DE 27: The Advantages Of Working With Community Banks with Douglas Skipworth

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Douglas Skipworth has had an entrepreneurial heart from a young age. He began his journey in community banking and worked on earning his CPA and CFA certifications. Since then, he has been in the residential real estate industry for about 20 years and is passionate about partnering with others to develop thriving real estate businesses. He currently co-owns CrestCore Realty, which manages 2,500 properties in Memphis, TN. Along with his partner, they have built several real estate companies in brokerage, management, lending, and construction. 

In this episode, he discusses his life and business, the advantages of community banks, ideal criteria for investing in a new deal, the importance of connecting with others and shares helpful advice on education for today’s world. Listen in as he shows us hows real estate and adding value to others tie it all together. 

Episode Highlights:

  • How Much It Helps Your Business If You Connect With More People
  • Effects of Borrowing Too Much Money For Education
  • How Local Banks Help In Real Estate Investing
  • Importance Of Establishing A Relationship With Local Community Banks
  • Douglas’ Interest In Helping Certain Types Of People Via His Businesses

Connect with Douglas:



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Intro: Hey guys, this is Eden your co-host. Welcome to the show where we talk about all aspects of commercial real estate investing. Today, Don is interviewing Douglas Skipworth. Doug has been investing in real estate in the past 20 years. And today he’ll cover a lot of subjects including community banks, relationships in real estate and some philosophical issues like college and financial freedom through self-educating yourself with the tools that are available to us nowadays. I want to mention, again, our new website that’s forming a decent shape you can visit us at Also, remember you can always reach out to us I answer all emails personally: So, let’s get started guys.

Lady: Welcome to the commercial real estate investing podcast with Don and Eden where we cover all aspects of real estate investing with special attention to off-market strategies.

Don: All right. Hey, Douglas. Welcome to the show.

Douglas: Hey, Don. Great to be here.

Don: Yes, I think you deserve it because you’ve been doing real estate since 2001. Right?

Douglas: That’s correct. My partner started in 2001. And I started in real estate in 2002. Between the two of us, we’re going on 20 years.

Don: Wow. So, you guys have been through a lot, right? So, you started, the market was going up, then there was a bubble, and then everything changed. And then you guys probably had to make some adjustments and change business models. Now, when the markets have been going up for a few good years.

Douglas: Yeah, it’s so funny, because I don’t know when you always talk about the good old days. I don’t know if the good old days were when things were running up, or the good old days, because we were, you know, we were buying and refinancing and things were great or when things kind of went bust, because that was a huge opportunity for us personally to add to our portfolio as other investors busted in community banks had deals to give away and then rates have been so low for the past 10 years that that’s been a good time. So, if you kind of look back at the past 20 years it has been the good old days.

Don: Yeah, I don’t know who said it. I’m pretty sure it’s Warren Buffett. “When there’s blood on the street, buy real estate.”

Douglas: So true.

Don: Yeah. So, tell us about the early stages of your career. How did you get started? What did you do? How did you even hear about real estate? And what were your goals at the time?

Douglas: Great question. After college, I knew I wanted to start a business. So I kind of jumped into commercial banking and accounting, got my CPA and my CFA certifications to learn all I could about business and then I was working in New York City at the time and I had an opportunity to come to Memphis to work with an owner-operator of a real estate business when he was ginning up a tech company. It was kind of like a proprietary Zillow back in the early 2000s. It was a great chance for me to get on the owner-operator side of the business because I kind of knew from my first few years I wanted to be a business owner. So, I just kind of jumped in real estate tech and was learning a lot about real estate and I moved into a neighborhood and bumped into a guy who was a jogger. So, he and I started jogging together. He was in manufacturing, managing plants across the country mechanical engineer by training and he had in high school, a mentor who owned real estate and so he was building wealth through real estate while working his full-time corporate job. And I was working in real estate on a data in business side working with realtors and appraisers on the residential side.

So, we had a lot of commonalities, shared some interest, but he kind of told me about what he was doing with his investing portfolio of properties, both multifamily and single-family, I got interested. So, I started doing the same thing on my own. And we would jog together and share war stories and share best practices and really developed a friendship and almost a partnership. So, we decided we wanted to try and do a deal together that neither of us had done. So, to kind of share the risk. We ended up doing a tax sale because we had never bought a tax sale, either of us. And so, we just kind of shared the risk on that and it went well. Then we shared the risk on another one and another one and then we bought a little portfolio together and then we bought a few more together then we started doing some third party management together and fast forward to today we’ve got several hundred units together, we manage several thousand units together, we’ve got a brokerage and property management and maintenance company would do some hard money lending. So, we’ve enjoyed our friendship and business relationship.

