Building Belonging in Startup Communities | Angela Damiani

I used to be a bunch of startup programming in the area, but it didn't really appeal to me before. Like, where are my people? There apparently were a couple other people who felt the same way. And so the origin of the Founder community was just one party we hosted in August of 2021. We called it Founder Fest. It was a room unlike any of the others I had been in. This is like a group of people I really want to be around. Hey everyone, and welcome back to the Startup Wisconsin podcast, a show where you can learn about Wisconsin's growing tech scene through stories of startups, founders, investors, and the talented people making it all happen. My guest today is Angela Damiani, CEO of NewWalkie, a brand engagement agency that helps organizations captivate, connect, and convert audiences through creative activations, events, and experiences. centralized network built for founders by founders, connecting them to community, capital, and customers. Milwaukee started as a social club, hosting meetups before meetup.com was even a thing. It took five years of selling merch and chasing sponsorships before they figured out the agency model that actually worked. The numbers show how far they've come. 17 years in business, around 200 productions in a six-month window, and 40% of their work now happens outside Wisconsin. They originated the Milwaukee Night Market, an event that now attracts an estimated 25,000 people in attendance per night. We talk about why belonging requires repeated, warm invitations, how she started the Midwest Founders community after feeling lonely coming out of the pandemic, and her critique that Wisconsin's investor class needs a higher risk tolerance if we want to see real innovation here in Wisconsin. All right folks, let's get into it. I want to go kind of back to the origin of your aspirations to becoming an entrepreneur. So what was the first thing in your life that kind of pulled you into becoming an entrepreneur or wanting to be an entrepreneur? Oh, I love this question because I did not think I wanted to be an entrepreneur, which is kind of funny now because I think, you know, all the work I do with the founder community, I feel like most of what I'm doing is like being a cheerleader, like goading people in, like, come on, just do it. Come on, make the jump. You can do it. but no, I didn't. I thought I was going to work in corporate America after college. And that's not exactly how the story started for me. I graduated in 08, like in the depths of those, that last recession. And so the job market was a little tricky. And quite frankly, I wanted to live abroad for a little bit. And so I did that. And I worked for the international press services right out of college. And there was a sales component to my job. And shortly after my very first sale, I remember thinking like, wow, I don't even like care about this and I can sell it. I wonder like what it would be like if I cared about what I was selling. And it was the first time I'd ever really had that sales experience. And it was the thing that sort of like planted the seed, like, okay, well, I got to just figure out what is it that I like want to do? Because I have it within me to like make money doing it. And that that was like maybe what sort of set the course. But it took me a little while after that to figure out what that was going to be. There were a couple of different iterations before we got to Milwaukee. All right. And how did like Milwaukee like come to be like what was like was there a person that kind of said, hey, do you want to do this with me? Was it your idea? How did Milwaukee come to life? There were a couple of us in the very beginning. Milwaukee's original intent was more of a social club. And there were a group of friends who moved down to the city slightly before I got involved and were hosting regular meetups. And those meetups were really popular. It was a time when I didn't even think meetup.com as a platform existed. And so it was very curious to us that strangers would want to come along and be our friends. And that initial kind of output helped us to really learn how do you do audience development you know what i mean it was sort of like a master class to be honest with you in in modern marketing and uh from that point a couple of us there were definitely more people at the beginning who were like helping to volunteer but there were a few of us who were like maybe this is like a thing we could do full-time you know what i mean like outside of our day jobs and it took us a minute to try to figure out like a a revenue model for it because we were pretty insistent uh that we wanted a programs we were offering to be free i'm just kind of funny to me now like why didn't we just charge people tickets or whatever but we were just like no what we're doing is really cool it needs to exist in the world we want to make it super accessible and so we dabbled in like different ways to monetize that then whether it be like selling concessions or merge or sponsorship and really that was just sort of like a rat race garnering those types of sales they're really hard you know because it's like super low price points corporations or companies don't really care so there's a lot of turnover and about five years in it was like well why don't we just treat this more like an agency and have like a time plus materials model that allows us to host these sort of bespoke experiences, but with someone who really wants to pay for it. And so it took it, we had all kinds of bumbling meanderings at the very beginning before we we moved into that. But it's been going great ever since. And there's been like continual, like iterations to about two years ago, we got away from just doing events and programs and into more like classical brand activations, like creating parklets or public art or installations at other people's events on behalf of clients. And so that's been a really fun and curious, like diversion for us. It has allowed us to do a number of silly things. Like we wrapped a van and turned it into a VR experience on behalf of and took it all over the whole state this year. So yeah, that kind of thing. That's like the very, It feels like it has the same kind of like magical energy to what people know of as a Milwaukee experience, but it's more mobile and way more interactive. Yeah, yeah. What was it like in kind of the early days of