From Startup to Human Connection: Winsome on Building Community

So Winsome, please tell us, the world, our listeners, who are you? Hi, I'm Winsome, serial entrepreneur, working on what I think is a really fun project right now, all around getting people to share a meal with each other so that we can really get back to the basics of human connection. But yeah, I mean, I'm a mom. I have a three-year-old, a five-year-old. And I moved here to Grand Rapids about eight years ago from New York City. So I guess I'm a Michigander too. Yeah, at what point? You're not from Michigan. No, no, I moved here from New York. And I didn't grow up explicitly in New York. I kind of grew up moving around tri-state area up and down the East Coast. But I would say I think I cemented my Michigander status after... After you bought a house, yeah, when you bought a house, I was like, yeah, this feels right. Yeah. We're staying for a little while. Three winters, I think, is when you're allowed to certify yourself as a Michigander. I was thinking it was going to be more like when you say some of the Michigan things, like, do you say, yeah, no? You don't have the Michigan A's yet. You pass by someone and say, oh. What are some of your observations on becoming a Michigander, especially from a place like New York, which I think Michigan I think both New Yorkers and Michiganders somewhat look down their nose at each other. There's definitely truth to that. I mean, the grass is always greener, right? But I think Michigan is a wonderful place. I would say the things I miss most about New York City are anonymity. Being able to, you know, look like a bum and go to the supermarket and know that no one's going to recognize you. And there's always someone doing something crazier than you are. So it's fine. And then I miss having an international airport. And I know Grand Rapids is an international airport in quotes, but you know, it doesn't hold a candle next to JFK. I mean, maybe that's a plug to our airport. I think they're working on it. They are working on it. There's some stages and international, but we don't have another country. Yeah. And they have like Mexico too, right? Yeah. So we're working on getting. The customs so that's right as part of the video. Yeah. Oh, that's cool. Yeah, I know what the timeline is but it is announced. Yeah, yeah, it's a it's definitely Right here that would keep you here that would make I mean I've been here for a little while Yeah, I mean not something I probably would have done in New York City But yeah, I think the thing that has been most different about living here, obviously winter is a little harsher, a little grayer, a little darker. But that's fine. I have a nice winter coat. I honestly feeling like I can really get to know people has been a little bit hard. And I feel like as I've... you know, socialize with more born and raised Michiganders and other folks who have also transplanted. It's a pretty common theme. Like, yeah, getting here and like really feeling like you have your sense of community just takes a while. And I think that is a testament to how tight knit communities are here, which is awesome. But yeah, I don't know. That's probably like the biggest observation in New York City. There's so many people that have transplanted, you know, they're just, you can always find a connection. I love that you refer to yourself as a serial entrepreneur. People with the spirit like that make me jealous because you're always trying new things. I know it's not easy. We met years ago when you were in the throes of a different business that was great but probably ran its course it was such a cool thing that vision that you had I do want to know more about what you're doing now but I'm also curious about just the ecosystem of this community because I feel like that's one of the things that Grand Rapids continues to want to be is a place that that people can dream they can build how's that been for you and what does that look like for how the community has supported or what you've either gaps or things that you'd identify for other people So, I mean, I would say my first business, Pack Elephant, got a really warm welcome from Grand Rapids, and that's part of what helped me find community here. It was a corporate gift box company that highlighted small businesses, local businesses primarily, and packaged them up into these beautiful gift boxes for corporations that were doing internal gifts and client gifts. I think that Grand Rapids really does want to support the small business ecosystem. I think it's a great place to do that. What I have found as an entrepreneur is that there is, you know... this gap between the small business and then becoming the big business, the national business that started in Grand Rapids. And to get to that next phase, really it's like phase three or four or five, right? Like it takes a while to grow to that, but it takes capital, it takes a lot of resources. And I would say it's not just Grand Rapids, the Midwest in general is a little bit more risk averse when it comes to investing in businesses that allow them to grow into that larger national business. So interesting. Yeah, I think if you know your goal is to be a small business owner that grows more slowly and that's fine. That's great. You know, there are a lot of lifestyle businesses that grow at a steady pace and become just, you know, great pieces of their community and invest back in