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In this episode of the Real Estate Pros podcast, host Michelle Kesil interviews Strickland Holloway, a seasoned developer, broker, and attorney from Georgia. Strickland shares his extensive experience in real estate, detailing his journey from practicing law to becoming a successful developer. He discusses innovative concepts in real estate development, such as fractional ownership and the challenges faced in financing and marketing properties. Strickland also offers valuable advice for aspiring developers, emphasizing the importance of making informed decisions and being adaptable in the face of challenges.

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    Investor Fuel Show Transcript:

    Strickland Holloway, Jr (00:00)
    I wound up buying 277 acres for about $76,000. I sold off part of it to my partner who’s a real estate partner that I had in the law practice.

    and he bought 70 something acres. That left me with 200. And I wound up selling 50 acres for enough money to pay off what I paid for the whole place. And I kept 150 and then divided up into lots and sold that off. So it was a good development right out the gate. I learned early on that I could make more money signing my name on a note than I could practicing law all year long.

    Michelle Kesil (02:10)
    Hey everybody, welcome to the Real Estate Pros podcast. I’m your host, Michelle Kesil Today I’m joined by someone I’m looking forward to chatting with, Strickland Holloway, who is a developer, broker, and attorney in Georgia. So, excited to have you here today, Strickland.

    Strickland Holloway, Jr (02:24)
    to be here. I really like your format and what the company is doing to share knowledge with other people. It’s always important to have someone give you some help along the way and I’m happy to share what little knowledge I have. I do have a little bit.

    Michelle Kesil (02:40)
    Awesome, excited for you to share. So first off, for those who are not familiar with you and your work, can you just start by sharing what your main focus is?

    Strickland Holloway, Jr (02:51)
    I’m here in St. Mary’s, Georgia. It’s where we’re developing. We have a waterfront community there that we’re developing and it’s for second homeowners, vacation owners, ⁓ anybody that likes boating, that sort of thing. That’s what we’re doing. And it’s pretty interesting development.

    Michelle Kesil (03:09)
    Awesome. And have you been developing for a long time?

    Strickland Holloway, Jr (03:14)
    Well, yes, I started out majored in real estate from the University of Georgia in 1973. I got my broker’s license in 76. I’ve got a real estate law degree. I got a law degree from University of Georgia. I’ve been practicing real estate law since 76. So it’s just a natural progression as a real estate attorney. I just kept buying and selling property and one thing leads to another. You wind up developing.

    And it’s just a matter of progression, you know.

    Michelle Kesil (03:46)
    Yeah, absolutely. How did you get started ⁓ with your first developments?

    Strickland Holloway, Jr (03:52)
    How did I get started? that’s interesting. When I was 26 years old and I first started practicing law, I was ⁓ 30 days out practicing law. And I walked by the courthouse and a lawyer was having a real estate auction, an estate sale at the courthouse. And I was just watching to learn. didn’t, planning on buying anything, but ⁓ it wound up that they no-sailed it that morning at ⁓

    around $170 an acre, believe it or not. so I looked at it and they were gonna come back that afternoon and open the bids back up at two o’clock. So I happened to call my dad and I said, look, I think I’ve got a chance to buy some property for $200 an acre. What do you think? He said, well son, if it’s just nothing good, but just to hold the world together, it’s worth $200 an acre.

    He said, go look at it. So I ran out, looked at it, came back, make the long story short, I bought it. I had just enough money to put the down payment down and 30 days to figure out how I was gonna pay for it. So that’s what I did. And

    I wound up buying 277 acres for about $76,000. I sold off part of it to my partner who’s a real estate partner that I had in the law practice.

    and he bought 70 something acres. That left me with 200. And I wound up selling 50 acres for enough money to pay off what I paid for the whole place. And I kept 150 and then divided up into lots and sold that off. So it was a good development right out the gate. I learned early on that I could make more money signing my name on a note than I could practicing law all year long.

    So it kind of ruined me. got into the real estate early.

    Michelle Kesil (05:42)
    Yeah, amazing. And as far as what you’ve developed, what kind of projects have they been?

    Strickland Holloway, Jr (06:36)
    Well, several different projects. I’ve done a lot of different things, buying motels and converting them into apartments, developing lots on the Georgia coast and in Florida. I developed a project in Florida. ⁓ We sold out around $10 million in one day, doing a one-day launch where we had marketed for six months and then wound up selling it.

    and then sold out the rest of the lots right before the crash in 08. Then since then, I’ve been doing other smaller projects and then I’ve circled back around to another bigger project. I bought ⁓ six town homes and 38 lots in the development that I’m in now at Cumberland Palms. And I’ve sold the six town homes. I’m now developing lots to sell as fractionals on the rest. So we’re selling it.

    on a fractional basis.

