From Denny’s Waitress to Real Estate Rockstar with Dwan Bent-Twyford | 642

MORI 642 | Waitress to Real Estate Rockstar


Today’s guest shares a fascinating and inspiring story of going from waitress to real estate rockstar. Joining Chris Miles in this episode is Dwan Bent-Twyford, affectionately known as the “Queen of Short Sales®.” Dawn is the Co-Founder of, the host of The Most Dwanderful Real Estate Podcast Ever, and is considered the Nation’s #1 Expert on Short Sales & Foreclosures. There have been plenty of ups and downs in her real estate journey, and she’s here to share the most important takeaways, so you don’t have to make the same mistakes. Learn all about Dwan’s wonderful rise to real estate success by tuning in to this episode!

Watch the episode here


Listen to the podcast here


From Denny’s Waitress to Real Estate Rockstar with Dwan Bent-Twyford

Welcome to our show. It’s for you. Those that work so hard for your money, you want your money start working harder for you right now. You want that freedom and prosperity today, not 30 or 40 years from now so you live in that life that you love with those you love. Most importantly, it’s not about getting rich or living a rich life because as you are blessed financially, you have a greater capacity to bless the lives of others and create that ripple effect.

Thank you so much for allowing me to create this ripple effect through you. Thank you for reading, bingeing and doing all the cool stuff you do. As a reminder, if you haven’t done so already, go to Check out the Passive Income Calculator. If you want to find out how much passive income you can create in the next twelve months, go check that out.

I have a special guest that I’ve enjoyed being able to get to know better and I know you will too. I was on her show recently. If you want to check it out, it’s The Most Dwanderful Real Estate Podcast Ever! I have Dwan Bent-Twyford here. She is an amazing woman. She has been in real estate for decades. Just like us where we’ve had the experience doing that kind of thing, we’ve been around the block. I’m amazed at her wisdom. I love her personality. I had to share her with you too. Dwan, welcome to our show.

Thanks for having me. I’m so excited to be on your show, Chris.

I already know. I got a sneak peek a little bit and get to know you a little bit off the air and even on the air. Tell us more about your story and who you are.

I started real estate investing over 30 years ago. Sometimes, I’m like, “Where did 30 years even go?” I was married. I had a baby. My husband and I had a pretty sudden breakup. I’m 30 years old. I have an eight-month-old baby. I have no money, job, car or career. I waited tables and stuff like that. I had to figure out some way to make money and raise my daughter. One thing I did not want to do is to raise her in daycare. I waited until I was older to have kids so that I could be the stay-at-home mom, the room mom, the Girl Scout mom, the brownie mom and all this stuff like that. I had to put on my big girl pants and figure something out. As it turned out, God led me to real estate investing.

At the very moment when my husband left, I thought this is the worst thing that’s ever happened in my entire life. Now I’m like, “I cannot even believe 30 years have gone by.” I’ve done over 2,000 deals personally. My husband and I own twenty buildings in a little town where they’re doing a downtown rejuvenation thing. In the last five years, we bought about twenty buildings in this little town. It was like fixing up a whole town. I could never even imagine in my life I would ever do this or have this much money or success. God puts you on the path sometimes and you have no idea what’s going to happen at the other end.

If we could all learn from that one lesson alone, whatever misfortune we’re going through sucks and is not easy but usually, those doors all close on us for a reason because it opens up that new path, the door that we may never have considered in the first place.

That’s what I always tell people. I’m like, “Everybody in their life has some come-to-Jesus moment and that was mine. My husband’s gone. I got a kid. I have no money, car or education. I was wowed. It’s 1990. I was like, “What am I going to do?” I met a few people and this is what they were doing. I thought, “It looks like fun. They’re fixing up houses. I could do that.” The next thing you know, it’s 30 years later.

I’m sure you’ve heard this time and time again. Many people will say things like, “What if real estate crashes or goes down? What if this or that?” I remember the last recession was horrible. Many people are gun-shy with real estate, even after many years of it being awesome. You’ve been through multiple recessions like I have and you’ve even experienced some more, as a single mom even. That was right before a recession hit too.

I wasn’t smart enough back then to pay attention to things like that. When we were in a recession, I didn’t even know. Ignorance is bliss sometimes.

We didn’t have Facebook and social media. The way the media works today where you get to hear all this stuff wasn’t the same. Based on your experience, how do you feel about real estate? How’s it worked for you?