their community and hire folks from the community. I think what I'm working on now is something that I hope does scale more than that. And I think Grand Rapids has come a long way in trying to help businesses achieve that type of goal. So what I'm working on now, Breaking Bread AI, is a platform that helps facilitate in-person gatherings. So don't think of it as your typical kind of social connection app, because I think those really optimize for scale, like how many people can I connect with? but it doesn't really prioritize in-depth connection. What I'm doing is really trying to get people in small groups of four to six people to share a meal with each other because that's where you know you really can learn about someone and and be known as well. I started this last year. I'm about six months in. The platform launched just, you know, a couple months ago. We're still in the sausage-making phase of it, so a lot of grace is required for my pilot customers. But I did an accelerator program through the MSU Research Foundation. It's called Conquer, which was really helpful in just giving us, you know, access to some of the resources at the university. has, but also putting us kind of elevating what we're doing on the Michigan stage so that we can get other opportunities like be, you know, I'm going to be down at South by Southwest in March with Breaking Bread AI. Yeah, this is a, it's a fun part of the building process that I'm in right now. But I would say for anyone that does want to start a business here, there are a lot of opportunities and they're only growing. So that's great. That's awesome. Yeah. Yeah, listen, you know, you're talking about like how the challenge of getting to know people as a transplant to the area. And I have to imagine that that problem, you're in some ways inspired by solving it through breaking bread, I imagine. Is that part of the origin of like what was the impetus of breaking bread? Yeah, I mean, breaking bread AI. Yeah, we are using data and algorithms. Not just cookies and breadcrumbs. Yeah, I, you know, I think had this epiphany sometime, probably around this time last year that, you know, I have made a lot of connections in Michigan and Grand Rapids, but. Many of them were around my my former business, you know, and when I decided to close the doors on pack elephant I was kind of wondering like wait, where? Who can I mourn this with you know and like who are my friends that I can you know just really share this experience with that that are not or that are better local and I think you know amid this I kind of thought back to all of the moments where I did feel like I belonged here and like I did have friends and I did have a community and those are all those were all around like these these informal like moments at someone's house. You know, I remember, I think the first Christmas that we were here in Grand Rapids, my husband, who's a physician, he was on call, so we couldn't go back home to our family. And his mentor, which was another doctor at the hospital, invited us over to have dinner with their family. And that just felt like such a like a wonderful, like warm moment that doesn't happen very often. And I was really craving more of that. And I think, you know, if you look at just where we are, you know, as a society, in, you know, 2023, we got the surge in general warning, loneliness as an epidemic. I think, you know, with the kind of tense political situation, you know, people really do feel the sense of isolation and like it's hard to connect, especially Beyond you know social media where we feel connected, but when you put your phone down Who's around you? So so it did kind of inspire this, you know, wait, how do I get back to feeling more connected with the people around me? And as you know, at leadership Grand Rapids kind of did this really informal project mean and one of our other Colleagues just started asking folks like hey, would you be willing to host dinners at your house? And to our surprise, the majority of the class signed up. And then after we did this experiment and surveyed people to see how connected they felt with each other, 100% of the people who participated, literally every single person was like, wow, I feel like I understand people in our cohort better. And by the way, I would love to do this again. And for the folks that didn't sign up initially because it wasn't the right time or because they weren't sure, you know, what the expectation was, they all wanted in on it too, right? There was like this sense of FOMO, like, wow, that watching this happen in real time felt really special. And I happened to be at a moment where I was kind of wondering what this next foray was going to be for me in this world of entrepreneurship. thought, hey, I should build something that helps people do this. And not just anyone, right? I think there's, there are some other platforms and tools popping up here and there that are all about, like friend finding. We think like Bumble for friends, you know, you can kind of architect those. those chance encounters that maybe feel more curated because you're being matched with someone based on your social tendencies and your personality. But I think that what we need to really focus on is those connections that we already have. Like there is staying power in optimizing relationships where we already see each other with some frequency. We already share, you know, a bond. There's already