Skip to main content

Antonio Womack on Underwriting, Uncertainty, and Safer Plays

By October 6, 2025Real Estate Pros Show

Subscribe via:

Show Summary

Antonio Womack, a Baltimore-based investor and developer, joined the Investor Fuel Podcast to share his entrepreneurial journey and vision for legacy building. He began his career running a successful restaurant before transitioning into real estate in 2001, where he built large-scale development projects. After weathering the 2008 downturn, Antonio took a detour working in education and publishing before re-entering real estate in 2017. Today, Antonio is focused on a mix of development, flipping single-family homes, and building a portfolio of multifamily properties, including boutique student housing projects to meet high demand near universities like Morgan State. His mission centers on community impact and creating a legacy for his two sons through long-term property ownership and development.

Resources and Links from this show:

  • Listen to the Audio Version of this Episode

    Investor Fuel Show Transcript:

    Antonio Womack (00:00)
    that regardless of what you think you want to or should be doing ⁓ in a certain situation with a certain deal, a certain property, a certain opportunity, ultimately the market ⁓ dictates a lot of what the outcome will be in a particular deal. It really does. The market has a lot to do.

    And that’s why it’s so critical even today and what’s going on with the economy. you know, we got tariffs, we got downward pressure, we got upward pressure from different directions in our economy. creates a lot of uncertainty in the market and makes it very difficult for ⁓ investors and developers to decide a path.

    Michelle Kesil (02:21)
    I’m your host, Michelle Kesil. And today I’m joined by someone that I’m looking forward to chatting with, Antonio Womack, who has been making serious moves as an investor and developer in the Baltimore area. So excited to have you here today, Antonio.

    Antonio Womack (02:40)
    Thank you so much, Michelle. I’m excited to be here. Looking forward to it.

    Michelle Kesil (02:44)
    Yeah, of course. I think our listeners are really going to take something away from how you’re approaching your markets, closing the deals, investing the access to capital and all the new projects that guys are working towards.

    Antonio Womack (03:01)
    Absolutely. Yeah. Yeah. And if you don’t mind, when we start, I’m going to go back a little bit and talk about a little tiny bit of my past because I think it’s important to where I am now.

    Michelle Kesil (03:13)
    Absolutely, let’s start with that. How did you get to where you are now? How did you get started in this?

    Antonio Womack (03:19)
    Yeah, so well, way back when I purchased a restaurant with some friends, we owned that restaurant for a number of years. It actually did pretty well. It was a very successful restaurant in Baltimore. We ended up selling it about four or five years later when we just got tired of working 16 hour days and we sold it for profit. And I bankrolled my part of that into real estate investment and real estate development and started my first company back in

    2001, it’s called CIMG and I really didn’t know much about this business. I didn’t, I was kind of learning as I went. It was really a pull yourself up by your own bootstraps kind of situation. I did have a few people around me that were mentoring a bit, but honestly I was learning as I went. So that company, CIMG from 2001 to 2006 was growing. We had about

    100 by 2006, $160 million worth of projects under development. They were arranged between 120 units and 160 units. What happened? What happened was 2008, 2009. And if you were around and in this business, you witnessed it. And it was the first time I’d ever really witnessed a downfall of an economy. So I felt it full brunt.

    We were in the middle of construction on 30, $40 million projects at a time, multiple projects, and the economy crashed. Banks started calling notes, and I thought it was end of the world, period. That’s just what it was, right? ⁓ And

    that’s an important part of who I am and where I am, right? ⁓ Because ⁓ it took some time to kind of get back up.

    up and start to figure out what direction I wanted to head back in and rebuild. Part of that process was going back to work. I went back to work and was a business liaison and then a managing director of food nutrition for Baltimore City Schools. So I took a big detour, totally different direction, right? Didn’t want to see a piece of estate except the one I lived in, right? And thought I would never get back in the business. But I ended up writing a book.

    got published in 2014 by Waldorf, went on a book tour, and then ⁓ an opportunity came around 2017 for me to get back into real estate game. And it was a development opportunity. I looked at it. ⁓ I jumped in with some other partners. And that was my first re-entry back into development. And my second was a project that we discussed a little bit earlier, and that’s a

    99 unit project that I’m a partner in on Park Avenue in Baltimore. It was a RFP that we won. We bid, we won, and it’s been a long haul. We’ve been working on that one for five, six years, but it’s finally coming to completion. We’re getting ready to deliver it within the next week or so. We’ll be delivering the product, and so I’m happy about that. So that’s kind of a little bit about who I am, where I come from, and how I got here.

