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Skippy Mesirow, in bid for a second term on Aspen's City Council, brings new ideas, including a vacancy tax

Incumbent city councilman Skippy Mesirow laughs during his Squirm Night appearance on Wednesday, Feb. 8, 2023, at GrassRoots TV in Aspen. (Austin Colbert/The Aspen Times)
Austin Colbert
The Aspen Times
Incumbent city councilman Skippy Mesirow laughs during his Squirm Night appearance on Wednesday, Feb. 8, 2023, at GrassRoots TV in Aspen.

Skippy Mesirow was elected to a four-year term on the Aspen City Council in 2019. He runs a vacation rental company in town.

Reporter Caroline Llanes spoke with Mesirow on Feb. 2, 2023 at Aspen Public Radio.

This is the third of three interviews Llanes conducted with the candidates running to be elected to Aspen City Council this year. Previous interviews with Sam Rose and Bill Guth are on the Aspen Public Radio website.

You can alsolisten online to the interviews with the two mayoral candidates, Torre and Tracy Sutton.

Ballots for the Aspen's municipal election went out to voters last week, and in-person early voting started Feb. 21 at Aspen City Hall near Rio Grande Park.

Election Day is March 7.

Interview Transcript

Caroline Llanes: Let's start really big picture, really high level here. What do you see as the biggest issues currently facing Aspen?

Skippy Mesirow: What are the things that if we change those, they will make everything else change, or they will make doing everything else easier? And so to me, there's two off the top, very clear, and it's housing and it's governance. You know, it's housing, stupid. If we don't live here, who are we solving this problem for? And with whom are we solving it? Right? We actually need the bodies and the minds, and then we got to enjoy it.

The other is governance. You know, I think if you look at a variety of our missteps and there are many, both personally and collectively, they tend to be issues of process. And that's a thing that, you know, very candidly, most voters yawn about or just don't understand. And fair enough, because this is a weird world. But this is not a problem that's isolated to Aspen. The entire democratic world is experiencing what happens when a 17th century system designed to solve 18th century problems fails to meet 21st century expectations.

I think we are in perhaps the most unique and special place to solve those problems for ourselves, but they could also replicate out to the rest of our nation and our world. And when we do, many of the issues and roadblocks and conflicts we have can be resolved through better process. So I think those are the top two.

Llanes: Okay. Let's start with that affordable housing question. For a lot of people, it's the single biggest Aspen issue and has been for years. What are you hoping to do in this space should you win another term?

Mesirow: There's a lot of things. I mean, housing has been my number one issue and we have gotten a ton done, especially in the last year-and-a-half. But what I'm trying to do is put out ideas that can make fundamental change to start conversation.

What we've seen for the last 30 to 40 years is workers who were already here were living in, you know, the stuff you could afford to rent. And over time, that's been replaced by nonresidential use, whether that's STRs or, increasingly, vacant investment properties. 68% of our free market is vacant investment, and so what's actually happened is displacement. So what I'm proposing is we've already passed a city-approved STR tax. We should pass a voter-approved—it has to be voter-approved—vacancy tax. What that would do is, say, either you choose to house a qualified worker and you pay nothing, or you pay into the system.

And critically, those dollars are deeded, so they only go to non-new development solutions.

One of two buckets: either A: we put dollars in your pocket qualified worker, Caroline, so that you can go buy an existing free market unit that you couldn't otherwise afford in exchange for a forever deed restriction. You get housing, today, the city, the community gets affordable housing forever. We haven't laid a brick and it's cheaper than building something new.

Bucket B is we give it to the development community and we say next time you're going to tear down a single family residence, build—which you now can because of the work in the moratorium—high density, affordable housing, and we're going to balance that budget so your investors know you're making the same returns are better for delivering what the community needs.

Now, we've aligned development interest with city interest and we're going to start seeing that pop up all over the place.

