The Bottom-Up Revolution
Strong Towns Chicago learned that fun isn't frivolous — it's essential for sustainable advocacy. Leader Alex Montero shares how the Local Conversation group uses urbanist comedy, neighborhood tours, and social events to keep volunteers energized and engaged while winning real policy changes.
Transcript (Lightly edited for readability)
Hello there, and welcome to this Bottom-Up Short. I'm Norm with Strong Towns, and I'm super excited to be able to connect each week with Strong Towns advocates and members and participants in this bigger work of building stronger communities across the North American landscape and increasingly in other parts of the world as well.
In this episode of Bottom-Up Shorts, I'm excited to introduce you to Alex Montero. Alex is one of the core leaders of Strong Towns Chicago, and he is a supply chain consultant by day and an urbanist nerd, by his own description, by night. He cares deeply about living in walkable communities and helping others to see that where they live as well, and helping people really understand and grapple with how regular decisions that are being made are having such an impact on our communities.
I also love that he is a local comedian, bringing stand-up comedy to various places to be able to introduce folks to his version of urbanist comedy, and I definitely want to dive into some of the questions related to that. You can find Alex online at Linktree slash urbanist comic, for those that are able to use that service, Linktree slash urbanist comic. Or you can go online and find the Strong Towns Chicago group, or just show up and visit. I had the privilege of being able to do that with Alex and the folks of all of the Strong Towns Illinois groups, and we were able to connect together and really enjoy that time. So Alex, welcome to Bottom-Up Shorts.
Yeah, thank you for having me, Norm. Glad to be here.
I'm really excited to have you on, and I would love to hear you describe the work that Strong Towns Chicago is doing. Maybe even share just a little bit over the holiday break what that looked like for your group and some of the things that you've seen beginning to take fruit in your work.
Yeah, of course. So Strong Towns Chicago was founded in 2022, but most of the growth and membership and volunteering that we've done, we've really seen since 2024, so about a couple of years now. There was a happy hour that was set up by one of the original founders where Chuck Marohn was going to be in town, and so we invited him to come to that. That was a draw for a few people who had signed up for the Strong Towns Chicago newsletter, because at that point, Strong Towns Chicago was just that, a newsletter, and some people sending interesting articles to each other. A lot of people had signed up for it over the previous two years. There was finally an in-person IRL chance to meet other people and meet Chuck for the people who showed up early enough.
A lot of us who met at that happy hour afterwards stayed in touch, organized different kinds of things we were excited about in the city, started talking and started really doing actual advocacy, and really pivoting from being a group that talked about things to being a group that helped nudge things in the right direction.
So the three main areas of focus that we have as a Strong Towns local conversation are abundant housing, safe streets, and effective transportation. That, as you can imagine, looks a little bit different in a city of almost 3 million people like Chicago than it does in some smaller communities. But a lot of the principles that Strong Towns promotes are still just as valid. We in Chicago have a lot of legacy housing stock. The home that I live in is 137 years old, and that's not unusual at all in most of the city. Most of the growth that happened happened in the early 20th century.
So there was a lot of existing housing stock, and then the city had a bit of a population loss after the 50s. So for a long time, it didn't seem like housing and having enough housing for the people who lived in the city was that big of a macro problem. Except now Chicago has started growing a little bit again. A lot of the legacy housing stock is not easy to renovate or rebuild, and so there is demand for additional homes for people who are coming in, starting families, young professionals, all of that kind of stuff. There's a term we use in Chicago for people who are not from here but are living here now, which is transplants. I would say that our group is about half people who grew up in the city or in the area and half people who are transplants. Everyone's passionate about the city. They love it. They want to stay here. Really, part of the advocacy we do is trying to make sure that we can afford to live here in 10 and 20 years and raise families here.
On the safe streets side of things, Chicago does have a lot of really good, walkable neighborhoods, but it also, like a lot of other major American cities, has plenty of stroads and arterials that have prioritized wide lanes and vehicle speeds over it being safe to cross. We're pushing really hard to bring Vision Zero to Chicago and actually make it so that we have zero pedestrian fatalities across the city. So it's a real and present issue for us that we're pushing on.
For transportation, famous as far as U.S. transit goes, we have one of the better and more extensive metro systems in the country, the L. Most of it is elevated, which movies love to show. The establishing shot of the L crossing over next to a building, and it's an extensive system. It serves a lot of people. We also have a really good bus grid network, but it's one that's had some challenges in recent years with being able to keep the service level up so that people can rely on it and use it to get to work and amenities and everything else that they have going on.
