Loading summary
Hillary Cheney
I was diagnosed bipolar in my 20s. I went to law school, failed the bar exam. My husband and I got married, got into a lot of debt, student loans, credit cards, all that. And then he got stage four colon cancer three years ago. And so I'm a widow as well. So building success through trauma and the way I've done it is discipline, commitment and consistency.
Narrator
Hillary Cheney is a resilient visionary and purpose driven real estate investor and and the founder of Lexington family Investments llc. Drawing from her journey of overcoming profound personal loss, she empowers individuals to rebuild their lives and reclaim their strength, creating a lasting legacy of hope, transformation and fearless leadership.
Hillary Cheney
Somebody told me good debt builds wealth. And that's scary to think of, like taking this, you know, $500 and putting into something that will start to earn for you. But that mentality of like spending, spending smart money to build is where I am to financially have the freedom and peace that I have. And having. That's the monster. Not having money is the monster under my bed. So when I tackle that problem getting a credit counselor and getting a financial planner, the monster's gone. And so I can succeed.
Podcast Producer
It spans the globe like a super high is called Internet Elvis Preston. Today Apple is going to reinvent the phone. It's not over until I the living your legacy podcast for those who live to leave a legacy the impossible has. Oh, that is sensational. Jordan, open Chicago with the league. You said Paul is the fastest man on the planet. You can live your dream.
Ray Gutierrez
Welcome back to another episode of the living your legacy podcast for inside success. I am Ray Gutierrez. Joining me today, moments before we film her episode for women in power is. Don't tell me, Hillary Cheney quite the name. And I've got some show notes waiting for this. Hillary Cheney is a federal law clerk, real estate mini mogul and an advocate for finding the gold in others. Is that correct?
Hillary Cheney
Yes, that's right.
Ray Gutierrez
Welcome to the show.
Hillary Cheney
Thank you so much for having me.
Ray Gutierrez
We are moments away from filming your women in power episode, Hill. Can I call you Hill?
Hillary Cheney
Everyone is old volleyball nickname. Come on, Hill, let's go.
Podcast Producer
I love it.
Ray Gutierrez
That's great. What are we going to learn about you and your women in power episode?
Hillary Cheney
Just getting through the mess that everybody gets through. And it's been a lot. You know, I was diagnosed bipolar in my 20s. I went to law school, failed the bar exam. My husband and I got married, got into a lot of debts, student loans, credit cards, all that. And then he got stage four colon cancer three years ago. And so I'm A widow as well. So building success through trauma and the way I've done it is his three words. Nathan, my soulmate's three words were discipline, commitment and consistency. And just find something you can do that you, that you're able to do. Like people would say, oh, go keto or stop drinking or do those things are hard. Find something you can incorporate daily that's good and you can do. And just keep doing it, keep doing it.
Ray Gutierrez
Easy wins. That's no such.
Hillary Cheney
That's quick wins.
Ray Gutierrez
It's not back to quick wins. Let's say quick wins, not easy wins. Because easy. Even the word easy is kind of like, I want hard wins easy. So nice. Hard wins. Low hanging fruit. Quick wins. Thank you again for being on the show. I gotta ask, what is your day to day? Like today I wanna focus on your present day. And let's start from the top before we rewind a little bit. What is your day to day? Like, what are your daily affirmations every morning?
Hillary Cheney
Sure. Well, honestly, my trick, when I figured out two years ago that real estate investing was gonna be my future and went from zero rental properties to five in two years was I said, what do I look at on my ph thing in the morning? Like, what is that? What is my interest right when I wake up right before I even get out of bed? And it was Zillow and interest rates and the markets and Airbnbs and all this stuff about real estate. And I was like, well, I've never done this before, but I must love it. So I still to this day, five houses later and a successful mogul, I guess. Look at that first thing in the morning where interest rates. How does Zillow look? Have there been any price cuts on houses? I'm looking at all that stuff. So I do that when I wake up.