Again: no new development, less money, faster. If 20% of our vacant structures were filled, we would effectively build three Lumberyards in three years for $0. If those housed just one person, we would build an entire Lumberyard’s worth of housing without laying a single brick and saving the taxpayer $400 million.

How can we not consider that?

Llanes: Okay. Let's talk now about the Entrance to Aspen. It's a hot topic. Everyone's got thoughts, everyone's got opinions. How are you feeling about the conversations council is having both with stakeholders and with the community about this project?

Mesirow: I mean, I've been super clear on this for years at Council, at EOTC. I think we're asking the wrong questions. I think you have to decide what you want to be before you decide how you want to enter it.

And there's a variety of things I hear across our community that we haven't yet solved for, right? I hear, “all the affordable businesses are gone. I don't have a place–even if I live here, I don't have a place to go, and be.” The segmentation of the classes is growing and we don't like that. And I hear that from everyone, whether their income statement starts with a, B, you know, or a T—that’s thousands, if you’re wondering.

You know, everybody seems to miss that and we have an opportunity to cultivate it. The primary driver of our self-observed problems are scarcity of space. It costs a lot of money to do anything in Aspen. It's not the business owners fault. They’ve got to charge a lot when their rent is X dollars. It's not the landowners fault that there's that scarcity of space and there's demand. These are high-class problems.

But we as citizens, we own the streets and currently we are choosing to allocate that hyper scarce resource to park cars. It's about space use. We say we want affordable business. We say we want places to convene. We say we want clean air and environment. We say we want places for connection. Well, it's time to transition the streets to do that.

We can have free on demand all electric transit to where you want to go. If you want to go to a local business or a non-local business or an expensive business, instead of circling around to park for an hour, you just get dropped right there and get picked up with your bags. Right? We can maintain egress for fire safety and deliveries. These are not technological problems.

And in the middle of those blocks, we can have a local business district where we allow space for affordable, small businesses to flourish. And because they are in the middle of the street next to the high end retail, we necessarily cultivate an environment where people intermix across incomes and we can re-instill the commons, and we have to work with our local businesses that remain to do this, because it is those businesses who have somehow made it work who are going to be best able to tell us what the business community needs.

Llanes: Let's talk about climate. The city has some aggressive climate goals …

Mesirow: Yeah, that have been adopted by this council!

Llanes: How do you feel about the work you've done so far? Do you feel like you guys are on track?

Mesirow: I feel great about it. I mean, our community was, if not the leader, one of the leaders in the world for a long time, and we've really reclaimed that leadership position. Amongst many things, including net zero energy goal by 2050 and the rest of it, what I'm most excited about is how we have begun to deal with waste.

If we don't have to produce new goods to displace old goods that in many cases were totally functional, then we make a significant impact to our landfills, to our waters, to our rivers, to our land, and to our CO2 profile.

Let's call a spade a spade. Aspen is arguably the most consumptive place on the planet. So if we can prove that without significantly reducing our lifestyle, we can be net zero waste, well we have set a model that every community in the world can follow, save, maybe Monaco. So great! Let's lean into that.

And I want to give a lot of credit to our mayor on this one. He's really, really pushed this. And I want to give a lot of credit to John Doyle, who from day one on council has come in with news briefs about the environment at every meeting, laser-focused. It takes five votes and it takes a staff to do all of this, and our staff is incredible. Those two gentlemen have really driven a lot of change.

Llanes: So with regards to this current council, there's been some criticisms that the council frequently votes five–zero on a lot of issues. How would you respond to those criticisms?

Mesirow: It does entertain me a little bit that at this moment in American history we are upset about not having more divided government, and the concerns are valid. And I've talked to people and, you know, a government of groupthink is not a good thing. It's also not what's going on.

