The Bottom-Up Revolution
A traffic jam in a video game changed how Bryan Kelly saw his city. He traces the path from playing City Skylines and watching Not Just Bikes to noticing stroads, long waits at traffic lights, and people biking on sidewalks along Sheboygan’s Eighth Street. That shift pulled him into a Strong Towns book club in a local coffee shop, Critical Mass rides with neighbors, and quiet committee rooms where he was sometimes the only person at the microphone. When a council seat opened, he carried those lived observations into a campaign centered on safer streets and fiscally careful projects.
Transcript (Lightly edited for readability)
Hi everybody. Welcome to another episode of the Bottom-Up Revolution podcast. I'm your host, Tiffany Owens Reed.
One of the things I love about hosting this show is that I get to hear the story of how ordinary citizens become involved in their city — how they come to care about their city, how they come to notice issues in their city, and how they come to be involved in the conversations around making their city a stronger, more resilient, more beautiful place. I really enjoy hearing their stories of civic engagement and how it all came about, because in most cases these people are not waking up thinking, "Today I'm going to become an engaged citizen." In many cases they have normal day jobs, they're raising families, but they just start to notice, then they start to take small actions, and the next thing they know they're leading a Strong Towns group or advocating for some type of improvement in their community.
In some cases they decide to run for office, which is not necessarily something we try to encourage people to do at Strong Towns. But it's always exciting when an individual's personal journey leads them in that direction. I always enjoy hearing what that journey is like, because I think it's interesting to think about the tension between advocating for your city in a grassroots way and then stepping into a position of more power and influence — working to make your city better from a more official, governmental angle.
So today I'm joined by Bryan Kelly. He is one of the leaders of the Sheboygan Strong Towns local conversation group called Sheboygan Active Transportation. He's helped run their book club, he's been leading Critical Mass bike rides, he's become a regular face at City Hall, attending various committee meetings, and he's been bringing Strong Towns ideas to Sheboygan by speaking up on topics of street safety and housing. He'll be doing all of that and more — much more regularly — as a newly elected member of Sheboygan's Common Council. Common Council is another way of saying City Council; I'm sure he'll explain that for us. Bryan, welcome to the Bottom-Up Revolution podcast.
Hi, thanks so much for having me.
It's great to have you here. Tell us a little bit about your backstory. If you're not from Sheboygan, how did you come to call it home, and tell us a little bit about your city.
I grew up in Manitowoc, which is about 20 to 30 minutes north of here, but my parents, for as long as I can remember, have worked in Sheboygan. After I graduated college, I ended up getting a job here at an insurance company as a programmer, and then I finally moved here right after COVID, around 2021. I've been loving it ever since.
For folks who've never been, tell us a little bit about Sheboygan. What's it like? How would you describe it to someone who's never heard of it or never visited?
Sheboygan is sort of a smaller-sized city — about 50,000 people — and it's right on Lake Michigan. We have these beautiful beaches, and there's also a river that cuts through our downtown, so we've got a great row of waterfront restaurants and properties. On each side of the river there are pretty long beaches that are really well kept. I love that about Sheboygan. I go with my wife on walks down the beach, stop at a little ice cream shop, that kind of thing. I highly encourage anyone interested in stopping in Wisconsin to check out Sheboygan.
I've heard it's actually popular for surfing. Is that true?
Yeah, there's actually a reference to Sheboygan in the movie Surf's Up. The character Chicken Joe is based on an actual person in Sheboygan who's been a huge part of the surfing scene here. To me it sounds a little crazy, because the best time to surf in Sheboygan is when it's freezing weather. They all bundle up in wetsuits, go out surfing, and there's ice forming on them and everything.
Funny you mention that. Sheboygan and Waco, where I'm based, might have something in common — Waco is also a surprising surfing destination, which continually blows my mind. We have no natural surfable water here; it's Texas. But there's this man-made place where they make mechanical waves, and apparently surfers love to come. I've never been, but that's our little pin on the surfing map.
So let's talk about Strong Towns. Tell us a story. How did you discover Strong Towns? How did you become inspired to participate in these conversations and eventually become part of leading the group?