So plenty of areas where there's the Strong Towns message of working incrementally, seeing what we can do, doing the next smallest thing first, and thinking in terms of what are the blockers. In housing, often zoning. In transportation and street safety, often focus on permanent projects where concrete is being poured versus quick build and those kinds of tactical urbanist interventions. So a lot of the toolbox really applies really well in a city like Chicago and in all of the different neighborhoods and community areas we have here.
You have some very serious resource constraints and the need to get creative because the help is being reduced, or there's fewer opportunities for sort of big, speculative projects to be undertaken when there's just a lot of that core work to be done.
One of the things that stood out to me as I learned about your group and the work that you're doing is the way that you've used neighborhood walking tours to really connect, I think, transplants and longtime residents. Do you want to share a little bit more about that, and especially the focus of bringing people from each neighborhood you visit into that walking tour as a key part of that?
The neighborhood walking tours, probably after the happy hour, were the things that brought in the most members. It's often the first event that people heard of us at and that attended. We also got a large variety of people at neighborhood walking tours. We've noticed that it also depends on the neighborhood, but it tends to be about 50/50. People who live in the neighborhood and just want to learn more about the place where they live or be able to share some tidbits about the place where they live with other people. The other half is people who, in a lot of cases, have not been to that neighborhood at all.
Chicago is pretty huge, and I think people who have come here for a conference or for a weekend or something have probably seen the Loop downtown. They've maybe gone to Navy Pier. They've maybe gone to West Loop or some of the areas that are closest to our core downtown. But unless you've spent a longer amount of time here, you've visited family that lives in some of the outlying neighborhoods, there's a lot of really cool parts of town with really great cuisine history that people don't get a chance to check out.
So we wanted to be an opportunity for that, for people to get to know their own neighborhoods better, but also for people to have a reason to go with some friendly peers and get to know a place that they hadn't been to before, and hopefully see and discover things that would get them to come back.
So it's been nice in each of those. Chloe, who is our lead, who has run those over the past year and a half, she's been very good about reaching out to the local alderman, which is our version of city council member, and trying to get them to come to the walks, which we've actually managed to have three of them join us on a neighborhood walk and give their own insight of what they think is the cool parts of the neighborhood and the challenges they have and tidbits of history.
We've also been good about partnering with neighborhood organizations. These sometimes are philanthropic social organizations. Sometimes they are urbanist-related groups that are hyperlocal, the local cyclist union or safe street union or that kind of thing. Sometimes they're just cultural interest groups, local preservation society or something. But we always try to bring in somebody who deeply knows and cares about this place and have them really share on the tour and in the stops we make about this place they care about so much. It makes it so that it's much less generic, and usually most of the neighborhood walks that we go on, by the end of it, we've learned a ton, which helps.
Yeah. Can you share just a little bit about being an urbanist nerd stand-up comic, leader of a significant local conversation, and somebody that I think was really looked to for leadership and guidance for a lot of the other local conversations that are taking their cues from what you folks in Chicago are truly doing? Do you want to share just a little bit about your background and maybe some of those unlikely paths that led you to this point?
So I have loved cities forever, and I joke sometimes that my gateway drug into urbanism was public transportation. I've been a train fan since I was a kid, and bus networks, regional rail, subways, all that kind of stuff. But I think as I got older and as I lived and engaged with the city more, what became clear to me was that you can't just care about public transportation in a vacuum. If the land use isn't right, then the transit system is not going to be used, and you might have some really cool, shiny stations and vehicles that are chronically empty and only have a fraction of their potential because once you get off the train or the bus, there's nowhere to go.
So the land use and housing and commercial corridors and all of that tying into that, and also street safety, because pretty much everybody who takes transit starts as a pedestrian, whether they're walking or rolling. They have to get to the stop into the vehicle first. So street safety is incredibly important to having that. Starting to see it as a bigger pie did a lot of reading, did a lot of watching the usual suspect YouTube channels, Not Just Bikes, City Beautiful, City Nerd, all that kind of stuff.
Around the time I got involved here locally in 2024, it was really I was tired of just reading about stuff and watching channels where they were preaching to the choir. Maybe I would learn a couple of interesting nuggets of things, but I was like, "Okay, what can I actually do about this?" So signing up for the Strong Towns Chicago newsletter and then getting involved in active advocacy was my chance to say, "Okay, how can I help nudge things in the right direction locally?" It's been incredibly rewarding and satisfying. I would say that for most of the people in our group, it's the same kind of thing. None of us gets paid to do this. In fact, if anything, we lose money because we each chip in to keep the website up and everything else. But it is absolutely worth it for us.
