came to ski.

There's obviously some incredibly difficult slopes at Highlands and at Ajax. really Challenging terrain. But you know, people would come here and maybe they don't even ski. And I think that's still the case. And I'm sure you'd agree with that. People come here just to be seen.

Paddy: See, Rico?! One nil Aspen!

Rico: Ok, fine. But Gordy agreed with my mountain town rich guy archetype hypothesis.

Paddy: I thought I destroyed this tape.

Rico: I saved it from the trash.

Rico: Here's my pet, , theory is that like the prototypical celebrity in Aspen was like Trump, right? He would show up wearing his Bogner and his whatever trophy wife of the day.

And the prototypical celebrity of Jackson is Harrison Ford. who still insists that he's a carpenter. Ha ha ha

Gordy: yeah, and Harrison Ford, I used to see, you know, having a cocktail at Local, just sitting there with one of his buddies.

And then, yeah, nobody bothered him, and then he would just get up and leave.

Rico: just wearing like Levis

Paddy: I'm like more and more regretting having the two of you on microphones right now

Rico: See? Yes Aspen has over the top uber rich folks but at least they're not pretending to be some downhome, blue collar rancher. So that’s a point for Jackson, and we are tied, 1-1. Jackson is worse.

Paddy: Wait a sec, Rico. You’re saying Trump is authentically Aspen and you’re claiming Han Solo/Indiana Jones for Jackson?! I’m taking extreme issue here.

Rico: What I'm saying is the richy riches in Aspen are unapologetic about their wealth. There was this Yale professor, Justin Farell, who came to Jackson to study the one percent of the one percent for his book Billionaire Wilderness. I picture him like Jane Goodall, except he's nibbling pate in the corner of some 20,000 square foot house. One of his points was that Jackson's richest residents cosplay dirtbags, filling the closets of their second homes with Carhartts and flannel shirts to strut around in. They’ll even have an “a�ܳٳ��Գپ���” Jackson car to tool around the valley. like an older F150 or something. Their so-called valley car.

And they see their boot fitters and their private chefs as genuine friends but they are totally blind to how transactional those relationships are. Soooo that is another point for Jackson and the scoreboard reads 2-1 Jackson on top. Or should I say, bottom.

Paddy: Yeah OK, fine. But here’s one. And Gordy backs me up on this, rich people in Aspen sponsor the cool kid skiers just to hang out with them. And that is way worse than donning flannel like costume jewelry.

Gordy: they'll cozy up with one of these very good athletes in, , the Roaring Fork Valley and they'll, you know, then. That that person will sort of be like their, you know, ski buddy to Europe or wherever.

I don't remember that happening at Jackson. That's not to say it didn't, maybe you've seen it Rico.

Rico: Yeah, I think I've seen it as people will hire like literal guides, to guide them, but they're not like their pet skier per se.

Gordy: I feel like it's more of a pet skier thing here.

Rico: And you're a good enough skier, Gordie, you could have been a pet skier for a Jackson family.

Gordy: I wish I was a pet skier for somebody.

Paddy: Gordy, can, can you be my pet skier? I can only pay you in goldfish crackers and mustache furs and hugs and hugs and those friend,

Gordy: That sounds like

Paddy: Those are priceless

Gordy: sounds like a terrible deal.

Paddy: So there, in your face, Rico. 2 to 2.

Rico: Ok, fine. So Aspen has the more ridiculous displays of wealth. And Jackson has, let’s call it, an authenticity problem. But let’s bring it a little closer to home. Who has it worse when it comes to the heart and soul of a ski town–the ski bum?

Paddy: Isn’t that like trying to crown the winner of a dog turd eating contest?

Rico: The winner of What?!

Paddy: Like, there is no real winner here?

Rico: Well, that’s kinda what Gordy said. But not as gross.

Gordy: You still see people who are, ski instructors, waiting tables, maybe they're mountain bike instructors or building houses or whatever in the summer, but you've got to work so hard to live here now, even If you're, you know, living down in Glenwood or living over in Victor or Driggs.