It's kind of a funny story. I wasn't a really political person at all after college. What really triggered my interest was a game called Cities: Skylines that I was playing — basically a city builder, kind of like Sim City. One of the issues I was having was that traffic was a problem in my virtual city. I started looking up how to fix it, and I came across the YouTube channel Not Just Bikes. He did an episode on Strong Towns, so I started getting into Strong Towns content, and that led me to a local conversation here. I saw they were covering the Strong Towns books, so I showed up to the book club and just started getting more and more involved from there.
One thing the book club was curious about was what was going on at City Hall. So I just started attending some meetings, reporting back, and kind of became a staple at City Hall.
Literally now you'll be there all the time. Sometimes I feel like I should have a point system — if people mention Not Just Bikes or Sim City, you get a point. You'd get a couple of points, because you've got both of those in your origin story. What surprised you when you started reading Strong Towns and going to these meetings? What were you starting to notice about your city that you hadn't noticed before?
I really connected with the Confessions of a Recovering Engineer book. The two things that just stand out — and I can't unsee them now — are stroads and traffic lights creating traffic and the frustration they cause. Part of me almost wishes I hadn't read it, because now I notice it every single day.
Welcome to the club. There's no going back!
Exactly. Confessions of a Recovering Engineer really stood out to me, and ever since then I've been trying to advocate in little ways that we can improve our streets around town.
Your Strong Towns group is called Sheboygan Active Transportation. Can you tell us a little bit about why the focus on transportation and the name? I've never been to Sheboygan, but from the way it's been described and from pictures I've seen, it seems like such a cute little town. It doesn't seem like the type of place where transportation issues would be top of mind. What were you all seeing that made you say, "If we're going to put our energy into something, let's focus on active transportation — improving bikeability and walkability"?
I'm a current leader of the group, but I'm not a founding member. It was actually Heather, Cleveland, Kate, and Braden who formed the group. Their concern was: where do we go in City Hall to talk about making sidewalks safer, crosswalks safer, bike lanes — things like that? And there was no such place. The original concept behind the name was to create this group and have it adopted as a formal committee within the city, as a dedicated place to discuss those issues. That ended up not panning out, so we just started doing our own thing: hosting Critical Mass bike rides, running a book club, and showing up to City Hall whenever street redesigns come up to advocate for making things a little more bikeable and walkable.
Waco is notorious for missing sidewalks and curbs without ramps. When I talk to my friends who live here, sidewalks are always top of mind. What were you noticing in Sheboygan around walkability and safety — what specific details were you seeing that showed room for improvement?
There are two stroads that are really the key issues if you're trying to get from the south side to the north side, or from the lake to the west side of town. Eighth Street is our main downtown road — it's a four-lane street where people love to go fast because it feels wide open. That's probably our key one that we'd like to see made safer. I'm always seeing people biking there, and unfortunately a lot of them take to the sidewalk because they don't feel comfortable in the road. I'll be honest: I've had several near-misses there myself.
Then there's 14th Street, just a few blocks further from the lake. That's the one where you really do not want to be. If you look at a crash map of where pedestrians are hit, it's just lit up in red. It really acts like a moat disconnecting the east and west sides of town. It's difficult to address because it's classified as a highway, so the city doesn't have full jurisdiction over it.
Those are the two big challenges facing Sheboygan. We have been building some off-street bike lanes, which has been great, running parallel to some of these corridors. The issue right now is just connecting those. I think that's mainly a budgeting issue — you can't build everything at once. But over time we're making progress on connecting those off-street bike paths.
It sounds like there's real interest and demand for walking and biking in Sheboygan, which makes sense given how pleasant it sounds. But it also sounds like the infrastructure, as in most cities, is heavily oriented around cars — the assumption that driving is the best and only way to get around. Do you know anything about the history of Sheboygan and when that shift happened? I know it's a bit of a curveball history question, but for such a cute little town, you'd think it would be naturally walkable. Yet there seems to be a heavy emphasis on four lanes and cars for such a small place.
I think we've been making a lot of progress. I saw recently that somebody posted a historic picture of Eighth Street downtown, and it was significantly worse — just gas station after gas station, auto repair shop after auto repair shop. Now you don't see as many gas stations in the core of downtown. We have trees planted, which makes it look a lot nicer. So we are making some progress.
