The Bottom-Up Revolution
What does it look like to actively love the place you live? Tiffany Owens Reed talks with New Haven Alder Caroline Tanbee Smith about community-building, public space, and how small, people-powered projects grow into lasting civic impact.
Transcript (Lightly edited for readability)
Hi everybody. Welcome to another episode of the Bottom Up Revolution podcast. I'm your host, Tiffany Owens. It's a delight to be bringing you another conversation on this Monday morning.
I know that for some people involved in the Strong Towns conversation, it might sometimes be a little bit confusing thinking about, "How do I get started? I want to do something for my community, but I'm not sure where to start." That's why this show is here. I've been hosting the show for about two and a half years, and I just want to say, I really hope maybe as you're winding down for the holidays or going into the new year, maybe take some time to go through our archive and listen to some of the older conversations. We bring such a wide variety of people onto the show—people who are just doing everything from raising children and doing work to help their community in their downtime, to people who are running for office or people who are serving in public office.
I am delighted to be bringing you one such story like that today. Caroline Tanbee Smith serves on the City of New Haven Board of Alders in New Haven, Connecticut. Outside of this role, she is a growth and innovation director at the Friends Center for Children, working at the intersection of child care, housing, and education. Prior to working at the Friends Center, she was the co-founder and co-director of Collab, a community accelerator supporting early stage entrepreneurs in Greater New Haven.
She's received the Yale Jefferson Award for Public Service, Connecticut Magazine's 40 Under 40, and one of the New Haven Independent's Under 30 New Haveners of the Year. I hope I said that right. As well, she was also selected to be an inaugural Redwood Fellow, which I think she'll tell us a little bit more about—a lot of really impressive things in this introduction. So she graduated Yale in 2014 and Yale School of Management in 2025.
But more than that, I've had a chance to talk to Caroline. She loves her city, and I hope that's what you take away from this conversation—not that in order to really fix your city, you need to run for public office and that's the only thing to do that really matters. But the most important thing is to love your city and figure out what's the best way that you can use your unique gifts and talents to make it a more resilient, more beautiful place.
Caroline, we have a lot to talk about, and I know it's going to be a great conversation. Welcome to the Bottom Up Revolution podcast.
Thank you, Tiffany. It's great to be here. Appreciate you.
So I have to admit that—I'm sorry, we had an intro chat, and I never even asked you what you do for work because it seemed like you're just so passionate about being an alder that's literally all you do now. Reading your bio, I realized I was wrong. You do many things, including working at Friends Center for Children, and it seems like you just keep yourself really busy trying to do the best you can to solve problems for people in a good way.
So let's just jump in a little bit with your story. You grew up in Kentucky but moved to New Haven when you were 17, if I recall correctly, and you've remained there ever since. Tell me about New Haven. What makes it feel like home to you? And maybe you can tell us a little bit about your journey there.
Such a beautiful question, Tiffany. Again, it's great to be here, and congrats on two and a half years. I am a huge fan of Strong Towns and have had the privilege to listen to this podcast a number of times on a run or on a walk. So just congrats on the number of podcasts you've had and the number of interviews you've had. It's a true resource for so many people who love their city.
I think you're really right that I can predict over the next hour the theme will be love of place. I think that's the best way to answer the question you just asked, which is, I would say, if my life so far has a thesis statement or a spine, it's about love of place.
As you said, I grew up in Kentucky and then took the long plane ride to come over to New Haven, Connecticut when I was 17 years old to attend school at Yale. I just completely fell in love with New Haven, the greatest small city in America. I spent most of my summers here. When I was in school, I had the privilege to intern for the mayor's office, where one of my projects was to create a residence guide to the city, which took me to dusty corners of city hall and City Plan department and across multiple neighborhoods. That sounds like the dream summer assignment. It was.
My other project was to help to run the Democracy School program, which brought a lot of neighbors together who were interested in learning more about city hall and how it worked. So yes, it was a dreamy summer, and I got to just have these spectacular moments of love of place—everything from spending the summer seeing Yo-Yo Ma on The Green with 8,000 other New Haven residents in the pouring rain. Those kinds of memories just linger with you forever. Also seeing really powerful actions take place.
My belief in New Haven is really derived by the spirit of advocacy, the history, the entrepreneurial spirit of the city that you can just feel rippling through the sidewalks and streets. I think, as a young person at the time, I was so moved by that experience and also built so many friendships that made me say, "Hey, I want to fight for this place too," just like these mentors and coaches I see around me who are fighting for this city.
Also, I think my love of New Haven is derived by just the smallest of interactions. I remember going for a run and seeing a neighbor on their porch and waving to them, and then going for a run the next day and seeing that same neighbor. I think that that feeling of the building of relationships over the course of time was very moving for me, and it continues to be moving for me today.
Even thinking about that role at the mayor's office—for example, my boss at the time was Becky Bombero, who currently still works in the city. Just two nights ago, I was in a Board of Alders meeting where she presented an item. To think that 15 years later, we're still able to work together—that's the power of a city, is those kinds of relationships that can accumulate and build over the course of time. I think if magic exists, it's that feeling.
I think the power of a city and a power of a community is that it's just small enough where you have those moments of building of relationships over the course of time far more readily. So I just fell in love with the city, and now I've been here for 16 years, over half my life, and just want to keep fighting for it.
It's really neat listening to you explain that, because I grew up moving all over, and I think maybe you can relate to this in a way. But so I didn't really have a place that was just—I was born into, and then was, "Oh, this is just where I'm from, this is just my story. I'm from here. My family's from here." I don't have deep roots anywhere, so I'm always thinking about the interesting puzzle of what makes a place feel like home.
I think it can be different things for different people, but when you were talking about the memory of listening to that performance in the rain, it reminded me of going to an orchestral performance in Chicago randomly. I was in Chicago for a weekend, and they had one of those free open air performances for a youth orchestra or something. I'm pretty sure it was rainy, and I just wonder sometimes—I have this theory of, what are the things that make people just bond in a weird way to a place?
I think what you said about positive experiences with strangers in public places, like listening to that music, but also the weird curveball that weather can throw—New Yorkers are really good at this. They'll go through the most ridiculous stuff and ridiculous weather, but it has to be a bunch of strangers in a safe place, in a public space, designed for that. There's just something oddly magical about it.
