Seth: Now you know how we feel listening to you, Drew.
Drew: I just can't fit into the fire! They're making super tiny tweaks, and it's boring, so it doesn't feel special.
Mike: But yeah, it kind of is, though — how much of it is our ADHD? We want that dopamine hit of trying something new. And in reality, the boring machines are what consistently work in most spheres of business — landscaping companies, plumbing companies. They're just doing a very boring skill set and making small improvements. I've had some conversations with friends who are making well over a million a year gross — they're doing pretty good, I'd say their net is at least half a million a year. And I see that today, while at the same time knowing a lot of people have quit, or are struggling to stay in the game. And when I talk to those people who are doing really well, it's like, "I hope you realize how special this is — don't take it for granted." And I don't think they do, but I also don't think they realize they're doing something right, and they should be really proud of that. It's that they're doing the little things right.
Drew: They're getting on the phone with leads within five minutes, or at least their team is. They're not changing their marketing strategy every three months. Imagine sending three mailers — 10K per mailer, let's say — and the first three just bomb. You have to be crazy to send that fourth one. You almost have to be stubborn enough to know it works in the long run and trust the law of large numbers — a big sample size.
Seth: That's tough. I don't know if I could do that — three campaigns, 10K each, all bomb, and then do a fourth one. I'd feel like I'd have to change something. But you're saying people just don't change anything and trust that with bigger numbers things will work out — is that always wise, do you think, or could that ever be insane?
Drew: Yeah, don't do that blindly — you're making tweaks. You have to almost have faith in the business model at a very high level and ignore the noise. Ignore the minute feedback you're getting, because it might not actually be useful. I think a struggle a lot of us have in this business — a lot of people got into it during COVID times, and life was so easy then. We were making deals hand over fist. If I was doing mail and changed to texting, I was still getting deals — I might have to make some tweaks, might slow down my deal flow, but 60 days later I have deals coming in. Now if you make those shifts, there's such a bigger lagging effect, which is harder for us — and then it makes you think, "Why is this?"
Seth: But you talked about feeling like we're now more in a pre-COVID time — like how it was back in the day. I'm curious what you think — when are we going to get back to that COVID time period, or what do you think the future holds in this space?
Drew: Hunkering down, tweaking your systems, really dialing in, and not jumping all around too much — which is so easy for us as entrepreneurs. We all have that shiny-object syndrome, it's probably why we got into this. When we lose 10K on a mailer, it's like, "Mail doesn't work, mail's dead." Texting, PPC — something's dead, I should be doing SMS, I should be doing subdivides. I'm not holding out hope for another COVID timeframe. That was such a weird, unique situation — the government injected so much money into the economy, interest rates were so low, it was a bizarre time that made it really easy and profitable. Maybe it'll happen, but I'm not thinking, "Hey, maybe next year." I don't expect that again.
Drew: I do expect another crash at some point, like 2009-ish — maybe not that hard, but something like that. I feel like that's coming, which is like the opposite of the COVID boom — things are terrible, but that presents its own opportunities too. I read last month or the month before we had the biggest surge in first-time homebuyers in like three or four years.
Seth: Oh really? Wow. That's great — why? Is that because prices are coming down?
Drew: I think prices are slightly coming down, but I think it's also that these people have just been waiting on interest rates to drop for so long. It's the American dream — own your home. And I think for a while it was like, "Why would you rent, you should buy," and then interest rates went way up, and it's like, "Why would you buy? Financially you're better off renting." I think we're slowly starting to see that shift again. But it also depends on demographic and market. I know people that do Airbnb arbitrage now and are crushing it, but I'd say probably 70–90% of the people doing Airbnb arbitrage got their butts handed to them when things went south.
Mike: But that's where consistency is key. It's hard to see, though — if I go to the gym and work out, a month or two from now I'll start to see a difference. If I send out mailers, I won't. If I send out 100,000 mailers I might do a deal — buy for 20, sell for 50. But if I sent out 101,000 mailers, I also might land a deal that's a buy for 20, sell for 200. It's so hard in this game because you have these inconsistencies, and we have these KPIs where we say, "I want to make 20K a month, 15K, whatever" — but when you actually look at it, one month you might make 50, 60, 80K, and then you might starve the next two or three months.
