You Don’t Need Dozens of Rentals to Reach Financial Freedom (He Tried It)
BiggerPockets Real Estate Podcast
Dr. John Crutchfield shares his journey from a school teacher to scaling a real estate portfolio of over 600 units across multiple states through aggressive acquisition and creative financing like owner financing and low-ball
Key takeaways
- John Crutchfield started with zero capital by texting hundreds of FSBOs on Zillow to secure an owner-financed deal for $80,000 that he renovated and rented for $1,200/month.
- He scaled to over 600 units by targeting distressed MLS listings, offering up to 40% below list price, and leveraging sweat equity with his family.
Main topics
- Creative financing & owner financing strategies
- MLS low-ball offer tactics & agent partnerships
Notable quotes
"It is a totally different game to sell real estate."
Conclusion
The episode delivers a crucial reality check for aspiring landlords, demons
Transcript preview
Speaker 3 (0:00) 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 ballooned. 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. Speaker 3 (1:08) 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. Speaker 2 (1:26) Man, too cool, too cool. How you doing, Henry Washington, the Henry Washington? Why Speaker 3 (1:31) 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. Speaker 2 (1:37) 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, you know, Florida State was right down the street. Fast forward a little bit, you know, got my first job as a teacher because, you know, 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 know, you do get paid a little bit more, but you have to be there all the time. So somebody then said, hey, you like to talk and you seem kind of smart. Maybe you want to be a college professor. Like that's the next level, right? All of these, by the way, you got to go back to school, Speaker 3 (2:25) pay Speaker 2 (2:26) 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 kind of got these increased roles, I ended up seeing lifestyle creep happen, right? So more money coming in the personal account meant, okay, better furniture or a bigger house, more spending, right? Because, hey, you got to have a better car because you're making more money, right? 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 Speaker 3 (3:08) and Speaker 2 (3:09) stumbled on like real estate investing. There was this podcast at the time called The Bigger Pockets Podcast. So it's funny. Never heard of it. 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. How Speaker 3 (3:29) old were you at the time when you found this real estate bug? Speaker 2 (3:33) Oh, probably 26, 25, 26. How long Speaker 3 (3:37) did it take you to go from that learning to doing Speaker 2 (3:40) and what were those steps? 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 a conversation, says, you should kind of like 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, like, 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. Speaker 3 (4:13) Yeah. Speaker 2 (4:14) 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 for sale by owners because I had a big problem. I didn't have any money. So I remember my strategy, like very concrete. It actually still works in 2026. It's a lot harder, but it still works. To go on Zillow, filter for for sale by owners. Speaker 2 (4:51) 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. Speaker 3 (5:08) 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. Speaker 2 (5:40) Absolutely. Speaker 3 (5:41) 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, 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? Speaker 2 (5:54) 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. So that's a screaming deal. Look, I owned that house for maybe 10 years before we sold it. And we sold it recently for like $220,000. Sounds Speaker 3 (6:36) like a deal to me, buddy. Speaker 2 (6:38) Yeah. And I ended up having an investor relationship, kind of a guy that... You know, we ended up doing more business together because of this. So that first deal went pretty well. Speaker 3 (6:49) This absolutely can still work. Almost all of my owner finance deals have been from landlords. because landlords understand the value of cashflow. 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 cashflow. And the way to do that is owner finance, because then you get paid every month, but you don't have to deal with tenants and toilets. So if you wanna 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. Speaker 3 (7:51) 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 want to finance you a house. And lo and behold, somebody says, yes, you end up buying a screaming