In both places you're starting to see the ski bum sort of disappear, right? Like, you can't actually live a ski bum life in either of these places anymore. It's too expensive. unless you come from wealth. Like, that's. not possible anymore. You know, the rents are so expensive here and in Jackson now. especially the last couple of years during inflation, it was made it particularly hard to live here.

Everything you earn is going to go back into rent and food and, it's a hard place to live now, if you really are, coming here to live as a ski bum, it's tough. You're going to have to work hard and you're, you're going to have to expect to not be able to save any money.

Rico: Ok, sooo, this one may be a bit of a tie, which as a “former ski bum who is still pretty much a ski bum” is really flippin’ sad.

Paddy: Agreed. Neither Jackson or Aspen make it easy to get a goggle tan. So the scoreboard reads 3 to 3.

Paddy: Do you have any advice for somebody who wants to move to either Aspen or Jackson and make a go at the ski bum dream?

Gordy: Have a rich family.

Rico: I mean, a big ol bag of loot certainly wouldn’t hurt.

Paddy: Yeah, it wouldn't. I'm still waiting to find mine though...

Rico: Maybe Jeff Bezos left one for you at the St. Regis ski boot valet?

Paddy: Ha, unlikely, but I'll check tomorrow just in case. Maybe he parked his rocket ship on Main Street.

Rico: Good luck with that. But, I think I get a point here. Because unlike my home of Jackson Hole, there are folks in Aspen, despite the 1-percent of the 1-percent being all 1-percenty, who actually are making the dream happen.

Aspen Mikey: people. Definitely say, Oh, how the legend. I'm like, dude, I'm just a guy who likes to ski a lot.

Paddy: You are crossing the line, Rico. You can’t use Aspen Mikey against me!

Rico: Too bad, PaddyO. Jackson 4, Aspen 3.

Paddy: Absolutely not! Will you excuse us please? I have to yell at Rico.  More Aspen vs. Jackson after the break!

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Paddy: Ok, Rico, what does the scoreboard read?

Rico: So far it’s 4 to 3, Jackson over Aspen. Meaning, I am winning the “who has the most ridiculous ski town” contest. But I am about to pull away with what I know about ski bumming in your neck of the woods.

Paddy: Ooooh I see how it is, you’re gonna use my pal Aspen Mikey against me. Ok, cool. I’ll remember this, Rico.

Rico: Shaking in my ski boots over here. But first, a little context is needed. To understand just how difficult it is to make a go at the ski bum dream we need to figure out whose housing market is more absurd.

Paddy: By absurd I’m sure you mean barf-inducing because trying to rent or buy in ski towns is like trying to stomach a weeks-old gas station sammich.

Rico: It’s truly nauseating. Living and skiing in Jackson Hole and Aspen is arguably the hardest it's ever been. You could definitely buy a private jet for less than the cost of a house in one of these places.

Paddy: No kidding! Last Spring, a house on Red Mountain outside of Aspen sold for $108-million, which is the highest sale in Aspen and the state of Colorado EVER! Oh, by the way, the previous record was $77-million...which was set just 5 days before! So, ah-doy, Aspen gets this point.

Rico: That’s bad. But Jackson is even worse.

Paddy: Huh, how? Aspen has close to 75 billionaires who own commercial or residential properties...in a town of 6000. There's so many on Red Mountain they call it Billionaire Mountain.

Rico: Welllllll, Jackson Hole is in the wealthiest county in America. In 2021, the average per capita income was more than 300 thousand dollars. Pitkin County, where Aspen is located, was second at just under 200 thousand dollars, so point for us. Plus, Teton County is the most unequal county in all of the unequal counties: the top 1 percent of residents bring in an average of $22 million annually, but the median household income is just $94 thousand. It's so expensive to live here, doctors are priced out. My wife's OB/GYN's office closed in part because they couldn't hire new physicians...because they can't afford the housing here.

Paddy: Doctors can't afford to move to Jackson?

Rico: Nope. The average home price topped 7 million dollars last year.

Paddy: But the average sales price for a house in Aspen is $10 million.

Rico: Well how about this: there is no state income tax in Wyoming. A guy I know saves $100 million in taxes by moving to Wyoming. Every year. $100 million.