Ray Gutierrez
So when you wake up in the morning, are things that always that organic where it's constantly changing or you're just expecting change? What are you looking for?
Hillary Cheney
Well, I'm used to change with widow and financial ruin and failing the bar exam and all that stuff. I'm ready for being a weeble and popping back up because, you know, I. And honestly, I've been through so much again, everybody's been through so much. But there's something in me that's just this golden like motor, this little motor that was a state volleyball player of the year and some succeeded so well when I was younger that just keeps going. And every day I wake up and the lights are on, my kids are safe, they're you Know my dogs are okay and we're gone, we're moving.
Ray Gutierrez
I gotta ask, cause I feel like this is a great question for you. What do you think came first though? The power or the woman?
Hillary Cheney
Gosh, gotta go with that golden power. Yes, ma'. Am. That's in my heart and that I see in other people. And I think it's love. I mean, I think that what connects us is love. That's the greatest thing thing there is. But I just see other people like you. Your shine, your smile, your energy. I just see that and mirror it.
Ray Gutierrez
Masking,
Hillary Cheney
not me. I try to draw that out and recognize that in other people. And that has allowed me to surround myself with people that in my daily life, my bosses, my accountant, my therapist, all are people that have recognized a goldness in a light, a shine.
Ray Gutierrez
A lot of folks can just kind of, kind of tap out and go, well, the darkness has found me. I guess I'm going to be one with the darkness. You are quite the contrary. You found the light within the darkness. Can you talk about that journey?
Hillary Cheney
Sure. So really the catalyst for all this, I will tell you. When I was about five years old, I told my dad, I said, dad. And I was a normal kid at that point. I said, I feel things too much. When I look at people, I see everything in their heart and soul. I see their pain and their joy and their hurt and everything. I was like, this is abnormal. And it's really hyper empathy. And it turned into a symptom of bipolar when I was diagnosed at 24, which is just feeling too much, right? And so in high school I just turned it off. I was the ice queen. I just, you know, was miss perfection and grades and athletes and all that was very safe in my lane of like, I don't want to feel too much. And then after I graduated college at Washington and Lee and had a great career there playing volleyball, I went to Richmond, Virginia, a lot of stress with my new job and wound up manic. Didn't know psychotic break, not sleeping or eating for six days. Checked into a psychiatric hospital, was diagnosed bipolar. And I can remember being there and I was terrified. And you can die from not sleeping. And so I was in bad shape. Thank goodness for the psychiatric care in Virginia. But I would have this dream and talking about the darkness. I would have this dream there in the hospital that I was in a Star wars war world and I was at the bottom of a ladder and there was all this darkness under me, all of space under me, and I would be like pulling myself Up. And I would pull myself up, rung by rung, and I'd get one rung up, and then I drop down, and my feet would swing in panic, like, above the abyss. Wow. And so I had to learn, relearn, learn for the first time how to continue to put that arm up and you fall down and you put the other arm up, and it was like, bit by bit. And when I was at my worst with depression from bipolar, my mom would be on the phone with me four states away. Like, here's how you brush your teeth, Hillary. Here's what we do. You pick up the toothbrush. Now you pick up the tooth. Like, bit by bit. I have to break everything down into, like, the smallest bite. When I'm doing poorly, when I'm succeeding and excelling, it's like. It's a breeze. It's fun. The flow, the power, woman. They're like, hey, I can do anything. And so. But then you have to be mindful of those dark, scary, terrifying, claustrophobic moments and learn what to do.
Ray Gutierrez
For someone that hasn't been diagnosed and pretty confident I suffer from multiple personality disorder and bipolarness. How does one know? How do you know that something ain't right upstairs?
Hillary Cheney
Yeah. Okay. So I would say the trigger for me and for a lot of bipolars in particular, is sleep and insomnia. And so if you're up, like I went before I was diagnosed, I went to my office in Richmond at 3am and worked on my computer. Not normal.
