How David Denniston Plans to Build a $10M–$20M Land Investing Business Through Subdivides

David Denniston (00:00)

As a matter of fact, two weeks from today, we’re scheduled to close on a $1.1 million purchase that we’re going to—it’s an exempt subdivide. And so we’re splitting it off into 15 different lots. And we think, cross the fingers on the low end, we believe,

it could sell for 2.2 million. And maybe we net, because there’s various expenses, we’re putting in some roads and stuff, we’re hoping to net 500 or 600 grand. Well, gosh, if we could do that every single month, we have an eight-figure business and a very, very profitable one.

Issa Hanna (02:03)

Welcome back to another episode of the Real Estate Pros Podcast. I’m your host, Issa Hanna, and today I have a treat for us. I have somebody who’s bringing in a knowledge of something that a lot of us investors don’t really know about—Dave Denniston. Dave, welcome.

David Denniston (02:16)

Issa, thank you for having me. So glad to be here.

Issa Hanna (02:18)

I’m—I’m super excited to have you. You are a land expert. You are one of the top guys in the whole country in terms of knowledge on land acquisitions and land sales. But first, I kind of want you to break down Generational Family Properties, generational family land, what you’re kind of doing right now, and then what your day-to-days kind of look like right now.

David Denniston (02:37)

Yeah, for sure. So I got into land back in twenty seventeen, and so been at this almost 10 years, going on pretty here soon. So it’s been a wild journey and started out doing a bunch of cheaper properties. And I did that—a lot of that—so much so I had about 500 notes at one time, owner-financed notes. And so then I was like, “Well, I think I’ve gotten this about to where I wanted to with the brain damage I had.” And so—

could talk more about that process either later today or a different time. But basically today in GFP, as we call it, Generational Family Properties, we’re really focusing on subdivides. So taking a big piece of land and chopping it up into a few different pieces and then selling it, hopefully for significantly higher than what we bought it for, as well as we still have a lot of tax lien

foreclosures and some tax auctions and stuff like that we participate on to acquire land. And then, you and I were talking earlier, I’ve been dipping my toes into messy title-related stuff in Texas with both homes and land. So that’s kind of what I’m doing today.

Issa Hanna (03:40)

Man, I love that. Natural progression, natural vertical scaling of your base business, and then you’re getting into anything or other things. The messy title stuff, that kind of stuff is very often overlooked. It’s really not that hard to resolve some title issues, especially if it’s only a couple owners. So for our investors at home, definitely an avenue you want to look at when exploring acquiring

properties for a little bit cheaper, for a little bit better of a price, because our friend is equity and we’re always trying to find that next good deal. So definitely, I’m glad you brought that up. And then Generational Family… I love the name. Can you kind of give us a little backstory on why that name, why you chose that name?

David Denniston (04:19)

Yeah. What I—as I was starting the business, what I was trying to ask myself is: Who are we trying to serve? And who’s our avatar? And at the time it was: Here are people that we are buying land from, and we’re selling it where it’s very, very affordable for the normal person. Again, this was our—our version 1.0

of the business. And so my thought was, “Hey, this is something that could bless multiple generations of a family.” A low barrier to entry—someone with 200 bucks down and a hundred dollars a month could afford a piece of land like this, and that could be passed in their family for generations. And so that’s basically where it came from. And then I used the name “Properties” on it rather than “Land,” just in that, well, what if I want to do houses eventually or something like that?

And here we are now looking at messy title, and I think coming full circle to that idea.

Issa Hanna (05:09)

I love that. That’s why I said I love the name. And then also, peeking at your website, you yourself are a huge family man. You love to travel, you love doing all that stuff. So one thing also per your website, it called you a nerd. I don’t think you’re a nerd for it, but these Risk—the game of Risk, these strategy games that you like to play, I feel like it translates well to decision making. So can you kinda

give us a little backstory on your personal life, some places you’ve traveled, the family, and what you’re bringing in like that?

David Denniston (06:28)

For sure. Yeah. If you ever have the chance to meet me, I am definitely very introverted by nature. If I’m in a room of people I know, it’s cool, but I love one-on-one conversations like we’re having right now. But if you get me in a room with like a hundred people, I’m hugging the wall. Like, I am feeling nervous, kind of anxious, and ki—if I don’t know people especially, it’s a difficult thing for me.