I think the other thing you said about having those positive but brief encounters with strangers—I just think there's something to this. I think this is where the money is, because I think even if we had the ideal village where you're surrounded by—if you could convince all of your friends to move to the same neighborhood, it wouldn't be the same. It wouldn't be the same as a neighbor saying hello, seeing the same neighbor, seeing the same people who you're not bonded to, except for this sort of loose tie kind of way.
I don't think you could be happier without that. I don't think it would make a place happier. Even if you had all of your favorite people in the same neighborhood, I would still bet money that it's going to feel more magical when you also have strangers, that you have those brief, positive interactions that are part of just everyday life—the saying hello on the run, or the barista who knows you by name, or the random shoe repair man who you can leave keys with. Those kinds of moments. I think you're onto something with that story.
I think it's so beautifully said. In many ways, I think about—I'm curious if this resonates with you—part of my life's work, and in some ways, kind of what I hope to give back is the thing that life has given me.
New Haven—I wasn't born here. I was born in Kentucky, but it's the city that really took me under its wing. The gift it's given me is purpose, is meaning, and is love—love among neighbors. I think we, and we'll get into this in our conversation, but we have so many tools at a local level to create the conditions for those magical moments, whether it's everything as spectacular as the one that sounds like you and I both shared of listening to music in the rain.
I do think maybe there is something a little bit magic about rain and music specifically together and community. Maybe there's a policy that can help to create the conditions for that trifecta to happen. I think it's really interesting.
Well, I think it's one of the things that just happens naturally if everything is done right. That's right. I feel like I've seen other things happening in there. I saw something recently—I mean, people will go do races in the rain, farmers markets, no matter the weather.
I don't think it's the type of thing you'd have to policy out. I think if you just engineer the public environment right, and people see other people doing it and it looks safe and kind of fun, I think people want more unpredictable experiences in the city. I was thinking about this this morning, where I was, "Why do I get so bored sometimes?" I was, "Oh, it's because I don't have the adrenaline rush of having to hurry up and catch the bus or hurry up and catch the subway, or just never really know what's going to happen when you get off the subway."
Hopefully nothing terrible, but just that adventure. I think sometimes the way our cities are designed kind of takes adventure out of it. It's, "Just get in your car and it's super predictable, and you drive the same route to the same place, to the same stoplights, and there's just nothing that can surprise you." I think people like surprises. I think as long as you have the right gear and you see other people having a relatively good time in bad weather, I think there's something about that—we're actually drawn to it because of the adventure of it all.
A thought and a question for you. One is that I love this frame of, how do we create the conditions in a city for unexpected delight? I think that's just a fantastic frame. I think if we were led by that as a horizon line, I wonder how it would change some of our decisions.
And then two, when was the last time you experienced that, whether in the city that you live right now, or in another city, that kind of moment of unexpected delight of place?
Oh, boy. See, I've warned every guest when they come on the show that I might ask you a question that's not on the script, and now it's getting served back to me.
I mean, I was in Charleston last summer—yeah, summer of this year—for doing some work. It's the last place I was moving around on foot. I don't move around on foot in Waco that much, unfortunately. Also, I have two small children, so normally if I'm in Waco, it would probably be on my bike, but I can't really do that right now. So I'm gonna go with Charleston, because it's the last time that I was roaming around a city without children on foot.
I would say I ended up renting a bike there. Oh, I will tell you the answer to this question. I kind of have two answers. One, I was very pregnant during this trip, and Charleston is very hot, but it's also just loaded with people. There's just people. It's just super walkable. People are getting around on foot. There's tons of tourists there, and it's beautiful. The architecture—I don't know if you've ever been, but the architecture is just stunning. It's old, it's beautiful. It's everything I love—beautiful colors. It's aged. It's just really got the soul.
I found myself wanting to get pictures and be around the city with some of these really beautiful backgrounds, but I was by myself. So I ended up running from spot to spot to spot, ripping my shoes off to stand barefoot at these pretty spots and propping my camera up and doing basically my own solo maternity shoot. But at some point I would literally just grab a stranger and just be, "Can you take this picture for me?" They just—it was usually women, and they immediately knew what was happening. They're, "Oh my God, I'll take that phone." They were so excited.
I was, "I think I should—I don't know, I'm not gonna get pregnant every year, but there was just something about—everyone just knew. They were, 'You're about to have a baby. It's a beautiful city. You don't have to explain anything. Just go run over there.'" It was really fun. I think that was a really fun experience.
Also, I rented a bike and got around Charleston by bike, which was so fun just exploring. But then there was this other evening where I wanted to walk to a grocery store from the hostel I was staying at, and I had to walk, and it was kind of getting dark. Just watching the built environment totally change—you could see I'm leaving the historic district, and I was going into a more poor part of town that was really close to a highway. You could tell it was in that tense place of being developed, and sort of just feeling it. I could feel it in my body with the weird development decisions that have been made about where things go, and the neighborhoods that were awkwardly situated between a highway and new development. You could just feel it in the air. There was not much to do. It was getting dark and I needed to get back.
But just was a good reminder of what happens when you're out of a car and you're moving around in an unpredictable way, moving around a place. You can sort of see the layers of the story, and you can sort of see and almost even feel the tension of what's happening, or just the uncertainty around what's happening as well.
But yes, recruiting strangers to help me take my maternity photos was definitely serendipitous and just really fun memory.
I think that's such a good memory. I know we'll talk about this a little bit more later, because in the first conversation we had, we talked a lot about our shared care for how do we invest in our social and civic fabric so that more neighbors come together and feel connected to each other and know each other.
One of my reflections after that conversation was this idea of something that I feel like I do is try to tap people. So if there's a project that we're working on, I talk to someone that they care a lot deeply about traffic safety, how do I tap that person, or bring that neighbor in to be a part of the leadership of that effort? The question I had, though, is, what does it look like to do that at scale? How do we tap people at scale?
In some ways, I think your version of tapping someone, tapping a stranger to say, "Hey, help me take a picture," was tapping them into an experience that they—I wouldn't be surprised if it kind of lingers with them throughout the day, because it made them smile. They were able to do something for someone else.
