The Bottom-Up Revolution
In this episode, Josh Olson reflects on how he and others helped bring a Strong Towns local conversation group back to life in Madison, and kept it going with simple habits like reserving the same library room each month. It explores the projects that grew out of that effort, including safer street trials, Parking Day, and support for a major housing reform package. As the group took on these projects, members built relationships with city staff, showed up to public meetings, and pushed for small, low-cost changes—like turning a peak-hour traffic lane into parking—that the city implemented within months.
Transcript (Lightly edited for readability)
Hi everybody. Welcome to another episode of the Bottom Up Revolution podcast. My name is Tiffany. I am your host. Today we're talking to someone who is very familiar with what it takes to build a movement in his community from the ground up, using our local conversation group model.
We've had a lot of people on the show who have been involved in local conversation groups, who are leading them, who are growing them. They're all unique — as unique as the town that they represent, the town that they're working in. Building a local conversation group and really bringing the Strong Towns conversation to your community takes a lot of patience and persistence. It's not a magic trick. It's not immediate success. Sometimes you have to start and restart. You really have to be patient, figure out what works.
I think our guest can speak to that — to the value of patience and persistence, and to finding small things you can do to get going and then watching traction build over time. I'm really excited for him to bring his insights to the show. What's also exciting is he's representing a community that his group has nominated as part of our Strongest Town contest. So maybe we'll get a chance to talk about that as well.
Josh Olson is, as I mentioned, one of the co-coordinators of the Strong Towns Madison local conversation group. He's called the Madison area home for about eight years now and loves it. From what I hear — we've had a chance to talk before this recording — he keeps tabs on local issues and stories on his blog, Counting Cranes. We'll put a link to that in the show notes.
Josh, welcome to the Bottom Up Revolution podcast. Happy Monday. Thank you for being here to speak with me.
Happy Monday. Thanks, Tiffany, for having me.
So you grew up in California, Josh, but you call Madison home, and you have loved being there despite the snow. Every time I mention Madison, everybody says snow. So tell me, what makes Madison feel like home? Why did you choose to settle there? Maybe you can tell us a bit of your story.
"Despite the snow" is really funny, because for me, it's actually part of it. I went to UW–Madison, studied chemical engineering, and I absolutely fell in love with the city. It's growing. It's unique because it's situated on an isthmus, which means it's got two relatively large bodies of water right next to it. That makes for a really interesting physical layout. The seasons are really nice, too.
I grew up in a hometown next to another town whose motto is "Climate Best by Government Test." It was around 50 to 80 degrees the entire year — just all the same. When I arrived in Madison, even though I got to experience the snow — and honestly, February and early March are the worst times; we just had a blizzard, which was pretty crazy — it makes me appreciate the incredible weather we have in May.
It opens your eyes. You have to have the lowest lows to have the highest highs and really appreciate what you're living with. This weekend it was 70 degrees, and everyone knew Sunday was going to be 40 degrees, so everyone was out and about doing things. I went on a bike ride. I'm talking to my coworkers today and they're saying how much they wanted to get outside. It's great. That's one of the main reasons I love Madison.
Separately, my hometown is really expensive. I was looking at some notes, and over 50% of owner-occupied homes are worth more than $2 million. I'm not going to buy into that. I just needed to find a new place that really fit my needs — a place I could actually invest in and buy into.
Well, first I have to say that I totally understand the weather thing. I'm in Texas — came here from New York — and people are like, "Wow, three quarters of the year is relatively good weather." I was like, yeah, but it's not natural. You should suffer.
I mean, just look at me.
You need the cycles, the ebbs and flows. It layers on. It's part of what it means to be a human being. You see some of the cycles of just existing mirrored in the natural world. There's something kind of good about that, even if it's not always comfortable. We have 70-degree weather in November, and I'm like, I guess it's nice to be wearing linen on Thanksgiving. But then I raise a fist to the sky — it's not natural, Texas.
Get it right.
Do you have any memories of when you realized, "Oh, this place is home?"
I think a lot of it came from COVID. I graduated in 2021, so in 2020 I did not listen to my chancellor. I misread an email — she said everyone should go home, and I thought it said everyone should stay. My fiancée and I were one of very few students left in Madison during that time. We were just walking around, constantly talking to each other. It was so quiet. I really got to appreciate the build of the city and the neighborhoods.