like, hey, you're this new agency or this new group of people that's put on these bespoke experiences. But now it feels like Milwaukee is like, it's like a name that people recognize and trust and like get excited about. So maybe talk about like, was there like a tipping point or a certain event that really kind of said, hey, wow, like if I'm going to get put on an event or do like brand activation at some point, these are the people I need to talk to. Was there like a moment or an event? Gosh, you know, I don't know if there was like one singular turning point, except, you know, we're going to be 17 years old at the top of the year. And so maybe it's just the staying power. You know what I mean? like really finding a way to just keep being consistent and to keep showing up over and over and over. And, you know, you can't tell, but I was much younger when this started. Um, and I think that was a benefit to the company in that we were very young when we started in our like barrier to entry was also low. You know what I mean? Like when I first started, I was like renting a room in my sister's house so I think I had to like come up with 350 a month for rent like that was like my total like how much money do we need to make you know what I mean like it was so so low that like it felt like there was almost no risk in us like scrapping about trying to make it happen and you know I think Milwaukee and I would say is like just a culture in the Midwest it's a where you have to have been here for a little bit for people to trust you. And I think the fact that we just keep showing up year after year really does help with that name brand recognition. And then the other thing that I think has made a difference is some of the stuff we've produced has taken a life on its own. We were the originators for the Milwaukee Night Market, which when we originally started had a couple dozen people coming to it. It was just sort of like a kooky nighttime art fair. And now in the summers, there's 100,000 people that go to it. You know what I mean? So it's really taken off and taken a life onto its own. And so I think because a lot of our work is very public, Milwaukee's brand gets elevated with that too. Sure. Yeah, for sure. Is there anything that you kind of learned along the way, whether it was on purpose or like by accident, whether it was like, you know, as you grew the team and the hiring process and like onboarding people and getting them up to speed? I know some of this is probably seasonal recruitment, but yeah, I guess what has been your experiences and learnings as you kind of like been in a business for so long, but also just learning to have a sense of like camaraderie with a business kind of ebbs and flows of the seasons, I guess. Yeah. I mean, I think one of the things we advocate for is that this is a very seasonal business. I don't know why, but nobody wants to host anything in January. So that means from May to November, that's the height of it for us. And it is a onslaught back to back to back. I mean, we probably have 200 productions in that six month window. So they stack on top of each other even. And I think the people who thrive here really love that dynamism that every day, nothing feels like it's a routine every day feels new and I think you know we spent a lot of time as a team talking about like how do you maintain your energy and your personal resilience through what feels like you know it's heavy it's heavy to just keep going and then you know what I mean I was telling you before we started like a lot of it's outside so it's also like braving the elements and all of that. I think the thing that I've learned along the way is that I really love to watch our team members grow. We're big enough now as an organization that we do have specialists. You know, at the beginning, I think we had a small, small and mighty team of folks. Everyone was willing to do everything. You know what I mean? Like there were maybe distinct job titles, but the expectation was that like, we were just going to get it done no matter what I mean. It's blurry in terms of people's like now we have several graphic designers we have several photographer videographers we you know what i mean like it's very very niche roles i think watching folks come in and maybe be a little bit more junior you know what i mean in their career and seeing the way that they blossom the way they can stride out which clients or accounts really like resonate with them. I think the three line for everyone that comes to our doors is that I think we were all like, like wannabe artists, but decided to do marketing because it was like a super vet, you know what I mean? In terms of like having a living. And so we're all really like deeply creative people and finding ways to like fuel that creativity and then watching folks see how, how much possibility there is in a small place, because even with more people, it's still a small company and so if you want to for instance a member of our team came in as an event producer has a theater background has built sets and things like that and they came to me two years ago before we started doing the brand activations and said that they wanted to not only start that as a service offering but then eventually be the head of brand acts for the company and i was like god i'm so like intoxicated by your ambition that i feel like let me see if i could sell some of these you know what i mean like does anyone buy that from us and then of course you could be the head of brand x whatever so just watching that sort of development and being able to meet like that was a dream of theirs and then yeah make it manifest and have it be a complimentary service that we're offering you know what i mean yeah maybe my most favorite part about this at this point in the journey but i do often feel like you know i'm the only one that's been here for 16 plus years i have one woman who's been with me for 12 of those years but oftentimes i'm like who the heck are all these people none of you guys i mean so much has changed since the very beginning yeah i'm the keeper of all all all that once was sure yeah yeah i'm actually curious what one what was like the biggest event that you guys put on and then two what's the one thing that you're the most proud of putting together these could be the same yeah the night market has become the biggest in terms of the total volume of attendees i am very proud of that because the