So what does that look like at scale, whether tapping a neighbor to be involved in a project and really sink their hands into the soil of actually getting something done, or tapping someone to just do a more act of kindness? How do we tap people more and what does that look like on a sort of system wide level is something that I'm really curious about.
I think part of the answer might be found in the story of one of the guests I just had on the show. I think it was Victoria Via out of Portland, Oregon. She's helping lead a Strong Towns group there. I don't know if you know a lot about how our local conversation groups work, but everyone is very different. We have hundreds all over the country, and they're all so different. There's not one formula for how to start a conversation group.
One thing that they did is they really took a super neighborhood approach to starting the advocacy or improving things. So they have sort of this crabgrass network of just neighborhoods that are solving issues on a neighborhood level. I feel like that might be key to answering your question of, if you think about your city, and you break it up into neighborhoods, and you can break those neighborhoods up even smaller—because it's hard, I think it's hard for people to have a sense of connection if it's all sprawl, if it's all just randomly connected to, "I know these people because we're all interested in this thing, but we don't really share that much proximity, literal physical proximity or a shared piece of land at all."
But I think if you could take a neighborhood approach to it, where you have strangers that are connected by proximity—they actually live on the same block or in the same collection of blocks—and if you're able to channel that energy into really a neighborhood-based sense of care and stewardship and action, I think that's probably the closest proxy to what you're talking about, of that tap effect. Because those people more likely know each other, since they're in the same neighborhood, and the energy doesn't have to spread as far if it's contained in the neighborhood.
Yeah, so listening to Victoria talk about how they were able to—they didn't even sit down and say, "This is going to be our amazing plan." It just sort of emerged organically that taking a neighborhood approach, a neighborhood-based approach, to starting this local conversation group, it just kind of happened. I think there's a lot of wisdom in that.
I can't remember. I felt like I had another way of answering that, but I actually can't remember. Maybe it'll come back to me in a minute. But yeah, I think you're right that the changes we want to see in our community—and not even changes, it's more just energy and presence and a sort of—I don't know, I guess the young people these days would call it vibe, you know, what you're looking for.
I think I mean, you can't get around the fact that it really does take people actually seeing each other. It's funny, because this is such a basic, basic element of what it means for a place to be a place is that you should be able to see other people. So I think one of the biggest challenges of our neighborhoods and of our cities is, well, how do we make each other more visible?
That goes back to the built environment, and that goes back to issues around mobility. Well, if everyone's in a house, in a car, not on the street, there's one of your biggest challenges right there. How do you create a sense of fellowship or neighborliness if you literally can't see other people?
So I think making people visible again is a huge part of that challenge. Then I think scaling it by neighborhood, rather than thinking about the whole city—that's what I would bet my money on. But I don't know. I feel like you are probably a better person to answer this question, because you've actually been in the trenches doing work kind of in this vein.
As I mentioned in your bio, before you're even serving in public office, you've been trying to figure out answers to this question for a long time, and it's looked a lot of different ways for you. Specifically, I was curious if you could share with us about Collab. So that's the nonprofit I mentioned, and I know from our conversation that Collab is a nonprofit dedicated to simplifying the startup process for small business owners. Can you share about that venture and maybe the story behind it and what you all have been able to accomplish?
Absolutely. So we started Collab back in 2017, and the real heart of it is that New Haven's really a city of entrepreneurs. It has been, and I believe it always will be. I think New Haven really punches above its weight in terms of individuals who want to build a business or build an organization that makes impact on their family, themselves, and their neighborhoods.
One way of defining entrepreneurship—one way that Collab defined entrepreneurship—was an individual who takes a risk on behalf of their community. Ultimately, I think for so many entrepreneurs, at this point, through Collab I've talked to hundreds, hundreds of entrepreneurs. Entrepreneurship can be, ultimately, a deep act of care from an individual to their community and to their neighborhood. I think that's tremendous.
So New Haven's a city of entrepreneurs. Something we noticed, though, was that even though there was no dearth of brilliance, no dearth of really great ideas, there was a gap for individuals to take that idea, take that idea for a food truck, a restaurant, a skate shop, a flower shop, and turn it into something real, something real that could impact themselves and their families and their communities.
So that's what Collab's mission is all about—creating the support infrastructure, a series of workshops, access to pro bono services like legal and accounting and marketing support to wrap around an entrepreneur so they can take that idea and really materialize it.
It was just such a privilege. I think, if anything, my belief in the possibility of New Haven was just deeply strengthened through the process of those five years of leading Collab, just witnessing entrepreneurs like Domingo Medina, who started Peels and Wheels Composting, a bicycle-powered composting service, or Havenly, an immigrant refugee-led cafe that's on Temple Street and it's activating Temple Street in downtown. Just witnessing these entrepreneurs taking a risk on behalf of our community was just such a tremendous experience.
So we led it for five years, and then passed the torch to new leadership, and then it's been merged with another organization called ReSet, kind of like our uncle nonprofit in Hartford and also in Connecticut. The vision now is for Collab and ReSet together in New Haven, Hartford, to create a more statewide approach to this heart-centered, really community-centered leadership.
It's really informed my work. I think just being able to have the privilege of sitting down with so many individuals who are trying to build something—I think that's what makes New Haven special. In my mind, again, I'm biased here, is I think New Haven's one of those cities where you can really build something, and you will have the community and the individuals around you who will help support you, to pressure test it, to see if it's possible, to take it to the next level, to see if you're right or wrong. I think that is an incredible part of what it means to be in the city.
You also started New Haven Bike Month. Can you share that as well? And yeah, just love to know a little bit more of the story about that.
Yes, yeah. I think I would say one way of thinking about kind of my work over the last few years is looking at our social safety net in the city of New Haven and having the privilege to be able to build organizations to be able to fill gaps in that social safety net. So Collab was one—entrepreneurship should be a pathway that's accessible to anyone who has an idea and has the will to try it out.
Then New Haven Bike Month—the core mission of Bike Month is to—it's a month-long celebration of biking culture that happens every May with the horizon line of the goal of ensuring that every single neighbor in every single neighborhood in our city can feel safe, excited, and empowered to ride their bikes.
So over the last 10 years, we just had our 10-year anniversary. Every May, we galvanize volunteers and individuals and event organizers to come up with a series of events all throughout May that are all around promoting and spreading the word around biking culture and also advocating for more significant biking infrastructure and more equitable transportation in the city. It's been incredible.
