You Don’t Need Dozens of Rentals to Reach Financial Freedom (He Tried It)

Henry Washington:
You don’t need dozens of rentals to reach financial freedom. And if you ask today’s guest, less is usually more. For over a decade, John Crutchfield was in full acquisition mode. Despite starting with very little money, he scaled to over 600 units across multiple states and tens of millions of dollars worth of real estate. He even quit his job so he could focus on his portfolio full time, but then the market changed. Interest rates spiked, debt became more expensive, and John’s expenses bloomed. Suddenly, owning more properties wasn’t making him any wealthier, so he started selling. And in the process, John learned a crucial lesson about building wealth. Sometimes having less can actually give you more, more cash flow, more flexibility, more peace of mind. In today’s episode, John shares the highs and the lows of his real estate investing journey, how he turned a smaller portfolio into a more profitable business, and why door count matters far less than the freedom each property provides.
What’s going on, everybody? I’m Henry Washington, co-host of the BiggerPockets Podcast. And today we’re bringing you an investor story with Dr. John Crutchfield who invests in Tupelo, Mississippi. So let’s bring him on. All right, Dr. John Crutchfield, welcome to the BiggerPockets Podcast, my friend.

John Crutchfield:
Man, too cool, too cool. How you doing? Henry Washington, the Henry Washington.

Henry Washington:
Why don’t you give us some background? Start a little bit before real estate and then kind of talk us up to where you are now.

John Crutchfield:
I’m John Crutchfield. Grew up in Tallahassee, Florida. I’m a Florida boy. Time came to go to college. It was like, okay, where are you going? Well, I don’t want to go too far. So Florida State was right down the street. Fast forward a little bit, got my first job as a teacher because teachers get summers off, they get all the holidays. Somebody said, “Well, if you go back to school, you’re such a good teacher. I bet you could be a good principal.” And I was like, “Yeah, you know what? That’s right.” So I went back and got a master’s degree, became a principal, realized that as a principal, you do get paid a little bit more, but you have to be there all the time. So somebody then said, “Hey, you’d like to talk and you seem kind of smart. Maybe you want to be a college professor.
That’s the next level. All of these, by the way, you got to go back to school, pay more money so that you can get a better job.” And so I just kind of followed that track, ended up as a professor at Ole Miss, that probably was my dream job, got to help people who wanted to become teachers become teachers. So very fulfilling work. But every time I got these increased roles, I ended up seeing lifestyle creep happen. So more money coming in the personal account meant, okay, better furniture or a bigger house, more spending because hey, you got to have a better car because you’re making more money. That’s the thought. And so ended up at the end of the month, no matter what job I had, not having enough money or having to wait till the next month. So then I started Googling stuff like passive income and stumbled on real estate investing.
There was this podcast at the time called the BiggerPockets Podcast. So it’s funny. Never heard

Henry Washington:
Of it.

John Crutchfield:
Yeah. And I stumbled on their forums, getting tons of quality answers from the community, but just started kind of feeding that bug of getting financial education.

Henry Washington:
How old were you at the time when you found this real estate bug?

John Crutchfield:
Oh, probably 26. 25, 26.

Henry Washington:
How long did it take you to go from that learning to doing and what were those steps?

John Crutchfield:
I ended up meeting a guy at church who had about 30 properties, and this was his retirement plan. And he, as we’re having the conversation says, “You should sit with me so I can show you what I’m doing.” And that mentorship became very valuable to me because we struck up a relationship, started having multiple conversations. He sat down with me and he told me, “Just look at your life in your W2 world. If you can run a school, you can run a business.” That was kind of my moment because before he said that, I had never in my life considered actually owning a business. That’s how ingrained it was for me that you go to school, you get good grades, you go to college, you get a good job. I was that guy. So what I ended up doing is going online like some people do and looking for sale by owners because I had a big problem.
I didn’t have any money. So I remember my strategy, very concrete, it actually still works in 2026. It’s a lot harder, but it still works. To go on Zillow, filter for sale by owners, and you get their phone number right there. And I will text them, “I’m interested in buying your house, but I don’t have any money. Will you owner finance it to me?” That was the text that I sent hundreds of times and one guy said yes. He said, “Actually, I will.”