People before the money, then the money comes. Click To Tweet

Real estate investing is one of those things that every single person can do it. I always tell people, “There’s someone that’s too Black, too White, too young, too old, too tall or too short. No person can’t invest in real estate. You don’t even have to have tons of education to start.” With everything available today on social media right on our phones, it’s crazy to not have some education but I started with no knowledge of any of it.

In the first house, the people I met were rehabbing and they’re like, “We buy houses, fix them up and sell them.” In my naive mind, I thought that meant decorating. Truly from the bottom of my soul, I thought I was buying a house, decorating it, selling it and making money. I had no idea that rehabbing and decorating were not the same thing. If someone can start like that and still become successful, I don’t think anybody else has any excuses.

In the back of that, mauve was still the color. I put it on some mauve carpet. I knew how to paint so I painted the house and the outside of the house. I painted it what I thought was mauve but it ended up being like Barbie doll pink. I decorated it and thought, “This house’s kitchen is terrible. It needs so much work.” I went to Home Depot and took those classes. I go back and work on the house. I rehabbed that whole house by myself.

I look back on that and it’s like, “I had no knowledge and skill. I just felt like this is what I should be doing.” I made $22,000 on my 1st deal. In 1991, that’s a lot of money still but back then, that was the most of my money I had ever seen. I didn’t even know anyone that had that kind of money. I was like, “I’m rich. I can’t believe it. I’m going to do it again.” I did it again and again. I’m making $20,000, $30,000 or $40,000 on each of these deals. I found some secrets.

You made more than you’d make as a waitress.

I got fired from Denny’s. I used to wait for Denny’s on the third shift, from 10:00 at night until 6:00 in the morning. I got fired at 3:45 one day. That girl that worked there was like, “All you do is tell other people how to do their job better,” but I can see. I needed to be an entrepreneur with that. I only didn’t know it.

You wanted to run the Denny’s. You didn’t want to be the one working on it.

I don’t like people telling me what to do and it’s not even that I don’t like to follow orders. I do have the ability. I can look at someone’s business up here and look. I can see the things that needed to be fixed or worked on. In our lives, we don’t see the things that are right in front of us sometimes but I do have a good ability to do that. Every place I worked, I was always telling the bosses, “If you would do this or this, your company would have run better.” They would be like, “You’re the waitress. You’re telling me how to run my company.” I’m like, “If you’d do what I’m telling you to do, you’d be better.” That’s seen as being insubordinate.

It’s because you’re bossing around the boss. Even though you’re not bossing them around, you’re only giving them suggestions like, “If we fix this, this will be better.”

I got fired from quite a few jobs in my twenties for always telling the boss what they need to be doing better. That’s why I was an entrepreneur, I just didn’t know. Ever since I started working with myself, I’ve never been fired.

Was real estate your first venture into entrepreneurship then?

It was. In my twenties, I did sales jobs. We work on commission. That gets you a little bit of taste in earning what you make. You can work for what you want to make but to go into real estate investing like that, there was no boss or nobody than me. I had to figure out the money and the deals all out by myself but I liked it and the business. What I liked is I was buying houses and knocking on doors back then. I would talk to people that were in foreclosure. I noticed there were a lot of women where the husbands and the wife had split up and the woman’s living there and she’s got the kids.

MORI 642 | Waitress to Real Estate Rockstar
Waitress to Real Estate Rockstar: Real estate investing is one of those things where every single person can do it. There’s no person that can’t invest in real estate.


I was like, “I’m in the same situation. My husband took off. I’ve got the kid. I lost my house and my car. I lost all my things too.” I had a heart for these people because I understood their pain. The next thing you know, I was doing deals and deals. I then started wholesaling and I’ve done 50 deals every single year. I was always working with people. Even today, I still always like to work with people that are in foreclosure or distress. That’s where my heart’s at because that’s how I started myself.

I have a heart for people and I feel their pain. All these years later, we bought some buildings that I was selling recently but all of them came from people that were in distress. They were couples. He owned the building and the husband passed away. The wife didn’t want it. She’s older and wants to retire. She’s like, “We don’t know whom to trust.” I’m like, “I’ll take care of you.” All these years later, I still always want to help everybody.

I’m sure the readers get tired of me saying this all the time because the big mantra that changed everything for me was understanding that eternal principle that dollars follow value. It is always about how you go about serving people and solving problems for them and adding value in a way that money is the natural by-product.

I say, “People before profits.” “What’s your mission statement of your business?” When people write these mission statements, they’re like, “That’s long.” I’m like, “Are you ready to write this down? It’s, ‘People before profits.’” That’s the whole thing. I used to have this big old long mission statement. I’m like, “Who reads those?” It’s all about people but people before the money, then the money comes.

