Breaking Barriers: Kesi Milligan’s Journey as a Change Maker in Commercial Real Estate

Welcome back to WIRED: Stories of Impactful Women, the podcast where we shine a spotlight on the trailblazing women shaping the future of commercial real estate, business leadership, and beyond. In today's episode, hosts Heather Luce and Kimberly Downs sit down with Kesi Milligan—a dynamic commercial real estate broker, community advocate, and the first nominated guest on WIRED.

Kesi takes us on her inspiring journey from radio intern to residential agent, her pivotal role at AltCap supporting underserved entrepreneurs, and her determination to become the representation she wished existed for minority and women business owners. With honesty and humor, Kesi discusses overcoming fear, the importance of authentic connections, and the drive to be a change-maker in Kansas City's urban core.

Whether you're an entrepreneur, aspiring leader, or looking to carve your own path, get ready for a candid conversation packed with real-world advice, resilience, and heartfelt stories. Plus, discover how the power of mentorship, community, and a little roller skating can keep your cup full—even on the toughest days.

Transcript

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Every time I think, why am I doing this? I'm broke, I'm scared. I don't know what I'm doing. And when it gets right at the difficult moments where you think you just can't take it anymore, that's when the breakthrough comes. I've been doing all these things, and I already knew what I wanted to be doing. I just wasn't actually doing it. It is fear. You don't realize it's fear until you're on the other side of it. You are courageous because you're doing the things you're afraid of, the things that you know you can do. You don't have to be courageous to do. Yeah. Welcome to Wired Stories of Impactful Women podcast, where we spotlight bold, brilliant women shaping the future of commercial real estate, business leadership, and beyond. I'm Kimberly Downs. And I'm Heather Luce. We're the voices behind Wired. That's Women in real estate Development and your host for honest, empowering conversations that go way beyond buildings. Every other Wednesday, we sit down with women of influence, entrepreneurs, innovators, and change makers to share their stories, insights, and the unfiltered truth behind their success. So whether you're building a business, growing in your career, or carving your own path, you'll find connection, mentorship, and real world tools right here. This is Wired Stories of Impactful Women podcast. Hello and welcome back to the Wired Stories of Impactful Women podcast. Today we have Kesi Milligan, my friend and another Wired member. Kesi, we are so glad you're here. Thank you for your time. Thank you. This is also exciting because you're our first nominated guest. So Susan Scott, our friend and Wired member, nominated you and thought that it would be great to have you on here. And I couldn't agree more. So thanks for being here. Tell us a little bit about who you are, what you do. So, my name is Kesi Milligan. I'm a commercial real estate broker at Select Sites LLC here in Kansas City. And I have a background in urban development, neighborhoods, and residential real estate. But now I'm a commercial broker. Yeah, you started your career in radio too, right? I did. In 1999. I interned at Carter Broadcast Group, and then one day, one of the radio announcers didn't come in for the shift and I was forced in front of a microphone and. Talk about getting it done. That's awesome. I guess this is what we're doing now. No, that's awesome. Well, you've been licensed for quite a while. How did you go? You started in residential, right? And Then now you're a commercial agent. So how did that career path happen? So I've had a license in real estate since 2004 and here, not so many years ago, I went back to school for urban studies with an emphasis on community development and housing. My adjunct professor at that time was Ruben lonzo. He's the CEO of All Cap. So after graduating in 2019 December, I was looking for employment and Ruben put a post out on LinkedIn. They were hiring for a business development officer. I applied, he said, sure, be great. But then in that role, doing small business loans, I realized there were so many minorities coming through getting capital to build out a commercial space, buy commercial real estate or invest. But I really wasn't sure, you know, who they were using for an agent. Come to find out, most of them were not using a broker to help them find the location for their business. Fast Forward went to a Realtor symposium put on by UMB bank and one of the speakers mentioned that a lot of the small incremental developers were not getting the capital they needed to move into commercial because their portfolios were fully residential. So Fast Forward, I thought, you know what, I need to be a commercial real estate broker so I can help all these people. And here I am. Yep, awesome. So backing up real quick. So altcap, I love this organization. So can you tell us a little bit for people that don't know who they are, what you did there and kind of the whole premise behind