Seth: Hey, everybody, how's it going? This is Seth Williams from REtipster.com. Today, I'm talking with Ann Danielson. Now, if that name sounds familiar, it's because back in 2024, we had Ann on the show with her sister, Mary. They were running a really unique land business together with two completely different personalities, working across time zones, building a lean operation that was doing some impressive subdivide deals. But today's conversation is a little bit different because Ann is at a completely different point now. She's stepping away from a decades-long career, becoming an empty nester, moving back to the U.S. from the Philippines, and going all in on land—all at the same time. And what makes this interesting is it's not a clean, polished transition. It's kind of messy, it's uncertain, it's exciting, and honestly, there's a lot at stake. So today we're going to talk about what happens when the side hustle becomes the main thing, and when your identity and your income and your future all get tied to a business that still has a lot of unknowns. So, Ann, welcome back. How are you doing?

Ann: I'm great. Thanks for having me, Seth.

Seth: Last time we talked, you and Mary were running this as a pretty tight partnership. Is that still the situation today, or how would you describe what has changed in your business and your life since then?

Ann: Yeah, actually not a lot has changed since then. We've just stayed super focused on Tennessee—even a micro-focus on Middle Tennessee. I guess we've gotten even tighter. We tried out a couple of VAs, we played with a few things, got tempted, but we're back to where we've always been, which is just Mary and Ann.

Seth: What kind of things were you playing around with that you decided not to pursue?

Ann: We tried cold calling, and we did not like it that much. We never tried texting. We actually stopped mailing about two years ago. We tried hiring a VA to help with just some administrative things, and we're back to bare bones.

Seth: So am I hearing what you said? You tried cold calling, didn't like it; tried texting; you stopped mailing.

Ann: We never tried texting.

Seth: Oh, you never tried texting. Okay, that's right. But then you stopped mailing. Did I hear that right?

Ann: Yeah, we stopped mailing a couple of years ago, except we send Christmas cards to people that we like and stay in touch with. But all the blind offers and stuff, we haven't been doing. We're not saying we're done with it forever. We just kind of put it on hold because we were trying to focus on our inbound leads and building up our relationships. So it's not gone forever. We're definitely open to coming back to it, especially when we joined Stride. In a couple of months, yeah. But for the last two years, we have not.

Seth: Does anything feel different about your business now? Or about the way you think about it? Or is it pretty much working the same way it was before?

Ann: Yeah, I would say it feels a lot different. We got started when so many people did—about five years ago. And we also got lucky a lot at the beginning. It was easy to do well and be successful in those days. Our third deal was a subdivide, so then that just set us down that path. We grew with our deals and our partnerships and the size of our deals. We did some majors. So all of that was going really well. Luckily, at the end of '24, we made three really big purchases when I think a lot of people weren't really buying. And then those fed us, I would say, all through 2025. Just this last month, we completely closed out on one of those big deals. So we were sort of lucky to ride the wave of what we had purchased and had to really chew on and develop, because they were larger developments. But if we hadn't made those purchases in 2024, I'm not sure what 2025 would have looked like. And then that left us with our current dry spell.

Seth: Bring us up to speed. So you are a teacher, or you have been a teacher, for many years in the Philippines, correct?

Ann: My husband and I have been overseas since 2002. We actually became teachers because we wanted to live an international life. We knew teachers that had been international teachers. We grew up in a really tiny town where people don't… I mean, they go to like Florida to a timeshare on spring break and they drive, you know, save some money and not rent a car—which is, there's nothing wrong with that, that's how we grew up too. But we always had dreams that were kind of bigger. So that's what drove us to become teachers. We went to Malaysia and then on to Shanghai, China for 13 years. That's where we had our kids. And then things got very comfortable and lovely and easy in Shanghai, which makes us uncomfortable. So we moved to Ghana. And that was when the girls were in middle school. Then we have been in the Philippines now for seven years—until a month and five days from now, when we are moving back to America for the very first time.

Seth: It's a big move, coming back to the normalcy of America. I'm curious, why is it okay to have the normalcy of American life now when you used to be uncomfortable with it? Why are you coming back to that?

Ann: That is a great question. I don't think that it will be okay. I think we're really going to struggle, actually. We haven't been real adults in America. We haven't had winter. And we're going to Madison, Wisconsin. So I'm giving us until Christmas. And then I have a feeling that—well, the rest of our plan is we're going to move to Mexico to do some slow travel until we find a place we want to stop. So why are we moving back? I mean, a big part of it is the land piece, but also because our kids are both in university, or will be once graduating from here now, which is why we can finally—not finally, I shouldn't say "finally"—why we can go start a new chapter. But it was hard being in the Philippines with Hayden in California, and it'll just be good to be on the same continent.

Seth: When you say that it's going to be a struggle over here, like, why exactly? Is it the higher cost of living, or the familiarity of what you grew up with? What stands out to you that's like, "Yeah, we're probably going to have to go to Mexico"? Why do you even say that?

Ann: Yeah, I think that's true. I think the higher cost of living, especially this year—a lot of folks are feeling the burden of that. We've always been employees, right? We have a really nice package overseas, and they literally take care of everything—our house and our driver and our cook and our bills and our medical—and we want for nothing. We actually don't even see the bills. They just get sent to the company. So that's a pretty pampered and unrealistic lifestyle. So we have a lot of learning to do. And also as self-employed people, we've got to figure out health insurance, and our house is, like, falling down. So there's a lot of things that will challenge us. We will have to embrace the struggle. But yeah, it's not going to be easy.

Seth: For years, you've been running this business alongside your life. When did it start becoming something that actually needed to support your life? Is this kind of the moment when it's like, "Hey, this is no longer a side hustle, this is the main thing"? Or has it kind of been the main thing for a little bit?

Ann: In my heart, it's been the main thing for the last three years, I would say. But financially, we haven't touched any money until last semester. So last fall—no, Christmas—I paid a semester of Hayden's Berkeley tuition with my income from the company. And I thought, okay, this kind of feels good. So we haven't relied on the income, but now we might. We've been super frugal all of our years. We don't really buy much or do much. And because we're overseas, we don't really have to buy much. No one cares what car you drive, and we don't care about clothes. We do take big vacations. Aside from that, we just save a lot of money. So yeah, we've been good savers and we can live on a budget. We can make it work if we have to, but I'd rather not.

