It's Later Than You Think: Start Living Now

What would happen if you stopped working for someone else's dream and started building your own? That's exactly what Tiffany Freeman did when she pivoted from hospitality to property management and began creating her own real estate investment portfolio.

Tiffany's story resonates with anyone who's ever felt the painful tug between career ambition and family obligations. As a single mother working night shifts in hotels, she made the difficult decision to switch industries when her daughter's poignant comment – "I'm at my aunt's so much, it's like I live there" – made her realize something had to change. Now, as a regional manager overseeing 11 neighborhoods at Redwood Living, she's created a life that allows her to succeed professionally while being present for what matters most.

The most compelling aspect of Tiffany's leadership approach is how she transforms her own regrets into empathy for her team. Having missed countless volleyball games and special moments during her daughter's childhood, she now fiercely advocates for the working parents she manages: "Go to the damn game. This job will be here tomorrow." Her authentic leadership style includes conducting "listening tours" before implementing changes and refusing to sell properties she wouldn't personally live in – principles that have earned her respect throughout her career.

Beyond her corporate role, Tiffany and her husband have established ST Mulligan LLC, purchasing short-term and long-term rental properties as they build their own investment portfolio. Her journey embodies her powerful advice: "It's later than you think, but never too late to get started." Whether you're contemplating a career change, struggling with work-life balance, or wondering if you should finally pursue that side hustle, Tiffany's story proves that with intentional decisions and authentic leadership, you can create success on your own terms. Start living now – the possibilities are endless.

Transcript

Speaker 1 0:16

Welcome to the SheSweet Society, a community where women from all backgrounds come together to share their stories, support one another and reveal the unfiltered reality of our lives. I'm your host and empowerment Sherpa Dahlia, and this podcast exists to give voice and space to women whose experiences might otherwise go unheard. Today I'm joined by Tiffany Freeman, a regional manager at Redwood Living, who oversees 11 neighborhoods and has built her own real estate investment portfolio alongside her husband. Tiffany's story is one of intentional career pivots, authentic leadership and the courage to prioritize what truly matters. What makes Tiffany's journey so compelling is her honesty about the choices she's made to balance ambition with family life, from her early days in hospitality to her transition into property management, specifically to work day shifts and be present for her daughter.

Speaker 1 1:07

Tiffany embodies the kind of purposeful direction making many of us struggle with Her approach to leadership. Conducting listening tours before making changes, showing empathy for single mothers on her team and refusing to sell properties she wouldn't live in herself reveals someone who understands that authentic leadership comes from genuine care for people, not just results. Whether you're navigating career transitions, trying to balance professional success with personal priorities, or learning to lead with empathy while achieving results, tiffany's insights offer practical wisdom grounded in real experiences. Okay, so with you it's a little bit different, because I know you.

Speaker 2 1:50

But I don't really know.

Speaker 1 1:52

Are you still doing regional at Redwood? What are you up to nowadays?

Speaker 2 1:59

But yeah, so currently I am still with Redwood Living and, as a regional manager, I'm currently overseeing 11 neighborhoods, four of which are in Leesup, and so it is a very busy time.

Speaker 2 2:18

But I feel like I'm a little bit of a glutton for punishment.

Speaker 2 2:21

It's just the you know it's, it's, you know, it's something that gets in you and you just keep going with it. And what I've found and I think it's not just Redwood or anywhere else like if you are proven and good at something, you are rewarded with more, oh, yeah, more you know what I mean, right, and so, and that's OK, I mean I think that I have a pretty good relationship with my boss, where, if I really were to the point where I'm like I don't think I can handle this, that you know what I mean, it wouldn't, you know, be a black mark against me or anything like that. So you know. So you know be a black mark against me or anything like that. So you know. So, yeah, so doing that a lot of staff changes and organizational changes and things happening within Redwood. So, but I'm focusing on really that pocket of operations and trying to manage both the stabilized neighborhoods that are doing really well and then putting out fires at lease-ups. You know what I mean, which you're very, very good at.

Speaker 1 3:34

I feel like you've done that for so long and it's so stressful.