a thread there that connects us. How do we turn that kind of connection into something that has the potential to really flourish into more? Something that I've been thinking about, and Allie and I have talked about a few times, like I agree completely with what you're saying. What I'm wondering about is how how something like Breaking Bread AI sees things like healthy conflict, that finding deeper connections with people is, as we know from all of us being LGR alumni, that part of part of creating those connections and fostering them is healthy conflict and to being able to have hard conversations with people that that respect you despite you know disagreeing with you and I'm wondering how how do you see breaking bread AI tackling that problem or at least addressing it yeah in any sort of interesting ways well I think any healthy conflict starts with like acknowledging you know others humanity And I think on a really basic level, just sitting down and sharing a meal, that's an environment where we're human beings, we all do this. Everyone needs to eat. Everyone likes some form of bread, even if you're gluten-free. But, you know, our platform, we do have a series of questions. So there's a questionnaire. It's quick to fill out. It's based on the big five personality tests. And we do look at things like, you know, what is your conflict style? Like what your communication style? Are you someone that, you know, is really a straight shooter and you just kind of tell it like it is? Or are you someone that. really approaches things with more of a diplomacy first mindset. And that's just one of many kind of things that we have on our sliding scale that you can, you know, decide where on the spectrum you fall. But I think that's a good example of like one of those measures where we would likely want to limit the groups that have people that are on the opposite side of the spectrum there because there's so much more opportunity for miscommunication. And it has nothing to do with politics. It has nothing to do with what your interests are. It really is like how do you show up when something is a little bit uncomfortable? The other thing I would say is, Yeah, we, the, the, the goal of breaking bread and like the, the ethos of the brand is let's try and understand like where each other, like where we're coming from. Like that's, that's kind of the, the point and the people who so far have been engaging with this, um, are the people that, you know, feel strongly about like trying to, um, reach out and understand other perspectives. So kind of draws a specific type of person. I think there's a really neat element to the idea behind having it in your home, right? Because I think we've gotten into this culture of let's just meet for an hour or let's go to this place. Right. And I think there's a different level of intimacy when you welcome somebody into your home or when you have the respect of going into someone else's home and also gives you that opportunity to just like be more casual isn't the right word, but it's just more, it's more connected, right? And it definitely gives you that. And I think we've, we don't prioritize that. I don't, I don't, I've never had anybody over. to my home. My current home. So you haven't just not prioritized it, you just don't do it. I just don't do it. It gives you that. So what's stopping you? Is it because it's awkward to reach out to people and say like, hey, come over? Or do you like your space? Like what is driving that decision? It's the red couches, right? It's the red couches. It's a good reminder of how much we appreciate when other people... invite us into their space and why we should also be thinking about that for people to make genuine connections right yeah it's something about the inviting people into your space it's something i have struggled with both on both extremes like having my kids are eight and ten almost eleven so you know when they're younger sometimes it's easier to stay home but then also there's kind of that like curated bomb community of like the perfect home and or you know having friends who are in different places in their lives and their work lives of the ability to do that versus not and kind of like a fear of judgment that comes even from people that you know and love right and i've found recently in going to some different people's homes who are at a similar stage in life like the term i keep hearing people say is like you know, I'd love for you to come over, but just so you know, like, I haven't, like, we haven't cleaned up, like, my house looks lived in right now. Like, I keep hearing that. It should. Right. You live there. It should. It should, but like, it is, you know, it's easy to say here, like, yes, your house should look lived in, but like, honestly, if you came over to my very lived in house right now, like. you may be horrified. People who live in my house leave food on the floor. That's my baseline. I mean, like I said, I have a three and five-year-old. But that's the point. People understand. And I think we internalize too often what we imagine people's judgments to be about our lived space. I have the same. We all struggle with that. And if we all struggle with that... Maybe we should all acknowledge that we all struggle with it. We can acknowledge it. And I think, you know, honestly, social media has a big role to play in. setting us up for these unrealistic expectations of what our home should look