I was also there through May, because normally I would fly back to California at the end of the semester. I really got to experience the incredible time that is May and June in Madison — everyone's out and about doing things. It made me really want to figure out how I could stay in the area.
So there was a practical side to this search for home. We were looking to stay in the Madison area post-graduation. One thing we had to work around was that my fiancée had to work in Beloit — about an hour south of Madison — for six months after graduation. We were trying to find housing that fit our needs, with easy highway access to make that commute as easy as possible, while also managing cheaper rent. We were just graduating and didn't have a big emergency fund.
We moved to the outskirts of Madison and it worked for a year, but even with the cheap rent, it was pretty isolating. We knew what the well-built neighborhoods within Madison felt like to walk through. We wanted to find a place like that within our budget — one that would allow for the kind of housing we were looking for.
In terms of how that got me to Strong Towns: I was worried about costs. I was looking around and seeing that we're on a similar trajectory to my hometown — making the same decisions, maybe just two or three decades behind. How could I be part of moving us off that pathway where everyone's priced out and you have to keep moving further and further out into the ring of suburbs? Can we start doing little things to make it possible for people to find homes?
One of the first things was an ADU item I read in the newspaper. I started reading the newspaper a lot more once I graduated — very adult, I know — just to stay informed on various housing decisions. I saw an ADU item and it mentioned the Plan Commission. I thought, I think I can go speak to that. I was also watching the Not Just Bikes Strong Towns playlist around that time.
I want to slow the camera here a little bit. How did you even know you could go talk at that meeting? Most people don't even know that's an option. You're reading the newspaper — major points — you're putting the pieces together and thinking, "Oh, I can go speak at this." Was this just something you already knew, or did you figure it out? I just don't think that the problem-solution-action process is second nature to a lot of people.
My guess is, when I read "Plan Commission did this thing," I didn't know what Plan Commission was. I looked it up. That probably directed me to the city website, which said, "If you have comments, you can submit them here." I think I emailed the Plan Commission. There are some really nice people on those committees. That probably made their day — I do have some funny stories about that.
Honestly, being polite to people gets you really far. I probably emailed them and was confused because we had this old Legistar system that tracks all the agenda items for city government — it doesn't make a lot of sense. I think someone probably just walked me through it and said, "Here's how you register to speak. You'll get your three minutes, and you can say what you want as long as it's related to the topic at hand."
From there, once I started showing up to those meetings, some people clocked me. They had my email because I was writing in public comments, and they were reaching out saying, "We should have a conversation about this." I even had conversations with Plan Commission members or city councilors — we call them alders. Outside of those formal settings, many people are really accessible and really willing to help.
Have you always been that kind of person, though — like, "Ooh, public comment, that's my jam"?
No. I've had issues with public speaking for a really long time — it ranges back to elementary school. It's a fear that I've gotten over. Even when I'm standing up at the mic for public comment during our city council meeting — which is called Common Council, just in case any Madisonians are listening — I still get nervous. My heart's racing. I don't know if I'm going to say the right thing. I usually have to have notes in front of me.
But it's three minutes, and if I make a fool of myself, it's okay. I think it's important to speak up for these things. In the separate conversations I've had with alders, they say they need people to give them permission to say yes. That's one of the main things. It's easy to say no to things. They need people to show up and say yes. The hard thing is that complaints and negativity really drive people to show up, and rarely is it positivity that motivates someone. So it's a breath of fresh air for a lot of them when someone comes in and says, "I want you to do this. I think this is a good idea. Please pass this."
Yeah, that's great. Can you continue the story for us? You start showing up, you start building these relationships, having these conversations, going to these meetings. How did that eventually bring you to finding Strong Towns and ultimately to the local conversation model?
I was watching the Not Just Bikes Strong Towns playlist. From there, there was a member drive and I signed up to be a Strong Towns member. I got an email talking about local conversations. I looked up the map, found an email listed there, and got in contact. Strong Towns helped us facilitate a meeting. I think that was in February of 2023.
It was cool. We met at a coffee shop, walked around the local area, and saw some things we thought we could improve — like, could we add a trash can next to a bus stop? There was a lot of litter around. There were a couple of other small things I noticed. I met a deputy mayor at some random event and said, "Hey, there's a bus stop that doesn't have a bench. We should get one there." They did it. But our meetings kind of fizzled out from there and didn't really continue as much as I wanted them to.