Speaker 2 3:38

It can be. Yes, it definitely can be, but I think that the way that Redwood operates their lease-ups is a while it's still stressful. It's a little bit different than the high-rise in the downtown that we've seen. So Redwood, just to be familiar, is built to rent single-story. All of them are two-bed, two-bath, with two car garages and you know you have your own single entrance. So it's not like you have to fight for or schedule a parking spot in order to like move everything in within an hour and a half. People can really take their time, so elevators that may or may not work or may have you stuck in them for hours, you know what I mean, we definitely lived through that.

Building a Real Estate Investment Portfolio

Speaker 2 4:26

So it is stress, but it's a different type of stress. It's a more manageable stress situation and I'm still enjoying it. So you know, we're just, we're just going to move with it. So, on top of that, my husband and I have recently been investing in rental properties, One of which is a short-term rental that we're running as an Airbnb during the busy season and we are renting it on like Furnace Finder for traveling nurses, really during the off season, to, you know, offset not having Airbnb guests during that time frame. And then we have another long-term rental property as well. That's amazing.

Speaker 2 5:19

Yeah, we just finished our first lease with our tenant and we were hoping he'd stay for like five years, but he's outgrown the spaces, so we just are in the turn process, and so I think I just turned into like I'm doing this for other people, I'm really good at this and why not me? Why not do it for myself? And it's a slow build. And it's a slow build. Right, it's a slow build. There is no immediate return, but I know, like, how the market is in Columbus and you know what is $200,000 today. Very well, in 10 to 15 years could be three to $500,000, you know, just because Columbus is not going to stop growing anytime soon. It's a market I'm really familiar with and you know. So we we've been dipping our toes in that and hopefully our hope is, and we've just been going real slow because we still obviously have to work full-time jobs. So it's just in increments, but the hope is to, on our next venture, purchase a duplex and then kind of just go from there. But yeah, we're just jumping in Awesome.

Speaker 1 6:36

You're so right. You've been doing it for so long. You know what you're doing. You know exactly how to do this. I mean seriously. There's so many people that learn from you all the time. I know I did when I first started Well.

Speaker 2 6:49

it's reciprocated. I've definitely learned a lot from you. You know you're brilliant.

Leadership Through Listening

Speaker 1 6:53

So a fun story, just real quick for the listeners, is that I'll never forget when I first started and I'm kind of bullheaded and I'm a windstorm of a person if you've ever met me and you had to have, you had to take me out to lunch and have a difficult conversation with me to be like, slow your roll. Slow your roll, son, and I'm like why Everybody needs to speed up.

Speaker 2 7:20

Yeah, everybody needs to speed up, and you know, and I think that people will get there Right. But to your point, you know you do have a very strong presence, you know you like things a certain way and it's go, go, go. But I think that you know it's important sometimes to, while you're getting your footing and getting to know people, doing just that right, like when I start any job, especially when I'm people leading, I do now what's called a listening tour. So my first few months I'm not really changing anything, I'm not implementing anything. I'm taking a lot of notes, right, but I'm taking my time. I'm going out to eat with people, I'm spending time on site with them, I'm getting to know them, you know better, building trust, building that relationship.

Speaker 2 8:11

And then I dropped the hammer. You know what I mean. I like your strategy, yeah, I mean, but it does and it's important, especially so when I was hired in at Redwood. I was hired in as a regional manager, so there were obviously managers on my team who had applied for the position. So I knew that going into it, and they're already like who is this? You know so, and not only that I, although I've been doing it for so many years. I don't know their systems, I don't know their policies. You know like the back of my hand I don't. You know what I mean. So I really had to build that relationship and build that trust and get them to teach me the job while I'm leading them in the job, if that makes sense.

Speaker 1 8:58

It does, it does, and I know that we've talked about this, but I don't know. I don't remember how did you get started, like, how did you get into this industry?