And that’s why I like a lot of games and nerdy stuff. I grew up reading a lot of comic books, DC and Marvel, and I played Risk with my dad. There’s a great game called Wildcatter that’s like Monopoly, where you drill for oil wells, which is really fun. So I grew up enjoying those things. And I think it really definitely has been an influence in terms of thinking about investing and thinking about

strategy and how to attack a problem, and that there’s never one solution and you have to constantly adapt and pivot, as I’ve been describing a little bit with the real estate business. We have pivoted several times, and I’m continuing to learn and grow. I really appreciated the comment earlier calling me a land expert, and I feel I’m still learning all of the time, different things, and

of course I know a lot more than I started. But man, just trying to be a lifelong student and continually get coached and understand and get developed both as a human and in business. In terms of my family, gosh, we definitely enjoy traveling. Again, being more introverted, I enjoy experiences in a small setting. So I’ve done a variety of masterminds over time. My family and I

have gone to the Philippines, Switzerland, Germany, Greece, South Africa, all kinds of places. And really, real estate through land has afforded me that wonderful opportunity in the fact that I could work on my laptop. China was another place, New Zealand, that my wife and I went to. And I’ve been able to work on the land business literally in every single one of those places that I named. So

don’t get me wrong, it’s a lot of hard work. It’s not like I was just sitting on the beach hanging out. There’s a lot of stress that comes with it. But man, what a great way to experience life and expand our horizons and enjoy so many different cultures and places.

Issa Hanna (08:43)

Definitely, man. Real estate has afforded us a type of life where, yeah, like you said, it—it’s work, there’s stress, there’s whatever, but at least we could be on the beach having the stress. And then, we can look up and be, “Okay, I’m on the beach,” or something like that. It’s given us—it’s bought us something that is priceless, and that’s time with our families. And that’s why I brought up the family and how you’re a huge family guy. And then yeah, those—those strategy games, man, they translate so well.

And another thing that translates so well with you is you were a financial advisor. So you have a background in financial advisory in the financial world, which is huge in real estate and goes hand in hand. So can you kind of give us a little background on the financial advisory, and then what made you switch—switch over to our side of the—to the dark side of real estate?

David Denniston (09:27)

Well, this is—this could probably take a whole twenty minutes, so I’m gonna try and keep it relatively short. But essentially, I grew up in Southern California, did my undergrad in Seattle, graduated ’03. I started in financial planning in ’02 as an intern, and then did some door knocking through Edward Jones. And again, I’m—I’m nerdy. Going out and doing sales stuff was extremely uncomfortable and difficult. And I grinded it out

and got some stuff going, but then I ended up joining another financial advisory practice as staff and grew there to the point where I’d received some inheritance from my great aunt. And I said, “Hey, I want to buy into the practice.” And he was my boss at the time, said, “No. Good luck.” And so I said, “Fine.” And so hunted all around the country, ended up finding Minnesota, of all places, and closed on a three-million-dollar

acquisition at the time. Guess what our close date was?

Issa Hanna (10:22)

What was it?

David Denniston (10:23)

August 1st, 2008. Great

Issa Hanna (10:25)

Really?

David Denniston (10:26)

timing. And so again, I could go on and on and on about some of the stuff that happened. But long story short, I had pushed in all my chips on the table. And I was going through that process and everything. There was some lies and there was some misrepresentations, but there was also what was happening in the world. And I was like, “Man, I might have to go

bankrupt, and what the heck’s gonna happen?” And so I determined at that point, I am never gonna be solely dependent on one income source ever again. And so I had that seed planted, just really scratched and clawed my way through that time in the next few years, and things got better over time. 2012, my youngest daughter was born, and she was due in September. She came out May 13th of 2012.

And so we were in the NICU for months and months. She didn’t get out till past her due date. And I was really so grateful to the physician community. And so with my financial planning practice, I started a podcast, The Freedom Formula for Physicians. I don’t do any episodes now today, but if you look on iTunes, it’s still there. There’s like eight or nine seasons, hundreds of episodes that people could listen to.

And my land journey is on there. I talk about some of the stuff that happened in land. And so here I’m—I write books, start looking at different multiple income streams. And at the end of the day, to make a long story short, I had a guest on my podcast that talked about land. And I was like, “Huh, this is kind of interesting.” My parents had done real estate, rental real estate, and I hated it. But this flipping paper where I didn’t have to fix stuff and deal with contracts,

that really—or tenants, that really rang a bell with me. And I never stopped my financial planning practice.

