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This investor bought her first property when she was making only 20 grand a year. Now she generates $50,000 in cash flow per month just from her real estate portfolio. That is financial freedom. And she achieved it by just buying the same types of properties over and over. And now she's using that freedom to completely transform her life and her health for the better. Let's hear exactly how she did it. Hey, everyone. I'm DAV Meyer. I'm a housing market analyst and I've been an investor myself for the last 15 years. And on this podcast, the Bigger Pockets Real Estate Podcast, we teach you how to achieve financial freedom through real estate investing. Today's guest on the show is investor Ashley Hamilton. She lives and invests in Detroit and is one of the all time most popular podcast guests we've ever had. Ashley started her investing career when she was struggling as a waitress with two kids and slowly grew to 10 properties when she first came onto the podcast back in 2019. Today, we're having her back on for an update because she has accomplished a lot. Ashley has grown her portfolio to 40 properties today, but she's focused on maximizing the cash flow she can get with a relatively manageable number of properties instead of just trying to scale to as many doors as possible. And most importantly, she's using her real estate and the time freedom it has allowed her to to make huge improvements to other areas of her life. Ashley is going to share all about a huge personal health journey that was only possible because she took that first step and bought a property more than a decade ago. This is a super inspiring and fun story of how real estate can change more than just your bank account. Let's bring on Ashley. Ashley, welcome Back to the BiggerPockets podcast for your third appearance. Thank you so much for being here as well.
B
Of course, of course. I'm super excited to be here. And I cannot believe three times. Omg. This one's gonna be the best.
A
Yeah, I think we're gonna make it the best. We have big shoes to fill though. You've had some great episodes on the BiggerPockets podcast before, but maybe for people who haven't listened to those first two episodes, fill us in. How did you get into real estate in the first place?
B
Absolutely. Yep. So at age 23 years old, I found myself as a single mother of two kids under five. In 2009, I was 22 years old and had no business owners in the family, not even a homeowner myself. But I knew I wanted more and I didn't Want to feed into the statistics that have been labeled on me. So basically, I went to a webinar or a free live event here locally in Detroit. And I didn't know anything about real estate, but it was trying to get us to invest in real estate. Long story short, I sat through the whole three hour presentation, and out of everything, only two things stuck out to me, right? Be fearful when others are greedy and be greedy when others are fearful. And the other one was, be willing to spend a couple of years of your life living how most people won't, so you can spend the rest of your life living how most people don't. So that was all I took away from it. And then after I left the presentation, I started to look around me and I seen nothing but foreclosures, auction, HUD homes, bank foreclosure, because again, it was 2009. So I took that as a sign, you know, everybody. I cut on the radio and everybody said, don't buy in Detroit. It's a war zone. You know, you'll lose your shirt. The market is in the tanker. Real estate is bad. And then I see all the foreclosure sign. I was like, well, hey, this is a sign to do the opposite and be greedy when others are fearful.
A
Yeah, a lot of people were fearful in 2009 as pretty much everyone.
B
Yeah, for sure. So that's kind of what started it. But again, at that time, I was making less than $20,000 a year as a waitress at Red Lobster. Again, single parent of two. I had no real education or anything like that. So I didn't have any funds or resources to get started with real estate. Actually, the only time that I had ever seen $1,000 in my bank account was at tax time. Right? Once a year where the middle class and lower, you know, they would get a tax refund. So I knew I was expecting a $6,000 refund in 2009. So I said, hey, I look to use that to buy my first property.
A
And that was enough?
B
Yeah, absolutely.
A
How did you buy a first deal with a tax refund? How much was the deal you bought and what did you have to put down?
B
So that's the caveat, right? Everybody was like, oh, that's a great down payment. But how did you qualify for a mortgage? Well, the thing is, the house was $6,300. Like, that was it.
A
Oh, my God.
B
That was the purchase price. And obviously when I say that, people were thinking like, well, it had to be a rundown property. It needed, you know, a full remodel needed to be demolished. But no, actually it was this three bedroom ranch home right on the same street as a park close to 8 mile here in Detroit. So a very tree lined neighborhood and it needed about 3,000 worth of work like plumbing, paint and things like that. But. And now today this house is worth $130,000 today.