From Hotels to Property Management

Speaker 2 9:11

Yeah, so I don't think anybody grows up and says, hey, I want to be a property manager when I get older. You know, I think, as you know, it's one of these things that kind of bites you and you stay in it forever in one way shape or form. But no, so I actually have my degree in hospitality and I started out in hotels, which I love and I really did. It was like I had that moment where it's so funny I'm from Fremont, ohio small town, and an adjacent small town had a red roof in, and I was just kind of, you know, my early 20s, I had a young daughter, I didn't know what I was doing. You know, I was just looking for any work. I just didn't want to work in a nursing home and I didn't want to work in a factory and I didn't want to serve tables. You know what I mean. So, but there weren't that many offerings in my immediate area and so there was a opening for Red Roof Inn and I was like making $7 an hour. But I just remember being behind that desk and like I just kind of like lit up. You know, I don't. It's just the weirdest thing. It's just like this is what I'm supposed to be doing. Like you know, it was the hospitality. Creating experiences like seeing people at the end of their day, like traveling and being able to put a smile on their face and provide them a good experience, a clean room, a wow gift you know what I mean those kind of things just like had me nerding out. So you know, it was just like a kind of an epiphany that I had at that point in time. It's like I really want to do this.

Speaker 2 10:42

And so I moved to Columbus with not a plan. But I remember running into a regular at Red Roof that used to stay there. His name was Robert and I told him I was moving to Columbus. He was like well, what are you going to do down there? I really didn't have a plan, I just knew I was going to get down there. I had family, I him I was moving to Columbus. He was like well, what are you going to do down there? I really didn't have a plan, I just knew I was going to get down there. I had family, I knew I was just going to get down there.

Speaker 2 11:09

But I had always drove by to get to my aunt's house Marriott Columbus Northwest and I just always thought it was a beautiful building and so I literally had no plans and I was like, oh, I'm going to be working at the Marriott, you know, in Dublin off of 270. I'm going to be working there and I'll be damned, that's exactly where you know. And I walked in those doors, you know, after I get there and settled and it was again like this is where I'm supposed to be. I worked there for six years and went to school and I really loved it. I loved operations, I loved the fast pace of it, meeting new people and, like I said, creating those experiences for people. But I had to go to night shift because they needed strong presence on night shift and, like I mentioned, I'm a single mom. I have a young daughter and it got to the point where everybody was raising my daughter except for me and and she would say you know what I mean and you know I mean I it's just like heartbreaking because she had said something.

Speaker 2 12:09

Like you know, I met my Aunt Tanya so much like it's like I lived there, but none of my stuff is there and I'm like yeah, very much so, and so I just thought long and hard, like what can I do that is similar to what I'm doing right now, that would allow me the hours that I could work a day shift and be home with my daughter, enter in property management. And so I, you know, I started at Associated Estates, which has dissolved it's no longer a company, but, yeah, I got in as a leasing professional, and then the rest is history, so it's just something that I really really fell in love with. Fun fact though, I actually was not a very good leasing agent. What I can't believe that, yeah.

Speaker 1 12:58

I actually can't believe that. I know.

Being Honest About What You Sell

Speaker 2 13:03

Well, I wasn't excellent at it because I didn't. I have to really believe in a product in order to sell it right, and I would have to be able to picture myself living somewhere in order to sell it, okay. And so, like the one bedroom floor plan that we had at our location, like my closing ratio was like through the roof for that floor plan, but, like at our sister site, which we co-managed, it was these raggedy townhomes I won't name the place, but it was just terrible. And also, too, it was on a busy street and we had to drive over to take them there, and so when we got off, it's on hard road. So you know how that is trying to make a left turn on hard road in the middle of the afternoon. It might be different now I don't know if they.

Speaker 1 13:55

No, it's not. It's still really bad on I don't know what community, but all of hard road is the same.

Speaker 2 14:01

It's terrible. So, yeah, so I would have to make that left turn and somebody's behind me and we're just waiting forever and I'm in my head like there, I've lost them. I've already lost them. You know what I mean? Like nobody wants to wait to make this turn and da, da, da, da da.

Speaker 2 14:18

So I just feel like what was the problem for me was I really have a hard time selling something that I don't believe in, and if I wouldn't live there, or if I wouldn't live there, or if I wouldn't move my family member there, then I'm probably not going to recommend it to you or push the sale as hard.

Speaker 2 14:39

Right, because I know that you're going to come into this office with complaints, you're going to accuse me of whatever you know, and so I just kept it real with everybody.