    Michelle Kesil (07:28)
    Amazing. I love your story. So cool to see how you started from one point and got to where you are now. So yeah, for those that are just getting familiar with you, what is like your main focus now? What are you up to these days?

    Antonio Womack (07:47)
    Well, so the good thing about Baltimore and the market that I’m in right now is that the market here has been pretty steady in terms of it being a seller’s market. So the component of real estate we do is this, we have got some development projects, but I also have some investment projects. So, and I also do flips. I’m in every part of that market. So right now we’re engaged in four flips.

    ⁓ in this market. The market here is pretty strong. ⁓ are still buying. It’s pretty stable. So that’s a really good thing. ⁓ I also invest. So ⁓ we purchase, when I say we, I really mean I, because it’s, mean, I’m pretty much the sole owner of the company, but I purchase multifamily properties that I hold. So I flip single families, I hold multifamily. And part of that multifamily,

    is our new student housing portfolio. It’s boutique housing. So we’re not going after like the two, three, 400 bed developments at this point. Right now, I’m focusing on anything from 10 to 80 beds. That’s boutique student housing. In areas that are critical, schools that need the housing, one of them here is Morgan State University, the illustrious Morgan State University. ⁓ They have hundreds of kids still on the waiting list after school has even started.

    And so, and they’re just one, there’s lots of schools that need student housing. My youngest son is at Syracuse University. They need extra student housing. So it’s across the board, it’s a huge need. So we’re gonna fill that need, we’re gonna help fill that gap. ⁓ And so we just finished our first one, it leased up in three weeks. We have another one that we have site control of that’ll close next week. And we plan on having that leased up by next semester. So it’s just ⁓ part of an ongoing portfolio.

    Michelle Kesil (09:45)
    Amazing. Sounds like you’re doing some really powerful service helping those that need it in your community.

    Antonio Womack (09:56)
    Definitely, absolutely, yeah. It’s all about community for sure.

    Michelle Kesil (10:36)
    Awesome. So what are some of your goals? Where do you see your business heading? What are some of your dreams and where would you like to go?

    Antonio Womack (10:51)
    Well, know, ⁓ part of this mission that I’m on now, in this phase of my life and my career, is about ⁓ legacy building. You know, I two sons and ⁓ I’d like to create a ⁓ body of ⁓ properties, of wealth and legacy that I can pass on to them and that they can continue to build and develop.

    and make the impactful kind of changes that we make in communities all across Baltimore. That’s one of the beautiful things about what we do. I love going into a building that’s vacant, dilapidated, and seeing it six months later, three months later, five months later, and seeing something that people want to claim is home. That’s a beautiful thing. It’s a beautiful part of the journey. And so for me, ⁓ that’s part of what I want to continue. Like, I don’t really see myself

    retiring per se because I really love what I do. I love this work. And so I don’t really see myself retiring from it. I want to keep doing it until my bones and my hands and my brain won’t allow me to do it anymore. That’s when I’ll stop. But yeah, so that’s kind of what ⁓ my goal, my end goal is. And I guess if there was a dream attached to it, my dream would be to take this beyond just our market and maybe into a market that’s more regional.

    and national maybe.

    Michelle Kesil (12:23)
    Absolutely, I love that. It’s definitely possible for you. Amazing. So, let me ask you this, of course. Every business owner has those moments where things get real. Maybe you have a deal that goes sideways or you need to make a fast pivot. Would you mind sharing one of those moments for you?

    Antonio Womack (12:50)
    Wow, wow, God, there’s been so many times, so many times on so many deals where, you know, you have to make a pivot ⁓ in terms of any particular deal. I remember there was one ⁓ deal that we were working on that was a development opportunity that ⁓ it was another RFP that we had won.

    This is back in my former company, not this current company. And ⁓ what happened was, you know, the market, when we won the RFP, ⁓ we were going to build 160 apartments. And it was over top of a garage near a very popular market in Baltimore. And the problem was when the partners that I bought in were a national development company, I was a small company.