As a matter of fact, I’m still doing it today. So I’m still a financial advisor with a great practice. We manage about 90 million under—under management, and I have a lot of help, but I am the person running the company and

the CCO and everything. And then we have the land business. And my land business over the years, again as we’ve pivoted and done stuff over time, grew from having nothing to having a hundred thousand. I was like, “Man, if I could make an extra hundred thousand dollars from this business, that would be amazing.” And then you get there and you’re like, “Dang, this is—this isn’t what I thought it would be. This business is requiring a lot more capital than I thought.”

And so you just kept on piling it in, piling in, piling in, and here we are today. We have probably three hundred and fifty owner-finance notes. We’re probably this year working towards four million of revenue, so a very substantial business. We have about twelve people on staff, and that’s—that’s the story of a very shortened, compressed version of how we’ve gotten to where we are today.

Issa Hanna (13:15)

Man, I love it. And I know as a real estate agent, what made me want to get into buying rental properties was I didn’t want to be dependent on that one stream of income, right? So I wanted to get into something that I knew that I knew was going to bring me in another stream of revenue. That way, if I don’t close any sales, if I don’t get any clients, I’ve got this guaranteed money. So I can definitely relate to exactly

what you were thinking with that. And then getting into the land acquisitions, the idea—is the light bulb going off while—while you’re talking to somebody like, “Hey, I think I can do that.” A lot of people get into—to their—their specialty in real estate just like that. But the way you’ve been able to become so knowledgeable on it, and with the background you’re bringing into it—with the parents, you’re the son of landlords, so

it—it’s a lot of knowledge. It’s like the perfect storm to be able to grow that land business to where you’ve grown it. And Generational Family, different pivots, and now it’s Properties, and you’re—and you’re scaling up. So I can see the future being very, very bright for the real estate business, as well as the financial advisory. And speaking of the future, five years down the line, I see a bright future, but everybody has a five-year plan. Do you mind sharing your five-year plan with us?

David Denniston (14:28)

Yeah. So Issa, I’m—I’m 45 this year, and I really have a vision for when I’m 50. Now I don’t know the exact path to get there, but I’m—I’m hoping, and as I’ve mentioned at the beginning, I want to have multiple income streams. I have multiple things going on. What I’d like to do with all the businesses is get to the point… Right now I’m—I’m owner-operator, right, so I’m doing…

I’m not doing everything in any of the businesses. I’m doing some of it, with the idea of: What does it take to scale? How can I grow and develop people and speak into them? And I’m hoping that we can get the land business to be a 10-million, 15-, 20-million-revenue-type business. In order to get there, we’re really gonna have to have multiple

things going on. I think subdivides are a great way to scale, because we’re buying stuff for 400,000, 500,000, 200,000, a million.

As a matter of fact, two weeks from today, we’re scheduled to close on a $1.1 million purchase that we’re going to—it’s an exempt subdivide. And so we’re splitting it off into 15 different lots. And we think, cross the fingers on the low end, we believe,

it could sell for 2.2 million. And maybe we net, because there’s various expenses, we’re putting in some roads and stuff, we’re hoping to net 500 or 600 grand. Well, gosh, if we could do that every single month, we have an eight-figure business and a very, very profitable one.

So that’s—that’s what we’re aiming for. And I’m hoping as we have messy title, that’s another business that makes some money. Eventually, as I work toward 50, I’ve been—I mentioned hard money,

I’m building up a lending portfolio, so I’m hoping to get that to a million dollars, because if I can make 15 to 18% on that money, there’s 150, 180 grand a year. And that particular side is very high return on time. The land business is extremely time-intensive. My financial planning business is extremely time-intensive. And so by the time I get to 50,

I want to get to the point where I have more time freedom than I do right now. Now, technically, I could be as free as I want, right, but in order to hit the goals and the vision of what we’re trying to do… I mentioned my youngest daughter. She’s someone that’s—that’s kind of special needs, and so I’m trying to plan for her future. My wife is—has a missions organization, and so it’s on our heart for our faith to do stuff across the world and help

people. And so we need finances and resources with which to do that. So we’ll see where it goes, but that’s—that’s the vision, and that’s what we’re heading towards.

Issa Hanna (17:09)

I love the vision—a truly noble vision. Giving back around the world, not just in one community. You’re going, you’re identifying where things need help, and then you guys are going there and helping. Very, very noble. Definitely praying that this goal be achieved. I totally have faith in your knowledge, your background, and your vision that you will definitely achieve that a hundred percent, David.

Truly, truly inspiring work that you’re doing, man. It’s unbelievable. I want to ask you for our younger viewers now. I want to pick your brain a little bit for our young guys, the guys just starting out in our professional world, because you’re—you’re vertically scaling in finance and financial advisory in the real estate service field, so you’re everywhere in the professional field. This all depends on, and it’s—and it’s a play to something you told me earlier, one of your strengths: connections, right?