I would say two things. One is that, as a result, volunteers have fixed hundreds of bikes throughout the city, have been able to give away hundreds of bikes. Also, we've been able to do some pretty special events. My favorite one, my favorite event that we had during Bike Month was a few years in we hosted a wheelie competition. We had a lot of young people who were doing wheelies across the city, and we wanted to celebrate the work that they did. So we bought a couple trophies. We had the mayor at the time give away awards for the slowest wheelie as well as the longest wheelie, sort of safe wheelie competitions. I hope we can bring that back in the next few years. It was wonderful.
So, okay, I have two questions. One, how did biking land on your radar? Did you grow up biking a lot? Or, because I know the whole world of bike infrastructure and all of that in cities—how did you come across that and what resonated with you about that?
I mean, similar to love of New Haven, I think that it didn't start as sort of driven by advocacy or driven by even any of that sense of vision. It was just driven by delight and love. So I just loved biking when I was a kid. It was a way of building independence and building a sense of freedom, just biking around the neighborhood or being able to bike to the grocery store.
Then when I came to New Haven, it was my primary form of transportation, and I just loved it. I don't know, I don't love biking fast, but I love turns. I love just the feeling of—being on your bike, in my mind, is one of the most liberating and freeing feelings in the world. So it was driven initially by that just delight and excitement.
Then from there, as a bike rider, you begin to notice one, all the individuals and the energy that was in the city around biking. Part of the spirit of Bike Month has been to let's bring all that energy together around one month as a momentum builder.
Then the second thing, which is there's gaps. We have real gaps in our biking infrastructure. We have gaps in our transportation landscape. So can this month be also a momentum builder to begin to fill those gaps in a way that's joyful and in a way that's driven by the love for the city?
So my second question—you went to school. Oh, I know you have your MBA, so I'm not sure what your undergrad was in, but definitely I can see a strong emphasis in business. I'm curious, were there any experiences or—what helped you, sort of—what I'm trying to ask is, where did the civic angle come from?
Because a lot of people, they'll go get their MBA, or they'll study business, because they really want to start a business, and they like the challenge of that. They're interested in the business side. But I feel like everything I've heard about what you're doing is, "Well, I'm going to do this because it's a way to serve the community, or help the community, or do this for the community."
So I'm just curious, as you're looking back at your life, is there a moment or a story or a person where this sort of got really cemented in you of, "Well, this is a means to help this place thrive and flourish"? I don't know if that was before your MBA, or why you got your MBA, or after your MBA. I don't know, but how would you tell that story?
Yeah, I think what initially comes to mind is, I grew up playing sports, so I grew up playing basketball and running track. I think that ultimately, civics—there's a way of defining civics as being a part of something bigger than yourself. Playing sports growing up, that was the dominant way that I had that experience of beyond the self and what is possible when you have five young women on a basketball court and are trying to run a play. I got to experience that a number of different times as a young person.
Then when I came to New Haven, I got to feel that 100, 200 times fold by falling in love with the city and being as part of something bigger than myself in a city. Honestly, it took time, I think, for even the word "civic" at capital C civic to be the way that I thought about the work I did, because it was much more driven by, "I love my neighbor."
I remember spending a year working with high school students at New Haven Academy, high school students who I know still today, and working on their own projects, photography projects, things that they wanted to build. I was driven by love and care of those young people that I was stewarding and supporting and coaching.
I think over the course of time, I recognized that—the foundation of why we vote, the foundation of why we run for office, I believe, is it can be love. That love, at least for me, love and service are almost synonymous. But that's the ultimate foundation of a place. That's why I really care about investing in infrastructure, like supporting our small businesses and creating these opportunities to bring neighbors together, because it creates the conditions for us to fall a little bit more in love with each other.
I do think if we have that sense of bond and stake in one another, that's why we go out to vote. That's why we feel—hopefully again, that's what I would hope—that we create the conditions for that love, that love and that shared sense of stake to be what bonds us.
Well, let's talk a little bit more about the civic side then. So tell us about your journey to public office. Maybe you can start by telling about what an alder is—that might be a new word to some listeners. What is that role? What's entailed in that role? And then share your story about how you decided to run for office. How did that come about?
Yeah, so in the city of New Haven, we have a Board of Alders. It serves as our city council. It's our legislative body. There are 30 of us, 30 alders, which means it takes 16 votes to get something done. So there's a real emphasis on collaboration across wards. Every ward is around 4,000 to 5,000 people.
I would say the job description of an alder is three things. One is to be an advocate for your neighbors around constituent services—everything from potholes to fixing streets to bringing people together around projects. Two, is around citywide policy, including our budget, our most important values document as a city. Then lastly, is around the dissemination of information so that residents can advocate for themselves.
That's something that I've invested a lot of time into, whether it's social media or a weekly newsletter or regular letters or events to bring neighbors together. Because I think ultimately, part of our role is to provide clear and transparent information so that neighbors can be their own advocates.
My journey to running for the Board of Alders was a little bit long. If I'm honest, it took me some time, I think, because I remember just a couple years after I graduated, someone was stepping down from their role on the Board of Alders and said, "Hey, would you want to run for this?" I said no at the time. A few years later, a similar moment happened.
I think for me, the reason why I paused in those first years—one was because I had a high degree of respect for the responsibility of the role. I do believe that, at least for myself, I'd been in the city at the time five, six years. I think it takes time and understanding. There's a connection between a depth of understanding and deep authentic care for a place. I think what it looks like to really be able to serve a place—I think time made a difference.
Also, I wanted to be able to build a strong spine. I think one of the challenges of these kinds of roles is that sometimes it's tough. You have to say yes or no. Sometimes people get frustrated with you. I think for myself, I knew it was really important to me that I built a strong sense of character, a strong sense of my values, and a strong sense of who I am and who I want to be in this kind of role, such that I could approach decisions with hopefully a level of courage and also authentic to the person that I wanted to be. So that took me a little bit of time.
So after—I'm just now finishing my first term on the Board of Alders, and just ran for reelection and was really honored to be reelected. We'll be starting my second term in January.
What are some of the—well, tell us about your ward, number one, and then tell me a little bit about kind of how you are seeing your role as an alder, and maybe some of the things you're hoping to address, or some of the issues you're hoping to work with.