“You’re like a landlord in a sense. You’re trying to screw people over by making a buck off of them based on their desperate and dire situation.” When you hear people say that stuff, what’s your response?

I usually say, “Do you own or do you rent?” I’ve had it in the past. “Did you need a place to rent?” “I did.” “If that landlord wasn’t there, where would you have lived?” A lot of people are not a big fan of this but I am a big fan of the Section 8 program. Most people don’t know what it’s meant. They think, “It’s a bunch of people mooching off the government.” The program is designed mostly by women and multiple kids to pay the rent and the bills. The woman gets to go to college.

When she gets a degree, she gets a job and the government takes out $50 a week out of her check and they match the money. When they have enough money, they’re guaranteed to get an FHA loan. It’s designed to help someone that can’t do it go through college, get a degree, get a job, buy a house and work in the system. Ninety percent of people mooched off the system because that’s just not what people are. All the women that have rented for me, I always make sure in the college program doing the program.

You’re not teaching them but you’re encouraging them. You’re incentivizing them to say, “I want you to lift yourself out of poverty. I want you to be able to have ownership and have your own life.”

When my husband took off, I’m 30 but my family was from Ohio and the very first thing my dad was like, “Come back. You can live in your old bedroom. You don’t have to pay rent. Come home.” I’m thinking, “I live in Florida. Do I want to go live in my old high school bedroom with my dad or do I want to jump in the ocean and pray that a shark eats me?”

Being eaten by a shark seemed like a better option. I was like, “I don’t want to tuck my tail and go home. I have to figure something out where I’m not going to keep getting fired from jobs.” When I meet people and they want to rent from me, I do qualify to make sure. Some lifers take advantage of the welfare system. They teach their kids and their grandkids. It’s like a lifestyle.

Some people are trying to lift themselves and better themselves. I’m like, “God blessed me with a great business. If I can bless you, give you a place to raise your kids, get you into college and get out of the system you’re in, I’m all for doing that.” What happens is they live in your house for a decade and when they’re ready to buy a house, they want to buy your house. It’s like, “No. It was my favorite rental. I’ve lived here. I went to college and have been raising my kid. I want to buy this house.” I’ve sold a bunch of my rentals to the people that were renting from me.

That home continues, doesn’t it?

It's so easy to make money the right way in real estate. Click To Tweet

Yes. The first one that wanted to do that I was like, “No. I love this house.” It was one of my rentals they had for a long time. She was like, “I have the money and I’m guaranteed. I want to buy your house.” I was like, “All right.” The next one comes and I was like, “Dang.” I sell them to the people. If they go through all that and they can afford to buy a house, the government will do FHA or whatever it appraises for. They’ll help them with the loan and they’re guaranteed.

I find it fascinating that it’s almost like the story of your life gets reflected in the lives of the people that you’ve either rented or soldier homes too. It’s like, “I get you. I’ve been there. I’ve had to pull myself up by my bootstraps and be able to take it through my life. You’re doing the same.”

We have all these commercial buildings and we’re working to flip this town around. I told my husband, “Nobody is going to want to buy one of our buildings. We’re going to stay.” The answer is no. These are commercials. I don’t care if you have a business there. I’m not selling my buildings.

Tell us about where you’re at. Describe your life and how you do real estate investing today versus when you started.

I started rehabbing and then discovered wholesaling. I was like, “You can make so much more money without all that physical work.” I wholesaled for a while and then got a REIA group. I wrote a book and it was a bestseller. I was asked to write a second book and it was a bestseller. I had an infomercial. I was on TV and all these things. I always was buying rentals. I mostly wholesaled and have rentals for a while. My husband is from Clinton, Iowa. We go back to reunions at my hometown and his hometown. I’m like, “I wish to buy something here.”

It’s like an old downtown on the river that time forgot. We started finding out how much money is available in these opportunity zones. All these re-beautifications in these little towns have millions of dollars grants for everything. I was like, “We should do this.” We bought a building. We are the go big or go home people. We bought a 2nd, 3rd and 4th building. Now, twenty buildings. We have to stop and fix up everything that we have.

My career is a progression of me getting into bigger things as I go. I always find myself getting into the next thing but still at my core, we still wholesaled 30 houses in 2021. I still love my Section 8 tenants. I’m keeping all my tenants. In these last few years, we did vacant land and a storage unit, which I had not done. We bought some land and put a couple of spec houses on there and did that.