that? Absolutely, absolutely. So AltCap is a CDFI, that's a commercial development financial institution. And what their role is is they are put in position to get capital out into disinvested communities, maybe startups, maybe you started your business and you're in that zero to three life, zero to three year life cycle and you need capital and you can't find it anywhere else because a bank typically will not look at you in that zero- traditional sense. traditional sense. And so, we were able to help a lot of people and they're still doing great work. I keep in communication with them, but yeah - small business loans all the way up to $350,000. Man, I've helped so many people. I'm glad they exist becuase it's needed. Yeah, it's helping underserved business owners, underprivileged business owners. Right. And helping them climb the ladder just like anybody else. So I think we originally, originally met when you worked at altcap, maybe. I was trying really hard to think about this and I have a bad track record of remembering how I know people, but I think that, that you were in that role. And then we started to see each other around Uli then started to see each other around Wired. So it's been fun to see you kind of evolve all these years, but I've always been a fan of that organization, so I love that you're a part of it. So let's talk about. You worked at AltCap, they hired you. You basically recognize that these business owners that are getting the, and doing the deals, getting the projects done didn't have representation in options of having, you know, like a broker to help them throughout it. So they're forced to kind of do it on their own. Right, right. So what was that like seeing that? And then also what drove you to say, I feel like I could help them You know? first of all, when I heard that a lot of small incremental developers cannot get additional capital to do more residential projects because their portfolios were too risk averse and they needed more commercial in their portfolios in order to get higher lump sums or higher dollar amounts of capital. So I thought, who would I refer an individual to for assistance with commercial. That is culturally sound. So what I mean by that, I saw a lot of minorities, black and brown individuals coming in, business owners looking for capital. There aren't a lot of black and brown commercial real estate brokers that I could have referred them to. No, there's not a lot of women. There's definitely not a lot of people of color. Yay, Wired. And so I said, you know what, if, no, if I can't think of someone to refer them to, then I need to take on the challenge. And so from that point on, I sought out one of the persons that I thought could give me the best advice, and that was Cheryl Vickers. And so after speaking with her, having the opportunity to talk to her briefly about it, she gave me some sound advice. Right. She said, hey, if you're in residential, you probably want to exit that scenario and get with a commercial outfit and then find you a mentor. And so I reached out to Susan Scott after forming my own commercial real estate brokerage. And it's history. Yeah, there you are. You knew Susan, though, from years before, right? Yes. Long story short, 2004, when I got my license, I maybe about a year into that, I ran into some folks that wanted to get another retail space for their business. And I was referred to Susan back in 2005. And I just never thought that I would be reaching out to her almost 20 years later. Right? Wow. Yes. Way the circle comes back Around. Yeah. But again, it just goes to show, like who you know and who you're connected to and just keeping those connections because you never know when that person will be so influential and become your Mentor, you know., I was like, susan, please help me. She's like, sure, yeah, she's awesome. So I believe it. I love Susan. Back when I was working or asked Susan to work with me, she was with Greg Patterson and Associates. They had a lot of the urban core market sold up as far as commercial real estate was confirmed concerned. And so I thought she would be the best person that could assist me in being culturally sound because she did a lot of urban core work. And come to find out we know a lot of the same people. Yeah, We're not that big of a city. Yeah. I've always known her even before we became friends. Like, I've always known her as a midtown, you know, work. Like she works the midtown urban core area. And it's cool to know that she's been around for so long to see not only the changes, but also people come and go in that industry. And she's always been an advocate for getting more women, more representation of all kinds. Just, you know, that's just how it should be, so a lot of representation for, especially for small entrepreneurs coming up. She loves to support. That's my background in neighborhoods. I do a lot of the ground up advocacy work for policy change. And so I just love Susan and I'm grateful to be a select sites because Sheryl Vickers is awesome too. Yeah, it's fun that you're. Yeah. You guys get to work together all the time. I always think that office would be so fun to work in because all my people are over there. You know what, we