Seth: Yeah. Do either you or your husband have a job lined up over here, or are both of you just, "Nope, no job, this is all in"?

Ann: Yep, all in. And actually, Mark—that's my husband—he just started this weekend. He teaches IB. I don't know if you know what that is, but the International Baccalaureate. It's the international version of AP. And it's insane amounts of marking. It just ended this weekend. And so he asked me which podcast to listen to. And he was watching the screen. And I was like, "Honey, it's a podcast. You can just move around and stuff." And he's like, "No, I have to take notes." So now he's really studying land because he's excited to do something new too. He's starting fresh. He's our current intern, but he's going to find a new arm for the business that isn't in my lane and isn't in Mary's lane—because we've been really careful about that, to keep everything separate and everybody knows what their job is. And so right now he's just in the research phase, figuring out what he would want to bring to the company that we don't already have.

Seth: So he has never really played much of a part in your land business until now.

Ann: Yeah, no, not at all. Not at all. There's the hat. There's the hat.

Seth: So when you think of this major life transition in several different ways, what do you think is the hardest part to let go of as you're changing continents, changing professions in a way, changing your neighborhood, all that stuff?

Ann: Well, moving countries is exciting for us, and it's something that we're used to. That part feels pretty good. And even though I know it's going to be hard, we like that. We like figuring stuff out, even if it's our own country this time. But the hardest part is going to be not having kids at home. So like, for anyone who's had kids that leave—oh, that's so sad. I mean, I'm very excited for them and they're doing great things, but it's just going to be different.

Seth: Yeah, I actually think about that a lot. My kids are currently 9 and 11, but all the time my wife and I are talking about, like, "I wonder what they're going to do. What are they going to grow up and be? Where are they going to go? Are they going to move somewhere else? And if they do, are we going to follow them?" I don't know, like if they move to some other state, I don't know why we would stick around here. I have no idea what it's like, but I imagine it all the time. I'm sure it's a huge mental trip to go through that and figure out, like, what do you do once they're gone? Such a big part of your life, you know?

Ann: Yeah, it's true. It is. And we did some testing. So we kind of thought, "Okay, we'll go somewhere else when the girls graduate." And so at Christmas time, we tested what's it like to do the land business from Spain. And the time zone was so hard. I'm talking to you at night right now, but usually at like 8:20, I'm hitting the hay. So the time zone was really tricky. And then now when they're in university, they actually call you quite a lot. My daughter just got her purse stolen, and they're texting and freaking out and stuff. And when you're on the opposite end of the world, they're not going to hear from you until you wake up, or you have to leave your phone on. So yeah, it'll be good to be either in the U.S. or U.S.-adjacent. That's what we're calling it.

Seth: Remind me, how have you handled the time zone difference all these years? It's 8:20 a.m. where I am. It's 8:20 p.m. where you are. How do you run a business when everything happens when you're asleep? Do you just stay up really late, or what's the answer to that?

Ann: Well, I'm incapable of staying up late, but I can get up very early. So Mary takes care of everything that's a synchronous task. And then the whole time I'm sleeping, she's working. We have a document that we just kind of pass the torch back and forth on and we move things. And so our joke is that we're the 7-Eleven of land, because literally one of us is always working. And then we just carve out a big spot either on Saturday morning or Sunday morning, my time, where we have like a long meeting. Otherwise, we're on the fly all the time. And I wake up as early as it takes.

Seth: Mary—she lives in the U.S. I don't know how much you know. Does she like live off the money that she makes from land? Or could you kind of look at her as a snapshot of, "That's what my life is going to be like"? Because that's kind of what you're transitioning to, right?

Ann: Kind of. Actually, her husband has a very good living, so he can support the two of them. And then her land salary right now—both of us don't take that much. We take a reasonable salary. She spends it all on travel hockey and travel volleyball. That won't be my life.

Seth: Do you see this as more of a reinvention of yourself, or like a midlife crisis?

Ann: I think it's the beginning of something new. I'm talking to other people that are in our stage of life and I see them wondering, "What am I going to do when the kids leave?" And I'm pretty excited. I definitely have days where I'm like, "What in the hell am I doing?" But I'm okay with it. I think because I know when I commit to something, I commit. I know I'm going to work hard. We're five years in. I think I've kind of developed the blisters. I've got the experience now to go for it. And I'm excited. I think it'll be fun for Mark to learn. I think it's really good for the kids to see us trying something new and building. And I know we can do more, and we can do bigger deals now that I have more time.

Seth: So you mentioned these—I think it was three deals you got in 2024—and you've kind of ridden the wave and they kind of fed you. You didn't say this, but I'm just thinking out loud—it almost sounds like, is there a dry spell coming after this? Have you not been able to find other great deals like that since then? It almost feels like there's some moment of truth coming up like, "Uh-oh, can we make this work now that those great deals are gone?" Or what is going on with that? Is that a concern at all?

Ann: You know what, what you just described is exactly how I felt. Like, is this a dry spell? Is it in my head? Am I scared to take the leap now that the stakes are higher? This month has been really good, so maybe I've come out of it. But I was definitely in a paralyzed rut of, "Is it a deal? Is it a deal that's good enough?" It just felt so much bigger. I think almost right now, I feel like I was kind of just playing with house money and it was so fun and there were no stakes, and now the stakes feel a lot bigger. So I don't know. I don't know if the deals weren't good enough. I kind of think they actually weren't good enough, because my underwriting is conservative and I don't think I was unrealistic, but I do think I was just even more conservative, and the numbers and the margins were smaller, and I just couldn't pull the trigger on anything.

Seth: You know, it's a funny thing because I've tried to figure this out in my own life and also other people I know right now. Some people I know who are killing it in the land business, doing very, very well, and other people who have done well for a long time—like, they know this business, there's no question about it, and there's no question about their resolve or their willingness to work, the will is there—but they're struggling. And I'm trying to figure out, like, how much of this is skill and how much of it is luck? I think Paul Newman had some quote where he said something like, any successful person out there can never say they got there without a little bit of luck. There is some of that involved. I almost kind of think of that with your situation. Were those three deals luck, or was it some skill you had? What's keeping you from just waving the wand and making it happen again? I don't know if it's just a matter of, like, keep looking elsewhere until you poke around to find the right thing—because we all have a limited bandwidth. There's only so much time in a day. We only have so much money. There is a point at which you better get lucky or you're not going to keep finding opportunity. With your situation, are you in a spot where you can't find deals, or the ones you're finding just aren't as good as they used to be? Or, I guess, how serious is the dry spell problem, if there even is one?