Ray Gutierrez
No.
Hillary Cheney
You clean all night long. You spend $5,000 in a day. You don't have money. You.
Narrator
You.
Hillary Cheney
You're racing, you're spinning. You're Kanye, you're Brittany, everything, your brain is racing. It's like shuffling like a deck of cards. And so you can't sleep, you're anxious. I talk on my website, Hilary, Beth, honey. About things to do and say if you have a bipolar in your family and certain things are good and certain things are bad, if you're not sleeping and you're bipolar and your family loves you and they want to do the right thing, and they say, just get some rest. Just relax and sleep. And you're like, I physically cannot. That's the worst thing you could say.
Ray Gutierrez
Hey, do you need some help? No, I'm fine.
Hillary Cheney
I'm just over here, like, stimming. And then they say, well, what can you say as a family? And it's hard for family with people with severe mental illness. It's really hard. Thank goodness for a great family I had. But what I Would love them to say to me when I'm spinning is what are the monsters under your bed? What is the fear? Is it you lost your job? Is it you're about to divorce? Is it just normal stress of school or life or whatever? What are the monsters under your bed? And that means somebody's listening and cares and really wants to know.
Ray Gutierrez
Yeah, it's funny you go there. Cause I always ask who's talking right now? Who is the center voice, who's got center stage and who has to take a step aside for that one person to speak their truths or speak whatever they want to say and give that person space. And you can kind of see the. Not just with the way I dress or the way I carry myself. There's good days and there's bad days, and you can kind of tell when I'm having a bad day because everything kind of externally changes. And it's funny you mentioned being five. I was five and very quiet. But I would just look at folks and kind of analyze and feel them and sense them. And I didn't quite understand how to tell that to my grandma because my grandma is very old fashioned, you know, she's 60 and I'm 4 and she adopted me. How do I tell my Cuban grandma, hey, grandma, I can see and feel everything. She'll just smack me and go, you're just possessed. How does, how do. Now that it's the year 2026, there is a lot less possessions and a lot more mental health mindset, generational trauma. How can someone like myself, that is on that search of self discovery, reach you and find you? And what are some keywords that I can use to communicate to you better that I need help?
Hillary Cheney
Right. I would say a lot of people say exhaustion. A lot of people say I'm at my limit. A lot of people say, I just can't. I can't even. And you shut it down. And whenever I'm planning to come to Miami for filming or to show up at a court case or to show up for something, I have to have a backup. I have to have. I can shut it all down. And that means just go in my room, shut it down, turn off the phone, and if you just say, I can't anymore, I'm done. But also letting people know, when I started talking about bipolar, I was in a small Baptist southern town. And to talk about bipolar and the things I felt about religion and bipolar was like, what is she doing? She is possessed. And so to have the courage to be like, so. So many other people you see have severe mental illness diagnosed undiagnosed. And when you say that, when you say I'm struggling today with depression, with mania, with psychosis, and you say that, I think you'll be blown away that people open up and they help. People are helpers. People have the gold. And I think most people will probably try and help you if you're really struggling. I remember flying back from Chicago one time when I was by myself and I was manic and I had to get back to the hospital and my doctors really quick and I was so tired, slept for days and I just went under the flight attendants, I said, I am not a real person right now. Can you help? And they were like, we'll give you extra seats and here's some blankets and here's some headphones, like people see if you're distressed. And I think most people have that gold in them. Now. This world has some very mean people and some very people that do not understand or sympathize with divergence. But you'll recognize, you know, the people that are safe, right?