A
So yeah, I can't do that math in my head, but that's like 20 times the value. Something saying maybe the best return on equity I've ever heard on any deal. That's amazing. A very creative, obviously way to get into real estate and use the resources that you have even when they're limited, like you said. But figuring out a way to get started and take advantage of a time where a lot of people were scared. And I know everyone's probably thinking, oh man, it must have been so easy investing when things were 6,300 bucks to buy a house. And yeah, in retrospect it might be, but no one knew at that time that things were going to take off. Like people thought that the bott could take years. And actually if you start in 2009, the bottom didn't come for four more years. So it is, you know, practicing what you preach and being greedy when other people are fearful and sort of having the vision to invest even though things weren't as obvious as they might have seemed back in 2009.
B
Yeah, for sure, absolutely. So that property, like I said, it cost $6,300. And the crazy thing about it is I was getting $7,000 a year in cash flow, just off cash flow. Right. And then it did take a long time because actually I did not get my first mortgage in Detroit into 2019. So actually 10 years later, before banks really felt comfortable to start lending in Detroit and before the values to start going up. So it did take quite a long time. But at the same time, like I knew, you know, I mean, the numbers just made sense. I owned it free and clear. And even at seven grand a year, the expenses were very, very low because obviously if the Property is worth 6,300, the taxes aren't a lot, the insurance isn't a lot. So it just made sense. And I don't want to sound you, obviously we're talking about the past, but I don't want to discourage people that are watching this episode right now that wow, I can never do that with $6,300. Well, you can, you just have to use it as a down payment. Um, there's first time home buyer grants all over where they'll give you up to 25,000 in down payment assistance. And then obviously you can use people like hard money lenders and stuff. I know a lot of the lenders that I use, they, they're funding 90% of purchase, 90% of rehab. So you still could get into a property for around that price, you know, but you will be using leverage as well.
A
Yeah.
B
So don't want to disc anybody that's looking to invest now.
A
Now I imagine that probably changed your lifestyle quite a lot. Like you said, you were making less than 20 grand a year waiting tables. Then you go to making seven grand a year in cash flow. That's like I would imagine be a windfall. Did you use that to supplement your lifestyle or did you just use that to buy more property?
B
Right, and thanks for asking that question because a lot of investors don't talk about that even to this day. Like 80% of my income from businesses go directly back into the business. So when I was building from nothing dime I, I got. So for example, My rent was $700 a month. I, I still didn't change my lifestyle. I used $600 of that to invest and save up for my next property the following year. So that was the plan. Just buy a property every year using my tax return and then whatever, I can save monthly. So that's, that's what a lot of new investors I feel like, you know, don't understand. They buy a rental property and now they're like, oh, I can get a new car, you know, or I can go get the Tesla or you know, start to use the money for a lifestyle. And you can't do that when you're building. To me, my philosophy is the first three years, use all your income, you know, your profit and reinvest it into the business to build your solid foundation. And then you can start doing the lifestyle creep where, oh, I can afford a nicer car now, oh, I can afford, you know, to invest or save or do other things.
A
That is amazing advice. It's totally up to you. Like you could invest, buy one property and use it for lifestyle. But like the math is extremely clear. The longer you reinvest your money and if you can maximize your reinvestment and do that as long as you can, you will just get richer. And it's not even close. Like if you look at a compound interest calculator, for example, and you just google it, it's one of the most eye opening things I've ever seen in my life is like if you just see how much the Difference is, is even, you know, if you're making, let's say, seven grand a year in cash flow, the difference between reinvesting all seven grand and reinvesting two grand of that can be the difference of hundreds of thousands or even millions of dollars by the time you actually retire. And I know that sounds crazy, but it is really, really true. I recommend it. If you haven't done this before going to Google that. So actually, that sounds like a great scaling plan. You know, you're using your tax refunds, you're saving money. That's just good, fundamental real estate. Like, that's how most people do it. It's just taking what you got and putting it into it. But how did you scale quickly? Like, how did you go from buying one property a year to having a much more sizable portfolio like you do now?