Everyone has day jobs and other things, and so really, the challenge and the question becomes, "What can we do as volunteers to be the most effective and get the most impact and the most joy out of the time that we dedicate to this," considering that everybody else has other things going on.
For myself, a scene that I was very heavily involved in prior to urbanism was the Chicago comedy scene. The scene here is great. I did theater for fun in high school and a little bit in college, and I stumbled into the improv and sketch and eventually stand-up scene. I started doing improv at Second City, which is well known, an institution here in the city. A lot of cast members and alumni from SNL started here. Keegan-Michael Key, Jordan Peele, Tina Fey, a whole bunch of folks.
It was cool there for a couple of reasons. Number one, it scratches that part of your brain, gets you outside your shell, gets you comfortable with being uncomfortable, with being creative, with rolling with things. But also that the comedy scene in Chicago is pretty diverse, pretty spread out. There's, aside from the big places like Second City, there's a ton of hole-in-the-wall theaters in some random corner of some neighborhood. You walk up to the building, it looks condemned, but you knock on the door, you walk up the steps, and you see they have a show at the top.
So really, I credit the comedy scene for getting to know a lot of neighborhoods in a lot of parts of the city and starting to appreciate the different pockets of urbanism and how neighborhoods felt different. Different ones did things better than others and everything, because that scene and having gigs in different parts of town took me to a lot of corners that I probably wouldn't have gone otherwise. It's been nice to see that I'm not alone.
There's another one of our leads, Ellen. She is also still heavily involved in the comedy scene. When we were advocating for transit to get state funding to prevent transit fiscal cliff as COVID relief funds dried up and there wasn't state funding to backfill that and keep service up to what the city needed, we were advocating for that heavily this summer going into the fall. Thankfully, Illinois passed a transit bill recently, so there is funding for the next couple of years and in some cases a net increase for operational costs to pay for maintenance and drivers and all those things.
One of the big things in that push that we did was Ellen organized a sketch show with a little bit of improv, advocating for transit. Making sketches out of, "How did we get in this situation? How is it that the tollway and other roads and so on seemingly have a bottomless pit of money that they can use for their projects, but for this stuff, it dries up? How did that happen? What are some things that could be used? What's the dynamics of all of the different stakeholders who weigh in and move things in some direction?" In Illinois, it was hilarious. It was really funny. It was good.
It managed to attract as guests, in the middle of the show, they would usually have a little break and invite a guest up who had something to do with this issue. We got Dorval Carter, the head of the Chicago Transit Authority, to come to one of the shows and talk about why transit funding was important. We got a state senator and a state representative. They were going back to Springfield to talk about this stuff, but they made time to come to our show and be guests for it.
That helped get a little bit of press coverage too, where a couple of local newspapers talked about the show and the people who were on it. It was kind of neat too to hear some of those same people later in press conferences and in debates on the House floor using some of the same talking points or little tidbits that Ellen had put in the show. So it's one of those things of media is really powerful for getting people to pay attention to things. But yeah, there is, I think, space for a transit-themed comedy show or a walkability-themed comedy show that gets some people to come out and listen to this stuff and engage with this stuff in ways that otherwise they wouldn't. It's been really, really cool to see that.
Because there's layers of absurdity, but not hopelessness. I think that's the key. There are things that are just ridiculous or bonkers, and yet in their own way, as you begin to chip away at it, you realize, "Huh, there actually are things that we can do, and even find a little bit of joy in doing them," that are going to help to improve people's conditions and our own conditions too. Like you said, to be able to live in the city and to be able to afford it and get around without having to pay an arm and a leg for it.
Maybe that touches on a question that I love to ask, of your whole sort of stock of ideas and suggestions, what would be a few tips and suggestions that you have for folks that are interested in taking this on in their community as well?
So one thing I would say, as someone who hasn't been an advocate forever, I've been heavily involved in this for the past couple of years, and I have learned a ton of stuff, is two things.
Number one, don't be afraid to admit ignorance. I think there's a tendency a lot of times for this kind of stuff to think that these big issues are solved by some lone genius. So if you haven't studied the textbook and you don't know all of the formulas and you don't know exactly the mechanics of how things get funded or engineered or built or something, that you're not allowed to weigh in. But the truth is, I think the things we've been able to accomplish as a local conversation have been precisely because none of us has a complete picture, but each of us has a little piece of experience or information or perspective that put together with the other folks actually becomes useful.
So it's the thing of don't be afraid to admit when you don't know something. Learn from other people who do know things or point you to resources and directions. I'd say that that level of humility and openness to experience and intellectual curiosity is really important if you're going to be doing this kind of thing, because you will always have people who you're trying to influence or trying to convince or who are pushing back against something you think is important that are going to know more than you. The only way you overcome that is by learning more, but also surrounding yourself with other people who know more.