Ray Gutierrez
Yeah, yeah, yeah, for sure. It's. And it's kind of difficult because, well, you must be good looking because things must be easy for you. Oh, you don't have a problem. Like, no, dude. Like at the end of the day, we're looking at a microphone and a slate and it's all these futons compressed together to create reality. And sometimes folks like you, you and I are receptive to all sorts of frequencies, be it positive or negative. And. And it's us to go, there's a bad energy here. I my. I'm destined to fix this. And the majority of folks can't even understand what we feel and see. We really have quite the responsibility on our shoulders and we've. I hate to compare oranges, apples to oranges, but that's a terrible thing to compare. But loss is a. And trauma is very powerful thing that teaches us and molds us. And it's our job as human beings to kind of see the light in the darkness. How do you keep people motivated to continue finding that light, knowing that this is an incurable disease? But it's something that is part of the human experience, right?
Hillary Cheney
Well, it has been talking about it. I wrote a book about it to help other people with bipolar. It's called through the Open Door. It's on Amazon. Hillary Cheney and so that gives tips and tools for people that are going through it or families. I love having a stable of people that are professionals in my life that I Can count on and trust that I pay money to help me. Accountant, lawyer. I love power women. So they're all women. Real estate agent, property manager for my houses, financial advisor. All those people trust me. They know me, I trust them. They get my mania. They still work with me and use that stable and refer my friends to them. I have like, success stories of people. I've said, okay, you're in dire straits financially. Go see Robin at Ameriprise. Go see my financial planner and go see her and talk to her. And they come out and they're like, I have financial freedom and peace. Oh, my goodness, I can't believe I do it. So referring people to those actual living people who have helped me in Little Rock. I love it. I feel so good about it because it's helped me. If I try and invent the wheel every time I have a problem with my kid, with my work, with my houses, I will have no time. I will not sleep. I will have no time. So farming it out. Another thing that helped me. I was terribly afraid financially when we were negative $300,000 in debt and terrified of just bankruptcy and not eating and not having anywhere to sleep and all that. And somebody told me, good debt builds wealth. And that's scary to think of, like taking this, you know, $500 and putting into something that will start to earn for you. But that mentality of, like, spending smart money to build is where I am to financially have the freedom and peace that I have. And having. That's the monster. Not having money is the monster under my bed.
Ray Gutierrez
Yep.
Hillary Cheney
So when I tackle that problem, getting a credit counselor and getting a financial planner, the monster's gone. And so I can succeed.
Ray Gutierrez
It's brilliant how you're in this. I'm currently in that phase as well, where I have a financial advisor or someone that's going to regurgitate my. Regurgitate, terrible word.
Podcast Producer
Re.
Ray Gutierrez
Enhance my credit and just kind of build these safe zones for I can just create, feel at peace and everyone's happy. And it's so important to have that tribe, especially a tribe that is one less voice in your head that's. That's gnawing at your brain, keeping you up at night about tax or about this or about that. Now you can kind of spread that energy to your team, your home base that's keeping you protected. How does one learn that? Did you just go to Tony Robbins convention or did you just have this divine download and you kind of express yourself and you're just following your God?
Hillary Cheney
I just knew When I needed help and I knew my family's in Virginia, I'm in Arkansas, I knew that I needed to really do it on my own with my husband and, and friends around me, because family is limited. Family is limited in the skill set, in the patience, in understanding who you are, in having lived long feelings about who you were when you were four. So family was kind of limited in helping me. I was like, who are the pros that have trained in this, that are specifically knowledgeable in this area that I could use? And as a lawyer, I think I was trained to go to the source of knowledge, because as a lawyer, you might not know what the heck you're talking about. You say, I will find the answer. People say, well, how do I do this, like, legal case of like, child support? I don't know. I'll find the answer. And so as a lawyer and a law student, you were trained to go hunt down answers. And I was trying to do that and spinning my wheels and going in debt and all this stuff. And then I was like, oh, hire people to find the answer. And then that gives me time to look on my phone, on Zillow and scroll for new houses to buy.
Ray Gutierrez
Yeah, you're. You're getting yourself out of the work and you're doing things that are just going to enhance the entire tribe and kind of enhance your entrepreneurial journey.