Speaker 2 14:48

And sometimes, while most people do appreciate that honesty and will rent anyway, you know, a lot of people are like whoa, thank you for telling me you know that kind of thing. So. But I think that how I did succeed and was able to move up is you know, folks that were in charge at the time were able to see and observe, like just how I was, as a leasing professional, able to look at everything from like a bird's eye view and, you know, help coordinate well. Maintenance should really be doing this, you know, and that I was able to see how the operation worked and even though I'm a great manager, I'm not an awesome leasing professional. I sat in the seat. I know what it feels like, and I also know what it feels like to not be a top performer in that seat. So I think that ultimately, that did help me to empathize when I have folks that are struggling. You know what I mean.

Missing Moments and Work-Life Balance

Speaker 1 15:51

You are the type of person that just I feel like naturally comes with empathy. Yes, sure, maybe sitting in that seat helped you see it better, but I feel like you would have seen it anyway, which is not a trait I think a lot of people have. But you do and I think that's pretty how self-aware of you to know that about yourself understand how difficult the job can be but then still be able to manage people, for that, think anything in growing up is what helped you be more of a strategist, or do you think that's a personality?

Speaker 2 16:22

trait. I've always kind of liked to be bossing people around. I mean I like you know student council president, you know what I mean. That kind of stuff, you know I yeah.

Speaker 1 16:40

What were you like in school? Student council president.

Speaker 2 16:45

I was kind of a nerd, I mean, if I can say that I, you know I was. I was well-liked, I feel like, by everybody, but I wasn't considered popular or anything like that. And I I was a teacher's pet. I really was so like, for example, I'm in like eighth grade and the viewers aren't going to be able to see this, but the when you put the L on your forehead, you know that was like a new thing at that point in time. And we're in the cafeteria in line and people were doing it to my teacher and he came to me and was like what does this mean? And I was like loser, they're calling you a loser you know what I mean like so, but I still remained likable with everybody else.

Speaker 2 17:28

but that just kind of was you know how I operated during you know school and yeah just tried to.

Speaker 1 17:37

You have sisters? I do. I have two sisters, and where do you fall on them again?

Speaker 2 17:42

You're not the oldest, I am the oldest, you are the oldest, I am the oldest, yeah.

Speaker 1 17:48

That explains the bossiness.

Speaker 2 17:49

Yeah, a little bit, even though my middle sister really was very, very much in charge most of the time at home, like she was stronger, more athletic, so she won a lot more of the fights. But you know, as far as you know, giving direction and things of that nature, it just it really did kind of come natural to me and things of that nature it just it really did kind of come natural to me. You know, with my sisters, cousins I'm the second of six and I would say my cousins really are like siblings to me, the six of us are. And so, yeah, I've just, like I said, been bossing people around for a really long time.

Speaker 1 18:31

How do you balance that? Or I hate the word balance, because but how do you balance having the time to still dedicate to your family and your friends, as well as work? Because, we know this, this job is extremely demanding.

Speaker 2 18:46

Yeah, it is. It is really demanding, but I think that I found the company I'm with now is very big on work-life balance, and so my so when I came in for my initial interview, they said something that just like blew my top off and it was like we don't deny PTO here. If we have to close an office, we will close an office and I'm like what? But you know, but I think that that is very much appreciated by everybody and like into this day, listen, if our exposure is really really crazy, you know I would still allow the PTO, but let's find some coverage. You know what I mean, like that kind of a balance. But yeah, I think it's family is so important your friends, your loved ones. Like work is. It takes up a lot of the week. I mean, we're with the people that we work with more than we are with the people that were at home, and so you have to have the ability to sometimes just like shut it off or say you know, no, I'm not doing this.

Speaker 2 19:53

And I wish that I had this type of I guess confidence or I don't know if that's the right word, but I, for example, when Madison was really young, my daughter, she was playing volleyball and things like that, and you know how hard it was to get out of that leasing office. But you know what I mean was to get out of that leasing office. But you know what I mean. If you're not out of there between like three and four, that four to six hour, you're slammed, especially in the offices that we were at in the downtown market. But I remember like getting off of work a little bit late, trying to make it to her game, getting stuck in traffic and then finally getting there to already have missed her game or her set. And I walk in the door, sweat rolling down my back like stressed from, you know, blood pressure through the roof, trying to like get there and to be greeted with her rolling her eyes at me because she's disappointed that I missed her set and there was nobody there to cheer her on. And I wish that I could say that was an isolated situation. But there's just so many things that I missed out on when she was young because I was at work and I felt like I didn't have a choice.