impetus of it was sort of a redevelopment of that area of milwaukee's downtown and since we started that in 2014 that entire corridor has turned over in the most beautiful way and while we can't necessarily claim like a direct i guess causation like it's not like because we hosted the night market half a billion dollars of development went in there i definitely think there's a correlation and i know that we helped to like reshape the narrative about what it means to be there and i know a number of folks who moved in and have been a part of those development projects said that they saw the night market as like an early indicator that like like for crack and that you know i mean if you build it people will come and all of that and so i'm really proud of that like the transformation of that experience but also the whole neighborhood around it we've done things at bigger scales we started something called young professional week gosh maybe in 2011 or 2012 and that first expanded across the state of wisconsin and then nationally it's one of the programs that died during coven unfortunately but uh gosh that was so cool that i mean uniting young professional groups from across the country and seeing that everyone sort of had like similar struggles being able to sort of like be a support infrastructure for that that was really special and really cool the first time and actually that experience taught me that we didn't have to just work in milwaukee my initial sites were so focused on the city itself i it sort of like had me lift my head up and realize like oh wow we could do this anywhere there's nothing that stops from hosting things across the country and now yeah we do i would say about 40 of our work is not even in the state of wisconsin which is oh that's awesome that's awesome i did not know that that's cool i actually want to move into some things around like your philosophy around communities. I'm from Milwaukee and some of the things and just people like young professional communities and stuff. You have like this TEDx talk and so there's some things I want to talk through. You coined this term, maybe you didn't, but there's a term that you use called social architecture. Sure. Yeah, can you explain like what that means and how it shapes like the work that you do? Yeah, I think for a while, do you remember that like scene from Mean Girls like like stop trying to make fetch happen. We were trying to make social architecture happen as a modality for how we worked. And I think experience design now is maybe more fitting and it's easier for people to understand what Milwaukee does. But really I think the core of social architecture is a framework we use for how we design those experiences, which is that basically you need to be really intentional about the setting and the invitation and all the parameters around whatever it is you're trying to design if you want people to take action. And that honestly is, we have a very diverse client slate, but the main reason people come to us is the same. They have a product or a service that for whatever reason, their core, you know, ideal customer profile doesn't care about. And so they want us to help them come up with new ways for, you know, their brand to be elevated and be more, you know, acknowledged by that audience. And then ideally for them to do something, you know what I mean, to be motivated into action. And sometimes that's for commercial purposes, like, you know, to literally sell it to them. Sometimes it's because folks, you know, we work with like employer brands and they want people to come work for them. And sometimes it's literally, we work with municipalities. It's like, we want people to come here. You know what I mean? Like we are a place that we want to be a destination. And so those are very different types of clients I'm describing, but it feels the same to me. Like it's the same problem. We need to create an environment and intentionally design it in a way that people will care. I mean, everyone says the same thing like, oh, gosh, if only that audience knew, then they would dot, dot, dot, fill in the blank. And the thing that we advocate for is that they're not paying attention. But that's not an indictment of you or your brand. It's that no one's paying attention to anything. I mean, like we live in a very overstimulated time where there's many, many modalities of communication and everyone's sort of shouting into the void. void. And so what is it that we can create that'll maybe intercept them, particularly in a setting where they might already be rather than you shouting to the void, trying to get them to come over to you. You know what I mean? Yeah. What's an example of a municipality that was maybe a fun and interesting thing? Like, oh, I didn't know that the library had this or something like that. Yeah. Yeah. So we work with the city of Wauwatosa, which is a suburb of Milwaukee. And that has really, you know, very intentionally in the last five or six years, tried to position itself as like an artist community, both for artists to live, but also as just an artful place where the residents can sort of enjoy the benefits of that. They had us create a festival called Art 64, which is a two-day bracketed live painting tournament where the attendees decide whether or not they like the artwork and that advances the artist. And the finalist gets $20,000. Wow. Super fun. It's really dynamic. But it has in this last year generated like over $600,000 in sort of tourism, you know, economic impact for the weekend in terms of people coming in from all over the region for it. And millions and millions of impressions. in terms of the campaign really trying to, you know, have Tosa be something other than just a suburb of Milwaukee, which, you know, I think locals sort of think of it that way, but they want to stand out on their own. You know what I mean? And to be their own destination and have it be a thing that, you know, people are excited to go to Wauwatosa rather than saying like, oh yeah, I think I accidentally drove through that, you know, when I was in Milwaukee. For sure. I think there was like a statue that I saw or something. Yeah, exactly. Yeah, central trolling, you know. Yeah, yeah, some random thing. It was, you know, it's a fun problem. It's a fun problem to have a really fun solution. Next year will be our fifth edition of this experience. So it's a really cool, it's a really good example, actually, of