Ann: Yeah, I think it's probably all of those things to some extent. And then if it's not working, what are you going to change? So I feel like I'm a decision maker and I don't sit idle. I grew up with a dad who said, "Do it when you think of it. Do it when you think of it. Do it when you think of it. Keep moving, keep moving." And so I did really try to analyze what I could change. We did try a couple of new things, like new types of deals. And the other thing that happened—and I don't know, I feel like it was the universe—a lot of, like, 22-year-old boys who live at home after university started reaching out to us with their deals, to the point that my husband was joking and saying, "Are we going to breakfast on Saturday? Are you meeting with your 22-year-olds?"

Which is fine, because he could go golf, and he likes the 22-year-olds and the deals that they bring. But I think it's an interesting relationship that just sort of grew, but also great, because these guys are all super resourceful, so smart. Some went to university and some didn't. They're in the grind. They're willing to just do anything to make it work, and they don't have any money and they don't really have experience with a deal. So I think that Mary and I aren't very threatening. For a guy who is a little bit intimidated by the bros, you know, maybe doesn't want to reach out because maybe their deal isn't good or they're not feeling very confident—but for us, and I'm a teacher, so I'm happy to help you through it. And if it's a great deal, I'm happy to buy it. So yeah, that's been kind of a blessing recently. We love it. If you're out there—no, just kidding.

Seth: Just kidding. How are these guys finding you? I mean, this is something great people would want to know.

Ann: I don't know. I don't know. Maybe our identity is really clear, right? Like, we're the sisters, we're in Middle Tennessee, we subdivide. So then I think if they think, "Oh, is this a subdivide in Tennessee? Oh, I'll just call those girls or those moms and see what they think of it"—which is great.

Seth: Am I correct in understanding the reason you're leaving the Philippines is because your kids aren't there anymore, right? They're all over here. So why are you over there? Is that kind of the crux of it? Or is there another reason? Why wouldn't you just kind of stay where it's safe, stay where living costs are cheap, and you can keep doing what you've been doing?

Ann: I don't think we've ever been people to stay where it's safe. Almost the opposite. Like, if it gets too easy, we get too bored. Right now we have a seven-week, no-repeat food plan, and we get a different meal every single night for seven weeks. Like, everything is curated and perfect and very boring. So I think we're ready for a challenge. And also we're ready to be done teaching. We're ready to be our own bosses. Teaching has been beautiful and awesome and we loved it. But since COVID, kids are different. And in the Philippines especially, we had a really hard lockdown. So they were used to—I'm an art teacher, so they were watching art tutorials. But to think creatively, or to sit with a problem and to try different solutions and to be patient and to chip away at a problem—it's not really working. Their attention span isn't there. And they just want, you know, an iPad. So it's been frustrating in the last couple of years, and part of it I know is because of that, but also because I've changed as well. And when I'm teaching perspective drawing for the millionth time, I'm picturing all the things I'd rather be doing with my land business. So it's just time. We've been teachers for a long time, and it's okay to do something else, even though teachers have a hard time leaving the profession because it really is our identity.

Seth: So it sounds like the reason that you couldn't just stay the path is because it's boring. Is that accurate, or is there any other reason why you couldn't just do what's safe?

Ann: My soul would slowly die.

Seth: Yeah, I get that. What kept it from dying all these years, then, when your kids were there? Because you've been there for a long time, right?

Ann: Yeah. And I would say for the last three years, I was ready to go, but the girls were in high school, and they were really into school, and we wanted the schooling for them. It's just a great school, but they also play sports, and it's their community. And we always said we could move them three times without messing them up. So we didn't want to try another country, and everybody was really happy here in Manila and at the school. So yeah, it's just a clean break, right? Letting them graduate and getting them sorted at uni, and we all head out together with just a few suitcases. It should be a piece of cake.

Seth: Have you ever had it where you've taken one of these leaps, done the thing that wasn't safe in the name of not taking the boring path, seeking adventure—and it ended up burning you? It hurts you long term. You probably should have taken the safe path. Or has that never really happened to you?

Ann: The only safe path that I've taken has been marrying my childhood sweetheart, which everyone thinks is really—you know, not that they think we're a good couple, but it just seems kind of lame that you marry the person you grew up with your whole life. It wasn't a risk, and it did actually work out. And then taking a plunge—that's what I'm trying to rest on, is like every time that we've tried it before, there's been rough patches and it's hard to launch sometimes, but it's worth it, and change is good. I'm trying to remember that. Those are the words also in my brain: "You've got this. You know how to make change. You want to grow. It's going to be hard. Do it."

Seth: So if you guys come here and things don't pan out, you can't find good deals, it's just not going well—what is the backup plan? Or do you have one?

Ann: I think a backup plan is for the weak. I think if we said, "Oh, we'll just be substitute teachers, or we'll just get a job teaching, or we'll go back overseas and teach," I don't think we would be hungry enough to make it work. I think I would feel like I let myself down and I'm a failure. So I mean, if the model that we're doing currently in land needs to pivot or change or grow, I'm absolutely willing to do that. But I think I'm definitely burning the ships on teaching, because I want to try something new.

Seth: Is there ever a universe where you would go back to teaching? Like, what would have to be true for you to try that? Or is it just like, "No, I will absolutely never do that again"?

Ann: I think I would teach adults. I think I would teach adults. I'm done with middle school boys—I can say that for middle school.

Seth: I can understand that.

Ann: There's no universe. And I think my guess is—so let's just picture what I think is going to happen. I think we'll end up living in Mexico at least next year. I'm pretty sure Mark will end up coaching with some community team or whatever. And I'm sure I'll end up doing some kind of art with, you know, volunteering with a local school or local church or something like that. But to have a principal—I'm never going to have a principal again. I'm graduating from teaching.