At one point, our Eighth Street downtown was completely pedestrianized, trying to create a kind of downtown mall concept. Unfortunately — and this was before my time — that drove a lot of frustration. People now kind of refer to that era as "remember when they shut down the street? That was horrible." But then a few people I'll talk to here and there will say, "Oh, I remember when I could walk down the street and it was so nice — I could sit outside, have my lunch, read a book, it was so quiet."
I'd bet that mall experiment happened in the '70s, because that was happening in downtowns across the US at the same time. I've read a paper about why it didn't work; there are various reasons. The same thing happened in Waco — they shut down Austin Avenue downtown and it completely bombed. Now when you bring up the idea of having one walkable street downtown, everyone recoils, even if they didn't firsthand experience it. It's oddly baked into the psyche of the city. It's really interesting how stories carry power like that and shape our perception of what's possible.
I'd like to go back to the Strong Towns group. Tell me more — you mentioned the book clubs, Critical Mass bike rides, attending meetings. What surprised you when you started going to City Hall? How were you putting the pieces together between the Strong Towns meetings and seeing how decisions actually get made there?
Sheboygan being on the smaller side, I was really shocked at how little conversation there was in City Hall. I would go to these meetings, and a lot of times I would be the only person from the public. They'd be like, "Okay, it's time for public comment," and they'd just look at me. Sometimes I wouldn't have anything to say, so it got a little awkward. Most of the time it was just going through the agenda items: motion to approve, approve, second — that kind of thing.
Speaking out felt very intimidating, because it's not really a venue where you can ask questions. It's more: say your prepared statement at the beginning, before you know anything beyond what you could prepare in advance, and that's it. In the book clubs and our local conversation, everything is conversational — we bounce ideas off each other and improve as we go. City Hall is just: you show up, the members give a yes or no vote, and only the people on the committee are really allowed to talk. That's kind of why I ran — if nobody else was going to ask questions during these meetings, I would love to be that person.
We'll come back to your decision to run. But first, can you share a little more about what the local conversation group has been working on — maybe some wins you're really proud of and what you've been able to accomplish in Sheboygan?
Our group has been around for a while. One of the founding members, Kate, runs a coffee shop, and right outside she partnered with an Ale House called Eighth Street Ale House. Around COVID, they were talking about getting a little beer garden — shut down the street and just use that as their area. Because of COVID, the city allowed it to happen. That spot is probably my favorite in town.
Beyond that, we've just been growing slowly as a group. Over time we've had more and more attendance at our book club. Our Critical Mass bike rides have been building up — we're probably seeing 50 to 60 people show up. Our goal, and we've been joking about it, is to get 1% of Sheboygan to show up, which would be about 500 people.
The city has actually started to partner with us recently, which has been really encouraging. There was the comprehensive plan that started, and the mayor reached out and said he'd love to do a bike ride and asked if we could help host it. We did that about two years ago. Now the city is working on a Safe Streets for All grant program, and one part of that is a demo project — tactical urbanism type stuff. There's an ice cream shop near downtown where people are always crossing a pretty wide street near some parking. We're going to try, just with plastic posts and some paint, to daylight that intersection a bit and make it easier to cross.
You mentioned the city is starting to partner with you all. That's a big deal. You were a contestant in the Strong Towns competition, and one of the things we talked about was having a bit of a headwind when it came to getting the city to embrace a more tactical, incremental, experimental approach. Can you share what it's been like trying to build relationships and have conversations with city staff and city leaders — saying, "Hey, we've got these ideas, let's try this experiment, maybe we can slow cars down here"? Some cities are very receptive and some have more hesitation. It sounds like Sheboygan fits more in the second camp. Can you talk about how you've been able to navigate that and help them ease into embracing this tactical approach?
We haven't really done anything where we're going against the grain. We've been really trying to work with the city. What has helped us most is just showing up, being here for years. We've become that familiar face — if there's something we love, we advocate for it, support it, share it on social media. If there's something we're not a fan of, we speak out against it.
Just being there, being that familiar face, and developing relationships with actual city staff has been huge. Now that we're starting to work with the city a little bit, that door is slowly opening. We're starting to get city staff a little more on board with experimenting, rather than having huge plans that take years to develop. I'm really excited about this grant program demo project. I'm hoping it's a way to get our foot in the door to do more of this throughout the city.
You all have had a success with the parklet that you featured in your Strong Towns nomination. Can you tell us about it?