someone saying, like, we need something brand new. And then us being able to kind of like help fill in the blanks about, all right, what are we going to do? How do we get after these like goals you have in a new and interesting way? Yeah, that's cool. With this social architecture conversation, you know, a lot of these companies, organizations, they're trying to figure out how to like connect with people and really like resonate with them and make them feel like, hey, you belong here or, you know, and so I want to go into this theme of belonging and how a lot of companies or communities, they misunderstand what that really means, looks like and feels like. So maybe talk about that a little bit and like how you've helped some people do that. I think that's really interesting. Yeah, I think especially in this moment where just feels like things are really, it's easy to feel othered. Like it's just kind of like a divisive and yucky time in a lot of ways. And that's sort of a political comment, but kind of not, you know, I just think like the, one of the yucky parts of social media is yes, you can find your niche. You know what I mean? Like whatever obscure thing you really like, like there is a place for you, but even in this sort of like segmentation, you're sort of creating like us versus them dynamic over and over and over and i think we see that in our society in a way that's very it's like very deeply troubling to me to be honest with you i think the antidote to that is a really intentional repeated because again people aren't paying attention so you need to remind them um warm invitation over and over you know i mean like that you're welcome here that this is for you that we want to see you it doesn't matter that you didn't see the first time we still want you to be here and you know what does that look like inside of a company versus like an external you know what i mean sort of like promotional campaign those things are can be very distinct and different but i think in spite of the technological boom you know what i mean and the like many different ways we can use to communicate me saying like hey jacob i really want you to be there like you know what i mean like there is some part of us as a human being and i would even say that it's like it kind of like scratches our fifth grade self like you can sit here you know i want you to sit at my table you know or whatever like there's some part of all of us that i think unless you're like maybe deep deep narcissist or whatever like that just wants to be seen and heard and intentionally invited so that yeah that's how feel like you belong like i'm supposed to be here they want me here you know what i mean this is for me also you know yeah it's it's like the whole thing it's a lot of times people think like oh if we do all this marketing like people will understand it and they'll appreciate it and they'll attend but a lot of it really is like that kind of like uh personal outreach like hey we have this thing coming up you know if everybody inter or invites like two to three people and extends the invitation it's a way different even as the person gets there they're like oh where's my friend or where's that person i know that i'm going to have someone there right now yeah exactly security blanket for like where am i going to sit you know yeah yeah because otherwise you're just i mean again because you and i have obviously put on different events throughout these there's always people that walk in and you can just tell they're just like there and they kind of stay on the edge they might get something to drink or the food but they're just like you know and what it really takes is for that one person in the room to recognize them and actually go up to them and say hey what's your name i think you should meet this person and you know i'm a deep i'm a very very uh deep introvert and so i feel like i can easily spot that person in a crowd and i know how to like resonate with them and make them feel like i see you i want you to be here let me maybe just help you like jump in the water because once you get in it's like the water's always warm you just need someone to like kind of be like come on come on come on come on yeah or like that simple thing like if the event's done and like hey we're actually going over here if you want to join us like that after after hangout thing too is because sometimes people see that and like oh i didn't get invited like i don't know i belong here exactly yeah the startup wisconsin podcast is presented by valency fund you build a company with real revenue you've got a growth plan but traditional bank loans and venture capital don't fit your business stage or model. 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And I know that's had a story in itself, but I do want to make a connection here where, cause you did new walkie and you're doing all these bespoke events and these experiences, but what, what was the connection between doing that you and like technology and software and startups and founders? Like, obviously there's entrepreneurship in within like retail and brick and mortar and the things that you were doing before, but how did like that, the technology and software world like how did that all happen for you sure well there's two little pieces of the story that maybe we glossed over the first is that after about 10 years of new walkie we spun up a separate company called nuance to do recruitment as a really a compliment to the marketing services we were offering and nuances icp were really startup like high growth startups that were looking you know what i mean like maybe they got around a funding and then needed to scale their team really quickly and you want to be a partner for that and so that really like was the first time i got maybe into the tech scene or became really keenly aware of it because it was who we were directly selling to and then i had a little baby dalliance in a b2b sas startup in the pandemic called rivet which was really supposed to be like the technological way of offering what new walkie had always done with like introductions based on personality that company still exists but i'm no longer involved on it day to day but between those two things i was starting to feel coming out of the pandemic when the world kind of opened back up like a little lonely to be honest with you like wait a second there used to i know there used to be a bunch of startup