Establishing those business relationships, growing your network, super important in our business. So if you had to give somebody one piece of advice that was just starting out, what would that one piece of advice be?

David Denniston (18:10)

I’ll make it two parts, actually. So I think, if that’s okay, I think number one, as a young person, there’s—there are moats around starting a business. There are incredible people that do start out businesses with almost nothing, but that’s very unusual. And so find somebody, whether someone on this show or elsewhere, that is an investor and learn from them. Be part of the staff, be coachable,

and really don’t come with a bunch of assumptions. Really be hungry, be humble, and ready to learn and grow, and see how a business operates. And once you get an idea of, “Here’s what I like and don’t like,” and we’ve saved up some money, well now go—go ahead and go for it and start your own and do your thing, if you have an entrepreneurial heart and bent to you.

But I think there’s something to be said for building up a little bit of a base for yourself. Now, there are exceptions to this. There are amazing entrepreneurs that start really, really young, and I think that’s the exception rather than the rule. So if you are that entrepreneurial person, don’t let me hold you back—go for it. But everyone else do. I think the other piece of advice I would give to a young person getting going

is really the time to take risk is when you’re young. And by the time you get older, like myself, having a family and ol—aging parents and stuff like that, man, what a great time just to work your butt off and spend a lot of time. Now, live life, enjoy it, but I think your twenty—your tent—your teens, your twenties are the time really to

hunker down and learn as much as you can, and work as hard as you can. So that’d be my advice, two-pronged, to young people just starting out.

Issa Hanna (19:53)

I love that advice. And fun fact, man, when I was about eighteen, nineteen years old, a very successful person, who’s the uncle of one of my friends, told me the exact same thing. He said, “If you guys grind and you work right now in your late teens, early twenties, throughout your twenties, your thirties, your forties are gonna look so much better. You’re gonna be able to build such a base.” So you young guys, like Dave said, hunker down,

get it done. If you have that spirit, go out and try that business. You never know what could happen. We all got into real estate because we said, “Hey, let’s decide to try it.” We realized we can make some money, a big fat paycheck came in, I said, “What? This is the way we want to go.” So man, golden advice, Dave, golden advice. And now I want to give you the floor. If people wanted to get ahold of you, they wanted financial advisory services, they want to get ahold of

Generational Family, how could they reach—

David Denniston (21:26)

Yeah, for sure. Well, thank you so much for the opportunity and being here. Really grateful for the time to share some of my story. I hope everybody listening can relate to pieces of it as you go on your own path. I think for me, certainly if folks want to find out more about partnering with us, you’re certainly welcome to check out our website at genfamland.com, G-E-N-F-A-M

land.com. I think my contact info is on there, or you can reach out through the contact thing if you want to get ahold of me. My financial planning website is daviddenniston.com, so if you want to learn about financial planning services, that’s the place to go. And then I also have a heart for land investors in particular, and so if you’re someone interested in land investing or you are a land investor

like myself, or you’re just curious about it, go to leadershipinland.com. And I have now two years’ worth of content, three years’ worth of content we’ve developed there, free. We have a Skool community, we’re part of the REtipster broadcasting network, so a lot of great stuff. And I give—I give real insight into my business. If you want to learn about

what does cash flow look like for Dave’s business, what is revenue, expenses, what are the goals, I talk about all of that kind of stuff in the leadership struggles and hiring along the way. And lastly, for anyone that’s an established land investor, I do put on mastermind events from time to time, so if y’all interested in that, landunconference.com is a great place to go.

Issa Hanna (22:59)

Guys, make sure you check Dave out. Like I said, one of the top guys in the country in terms of land knowledge, in terms of just financial advisory. Somebody like him could really help you. So if anything we talked about today caught your attention, make sure to go check Dave out, because he’s your guy. Dave, thank you so much once again for coming on. And I invited you earlier off camera, but I wanted to be live on air: I want you back on the show at a different date if you’ll have us.

David Denniston (23:25)

I would love to. Thank you again so much for having me, then.

Issa Hanna (23:27)

Thank you for coming on. It was a true honor. It was very inspirational talking to you, and I know our viewers are going to get a lot from it. And to our viewers at home, if you enjoyed my conversation with Dave and want to see more like it, make sure to hit like and subscribe. I talk to people every day that can bring us different knowledge on every aspect of the real estate industry. Until next time, the Real Estate Pros are out.