Henry Washington:
It does still work. You can actually do that. But most people won’t commit to sending the amount of text messages that you would need to send in order for somebody to get a yes. Where people screw up, it’s not that you can’t get into real estate with limited funds, it’s that most people aren’t willing to put in the level of effort it’s going to take to find that deal and to get that deal closed when you don’t have money as a resource. You’re going to have to spend way more time and put a lot more effort in. You got to be more creative.

John Crutchfield:
Absolutely.

Henry Washington:
Well, I know it was a while ago, but the principles remain the same. Would you mind sharing with us kind of what that ended up looking like, what that deal structure was? What’d you pay for the house? How’d you structure the financing? What’d you give him? What’d you not give him?

John Crutchfield:
I bought the house for $80,000. It was a three bedroom, two bath in the market that I’m in, Tupelo, Mississippi. The monthly payment was $528 a month. And then I was responsible for the taxes and insurance. The house did need about $20,000 in work. So he had just had a tenant move and that’s why he was interested in this because he didn’t want to do the renovations. Ended up spending that 20,000, a lot of it was sweat equity, but getting the house presentable where we could rent the house out and ended up renting the house out for $1,200 a month.

Henry Washington:
So that’s a screaming deal.

John Crutchfield:
Look, I owned that house for maybe 10 years before we sold it and we sold it recently for like $220,000.

Henry Washington:
Sounds like a deal to me, buddy.

John Crutchfield:
Yeah. And I ended up having an investor relationship, kind of a guy that we ended up doing more business together because of this. So that first deal went pretty well.

Henry Washington:
This absolutely can still work. Almost all of my owner finance deals have been from landlords because landlords understand the value of cash flow. That’s why they were landlords in the first place. And a lot of people would love to get out of the business of being a landlord, but still maintain cash flow. And the way to do that is owner finance because then you get paid every month, but you’re doing got to deal with tenants and toilets. So if you want to try this, I would say try it, except just do it a little different now. Help yourself pull a list of people who own property free and clear, absentee owners and landlords. Call them all or text them all and ask them. And I bet you won’t have to send as many thousands, but it’ll still be a lot and you’ll get a lot of rejection, but this can absolutely still work.
So I’m very curious how that deal sparked your growth and how long it took you to scale, but I want to ask you those questions right after the break. All right. Welcome back to the BiggerPockets Podcast. I am here with investor Dr. John Crutchfield, who just told us the story of his first deal. And it’s so interesting that our stories are so similar in how we got started in our upbringings even into leading into that first deal. So you did a first deal, pure hustle, sent hundreds of text messages asking somebody if they’d owner finance you a house. And lo and behold, somebody says yes, you end up buying a screaming deal. How did that spark the rest of your real estate investment journey?

John Crutchfield:
When I had the mentor that I mentioned come over to look at the house after we were done, he was like, “I think you need to get this appraised.” That was the eureka moment. When I got the appraisal and I had $100,000 on this property, but it was worth 160, and at the time I was a professor at a college making $60,000 in a whole year. I was like, “Wait a minute, this is possible to do over and over and over again?” And he was like, “Yes.” And so that is how the first deal really kind of sparks the push into, “Well, if I could do this five times a year, I’d be making five times as much as I make on a job. And this is a no-brainer.” At the time, I never thought about quitting my job. I just said, “I could do my job and do this on the side.” So ended up doing my next deal.
Similar type situation. I would say you asked me how long. It was probably a year or two. There was some space, but ended up buying a property, again, very limited funds, using sweat equity. I have pictures with my wife and kids helping me paint and fix up countertops, but ended up doing a similar thing. $15,000 purchase. This is a Mississippi property.

Henry Washington:
$15,000 for the whole house or the down payment?

John Crutchfield:
For the whole house. There was an evolution that happened here. Once I saw that appraisal and the whole value add situation, my mind switched from, “Well, I need to get the properties for as low as possible.” My strategy improved, and this is a strategy I used probably for my first 30 units. You have all these people on the MLS that are trying to sell their property, and some of those properties are sitting there for months and months and months. So I found a realtor who would do what I asked, because some of them wouldn’t. I just want to offer $15,000 on everything on the market. And that’s what I started doing, just offering as low as possible on everything on the market. Some of them wouldn’t respond. Some of them would say, “Heck no,” all that stuff. But then somebody would counter a lot lower than their asking price.
Or in this case, the guy just said, “Have you even looked at the house? Yes, I’ll take 15K.”