programming in the area but it wasn't it didn't really appeal to me before and now i feel like i'm a part of these other things and i don't like where are my people you know what i mean and so there apparently were a couple other people who felt the same way and so the origin of the founder community was just one party we hosted in august of 2021 really without the intent of making it a series but it was really fun and it was just we called it founder fest it was just founders telling their stories hanging out with other founders and to be honest with you it was a room like unlike any of the others i had been in i at that point hosted thousands of events out sure but it felt like oh this is for me this is like a group of people i really want to be around you know what i mean like really interesting dynamic smart creative clever people who have all done this same kind of crazy thing i had done which is like like leave it all behind and go out into the unknown with an idea and try to make it happen. And so I remember distinctly, like at the end of the night, we were sort of like cleaning up and people were like, when's the next one? And I was like, next one? I don't know. I mean, this was like a good time. Like, can we just enjoy the fact that we got to have this? And well, like there was a next one and the next one and the next one. And so in the last four years, that has grown to be a network of founders which has spawned outside of the city of milwaukee and to include folks from the upper midwest really i think because there's just not enough stuff like this and people are willing to drive last year we started hosting things in other cities just to be more cognizant of the fact that people were making a drive to milwaukee and we wanted to go where they were but gosh if it isn't still like my favorite little pet project there's a group of 12 founders who help to organize everything so it isn't it isn't just new walkie although i do dedicate some staff time to it because i think fortifying this network is really important beyond my own affinity for it i think it's a very important thing to have for the state of wisconsin for the broader economy here etc and so that i'm really grateful for it's a group that has evolved over time mostly because it is startup founders and wouldn't you believe it like well busy with their startups and so even that has been interesting to see i feel like there's been several sort of eras even in the last four years depending on who's in one of those leadership seats like they're the one whatever they're passionate about tends to be what gets created then but the goal is to connect founders to one another for a sense of like community and fellowship to capital when they are needing money to grow runs to customers so that they can scale quickly. But I would say the one-on-one connections I have with founders and the folks I'm... Mentoring is the wrong word because I see them as my peers, but it really is like this sort of like, okay, can you just help me? This just happened to me yesterday. I got a text from my founder who was like, I'm driving to a pitch. I just need to work out what I want to say. Can you call me right now? And so I was on the phone with him. I was also driving to a meeting and I was like, I have exactly 12 minutes. And he was like saying the pitch again. And I was like, no, you're missing the thread. Like you say it like this. You know what I mean? He was like, oh, thank you. Thank you. That's exactly what I needed. And then like we both went on, you know what I mean? With our dates. And I was like this, this little bit, like when you just need, you need like a little boost, you need the word of encouragement. You need someone to be like, no, you're right. You're screwing it up. Don't do that. That piece is something I wish I would have had access to when I was a baby founder, but it is very life giving for me, to be honest with you. Yeah. To be able to help other people on their way. And, and I'm curious to see where the group grows. I mean, it's all been so organic, we've had almost no funding for it. Which is crazy, which I that's something I actually was curious about is like, what, What do you think it would take to get like resources like capital to create like a stronger support system for it to keep elevating it and improving like the impact it makes? Yeah, I mean, I think part of it is that we needed to get serious about it being an entity. And we did that this year. We are now fiscally partnered with the Wisconsin Startup Coalition, which is great. Oh, nice. So we have like a formal structure that was needed before. I think, you know, I don't know. I've gone back and forth about like, what is the model for this? Because I don't feel great about charging founders who are resource scarce, like a membership being. Yeah, I totally get that. And so we feel the same way. You know, and it seems like the types of sponsors that care about this are immediately benefited by the group. So think like lawyers, accountants, you know what I mean? Service providers that would help. But I have been very judicious about who gets to do that because I don't want a bunch of people spamming this group. Like I just think they have to have the right mentality that this is really about supporting people who have taken this lifestyle on, have put all of their livelihood on the line. You know what I mean? And they just, they don't need to be spammed with the latest and greatest software or whatever it is. And so that story I think is still remains to be written. But what I have seen is that founders are really willing to help one another. And that part we have managed to scale and decentralize in a way that is very unique and surely has not existed in Wisconsin like this in the past. Yeah, for sure. Yeah, it was interesting. Again, just my perspective from Green Bay looking towards Milwaukee, seeing it start as a Milwaukee focus group and seeing it expand to Midwest and just seeing the things just starting to do Chicago. I believe Minneapolis recently, there was a partnership or collaboration there, obviously bringing Founder Fest to Madison and stuff like that. It's just been really cool to see it kind of like unravel and see just it grow and in whatever way it can grow with you know within its constraints and i i think there's something special about the way that it's that it's been built because like you said it's by people that our