Seth: Yeah, this is kind of a random story, but my family, we went to this high school football game this past fall, and somehow all the seats were taken. So we had to go and sit in the area with all the middle-school-age kids, and the whole area just stunk like body odor so bad. It's like they're at that age where they don't realize they need to start wearing deodorant yet. It's just something that hasn't kicked in. But anyway, do you get that a lot? Is that a common thing in middle school classrooms? Do you ever get used to that, or no?

Ann: No, I know. Some of them like to cover it up with a lot of Axe body spray, but it doesn't do the trick.

Seth: At least they're sort of trying, right? Better than just totally forgetting about it. So this is kind of going back to the earlier interview that we did with you and your sister, Mary. But just to recap, you and Mary are kind of built as opposites in a lot of ways, right? How does that evolve, or does that change at all with you moving to the U.S.? Or is it kind of just working the same way it was before? You're just on the same time zone now.

Ann: Yeah, I think our roles will definitely stay the same, because they really suit our personalities. And now our expertise is in that direction. So even this week, she tried to ask me to make a call that I really wouldn't normally make. And she said, "And you can do this." And I was like, "I know I can, but you're the pro. I'll just stay right over here, because I actually can't." I mean, I can't. I had to call a seller one time and I was sweating. Yeah. So we definitely have very clear roles. And also, there's a lot that she does that I don't even know what it is. She takes care of everything with the bookkeepers. She takes care of so many things. And I literally just write them off, because I know I can count on her. And she's the same with me. Or she'll say like, "Oh, I just drew on the map, but I'm just not even going to show you." And I was like, "Yeah, don't show me."

Seth: It's interesting how you don't like to play it safe in life. But when it comes to making calls, you do like to play it safe. You're kind of not comfortable with that, right? Am I hearing you right?

Ann: Yeah, I'm not comfortable. There's very clear things I'm not comfortable with. Calling sellers, any kind of drama or acting—icebreaker-type things in a group setting, I don't want to do that. Or when I worked at the bank, they wanted me to help people and tell them to think about it…

Seth: I hate that kind of stuff. That's the worst.

Ann: I'm kidding.

Seth: Yeah, I think the worst thing about that is, it just feels phony. Like, I'm sitting here trying to pretend like you need something when I don't care about it. And you shouldn't care about it either. But I'm being told I have to be this puppet and make you think something's important. I can't stand that stuff. It's the worst. In terms of like, you don't want to call people because it's not your lane, not your area of expertise or whatever—did you have a bad experience with that at one point? Why don't you want to push yourself in that way, but you do want to push yourself when it comes to moving across the world and changing your profession and all this stuff?

Ann: There must just be something in me. I also can't fire people. I don't know. It feels like a conflict situation, or it just makes me really… I can't even talk right now. I mean, literally anything like any kind of role play—I don't want to do that. And I just, I don't know. I can't tell you why. I just know I really don't want to do it.

Seth: You're speaking my language. I mean, I'm the exact same way. I'm not saying this like talking down to you. I 100% get what you're saying. But what else are you saying? You don't like to do things that are boring. You want to keep pushing yourself. But it sounds like maybe you've carved out certain places or certain areas where you do want to push yourself, in other ways where it's like, "No, I'm kind of just good here. I know what I do and don't want to do, and that's that."

Ann: Yeah, it's funny you say that, because in our family, one of our jokes is like, we always say, "Oh, I can put that on the list of things I'll never do." There's just certain things, you know, and you're like, "It's not because you couldn't do it, it's just I never have to choose that. That's something I'm just never going to do." And so I would say that calling a seller, I would like to put that on my list.

Seth: There is a lot of value in knowing who you are. I think a lot of people, myself included—I didn't really figure out who I was until I was about 30. That was when things started to click and I became much more confident and like, "No, that's not my preferred future, and this over here is." You know, something at this point in your life, you just know who you are. Right? And that's a good thing.

Ann: Yeah, that's true. I turned 50 this year, and it makes you, I mean, there's like all these clichés, right? And there's all the things that people say. But you definitely do start to think about, "Okay, what do I choose now? I've got this time left. Hopefully it's a decent amount of time. I'm going to keep myself healthy and I'm going to continue to grow. But now I kind of want to be in the driver's seat, and I want to let go of the stuff that I don't choose." So it's my stage of life.

Seth: So thinking specifically about the land business, as we all know, it's changed in many different ways. It's gotten more challenging in different ways. Have you found it to have gotten more challenging? Does the business feel harder to you right now compared to 12 months ago or 24 months ago?

Ann: Yeah, I think it is. I think there's definitely—in a lot of ways, there was a rush of people who wanted to jump on board and make some quick money, right? They had gotten some coaching or done some things that made them think that they could just jump in and wholesale or do whatever. And that made the water kind of muddy for a while, and it felt crowded and a little bit chaotic. Luckily, I think some of those voices have drifted away. Thank God. And then for the rest of us, the people who are solid operators and have built up a reputation, or are really knowledgeable in their market—as long as we are continuing to work really hard and willing to pivot a little bit, it is harder, but we can do it. But yeah, we're working harder. We're considering every single deal really carefully.

Seth: Did I hear right that there are certain types of deals you don't do anymore? Like, you're being more selective about what you're trying to go after? And if so, how so? What kinds of deals would you not do today that you would have done 12 or 24 months ago?

Ann: Well, we haven't done a straight flip in three or four years.

Seth: None? Not a single one?

Ann: Not a single one. Well, kind of. There was one we bought because we were planning on splitting it, and then we ended up not being able to split it. And that one actually—it was a terrible deal, because the numbers worked when we were splitting it. That was our deal. So I guess not voluntarily, but we did do one. And we ended up getting two septic sites on it, two build sites, and then we sold it as a family compound. So we made the most of it, and it still wasn't really a straight flip. But it's not something we're particularly interested in. I think it's easier for us to understand, like, our value is in our value-adds. And we know what the market wants, and we know how to bring it, and we're willing to do the work, and we're not in a hurry. If it takes us a couple of months to get it done, we're okay with it. So that's where we're happiest. And now that the brokers know that too, and our friends in mom's places know that, then those are the deals that people bring us as well. Yeah, that's our niche. That's our wheelhouse. It's definitely subdivides.

Seth: Any other types of value-adds besides just subdivides?

Ann: We have done some land and home recently.

Seth: Oh, cool. How did that go?