Henry Washington:
That doesn’t sound like a good answer. Oh

John Crutchfield:
My goodness. If I asked a third grader to describe what they think a $15,000 house looks like, that’s what this house looked like.

Henry Washington:
The house needed a whole new house?

John Crutchfield:
It needed everything. It needed everything. Everything. Holes everywhere, stuff everywhere, vacant for a long time. But the numbers made sense. I ended up buying that house for 15K. My wife and I spent about 35. Again, a lot of that sweat equity in there, went to the bank and they said it was worth 100K. So this whole concept of adding value and making something worth more because you did the work, it really provoked an addiction. And so that’s kind of what I did. I started doing as many of these as I could.

Henry Washington:
I actually teach people how to offer on the MLS in a very similar fashion. You want to find a deal on the MLS? Do these steps. Define your buy box. Your buy box is just what you want to buy and where you want to buy it, right? Give that buy box to an agent who’s willing to submit offers for you. John said not everybody was willing to do this for him. That’s still true to this day. You got to find an agent who’s going to be willing to do this dirty work. And so I pull every house on the MLS that is in my buy box and has been listed for 90 days or more. Average days on market here is about 60 days. So I do 30 days beyond average days on market. That’s my assumption that they may be motivated for a lower offer.
And then I just have my agent offer 40% off of the price it’s listed for. So we take the list price, we subtract 40%, that is our offer. And we don’t write up official offers for everyone. My agent has a canned text message that he sends to the other agent that basically paints me as the bad guy so he doesn’t have to damage his reputation for making lower offers. He says, “Hey, I’ve got an investor client. He’s only making offers based on the numbers. It’s not personal at all. I’m sorry the offer’s not what you’re hoping it is, but would you consider an offer of X?” And he sends that to every one of these listings. We are not looking for someone to say yes. Matter of fact, I don’t want somebody to say yes. Like your guy said yes, that ended up being a doozy.
If somebody takes that and says yes, I’m probably pretty skittish, but absolutely want people to counter because if you counter or if you say, “Hey, we’d consider it, great. Now we can have a conversation. I can go see the house. I can analyze it thoroughly and I can make an offer.” This is the exact same strategy you just talked about, maybe refined a little different for the times. You guys, this stuff still works if you’re willing to put in the hustle.

John Crutchfield:
That idea of making offers and starting conversations is something that I still have to remind myself of all the time. When I want to build my pipeline, it’s like how many conversations have I had? How many offers have I made?

Henry Washington:
People get so overwhelmed with the concept of how do I find a good deal? Simplify the process. That’s what John just did. If you simplify the process down, it becomes a lot easier. So what if instead of worrying about what kind of marketing you’re going to do or if you’re going to make MLS offers, what if you just said, “What if I talk to three to five people a day who can sell me a house?” Just get on the phone with three to five people a day who can sell you a house. If you make it a point to have a conversation with three to five people a day who could sell you a house, I bet you’d buy a house pretty quickly, 30, 60, 90 days if you do that consistently. So what does that mean? You can either call direct sellers and see if they’re willing to talk to you about selling a house, real estate agent.
You can call real estate agents and see if they have anything that would fit your buy box, or you can call a wholesaler. Those are three different types of people who can all help you buy a house. So talk to one of each a day. What if you just talk to a wholesaler, a seller and a real estate agent every day? That’s very easy to do. And if you did that consistently for 30 days, I bet you’d be pretty close to getting a deal.

John Crutchfield:
And also what you’re doing is you’re leveraging other people to help you reach your goal. So now it’s not just the deal you’re looking at that you might have started the conversation with, but it’s all the other deals that they may be aware of that they may present and say, “Hey, this is something you should consider.” So you’re exponentially growing your reach by having these conversations.

Henry Washington:
Would you mind sharing with us kind of how big your business got over the course of the next several years and what that timeframe looked like for you to get there?