A lot of conversation leaders have been in that place of wanting to get things going but having a hard time building momentum — whether it's finding the right people, timing, weather, all kinds of reasons. That's something you experienced — taking a few tries to get the conversation going. Can you tell us how you navigated that, and maybe some tips or insights looking back?
Even though our conversation didn't continue consistently the first time, I was still monitoring a lot of various advocacy groups. I saw a Reddit post that said, "Hey, we're starting a Strong Towns conversation." I thought, interesting — I'm technically already part of one that isn't really going. Let me reach out to this guy. So I messaged him. This is Mike, who's one of the other co-coordinators now. I said, "Hey, you're doing this — technically we already have a group, but we're not doing a whole lot. If you want to restart this, let's do this. I'm motivated to make it work."
I had us listed as a group for the library, where we actually still meet to this day. I committed to continually sending the email to the library reserving Central Library Room 104 from 1 to 3pm every first Saturday of the month. I said to myself: I will continue to do that until this group disbands. That gave our group the stability and consistency needed for people to show up.
Mike also really helps with ensuring people show up — he manages the agenda, we take notes, we add follow-ups. Having small commitments that you know you can do well allows people to trust that showing up is worth their time.
It allows people to take their own autonomy and own their own projects. We've done small projects outside of that. I did the crash analysis studio — that was something I wanted to own. I owned the nomination for the Strongest Town contest this year. Mike really pushed us through Parking Day last September, which was his own crazy snafu, but I'm glad he did it. It was a moment for us to say, "I can do this. I'll grow my skills. What else can we learn?" Other people have stepped in and contributed their own unique views, skills, whatever they can bring. It's allowed us to become something really cool.
I'd love for you to share some stories about what you've all been able to accomplish as a group since then. You mentioned a couple — Parking Day, nominating your town. Love to hear more.
This restarted in 2024. The thing we wanted to get done that year was just meet consistently. We tried to make some signs and were tabling at the Dane County Farmers Market, which is like the largest outdoor farmers market in the US — thousands of people every weekend. It was a great opportunity to build brand recognition and talk to people about these ideas. We've had some interesting conversations. I know Mike's talked to people who said, "I completely disagree with you, but I'll hear you out." Those were unique moments. We want to be able to speak to everyone.
At the end of 2024, Tony Harris from Strong Towns reached out and said, "Hey, you should nominate your city." I said, "We're new. We haven't done enough. Talk to me next year." At our meeting, we decided we're going to do some things so we can be nominated. One of those was Parking Day, and another was the opportunity with Willy Street that I talked about on a different podcast with Norm — getting lanes reduced from four lanes to two lanes, and highlighting changes from a crash analysis studio that we wanted to see made.
Can you walk us through that street one? You talked to me about that before, and I thought it was really fun. I think our audience would really enjoy hearing that story.
Once upon a time, in an eclectic part of Madison called Willy Street, one of the co-coordinators — Mike — lives in the area. There's a coffee shop called Mother Fool's that has been crashed into three times in the last two decades.
I have to say that I appreciate your story having a coffee shop in it. What a great name for a coffee shop — and how unfortunate. I've seen this whole cars-going-into-buildings thing. It's happening where I live. Okay — Mother Fool's on Williamson Street, three times a car has gone in. This poor coffee shop.
We said, we can't let this happen again. Mike is part of the local neighborhood association. They brought it up to the Transportation Commission: this has happened three times, this is unacceptable — if it happens again, what are we going to do to prevent it? So they brought in city staff. City staff went through a couple of options. One was putting bollards at every intersection on Willy Street, which would cost $600,000.
Another option was essentially just education — an easy thing to commit to if you're a city staffer with limited resources and a tight budget.
Then there was the idea that a lot of us were pushing for. I'm sure it's been in the ether forever, but the issue is that during commute hours — 4:30 to 6pm and 7:30 to 9am — parking is removed from the outer lane. Cars are then traveling faster in that outer lane, which is the one closest to the businesses. Even if this particular crash didn't happen during those hours, it's not safe. Speed studies had confirmed that.