The parklet is right outside that coffee shop, and about a block over is where the farmers market is. When I got out of college, one of the things I was missing was that feeling of going to one spot and bumping into all your friends — chance encounters. That's really what the parklet has become for Sheboygan. On a Saturday you can go to the farmers market, eat, stop at the parklet, eat what you've bought, and you'll just start bumping into people and friends throughout the day. It's been awesome for connecting the community in a more casual way, rather than having to go to a planned event.
I think it'd be cool to hear a little more about how you all negotiated with the city on that, because it involved a street closure, right? I think it's a really good example of a win that the city can look at and say, "Wait a second — this is working. Maybe this idea of experimenting with tactical urbanism isn't so crazy after all."
It was a difficult project and I think it's still continuing to be a little difficult, because the city is structured in a very top-down way — people in positions of power making the big decisions. What really opened the door for the parklet was COVID. I think that's pretty common throughout America — COVID triggered a kind of experimentation: "How can we get people connecting while still being outside?" I think that's really what allowed the city to let the parklet happen.
Since then we've been trying to improve it incrementally, making little improvements around the edges. I'm not sure I see other big projects like closing down a street in our near future. But the parklet has really become that great community anchor downtown.
Let's talk about running for Common Council. Can you share the aha moment when you realized, "Hey, I can do this — this could be a way I could really be part of the conversation in a different way"?
It really came down to the group wanting to know what conversations were happening in City Hall. So I started attending, and over the course of two or three years I've probably gone to hundreds of meetings. Through that I've just learned so much — here's what the Water Works Department needs for sewers, here are all the considerations for road maintenance, and so on. I've just been absorbing information and commenting where I can.
Then I found out that the alder of my district wasn't going to seek reelection. I thought, "Okay, this seems like a perfect time to try to get a little more involved — I can try running." That process was not something I had ever expected to go into, but I was really shocked at how much support people showed. People would reach out and say, "Hey, I'm really happy you're running. I really like your stance on safe streets." It's been kind of a whirlwind, and I managed to make it.
Congratulations on winning! What did you run on? What was your platform — what were some of your talking points?
I was really trying to tie in as much of the Strong Towns lessons I've learned through the book club as possible. My big focus was making our streets safer. One thing I really want to bring to Sheboygan is the crash analysis studio type of thinking: if there's a bad crash, we should get together with the city and neighbors to improve that spot quickly, then ease into a larger improvement. That really connected with a lot of people — it's one of those things where people say, "Yeah, why aren't we already doing that?"
I also went through the last 15 years of financial reports the city was putting out using the Strong Towns financial decoder. I would talk about that at a high level, trying to help people understand where our finances stand — that we're going a little more into debt, we're not as bad as some cities facing insolvency, but we should be careful and make sure that the projects we're doing are more financially productive than the maintenance costs we're taking on. Those were really my two big talking points on the campaign trail.
I've never run for city council, but from conversations I've had with people who have, one of the key characteristics of serving in a role like that is being able to coordinate across a variety of priorities, assumptions, and frameworks for what a city is, how you improve it, and what good change looks like. How are you thinking about that as you step into this role? It's not like you're going to be given a magic wand — no more stroads, more bike lanes. How are you thinking about having a vision for what a place could be while navigating compromises and helping people see how moving in a particular direction is better in the long run?
Sheboygan being on the smaller side, our alders are not full-time — it's a part-time position. There aren't a lot of seasoned politicians on our Common Council; it's regular people just trying to help out their community. That was the environment I was stepping into.
The big thing has really just been trying to talk to people. I was honestly surprised at how much people share the same values once you start talking with them. It's really just about framing conversations well. I'm for safer streets, and people might think that means you're into big spending. But there are ways to make streets safer without spending a ton of money or raising taxes. Going through the Strong Towns books and similar reading has been vital for me in terms of giving me the content background to have informed conversations with my neighbors.
I like that — thinking of everyone you're serving with as your neighbor. We can probably talk through this over a cup of coffee with some good conversation and find where we have common ground and common vision.
When you put your head on the pillow at night and think, "I just want Sheboygan to be a strong town," what specific things come to mind? What's your vision for your city becoming a stronger place?