founders have like it's the it's not mentorship it's happening it's like trusted friendship it's like this really oh this is someone i can go to for advice and i can either listen to them or not but i trust like what they're gonna tell me exactly yeah so it's like different than like a someone on the board or like an advisor it's like hey i was telling you a group of folks a couple weeks ago about how as a founder you just have very few spaces in your life where you can express doubt because you're not going to do that in front of your team who's looking to you to lead you're not going to do that in front of your customers who have paid you. You know what I mean? You're not going to have your board or your investors who maybe also have a stake in your success. And, you know, at least for me, I've always been the breadwinner for our family. My husband opted to stay home and help raise our children while they were little. And that was a decision we made. But that means that like, I don't always want to put any extra stress there when I have doubt. You know what I mean? And I have a very incredible supportive husband and I a hundred percent believe that he would be okay with hearing that, but it is a pressure. It's a pressure unlike any other to feel like you have to shoulder that. And not everybody has a co-founder or someone who's at your same level where you can be like, I don't know, man, is this going to work? I hope this works. I hope we make it. I mean, I hope this is the right decision and create a space where even if you're in a completely different industry, you know that you have that as like a tie that binds you. I 100% guarantee. I don't know if this crop of founders that are in the group, if any of them are going to be some runaway unicorn success, but I know there will be a ton of positive impact on our slate. because this group of people has someone they can call. You know what I mean? Have someone they can call. And sometimes it's all you need to hear is like, no, no, that's right. I got this. And then you just keep going. You know what I mean? Yeah. That I'm really proud of, excited about and curious, like, okay, what's next? Where are we going? Yeah. And like, how do you, I mean, cause I'm sure there's a party that's like, oh, I would love to spend more time energy on an MFC, see, but then you also have these two other businesses still functioning. And so like, how do you think about balancing that? Like, do you ever see yourself not running new walkie? Do you ever see yourself, you know, is that, have you ever thought about that at any point, like exiting, like, or handing, handing off leadership to other things or just, yeah. A business partner for 15 years, decide that he was done at the end of 2023. And that, was a shock to the system to be honest with you and it really made me think like oh gosh am i done should i be done you know what i mean like he wants to be done and it was a clarifying moment for me like no this is still my favorite platform new walkie i mean you know what i mean like my favorite platform to build from the place where i feel the most creatively satisfied i still love leading this team and like i said watching them grow i feel really inspired by our work so i don't know that i'm going anywhere in terms of how do i balance it i don't know it's like whatever the fire of the day is you know i feel like i promise to sort of like scan the horizon and figure out like who needs attention i mean part of that is like i don't run nuance day in day out my partner orlanda daring does and we have an incredible team that does the actual work similarly with new walkie like i don't we have people who manage themselves which is a beautiful thing yeah and so i don't have to be down in the weeds in either of those places i think the maturity and the life cycle of those businesses allows me to have a passion project like mfc go awry in some ways because i have extra capacity in this moment and like i said i don't do everything for mfc either I mean, we just have people who are each willing to volunteer and chip in and do more. And always, I mean, every day we have new people come into the fold who are like, I want to get involved. And so at this moment, I feel like we're just kind of riding that wave. And we'll see. I mean, like I said, I've been a part of a number of other startups. Like, I don't put it past myself to think that, like, these are the end of, this isn't going to be my final three stories. I'm sure something else will happen. And my husband has a small startup as well. And so I've been watching him be a baby entrepreneur the last couple of years now that our kids are older and in school. You know what I mean? Like he's really starting to stride out. I've been trying with all my might to not get involved over there too. Oh, yeah. Totally. Yeah, yeah. Always have good advice, you know. Exactly. Happy to give it, but I wait till I'm asked for it. Yeah, yeah, yeah. Because otherwise I feel like, you know, it's not, that one's not mine. That's his, you know. Yeah. Yeah. Yeah. And something I think about as you're sharing all these things is that, you know, especially with like the founder community, you like doing the work in your business, growing businesses like that is value to these other founders. So like it's weird, like if you were to say, you know, for example, like I think about myself, I've never been a founder myself. I have an entrepreneurial mindset in my work, in the job that I do, but I've never built a business and launched and scaled something and had a full team of my own and all those things. So I can't like offer advice or share a personal experience. I'm not that person. And so like the best thing I can do is just in make those introductions. And, and so I think like for you, like the value you add is by staying where you are and in the weirdest way. But I love that you're like, you know what, like, it gave me clarity because I realized like, oh, this is like really fulfilling for me still. Like this is where I'm supposed to be right now. And I wonder if like a lot of entrepreneurs like ask themselves that question enough, like every year, like do you really do they really ask themselves, you know, how often have you reflected about that? Like, oh, is this, you know, where I want to be, but it took that that trigger that moment of that person leaving the business to be like, what do I want right now? Like, is this