try to work when we're in the office, but it's a lot. Sometimes it's too much fun. Sure, sure. It's awesome. So I, Heather and I talked a little bit before we, before you got here and we were talking about one of the things that I've struggled in my own business is I'm not very money motivated. And she mentioned that when you guys were talking about coming here, that being rich isn't the motivating factor for you. So I know some of the issues that I've had trying to make sure that my thought process is right. But how do you stay motivated then if that's not your motivated motivation? Well, I just understand how challenging it can be for one, to be a small business owner, number one, to be a person of color, number two, and then from my standpoint, to be a woman. And so I feel that there's never too many. There's never enough advocates for people that run into challenges that, I hate to say it, that are kind of systemic challenges. And I believe that somebody's got to do it. If not me, who? And you can't let money be the driving factor if you want to actually make a difference. And so I pride myself in focusing on being a change maker. And if I'm chasing a carrot, then I don't think I will accomplish that because I will only be giving just a portion of myself to that individual that needs my help. And I like to go beyond just the transaction. Right, right. An entrepreneur needs more than just a space. You know, they need entrepreneurial support organizations that they can go to for mentorship or opportunities to market their business or get accounting advice. So I'm just about the whole person, the whole entrepreneur, and not just the fact that they need a space. Right, right. So you're clearly pouring into other people all day long, all the time. What do you do to pour into yourself? I love movies. I love watching movies. And so if I could just watch movies all day, I would. Or play music. Play music and. But I'm taking up roller skating now. Ooh, there you go. That's fun. I know. So I recently had a birthday in August, and I. Nobody would go with me, but I went roller skating, and so that's my new thing. I love. I was telling Heather, preparing for this podcast that I love doing things that are challenging. If it's easy, I don't want it. Yeah. Yeah, I don't want it. So how's roller skating going? Girl, When I videotaped myself doing it, I noticed how I was just. I was, like, breathing, like, taking. I was out of breath. I was like, oh, my gosh. Yeah, it's a workout. It is a workout. Yeah. We go to roller derby. Have you ever been to roller derby? I remember you telling me that. That is so exciting, though. It is Awesome. It is so cool. Those. Those women are, like, very badass. Like, and it's really cool to watch them not only play the sport competitively and aggressively the way they do, but on wheels with shoulder pads. With shoulder pads in the quick circles. No, it's fun. You gotta go. You definitely gotta go. I'm not brave enough to. To do that. Just watch it one step at a time. When roller skating becomes too easy for you. then you'll become challenged. And I'm going to go with Heather. Yeah, you should. We should. Yeah, that Sounds fun. So one of the questions that we've asked a lot of women that have come into our podcast is one of the things that we've seen is they'll start somewhere and that gets them started and they go somewhere else and then they go somewhere else. So as you have pivoted from one industry to another, I know they're all connected in one way or another. What is one of the biggest challenges as you had to make those pivots in your own life? Well, I think relationship management, I think, was really one of the main things that I realized that I was not as good at as I could have been. I've worked in some great places, done some great things with some great people, but you have to reach back out. You know, when you transition and transition, I've transitioned several times. You have to reach back out and then, then find that middle ground where you can still reconnect. And I've been blessed to have the capability of doing that. And I always bring my past experiences with me. Right. When you, you have to present your whole person. Right. Everything we've gone through in our lives, I'm sure we'd love to leave some behind and take only the good, but you have to, you have to take all experiences, move them on to the next challenge, use those as opportunities to grow and learn and. But yeah, so right now I'm starting to reach back out. I had a, like a 11 year career with Aflac and see, that's a whole nother story. Yeah, that's another episode. You know, I opened, I don't know how many, worked with countless entrepreneurs and business owners. And so just going back and saying, hey, how you guys been? I'm doing something new, so it's. I'm blessed. Yeah. That's awesome. That's amazing. That's just. I think we, Even now, as I get older... I think to myself, I'm like, you know, I, I'm constantly seeing things that women are doing and they're like, you know, somebody will say, you know, hey, I turned 55 and I started a new career also. I think in today's world, so many times we think, oh, it's too late, or, you know, and hearing, you