I love the ward that I represent. Ward 9 includes parts of two neighborhoods, East Rock and Fair Haven. They're two very different neighborhoods, very different and distinct, culturally vibrant, rich neighborhoods with a deep sense of history. I love being able to serve and represent two neighborhoods that are very different than each other.
I think in some ways, the fact that I serve these two neighborhoods has defined some of the priorities that I focused on in my role on the Board of Alders. So Ward 9 is divided. These East Rock and Fair Haven are divided from each other by I-91. In the mid-1900s during urban renewal, as you know, New Haven was called the Model City. It was a city that has been known for its role in urban renewal, known for being a leader in urban renewal, and known after that for being a city where highway construction destroyed portions of our neighborhoods and then divided them for decades to come.
I feel that very acutely in Ward 9, because we have four underpasses in Ward 9 alone with I-91 that again divided these two incredible neighborhoods from one another. The way that you described your visit to Charleston really resonated with me, because you feel that on either end of the highway. Not only that, but you also see the rippling impacts of the highway construction, not only from an emotional level, but a very tangible level.
Some of the issues that I heard the most on the doors when I was first running for office was about traffic safety, was about how do we invest in our young people, was about lack of affordable housing. All of those issues are relevant to the I-91 highway. The I-91 highway destroyed thousands of housing units in our community.
Also, when I first started my term, I got the crash report data from the New Haven Police Department. Each of the intersections near the highway are the areas where the most motor vehicle crashes with people going on and off, speeding on and off the highway.
So tackling the I-91 experience in the city from a very tangible and practical level, but also an emotional level, to see, "Okay, can we as a city, if we were a leader in urban renewal back in the mid-1900s, can we turn this past of pain into a future of promise in our city?"
Some of the things that we've focused on as a result is I worked with my colleagues on the Board of Alders as well as the city of New Haven to apply for one of the Biden administration's Reconnecting Communities grants. We received a $2 million grant to launch the I-91 Neighborhood Reconnection Initiative to do this very thing—to take a holistic look at the entire I-91 stretch within New Haven, look at some of the intersections in and around the highway to make them safer for neighbors, for pedestrians, for drivers, as well as thinking about things as visionary as, "Are there some exits that we might not need anymore that could unlock available land for housing?"
As well as looking at some of the underpasses under I-91 and can we transform these from areas of neglect to areas that are assets in our community? The last thing I'll share on that is we've really zeroed in on one of those underpasses in Ward 9, right behind the Ralph Walker Hockey Rink, which is a large area. We've been working over the better part of the last year and a half on a visioning process to transform that area into an Underpass Park.
We received a grant from AARP Livable Communities grant, as well as a National Endowment of the Arts grant to go through a design process to reimagine that area into a place for young people to skateboard, to play basketball, for adults to enjoy the river that runs through there.
So I think it's been a privilege. The last thing I'll say is I think it's been a privilege to—in all of the stories that I heard on the doors from so many different neighborhoods—to be able to find a way to work on a project that touches each of those issues by focusing on the I-91 highway, which looms over us as a city, and think about a way that we can reconnect our neighborhoods through a strategic approach.
What has your role so far taught you about how local leaders—I guess you could say politicians, but not really. That's not really. Just people who are serving in public office. Let's put it that way. About the influence they can have on the direction of their communities, but also the limitations? How do you wrestle with both the opportunity but also the limits of serving in public office?
I think that's a really interesting question. The first idea that comes to mind is a mentor of mine, who's a former mayor of New Haven, talks a lot about the power of the will to act. He believes that power comes from the choice that we all collectively have to act on something and build a coalition of people around it to get it done.
So I think something that I've witnessed on a micro level in Ward 9 is we have so many opportunities to make the choice to say, "We're actually going to do something about this," and we have the ability to bring a lot of people together to be able to move as a collective towards that horizon line of getting it done.
So a myriad of different examples, whether it's everything from the I-91 Neighborhood Reconnection Initiative project, to projects like the Lawrence Street Plaza, where we brought a group of neighbors together to pedestrianize this stretch, which increased traffic safety and also created this shared public space in the community, to tackling issues like the Willow and Nicoll intersection, which I know we'll talk about, which Strong Towns played a role in.
In each of those, what I noticed was us making the choice to say, "This is an issue that's been an issue for 10 plus years in our neighborhood, in our community, and we're going to do something about it." We don't know how necessarily. We don't know how we're going to get the resources. We don't know how it's all going to fall into place, but we know this is an issue that we want to actually get something done. In some ways, that choice in and of itself is a source of fuel and power.
I think there are always constraints. The first one that's coming to mind is, in many ways, just the belief that something can change. I've knocked on doors of neighbors who say, "I am not registered to vote, because no matter if the candidate is Democrat or Republican, old or young, they don't have my back. Nothing's going to change."
I get that. I don't think that's true. I don't believe that's true. I wouldn't be in this role if I didn't believe that was true. But I don't think that's unreasonable, given some of the experiences that people have had and given, in many ways, the erosion in belief in what government can do to make a change on people's everyday lives.
I think the challenge, but the opportunity that we have on a local level is that our work is visible, that it can be visible. We can do—whether it's everything from putting the stop sign that needed to be there 10 years ago, to we're going to host a workshop on our Board of Education budget, to we're going to work on a project that might take 10 years, but we're going to bring neighbors together about it now.
Because of the intimacy of a neighborhood and the intimacy of a 138,000-person town, we have the ability to get things done, or begin to get things done in a way that's visible and seen because of the power of human relationship, and because we are neighbors.
I get excited, and it's a privilege to be a part of local government, because we have a kind of front porch step ability to build faith in government. It starts with actually—rebuilding faith in government starts with actually working on the things that matter to people. But also it means being in conversation with people and making sure they know about what's happening, but also bringing them into the fold and saying, "Hey, become be a part of this. Be a part of this project."
My hope is that that helps to push against that limitation and that constraint, that there are still people in every single neighborhood, in every single community, who don't believe anything can get done.
Do you ever struggle with how long it takes to get things done?
Yes, I do. I do. I'd be curious where that comes from for you, because I wouldn't be surprised if maybe your answer is yes.