In the last 10 years, I’ve done some things I had not done before. A lot of that is I have the money, first of all, but also, I have so many people like you and people I’ve met whom I’ve been exposed to. I can call and ask people for help. Whereas when I started, there were no regroups and internet. You had to drive to the courthouse, write down addresses and use a map book to get the houses.

I didn’t have anyone that could teach me other things besides the basic flipping, wholesaling or rehabbing. Over the years, I’ve done a lot more because I have access to people. There are things online, people like you and people I could call and say, “I want to do this. What do I need to do?” We do bigger things all the time but with everybody, I always learn, pay for training or educate myself. I don’t just go wing it as I did in the beginning.

If you think about it, it’s easier today to succeed than it ever has been. It’s cool.

I had been being a guest. I had been on over 100 episodes. For some reason in my mind, maybe it’s my age, I was like, “I don’t guest.” It’s like a show on the computer or radio. I couldn’t wrap my mind but after I was on it for a while, I liked this show so I’m going to start with the podcast. Even for that, I did 30 lessons and 30 days of homework. I took a whole class and several classes. I went and bought all the right stuff. I didn’t just wing it but I took the education.

You learn from either mistakes or mentors. Mistakes can bankrupt you. The mentor may cost you money but it is to purposely cut your learning curve. I tell people, “Mistakes and mentors, I learned all by mistakes in the beginning. Mentors are cheaper.” Anything I want to learn, I find the person and take a class or whatever I need to do to learn it. I already know that the school of hard knocks was a long learning curve. I had a decade of the learning curve.

MORI 642 | Waitress to Real Estate Rockstar
Waitress to Real Estate Rockstar: If you want to get involved in anything in real estate, get on some webinars, read some books, find some people that do what you do, make sure your moral compass aligns with that person, and they’re going to teach you to do what they do.


If you think education is expensive, try ignorance. It’s even more.

I started in the ‘90s. Even by 2000, people were starting to have computers at home but still, nothing was like it is now. I didn’t have any mentors. I remember buying houses that have fire damage, water damage, termite damage and all these different things that I had no idea what it was. I buy the house, go to rehab and find out that one house was decimated by termites but it costs me $30,000 extra dollars. I had to borrow money. I couldn’t even do the deal because there were so many things I didn’t know. My learning curve was long. I like to teach and help people. I was like, “You work with me. I can cut your learning curve. You won’t make any bonehead mistakes. Ask me a question and I’ll help you.”

Along those lines, we’ve got people here that have a variety of experiences. Some have done real estate and other types of alternative investments but there are a lot of people here who are learning and trying to understand it. What would be your advice to them?

They should go to, opt in and get some free books. That’s first. Chris, I always tell people, whether you learn from me, you or somebody else, if you want to get involved in anything in real estate, get on some webinars, read some books, find some people that do what you do and make sure your moral compass aligns with that person. If you feel like that person runs a good ethical business and you feel good about what they do, they’re going to teach you to do what they do.

With all my students, I’m like, “If I ever hear about you going around somebody or an investor, screwing a homeowner or anything, I will bring you up on charges. None of that business is going to go on.” There are always those who scam people on the internet or paper. They’re like, “This one was arrested for scamming some amount of money.” It’s so easy to make money the right way in real estate. You don’t need to do anything bad.

Dwan, thank you so much for being so generous and giving us your experience, your wisdom and even your inspiration too. It’s awesome to see that.

I appreciate you having me on. This guy is so great. You got to follow him, listen and do what he tells you to do.

The thing is that you can try to do this yourself forever or the long and hard way like many of us did but the great thing is that you have control and better resources to dispose of for greater education and ability. The question is, “What are you going to do with education? Are you going to take action with it or are you going to let time and your life slip on by?” Make it a wonderful prosperous week. We’ll see you later.


Important Links


About Dwan Bent-Twyford

MORI 642 | Waitress to Real Estate RockstarDwan is affectionately known as the “Queen of Short Sales®” and is considered to be the Nation’s #1 Expert on Short Sales & Foreclosures.

In fact, Dwan wrote the FIRST short sale, real estate investing program for investors back in the 90’s and went on to coin and trademark this terminology as well as present the Short Sale concept to the real estate investing world!

She has written three best sellers, “Short Sale Pre-Foreclosure Investing” & “How to Sell a House When It’s Worth Less Than the Mortgage”, her most recent New York Times best seller was written with Steve Forbes…SuccessOnomics.

She is highly sought after and has been featured on Fox and Friends, MSNBC, Naomi’s Good Morning, Colorado and Company, and many other TV, radio, 100’s of podcasts, and print medias.