like and what gathering should look like. And it becomes this formal, picture-perfect ideal that we're all trying to achieve. And that's not the reality of being a human being that lives with your family. But all that said, we do have a lot of options for breaking bread. It doesn't have to be in your home. And that's one of the things that's evolved since doing this project with Leadership Grand Rapids. If you are more comfortable playing host at a restaurant, then you can do that too. Is that a sponsorship opportunity? it a sponsorship opportunity yes like oh yes absolutely so restaurants could sponsor it we're working to figure out like with restaurants what it looks like to create you know the familiarity of a breaking bread meal for folks that are hosting at a restaurant as opposed to their homes. And honestly, you know, some people want to go to a meal that is kid friendly and other people are like, I want to. actually be able to talk to people without chasing after my toddler. So I think just capturing all of these preferences is something that we've really baked into the process so that it can really be, you know, like show up as you are, where you are, because it being inclusive is I think the priority. I have another question unrelated to Breaking Bread AI. Yeah, shoot. Something that's been a hot question in my household this week has been, first of all, I think everyone at this table is familiar with six, seven, correct? I'm looking around. If I'm familiar, because I feel like I know what it, I know what it doesn't mean. I don't think anyone knows what it means. And also I think everyone kind of knows that it doesn't mean anything, if that makes sense. My question for the table, we're all, Not in the generation that is currently lifting up 6-7, if you will. What was your 6-7? An appropriate version of 6-7? Ideally. I'll give you an example. My best thing I think I can think of was my generation's, or at least when I was in middle school, high school, was peanut butter jelly time. Oh. Which didn't mean anything, had no... Like it didn't mean anything, but it was a thing that everyone just started saying Hi, the thing that pops into my head first is the lake that was a Like that was definitely like for me that was middle school Yeah, everybody said that was a I don't know I'm like am I gonna I don't know if I'm gonna age myself but um No, that's that's too inappropriate. Let's go. Let's go with YOLO YOLO my argument I've heard the YOLO argument but YOLO means something like you know has like a like six seven has is just chaos right and it's completely nothing to do with reality Like it's I feel like YOLO can mean that to you know we joke YOLO I agree with you and I think Yolo is like a cousin of Yolo is the like hashtag blessed. That's like not of my youth. That's of my like young adulthood of like hashtag blessed. Yeah. Yeah. Yeah. I don't know. It's like it's so overused. It doesn't mean anything. I think Elliot's got one. No, I'm struggling with this one and mostly because the first thing I can't get out of my head that every kid when I was young always just did this motion. Oh yeah, that's true. It was not an appropriate one. It had been. Meaning that was... But it also was just like nonsense at the same time. Right, that's a good example. It was just nonsense. Yeah, that's what I'm looking for. It was that absolute... And like you would try to do it like behind the teacher's back because you didn't want them to see it, right? I feel like that's what... Oh, that's just a real emotion. It's kind of like a real emotion, right? The thing that I... In the same vein, is that the thing that I felt was like absolute nonsense when I think of like peak... sixth grade time for me was boys like low riding their jeans like their butts showing did this happen in other places this was just the traverse city just traverse city do you know what i'm talking about like making jeans so low yeah no I know, that was definitely a thing. Both of you are looking at me like I'm insane. We were proper children. I don't know what was going on up north, but like down here in Grand Rapids, we had class. But it was so nonsensical. Like it did not. Well, is it the whole thing rooted in like having bigger brothers? I thought this was like the whole thing, like this fashion. No, it's here. Hear me out here like my understanding again. I'm like willing to be wrong as a cultural anthropologist The the the baggy jeans thing was a Started as a metaphor about like they were hand-me-down jeans from your brother And if you had large jeans it meant that like you had a big brother and like that meant something in some communities that it was like about you know I like that interpretation. That's not the origin story that I know. What do you do? Well, I mean, I honestly baggy jeans were like baggy clothes in general. If you think about like the prison industrial complex and people that were, yeah, coming or just used to being given clothes that were not, that didn't fit them properly. I think that's a huge part of why it was like a big part of, you know, inner city culture to have baggy clothes which just then became a I don't know like a street like a street wear like fashion statement but that's interesting because like I think that's a really interesting interpretation and you're probably on to something there it's really fascinating how that is still a thing, especially, you know, we talk about fashion