In terms of what you can do as an elected official, I'm really excited that the city is finally taking on its zoning code. As advocates we've been pushing aspects of the Housing Ready Toolkit, and I think that's been a great tool for introducing policies we like and explaining why they matter. We've managed to get our zoning code to add parking maximums, which is new. Previously we had pretty high parking minimums; we're reducing those and adding parking maximums. We're also reducing lot sizes and legalizing ADUs and townhomes. We're making real progress and I'm excited about that.
Beyond that, I think having a thoughtful approach to street construction — so that when we're redoing a street we ask whether we can add improvements to make it safer for people, like a bumpout at a crosswalk — is really important. Those two things are what I'm most excited about: working on housing and advancing street safety. We're making some baby steps, and I'm hopeful that as these programs go well, we can keep making more progress.
One thing that stands out to me from talking with you is how you're able to see the value of conversations, not just outcomes. A lot of people thinking about running for public office get excited about achieving a specific outcome. But from hearing you talk, it's clear you would love those outcomes, and you also see the deep value of talking to people, building relationships, and having conversations — even if they don't lead to the exact outcome you're going for. Does that sound right?
Yeah, definitely. It's really come from being in these meetings and being involved for a few years. Honestly, it was pretty defeating early on. I would speak up about something I really cared about, and at one committee meeting the chair of the committee said, "Well, what input could you possibly have on streets?" I went through and said, "Hey, people might use this street to get to school," things like that. Before that, their main focus was purely traffic throughput. I thought that was sort of eye-opening for him.
Then I actually saw him later as a citizen, showing up to a school meeting and giving his opinion on whether they should tear down the school and move it to the edge of town. Seeing somebody who had basically said "why would you even show up to this kind of thing?" suddenly showing up to different events and giving his input — that was really encouraging. It was kind of disappointing at first, but after just sticking with it for a few years, you've got to take those little wins as they come.
There's so much value in presenting a different perspective, even if you're not getting the immediate outcome you're going for. That's a really helpful way to think about serving in public office from a Strong Towns perspective — anything you can do to advance your city toward a more resilient future, but also don't underestimate the power of all the conversations you're going to have and the ways you might be changing people's minds.
Bryan, this has been really great. I'm so glad you came on to share your story. In closing, I would love it if you could brag a little bit about your town. Tell us a couple of businesses you'd love to recommend if people come through to visit.
All right, so I was thinking about this a little bit. It's really hard not to just list all my favorite restaurants.
That's always the one everyone has to think about the most!
If somebody is going to visit Sheboygan, start with the beaches and head downtown — there's so much for everyone. There's a board game shop that has just a great vibe. A little further down, definitely visit the parklet and Paradigm, the coffee shop that Kate runs. There are quite a few great places to eat on the river. We also have a small brewery called Three Sheeps that's fantastic. Focus on downtown, head out to Three Sheeps, and personally, since I love biking, we have a mountain biking trail system in Evergreen Park — check that out. There's a lot downtown, honestly.
Oh, and we're also known for food: Johnsonville is one of the big factories here, so brats are huge, and Sheboygan hard rolls are huge. Have a brat on a Sheboygan hard roll — it'll change your life. There are also a couple of chefs who own multiple restaurants. There's Stefano, who has a pizza shop, a higher-end Italian place, and a brunch spot, all on the same block. There's Harry's Diner — a great breakfast place with a classic '60s steel-and-chrome building, and he also has a spot right on the river where it's more Italian dining. In the summer you can sit on the river, have a nice little meal, and listen to the seagulls.
Oh, and I was going to say — charter fishing is huge in Sheboygan. If you love fishing, there are so many different charters. Getting out on the lake is just incredible. I actually learned how to sail recently, which was a lot of fun.
I love being on water. We have some water here in Waco, but in my heart I'm definitely more of a coastal person — ideally the East Coast. You did a really excellent job bragging on your town, so if you were stressed about that question, you nailed it: 10 out of 10. Bryan, thank you. Thanks for coming on the show and sharing your story. It'll be exciting to maybe one day hear what this experience has been like as you step into this new role.
Thank you so much for having me. Hopefully I'll meet some people at the national gathering — I'm planning on going this year.
Amazing! To our audience, thank you for joining me for another conversation. I'll be back soon with another episode. If there's someone in your community who you think we should have on the show, please nominate them using the suggested guest form in our show notes — we always really appreciate reading the nominations; that's how we find out about a lot of our guests. In the meantime, keep doing what you can to build a strong town.
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.