    Michelle Kesil (07:31)
    Awesome. And how is that development going? Are you selling a lot right now?

    Strickland Holloway, Jr (07:36)
    Sorry.

    Michelle Kesil (07:37)
    How is that development going? Are you selling things currently?

    Strickland Holloway, Jr (07:40)
    Yes, we’re just now getting started. We’re just now marketing it and getting ready to run some ads and bring people in and start selling it. So I’m hoping to wind up working out my ability to do owner financing so that it’ll make it easier for somebody to want to buy something that instead of paying $750,000, $800,000 for a second home, they can buy something for $170,000 and have access to it more than they’ll ever use it.

    And then they can take those weeks that they’re not using it and swap them into other houses all over the world. We have a program set up for that. And they can also rent them out and make money with them to pay for their interest. So it’s a unique concept. It really is one of the best ⁓ opportunities that I’ve ever seen as a developer. It’s just one of those things that came together at the right time.

    Michelle Kesil (08:34)
    Amazing. How does it work that people are able to swap around the world?

    Strickland Holloway, Jr (08:38)
    Well, you have, there’s a program called Third Home, if you’ve ever heard of it. A friend of mine actually developed that company and it’s pretty unique. If you have a ⁓ really an upscale property that they will approve, then you can put that into their program and swap one of your weeks in your home for one of their weeks in another home that they’re working with. So it’s a unique concept. ⁓ It’s better than

    than anything I’ve ever seen to be able to swap and go somewhere else besides just staying in your one unit all the time.

    Michelle Kesil (09:15)
    Yeah, definitely that is a great concept.

    So what are some of the main keys that you feel have made the biggest difference in allowing your business to be able to grow and to expand?

    Strickland Holloway, Jr (09:27)
    Yeah, I you can go anywhere in the world by swapping and you can, like I said, can rent your weeks, you can save the time and rent them out if you want to or swap with somebody else in the community. So it makes it a lot easier and easier to sell because if you want to sell it, we have a resale program to put it right back into the market and do that as well.

    Michelle Kesil (09:48)
    Yeah. Are there any drawbacks to this type of development?

    Strickland Holloway, Jr (09:49)
    Thank you.

    Yeah, know, financing is the major issue for anybody. On a second home, it’s just, unless you have cash, it’s hard to come up with financing sometimes. So I’m working on a program to be able to offer financing with a little bit of money down, and then they can have owner financing and make it very easy to get into it. And it’s kind of…

    In the way I’ve looked at real estate, it’s always anything I’ve ever bought and anything I’ve ever been paying for, it’s kind of like a forced savings account. I don’t have a lot of money cash going into a savings account, but I got a lot of money cash going into real estate, which has always been good as an appreciable asset for me. One of the first things that one of the gentlemen told me when I first started practicing law was to buy anything, anybody will sell you.

    as long as they are offering owner finance. It didn’t matter what it was, he said, buy it. If they’re offering owner finance, it’s always a good investment. it’s always been a way I bought property. I bought millions of dollars worth of property on owner finance.

    Michelle Kesil (11:00)
    Awesome. So what type of other investment properties do you have?

    Strickland Holloway, Jr (11:00)
    You see?

    You know, just I’ve got, I bought one property that ⁓ we were going to do an RV resort, high end RV resort, and we got ready to develop it. And of course, ⁓ we ran into some environmental issues and the property was high ground, but they came back and DNR said it was all wetlands. So we couldn’t develop that. But we then turned and found out that it was land that had been disturbed by

    the state of Georgia and the federal government when they built I-95 running through Georgia down to Florida. So if you take that property and restore it back to Marsh, which is what we’re now in the process of doing, you can create what is called a tidal mitigation bank. ⁓ Wetlands mitigation are fairly common because you can find wetlands just about anywhere.

    But finding marsh that has been disturbed by man is hard because nobody’s running a bulldozer out into the marsh by accident. You’re not doing that. So this property was messed up and destroyed back in the 60s. We’re now going to restore it. And we’re creating a title mitigation bank that actually creates credits that the feds issue. And the state of Georgia, Georgia Power, the Port Authority, anybody crossing the marsh with a road or

    power line or dredging, they have to have those credits. So we’re creating about 500 credits there and we can sell them back to those entities, which is really going to be a blessing because it makes more money than the RV resort did. So it turned out good for us that it was, we had one door closed, we had to make way to get to another door to open it. you know, that’s why in development you have to be

    prepared to change. You have to be able to not let roadblocks get in your way. If they come, you’ve just got to find a way to get over them or under them or around them. And sometimes the whole marketing plan changes on the spur of a minute because things don’t work out like you’d hope to.