B
Yeah, absolutely. So I have to give credit to the one and only BiggerPockets. And my first interview with David Green and Brandon Turner, of course. Yeah. So at the time of my first interview, I had 10 properties free and clear. I was semi retired. You know, all of I was living way below my means. And I thought that was it for me because that was my original goal. Not having any formal education, not knowing anything about real estate. I kind of just, you know, went in blindly. But after the first interview, you know, I got emanated with calls and messages. And then I got David Green's book about the bird strategy and things like that. And financing was possible in Detroit now in 2019. So I basically just said, hey, I'm going to give this thing another try. I started buying August of 2019. My interview came out May of 2019. And from August 2019 to August 2020, in the middle of COVID I bought 11 doors in just one year.
A
Picked a good time to jump back.
B
Yeah, it was like a collapsing time. So essentially took me 10 years to do. I was able to do in one year and even buy one extra door. And the biggest difference was using leverage. Right. So previously all of my deals were cash. It was sheer savings, investing all the cash flow and, you know, in working and things like that. But the second half was sheer leverage, you know. Now, to be honest and brutally honest, to give you guys something to think about. So my 10 property portfolio was generating probably around 4 grand a month at that time in cash flow. And then the 11 properties that I refinanced, they were only generating about $2,500 a month. So my free and clear portfolio was still kicking the butt of the leverage. But I Was still able to get way more doors, bigger net worth increase. So just that was to me a great case study that I even use today. Like how did my portfolio perform with Free and Clear and how has it affected me negatively or positively when I leveraged it? So I lost a little cash flow in there, but I was still making an additional 2,500amonth. Eleven properties, you know, versus the four grand off the 10 properties free and Clear.
A
That's a really important trade off for everyone to think about because there again, there's no right answer here. To me it really kind of comes down to where you are in your investing career. If you're trying to grow, it's often worth it to give up cash flow to acquire if they're good units, like great units that you want to hold on to for a long time. Because 2,500amonth, that's still a lot of money. You know, it pays for a lot of your life, but that will probably become five grand or you know, ten grand a month by the time time you truly retire and it's worth it. But of course there are risks, sort of and trade offs to, to carrying on that debt. My recommendation sounds like you believe the same thing is like as long as it's cash flowing and you like real cash flow, like not just like pretend social media cash flow, but like if you have real cash flow that allows you to take on debt in a responsible way. So that even if, like you said, if there's a rent freeze or you know, something adverse happens which does happen, these things do happen. Like if you can withstand that and use debt at the same time, can be a very powerful tool to scale.
B
I definitely agree with that and especially what you said about real numbers versus social media, like that is so important. The bigger pockets calculator. Like, you know, I've had people say, well I've used a bigger pockets calculator, but I don't have any cash flow. So I just did the numbers myself and I'm like, wait a second, no, that's not real cash flow. Right, you have to have the real cash flow. And then I've also had people say, well it's negative cash flowing but the appreciation or you know, and that's great. But again, just like Dave said, like once there's a rental freeze or just the inevitable happening, whether it's life or anything like that, you know, you cannot sustain, you know, having negative cash flow. So making sure that you use the real numbers for sure and that you're cash flowing even if it's a hundred bucks a month, it has to positively cash flow.
A
I couldn't agree more. I think people got into the appreciation, no cash flow thing in 2020 or whatever, which is a very unusual time. In real, you can't. That's probably not going to happen again. Maybe in our whole lives. Like we don't know. But it's very, very unusual from a historical perspective. So, like, I wouldn't personally count on that.
B
Absolutely.