know, the changes that you've made. And yes, you said they each kind of were stepping stones, they brought you somewhere else, but you still were able to make that change and start fresh somewhere and start a new, you know, adventure. Well, it's scary, I would say, but I get bored easily. Right. But a Good friend of mine, Terrell Jolly, he told me to stay. TJ yeah, Good advice from that guy. He told me. And, you know, every time I think, why am I doing this? I have. I'm. I'm broke. I'm. I'm scared. I'm. I don't know what I'm doing. Why did I even make this change? And I want to go. Like, I'll just go get a job. Forget it. And then tj I could hear him, you know, him and my mother stay. You know, just stay. And when it gets right at the difficult moments where you think you just can't take it anymore, that's when the breakthrough comes. And so I feel, you know, when they say it takes three years to kind of break into this business, you got to have some staying power, and you've got to really want to make a difference in somebody's life, especially if you're going to go with very limited financial resources for quite a long time. So that keeps me motivated, just knowing that if I stay long enough, I'm going to change some lives. And so I'm okay with that. Yeah, it's an uphill battle, isn't it? Like, as you're trying to build and just stay in the course and just trust in the process is going to work out. So you kind of talked a little bit about it, but what keeps your cup full? Like, what do you do for fun? You said you obviously roller skate. You play music. Like, you play musical instruments or you listen to music. Well, I played a flute coming up, but I. I mostly listen to music. I like DJing for myself, so I have, like, little mini parties at home, and then my son. And then we lip sync. And so. And I would probably be really embarrassed if I told people my. What relaxes me is cleaning. So don't let. It's a good thing. It's a good thing. As long as it's not, like, super unhealthy cleaning or you're obsessed. It's a good thing. And I clean, and then everybody in the house, that's when they disappear because they don't want me to ask them to start. Join your party. Your weird party. We're gonna be asked to join this clean party. I'm out. You know, in preschool, I've worked with some young kids, and they have that cleanup song, it's time to clean up. They're like, no, yeah, don't even sing it. Don't even hum it. But no, I'm highly active in church. I do volunteer work with Blue Hills Neighborhood Association. I still work with UMKC, with Dr. Jacob Wagner and Centers for Neighborhoods. So I'm very active in the community. Have a youth group that I work with during the summertime. I mean, I'm all over the place, probably a little too much, but you know, I get bored way too easily. Yeah, no, it's good. And it seems like you're filling your time with very positive things that, you know, helps other people too. So I love that. Do you have any advice that you would give to women looking to either grow their commercial real estate career or just any entrepreneurial venture they have? Yeah, well, don't over educate yourself or think you don't have enough. And it took me going through all of that to realize, you know, we're used. I was using education or thinking I needed more education as a crutch to not start or not to transition or not to go to the next level. Fear. I've been really struggling with fear. I struggle with the imposter scenario thinking that, you know, they're going to think you're stupid, like nobody looks like you, you know, all the. All if it's, if it was negative, my brain was telling, you know, have singing that song to me. And so sometimes you, when you hear that, just know that something good is on the other side. Right. And sometimes our body is trying to protect us, but we don't need protection, but our brain thinks it needs to jump in. I would just say let fear be your North Star is weird because once fear starts to set in, that means you're closer, right? You're getting closer to what you're trying to accomplish and never be afraid of success. And I think that has kind of held me back a little bit. A fear of success, thinking, oh man, if I, if I do good at this, people really gonna expect me to, you know, to, to be responsible or, you know, you know, sometimes I just like to go off on my own. But I think let fear guide you and let that be an indication that you're getting closer to what you told yourself your real goal is. And don't be afraid. And then if you are, reach out to some folks to encourage you. Yeah, absolutely. It's funny you mentioned tj. He actually gave me some advice on that topic. I'm. He's so generous with this time. And I had seen him around and we had so many mutual friends that respected. And finally my commercial banker said, you know who you sound like whenever I was talking about kind of my goals and my dreams. And she said, terrell Jolly. And I was like, why does everybody keep telling me about this guy? Like, what is this? So I had lunch with them and he just listened to me for a while. And finally he's like, just, you need to stop going to all these trainings and all these programs and just do it. You