often as being like this, like flat circle, and how fashion's never finished, that like things like that continue to come back, like baggy clothes, I think, especially like as we're seeing with the Shenzhen Alpha. Well now it's like cozy, like, yeah, comfort wear. We're good with this trend, we like this one. Yeah, but low rise. like low-rise flares for girls are coming back. And I'm like, oh my gosh, never again. I can't get out of my head now the vision of the group Criss Cross, right? And that was when I first remember seeing this baggy jeans, the backwards jeans, the low, and that became kind of a staple for, I think, our generation of like... That's cool. I like and I also never felt like I could do it Yeah, so yeah, six seven Yeah, I don't know that's that's a fun question I have to think about it. Yeah. Yeah, I should have given you as a prompt. I would have been a fun problem Yeah better ideas later. As a transplant, what do New Yorkers, like city or state by the way, I should have asked the city, right? What do New Yorkers get wrong about Michiganders and what do Michiganders get wrong about New Yorkers? Well, okay. First of all, we've moved out here. My husband matched for residency in Grand Rapids. So that was what landed us here. And I remember thinking like, are there going to be sidewalks? Mostly. Where was the place that you went that didn't have the sidewalk that you did that video about? Oh, Phoenix! Phoenix! You know, that's a seat in some places. Interesting. So, yeah. But yeah, no, I think that people that come to visit us are always so impressed and surprised by just how much infrastructure there is here. What a lumbar. I mean, they're like, wow. they're like tall buildings and like well yeah it's a city you know it's a small city but it's a city you know um and i mean i would say the one thing that michiganders get wrong about new yorkers is that um does that word mean i think there's um this like resting face Leave out the expletives, but there's a resting phase that people have because everything is just so fast-paced and everyone is like dealing all the time with just the inconveniences of you know density. Yeah, you know like you're Traveling an hour to get to work in the morning on the subway through crowds and like you're walking fast on the sidewalk because you're trying to just get where you're going and people think that New Yorkers are mean and I don't think they are Yeah, really nice. This week, this will contextualize when we're talking about this for people, but it's been interesting to watch this social media trend of these guys from Britain. I think it's Josh and Jace, is that right? Visiting Michigan, visiting Grand Rapids, and like, obviously they're doing like the great sides of it, right? But like just the things that have surprised them, and one of them being just like... Everybody here is so nice, right? I thought you were going to say the potholes. That's one that they're like, why are these roads falling apart? Sounds like a bigger issue that we need to work on. Fix the damn roads. Did we not fix them? Not from what I can see. What have we been doing this whole time? According to my front right tire, the roads are not fixed. I feel like they do, like they're working on them all the time, right? But then somehow they become unfixed. very quickly. It's one of the great, it's the mystery spot that is Michigan. It's like one of the great unknowns. Yeah, there's no possible solution for it. One of my favorite things is like treat yourself like a Michigan road and never ever stop working on yourself. It's funny you say. Always room for improvement. It's funny you talk about the infrastructure, like the like, do they have sidewalks? They're kind of thing. My aunt and that family live in New York. They Went from the city to Westchester, back to the city. And I remember when I was little, when we'd go out and visit, we would see the things that they had. The one that sticks out in my mind is Craft Easy Mac when it debuted. literally the conversation about like it will be years until you have this. And it was true. But basically like all the things like that debut in markets. Yeah. Because my mom grew up in Detroit. I grew up and then we lived in Traverse City. So my mom was like, we are not a big market. We may never have that. They might like retort your- You don't have to smuggle in your Kraft Mac and Cheese. Yeah, exactly. It was always like, and I- I lived in DC for the first decade of my career and I remember going to the grocery, seeing something, the Craft Easy Mac of my 20s, whatever that was, seeing the commercial of like a brand new product, going to the grocery store and seeing it and being like, oh, big market. I remember going to Chicago as a teenager and like feeling so special to like walk into a Chipotle. Oh yeah. Oh my gosh, incredible. Such fresh food. when we got our first starbucks here it was like oh yeah groundbreaking for this first starbucks here because there are a ton now i first feel like it was like the beltline in 20th street yeah i feel like that might have been and it was like it was We made it right as a city Trader Joe's like we Midwestern experience to like hear about these other things that like kava or sweet green that like other markets and major markets are getting and you know like it's eventually going to be here but you're like i hope it gets here while it's still cool Or like still good. Like, oh, I