A
I want to catch up though, Ashley, with what you're doing today, but we got to take a quick ad break. We'll be right back. They say real estate investing is passive, but if you've spent a Sunday night buried in spreadsheets, you know better. We hear it from investors all the time, spending hours every month sorting through receipts and bank transactions, trying to guess if you're making any money. And when tax season hits, it's like trying to solve a Rubik's cube blindfolded. But that is where Baselane comes in. BiggerPocket's official banking platform. It tags every rent payment and expense to the right property and schedule E category as you bank. So you get tax ready financial reports in real time, not at the end of the year. You can instantly see how each unit is performing where you're making money and losing money. And you can make changes while it actually still counts. So head over to baselane.com biggerpockets to start protecting your profits and get a special $100 bonus when you sign up. Thanks again to our sponsor, Baselane. So I tried explaining a sandwich lease to my insurance guy once and he just blinked at me like I made it up. And that's sort of the thing, right? Most insurance companies don't understand how we invest. You go vacant for a few weeks, you switch strategies, you hold stuff in llc, and suddenly your coverage doesn't fit. That's why I recommend National Real Estate Insurance Group. They actually get real estate investors. Their coverage adjusts as your property changes and you get one monthly bill for everything. No matter how weird your portfolio is, you can check them out@nreig.com bppod that's nreig.com bppod Most investors spend more time chasing deals than reviewing their insurance. But a quick coverage check can be fast, easy, and one of the smartest ways to protect and even improve your property's cash flow. As the months get colder, frozen pipes, icy walkways, and seasonal wear and tear can increase the likelihood of claims. And traditional insurance companies aren't always built to handle these claims quickly. Or smoothly. That's why more real estate investors are turning to steadily. They focus exclusively on landlords. Whether it's a single family rental, a Brrrr Builders risk policy or midterm holiday guests, you get fast quotes, flexible coverage and protection for property damage, liability and even loss of rental income. Now is the perfect time to review your rates and coverage. Get a quote in minutes@biggerpockets.com landlordinsurance steadily landlord insurance designed for the modern investor.
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B
So today I only own 45 properties.
A
That's a lot.
B
That's a lot, right? But if you're looking at social media and stuff, you know, I feel like a small girl in this, in this realm of real estate investing for social media. But what's most important is of that 45 properties, I'm cash flowing. $50,000 a month.
A
What?
B
And I'll break it down and I'm the queen of receipts. So, like, bring me back on and I'll open up some sheets for you or send some appraisals. But I love to show my receipts, and that's what kind of spearheaded this next journey that I'm on, being able to maximize cash flow without increasing the doors. So out of the 45 properties after my second interview with Big, bigger pockets in 2023, I doubled down with Airbnb. So right now I have five properties in the city of Detroit on Airbnb. And I know I say Airbnb because you can say short term rental, but I'm not gonna lie. Just with all the businesses I have, I'm strictly on Airbnb, so I could probably make more. So right Now I'm making $20,000 a month solely from, you know, Airbnb. And that's. I show it on my page every month, like the beginning of the month. I show what the previous month did and what the new month is expecting to do. So that's public information and it's not hidden. And what I would like to say is, even though I started an Airbnb In 2023, I started with one unit, I still use the same principles I did in my investment journey. So I have not taken a salary from my Airbnb earnings even to this day. And like I said, I Show I made $22,000 last for the month of August. And none of that went to me because I'm literally funding the sixth property strictly off the revenue from the five Airbnbs. So in about two months, though, the good thing about it is I'll be completely free of all debt from the Airbnb portfolio just because I'm generating so much. And then I have 15 section 8 rentals. Obviously, I started in 2020 converting, you know, all of my new rentals into Section 8. And that was strictly because the rental freeze, Section 8 was guaranteed. They were given incentives, and they were given about $200 more than market rent at that time. Yeah. So my Section 8 portfolio, it generates 25,000amonth. And then the reason I say that, because with the Airbnb, even though it's generating to 20,000, I have cleaning stuff like that, and just my regular, you know, our rental portfolio, that's just normally cash and some Section 8, but that's the portfolio. And out of the 45 properties, I only have four multifamily, which are duplexes. So most of them are single family.
A
Huh. You've invented and succeeded at a totally different approach to real estate investing. That I've ever even thought about. Like I think everyone goes through this stage where they, they are starting and they use leverage to grow and then later in their career they deleverage and pay down their mortgages so that they can get to free and clear but just from circumstances or intention. Like you did it the exact opposite way which is so awesome because you've basically with free and clear property that says every listen everything is risk. But a free and clear single family rental is about as low risk of an investment in the world world as you can probably create. And so you've created an income for yourself with almost no risk and now you're able to take on a little bit more risk because you have your essentially your lifestyle is just paid for on these low risk assets. It's so cool. I'm so jealous.
B
Don't be. That's okay. And like I have so much like, I mean because obviously it's all self taught but it's mostly listening to the market, listening to the knowledge and weeding out the, you know, the smoke and stuff like that and just figuring it out. Like one thing, what I noticed about my journey, I didn't know anything and that's what kind of got me to be more brave. Because if you, if you were in real estate before and you lost everything in 09, you would be scared or more cautious to invest but. Or if you had family members that did that. I didn't have anybody that was a real estate investor so I really didn't have those naysayers. So I just took it on. I didn't know what I was doing was really risky. But that's exactly right where you were, where you were getting at. I am able to take a little more risk now because I do have that nest egg, you know, building up.