The proposal was: can we just put bags over the signs that designate a peak-hour lane and instead make it a parking lane all the time? We posed that to staff. They said they'd think about it, but we had to come back at another meeting and ask again. We had a second meeting in August. I was on a work trip, on a treadmill, basically live-tweeting in our Discord what was happening. We had at least five of our members speaking up and saying, "We should trial this. This is not a huge deal."
Staff was suggesting potentially spending $100,000 to $200,000 on a consultant, then waiting three years because a big reconstruction project was planned to start in October, and it wouldn't be fair to run the test during that reconstruction. Essentially, "Let's look at this in 2028." We said no — you really should consider this now. The Transportation Commission was behind us. They said, "We think we should try this too." Staff asked, "Is this worth it? It's going to cost $24,000 out of the safe streets budget. Do you really want to prioritize this?" We said yes. They turned around immediately.
The meeting was in August. We had those signs down September 9, and they ran the trial through November. The fact that they were able to do it at roughly 90% less than what a full study would have cost, in about a month, and technically within four months of the crash rather than three years — that made me really proud.
That's amazing. A couple of takeaways from that. It's interesting that you understood who all the players were — you had staff, you had the Transportation Department, and I think that's really important to keep in mind. These types of conversations really do require talking to a lot of different people who have different constraints, different incentives, and different resources. Figuring out how to talk about the problem in a way that resonates with each player, relative to their constraints and priorities, is key.
It doesn't mean you have to know every project a transportation department is working on at any given time. It just means being able to acknowledge those constraints and keep them in mind. Being polite, showing up, offering support, staying positive goes a long way in helping those conversations move forward. And then what you brought to the table — an incremental, super simple, super quick idea — was not a big commitment. It was a test. Framing it as an experiment is critical, because you're not asking them to make a commitment. You're asking them to try an idea that's cheaper and faster than the typical path of a quarter-million-dollar consultant and three years of surveys. Just amazing. That's a perfect example of putting the Strong Towns approach into action. Any other success stories you'd like to share?
Parking Day is a fun one.
We tried to do it in 2024 but couldn't get it to work because it requires a special permit, which requires insurance due to liability. I started that dialog with the city about a month and a half before Parking Day, but the permit was due a month before. Good learning experience — we'll figure this out for 2025.
We thankfully reached out to some connections we'd made through various advocacy groups. They helped connect us with businesses or nonprofits that already have liability coverage built in. We found a business on Willy Street that was willing to host the event. They had the liability insurance. Then we just had to get the permit.
Part of what you pay for in the permit is barriers, since you're on an active street. Even though Willy Street is 25 miles per hour, we still brought our radar gun, and I caught someone going 47. We want to be safe. We thought the city was going to provide those barriers since we paid for the permit. But the city told us, "You're way too small of an event. You still need barriers, but you're responsible for bringing them."
So these things are 12 feet long. In our Discord, it was basically: how do we get these there? Who has a truck? Someone biked them over on a flatbed. Someone also had some unused snow fence, which allowed us to create a full perimeter even though the barriers didn't provide full coverage.
Those two combined allowed us to get commitment from the business owner the day before — she had been about to back out because she was worried it wouldn't be approved and didn't want to get in trouble. The city confirmed the permit was valid.
What we heard from some other groups was, "Thank you for doing this. We've tried in the past, and this gives us a pathway for next year." The head of transportation walked by on Parking Day, stopped, and introduced himself — he was brand new, just two weeks in. Mike explained the whole thing and the director said, "We've got to make that easier. It shouldn't be that difficult to get a permit for this." I don't know if that's been baked into the protocols yet. We'll see again in 2026. But our hope is that because we took this step and fought through that red tape, other groups will be able to do this next year.
What do you think the solution looks like — events under a certain size are just by-right? Just go for it? Can we have a "go for it" policy?
I wish. I just moved into a new neighborhood. There's a school and a fast road. I want it to be slower — people are going 30 or 35 in a 25 zone. I was asking, can we get a street art permit? Do those exist? I'm outside of Madison now, so this smaller city doesn't have the resources for that. I've been in conversations with city staff saying, "I know you can't do this now, but when you do have resources, can we have templates? So it's very easy for a neighborhood association to follow the template and put some cones up."
I would like there to be more opportunities for us to get to yes, rather than having to follow all of these specific protocols. It's good trouble, but the business owner nearly backed out because she didn't want to get in trouble. That's a huge obstacle for people trying to solve the problems they see — liability issues, permits they didn't even know existed.