already know what you're doing. Just do it. And I was like, but I'm signed up for. I have another one that starts next week. And I realized, like, because I had been doing like, Small Developers of Kansas City, Incremental Developers, Small Scale Developer Forum, uli, the Urban Urban Land Institute stuff, and I'd been doing all these things and I already knew what I wanted to be doing. I just wasn't actually doing it. And so it took him, an outside person who I really respected and looked up to, to be like, okay, you have enough training. Like, go do it now, you. And then you always hear it. Wired, they're always talking about owning the fact that I'm not a aspiring developer. I am a developer. I am, I do this. I am an investor, not I want to be an investor. And so just really like holding the mirror up and saying, like, okay, I am actually doing it. I need to own it. And so I completely. That resonates with me, the whole, don't over educate yourself. Because I think that it is fear. You don't realize it's fear until you're on the other side of it. But it is just like, okay, well, I've already done this. You know, I built this for me. I built this brokerage. It's doing what it's supposed to do. I know what I want my next phase of my career to be. I know how to do it. So just do it, you know? And it took somebody, an outside person that I see as a mentor to really, like, tell me to do that or give myself permission, I guess, I don't know. But it is just leaning into our own again. As women, we talk about this a lot. We all have intuition, right? That's the superpower. And just leaning into what we know is the right thing to do. And if we don't. Kim, you've said this before. If we don't think that we know how to do it or how to do it, like we have people around us that do, and so leaning into those people as well. So I think that's really good advice to just dive in, you know? And that's what Wired provides, right? Sure. I mean, that's the whole premise of Wired. Right? And so I, I applaud Audrey and Sheryl for creating that. That organization. Because when Susan invited me, I was like, oh, my God, you got to join this thing. Oh, my God, it's great. You gotta come. I was like, yeah, yeah. And. But when I. When I showed up to the first event, it was like, come on in. And it was so much knowledge in the room and just to see so many women come together, because a lot of times, you know, a lot of women can be a little. But when they, When. When you understand that, that's all left at the door. It's all about love and supporting and uplifting and empowering women to let them know that, hey, if you see a man can do it, you definitely can do it. And more than likely, probably a little bit better. But having all the resources in one organization, that if I needed anything thing, I know I could just reach out to that organization, to the group of women and say, hey, you know, can you help me out with this? And because you are a Wired member, they're like, sure. Come on. It's like a sorority, right? Yeah. Yeah, it's definitely. People are so generous with their time and their knowledge in there too. And I. When I think about Wired, I think it's so wild that people who I have known and respected in my career, coming up like that, I consider mentors, whether they know it or not, or I've actually met them or not, are now my friends, which makes them even more my mentor. But also, I just know this personal side of them as well. And so it's really an incredible thing. And it's helped me grow so much in my career and really know where I want my path to go, so. And we just do cool stuff like this, so I'm grateful for it. What about you, Kim? What is. How does Wired? So I was that person that Heather, you know, was like, you need to come. And I'm like. It'S not really for me. And I'm like, well. And not realizing that. That I did. She was. I said something about, well, I don't really own any commercial real estate. She was like, don't you own the building that your mortgage company runs from? And I was like, oh, yeah, I do. I think you qualify. Yeah. I was like, oh. So I came probably a year ago and then just recently joined. Just timing a year ago was kind of off. And then finally was like, okay, I'm going to do this, you know, and for the same thing. One of the reasons I love, love Wired and just networking with women in general is just that Tribe and kind of like you said, I loved your authenticity. So I appreciate that about just talking about. I think a lot of us, we see social media, whether we're listening to podcasts or we're just scrolling through, and we see women from day to day, and we don't always see that side where they're like, I have a day where I'm afraid, or I don't take that next step because of fear, or I woke up this morning and the imposter was on my shoulder, and I listened to it all day long, and I just couldn't get where I needed to be. That. That's real, you know, and so being able to relate with other women and say, man, that was me today. And they're, you know, they kind of. Look at you and go, oh, I. Didn'T, you know, I didn't know that you think that ever. Or it's them being able to realize that person has those days and they're still