A
That'S honestly super cool. I love it.
B
Really quickly I just wanted to talk about just some things that I've done. Just this is very new to me. This is the last year. So again and this is my market. I'm in Detroit obviously but I've seen this across plenty of markets. There's opportunities. So in Detroit the most popular asset class is a three bedroom one bathroom home. But I found out that in section eight they're paying $2,000 a month for four bedrooms and they have like 20,000 families that just are smaller units because there's not a lot of four bedrooms in Detroit. That was number one. So I studied for my builder's license. So I'm a certified licensed builder in the state of Michigan. Yes. So that taught me what a legal bedroom in Michigan was. And I said, wait a second, I can convert basements into legal bedrooms. All I have to do is add an egress window, which is about three to five thousand dollars. So long story short, to date I've turned five of my three bedroom single family homes into four bedrooms. Bedrooms by adding a legal bedroom in the basement. So with the five properties alone by me adding a fourth bedroom, I've been able to generate thirteen hundred dollars a month in additional cash flow.
A
Wow.
B
Additional cash flow just off that. So Basically what, a three bedroom would rent for about 1500 here, a four bedroom would rent from 18 to 2000, just depending on the demand. Right. So that's a huge jump. Probably cost me about 14 grand to install these new, you know, basically bedrooms. But that's the math on it. You have 14 grand and you're getting about 2 to $400 more a month in cash flow.
A
Okay. So even if you just did, if you took the average there, you're making 30. So it takes you like five years to repay that. So that's like a 20% return on investment. That's worth, I mean that's worth it all day.
B
And your appraisals coming back higher because now you have a finished basement. They may not include it as a bedroom, but a finished basement. I've, my appraisals have been blowing me away lately. I really want to make sure I talk about the property that appraised. The duplex that appraised for 135 in May 2024, that just praised that 360 one year later.
A
Wait, why 200 grand?
B
Yeah, I swear to God. So May of last year it appraised at 1:35. June of this year it applies at 360. Now all I did was I turned into an Airbnb. So it was furnished when I had the appraisal, but I just literally replaced all the windows and the siding on the exterior and furnished it. Really. Nothing major inside. And I added a bathroom in the basement. That was one way, you know, that I've been able to sustain and get more cash flow without buying more properties. I've also been converting duplexes because I own four multifamily properties. But they're two families, they're not like four or five. And I've been converted them into triplexes. But you may can even convert it to four plexes. And that's by adding a apartment in the basement. Right. Again, legal basement. Now that I know what A legal bedroom is like, I'm going crazy with this stuff. But if you're in a market that don't have a basement, you can maybe finish an attic on a duplex, because that's an opportunity as well. And basically. So now, again, in Michigan, normally if your property is zoned multifamily, they don't say two, three, or four. It's anything. Four units or less is the market. You know, two to four units in our zoning. So if it's already zoned multifamily, you can go up to four units without having to get the variance from the city, without having to really go through all the headaches, without having to put fire suppression systems. So that's what I've been doing. Like, how do I maximize this without having to break the bank by doing all this? This variances, waiting time and fire, you know, all that stuff. So my duplexes are already in multifamily zone area. So, hey, just throw a third apartment in there, a studio or one bedroom in the basement. And now I'm getting, you know, average rent maybe is 1100, but I can charge 900 for a basement apartment. And now I just increase. So If I'm getting 2,200 in rent for two units, now I'm getting 31 because I added $900 for that basement apartment. Still one tax bill, still one insurance bill, still one mortgage payment, but now I have three units.
A
That makes a lot of sense. And when you're considering these things, do you analyze it the same way you would analyze a different kind of investment? Because, like, we were kind of doing the back of the envelope, 20% return math, or like, how are you prioritizing these projects and deciding where to put your money?