    They were a national development company who were going to come in, basically bankroll the project, and we were partnering to make that happen. Right? I was the local boots on the ground. And ⁓ when you win an RFP, it’s a big deal. You know, you’re getting this property, the city has accepted your offer. You know, they’re giving you the keys to be able to move forward on it. ⁓ But when the partners came into town and we walked the property, they saw some things. ⁓

    here that they weren’t comfortable with near the property, around the property. And then the rents that we needed to achieve at the time ⁓ when they did the market study, it demonstrated that that property, if built at that time, would not achieve the rents that it needed to achieve to be able to pull the deal off. Now, quite frankly, I’m going be honest with you. I would have probably, you know, I would have made very good money, seven figures in that deal.

    I wanted that deal to happen very much, but I couldn’t change the circumstance. couldn’t change the market and where it was at that point. And so the pivot was we literally had to go back to the city

    after we got that market study and say, we can’t do this deal now. We’re not going to be able to move forward with this RFP that we would just want beat out other people for it because the market

    is simply not going to support the rents that we have to charge to make the deal work. That was difficult and we had to pivot away from it and actually move to look at other deals, which we eventually found something else. But that was a tough situation and you’ve got to be ready to make the big boy decisions ⁓ when the time comes. That was just one of those times. I did not want to walk away from that deal, but

    We had no choice.

    Michelle Kesil (16:29)
    Yeah. Yeah. Yeah. Absolutely. What did you learn from that experience?

    Antonio Womack (16:36)
    Well, ⁓

    that regardless of what you think you want to or should be doing ⁓ in a certain situation with a certain deal, a certain property, a certain opportunity, ultimately the market ⁓ dictates a lot of what the outcome will be in a particular deal. It really does. The market has a lot to do.

    And that’s why it’s so critical even today and what’s going on with the economy. you know, we got tariffs, we got downward pressure, we got upward pressure from different directions in our economy. creates a lot of uncertainty in the market and makes it very difficult for ⁓ investors and developers to decide a

    See, every time you move forward on a development deal, quite different than an investment deal. I’ve done both. Development deals take

    Years to matriculate. It’s not something you wake up decide you’re do and then tomorrow you get to build it No, you’ve got to go through entitlements. You have to go through all the legal, you know Work, you’ve got lots of work to do to get a property ready That’s a development property that you’re building from ground up to to get it ready for market that could take two to four years easily Well, if you’re in uncertain economic times or the political times

    and you’re not sure which direction things are going to go, it’s difficult to plan through that. But if you have a project that is only a three month flip, well, I’ll take that chance because in three months, you know, I can see three months ahead and predict better on what outcomes look like in that situation. And so ⁓ it’s a bit safer, to be honest with you, to invest in short term in uncertain markets than it is to develop in long term uncertain.

    That’s an incredible lesson for anyone who’s going to watch this.

    Michelle Kesil (18:39)
    Absolutely, that’s so important and so wise. Thank you for sharing that, definitely.

    Antonio Womack (18:45)
    Yeah, definitely.

    Michelle Kesil (18:48)
    Awesome. So what are some of the things that you’re focused on solving right now? I know you mentioned the student housing, but are there other areas or developments or investments that you’re focusing on? ⁓

    Antonio Womack (19:07)
    I mean, multifamily, know, student housing is one facet ⁓ of multifamily as far as, you know, we look at it. We consider student housing multifamily, but we have another whole section. I’m settling on a smaller multifamily. It’s only 12 units, but it’s, it’s, getting it for a great price. Matter of fact, at one point it was literally a value to 2.1 million when it was operating and we’re picking it up for a million.

    you know, ⁓ because it went into foreclosure. It needs some work, it needs some love, and we’re gonna put that love in it, and we’re gonna get it back in the market and back on the tax roll for the city. So, ⁓ you know, that’s gonna be another big part of ⁓ what we intend to do and what our focus is moving forward. We’ll be ⁓ continuing to move forward on.

    multifamily projects and again some of them are smaller and then we’ll with this particular model I mean we’ll go up to maybe 30 40 50 units now there’s a whole nother segment past that when I start looking at size and developments past that it gets more to development than it is just investment for us I mean we could certainly you could go in and purchase a turnkey 300 unit development if that’s what you want that’s not what we do

    I don’t buy at the top of the market. I buy at value properties because we have construction experience. So I buy properties that are at value that we can go in at value to and turn them around.