I do think, however, two things. Things take time. We have constraints and resources. I think two things that help to mitigate the fact that things do take a long time sometimes. Is one, a spirit of yes, an orientation of yes, an affect of yes, I think is helpful. Then being really clear about the steps in the process and bringing people along the journey, and having individuals and neighbors help to lead the process, I think that helps.
Because, yes, things take time. There can be intersections, given limited constraints, where we won't have sidewalk bump outs for the next four years. But can our orientation to someone making that request be, "Yes, and let me tell you why, and bring you into the fold of that why it'll take four years. Here's what we can do in the meantime. Here's how we can put up bollards. Here's how we can still mitigate this issue."
There's—it's more than just yes or no. I think it's much more complex and much more interesting and much more robust than that, to make the frustration of how long things take actually an opportunity to bring people into the fold of change.
But what do you think? How does that land for you?
In terms of time? Yes, I've never served in public office, so I understand that my perspective on this is quite limited. I just think there's so much opportunity for innovating how local government works and really taking a step back and saying, "Hey, this is the system, the patterns that we've been handed down." I know to the extent that we're going to rely on state or federal resources or policies or whatever, it's going to take time. But is there anything we can do to simplify things and make things more agile?
Because, yeah, I think it is just very frustrating for a lot of people when they see their place and they know that there are problems and that there could be solutions, but they have to tell themselves, "Even if we start on this today, it might be 2, 3, 5, 7 years before we see any progress on it." That just, I think, can really drain energy from people who would like to do things.
So I don't know. Yeah, I think I understand it. I just think the time is definitely coming where we're going to have to rethink how local government works, and sort of, what are the frameworks and paradigms that govern decision-making and how we navigate change, or how we find that balance between creating certainty, which I know is a big part of a reason why institutions exist, but also not let the need for certainty completely deprive our place of the ability to experiment and try new things or adapt and be resilient. Because that also has to be important. You need certainty, but you also need resilience.
If you have a ton of rules and regulations, and if you have long processes, or if you have so many codependencies where you just can't make a single decision for yourself—"Well, we don't know. We have to ask this department for that, and we have to go talk to the state for this and the feds for that." It's, "Well, certainly we can shrink that level of codependency, or interdependency, I should say, so that we can—"
Yeah, how do we navigate that need for both certainty, because you need certainty for people to invest, you need reliability for people to invest, but you also need agility for people to be able to respond? I think we need to kind of take a step back. I think local government—I don't know, I think it's a good time to start to take a step back and say, "Where are we on this spectrum? Are we so high on certainty that we completely are not able to adapt or respond or be agile, or are we so interested in agility and resilience that we've sacrificed the very certainty that people need to even make investments?"
So there's a lot of opportunity for a really interesting conversation there.
Yeah, I think that's a really, really elegant point. I hadn't thought about that as a dichotomous spectrum, but I think it's really smart, and I'm going to think about that more. I think what you're sharing has deep resonance with me.
One of my priorities in this next term is specifically focused around this idea as it relates to the permitting and licensing process for small businesses.
Yeah, well, I was gonna say, because I could tell from your work on the small business side, I think I was, "I know you get this." Yes. Needing to simplify processes, make things easier, make it easier for people to test ideas and get out there and do their crazy, audacious plan.
So I know you definitely resonate with that, but yeah, tell us more about this initiative that you're hoping to pursue in this new term.
Yeah, so in January, we hope to launch an effort called Best City to Start. It's a policy campaign focusing on a key set of legislative changes to make it easier for a business to start in the city of New Haven.
What you just described, that erosion of hope and faith that happens, happens all the time for small businesses. They're already incurring a risk. They're starting something. They're building something. They're putting themselves out there. It shouldn't take months or years, or cost hundreds or thousands of dollars, or erode at someone's faith to be able to get something and be able to start trying something out.
So whether it's everything from taking a look at our fines and fees, or taking a look at some of our permits for low risk packaged goods like pickle jars and jam jars, or taking a closer look at our sidewalk patio and outdoor dining policies, there's a range of different permits and licenses, as well as processes that, through legislative fixes, can make it a lot easier for someone to just get started, take a risk, and take that leap.
There's so many different reasons why small businesses have become a core part of my depth of care for New Haven and for our city, in large part because I'm an entrepreneur, and I've been able to have that experience of trying something and the ways it creates—it's so hard, but it creates so much meaning for a team. But also because small businesses are one of the most trusted institutions in the country right now. I think it's something like 86% of individuals believe that small businesses make a positive impact on a community.
Small businesses are where people gather. It's the place that people go in the morning for their regular routine. It's the place they go at the end of a hard week. They create jobs for a community, all the things that we know keep dollars here. I think it's an area that's just ripe for investment and a close level of rigor to take a look at our policies and see, "Are these working? What are we protecting here? What, as a result, are we standing in the way of? How do we create more of the conditions for that spirit of yes?"
To your point, more innovation and agility and the ability to be a city where people can try things out and be able to fail safely, and more than anything, have more of the opportunity to be able to build something that is, as we know on so many different levels, so beneficial for our neighborhoods. Having good outdoor dining makes the street safer and more vibrant. Having more outdoor patios and live music that happens creates more opportunities for people to spend their Friday nights in our city, just makes us happier.
So that's gonna be a big priority of mine going into this term.
It seems to me that one of the themes of your work, and you've said this, and I can just kind of hear it—I can see it as a constant thread in so many of your answers—is really this idea of, what can we do to get people out and liking each other and be more than just people who live in the same city, to be neighbors, to even maybe even be friends?
How do you think about the challenge of building social fabric right now? We've talked about this a little bit, but how do you think about that challenge in terms of—whether it's a challenge of the built environment, creating literal, physical spaces that align with our neurological design to elicit certain types of behaviors? Or if it's policy—"Well, we need places for people to be. Let's make it easier for people to start small businesses." If it's safety—"Well, there's too much traffic on the street. No one's going to want to hang out here. Let's fix this street."
But I feel like the end for you is not a safer street, a nicer business. It's people spending time together and feeling connected to each other and to this place. That's really the ultimate thing that you're going for.
But there are a lot of challenges with that as well. If it's how much time people are spending on their phones now, or the fear people have about strangers, or just about feeling disoriented socially, or if it's—we talked about how so many decisions are driven by the market. People pick a neighborhood based on what they can afford, not based on a sense of identity. Neighborhoods, it's hard for them to have a sense of identity anymore.
