Skippy Mesirow is the only member of Aspen City Council who has not previously served in that roll. He will serve as the council representative on the APCHA board.

Aspen’s only newly-minted, first-term council member Skippy Mesirow can’t go more than five minutes talking about policy without someone stopping him to say hello. Sitting at the base of the Silver Queen Gondola, he shakes hands with a longtime local businessmen, a popular nightclub DJ and the younger brother of someone he went to high school with.

One week on the job, he said he hasn’t had any steep learning curves yet, but he has been pleasantly surprised by his cohorts.

“I underestimated alignment on policy — there’s more than I would’ve thought,” Mesirow said.

The harder challenge, he said, is the pace of the process.

“So much of what you do is how you talk to one another, how you work with one another, and you really have to be rowing in the same direction to execute,” he said.

The new council has a retreat scheduled for the first week of July. Mesirow hopes they can use that time to create some aspirational bullet points for their time working together. He suggests things like, “I will practice radical honesty, I will not ascribe motive, I will not leave questions unasked.”

“I’m really grateful to be on a council with four people who I really respect, each of whom brings a different perspective set of experiences and thus a different value to the conversation,” Mesirow said. “If we do it right we will be better than the sum of our parts.”

After he was elected in March, Mesirow reached out to scores of people whom he wanted to learn from, including city staff, past representatives and members of the business and nonprofit community. He also wrote an email to every council member, trustee and mayor in the valley, to set up regional meetings.

“It was a simple message, I think we are better if we think regionally,” Mesirow said.

Related: Office hours with Torre

He suggested biannual meetings with each council in Snowmass Village, Basalt, Carbondale and Glenwood Springs, as well as resurrecting the State of the Valley Summit.

“That’s something that was really well received and at first read I think it’s got a shot,” Mesirow said.

Skippy will be the voting city council member for the reconstituted Aspen Pitkin County Housing Authority board, a role that mirrors his priority for his term. He wants to workshop and reevaluate the presumptions of the program through community dialogue. He referred to the stated goal of APCHA housing 60 percent of the workforce and he added housing Aspen’s retirees and youth into those goals.

“Sixty percent is an assumption based on a 25-year-old conversation. I want that conversation again,” said Mesirow. “I want to start with a new social contract and a participatory collaborative process.”

He hopes to hear from all citizens about whom the housing program is meant for, what role it is meant to serve and what the intended benefits are. That includes those in the system, those who want to be in the system and those who will never participate in the system.

“If I am living in it what is my responsibility to the people who paid for a large part of my house? If I don’t live in the program but I’m funding it, what do I get back in terms of community or access?” asked Mesirow. “And then you put that all into the abacus and you spit out a number, how many units do we need to reach those goals?”

Mesirow joked that he has a 109-point plan to improve the affordable housing system, but he sorts those objectives into three main goals. He said the first goal is to fix the current stock. That includes bringing buildings up to date and repairing structural problems. Next, he said there are ways to optimize free market and affordable housing to get the most use out of what is already available. The last step is to build.

“How do we create new units, both government and private built?” said Mesirow. “Not just ‘build, build, build, spend, spend, spend,’ recognize that we can make simple changes to underlying incentive structures and get private sector developers to build affordable housing.”

Mesirow also hopes to build off the momentum of previous voter participation campaigns. As a member of the Next Generation Advisory Board, he worked to get younger citizens to participate in elections, including providing rides to the polls. He was also the force behind a successful push to move Aspen’s municipal elections from off-season to ski season, which was carried out for the first time this March.

“Last election [there was] 21 and 24 percent higher [participation] than the last all-time high, for regular and runoff,” he noted.

Mesirow is not satisfied with increased turnout, though. His goal is full participation from every registered voter.

“I want to see Aspen become the first city in the country with 100 percent voter participation and do it in a mimicable way that other communities across America and the democratic world can copy,” Mesirow said.

Mesirow is happy to give out his cellphone number to constituents, and can be reached at his city email. But the most prominent way he connects with the public is through his constant stream of video uploads to Instagram, through the stories feature.

Often directly after a meeting, be it with a concerned citizen or an official council gathering, Mesirow will take a selfie-video, walking through the city streets recounting the points that were discussed and actions that were taken.

“Most of it is boring, but the response from people is amazing. They are like, ‘Oh, I get what this job is now,” Mesirow said.

Related: Richards ready for another go-round on city council

Often people will then reach out directly through the Instagram platform with more questions, or offering their own thoughts. The videos get somewhere between 150-250 views each.

‘Which I think is more than watch city council meetings,” he joked.

As the one millenial on council, he also sees a changing landscape in society as a whole. He said individuals want to be involved in everything from products to policy, and stress accessibility and transparency.

“We used to say sausages and laws are two things that people don’t want to see made,” said Mesirow. “Now, everybody wants to know how the thing is made, they want to know how to make it themselves and they want to be involved in the process.”

Because of sunshine laws, city council members cannot meet as a group without it being considered a public meeting. Mesirow said this means a lot of times things will be hammered out in the public eye that are not yet fully thought out.

“We have to stop being terrified to workshop things in public, to have a devil’s advocate as part of the process,” Mesirow said.

Mesirow said he is glad that other council members will be championing other pet issues of his like the environment, childcare and health care. So he can stay focused on housing and civic engagement.  

“If you want this to be a great community, first people have to live here, then they have to be involved in shaping it,” Mesirow said. “Everything else follows.“

Editor’s note: This is part of our entrance interview series, featuring Aspen’s three new elected officials. A piece about the new Mayor Torre ran on Tuesday and an interview with Rachel Richards ran Thursday.

Alycin Bektesh is a reporter for the Aspen Daily News. She can be reached at or on Twitter @alycinwonder.