had a favorite salad from Sweetgreen that has like been discontinued. Like that's not even here yet. I will say though, I love just like the smaller mom and pop brands and like local restaurants, local businesses. I mean, that's, that's, you know, part of. part of what I what I do what I love but also that's something I think that Grand Rapids has going for it that other big markets sometimes don't have going for them so like it's a great point you know I appreciate it yeah what are some cares about easy Mac what are some what are some new ones that you have checked out recently that you'd recommend to where your local business is. Either like shops or restaurants. I stopped the other day. I know Pat Caliphant used to be at Studio Park. They've got a great space there at Curates. The person I went to school with, I didn't even realize had started a business. She has a flower shop now. Oh, and it's beautiful. And it's beautiful. And now she also moved, actually moved over to Wealthy because she got the opportunity to get a new space and just like following people's journeys. Oh, where is it on? Because you're getting used to that. Yeah. The Nixie Floral. Nixie Floral. Yeah. Because he was telling us that he went there and was like, I need a cat free. Yeah. A cat friendly bouquet. No cats and my flowers. No cats and my flowers. But like that they were really great. Maybe some cattails. So good. It's fun to see those things happen. I'm trying to think of like any recent new openings of restaurants or things that I'm checking out. That's a hard one because I feel like I've been hibernating in this season. So I'll have to get back to it. This is not a new one, but like one of my favorite small businesses is Rebel in Easttown with like my kids' complimentary one of Sticky Fingers owned by the same owners, but they're like candy, the nostalgia candy shop. That's a great one. Oh my gosh, but I have to like block a half hour to take them there. Because I'll be like, you could get one thing and it takes forever. I'm trying to think of any good. Places that have opened recently in there and Jr. I mean there are a ton of great restaurant. I mean of course new Yeah, where have I been that's new recently? Okay, let me try it a different way like what's the local place where like, you know You're like where will I always go like where I always be done for me If if my wife ever said like how do you feel about black napkin? I'd be like, let's do it. Let's go. Yeah, you know There's an automatic. Yes for me for black napkin I feel like I have a soft spot for Brewery Vivant. The duck fat fries. Duck fat fries, the nachos, I mean their burgers, everything. And then the beer, obviously. I am always a yes for a cocktail from Eastern Keel. Oh, I could have guessed that. It's a really good one. It's my favorite. I could never turn down Shea Olga. Oh, it is. And you said Easttown and it triggered me of like, I have not been there in months and now my mouth is watering all over it thinking about it. So that might be a weekend stop this weekend. Yeah, it is. I do think like this time of year is a good time to like think about the restaurants you haven't been to for a while. Like we went to, we used to go to Harmony all the time and we hadn't been for a while. And we went like, I think it was on New Year's Eve, like in the middle of the day and it was lovely. And it was like, so I think With all the stuff going on outside, like literally and figuratively, it's like a nice time to think about like, where haven't I been in a while that just like makes me feel good. Yeah. Black Napkin. We've been there recently. Not recent enough. I drove by Black Napkin last night. There's always a line. Always. It was like 10 degrees out and there was a line. And I mean, people are dedicated to those burgers. I know. I love it. They got a good thing going. Yeah. Well, on that note, close us out. What's next for you? What's next for Breaking Bread AI? Where are you going from here? Yeah. To Austin? No. That is so cool. Will you come back and tell us how it was? Oh, absolutely. I would love to. I would love to. Have you been to South By before? I have. Yep, yep. I went. many years ago. I feel like it was pre-COVID. I think it was the year COVID started. And they started shutting things down while we were there. And it was weird. But yeah, I mean, with Breaking Bread AI, I am really hopeful to have this in the hands of a few, a lot of different organizations, both in Grand Rapids and elsewhere, because I think now is the time. There is this timeliness to us. prioritizing our relationships and our connections. Do you have a tagline for Breaking Bad AI? I think you just said prioritize our relationships and connections. I feel like it needs a bread pun though. Does it need bread? We'll workshop it. Yeah. You guys, that's your job. We'll come back after Austin. We'll get back to you with some options and put them on screen and we'll go from there. Love it. All right, Winston, thank you so much for joining us. Thank you. Thank you guys. This is so much fun. Thank you. Great to see you.

In this episode, we talk with Winsome Kirton, a serial entrepreneur and founder of Breaking Bread AI, about loneliness, belonging, and why sharing a meal creates deeper connection than any app alone. We explore building community in the Midwest, scaling businesses, healthy conflict, and how informal gatherings can rebuild social trust.