To look at the number of final votes and come to the conclusion that that started as unified vision is completely inaccurate and suggests you haven't watched work sessions. And by the way, like, please don't bore yourself watching work sessions. That's not your job. But at the end of the day, we have very divergent views on a lot of things. And we came together and said, ‘Where's our Venn diagram? What can we really do together? Because our community needs to see things change coming out of COVID,’ and we focused on those areas and within those we all compromised a lot. There was a lot of stuff in the moratorium and in various policies that I didn't agree with. The same is true of Ward and Rachel and Torre and John. That's what consensus is. So I think you've looked at a functional government over the last year and a half that I've been happy to be part of.

That said, I come from a Jewish tradition. It's fundamentally different than how most people approach politics in America. We tend to be very conflict-averse in America, we talk around things, we point fingers, and we blame. And I don't think it's helpful at all.

And I think that culture needs to shift in our tradition—what’s up, tribe!—conflict is the tool by which, knowing we're all pointed at the best outcome for all, we create the friction to create ideas that are better than the sum of their parts. And we could use more of that on council. We could build that into the process so that there's more expert and divergent testimony. We can listen to more opposing opinions, and we've done plenty of it.

In the moratorium, I can point you to several things that were not in the plans until the development community got in, and now they're in the plans and they're being done. So we've done it. But I do think we can do a much better job.

Llanes: What would you say sets you apart from the other candidates? Why should someone vote for Skippy Mesirow?

Mesirow: I'm actually putting out ideas. If you go to my council page, you will see a number of big ideas that this council either doesn't agree with or has not taken up yet. I'm trying to move the conversation our community deserves. New ideas and new approaches, and I think that does set me apart.

I also am someone who has a proven record of putting community interests ahead of self-interest. I run a vacation rental company and I supported the highest vacancy tax on council. Now, I believe that's also good for the business. I believe that if we didn't support that and I'm not here and we can't hire any workers, that business closes, right? I believe that. My industry doesn't necessarily believe that. That wasn't an easy thing to do.

And you're looking at it. You can't see it on the radio. But, you know, in front of me is Joe Edwards’ initial platform, you know, [Bob] Braudis and Art Daily were critical parts of my team in 2019 and 2017. I have had the opportunity to like, literally live and talk with legends, to work with Joe, to work with Michael Kinsley, to work with John Bennett, and to have the support of the people who built this community, have a direct line and lineage to them—I mean, I feel like I'm talking to George Washington. And they and that ethos and that spirit are central to what I'm trying to help us all remember, revive, and re-enliven.

Llanes: And I also wanted to ask about this new coalition. Aspen deserves better. They have quite a few criticisms of city council and the actions they've taken, especially over the past year. Have you spoken with them at all?

Mesirow: Absolutely. I speak to everybody. I appreciate critical feedback. Yeah, I've sat down with Alex George, with Peter Grenney. I consider them both friends.

I don't feel threatened by this, as some do. I think Aspen does deserve better. No matter who's in leadership, we should always strive to improve our community. I love the objectivity that they're bringing, in most cases, to things. What I said to Alex is, “I hope you guys solve a problem that we failed to solve.”

We have not figured out how to communicate with the public in the way that we want to, as judged by the public's feedback of how they're feeling. I want to get to a government where everybody feels seen, heard, included, and where the outcomes align to what we need as a community. We're not there yet. That's okay. Neither is anyone else in the democratic world. But it is our job to continue, right? I mean, we say in our tradition, right, that—I'm paraphrasing, sorry, Rabbi—it's not our job to complete the work, but neither may I desist from the effort. And that's how we should think about democracy. We should make improvements. So I want to work with them and everybody else.

Llanes: That was Skippy Mesirow. He first was elected to city council in 2019 and is running for his second term. Skippy, thank you so much for taking the time to talk with Aspen Public Radio. We really appreciate it.

Mesirow: I appreciate you.

Caroline Llanes is a general assignment reporter at Aspen Public Radio, covering everything from local governments to public lands. Her work has been featured on NPR. Previously, she was an associate producer for WBUR’s Morning Edition in Boston.