    Michelle Kesil (13:42)
    Yeah, definitely it’s important to continue to pivot.

    Strickland Holloway, Jr (13:45)
    I’m sorry.

    Michelle Kesil (13:46)
    It’s important to know when to pivot.

    Strickland Holloway, Jr (13:48)
    absolutely. You know when to pivot, know when to change direction and do something different if you need to. When I first bought this property at Cumberland Palms, I was going to sell the houses as short-term vacation rentals and let people buy them, put them back into one of the platforms that you could rent those on, VRBO, Airbnb, whoever. But the problem I found out right away

    was that St. Mary’s was not on the national radar. If you were looking for some place to go in Georgia, you’re looking at St. Simons or Sea Palms or Savannah, ⁓ maybe Jekyll Island, ⁓ and then down in Florida, you were looking at Amelia Island. Nobody had heard of St. Mary’s. But St. Mary’s, one of the greatest national parks in the world, is there. It’s Cumberland Island. Beautiful.

    untouched pristine island that’s been got wild horses running on it. It’s just a beautiful, beautiful property that was donated to the federal government years ago. And it’s a national park. People come from all over to see that park. There’s no place to stay in St. Mary’s because they only have a few hotels on the interstate. So our property I thought would be perfect for somebody to buy the house, put it back into a short term rental and rent it out.

    That didn’t work quite as well as I thought because the market was not there. It’s coming, but it’s not there yet. So I had to pivot and change and say, okay, what am I going to do now? ⁓ Fractionals. I’ll sell each individual share, then I don’t have to worry about them renting it out. They’ll use it themselves.

    Michelle Kesil (15:31)
    Yeah, amazing. Sounds like a great opportunity.

    Strickland Holloway, Jr (16:15)
    It is, it is, really is, because not many people are doing this. You’ve got a few people that are buying a fractional in certain locations, high-end locations like ski resorts and that sort of thing, but there’s not much for the average person to be able to buy because there not any developments that are totally nothing but fractials. I created my covenants, which was a little bit unusual, I created my covenants where you can’t even live in my neighborhood.

    permanent residents live there because I didn’t want anybody coming and going having a good time as a short-term vacationer making some permanent resident angry and wanting to complain. So no one lives there. You can’t live there on a permanent basis. You can stay as long as you want. You can stay there six months, a year out of the time. I don’t care, but you just can’t call it home because I want to be able to have it open for weddings and wedding receptions and

    bring people in and rent the houses and then they can take and have a nice wedding at the wedding venue that we’re going to be building. They can get on a yacht, leave the wedding and drive all the way to Miami if they would like. So I think there’s a lot of destination weddings that will be taking place there. There’s going to be a lot of ⁓ renters coming and going wanting to rent those houses. So people that buy those units and those fractions will be able to rent their weeks out. ⁓

    on a very regular basis, I believe.

    Michelle Kesil (17:45)
    Yeah, that’s really exciting.

    Strickland Holloway, Jr (17:47)
    It is.

    Michelle Kesil (17:47)
    Yeah,

    go ahead.

    Are there any other developments that you are foreseeing for the future?

    Strickland Holloway, Jr (17:55)
    Possibly. I’m looking at short-term, that’s what I want to call it, it’s a storage unit. Let’s just think about a storage unit. Everybody rents those storage units. In a market that’s booming and you got a lot of people influx coming in, like our market in this area, they need storage. They bring in junk with them and they need to store it or they’re getting ready to move, they need to store it.

    But a lot of people, once they live there, they need to store things on a permanent basis. And not everybody has access to large tracts of land to live on. I happen to live on 100 acres, so I can put storage buildings anywhere I want to. But the average person’s going to be living in a neighborhood, and they don’t let you do that. So I’m thinking about building storage units, but then selling them on an individual basis. And that way,

    You can buy the unit, keep your prized car in it, your prized boat in it, or your prized antiques, whatever you want to keep, and not have to worry about paying rent. You own it. Now, if you don’t need it, then you can rent it out yourself and make money with it. But I think there’s a lot of people that would like to have a place that they can just store stuff and then use it at a later time. So yeah, I’m thinking about doing that as the next project. ⁓

    probably going to be doing some more developing as well once I find the right property and do that as well. ⁓ I’ve always tried to make ⁓ more right decisions than I do wrong. I’ll share this story with you. had a, when I first started practicing law, one of my law partner, who was an older gentleman at the time, told me to ride with one of our clients to his home to pick up some papers. And this guy was one of the most prominent

    members of the community had more money than anybody. But you couldn’t tell it. He was driving an old beat up pickup truck and overalls, you couldn’t know he had $5. I’m riding with him and he says, son, I like you, I’m going to share the key to success. And so I leaned forward and listened to him and he said, hold your arrows to a minimum. I’m sitting there and I thought, that’s real profound.