Ann: I don't know yet. We'll see. The first one was so clunky, just super clunky. This one that we're doing now most recently, it's going easier because we have the right… it's just in a community where we have the right team. The other spot, we're not as connected. So for us to get the people to work with us and call us back seems like a lot of juice for the squeeze, personally.

Seth: Yeah, totally.

Ann: I'm not willing to give up on it, but we're not good at it yet. And I'm not sure it's where we want to go.

Seth: I don't know from experience yet, but it seems like the kind of thing where it's pretty darn helpful to either be within driving distance of it, or have a very good trusted person there to manage the whole thing. Is that what you have in your situation?

Ann: We do have someone local that is able to partner and be the face as needed. But I think the one that's going smoothly—it's because our broker's dad is the GC. So that's going to work out okay. And that can be repeatable.

Seth: And actually, I just thought of a question I meant to ask you a while back. So if you're not doing texting or cold calling or direct mail, how are you finding all your deals?

Ann: Mostly incoming referrals from our agents and brokers, and then our new friends.

Seth: The fellas?

Ann: They reach out. A lot of times our agents and brokers, they'll have a deal—like the one that we bought this week. She sold it to a woman. It was a cockfighting farm.

Seth: Interesting.

Ann: Awesome. Actually, it still looks like that online. I'll send you the link. And it scared me when I looked at it. I was like, "What is that?" And I had to ask ChatGPT, "What are all of these little huts?" And then it's like, "Oh, those are typically used for cockfighting." And then I assumed that's exactly what they were used for.

Seth: Is there like a filter in the land portal? Can I look specifically for cockfighting farms?

Ann: I don't know. I wouldn't mind filtering them out.

Seth: I'm suggesting that they come up with a redneck filter as well, because that would be super useful in this business.

Ann: I would turn that one on, personally. Okay, so I want to tell you about this cockfighting farm. So this lady bought it. It's a very cute, long tract along the land, and along the back is a creek and then a big hill in the back. So it's so cute, so beautiful. She got it all cleaned up. She got rid of all of those little cockfighting coops and mowed it, seeded it, brought in a septic tank. She brought in a well too. I don't know why, because it has all the bladder, but whatever.

Got all settled in, had just started her build, and then her daughter called from Florida and said, "Can you move down to live with me and the kids?" Well, grandmas have to do that. So she just was like, "Chop it and run." She called the broker and said, "I know I just bought it. I just got it all cleaned up. I'm ready to sell it." And then this is a person we've done a lot of deals with. And she called us right away and said, "Girls, you want this one?" And we said, "Yep." And we bought it within 24 hours. So we get those kinds of deals a decent amount. The other deal that was bad, that ended up being a family compound—the buyer's agent is a guy that we work with a lot as well. And he just said, "I'm happy to bring you your buyer. I'm looking for our next deal." So he's like, already today, he just sent us a few that said, "What about this? What about this?" So I think now we'll probably partner with him as well on a couple. And then another big deal was a broker who had a buyer and they fell through. And then he said, "Can you guys pay cash and close quickly?" And we said yes. And then he became our landman. So I think now that they know that we're ready to pull the trigger if the deal is good, and they've worked with us before, then they know the deals we like, and they give us a buzz.

Seth: When you're making offers to people, are you offering it at a discount, or just buying it at full market value, or what's your strategy with that?

Ann: It depends. So the one that was this week that we just purchased—we asked her, "What does she need to get back to feel okay with the deal? Like, what did she have in it? What did she buy it for, and improve it with?" Because we knew that we are going to split it and it will become a few lots. So she told us the number and it penciled, so we paid it. It kind of goes back to that whole, "I don't want to sell you an extra pair of socks. I don't want to upsell you on anything." Like, we really just want to pay fair value for what our plans are. And if it works for everybody, it works for us. So that's probably also why we don't want to do flips—because we can't get good deals to do flips. So we can pay close to market value, knowing what we're going to do with it, and end up all right.

Seth: So do you not do flips because it's too hard to find those deals, or is it too boring, or is there not enough money on the table? Because as I hear what you're saying about how you find your deals, and how you don't really pay discounted prices or anything like that, and you're always doing value-adds—your business model is very different from what a typical land flipper is. You're almost not really following it at all, other than the fact that you're dealing with land. That's kind of like the main common thread. And I have heard many people saying, not that land flips are impossible, but it's just harder. You need to have a value-add strategy at least as part of what you're doing to make this a full-time viable thing. Would you agree with that? Or why is it that flips—you've almost kind of intentionally said, "No, we're not doing that"?

Ann: Yeah, I think mostly—and maybe it's that stage-of-life thing as well. When we started this business, we thought about, "What do we want? What's our goal? Why are we doing it? What do we want our day to look like?" And the way that the lifestyle business works for us is, I don't want to be going through data and sending out mailers and having four VAs. I just wouldn't choose that. So would I do it? Yes. Would I do it if I had to hustle or make it work? Sure. If I don't have to, I don't really want to. I would rather chomp off a big deal and then work our way through it over a few months. And that's worked for us. And I hope it can continue to work, because it feels really good as well. Once we know that the numbers work and we can underwrite it, and we can find the capital, then it means that our days are kind of quiet, right? You don't have a lot of responsive business. You have the window of time when you work.

Seth: No, that totally makes sense.

Ann: I think—I don't think Mary would say that. But from my end, I feel like I can kind of control when I work, and I like it that way.

Seth: Yeah, well, that helps, because you can certainly find big deals that you chomp off and work on with direct mail too, or whatever else, and possibly even better deals. But I think I understand what you're getting at. In terms of, without a lot of this responsive marketing and constant incoming phone calls and talking to people that don't actually want to sell—just like that's enough to burn anybody out if they don't have a good way to deal with that. It's kind of a luxury to just not deal with that—just intentionally say, "No, I'm going to do this other thing where I can control my day a lot better." Totally get that.

Ann: Yeah, I mean, fingers crossed that that holds, but that's the goal.

Seth: So with these subdivide projects, since that's kind of your bread and butter, are there any areas or parts of that where people underestimate the complexity or the cost? What is the hardest part about running that kind of business where that's what you're doing? Or is it not really hard because you have it down to a science?