There's a great opportunity for cities to re-evaluate how many of the rules in place are fear-based and bring some life back. How can we re-evaluate these so that there's a little more freedom for people to be part of making their town safer or more beautiful? If your mural is up to a certain size, you can do it by right. If you want to plant flowers, you can do it by right. If you want to put cones up, or have an event — a whole "go for it" attitude. People can figure out their own problems. We still need protection and permitting for some things, but there's probably a lot of opportunity to re-evaluate what that could look like.
So these stories you've told show that you've figured out, at least to some degree, how to navigate conversations with city staff and city leaders. I'm not saying you've figured it all out — I'm sure you consider yourself still learning. But looking back, what advice would you pass along to anyone who's in a conversation group or trying to do something in their town and needs to have those kinds of conversations?
The easiest thing is to be polite and be patient, because they're often overworked and have other things going on. There was a contentious area plan on the west side of Madison. City staff were getting yelled at — or at least there were very loud voices. On my bike ride home, I saw one of the planning staffers. They looked like a deer in the headlights. I'm sure they were thinking I was about to chew them out again, because I had been at that meeting.
I went up and said, "Hey, my name's Josh. I just want to say thank you for all the work that you're doing. I appreciate the lengths you're going to in order to meet with all of us and talk through these plans." Then I went on my way. I saw him a month later. He recognized me with a big smile and said, "I'm sorry I was caught off guard in that moment. You made my day. I told everyone at work the next day." I don't think they hear that enough.
Now, the one thing I'd add: when we invite city staff or elected officials to our local conversation, be careful. You might be sharper on these topics than they expect. Don't scare them away. If you start asking a bunch of questions about zoning codes, they might think, "I didn't know this was that kind of group," and become uncomfortable. It's a balance. You can get into the nitty-gritty with them — it's great — but ease into it.
I would add: maybe don't challenge them on everything, but definitely do your homework. I've seen the other side, where whatever they say, everyone just responds with enthusiasm without any critical thinking. Like, are eight more chain restaurants really our definition of economic success? It doesn't mean you challenge them directly, but it means doing your research and understanding how to interpret what they're telling you. There can be a time to ask a pointed question.
I think critique is good. It's almost about framing it positively so they stay open. You don't want to be the person who only focuses on negatives. I think it's fair to say, "I see an opportunity here — what's preventing us from doing this thing?"
Right. Maybe something like, "I know you're really trying to grow the economy, and I understand why bringing in more chain restaurants might seem like a good idea. I'm also really curious about how we can support more small businesses who can't open shop. What do you think we could be doing on that?" Finding ways to frame it constructively. At the very least, doing your research so you have something substantive to bring.
We had a lot of success because of that. Our crash analysis studio in 2024 opened the dialog around trialing something. The road we were focusing on was technically two lanes, with a slip lane on the right. Someone was killed because of a right-on-red. Based on Edward Erfurt's recommendation, I suggested to city staff on site: let's turn off this right slip lane, put cones up, and just see what happens with congestion. Is this right turn really needed? They said they couldn't do that — if they're going to invest in fixes, they want it to be permanent, with concrete rather than flex posts.
Then around March 2025, there was an issue with the Southwest Commuter Path. There's a train track right next to it, and the state's Office of Commissioner of Railroads said they needed better signage because cars were stopping on the railroad tracks due to pedestrians and bikers. I'll be the critiquing person here: this felt very targeted. They only called out this one intersection because of pedestrians and bikers, even though I see cars stopping on rail crossings elsewhere in Madison because of other cars. But we said, "This is an opportunity — if we're going to put up new signs, can we also reduce this from two lanes to one lane?" Transportation Commission said, "Let's try this." City staff said, "Fine, let's do a trial."
So we moved from "no trials at all, permanent only" to "let's consider a trial" — and then a few months later, Willy Street, same thing. Now the default seems to be: that trial worked, maybe we don't need as many lanes. The Regent Street reconstruction meeting we just went to a month ago — the preferred option reduces lanes. I don't think that would have happened if we'd been having this conversation two years ago.
That's where constantly making positive cases and saying "let's try this" — done in a polite and appropriate way — really pays off.
Absolutely. What you're describing is culture change. That's the other thing to keep in mind: it's not just about achieving one specific outcome. Overall, you're on a mission to help expand the imagination of what's possible — changing the culture around how we think about our cities, how we frame problems, how we pick solutions.