where they are because they had courage. Which I always told my kids growing up, you are courageous because you're doing the things you're afraid of. You're not courageous because you, you know, you can do them. You're doing things that you are afraid of. The things that, you know you can do. You don't have to be courageous to do. Yeah. You know, so I think I just. I appreciate that authenticity because every time women are. They feel like they can be authentic and say, wow, today sucked, you know, or I didn't want to get up this morning. I didn't want to do my job, you know, because I felt like, oh, my goodness, can I even make it through today? Because of X, Y, and Z that we all have those days. So I think wired, other women groups that I'm a part of and just the women that I, you know, invest in that. Invest in me. I think, think it's just that having the people that say, yep, get up. You can do it, you know, or, okay, don't do it today. Spend all day taking care of yourself. And at the new pool spa thing that I love, we. We recently went to Clay Sanctuary and down in the West Bottoms, and they have a bath house spa where you can pay to. There's what, a float. There's a steam sauna, a rit dry sauna, a float pool, hot tub, cold plunge. Yeah, it's really. It's pretty good. And my favorite was the salt shower. And the salt shower. Scrub your skin with Himalayan salt. Yeah. But it's good, and it's good self Care to go there and to just turn it off for a second and spoil yourself for a second and enjoy it? There's a beautiful tea room attached to it. Coffee shop, tea room. Oh, man, it's stunning. And everybody that works there was great. So highly recommend. Treat yourself, because you never know when you're gonna get it from somebody. Yeah, yeah, for sure. For sure. And we work so hard. We deserve that. You know, I just. My thing when I leave the wired events or really hanging out with any wired women, I feel so energized and so just confident and like I could take on the world, and it. It hasn't gone away the entire time I've been here and been a part of it. So is there anything fun coming up that you want to promote or you're looking forward to in your life or. Oh, I'm looking forward to Christmas. Yeah. Holiday season. I think what I love about Christmas is not the fact that it is Christmas. I think what I like is that everybody is just extremely nice to each other. I mean, it's always like, we all have a mission to be extremely kind, extremely thoughtful of others, and I think I love that part of year. So I'm excited for Christmas. Good. You're skipping right over Halloween and fall, but okay. Because I'm a scaredy cat. Yeah, I am too. I was thinking about haunted house this year. Oh. Did you know that the Beast is one of the. It's one of the oldest, if not the oldest, haunted house. Really? I didn't know that. In Kansas City. That's cool. And we have, like. There's so many down there now. Isn't there, like, five of them or something? I don't know, because I'm not You're not. We're not gonna catch you there. Going to a haunted house. No. Do courageous things, Kim. No, not that way. Not that way. Want me to open up some other business? Absolutely. But I will not go to the haunted house. I might take my son this year because he's. He's 13. He just turned 13, and I just. He thinks he's cool, and I want to show him that you're not. Yeah. So as we kind of wrap things up a little bit, one takeaway, if for the women out there listening that want to start a business, whether it's getting into real estate, buying a building, or being a part of that. What would you tell them? Everybody was born with a gift and gifts and talents, and we need what you have to give. So put it out there. That's great. That's amazing. I like that. That's awesome. Wow. I love it. Kesi, thank you so much for being here. Thank you. Appreciate your time. I love, I love to know you. Hercules. Hercules. That's awesome. Well, just couple upcoming things. You guys catch us at our Wired monthly coffee meetups. Those are usually on the first Fridays or the monthly happy hours and they usually feature a recent Wired development or a member. Those are I believe right now those are the third Wednesday of the month. So our next one is a good one. I'm looking forward to it. You can always check out the website wiredkc.net or our social media for details. Kesi, you were nominated by the wonderful Susan Scott. So if anybody knows a member or woman that's attached to Wired that should be featured on our podcast, let us know. Or if you have interest yourself, just let us know. We'd love to have people. So thank you. Thanks for being here. Appreciate it. Thanks for listening to the Wired Stories of Impactful Women podcast. We hope you left today with something useful, something you can act on, share or carry forward. Subscribe to the show so you don't miss out on what's next. If this conversation matters to you, chances are it will matter to someone else. And be sure to check out our upcoming Wired events. And if you have a member who you think should be featured on the podcast, or if you have interest yourself, reach out, we'd love to have you as a guest. We'll catch you soon right here on Wired.