what I want? No, it's interesting. I definitely can run away from you, especially when you're like grinding it out and you get really fixated on whatever problem you're solving. Yeah. I started this when I was 23. So I really didn't have a lot of previous work experience. And I think what that has colored my worldview with is the idea of agency. I feel a lot of agency. I feel like I am choosing everything that's in front of me. And that is something that comes up that I don't like it anymore that I can choose again. You know what I mean? Like I don't have the same choice. I think there are consequences for those choices. It's not like every single one of them like ends up being a raving success or monetarily fruitful. but I, I feel like I've done this long enough to know that like I'm in the driver's seat and actually my, my sole role as the founder and the leader is to stay clear eyed in that no one else is going to be looking around the corner for what the next opportunity is. That's what my job is. And so I don't know, I don't know if most people have time for that kind of reflection. I, you know, I tend to be sort of an introspective person and I tend to have a very low bar for dissatisfaction. Like I'll be the first one to say like, Oh, we're never doing that again. And I don't care. I mean, like, I think a lot of people really default to like, well, it needs to be a perfectly arced like narrative or what we did last year needs to be something similar to what we do next year. And I don't feel that way at all. Like, I just think it can all be new, but I mean, that's even in our name, new walkie. Our mission is to make new possible. I just think that's my like personal worldview you know what i mean that yeah nothing has to stay the same ever actually yeah it never actually does like if you think it does that's your own sort of like inner fear about the fact that things change always and always yeah yeah it makes you think about there's some quote at camber like who wrote it but it's like it's not the same river and it's never the same man like when a man steps into it because the water is always changing the the person's always changing yeah he's always changing right like people in the city are changing it's so everything's new even if we realize it or not so right yeah i do want to move into just milwaukee as an as a startup ecosystem and your perspectives on it like what do you think's like going really well right now like it feels like there's some high energy going on this month as we're recording this is wisconsin tech month but i also know that that's not the thing that's going on there's like nvng just had their their um their adventure summit or i can't remember of it but there's it just feels like there's a lot of things going on and there's a lot of energy in that region and so i'm curious like what your perspective is and how you're feeling about it right now yeah i do feel like there's more i would say there's more collaboration than ever before i can remember a time when people who did things in and around supporting startups felt, I don't know, a little edgy or there's some, maybe some pointed elbows. And, um, in some ways, I, I, I think the fact that MFC has arisen and we've been very strictly like, we're not an organization, we're just a network of founders. You know what I mean? Like, so as we've sort of been like a neutral ground to come play together rather than, um, needing to carve out our own, I don't know, territory in some way. Like, I think that is really interesting. The other thing that is curious to me is how the geography lines feel blurrier than ever before. Like we're doing something this week down in Kenosha and the week following in Madison. Like, I think there used to be these like clear, like, this is what it means to be a Milwaukee founder. And now I just think Like post COVID, what does that even mean? Like you can work anywhere. And even if you are here, if your co-founders in another part of the country, does that make your startup a Wisconsin startup? You know what I mean? Like the rules of all that have been sort of upended and there's a willingness to sort of seek out whatever it is you're looking for from the founder's perspective and not wait for it to be built for you. And so I'm very enthusiastic about this moment in time. I think, you know, we sort of go around and round around, like, is there enough funding? Are there enough good ideas? You know, that sort of like chicken and egg thing that still is a pervasive sort of issue, I would say, in general, my critique is that founders here tend to be the ones that are willing to take more of a risk compared to the investor class. class. Like I would say most investors here want to invest in what feels like a sure bet. And I think in order to get that revolutionary new technology, the thing that's going to seismically change our culture, our lives or whatever, how we work, you need an earlier bet on something that feels like it isn't a part of, it feels like it's on the tail end of what, you know what I mean, what is expected. And there aren't a lot of precedented examples for it. maybe that's sort of a cop out, but I sort of laid the blame there on the investor class here. Like we don't have many investors who are willing to place a bet on something that feels fringy. And I just think like all the innovation, all the disruption, all the things that, you know, you can think about products or services that have changed the economy or our lives or whatever, they were all fringe. They were all fringe. You know what I mean? And so, um, and that's, I guess maybe I'd say investor both in the classical sense. So like banks wanting to give loans, VCs and angels wanting to dole out, you know what I mean? Like equity and also customers. I mean, the number of like enterprises here that I think could be early customers, but don't want to take a risk or create a sandbox outside of the compliance space that would allow someone to like get a toehold in, have some real examples, have some real real customer feedback and grow, that's going to hold us back. Like it just will, like we're only going to, it doesn't matter how much enthusiasm there is, like without those things, you know, I think we're always going to be kind of like in the middle or in the bottom 50, you know, as a state when it comes to this stuff. Yeah. Yeah. It's interesting. I feel like there's definitely a lot of