One group that I don't think we talk about enough, but that you've touched on, is business owners. I know from talking with you before recording that your group is thinking about how to bring more business owners on board, especially around parking reform. Can you talk about how you approach conversations with business owners? What are you learning so far?
I think you take every opportunity you can get. If there's a door that's open, go for it. Mike started our Instagram page and followed a local business group called Dane Buy Local. The person followed us back and sent us an email saying, "I was reading your page and this is all very interesting. I'd like to meet." So we met with her at Mother Fool's — I think it's a member of their group.
We said, "Here's kind of why we're here. There are opportunities to improve the lives of our civic members in the local conversation, but we want to expand and get the business perspective. Around 70% of Madison's revenue comes from property taxes, and businesses play a big role in driving those property values. Willy Street alone generates about $1.7 million for the city, all from local businesses. It's a really interesting area we wanted to get into."
After that conversation, she said, "You should come to one of our events." Right before the Strong Towns contest started, she sent an email on short notice saying if we could show up, please do. It was a quarterly meeting at 7:30 in the morning. I thought, I can do this before work — I'm just going to show up, put on a name tag, and meet people. They were saying, "Oh, I know Strong Towns," and having whole conversations.
I was thinking about leaving early because I had a 9am call. I stayed, and I'm so glad I did. She did something really nice — she didn't have to, but she said, "We have Josh here. Do you want to speak about what you're doing?" I said, "I'm here from the local conversation for Strong Towns. You may have heard of them. Madison is in the Strongest Town contest this year. We're hoping to drive some publicity. We want people to vote. However you want to spread the message, please do — otherwise, I'm just here to make connections." Five people came up to me after and said, "I know so much about Strong Towns — I didn't know we had a local group in Madison." These are the small steps we're taking to build these relationships, but we're really at the very beginning.
Business owners are sensitive to certain things, especially parking. How are you approaching that conversation specifically? I know we talked a little about parking benefit districts and rethinking what parking looks like in your town. Can you speak to that?
For us, it's about one-on-one conversations and asking, "What's the smallest thing I can do?" We can always show up to businesses and signal that we didn't drive — we biked. We wear our bike helmets. We tell them, "I was just passing by." My most recent blog post was about the Lake Loop, which is a great thing to do when the weather is nice — you can just bike around Lake Monona. I stopped at Level Five Donuts on Atwood Avenue the previous weekend for the first time. Delicious donuts. My friend who I was biking with had never been, and I was like, "We're right by it — let's just stop." We walked in with our bike helmets on, showing that we weren't there because of a parking spot. We didn't need off-street or on-street parking.
I read something from Angie Schmitt — I'm blanking on the title of her book, but she talked about how a lot of these trips are driven by not having a plan. You're more likely to stop by businesses when you're out on foot or on a bike. We want to show businesses that parking isn't what's getting people to their door — it's the place itself, the fact that there are interesting things to do nearby. I don't want my trip to a business to be a one-to-one errand. I want it to be a place where I can exist for an hour or so.
Conversations are starting, but it's hard. We would like to get businesses to at least be neutral on parking reform, even if they're not enthusiastic. It doesn't have to be a yes — just not a no — because business owners have such significant sway with city officials.
Getting them open to experimenting is key — small tests rather than big commitments. The book you're referring to is Right of Way by Angie Schmitt — does that sound right?
I think so, yes.
Business owners have been operating under the mythology for a couple of decades now that it's drivers who sustain businesses — that car traffic volume is an indicator of success, rather than pedestrian or cyclist volume. Trying to reverse that is a big part of the uphill battle: helping them see that activity on the sidewalks is what really supports a business. You can have a million cars drive by, but if none of them stop, what's the point? Optically it looks like it's doing great, but imagine if you just had a thousand people walking by. Imagine all the unplanned, spontaneous donut purchases that could happen.
Very difficult to be spontaneous in a car.
So difficult. Don't even get me started once you're a mom with kids in car seats. Spontaneous trips just don't happen. That donut better be incredibly good, and you better have a playground, if I'm stopping and pulling all my kids out of their car seats.