Ann: I think if it's a minor subdivide, as much as it can be a science, we've pretty much gotten it down. I mean, every piece of land is like a fingerprint. It all has its own quirks and none of them are the same. But at least if it's in the counties we're familiar with, and the topography we're familiar with, and the soils we're familiar with, and the team that can go visit it really quickly—that part is okay. We feel pretty comfortable. Things get hairy once it's in a major subdivide. We have a deal right now that is a really big one, and there's a lot of unknowns and a lot of things we can't control. So I guess that's the difference. In a minor subdivide, yes, you have to find out the answer, but you can, right? You can take action and find it out. But for a lot of—once the counties are involved, or in this case, the cities involved, you lose a lot of that control, and it becomes just a completely different scenario.

Seth: Well, you've mentioned relationships being really important here. Clearly, since that's where all your deals are coming from, I'm wondering, which relationships matter the most, and why? Like, if somebody is hearing about your business and the way that you do things—you don't have to deal with direct mail or any of that stuff—if you were starting this over in a new market, totally fresh off the street, what would be the most important relationships that you would focus on building?

Ann: I have two answers. This week, the most important relationships that we had were our title agents, because someone was unsure about the validity of the deal and the offer. And so as soon as we could say, "Call Suzanne, call Teresa," and actually our dirt-work guy, "Call those three and they can all say"—and so we knew as soon as that could happen that that seller would be put at ease that, "Oh, okay, these ladies are not a scam. They've done it before. They have the money. They do what they say. They close the deals. They don't back out." So this week, it was our title ladies and our dirt-work guy. But overall, I think the relationships that we have that are the most important are agents and our brokers. They're out and about all the time, and one of them is hunting all the time, and he's got his dog out. So he's happy to walk properties—not hunt on them, we don't hunt without permission—but he's happy to walk them and talk to people. And they hear of deals, or deals fall through. So I think building up those relationships has actually been the most important.

Seth: How difficult is it to build up these new relationships? Like, if your task was to go out and develop 10 of these new relationships this week, can you just call them and introduce yourself and, "Hey, there's a relationship"? Or is the relationship measured by, "No, we've actually done a deal with them, they performed well, boom, now we have a valuable relationship"?

Ann: I think the good news is you don't need that many, and the bad news is that it takes patience and time, at least for us, the way that we've done things. I think there are four, maybe five people that we really lean on, and we've treated them right. And when we're there in the summer, we visit them and we go to dinner, and we know about their kids, and we send gifts. And we just kind of laugh and banter. We have a really fun relationship. And so that's taken time. But I wouldn't say we even need more. I'm happy with what we have. So I guess it's like any relationship—it takes time. It's a slow burn.

Seth: I mean, do you measure a good relationship by, "They do good work and we really like them"? Or is it more just, "They do good work, we don't have to like them at all, as long as they get the job done"?

Ann: Actually, I think it says on our website, "If we wouldn't take you out on the boat, we don't want to do business with you." It's just because I feel like it's still a business that we choose. So we choose how we want our day to look, and we choose who we want to do business with. And if somebody is a jerk, we don't really want to. We had to sell land to a jerk this year, and I still regret it. So yeah, I really just like doing good work with good people.

Seth: Yeah, I mean, I don't disagree with you at all. But I'm trying to evaluate myself even, and understand, like, why does it matter that I like them? If the objective is to just get the job done and make money, then that's that, right? But it's like—no, I think it kind of went back to what you said. If this is a lifestyle business where I do it because I choose to, not because I have to, that's a very important distinction. That's what differentiates this from being a business that you love running versus a job that you hate doing—is when you have the freedom to choose the people you work with.

Ann: And you know, I think you're probably right. I think you probably could do a deal with someone you didn't like, if it's transactional, right? And you know it's just one deal, and the numbers work and you can get through it, it's fine. But yeah, we have one note deal as well with someone that we don't really like, but he does have his automated payments set up and now we don't really talk to him, so it's fine. But at the same time, like, even that—I think it's nice if it feels comfortable and fun and you don't dread talking to them and you can trust them. I mean, we're humans.

Seth: So you had sent me a couple pages from—I don't know if it was your journal or what it was—but you're kind of explaining your situation. I think you mentioned the phrase "cash cliff." What does that mean in your situation right now?

Ann: Well, we've had a really comfortable and dependable salary and insurance, and everything paid—travel, house, everything. And now in a month, it's zero. So that's a cash cliff. I mean, that's just—you have to figure out pretty much everything. So not only that, but we were renting out our house and now we're moving into our house. So the rental, that monthly rental payment is gone. Luckily, the mortgage is paid off in like a month. But Wisconsin taxes still make you feel like you're paying it anyway.

Seth: Do you think this kind of transition would have been easier if you were in your twenties? Like, is there something about being in your forties, fifties that just makes it harder, because you've just learned how to live life a certain way and it's hard to uproot and change that?

Ann: I think for a normal person, I would say yes. I think for us, we would say no. Actually, the girls said it really well. They're like, "I can be in the bush in Ghana and I can be in a five-star hotel. Like, give me the situation and I can navigate it." And when they were saying that in the car, I was like, "You know what? Awesome. That is such an important skill." And we do kind of have that as a family. We know how to go to the bathroom in any kind of toilet. We know how to make a meal out of any kind of, like, corner container shop. We've had to kind of figure things out along the way just through our life experiences, and it makes it kind of interesting. I mean, my—sorry, Mary, she'll listen to this—but whenever I call Mary, my girls will say, "Oh, is she at Costco or Target?" And then I'll call Mary and she'll be like, "No, I'm at Sam's." So it's like, I kind of think we'll be okay. We'll have to be okay. We'll make it okay. And then if we have to move, we'll move. Because that's the cool thing about life: if you've built something, your skill set goes with you. So once you're a teacher, or once you're a land investor, once you're an adult that knows how to take care of yourself and work hard, no one can take that from you. So you can figure out a way to make it work. And like Hayden said, when she graduates, if she's in too much debt, she'll just live in a low-cost-of-living country. And I was like, "Yeah, of course." But then I was also thinking, I don't know that a lot of 18-year-olds say that.

Seth: We'll figure it out. Yeah. So I think you're spot on that it's a great life skill to have this mindset of like, "Give me any situation and I'll figure it out." I guess I still have a similar mindset of like, "I can get along with anybody. Give me any person, stick me in a room with them, like I'll find a way to make it work." Even if it's challenging, I can mold myself to be who I need to be in that situation with that person. And I think part of it is the skill of being able to do that. But the other huge part of it is just the attitude and the mindset of like, "I'll do what I have to do." Not just being like a stick in the mud, like, "No, I'm not going to change. You got to change for me. The world has to bend to my desires." It's like, "No, no, I have the energy and the willpower to do whatever I have to do to make this work." That's probably like 80% of the battle right there—just the willingness to do what you've got to do.