Paddy:  Ha! The uber loaded spend that much shopping here. Aspen’s got stores where a jacket costs more than my mortgage. Gucci, Prada, Dior, Louis Vitton, Valentino, Moncler. I literally walked into a store the other day and flipped over a tag on a pair of pants, and BLAMO, $11,000 dollars.

Rico: Ok, that's absurd. But what the hell were you doing in that store?

Paddy: Shoplifting.

Rico: What?!

Paddy: Nothing, nevermind.

Rico: Well, we've got people who spend $30K a month to heat their driveway so they don't have to shovel snow.

Paddy: We have subterranean skyscrapers.

Rico: Subterranean SKY Scrapers??

Paddy: Height restrictions in town mean folks build down. Think underground basketball courts and movie theaters.

Rico: That’s literally the opposite of a skyscraper.

Paddy: Ok, fine. Core of the earth scrapers. But now we have depth restrictions. (pause)

I feel like we both are getting points for extreme over the top richy rich mountain town facts...and yet, we are both losing. But the scoreboard reads 4 to 3, Jackson worse. And now I think we play some sad music...

Rico: Yeah, or you go skiing.

Paddy:

Sooo that brings us back to Aspen Mikey, huh?

RICO: Yes, yes it does.

Field Tape: Good to see you. Good to see you too. How are you? Good. Yeah. Yeah. I had to rip a quick lap. Oh, that's all good. I Should we go skiing? Yeah, I think we should go ski fast to the bottom. Okay, I'll follow you

Paddy: Maybe unsurprisingly, the best place to conduct a "hey you want to discuss the state of ski bumming" interview is whilst actually skiing. So I went to my home hill, Aspen, the greatest ski hill in all of the universe...

Rico: Meh, second best.

Paddy: ...to chat with a skier who's been slimeballing the system in Aspen for the last 40 years, a guy known simply as Aspen Mikey.

Paddy skiing: I'm putting this recorder away so I can go skiing. I gotta keep up with Mikey.

Paddy: Quick note: I did not keep up with Mikey. But I caught him at the bottom. Mikey's is the "classic Aspen tale":  boy attends CU Boulder. Boy feels aimless after two years of school, boy thinks "I'm gonna take a year off and ski bum." Boy goes to Aspen sight unseen in October of 1980...and that one year off turns into 44 years.

Rico: Yeah, but a key piece to Mikey making the dream happen is APCHA, the Aspen/Pitkin County Housing Authority.

Paddy: Ah, eff word! I’m gonna lose this point. You know about that?

Rico: Yeah, somebody's gotta be the journalist here. Not all of us can play professional baffoons on TV Paddy.

Paddy: Ouch, but fair point. Also, shameless plug for season 2 of my TV Show "PaddyO Sucks At" streaming on ���ϳԹ��� TV. Ok. Go ahead, Rico!

Rico. Ok, so, APCHA began providing affordable housing to the Aspen and Pitkin county workforce in 1974. APCHA has over 3000 units today, both rentals and homes to own, which is far ahead of Jackson. We've only got 1,056 units. Though, a couple of summers ago people were allowed to live in their cars in the rec center parking lot. provided they were town of Jackson employees, and ponied up $465 a month. So you have no argument, point for me. Living in Jackson is almost untenable.

Paddy: Yikes. Yeah, it’s yours.

Rico: Aspen is able to have more affordable housing units because of the real estate transfer tax. One percent of every real estate sale goes to funding affordable housing. Two years ago it generated $22.5 million.

Here in Wyoming, the legislature has so far blocked Teton County from passing a similar tax. In Aspen, folks like Mikey can make it if they can get their foot in the door with APCHA.

Aspen Mikey: I used to live at a great little property called the Hunter Longhouse, built I think in the seventies and It's one of the least expensive place in town, but I always lived in a two bedroom with a roommate to keep my cost down. And then this spring, a place came up near Park Circle. And it's all Category 1 housing, which is Basically, you can't make more than, I think it's, the cap's 40, 000. So it's basically low income housing, and it was available to the person with the longest proven work history in Picken County. And now I'm pretty much set.