So I'm just curious, how do you think about this dream, this map of making your city a place where more of that magic happens that you talked about at the beginning, but also these challenges of how so many forces are working against us, almost to the opposite end of getting us to retreat further and further inwards until all we're doing is sitting down, scrolling on our phone, buying stuff? I guess is that the ultimate goal? I don't know if anyone would ever say that explicitly, but how do you wrestle with the counter forces? I guess is what I'm asking.
Such a beautiful and sort of wrenching question. I'd be really curious how you answer it.
Some of my underlying assumptions and beliefs include that I believe we're in a moment in time where many individuals hunger to be engaged, but don't necessarily have the tools or the permission structure in themselves, or the kind of bridge to be able to take that energy and turn it into something real.
Also, my second assumption is that when we think about our favorite nights of the year, I believe most of us still would prefer to sit across the table or sit at a bar across from someone we disagree with, or someone that we debate with. We would remember that night far more, and hunger for that night far more than we would a night where it's 8:30 p.m. and we're scrolling on our phone.
So the question is, on a local level, how do we tap into both of those or create tools or policies that are built on those assumptions, that there is a hunger from many to be engaged and that we love it when we do, even if it's hard or even if we don't have those bridges? We love it when we do, even when it's tough, or even when it results in the friction, the inevitable friction of human relationship. Because the nature of human relationship is that there's friction there.
Some of the things that—I mean, there's so many different pieces of that. There's walkability. There's the role of density of housing, all the things that you've talked about. There's the investment in public space and just casual public space for people to spend time with each other.
Some of the concrete things that I've been working on—one, me and a close friend of mine, Miles Lasater, launched a program called the Know Your Neighbors Fund. These are $100 micro grants given to individual neighbors who want to organize an event or a series of events that bring neighbors together—everything from a Saturday morning basketball league to a neighborhood cleanup to a chess club on Friday mornings.
Part of the purpose of this is we were inspired by a number of things. Inspired by, I think the City of Cambridge provides $250 grants for individuals who want to host a block party, which we were very inspired by. Part of it is that it's certainly about providing and lessening one hurdle of funding to be able to get an idea out there, purchase a couple of chess boards or purchase a few basketballs. But more than anything, it's about creating a bit of the permission structure and a bit of the spirit and the vision of saying, "Hey, that idea of a knitting club, or that idea of a dance party, or that idea of a community potluck that you've had in the back of your head for a while. If you hear about this grant, maybe you apply. Maybe you don't. Maybe you just do it anyway, because now you're excited about it. You have this feeling that you're a part of something bigger and part of a movement that's saying, 'Let's do these things more. Let's lean into these acts more,' even if just two people come."
A second program, also with Miles that we've been doing for the last year and a half is an event series called Start New Haven, which is a community pitch night, where it takes a really expansive definition of innovation. So individuals pitch ideas, whether it's a new zine series to a way of expanding internet across the city. They pitch these ideas, and we bring a group of neighbors around to support them to take that idea and make it materialize.
It doesn't have to be again, a business or a startup. It could be public art. It could be any kind of idea. It's all just to say through—whether it's these micro grant programs or these community events—we're trying to create the sort of community infrastructure at scale across the city so that individuals can—again, whether or not they go or not, they hear about it, and maybe they are led by their own instinct to say, "Actually, you know what? I'm going to text five friends and we're going to go play basketball at Wilbur Cross basketball courts."
But how about you? So those are a couple things that we're working on. What would you want to see if you could wave a magic wand and make one investment in our social and civic fabric across multiple cities to bring more people together? What would you change?
I would give them problems to solve. Yeah, I would find a way to let people solve some more of their own problems and make it really, really easy to solve problems.
I think there's—you've been seeing new apps come out where it's, "Hey, if you see a problem, you can report it and someone will fix it, maybe." Or you can go to a city meeting and try to get someone to come solve that problem. I think there's a case to be made for—I don't know what we would call this department—Department of Normal People Fixing Things, just the Department of—
That would look great on a jacket.
Something like this, where it's, "Hey, find some money, pay 10 people to be on the team, and you find ways to solve problems." I don't know. I just think we've lost something with exporting our problems to experts and then complaining when they don't do it the way we think they should do it.
What if we found a way to say, "Hey, you guys get together? Here's—I don't know if it'd be grant based, or if it'd just be volunteer roles or staff roles, or how you would do it, but if there's a way that people are empowered to come together and actually solve their own problems, I think people are motivated into community for various reasons. Necessity. Hospitality. Survival. We have to survive, so we're gonna have to figure out how to get along. Most of our communities don't run off of survival. Really, most of them don't, not anymore.
Hospitality can be one. You can have positive motivators—"Oh, there's this event, there's this social programming." You can have social motivators to creating those loose ties. But I think you can also have practical motivators, or sort of not really survival, but sort of necessity. Maybe it's, "Well, if we want to solve this problem, we have to all come together and actually solve this problem."
I think hopefully you don't ever fall so far—we don't fall apart enough to the point where we have to be functioning out of this sheer need to survive. I think hospitality is great, but it's still very—it's still very uphill. It's almost competing for people's leisure time. People's leisure time is so rare, and there's so little of it that it's very high competition to get people to use their leisure time in that way.
But I think if we had something around, "Well, if you know, here are the problems. We'll help you solve—if we can empower people to solve the problems in their community, that can also be a way to bring people come together." Probably pretty risky, though, but I don't know. I think it's kind of wild, but it's, "What if we were in charge of cleaning up the snow off of our street? Or, what if we had to actually figure out a solution for whatever challenge?"
If it's, "The cars are going too fast down our street"—well, there's a way we can actually solve this problem. We don't have to worry about jumping through a million hoops to get permission to do it. We can just solve it. I think you saw some of this during COVID, where people just started solving problems suddenly. Yeah, let's figure out a way to empower people to do that.
Two questions building off of that. One, what stands in the way of that? That sounds very creative.