Speaker 2 21:03

You know I didn't want to keep asking to leave early. I mean, these are the jobs, this is the parameter, but I think that, going back to that time frame that Tiffany, I wish I could tell her take the time off, leave. What are they going to do? Are they going to fire you? I don't think so. You know what I mean, and I just think that I was afraid of those things and not really knowing my value and demanding for that extra time.

Speaker 2 21:28

And so it is empowering I'm almost Terry I'm talking about this, but it's empowering to me to be able to encourage that for the young mothers on my team you know, that have kids and that are single moms and don't want to miss those games, like I don't want to miss those games either. So go, you know this, this will be here tomorrow. I promise you this word, this job, this resident, this issue it will all be available tomorrow. Go to the damn game, go spend time with your kids, go spend time with your family. So I just love. I do love.

Speaker 2 22:07

That really kept me successful is no matter how long I've been like quote, unquote, off site, I will never forget what it feels like to be on site and to have that grueling. I think sometimes when you get into the corporate level and you're spending time at the corporate office, you can really lose that touch, you know, and you can really forget what that's like and I just never want to forget. I never want to forget. I think that once you do like your management people leading skills, they really tank, whether you're aware of it or not.

Speaker 1 22:45

I couldn't agree more and I think it's what makes a really big difference within the people you work with at corporate. You can tell when you're having the people you work with at corporate. You can tell, when you're having decisions and you're talking at those tables, who remembers and who doesn't and who's never been on site.

Speaker 2 22:59

I was just going to say that. Who's never been on site, that's a big problem at corporate office.

Speaker 1 23:04

yes, it is a big problem and what I've noticed recently just from all PropTech being a big thing now, I noticed that the prop tech companies that get it are usually the ones that go and find people that have worked on site before and employ them so that they can build a product that actually works for us. I love that message and you know, I very much agree with that. You can't get time back. In fact, that's the only thing you can't ever go back and get. So whatever you need to do to spend time with the people that you care about most is the most important thing. So I'm glad that you brought that up. How does Madison talk about it today? You guys are very close. You guys have always been very close and she is just an amazing human. You've raised an amazing human. You know that. How, um, how is she today? Does she, does she bring it up and like shove it in your face every now and then like remember that time you missed that one game or what?

Speaker 2 24:04

luckily for me, she has a horrible memory. No, she doesn't. I mean she has fond memories of you know what I mean growing up and things like that she doesn't have. She never brings anything up, she's not resentful and I think that, you know, getting into this industry really did help a lot, even though I did miss a lot of games being in this industry, I was at least at home at night, we could have dinner together you know what I'm saying Like she wasn't spending the night places or somewhere until 11 PM until I could pick her up.

Speaker 2 24:39

But yeah, I think that she she gets it. She understands now a lot more, you know, as, as she's an adult and she doesn't have any children yet, which you know, she's knocking on the door of 28, which is insane. To have a 28-year-old daughter when I'm only 35, that's nuts, that is insane, it's insane. But you know she doesn't have any children of her own. But I think she really does appreciate and she understands. Like you know, I had to work and I had to provide and I think that you know I wasn't so spread thin that I wasn't present for her. I just wasn't able always to be physically there, and she gets that.

Speaker 1 25:28

I get that. I'm glad that you brought that up, because there's a lot of people that feel the same way, that will listen to this and feel relieved that we're not alone, and I still feel that same guilt today.

Start Living Now: Final Advice

Speaker 2 25:38

You know what I mean. You just don't get away from that. But the truth of the matter is she's an adult, she gets it now. I'm forgiven, and I should just forgive myself and not replay that memory. You know what I mean?

Speaker 1 26:04

It's on you now.

Speaker 2 26:05

Yeah, exactly, and so I'm just waiting for the day that I have, you know, grandchildren.

Speaker 1 26:20

And then I can retire and just be with them all the time. Go to everything that they have. Keep doing the short-term rentals and the Airbnbs, and you'll get there, so buy your duplex you'll get there quicker than you can imagine.