B
Absolutely. So, number one, when I started, and I think that's what helped me so much when I started this in real estate investing, I knew it was a long haul. I knew it was for the long haul. I want my wealth to last 10 generations because that's what I feel like we've been missing. We weren't passed down generational wealth. So I always think of it, hey, this is going to be my forever home. My kids are going to own this. So I don't necessarily think, like, oh, you know what the appreciation is going to be. I'm looking at the neighborhoods, though. And then by me being in Detroit, I know that, you know, as long as it's clean, safe and decent, that there's going to be a big demand for the area. So that's basically what I'm looking at which properties are in the best area or, you know, I'm a licensed real estate agent so I can see if, I see if I'm just scrolling on Zillow and I see a home, home and a zip code that I own that sold for 160 and I'm like, wait a second, I paid 50,000 for a house that year. Then I'll start researching. I realized, oh, the value has increased significantly. So now let me put another bedroom in there or another apartment in there.
A
This is why I hate the idea of door count and like people comparing how many units they have. Because like, let's just say you had 20 grand. You could go buy another unit that produces 2% return or 5% return or you could do what Ashley's doing and that produces a 20% return return. What's better? The 20% return is better. Like there's, it's just math. Like that is just a better way to use your money. And if you just like get out of this social media mindset of comparing how many units you have, you can actually just make more money and have less stress, which is exactly what Ashley has accomplished here.
B
That's the goal. And I actually learned it because I never, you know, not saying like that, I never kind of worry about other people's portfolio and stuff, but I always felt like the little, the little girl in town because I didn't have as many doors. But when I met, I was in a mastermind with a guy who owned 150 doors and I was making like 8 grand more a month than him. So I'm like, at this, at this point it's like, big bank, take a little bank with me. That's just the game that we were playing. But I'll match your doors, but match my cash flow. And I want to see. I know nobody with 45 doors are doing what I'm doing at 50 grand a month, but for sure, like, let's match the cash flow. I guarantee you I'm competing with these people that have 150 doors that aren't making this much.
A
You know, it's funny, I wrote this in my book because I have the great privilege of speaking to investors every single day.
B
Yes.
A
And I don't have data on this, but anecdotally I will say that there is no correlation between how happy people are and how many units they own. None. It's like oftentimes more people I know have a lot more units. They're miserable. People have like 10 paid off units. They're pretty happy. You know, Like I think like that is a really important lesson is that it's not about unicount, it's about like the quality of life and if it allows you to sort of live the life that you want. Which is something I do want to talk to you about actually, because I understand real estate has allowed you to pursue some other interests and go on a new journey other than just real estate, which I want to hear about. But we got to take one more quick break. We'll be right back. Okay, let's say you're one property's mid flip ones between tenants. One's on Airbnb now try explaining that setup to a regular insurance company.
B
Company.
A
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B
It has changed my life in many more ways than I can even describe or even know. I'm still finding out new ways to change my life like last month. But number one, I was able to break generational curses, right? So when I first started, I was 22. My parents never owned a home. We didn't have any college graduates, no business owners. And I'm happy to say that I was 36 years old when my son graduated high school and I had two first generation college students. You know in my family that we were able to go to college and what's more important, they had college funds so they did not have to take out any student loans. They don't have any student loan debt to this day. So to be able to break generational curses, if that was all that I could have gotten from this, like I would have Been satisfied there. Right. Because now my family can look forward and actually be able to have an advantage in life versus starting off with a disadvantage like I started. So that was number one. Yeah. And at the same time, again, I found myself 37 years old with, I was an empty nester, two kids in college, and I'm just sitting here in this house and I'm like, I'm financially free. I'm a multimillionaire. What's next for me? Like, I don't even know who I am. I had never lived alone before because I was a single parent at night at 17. So I live with my parents and then I got an apartment with my kids. So I didn't know who I was. And actually my mom like had to call me and she was like, kind of like, hey, quit the pity, right? Pick your head up. You're 37 years old, multimillionaire. Like, I don't care what you do, just go live your life. You don't have any kids. I would have loved to do that. And I'm like, you're right. So obviously the first thing I wanted to do was to be a healthier individual. I was overweight my whole life. I was high blood pressure, pre diabetic and things like that. So I decided to adapt a plant based lifestyle and I was 100% strict. I was working out six times a week and cooking all of my meals and everything like that. And I just have to say, like, obviously you know, it's a great way to live, but everybody can't do that. But I had the luxury of not having any kids here by myself and already financially free without working a job. So, you know, it did take work, but it helped me be able to sustain that lifestyle. So long story short, after about a year of doing that, I've lost 100 pounds, over 200 pounds in my whole life, but 100 pounds, for sure.