organizations, whether financial or not, that could have more sandboxes or a sandbox, They don't have them to play financially because it's like they probably have the capital to do it. And obviously, if they're privately owned businesses, they can do what they want. But the one thing that we know is true that we've seen and heard stories is that there's entrepreneurs that when they build a business and grow it where they live, it impacts the community like in multiple ways. A hundred percent. So like if you're able to, again, there's obviously it's risky to do venture capital or anything like that or angel investing. But like the returns are very clear when it works. and the numbers, you know, hey, it's an 80-20, like the 20% of the investments make up for the 80% that didn't make it. And that's kind of, as long as you're doing your due diligence in your research of the potential of the success of these businesses. But I think a lot of times I think about, you know, again, I don't know what it would take, but if you had like a credit union that's more localized and they were like, you know what, we're actually going to build a fund and we're going to invest in entrepreneurs in the communities that we serve and we're going to give them a chance like well i'm not gonna lie to you my ultimate vision is that we sort out a way for this mfc to have their own fund long term because i just think it's going to take founders who understand that risk and who have been through have a higher risk tolerance to do it i don't have any faith in any of the current institutions to come around and to lower the risk tolerance i just don't think that'll be what happens sure that's a good point yeah but uh yeah i was i I'm always thinking of like, why doesn't this exist or that exists? It just seems. And again, for the last 100 years, the technology entrepreneurship wasn't really a trend in Wisconsin because it was more manufacturing, which was technology at the time, just more physical. You understood. We had our boom in the 1880s. So we've been waiting for the next one. Yeah, yeah, yeah, yeah. You know, so yeah, I think it's just fascinating. I think it just takes and maybe it is just one of those things where it takes for the right people to be in the right seat at some of those organizations to be like, Hey, no, this is like what we're going to do. We have a team here that's going to actually know what they're doing and do it effectively. But I do think it takes like someone, you know, like yourself or the team at MFC to say, Hey, we're going to build a fund. And it's all going to be, we understand the risks and we understand the opportunities because we know like where to play and the right questions to ask, you know, it's like, or the connect and it's like, it's also the connections, the distribution for pilot programs and stuff. It's all connected. So, and then, and again, it just ties into the mission that you have is connecting these people, connecting them to capital, connecting them to customers and opportunities. And so I think that's awesome. And yeah, and, and from, from my perspective for Startup Wisconsin, it's such a great thing to add your events to the calendar or the things that you're doing for our calendar to create more visibility around it. So I just want to say, as we kind of wrap things up, thank you, thank you, thank you to you and everyone else. I know you're not the only person doing all this stuff, but you're a part of it. And I think, you know, your event expertise and just being involved in the Milwaukee community for so long, all those connections they have are help enable like MFC to keep moving and growing and, and all that kind of stuff. So yeah, so incredible. But yes, it is a team effort and I am really, really proud of it. So yeah, we'll keep going. We'll keep going. Don't worry. Yeah, absolutely. Thanks for joining us on the Startup Wisconsin podcast. Want to support the show? Don't forget to subscribe and get updates. If you're feeling generous, you can share, rate, and review our podcast to help others find us. All right, folks. Until next time, let's keep moving Wisconsin forward.

Angela shares the story of how NEWaukee, initially a social club for entrepreneurs, evolved into a thriving agency and a leader in fostering Wisconsin’s startup culture. She discusses the creation of the Midwest Founders Community (MFC), a decentralized network connecting founders across the region, and the inspiring work of elevating the Wisconsin tech scene through collaboration and mutual support.

From building a brand agency to leading an influential community of founders, Angela reflects on the importance of connection, mentorship, and a culture of belonging. She also shares the challenges of balancing multiple businesses and how she's helping others navigate the ups and downs of the entrepreneurial journey.

Tune in to learn:
How the Midwest Founders Community connects founders to capital, customers, and fellow entrepreneurs
The role of brand activations in building meaningful relationships within a community
Insights into the challenges of Wisconsin’s startup ecosystem and why it's crucial to foster risk-taking and innovation through community support

Jump into the conversation:
(00:00) Introduction
(03:50) NEWaukee’s social club origins
(04:49) Discovering revenue models
(07:22) Night market's staying power
(13:15) Proudest project expansions
(15:28) The social architecture concept
(20:21) Belonging through warm invitations
(25:17) Midwest founders community building
(26:17) Finding the right founder crowd
(28:22) Growing beyond NEWaukee’s boundaries
(29:55) Real-time founder support calls
(31:07) Funding and sponsorship challenges
(33:54) Safe spaces for founders' doubts
(42:14) Milwaukee's startup ecosystem pulse
(44:30) Risk, capital, and customer sandboxes
(47:30) Vision for a founder fund

Connect with Angela Damiani: https://www.linkedin.com/in/angeladamiani/
Check out NEWaukee: https://www.newaukee.com/


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Startup Wisconsin is the statewide hub for founders, investors, operators, and innovators. We're on a mission to connect and grow Wisconsin's tech and startup ecosystem.

Since 2017, our mission has been to connect, educate, inspire, and grow tech and startup communities across Wisconsin. Helping people find events, resources, capital, and each other. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.