Getting in trouble. I think it's liability concerns, and I think it's—I mean, people—there was a story on Strong Towns earlier this year where someone literally got put in jail for trying to solve a problem on their street. I can't remember what it was for, if it was traffic calming or something like that. But people are afraid that they're going to break some rule and they're going to get in trouble with the law, or they're afraid that they'll be a liability concern with whatever they do and they'll get in trouble, or it's too difficult to figure out what the rules are and how can we even take a first step here.
So I think that's what stops people from solving problems. I think also, people don't want to do this type of stuff alone. They want camaraderie of other people doing it with them. They want to share the risk. They want the risk to be distributed, and they also want the energy to be shared. They want the compounded energy.
So I think it's tricky trying to find someone—"How do I find other neighbors who would even be interested in taking on this kind of risk, even if we just went for it?" But then it's really difficult to even know what the rules are. Most people don't know how to get started figuring out, "Well, what are the rules we need to know, or the department we need to talk to?"
Then I think they're afraid. I think there's a lot of fear around liability concerns and, yeah, not wanting to do something that's technically illegal.
Last question on this. Does an issue come to mind? Whether it's parking in those standing zones or street sweeping leaves that you feel like is low-hanging fruit to try this? If you were kind of trying to move closer to the vision of a Problem Solved by Normal People department, what would be the first issue that you think is low-hanging fruit and kind of a paragon example of getting us closer to this?
Trash pickups. That'd be a really easy one. I think the challenges that really can have a huge effect on the quality of life in a neighborhood—you're looking at trash, you're looking at blight, you're looking at things like loose dogs that make people not want to be out in their neighborhood.
So I think those could be some—I mean, the dog one might be kind of tricky, because obviously you can't run around just catching scary dogs that you don't know. But I think, yeah, if there's a way to tackle trash and blight—the blight one might even be tricky, but maybe trash is pretty easy.
I mean, it kind of depends if the problem you're trying to solve is an actual external problem on the material world, or if there's actually a problem before that, which is we don't even know anybody in this neighborhood. So how are we going to solve this problem if we don't even know each other?
So that might be the actual first thing to solve is, "Well, how do we get to know other people here and figure out what the appetite is for even making any kind of investment?" So that might be step one is, "Well, how do we figure out who are our neighbors, and who's willing to invest any of their energy into this?" Then step two, yeah, identifying that low-hanging fruit.
But I think trash pickups have always been pretty—maybe do something positive. It's, "Let's have a pie day," you know? But, yeah, I don't know. It's good to think. I mean, I guess I'm thinking about my neighborhood. We do have a lot of—I would say we have a fair amount of blight. We have a fair amount, and we do have a serious loose dog problem. It creates a lot of uncertainty. It creates so much uncertainty people won't take walks. It could be just one dog, just seeing one dog one time, could be enough to keep people indoors.
We do have speeding traffic. We do have a lot of—I'm personally not a fan of on-street parking, so that's probably not a real issue. That's just one of Tiffany's pet peeves. But we also just have a problem where people don't know each other. I think it's really hard because people don't know how to solve that problem when you don't have a third place to get everyone together.
But there are a lot of other issues in my neighborhood in particular, but I think one of them is, "Well, how do we even get people to give up a little of their leisure time and consider it a worthwhile investment to spend some of that time actually on the community?"
Well, this is a fantastic conversation. I'm so glad we got to bring you on. I feel like we could talk about a million more topics and just keep exchanging thoughts and going back and forth. But in closing, you get to tell us a little bit more about your town, because I ask this question of all of our guests. Tell us a little bit about New Haven, specifically, a few local businesses that you like to recommend people check out if they were to come to visit.
It's so hard to choose. I would say a couple come to mind. One is my favorite park in New Haven is Criscuolo Park, which is in the Fair Haven neighborhood. It's a beautiful park where you can play basketball right near the river and see the historic, award-winning Quinnipiac Bridge go by. I think it's just absolutely just one of the most beautiful places to play basketball or to go for a walk.
A couple restaurants—I mean, there's so many. New Haven has incredible food entrepreneurs, but a couple that have a special place in my heart. One is a taco shop that's right at the corner of Lombard and Ferry—some of the best tacos that you can get in town. I particularly like their chorizo tacos. It's owned by an incredible guy, Omar. I'll send you the link, Tiffany, to that taco spot.
Then, New Haven has incredible pizza. It's known for pizza. It's really nationally recognized for pizza. There's so many incredible spots—Modern, Pepe's, among many, many, Sally's, among so many others. Ernie's has a really special place in my heart. The guys there that work at Ernie's give so much of their pizza away to families that need it, are just so community-minded.
They're a bit newer. They have this incredible honey pot pizza where they have pepperoni and cheese and then put honey on it, and it tastes incredible. Just both, both those small business owners, Omar and the team over at Ernie's, are just so committed to the community. I just wanted to show them both some love.
I always have to ask, do you have a favorite coffee shop? My favorite coffee shop, pub, kind of third space, just hangout vibe, sort of—
Well, the first spot that comes to mind is right in the heart of Ward 9, the Crooked Goat. It's a really great bar and restaurant that sells somewhat Southern cuisine. It's inspired by Southern cuisine.
I recently had an Alder Around Town event. I launched this new series called Alder Around Town, where I'll be going to different restaurants to support small businesses and just bring neighbors together. They're the first place. I hosted one just last week.
What I really appreciate about them—the three owners have been in the community for a really long time. They're born and raised here, and they all came together to start this new spot. It's only been around for a year, but it feels like they've been there for 40 plus years. It feels already like a legendary bar, and that's just a testament to them, these three men who have—you can just tell every inch of the restaurant is fueled by a little bit of love and care for the city. So I would say check out the Crooked Goat. They're amazing.
Well, Caroline, thank you so much for joining me on the Bottom Up Revolution. This was a lot of fun talking with you. Yeah, I'm excited for you, for your next term, and all the challenges and opportunities you'll be able to put your energy towards.
To our listeners, thank you so much for joining us for this fantastic conversation. I hope you have a wonderful holiday season. Can't believe how fast Christmas is coming up and how fast a new year is approaching. If you don't know, we have a link in our show where you can nominate someone in your community who you think we should have on for an interview. So yeah, we're definitely looking for new guests as we go into 2026. So if there's someone who you think would make a great fit, please use that link to let us know.
I will be back soon with another conversation. In the meantime, keep doing what you can to build a strong town.
Thank you so much, Tiffany. This is great.
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