A
Oh my God. Congratulations. That's unbelievable.
B
Thank you so much. Yeah, 90% of the people did not recognize me at BPCON last year.
A
That's unreal. Wow. Well, good for you. I mean, being healthy is, is in a lot of ways a luxury. You know, you need some money and you need time to be able to do it. Having the time, freedom and the financial freedom, I imagine sort of helped along that journey.
B
Yes, absolutely, for sure. Because it bought me back my time. But I really want to make sure I touch on this, Dave, because I feel like a lot of people don't talk about this, but. So when you're a real estate Investor. Now it's time to figure out how to save money. And we all know like taxes and insurance, how to protect yourself, especially with the insurance. So, so the first thing I did is once I had a million dollar portfolio, I wanted to go out and get life insurance just in case something happens to me while I'm building, the kids will be safe, they won't have to worry about these mortgages. And I didn't qualify for life insurance. I was overweight, high blood pressure, and people don't understand that. I mean the trashy kind, it's like 20, 50,000, but I needed two or three million dollars to cover everything and I couldn't qualify for that. So that's why I said I'm just learning stuff. Like recently the following year I was able to go get an exam and now I'm happy to see, say I have term life insurance and whole life insurance and I qualify. And even my heart rate was the same as an athlete, I'm like, what? So let's talk about that more. As far as health and wealth, you know, it goes hand in hand. But as investors, as entrepreneurs, if you look at the, the who dies from heart attacks most is CEOs, right? And business owners at a young age, right? The youngest age. So you're getting the 40 and 50 year old execs that are dying from heart attacks, even if they look healthy on the surface because of the stress and everything that's involved. So being able to qualify for our life insurance is a big item that we, I feel like we take for granted and we don't speak about it enough.
A
It is really cool to hear how this has evolved for you because I think it's, you know, a lot of people again, focus on unit count and how much money you're making or even cash flow. But like at the end of the day, no one really does this for cash flow, right? Like you want the thing that cash flow will get you, right? Whether that's more time, a healthier lifestyle to pursue a hobby that you're really interested in. Like that's the thing that most people want. But unfortunately it does seem like a lot of people lose sight of that and you kind of just like keep building, keep grinding and then never actually go after the thing that you really wanted in the first place, which, but it sounds like you have really like been able to do both at the same time, which is super impressive.
B
And I would just say it's because like, so I, I encourage myself to learn every single day, even from a two year old. I always want to learn, but I never stray away. What is good for me. So even when I did in 2019, when I decided to start leveraging my portfolio, I didn't go out and put mortgages on all 10 of my free and clear properties because that wasn't me. I still wanted to have free freedom. So it's easy to, when you hear podcasts like this or social media say, I'm gonna do what Ashley's doing. Which you should. Right? It's smart. No, I'm just joking. But you should, but you should still conform it to what your ultimate goals are.
A
I love it. I absolutely love it. Well, thank you. It sounds like we share a similar philosophy about approaching real estate. You've already accomplished a ton, Ashley. But like what, what's next for you? Are you going to continue sort of just optimizing the portfolio or what are your goals these days?
B
I'm continuing to optimize my portfolio. I do plan to buy because I always wanted a mixed use apartment building, so I'm going to build it myself because I just haven't been able to find one. So that's what I will be able to use my license in Michigan. I would say that's probably going to be in the next three to five years, but to be honest, I'm just making sure that my investment strategy is bulletproof. So I was literally doing inventory the other day and I have about 36 TVs, 12 king size beds, because all of my Airbnb. Right, right. 26 queen size beds. And I'm thinking like, well, what if short term rentals slow down? What if we go into a recession? What if Airbnb stops operating in Detroit or what if our, you know, our leaders say it's not allowed anymore? So what to do? So I'm actually continuing my journey into group homes, you know, and I know my, my girl is on the show. Lynette, I believe her name is. Yeah, she's been on here before talking about that, but that's just the natural pivots. So I've partnered with someone which is my first time ever, and we're going to turn one of my rentals into my first group home. And everything looks good. She has about 15, so she's experienced, she's doing it. And we're going to just split the revenue 50 50. But even with that, it's slated to make 35,000amonth and I'll be profiting about 7,000amonth. So on a regular rental that I would have charged 1800 so I feel like I'm just going to learn everything about it, document everything. We'll get the one group home up and running. But that's just like my backup plan just in case the short term rental thing doesn't work. And I don't want to be stuck with all this inventory. But other than that, just continue to optimize as I do tenant turnovers. Hey, can I add another bedroom? Can I add an addition? Can I add an apartment to what I already have? But that's literally the goal.