Speaker 1 26:24

Yeah, okay, in the interest of time, I always end each episode the same, which is to ask you, although it happens every episode, the entire episode is basically advice, but I always like to end with if you could give somebody a piece of advice, whoever's listening to it today, what would that advice be? And it can be personal or professional, or both, or just like words of wisdom you live by.

Speaker 2 26:49

Yeah. So I think that there's a lot of advice that you can give to folks dream, or you're working for somebody else's dream, right? And so if you want to make that difference, you just have to make that decision. You know, and it's like, oh, I feel like, and I feel like, well, feelings are just thoughts put into action, you know. And so if you can change your mindset and you can change your thought pattern, you can change your life. If you can change your mindset and you can change your thought pattern, you can change your life.

Speaker 2 27:33

And it's, you know, it's later than you think, but it's never too late to get started on something, right. And so it's like, oh well, I've, you know, given my life away to this or that. Well, you don't have to keep living in that space, right? So, forgive yourself, do what you have to do and just get started with what you have and where you're at. And you just don't. The possibilities are really really endless and I'm really excited, even like, for myself and my journey. I mean, I'm in my late 40s now just starting to really realize a lot of these principles and learning about the compounded interest over time.

Speaker 2 28:11

And, like you said, I mean like if we continue to build a portfolio. I mean, it's just like one day I'm going to look in my bank account and be like whoa. You know what I mean. And so just manifesting that and putting that you know. But yeah, that would be my advice. It's later than you think. Start living right now. There is no reason to live in. You know, things are hard right and we go through things. Life is not going to just be, you know, simple, but you just can't stay there. You know, feel what you feel, but keep it moving. You know what I mean Because, like you truly are in control. There's a lot of outside factors but you control you. You can't control what happens, but you can control how you react to it.

Speaker 1 28:54

I've never heard it put like that, you know, and I love that you put it that way, because everybody thinks, oh, I'll get to it tomorrow, oh, I'll get to it next year, or when I turn a certain age, or when I've reached the third milestone, then I'll do it. Why Do it now? Do it now Just start right now? Why do it now just start right now? Yeah, I find a lot of people, if it's not due to that, it's due to well, it's not perfect yet, so I can't start, and that's just a load of bs absolutely.

Speaker 2 29:22

It's never going to be perfect. You can always work toward perfection, but it's never going to be perfect. I mean, I still don't even know what the hell we're doing right, but you know, it's happening like it's we're, but you know it's happening. Like it's, we're moving along. We, you know, we've been you know, I would say you know very successful so far in those ventures. So very busy. I'm so excited for you.

Speaker 1 29:45

Yeah, it's busy. It's going to be busy for a little while. Oh yeah, it'll become yours. Yes, have you thought of a company name?

Speaker 2 29:55

So we are under ST Mulligan or St Mulligan LLC. I like that. I like that. That's really cute and then also because it's Sean and Tiffany big S little T, so St Mulligan yeah.

Episode Closing Reflections

Speaker 1 30:18

That's so awesome. What strikes me most about tiffany's story is her commitment to authenticity in both leadership and life. Her realization that she couldn't effectively sell property she didn't believe in speaks to something many of us face the tension between professional expectations and personal integrity. I'm particularly moved by how she's channeled her regrets about missing moments with her daughter into empathy for her team members. Her encouragement to single mothers to prioritize family time shows what leadership looks like when it's rooted in genuine understanding rather than just business objectives.

Speaker 1 30:49

To Tiffany's advice for life it's later than you think, so start living resonates because it comes from someone who's made hard choices to align her career with her values. Her reminder that we control our reactions to external factors, even when we can't control the factors themselves offers hope for anyone feeling stuck in their current circumstances. For those of you making decisions about work-life balance, considering career pivots or trying to lead with both effectiveness and empathy, tiffany's journey reminds us that it's possible to be successful without sacrificing what matters most. If today's conversation inspired you to stop making excuses and start pursuing what you really want, share it with someone who needs to hear it. Remember SheSweet Society exists to amplify women's voices from all walks of life, proving that success can be defined on your own terms. Until next time, this is your host, dahlia, reminding you that your life is your message to the world. Why not make it extraordinary? Thank you.