John Crutchfield:
So I actually don’t know how many I had at the peak. I really don’t. I would go to these conferences and people would be like, “How many doors?” And I was using a CRM, so I know I remember 585. I remember that number being in the CRM. Problem was I was focused on acquisition and growing, so not all the units ever made it into the CRM. We were picking up deals in Iowa. I was picking up deals in Arkansas, picking up deals we started buying in Texas.

Henry Washington:
And you were keeping these. These weren’t like wholesale deals.

John Crutchfield:
Never sold a property till the market turned and I realized I should have been selling some sometimes. It probably ended up being 600 plus.

Henry Washington:
That’s a lot of real estate across multiple states. Were you building teams in all these states to help you operate all this real estate and were you buying it all creative? That’s a lot, man.

John Crutchfield:
Yeah. So out of state means you got to leverage other people. And so a lot of times we were partnering with property management in those areas because I didn’t have a team there. And then you’re absolutely correct. You probably are not going to buy 500 plus units with it just being one house at a time, one property at a time. And so somewhere in 2017, 2018, it kind of clicked for me that a lot of property owners, a lot of landlords had more than one property that they would want to sell at one time.
And so I remember buying a package of 50 doors. I remember buying a package of 30. I would go on the property tax records and I would look for LLCs or people that had multiple properties under their name and they would get a text or an email from me. And at that point, my goal was growth. So if they asked me what I wanted to buy, it was like, how much are you willing to sell? And so I started being that leader, that visionary that was thinking, how fast can I grow the door count? Since I’ve realized that that actually doesn’t matter at all. So what I loved doing was making an offer on a property, figuring out what my renovations were going to be, figuring out what that ARV was going to be and putting that in a spreadsheet, figuring out what the rent was going to be, what the expenses I thought would be, and putting that in a spreadsheet.
And so what I would do is every time I was acquiring, I would just add to my spreadsheet and it starts to add up really fast. I mean, when I say I got addicted to this, I got addicted to every 30 days updating my personal financial statement and seeing my net worth just going up like crazy or every single month seeing the deposits in the bank account keep going up. And so if you’re somebody who grew up like I did or who was a school teacher and you’re making $3,000 net after your pay, seeing $100,000 hit a bank account or $200,000 start to hit a bank account every single month, you’re just looking at that top number saying, “This is beautiful. I’m doing something right.” But when you as the owner are focused on just growing, you are kind of at the mercy of your property management, you’re at the mercy of your team.
And then most importantly, you’re at mercy of the expenses staying the same as what was in your proforma, and that will not stay the same.

Henry Washington:
Were you still working your day job when you were this big?

John Crutchfield:
I quit my day job once I realized the possibilities, right? In fact, I just became a horrible employee, right? They would ask me to do something extra or give me an extra assignment and I was like, “Do I want to do this instead of trying to be a good team player?” So I remember, and this was in the peak of good times, I remember doing a deal where I added $300,000 into my net worth on one deal. I remember my boss saying, “Hey, we need you to teach an extra class or something and we’re not going to pay you for it because we think you can fit it in your schedule.” And I was like, “I got to talk to my wife, but I think I’m done.” And I ended up quitting, but I went full-time into this business somewhere around 2019. And so that meant every day I was giving 100% of my effort to growing the business.
I’m an entrepreneur now. I’m a full-time business owner. I probably work too much, but I don’t clock in or clock out. So it feels like I’m doing what I like to do.

Henry Washington:
And that’s specifically what I’d like to talk to you about right after the break is what were some of the lessons you learned as a technically small business operating a large portfolio. So let’s jump into that after we come back. All right, we’re back on the BiggerPockets podcast. I’m talking with investor Dr. John Crutchfield, who took growing and scaling to a whole new level and did it during a market transition. You said you quit your job in around 2019. The market got real good between 2019 and 2022, and then it’s been not as great from 2022, 2023 until now. So I’m very curious about what lessons you learned while you were in that growth mode and operating mode and how that’s shaped where your business is today.