The second one there is, I don't know how this is going to come across, but I would say if you're a volunteer, you can't treat this like a job. You have to know that there are limits. It is good to be passionate, and it is good to want to get things done, and it's good to be accountable, and it's good to have goals and track all of that. But as I said earlier, none of us is getting paid for this, and there are moments where people have to flex.
It's happened to us with some of our leads where life got in the way. There was something more important they had to do or take care of, or someone they had to help out, and they had to take a step back for a few weeks or months, and then potentially, when things cleared up again, they jumped back in. So it's being able to give yourself the grace of doing what we can, to use the Strong Towns recurring refrain, doing what we can to make our places better. Sometimes we can do more and sometimes we can do less. It's important to be able to lean on your fellow advocates when life happens and you need to take a step back, or be able to help out your fellow advocates when you have some bandwidth and maybe they don't.
So those are the two main things I would suggest to anybody, and a last bonus one is just try to have fun. Because this is a volunteer activity, I feel like if you're just fighting the man day in and day out and you can't find little ways to have joy about this kind of stuff, whether it's doing the neighborhood walks or putting on something more creative like the comedy show or having social gatherings, it's really easy to burn out. Some of those people who you meet who can help you accomplish things, you meet in a social context, and then they help you out on the harder stuff, like giving public comment and writing editorials and trying to meet with local aldermen to nudge things in the right direction. So have fun with it, because that's the way you stay involved in it and want to stay involved in it.
Yeah, I love that, and it doubles down on something that I've shared now dozens of times after hearing it from you, which is that your group went through an exercise of identifying your broccoli items and your ice cream items. So what are the things that are energizing to you, and then what are the things that you're, "You know, I am willing to take in my broccoli, but if there were somebody else for whom this was ice cream, that would be amazing." That realization, "Oh, somebody's ice cream items are actually another person's broccoli items," is one of those things where you begin to see how broad that bench can really be as you help one another.
So just yeah, great, great suggestions, great advice. Love that. We'll have to bring on Chloe because she's also so full of similar good material. As we close, I'd love to hear what is it that gives you hope as you continue at this?
What gives me hope is things are starting to change in ways that are encouraging, and there's a broader coalition of people who get this, including folks in City Hall and folks who work for folks in City Hall and members of other organizations that haven't seen this holistically. They were focused on their own little piece, whether it was cycling advocacy or environmentalism or anything. We're starting to see that really looking at the larger umbrella of things that is the built environment and urbanism is how we make progress on a lot of these things.
So it gives me hope to see that in Chicago, we got massive parking reform as a city this year. In 74% of the city, there is no minimum required parking anymore. That's huge, and that's something that probably a year ago, people would have told you was never going to happen here. So even though the fights are tough sometimes and there are setbacks and there's pushback, it's promising to see that things are actually starting to move in the right direction.
A lot of folks who didn't used to talk to each other now are. We just had for Christmas what we call the Big Ten Urbanist Christmas Party. This was something that I set up with the person who ran CMU Chicago locally here a couple of years. Since then, we've had a few different events, but it's basically the "Let's get all of the people who are working on these related issues together and get them to just meet each other and talk with each other and get to know each other in a fun, social context." Every time we do one of those, more people go off and do a project that they wouldn't have if they hadn't met each other there. So it's encouraging to me that things are moving in the right direction, and also people are talking, which is the first step in any of this.
Yeah, that's fantastic. Keeping people talking, ensuring that people are doing things that give them energy and create the potential, at minimum, to have fun, as well as to recognize, yeah, there can be that joy or that delight, even in times that are challenging.
So Alex Montero, it's been wonderful to have you on Bottom-Up Shorts. Thanks so much for making time for this.
Yeah, thank you for having me, Norm. It's great.
And for folks that want to check out the work that Alex and the Strong Towns Chicago group are doing, definitely check out their website, check out their social media feeds. Go find Alex on Linktree as well. Let me just grab that link one more time. It's urbanist comic, and there you might be able to catch even a little bit of his stand-up. I think there's probably something like that on there.
But folks, I hope that you've appreciated this Bottom-Up Short and continue to hear more from the folks in Chicago, I'm sure, as we go forward. Keep doing what you can to build strong towns and take care of your places.
This episode was produced by Strong Towns, a nonprofit movement for building financially resilient communities. If what you heard today matters to you, deepen your connection by becoming a Strong Towns member at strongtowns.org/membership.