Hillary Cheney
Well, and I still, you know, and what I did, and my kids are around, and they're so funny because I did get to start my real estate business with life insurance money after my husband passed. And everybody was like, well, your husband died. How can you say you're a mogul from that? Well, it was awful. It was horrible. It was the love of my life. But I smartly took that money and used good debt to build wealth and my team to say, these are chances to diversify your portfolio and give you rent income for life and help stabilize your kids finances. And so my kids are like, well, you have a real estate money. It's not like you started from scratch. I'm like, well, how is that? I mean, it was awful. I still used money to like, support myself and my family, but my kids would never.
Ray Gutierrez
I was gonna say you mentioned Star Wars. I'm like, it's like saying Luke Skywalker sat in Tatooine, but Luke didn't have to build tattooing.
Hillary Cheney
You don't start from like the bat.
Ray Gutierrez
But I completely agree because I do have kind of like my war chest. And, and, and to your point, I'm like, it's going into production. This. This investment is going to make me more money, and it's just going to go into production. Yes, it is a home, but I foresee it as a home that is going now into production because now it's going to just be a life of its own. Generate and generate where it's just on autopilot. And then I can go, okay, cool. This. This monster underneath the bed, the really evil monster, the drought of. Of. Of. Of financial freedom is underneath everyone's bed. And now that I kind of can quiet him down or her, I have the ability to just be at peace and create. And when you're creating in that mindset, it's all energy, and you can kind of see it gravitate and magnetize.
Hillary Cheney
Well, and that is so true about little, like, finding the golden people. When I even, like, we have these Facebook groups. I use Facebook a lot for, like, local groups, local realtors, local, you know, moms, whatever. And if I find somebody there that's going to help me, I give them feedback. I say, I love you. I, this has been awesome. 5 stars. Recommend you refer you to somebody else. So I'm spinning this little, like, wheelhouse of good people that I trust and building their own financial freedom. And when I found out that I was putting food on people's tables with my real estate industry and, like, my realtor was making money off me, my property manager, and I was, like, helping feed their kids, it was the best feeling. That was even more than, like, cashing the money every month, was knowing I was this little enterprise that was chugging along.
Ray Gutierrez
No, I completely agree, because even sitting here doing this podcast, I understand that there's XYZ of folks that are going to grab this podcast, edit it, but those folks are now eating their families and even the casting process getting you this chair. We are quite the tribe. And it all just comes down to this very moment, sitting in front of these microphones and having this conversation, knowing that there is this entire family that is supporting us and supporting you. How can someone start building that family? How did you build your first follower, your first client?
Hillary Cheney
So I guess I'm not sure I really have clients because I'm buying the houses and then renting them out. So I would say followers maybe are the people that my book helped. And so I started doing public speaking just in Arkansas, to lawyers and judges and counselors and all that about recognizing bipolar symptoms, how to help family, all that. And people would just message me on Facebook like, my daughter is bipolar and she's on Lithium. What should I do? And I love the personal touch and the catharsis of helping others. So any followers were like seeing I was bipolar and could maybe help them with their situation and that just fed me for a while. That was like 10 or 12 years ago. So then we fast forward to Nathan passing from cancer and real estate. I haven't needed outside investors. I've. I've just done it on my own and used a home equity line of credit that I just keep using and paying off and using and paying off.
Ray Gutierrez
I'm working on that one.
Hillary Cheney
So I know it is very clever
Ray Gutierrez
folks going, how do you make this work?
Hillary Cheney
I know that's why you have a
Ray Gutierrez
tax accountant, tax strategist.
Hillary Cheney
Kimberly Brake, a power woman.
Ray Gutierrez
Oh yeah, I completely agree. I need the feminine, powerful, powerful touch energy. Yeah, it's very, very important. Trust me, I'm more than enough masculine energy. Well, I would say a lot more feminine than masculine, but anyways, that's a completely different podcast. That being said, where does your power derive from? Where do you think your power comes from? Is it your legacy? Is it your day to day? Is it your Zillow postings? Where does your power as a woman come from?