John Crutchfield:
I learned that more doors does not necessarily mean more success. Once you get into it, you realize, okay, I’m actually now managing employees, I’m managing contractors, I’m managing inventory and materials that I don’t want to just walk off. All of the little issues that you might have on one project, I want you to start multiplying those by hundreds of doors. You know the stories, right? Contractor walks off with this material or you got a water leak or some kind of plumbing issue or AC out, and this is going to create wear and tear on your properties, but also ultimately affect your bottom line, which is what matters, not door count, your bottom line, what’s left over at the end of the month. And so people ask me, well, what’s it like? Were you really making 50, $100,000 a month? Henry, I remember celebrating at one point I was paying off a house every single month.
In Mississippi, a good house was 60, 70K. I was paying down 50, 60, 70K a month in debt pay down and looking at that like, man, I got a house paid off and I’m doing that every single month. So beautiful. But then you’d have some seasons of the year where we were giving that back in CapEx because when their AC goes off, it has to be fixed. You can’t say, well, I’m just a little landlord and I only have a property or two and I need you to understand or you’re going to be in a newspaper. You got to get those units fixed and get those people back up so that they’re operating, they can have a safe, affordable place to live. A key principle here is that it’s like a living, breathing organism as you grow that has so many lessons that you can’t find in a book.

Henry Washington:
Yes.

John Crutchfield:
And that’s what I learned.

Henry Washington:
So how did that change your business? Did you start to sell property? Did you stay in growth mode? What changed and when did it start to change?

John Crutchfield:
So big change started in late 2022, 2023. A lot of us are aware that the Fed started increasing interest rates. And if you have $30 million borrowed and your interest rate average is 4%, that’s like free money. It’s beautiful. You’re making payments and you got money left over to do stuff. But when that same $30 million, and a lot of my loans were these local community bank loans that reset every five years, ask me how they time this, okay? When they reset and then your average interest rate goes to eight, that literally is a huge increase in your expenses and it changes your lifestyle. So if I had one property where the mortgage payment went from 12,000 to 21,000, that changes the salaries that I can pay off that property. It changes the salary I can pay myself. And then you multiply that across the whole portfolio and you’re really in a tight trying to figure out, okay, how am I going to adjust?
The first adjustment we made is like, okay, let’s double down on the strategy that was working for me. I grew the business by burrowing, buying and fixing up the property and renting it out and refinancing. So let’s go borrow some more money so that we can have cash to keep operating. That was the first thing I did. The problem is we weren’t borrowing that cheap money anymore. We were borrowing more expensive money. And it got volatile, Henry. It got kind of volatile for a little bit as those rates were going up. Some of the lenders started squeezing in some 10% rates in there. So we had the cash to operate today, but not the cash to operate in the future if we were depending on cashflow. And so realized looking at the spreadsheets that this was not going to work. Eventually we were going to run out of cash and we were going to run out of the ability to keep borrowing.
And so this is when I started saying, okay, we got to sell some stuff. I wish I had took some chips off the table sooner. I will tell you something, this is probably put this on a bumper sticker. It’s actually very easy to buy real estate. It is a totally different game to sell real estate.

Henry Washington:
That’s true.

John Crutchfield:
And it’s a new skill that we’re still having to learn because we’re still selling some properties. Fortunately, I met some awesome realtors who have been helping dispose some of the portfolio, and I’m also now a licensed realtor, so I’ve learned a little bit more about selling properties as well. I told you I quit my job, but I thought that I quit my job to live off the rental properties. That was a misunderstanding. And so when you start pulling your lifestyle off of the rental properties, that makes the things tighter as well. And so what I learned as we started selling properties is like, oh, I actually still need an active income from something to make sure that I’m not pulling money off of these very limited tight margin rental properties and cash flows. So that’s probably a whole nother thing. But if I could save one person, I’m like, “Hey, quitting your job is beautiful in this business once you’re ready, but it’s not always the right thing for everybody.”