Ann: Yeah, it is. And I think it's something that—maybe this might also be—I wonder if I'm starting to say things old people say, like, "Kids these days, they're just really comfortable, right?" So maybe it's about—you just want to be comfortable all the time. And I wouldn't say that being comfortable all the time is our goal at all. We like to work really hard, and we're people who figure it out and make it happen, or do what it takes.

Seth: With this cash cliff situation, is it like you've got a certain amount of money in the bank, and when it's gone, it's gone? Or is that what you mean by cash cliff?

Ann: Cash cliff—just that our income is going to zero.

Seth: Income from the teaching stuff.

Ann: Right. We've been overseas for a long time. And like I said before, we've been really frugal. So we have a good amount of savings and some good investments, and now in the last months, some good land deals. And so I know we've got a decent runway and we'll be okay. But the immediacy of the zero—zero income and zero rental income—and then two kids going to college, out of state. It's a lot.

Seth: Yeah. Do you find that the land business controls your moods ever? Like, when things are going well, you just feel better about life. You can show up more for your family. You can just be in a better place in your head. And when there's been a dry spell, like things aren't going well, you feel sort of short-tempered, things just kind of get under your skin easier. Do you get that, or is that just me that gets that?

Ann: Yes, I get that. I get that. I'm not sure if it's land again or my time. Yeah, I wish that I had more control and I could compartmentalize things a little bit better. But yeah, I even find—this is terrible—but at recess today, I got a text that I was really happy about, and it was regarding a deal. And then I was more responsive and happier with my students because I'd had like a dopamine hit, right? But there's times too, like, that month ago when I was just really thinking, "Oh my God, am I a land investor? Did I wear this out? Now I'm leaving, and the whole country's in the toilet, and everything's terrible. And I'm just going to leave everything I've built to do something I'm not even good at." And so that—I mean, I think everyone has that self-talk, like, "You're not good at this. What are you thinking?" And then you just go for a walk. And then when you go for a walk, you either listen to great music or you listen to a very inspiring podcaster, and then you get the heck out of it. Don't sit in that space for very long, because it just zaps your energy and it affects the people you live with.

Seth: That identity thing is a tricky thing to figure out. Just what you said there: "Am I even good at it? Am I a land investor?" And I think a lot of people could probably relate to this right now, as the land business has gotten more challenging. Because even if there was a time when you could have said, "Yes, I'm good at this" in 2023, when everything is working and working fine, but all of a sudden the world is kind of different. So it's like, "Well, maybe I'm not good anymore. So maybe all that great experience is irrelevant now, and it's worth nothing, because look where I am now, and it's hard now." It's just this weird mental game to figure out—do I have a right to feel confident in myself or not?

Ann: Absolutely. And I think the other side of that is—and you're really good about this—staying on top of all of the trends, right? So you're on top of the AI thing and you're embracing it, and supporting Callan's workshops and all of that. And I can feel that extra layer of like, "You're not even doing the AI thing, and you've never texted anyone." Like, "Okay." I mean, it's maybe—but guess what else? I wear short socks and you can see my ankles.

Seth: So I get this a lot. It's part of why I hate going on Facebook. I have to, because there's a lot of stuff that happens there—at least that's what I tell myself. But every time I'm there, I'm scrolling through this feed and it's a mixture of people either yelling at me that I need to do something different, or trying to one-up me, make me think that their life is better than mine and they have it all figured out. And it's just this mixture of things that are not good for my mental health. I just need to spend as little time there as possible, which is this constant conflict in my head because of how my business works. But when you're fighting against that all day long, if you're somebody who participates in social media, it doesn't help you try to feel better about yourself.

Ann: It's true. Again, go for a walk, go to the gym. I know, it's just—it's all poison. It really is.

Seth: So, Ann, you've lived all over the world. What do you think people in the U.S. get wrong about money, work, and risk? Anything come to mind? The different cultures you've been exposed to—you seem to have a pretty well-rounded, culturally intelligent view of the world just with what you've been exposed to. Is there anything that you're not a big fan of in terms of the U.S. mentality about business or life or anything?

Ann: Well, I think people in the U.S. work really, really hard and really long, and they have to. And they have to commute, and they have to make it work, and they have to make dinner, and they have to take care of the kids, and they have to drive the kids all over the place. And I think it pulls families apart. So that stands out to me. I mean, even just—anytime that I'm talking with any family who lives in America, there's some kind of a struggle of, you know, schlepping kids around and holding the house up. And usually that's with one parent working. Do I think America has it wrong? I think parents are doing what they have to, but I do think it's not great. And I'm very thankful. Like, the thing that we believe is, we sit down as a family at dinner, and we eat dinner Monday through Thursday night at the table, and we say what we're grateful for, and we say the best part of our day. And it doesn't matter how busy you are, you come down to the table.

And so I feel very lucky and I have a lot of gratitude that we get to do that. I don't think that that would be possible in the States. In terms of mindset, you can tell a new expat or a new immigrant from America if they haven't lived overseas before, because they just keep comparing it to America. And they are upset because they can't get, like, real Kraft macaroni and cheese or something. And you're just like, "Get me away from this person." So I don't like trying to pretend I'm so worldly. I love it when I get to go to Chili's at the airport and all of that, just like everybody else. But I do think that sometimes Americans have a feeling that their way or their brand—or even medical treatments—are the best. And then I think we've seen that there's some really cool things happening other places. Being more open-minded as an American, especially when you travel, and realizing that you're a guest in the place that you are, is important. And maybe don't talk so loud. And I guess that's probably what stands out.

Seth: Yeah, I remember when I was in Italy back in late 2024, we were doing a mastermind group, Dave Denniston and I. I remember seeing this lady, obvious American lady. She was in line for something and trying to get answers from somebody. And then she looked at her husband and she's like, "They don't speak English here." I'm just like, "What did you expect? You're not in America." Just this idea that you really think the whole world needs to act the way that you do—it's a very telling moment.