Hillary Cheney
I think it's that I've always been a competitor. I played on little league, little league, boys baseball teams. I, you know, won tennis tournaments when I in the city of Norfolk, when I never played on a high school team. I just was a competitive athlete, tomboy, all that and just wanted to win. I loved winning, I loved competing, I loved coming from behind, I loved being the, you know, underdog. So that sports mentality took me through the rest of my life and I truly have been the underdog. Like I have been pummeled down psychiatric hospital and debt and cancer caretaker and widow. Like I am used to being the underdog and I just get excited when I'm the underdog. I just get a thrill of like, you haven't seen nothing yet. Wait till you see what I can do with this. And so it's competitive and it's ego. And I, so many of us in like the modern day say, oh, ego is bad or we, we're not as, you know, look at other people and value other people more or value a spirit more or something like that. Ego is us. Ego is what we have and what we need to drive and feed ourselves every day and wake up and do. And so I've never looked at ego. Am I confident? Absolutely. Do I take advantage of other people because of it? No. But I think having that Ego in your heart is the driver. Like, don't be afraid of that. Don't. Mandela said, shine your light so others may shine. And that's that golden core I see in other people. I see in you and my kids and the people that are producing this show and all that.
Ray Gutierrez
Right on. Well, I appreciate the affirmation and the recognition for that. Hillary. How can people learn more about you and discover your journey?
Hillary Cheney
Sure. Okay, so there is the website hilarybeth honey.com and that has a blog and my real estate portfolio and it has a newsletter with some tidbits and helpful tools and that kind of thing. And then it's a link to my book through the open door on Amazon. They can find me on those socials, Hilarybeth Honey on Instagram and TikTok and the socials. And you can also just look on my regular socials, which are Hilary Martin, Martin Chaney or Hillary Cheney, and contact me and email me, message me, whatever. I love to help people. I love to tell you about, like, like I said, like, that lithium dose seems a little high. I'm not a doctor, but if you're doing, you know, I love that little conversation with people. So, Hillary B. Honey, it's H I L A R Y B E T H Honey. Hillary Beth honey.
Ray Gutierrez
Hillary Beth, honey. All right, well, thank you so much for your time and energy. We're, we're literally going to walk down the hall and film your episode.
Podcast Producer
Okay.
Ray Gutierrez
Right on. Well, thank you so much for your time. Thank you. Rick Lillary.
Narrator
Beth honey.
Ray Gutierrez
And I am Ray, not Beth Gutierrez. And we are inside. Success.
Hillary Cheney
Thank you.
Ray Gutierrez
Thank you.
Host: Ray Gutierrez
Guest: Hillary Cheney
Date: June 19, 2026
This episode of Living Your Legacy features an in-depth conversation with Hillary Cheney, a resilient real estate investor, federal law clerk, and advocate for mental health awareness. Hillary shares her extraordinary journey from personal and financial tragedy—including a bipolar disorder diagnosis and the loss of her husband—to building significant success in real estate. The episode centers on themes of overcoming trauma, the power of discipline and consistency, and the importance of leveraging support systems and professional networks. Listeners are encouraged by Hillary’s candid discussion of mental health, resilience, and how she uses her experiences to empower others.
Diagnosis & Early Struggles (00:00, 02:27, 06:05)
Loss and Recovery
Mantras for Success (00:00, 02:27)
Building Wealth through Smart Debt (00:43, 13:59)
Life Insurance as Seed Capital (17:42)
Impact on Others and Community (19:19)
On overcoming financial fear:
On mental health transparency:
On ego and competitive drive:
On building community impact:
The episode is insightfully candid, heartfelt, and empowering—Hillary and Ray speak with warmth, authenticity, and encouragement. Listeners are left with practical insights, real-life guidance, and a strong sense of resilience in the face of adversity.