    And then he follows it up. says, in other words, what I mean is try to make more right decisions than you make wrong. He said, don’t be afraid to make a decision. He said, you’re going to make some right and some wrong. As long as you’re making 51 % right and 49 % wrong, you’re moving ahead. You may be moving slow, but you’re moving ahead. He said, try to get you, if you make 60 % right, you’ll make a living. If you get it up to 70 % right, you’ll be a millionaire.

    He said, if you can get it up to 80 % right, you’ll be a multimillionaire. He said, so don’t be afraid to make a mistake. You’re going to make them. Just learn from it. Don’t make the same one again. And try to hold your errors to a minimum. And I thought that was some of the best advice I’d ever heard. I’ve never forgotten it. And I always share it with young people because we’re all afraid to make a decision sometimes. And you can’t be afraid. You just have to shoot first, ask questions later.

    That’s how I’ve always done stuff in real estate.

    Michelle Kesil (21:08)
    Amazing. I think that is powerful advice.

    Strickland Holloway, Jr (21:08)
    Amazing.

    I’m sorry?

    Michelle Kesil (21:11)
    That’s powerful advice. Thank you.

    Strickland Holloway, Jr (21:13)
    Yeah, it is. I mean, it’s simple. Like he said, holds your arrows to a minimum. I didn’t think much of it at first, but then when he followed up and explained it to me, I realized he was right, and I’ve always tried to do that. I always hedge my bets. I don’t gamble. I don’t go to Vegas because I gamble for a living. Doing real estate is a gamble. It’s not a guaranteed thing. Of course, if anybody in real estate knows, you make your money when you buy it.

    Not when you sell it, the selling of it is just down the road, but you make it the day you buy it. I know what I’m going to make on something the day I buy it. It may take me a certain amount of time, interest to carry and all of that factors into it. you can make a certain money if you can do it quicker, you make more. If you do it slow, you make less. It’s not that complicated. Pretty simple.

    Michelle Kesil (22:01)
    Yeah, amazing. Well, before we wrap up here, oh, sorry, what did you say?

    Strickland Holloway, Jr (22:02)
    I’m sorry, I was going

    to tell you I’ve got one more thing I will share with you. This was pretty simple too. A friend of mine when I first started doing real estate, he said, look,

    Michelle Kesil (22:11)
    Go ahead.

    Strickland Holloway, Jr (22:17)
    There’s several ways to make money in real estate. One is to buy ugly and make it pretty. Of course, that’s the fix and flip model. Another is to ⁓ buy in wholesale and sell at retail. That’s the land guy that buys a thousand acres and busts it up into 50 acre tracks. So he’s buying it wholesale, he’s selling it at retail. The next way is to change the zoning character. If you can change it from one zoning level to a different zoning level and make it more valuable,

    taking it from residential to commercial, for example, ⁓ then you can make money doing that. Well, if you put all of that together, you buy ugly, you make it pretty, you buy in wholesale and sell in retail, and you take and change the zoning character, that’s developing. That’s all that is. You’re putting it all together in one piece, and that’s the ultimate way to make money. So that’s why I develop. And it’s fun. It’s creative.

    Michelle Kesil (23:12)
    Definitely, thanks for sharing. Before we wrap up here, if someone wants to reach out, connect, learn more, where can people find you and connect with you?

    Strickland Holloway, Jr (23:21)
    They can. My website is www.cumberlandpalms.com and I’ve got a contact page there that they can reach out and contact. They can also call me. Listen, I answer my phone. I’m not young. I’ll answer my phone when they call. So they could actually call me. 912-486-4477. I’ll answer it any time you call unless I’m on the phone.

    Michelle Kesil (23:46)
    Perfect, appreciate your time, your story, your perspective. Thank you for being here.

    Strickland Holloway, Jr (23:50)
    Thank you for having me, enjoyed it.

    Michelle Kesil (23:52)
    For the listeners tuning in, if you got value, make sure you’ve subscribed. We’ve got more conversations with operators who are building real businesses. We’ll see you on our next episode.

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