Don: That’s truly amazing. I mean, I think, you know, going on a jog, and then meeting your future business partner that you’re going to do so many things with, it’s just outstanding. And that’s why people always say that when you are trying to get into real estate, then you should always say that this is what you’re doing to people. Because people are going to tell you something back and they’re going to tell you, hey, you should talk to this guy or I’ve heard about somebody who does that does this and then you get ideas. So, you always gotta talk to people. And that’s a great example of how talking to people, getting to know them, listening to them, changes your life in a good way.

Douglas: That’s a great point. Especially I was laughing about This was somebody the other day, because when I was working in banking when I was working in accounting when I was working in real estate technology, I would tell people that and nobody seemed interested or knew what to talk about. But as soon as I started investing in residential and small multifamily properties, and I would mention that everybody had either thought of it or had a friend or a family member who had been an investor at one time, or were thinking about doing it themselves or just buying a house. So, to your point, it just opens up a wealth of conversations and connections, that being a real estate investor and talking about it highly encourage people to do that.

Don: Definitely. Now, there’s another thing that I want to talk to you about because I just had this conversation with my friend and you just mentioned it that you went to college back in ’01 he said, right?

Douglas: I wish and I graduated in ’96. So, I’m a little older than that.

Don: Yeah, so a little bit older. So, this is exactly the time where you’re growing up, I believe. I don’t know how old you are. If you want to share it.

Douglas: I’ll be 46 in two weeks.

Don: 46. Happy birthday! Here’s my question. So, you are growing up at the times where your parents must have told you for the people that were close to you to go to college, right? Get a degree if you want to be successful in life, right? Now, my generation, I’m 30 years old, and I never went to college. So…

Douglas: Awesome. 

Don: I’ve been investing in real estate since I’m 23 years old. My background is kind of different because I wasn’t growing up in an environment that tells me that I have to go to college because we had the internet so we could hear other people talking. And so, there is the age of information where you could get a book for 10 bucks so you can listen to a podcast for free, right and get all the education you need. So, my question to you, would you recommend going to college in modern times or just jumping right in and just getting an education from a different source?

Douglas: If you’re entrepreneurial enough, and you have a plan and you have a determination, then yeah, you can do it on your own. There is a lifelong learning component that podcasts, books, resources now are at our fingertips as well. Well, it’s just meeting people’s mentors and connections. So clearly have learned more since I’ve been at a school then I learned in school. But for the right person, so for example, I got a master’s in accounting. When I was out of school, I worked full time went to school at night, and I got scholarships and the company paid a little bit. So, to get that degree to get that knowledge and earned that credential at a private university cost me $2,000 of my hard-earned money. All the rest of that money came from somewhere else, which was, which was a good lesson that I learned how to do real estate as well. You don’t have to go out and spend all your hard-earned money and borrow. There’re ways if you can get creative, you use other people’s money. So, what I wouldn’t suggest for 99.9% of the people is to go borrow $70,000 a year to get an education, an undergraduate…

Don: Exactly what I see. I mean, I see the age doing that. And I’m thinking you guys are taking debt for so long and you’re also investing time. So, you’re taking debt and investing time and I don’t like doing one of them. I don’t like investing my time for a long term period when I don’t know if it’s going to bear any fruits. And when you invest your time and your money, it kind of sets you back so much.

Douglas: It’s applicable in this because education is so important, whether you’re learning through podcasts or books. Yeah, one of my mentors, he owns 5200 unit multi-family, mostly low income that they do a phenomenal job across the Southeast. And he told me many years ago, “Never borrow unless you’re borrowing against an income-producing asset.” That’s where I was like, man, I can’t borrow to go to school’ I can’t borrow for a car. I got to borrow against an income-producing asset, whether it’s a business or a real estate piece of property. So that’s a valuable lesson that a super successful multifamily investor gave me 20 years ago and I’ve never forgotten. So, very much on point to not borrow for that education, not borrow significantly for that education. Because it’s going to put you back.

Don: Yeah, I agree. And I think what I’m going to do, you just gave me an idea. I’m just going to record an episode later on that will talk about that subject specifically. I want to get back to borrowing money because I know you have a way of borrowing money. You’re borrowing money from community banks.

Douglas: Yes.

Don: So, tell us a little bit about that. I know it’s different now, you can make things happen when you work with the community bank.