A
I love it. Well, good for you. I would love to have you back on soon to hear how it's evolving because I'm sure although it's a great plan, it sounds like you're always optimizing and finding, finding new ways to improve your portfolio and your lifestyle. And so thank you for sharing this update with us. We're gonna have to catch up with you again in another year or so.
B
Absolutely. I cannot wait. But as always, I see you all the time. I come to BiggerPockets BPCON every year, so for sure you can catch up with me there. I'll probably have 10 more doors by then. I don't know, that would be pretty.
A
Impressive because that's like a month from now. But there are still tickets if anyone wants to grab one. You can go to bigger podcast pockets.com Vegas. You can see Ashley, me and a ton of other great guests from the Bigger Pockets universe in Vegas this year at bpcon. Ashley, thanks so much for being here.
B
You're more than welcome. I appreciate it. It's always an honor to be featured on Bigger Pockets. I love it.
A
Absolutely. And thank you all so much for listening to this episode of the show. We'll see you next time. If you own a short term rental, here's something worth knowing. Not all landlord policies are built for your type of property. And with holiday bookings, chilly weather and higher guest turnover, having the right cover is more important than ever. Steadily offers insurance designed specifically for short term rentals, covering property damage, liability, lost rental income, and even unexpected issues like bed bugs. Steadily works exclusively with real estate investors so they understand the details that make short term rentals unique and they build coverage to match it. A quick review of your rates and coverage every year can help you protect your property and your cash flow. Get a quote in minutes@biggerpockets.com landlordinsurance steadily rental property Insurance for the Modern Investor hey everyone, my favorite event of the year is almost here, the Bigger Pockets Conference. And I'm here with some exciting news that we just added two new sessions that you do not want to miss. First, we have Doug Bryan, super bowl champion turned real estate strategist who's going to share his playbook that he used after 2008 to scale to 17,000 single family units. And we have Andy Gill, full time investor and tech pro who's going to share the exact AI prompts he uses to save our on contracts, deal analysis and operations. I've said it before, but it's worth repeating. The next wave of opportunity in real estate is already forming and I believe that the investors who get ahead won't be the luckiest. They're going to be the ones who are the most prepared. That's why I want to see you at bpcon with over 40 sessions packed with real tactics for today's market. You'll leave ready to act. But the real magic, it happens in the hallways. Connecting with other investors, swapping ideas and building relationships that last long after. Vegas October 5th is right around the corner. So if you've been on the fence, now is the time to get your ticket. You can grab it@biggerpockets.com Vegas that's biggerpockets.com Vegas.
Podcast: BiggerPockets Real Estate Podcast
Host: Dave Meyer
Guest: Ashley Hamilton
Date: September 22, 2025
This episode features Ashley Hamilton—a Detroit-based investor who went from earning $20,000 a year as a waitress to generating over $50,000 per month in passive real estate cash flow. Host Dave Meyer revisits Ashley’s journey for her third appearance, highlighting her portfolio growth from 10 to 45 properties, her focus on maximizing cash flow per property, creative strategies for scaling, and the personal transformation that real estate enabled in her life. The episode provides inspiration, practical investing tactics, and personal anecdotes demonstrating the broader impact of financial freedom.
Background:
First Property:
Early Cash Flow & Scaling:
Portfolio Growth:
Free & Clear vs. Leveraged:
Advice on Reinvestment and Mindset:
Short-Term Rentals:
Section 8 Rentals:
Creative Value-Adds:
Generational Wealth Achieved:
Lifestyle Transformation:
Holistic Approach to Wealth:
Perspective on Growth & Risk:
On Starting with Little:
On Mindset:
On Cash Flow Focus:
On Health & Wealth:
For more details or to connect, visit: biggerpockets.com.