Henry Washington:
The realization I had was I’m running a business, the business makes money, and then if I take all the money it makes out of the business every month, it’s hard for the business to grow. If I suck every ounce of profit out and I don’t reallocate some of that to improving the business, the business doesn’t grow. Any business that isn’t real estate, they don’t do that. They don’t suck all the profits out and then hope the business grows. There’s a plan for reallocating profits to continue to grow the business. Two, most investors realize, okay, if I’m going to quit my job, it’s not going to be the cash flow that gets me there. It’s a hard realization because most of us get sold into real estate investing on the concept of properties paying for life’s expenses. That was the thing that got me. Oh, you want to buy a new car, get a house.
The house produces cash flow, cashflow pays for the car. In practice, it doesn’t always work like that because maintenance is unpredictable because even if you are predicting the maintenance, if you haven’t owned the property that long, you haven’t saved up enough cash to cover said maintenance item that comes from somewhere out of your pocket, which means you have less to go pay for this new car or this thing you have in your lifestyle. And so you realize the same thing I realized and the same thing that a lot of investors listening to this are going to realize that if I want to quit my job and use real estate, I can’t just do it on cash flow. I have to find another active income stream within the real estate space to do that. And there’s nothing wrong with that. And so I tell people, yeah, I retired from corporate, but I didn’t retire from working.
I flip houses. That’s a job. It’s a construction business. That’s what I do. And on its surface, I flip houses. So I run a construction business that renovates properties that produces cash. I use that cash and I live off that cash so I don’t have to touch my cash flow. I can use that cash to also pay down the assets and then at some point I won’t have to flip houses anymore. And so for those of you that are listening, if you want to quit your job, you can get there, but think of it in two phases. Phase one is if I want to get out of my corporate gig, what job within the real estate space can I replace my corporate gig with? Phase two is to work yourself out of having to have that active income stream over the course of the next several years.
So my goal is to take the flip proceeds, pay off more rentals. More paid off rentals is unleveraged cash flow, unleveraged cash flow is substantially higher than leverage cash flow, and at some point I don’t have to flip houses anymore. So that’s the way that I think people need to think about leaving their job.

John Crutchfield:
And you don’t need hundreds of doors if you’re looking at it like paid off rental property. So the 500 number, totally unnecessary. What you just said there is like gold for anybody that’s like, okay, if I want to fast track my knowledge five, 10 years in the business, just listen to what Henry just said about active cash flow, paying off your eventual retirement income.

Henry Washington:
Let’s put some actual numbers to this, if you don’t mind. Where does your portfolio stand today and where are you trying to get it to?

John Crutchfield:
I mean, at the peak, we probably were close to 30 to 35 million in assets and today we’re down to about 10 million.

Henry Washington:
Wow. So you sold two thirds of your portfolio?

John Crutchfield:
Yes. And selling and selling. So what that means is we’ve had capital to be able to reinvest in other things, but also it means we’ve taken some chips off the table. Unfortunately, we are not selling at a time where you can get those max values. And so that means that in some cases I’ve had to be a motivated seller. We wanted to get out of certain debt. Just to be clear, if I’m at a 10% interest rate right now, that property is not making money, not in the market that I’m in. So being out of them in certain cases was better than holding onto them. I don’t actually have a target anymore for the size of the portfolio because what I realized is that I already have more than I’ll ever need if it’s paid off.
I’ll give you an example. A lot of my properties are five, 10 property packages. Well, if I sell six of them, I’ve got four free and clear. And that’s been happening over and over for the last three years. So I’m starting to fall in love with the ones that we own that don’t have any payment, whereas the ones that are kind of in these packages and still in debt, especially if they’re not cash flowing, they got to go. Of course, I have a proforma and I have a spreadsheet, but when you go to sell, you don’t know what’s going to sell first or what’s going to sell for what.

Henry Washington:
There

John Crutchfield:
You go. And you’re kind of adjusting the plan every 30 days as it goes.

Henry Washington:
This is the realest real estate talk I’ve had in a while. All right, John, you shared a lot with us and I’m sure there are people who would love to learn more about you and the choices you’ve made in your business. And so if somebody wants to reach out, how can they find you?

John Crutchfield:
You can find me all over social handle is @grabthemap, or you can just search my name on Facebook. I’d probably hang out there where the old folks are. That’s what my kids tell me is where the old folks are.

Henry Washington:
All right, John. And if you are listening to this episode and you are thinking, “Man, I’ve got a pretty cool story I’d like to share with the listeners of the BiggerPockets Podcast,” well, you may have a chance. Why don’t you head on over to biggerpockets.com/guest and fill out the form. You may find yourself right here in a conversation with myself or Dave sharing your story for the betterment of our community. Once again, thank you so much for listening to the BiggerPockets Podcast. We’ll see you on the next episode.