I'm blessed that I have super cheap rent and finally got my own place for the first time in 22 years. Unfortunately I don't own my place, but my rent is so cheap that I can afford to work only 30 hours a week and still make it.

So for me, it's still very doable.

Paddy: Ok, I love Mikey. And the fact he's making it work in Aspen is amazing and admirable. But having APCHA doesn't mean it's easy street for everyone. Are you really gonna sit here and tell me and the bajillions of ���ϳԹ��� Pod listeners that there is not a single professional couch surfer in Jackson Hole?!

RICO: Well, snuggling up to a sugar daddy or momma for housing has a long history here.

Paddy: Like Gordy's pet skiers, but for a different activity...

Rico: Exactly. But I did chat with this one guy in Jackson who is aspiring to be like Aspen Mikey. Though he has to literally get creative to make it all work.

Ryan Stolp Interview 22:30 - my, uh, platform is, uh, four inches by five inches and, uh, limited to one to two sentences of dry humor

RICO: Ryan Stolp draws a comic strip called Lift Lines that pans mountain culture. He moved to Jackson in 2015 and started the comic strip as a way to make sense of the job shortage, the privilege, all things mountain town. And, like Mikey, Ryan's had to figure out the Jackson housing labyrinth. He spent a few weeks on a friend's couch when he first moved here. And then found a roommate through Craigslist.

Ryan Stolp: We kinda hit it off and he had access to a lease above a bar. It was 700 bucks a month. That is way different than it is now. You know, a factor of 3 or 4 now. Like that change allows, allows you to show up and take a risk or allows you to maybe have more of a work life balance.

Like you could probably make that work on one job. I was lucky and able to make it work on starting a company, you know, like that was a lot of freedom.

Rico: what about your friends? Like, how are they making it?

Ryan: Most of them moved to Idaho, which is kind of our commuter workforce community.

Um, it's over, I would say, one of the more treacherous passes in America. Schools close when it snows and they have to do avalanche mitigation. There was a bank robbery on a powder day a couple years ago. Because all the cops are dealing with traffic and avalanche issues, and like, if that doesn't say that that, like, having a remote commuter workforce community is not the best solution.

Rico: Honestly, I feel like Jackson Hole folks...

Paddy: Jay Holes, as they're referred to.

Rico: Ha. Not wrong. The Holers have it harder. Like, the imposing economics here make the ski town barter culture look like something out of a Mad Max movie.

Paddy: Ah, yes, let us begin the bro deal debate!

The barter culture, I think, embodies the community it takes a village vibe here.

I mean, I think that's like a ski town, rule of thumb, you know, Oh, I need a wax on my skis. Here's some beer.

Like, you go ski the pass, your plan can be to hitchhike back to your car. Or, , hey, I want to go ski Targhee. Can I trade something to someone who might have some extra comp tickets? Or, restaurant workers that get a bunch of leftovers and throw a dinner party or something.

Rico: The bro deal system isn't just for getting yourself a free ski tune or a slice of pizza. It can get you big ticket items, too, like a place to live.

My landlord for my apartment building has a list 200 people long. You're getting in the building because someone was like, Hey, Matt, you should bump this person atop. I can vouch for them.

They're a good person. And they might've been sleeping on a couch for a while. Like it, that is the only way it's relationship based that things are going to happen.

It's what makes things feel like community.

People yearn for that. People want to feel. Known, accepted, cared for, looked out for. , like, the safety net here where things are so thin is your friends. , my family lives 2, 500 miles away, , if a car breaks down, I'm not calling my dad to come pick me up.

It's like, oh, who can I, who do I know that things go around, come around?

Paddy: Ooookay, I am going to take the point here. The skiers helping skiers community is alive and well in both places, but Jackson sounds all sorts of kumbaya. Like it’s the frosty mountain town version of a Peter, Paul, and Mary concert. Clearly, I get the point.

Rico: Hold up! First of all, PP and M is a great band. Second, yes, it’s fun to game the system with your friends. And it definitely helps keep costs down. But bro deals only exist because so much of life in mountain towns is out of reach for your average everyday ski bum.