Douglas: Yeah, so we’ve worked with community banks since 2001. Part of the reason we like working with, some of the benefits is their local that you can go to church with them, to school, kids playing on sports teams, living in the same neighborhood. So, there’s more of a story relationship aspect, and then there’s also the local component to it. So, they’re going to work with you and get behind you and understand that and then they’re going to be a lot more interested in that relationship and kind of support you. They can’t do as big a deal. They got lending limits, but they also have access to other local investors and kind of keep you in mind. So, for us, it’s just been a great relationship. The Real coup for us was when the bad times hit for other investors and those banks had property, they were taken back. And they were looking to get it off of their balance sheet because they did not want to own real estate. And they didn’t give it away. But there they created a win-win. It was kind of a “your price, my terms” situation, whereas they would say, “Hey, we want it at this price. We need to get it off at this price.” And we say, “Okay, these are our terms.” And if they said, “Hey, here, the terms we need,” then we’d say, “Well, this is the price that we need.” And we picked up hundreds of units during that ’08 to 2014 probably working with community banks and borrowing and all the money from them on those deals.

Don: Yeah, that’s amazing. I know, multifamily was doing pretty well in ’08 relatively. So, it’s very smart to buy them at that time. I wish I was investing in real estate at that time, life would have been different. So, I want to ask you about your relationship with this bank. So, when you establish your relationship with the community bank, how do you do that? So how do you choose the bank? Is it more personal? Are they looking into your financials in a more personal way, not as strict of a guideline is what I’m asking.

Douglas: There’s no doubt to have guidelines. But you’re right. It is a relationship. If someone were to look for a relationship with a community bank in their location, start with friends, family, mentors, anybody who knows somebody who was either sympathetic to you personally some way or to the real estate property investing or learning on real estate. So that’s how we’ve established those relationships. There are plenty of local community banks that don’t want to have anything to do with what we’re doing. They don’t like lending on real estate, they’ve got too much real estate, whatever. But some lots are in it’s through those relationships where you develop a business strategic partnership with the banks.

Don: Would you say that these loans are typically more expensive than what you would get with a regular loan?

Douglas: So, for us, we kind of looked at loans and there’s the traditional mortgage market where you can price things pretty cheap, but you got to have good credit. And then there’s the community bank. And there are private loans. There’s hard money lending. So, there are several different routes. Community bank financing is pretty cheap. It’s got some strings attached, because they want you to jump through some hoops more so than a private lender would, more so than a hard money lender would. It will be things they’re going to review past couple years of tax returns, they might run a credit check on you, they’re going to ask for you sign a personal guarantee. So, they’re going to be some things that some other lenders aren’t going to have. But again, they’re going to look out for you and they’re going to keep you in mind when they’re talking to other investors. Other investors want to get out of deals, they’re going to say, “Hey, we’re going to talk to Don and Eden they’re doing this” or “sell your properties to Don Eden, and we’ll finance it” where they can just assume your mortgage or assume your loan. So, we’ve done that with banks and through relationships, which is a lot harder to do with national lenders as you know.

Don: They lend for properties that are in their area, or they could lend for properties anywhere in the US?

Douglas: Primarily they’ll lend to either properties that are in their area or borrowers that are domiciled or headquartered or located in the area.

Don: Yeah.

Douglas: So, they will do deals outside of the state if it’s somebody they know locally.

Don: Yeah, that’s very interesting. Yeah

Douglas: It’s great. And it becomes a network and they become part of your network, and they become one of your strategic partners. And you can develop relationships with multiple community banks and work with all of them. And it’s a great mutually beneficial relationship.

Don: Terrific. Yeah, I think that’s critical information for somebody who’s listening to that show. And they want to get a loan for a property that they want to buy and they don’t know who to talk to. I guess that’s just an option that you got to consider. Go talk to your community bank, establish a relationship and get to know the people there because real estate is a long play. You do something where you plant seeds right now, and you wait for the seeds to sprout in the future. So, I guess that’s one seed that you got to plant right? The community. Got to go and talk to people when you want to do deals.

Douglas: It’s been everything from helping you find new deals to financing deals to providing opportunities for other lines of business. So, they can help you finance because you built up a track record with them and they understand who you are and how you operate. So, they become a champion for you within their organization and the community. I couldn’t recommend it highly enough. It’s been one of the keys to the foundation of our real estate business. You’ve got deals, financing, and management when it comes to investing and finding deals, financing or paying for those deals and then manage them after the fact. So that financing piece is huge, whether it’s your cash or somebody else’s cash. Most real estate investors use somebody else’s cash. So, a community bank is a great option.