    Michelle Kesil (20:47)
    Yeah.

    Antonio Womack (20:48)
    So for us, anything over 50 units is most likely going to be a development. That’s the point. It’s not going to be just an investment.

    Michelle Kesil (20:55)
    Yeah, that makes a lot of sense with where your business is. Yeah, how it’s structured.

    Antonio Womack (21:01)
    Yeah, definitely.

    Michelle Kesil (21:04)
    So when it comes to growing your network, building relationships, expanding your business in that sense, what are some things that have made the biggest difference for you?

    Antonio Womack (21:17)
    That’s a very good question. will tell you that networking has always been my strong point. One of the reasons I was able to grow the first business from 2001 when I started to 2007, 6, 7, where we were doing hundreds of millions of dollars worth of deals is a lot of that had to do with networking. The fact that I was out shaking hands at events.

    lots of networking events, lots of political events, you know, ⁓ meeting the right people, rubbing shoulders and making those connections. that’s something that, ⁓ I’ve just, ⁓ always had in my wheelhouse. It’s always been, ⁓ one of my assets and it continues to be, I don’t do that as much as I used to mainly because I don’t really think.

    that I’m not in a position where I need to be out like I was when I first started. You know, you really, when you’re first starting and trying to make your way and make the relation, get the relationships and make the connections, you got to be out there. You got to be networking. You got to be going to events where like-minded people are, where real estate experts are, where bankers are. You got to be out there. ⁓ Now I have a lot of those relationships. And so it’s a matter of just picking up the phone, making the right calls and don’t get me wrong. I still network.

    I still go out occasionally, especially when it’s this right type of events where I know key people that I have to get to are there. So that’s definitely a big, big part of the process and of the journey. I’d advise anybody who’s looking to ⁓ move forward and build a real estate portfolio or real estate career, networking is…

    the most important part of that process.

    Michelle Kesil (23:15)
    Yeah, absolutely. Relationships are everything in this space.

    Antonio Womack (23:21)
    everything. Yeah, definitely. Do you get a chance to network a lot as well?

    Michelle Kesil (23:28)
    ⁓ Well, I’m in bit of a different role, so it’s not exactly the same.

    Antonio Womack (23:34)
    I you. got you. I just love to do it. I don’t know if you’re a gregarious outgoing kind of, you know, hitting the events kind of person, but I’m out, you know, I still go out and still try to get some networking done.

    Michelle Kesil (23:36)
    Yeah.

    Absolutely, it’s so important to meet people and see how everyone can be of value to one another.

    Antonio Womack (23:58)
    Absolutely.

    Michelle Kesil (24:00)
    So before we wrap up here, if someone wants to reach out, connect, collaborate with you, where can people find you and connect with you?

    Antonio Womack (24:10)
    ⁓ They can reach me at a ⁓ rod at trust properties spelled out trust properties dotnet. ⁓ They can reach me ⁓ at a R WOMACK at live L I V E and is a are W O ⁓ A C K at L I V as in Victor E dot com.

    Both my emails are, I check them every day and I’m very accessible by email. And look, if you’re in Baltimore, if you’re looking to do some business, if you want to know more about real estate in general, feel free to reach out to me.

    Michelle Kesil (25:00)
    Perfect. Well, listen, I appreciate your time, your story, and your perspective. So thank you for being here.

    Antonio Womack (25:07)
    Michelle, thank you so much. appreciate you too. Let’s do it again.

    Michelle Kesil (25:13)
    Yes, of course. And for those tuning into the show, if you got value, make sure that you’ve subscribed. We’ve got more conversations with operators just like Antonio who are building real businesses. And we’ll see you on our next episode.

Tags:

Share via
Facebook
X (Twitter)
LinkedIn
Mix
Pinterest
Tumblr
Skype
Buffer
Pocket
VKontakte
Parler
Xing
Reddit
Line
Flipboard
MySpace
Delicious
Amazon
Digg
Evernote
Blogger
LiveJournal
Baidu
MeWe
NewsVine
Yummly
Yahoo
WhatsApp
Viber
SMS
Telegram
Facebook Messenger
Like
Email
Print
Copy Link
Copy link
CopyCopied