Growing up, I lived close to a downtown in a nearby city. One of my favorite memories was biking with my dad and my little brother to get local ice cream. That happened because there was a safe enough route that my dad felt he could take a six-year-old and an eight-year-old to the ice cream shop. We weren't going to drive to do that. It was an activity — it brought us to the park, and then after the park, the shop was close by. All these combinations. It's not an errand to go to the park — it's a fun thing, an experience.
So helping people get out of errand brain and into experience brain is huge. When you factor in a car and car seats, everything has to be planned. I'll take them out to do experiences, but maybe one a day. We have a new French bakery here in Waco — that was our excursion for Saturday. It would have been a lot better if I could have taken them on a bike. We could have popped into the vintage mall, gone to the farmers market, biked along the river — probably five more things we could have done if I didn't have to worry about the car, the car seat, the parking. Just totally different. Building places where people can have experiences — more experiences, fewer errands — that would be ideal.
Anyway, going back to business owners: they're a really important part of the conversation. They're very sensitive, and it's understandable — they've invested a lot and they want that investment to make good returns. It's probably a really long-term conversation. Lots of experimentation is critical there. Be polite, and take baby steps.
If you're walking or biking somewhere, I've actually suggested to a coffee shop owner here that they should give discounts to people who bike or walk in. Although it may not be the best location for that — they just built a bigger parking lot. So it's tough.
Tell us about the Strongest Town contest. This is your moment to shine. Then we'll wrap up with my traditional closing question.
Madison is in the Final Four. I'm calling it the Midwest Miracle, because it's three cities from Wisconsin and then Chicago.
I think Madison should get your vote. This contest is all about making progress, and I think we've made significant progress. We've made a lot of inroads with city staff — getting them to approach things on a trial basis. I really appreciate the fact that they've changed their stance on that, and I think it speaks to both their willingness to do it and their expertise in managing it well.
There are also some housing wins. There was a Housing Forward package in February of 2025. It wasn't up for a vote initially, and there was an alder who spoke out and said it was unfortunate that they had a small package with technical changes but couldn't include duplexes. Then there was an election, two or three seats changed, and in June it passed unanimously — which is remarkable. Part of that was having 50 people show up or write in to support the legislation. Ten of us said, "Please do this. We want this." No one spoke in opposition. There was no one registered in opposition.
Those are the kinds of changes we pushed through, building an environment of "let's try this, let's get to yes on these incremental changes." I think as a result of that, Madison is a great candidate to be the Strongest Town.
Thank you, Josh. Thank you for sharing that. In closing, tell us a little bit about your neighborhood or your city. What are some local businesses you'd recommend people check out to get a slice of local life? You can take this wherever you'd like — bookstores, pubs, restaurants, bike trails, whatever.
On Willy Street, there is a restaurant called A Han that is incredible. Every dish has always delighted me. That's Laotian-Vietnamese fusion, and it's really, really good. They also opened a new bar across the street, because their lines can get long and there are no reservations — so they created a place where you can hang out while you're waiting.
I also love the Vilas neighborhood, right off of Regent Street. Those are the kinds of businesses we're trying to persuade to be open to less parking, but it's a cool area to explore if you're ever going to a Wisconsin football or volleyball game.
I'll give a shout-out to T-Sider on Johnson Street, and to the Henny Lapham neighborhood in general. We did a missing middle housing tour there — basically walking through how so many middle housing options exist in that neighborhood but not elsewhere in Madison, and how they blend into the environment. There's also a hidden tennis court: there's a utility building you'd walk right past, but if you go up some stairs, there it is.
If you're ever in Madison and have a little time, the Lake Loop around Lake Monona is an awesome experience.
Amazing list. Thank you, Josh. This was a lot of fun. I loved hearing your stories and the progress you and your group have made as a local conversation group. Best of luck to your town in the Strongest Town contest. Thanks again for taking the time to share your experience with me and with our audience.
Thanks for having me. I really appreciate it. Please vote — and even if you don't vote for Madison, please vote. But really, vote for Madison.
We will definitely be putting links to the Strongest Town contest and to lots of things that Josh shared in the show notes. Thank you so much for tuning in for another conversation. I'll be back soon with another guest. If there's someone in your town who you think we should have on the show, please let us know using the suggested guest form — it's how we learn about lots of wonderful people doing great work, including Josh. I always appreciate it when you take the time to tell us about someone you think I should interview. Until then, keep doing what you can to build a strong town.
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