Ann: My husband and I just had a really funny thing at the mall. There's a lot of foreigners—this is a pretty international neighborhood—but you can tell that this guy just got here, because we were on the escalator and he was at the bottom, and he saw us coming, and he like just watched us come down, and he's like, "Where are y'all from?" And we're just like, "Oh my God, this is just white guy saying hi." Because he's like, "I'm a white guy. Let's just talk American for a minute." And we're like, "This is so weird." Because actually, most of the people who live here have lived here for a while. We're not in a tourist area. But I was just thinking, "Oh my God, he must have been in the country just a couple of days or something. And he was excited to get his American hello."

Seth: Yeah, that's funny. When you think about this transition you're going through right now, yourself and your family and your husband—what are you really trying to build here?

Ann: Well, I am trying to build a life that is fulfilling, where we can be together as a family, and it isn't really geography-dependent. I think we've already kind of done that already. We know that home is where we're together. I'm trying to build a life for my kids of entrepreneurship, and I can see it's happening, which is very exciting. I was wondering what they were going to do in university, and I see them both going into this, taking this path, which is great because we come from a long line of teachers and professors and employees. Nobody's in entrepreneurship in our whole town, much less in our family. So I guess building that—like a mindset, and a legacy, and just a change. And I think also just a valuable next chapter for Mark and me. We've been in school together our whole life. We have the same birthday. I didn't mention that. I married my—same day, same year.

Seth: Same day?

Ann: Really?

Seth: That's crazy. What are the chances of that?

Ann: It's really kind of weird. It's very strange. But that said, like, it means that we were in school together, preschool all the way through 12th grade, all the way through university. Then we're teachers together. Then we teach in all the schools together, and our kids go to all the schools where we are. So like, our whole life has been in school together. So I think we're trying to build a life where we don't have to eat in a cantina.

Seth: If you were to open a time capsule a few years from now, what do you hope it says about this moment right now?

Ann: Oh, great question. Yeah, we learned about time capsules from our kids, because they like to hide them around the house and find them later. And they write little notes to themselves like, "Dear 17-year-old self." And so we've kind of started doing that as well. And now is a time where I am looking ahead and thinking, "What the heck is going to happen?" When I discover it, I hope that I am continuing in the land business. I hope that I've learned some Spanish—Spanish is new for me, I've studied Chinese all these years, so now to switch to Spanish is very exciting—so I hope I stick with it, self-learn Spanish. And that our family is healthy. And that we're making good choices, and helping other people, and staying connected, and just doing what we're supposed to do on the planet.

Seth: So if somebody is listening to this right now and maybe they're standing on their own brink, or facing a cash cliff, or going through a major life transition—what would you tell them based on what you're going through right now?

Ann: I think, be a decision maker, and don't let life just happen to you. Take control, zoom out, think about what you really care about, what you believe, what you want your day and your life to be about, and what you value, and then make a choice. And if it's wrong, then change it. It's not going to be the end of the world. You can mess up, and then you can pivot and change direction, and it's worth it.

Seth: Yeah. When there's a hard life choice to be made like that, how do you make that decision? Is it based on what sounds more adventurous, or what is going to potentially harm me the least? What filter does it go through for you to say, "Okay, let's try this first"?

Ann: I mean, I think at this point, if it's on the list, it's because we've chosen it to make the cut. But I think it's like, what is so exciting, right? Like, what is going to make me just excited to get out of bed? And where do I think I can fit? That's the other thing—living in other countries, you do want to feel like you've made a home for yourself, and that you have a community, and that you bring value, and you can engage. So yeah, I would choose the place that I think, "Okay, I love it, I'm excited. Even if it's going to be hard, or I don't fit in yet, I'm going to find—I'm going to figure out a way to grow there and connect with people"—and then go that way. Is it going to harm me? I don't ever think about that, probably.

Seth: Yeah, actually, I got that from one of my college professors who was talking about who he was going to vote for. And he's like, "Both options are terrible. I'm just voting for whoever I think is going to harm me the least." Has there ever been a time when you regretted taking the exciting path? Or has it just always gone well?

Ann: I want to be able to think of a time that I regretted it. But I can't. I literally can't think of one. I think maybe the only thing that I regretted is maybe staying teaching here so long. At some point, I thought, "You know what, I need to jump sooner." And I chose the safe way, and it felt suffocating.

Seth: If you chose the bigger adventure and regretted that, it sounds like that might be a different thing than the teaching path, right?

Ann: I think the answer is no. Every adventure has been absolutely worth it. Absolutely. And even if we say—you know, which people sometimes say, "Which country do you prefer? What was your favorite country?"—we can't choose one. Because you can't discount the learning that happened there, or the memories that are there. So when we're going through our life right now—we're getting rid of all of our belongings, literally everything that we've accumulated in these 25, 26, 27 years—and it's really not sad, because it's like, "Thank you, table. You've served your purpose. Back into the world. It's okay." So I think it's just the journey, and I don't regret any of it.

Seth: Well, that's really cool. I mean, I think that says a lot about your mindset and just your attitude. Because I think—just because you've never, quote-unquote, regretted the decision does not mean there hasn't been a time when you've chosen the exciting path and there were difficult times there. It doesn't mean it was all easy. It's just that you're choosing to look at it as though, "Wow, we learned a lot from this," instead of, "Gosh, that was terrible, I wish I hadn't done that." So that's all how you look at it, right?

Ann: Yeah, it is how you look at it. And I think there's always a way to have a good day. So make it happen. At least a moment. At least a moment.

Seth: Well, Ann, it's great talking to you again. Thanks for coming on the show, sharing your story, and where you're at and where you're headed. If people want to reach out to you—say if there's a 20-year-old guy listening to this who wants to throw all of his deals at you because he has no money—how would they get a hold of you?

Ann: Yeah, I like that. We are on Facebook, and our name is Mary Ann Danielson. We just operate as one identity, because we kind of are. We're just like a two-headed land investor. So she's all day in America, and I'm all night. Yeah, if we reply by phone, obviously that's Mary. And if we reply by computer, then it's Ann.

Seth: Awesome. Great. Well, thanks again. Thanks to all the listeners for hanging out with us. If people want to check out the show notes for this episode, it's REtipster.com/274. Thank you again for listening, and we'll talk to you next time.