Don: Awesome. You manage over 3000 units and you also invest in real estate. So, you bought together with your partner over 800 units and you haven’t had any money partners or equity partner so you’ve done this by yourself, complete with both of your hands. And that’s amazing. I gotta say, I host a lot of people here on the show. Most of the people that try to syndicate, try to get to raise funds, and then buy their deals. You’ve been investing for better of two decades right now, and you’ve been doing that on your own. But I want to ask you if you’ve been investing in real estate and creating your wealth, why do you still want to do property management? Is it because of your investments? Or is it just because that’s your core business?

Douglas: Probably all of the above. And we feel like part of what we’re here to do is to serve people profitably, you know, so we’re in business to serve. Because we have our rental properties, we have to do property management, and we’d like to have our rental properties for the duration. So, we need to do property management and then managing properties for others is a skill that we have developed so we can get paid for it, we can get better at it and we can use it to serve others. So, it’s kind of a mutually virtuous cycle of things going around where we get better, it helps us manage our properties better but helps us serve our clients better. So…

Don: Win-win-win-win-win. That’s many things in real estate.

Douglas: Absolutely all the way around. And that’s why we’ve expanded to Jackson, Tennessee, and Dyersburg, Tennessee and you know, hopes to expand into Eastern Arkansas, Central Arkansas, North Mississippi, Central Mississippi over time because it benefits all of us to do that.

Don: It’s what I like about real estate that you could find so many things to do in real estate that creates a win-win-win-win in different types of businesses. It’s not the way that it is in real estate. You can create a business that creates wealth for you, that helps you with taxes that appreciate that cash flows, and that is being managed by you as another business. It’s just amazing. So, we’ve been doing all that. It leads me to ask you, what would be the criteria for buying a new deal?

Douglas: We’ve kind of bootstrapped it on our own. So, we’re limited because we don’t have equity partners and we don’t syndicate. We usually have to have the financing in place. So that’s assuming a loan, or some type of owner financing, or working directly with a bank that can provide the purchase money. We’re super limited on what we do, which just leads to more deals for everybody else clients and that’s great, but we’re super selective at this at least we have been for the past 20 years we look forward to someday where we can just go out bad things all cash and not worry about it. But so, we’re selective looking for different things, whether it’s a single-family home, small multifamily or small commercial building. The recent thing we bought a property management company and bought the building. So, we’re now an owner occupant of our office in that building. So that’s a great win-win.

Don: You buy the tenant and the building and you’re the owner of both.

Douglas: Exactly. So that’s the most recent that was a month and a half ago. So that’s been great.

Don: You’ve been working with your partner surely but slowly, right? You’ve been managing properties, investing, buying them one by one with your money, creating long-term wealth, going to stay in your family forever. What would be the next step?

Douglas: One thing we’ve been very fortunate on it’s just building and surround yourself with some great people and building a good team. We’ve got folks who help run the businesses and operate the day today. And that’s been awesome for us. So, continuing to develop those folks and grow opportunities for them as well as for ourselves. So, with the businesses we have now, which are really real estate services, brokerage, property management, maintenance, like said financing, then we have some business services, we provide some virtual assistants and some business back end support to our businesses and a few others. Just growing those real estate service lines and business service lines in this geographic area is our next focus personally for the next five years.

Don: Awesome. So, what kind of areas are you guys going to focus on it in case anybody wants a property manager or wants to consult with you on a few things that have to do with real estate?

Douglas: Yeah, so we help folks like ourselves, people who are wanting to build wealth, people who are wanting financial freedom, people who are looking to create an income or buy something to pay it down over time in resident real estate, small commercial real estate, multifamily real estate in kind of this MidSouth Mississippi, Tennessee Arkansas area around Memphis, Little Rock, Jackson, Mississippi. So, anything related to that brokerage, property management, maintenance, construction, lending, helping people fix and flip, helping people bridge loans into a long term loan. And then we provide virtual assistant services for folks who are doing real estate services, whether it’s just somebody operating on their own or a brokerage or property management company, we’re happy to help that because we’ve got a lot of experience. We got about 120 virtual assistants right now in the Philippines that work for 18 companies. Again, we feel our calling is to help people succeed through business and real estate. That’s what we’re trying to do and we’re trying to help other people do it too.

Don: Try and make an impact when you’re already wealthy. That’s the next thing is to try to make an impact and help other people and that’s truly a remarkable goal. So, what would be the best way to contact you Doug in case anybody wants to get in touch?

Douglas: I love to talk to anybody. Easy to send me an email at or find me on LinkedIn or find me on BiggerPockets. Those are probably the three best ways to get in touch.

Don: Right. So, I want to thank you very much for being on the show today, Doug.

Douglas: Love that, Don. Thanks for having me.

Lady: Thanks for listening to the Real Estate Investing podcast with Don and Eden. Stay tuned for more episodes. Till next time!

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