Sometimes it’ll help you mount your skis, but sometimes it’ll help you with essential needs like housing and work.

Bottom line, the shockingly wealthy who continue to pour into Jackson Hole need to start valuing the rest of the community.

Paddy: Yeah, that’s true no matter the town. Because the ultra rich need us normal folk to survive. Cause you can’t shovel your driveway with your trust fund.

Ryan: You know, you have a privilege to be here, too, and it's not a right to be here. Um, does the community need people of lots of different means and abilities and passions and expertise and professional abilities? Yes. And that's where there's a trade off, and I don't, I don't know how to, um, I mean, at some point, the people at the top will recognize that, like, the things that make this a place that they want to be, you have to feed and nurture.

At all levels of the community, you know, like if you like going to the farmer's market, but you never help support these struggling local farmers that are getting priced out because their property taxes have quintupled in the two decades they've run their farm, you're not going to have a farmer's market.

But that tension, I think it'll always be there. It's always, um, it seems to be always in the back of people's mind, the tip of their tongue. It's on the sideline of any issue in town.

Everything changes. And I guess, I moved here from a city that doubled in size when I was growing up, Durham, North Carolina.

People were complaining about the change there too, but what you can do is, like, try to be active and steer it and engage with how it changes. And I would say, as a small, tight knit community, Jackson should get good points and strong points for that.

Paddy: Dear sweet lord, Rico! See how hopeful Ryan is? Game. Set. Match, my friend! Aspen wins, in your face. There just ain’t no walking away from that youthful optimism right there.

Rico: Hmm, maybe you’re right. I mean Ryan's in his 30s. And unlike some wrinkly aging ski bums, he doesn’t have to pop ibuprofen like TicTacs because his knees make sounds when he walks like some O’Connells I know.

Paddy: What, you mean like this sound that my knees make? (SFX)

Rico: Who the hell is editing this thing? Point is, Ryan’s young, sure, but that doesn’t mean he’s naive.

Ryan: I'm not so much optimistic that in 20 years, Jackson will be back to this culture that I fell in love with. Is it like, there's a solution,  we can roll back the clock? No, like we're not gonna make Jackson great again. Like, I mean, it can be great in its own things, but it's not gonna be the same as it was.

I would love for people to take that step back and understand what's going on. And particularly people of means, which great, you like, you've arrived. You achieved the ability to.  Come live in Jackson, and that's awesome. But, if you want it to be Jackson that you think of, and why you chose Jackson over somewhere else, you have a responsibility to engage with what makes it that way, and to nurture it, so that it can be the way that it is in your head.

Rico: This is hardly a comprehensive scorecard of Jackson vs. Aspen, but Paddy, even though Jackson got more points for being worse, I don’t know who wins here

Paddy: Yeah, agreed. I wanted this to end with you having to fashion some sort of trophy for me out of an old ski boot. But I gotta admit, when it comes to issues like wealth disparity and housing insecurity in mountain towns, no one is really winning. Everybody loses when a community feels fractured.

Rico: No doubt. Jackson's former town manager likes to say that the only way to stem the influx of millionaires would be to slow internet speeds to 2008 levels. Poof, goodbye remote workers.

Paddy: Um, Rico, WE are both remote workers.

Rico: Ugh, that's true. Slow internet would mean we'd have to move to some city, get some 9 to 5 office job where you actually have to go in two days a week. We'd never ski powder again.

Paddy: Calm down, dude. We're ok. We'll always have skiing. The billionaires are totally gonna solve climate change. And you can always visit me in Aspen…(under breath) for the best skiing in the country…

Rico: Second best.

Paddy: Ugh,

Field Tape: Woo!

Oh yeah!

Alright!

fun. That was super fun.

Beat

The Gospel of Wiggle. Is alive and well.

Peter: That’s Paddy O’Connell and Frederick Reimers.

This episode was written and produced by Paddy and Rico, with editing by me, Peter Frick-Wright. Music and sound design, by Robbie Carver.

The ���ϳԹ��� Podcast is made possible by our ���ϳԹ��� Plus members. Learn more about all the benefits of membership at ���ϳԹ���online.com/podplus