Seth: Yeah, for sure, especially as you're going after bigger deals.
Drew: I would say — to answer your original question on the future of the land business — I personally believe we don't care if land prices are going up or down. The only thing we care about is transaction volume. We just need sellers and buyers to make selling and buying decisions. Even in a depreciating market where you're buying slightly too high and your margins are getting squeezed — maybe we're in that time right now, maybe that was 2024 and 2025 — even during that time, to me that's okay, because your margins are getting squeezed on the way down, you're making smaller spreads, but once we hit that trough — and I think we're in it right now — it starts going up again, and we're going to see another expansion of your spreads, because you're buying in and then, while you're holding it and trying to sell it, the value is going up. If you see the land business as a sideways curve that moves through a range, the compressed spreads and the expanded spreads kind of equal out. All we really care about is transaction volume — we just want more people selling and more people buying, because we are technically middlemen. Realtors, title companies, mortgage brokers — anyone who serves a seller or buyer — we all are middlemen, and we just want people buying and selling. So where do I see transaction volume going? I have no idea. I do think if we had another 2008 it would be rough — very rough for about a year, because every piece of inventory you're holding, you're getting out at break-even or choosing to hold it for two or three years. But once you're done with that rough year, you're buying back in at such a low cost basis that if you can hang in there, the fishing gets really, really good once we're in a 2009–2011 kind of trough.
Drew: What I do know is what it felt like — and my bookkeeper, Steve Hokanson, kind of supports this based on what he's seeing — is that during COVID times, maybe the top 80% of land flippers were profitable. Now it's the top 40%. So we lost half. But anyone I see leaving the land business, it's very clear to me — it's not that they've been using the wrong mailer template, it's almost always a mindset issue. When they're leaving, if I know them well enough, I could almost have predicted it in hindsight — they just don't have the mindset of an entrepreneur. You need to be a little bit crazy, and a little bit stubborn, and you need to have that fire. You need to be calling these leads back immediately. If you're a solopreneur, you need to be — I used to answer my seller-lead calls live and get yelled at. I used to put my personal cell phone and home address on these mailers, because I wanted that edge, I wanted the "blue text." That was years ago. But you need that fire and hustle. I always go back to a donut shop — they're supposedly saturated, but there's one on every corner, selling white bread covered in sugar and low-quality coffee, and they're still in business. All they need to do is keep their floor swept, smile as you walk in, and say hello, and they're making a living. So I think the whole market-saturation concern isn't legitimate. There's always going to be people who want fast liquidity — I sold a $16,000 car for seven grand because I just didn't want it anymore, I wanted it gone. I've been in a position where I was happy to sell at a discount just to get the annoyance gone. There's always going to be that. So I don't see the land business going anywhere, and we are looking to do massive growth within Rooster Capital in the next 12 months.
Mike: I'm curious, actually, from both of you — how do you deal with mindset here? You talk about having to almost be crazy to be an entrepreneur, you have to have the right mindset, but when you keep getting kicked in the face again and again — especially after you were just thriving these past couple of years — and now the grooves in the space, the influencers, everything else, are even more well-known, more voiced right now, so I think it's easier to feel further behind at times. What's your trick to keep going? What am I supposed to do when I haven't had a sale in two months? I keep calling sellers, they keep saying no. Why am I even going to pick up the phone and call this next guy, he's just going to say no? Should I just shoot him a range offer, or not even bother, or ask a team member who's not a great acquisitions manager to give him a call?
Drew: Where does that come from, or what do you tell that person who's just struggling right now, saying, "This is silly, this was just drop shipping" — back in 2005, I don't know when drop shipping was popular — "maybe I should just go get a W-2 like the rest of the world"?
Mike: I actually kind of get annoyed with the "fix your mindset" answer a lot, because it feels like a catch-all. But the technicalities do matter — what you're doing does matter — but it does come back to mindset, and I think that's probably what you were alluding to.
Drew: That's why people get out of it. They got into it with a certain expectation that was true years ago, and it's not anymore — it's not as easy as it used to be — and they're like, "I'm out." It's the same reason divorces probably happen — ultimately because of missed expectations. Somebody expects something from the other person and they're not doing it anymore, so they check out. I think it was Shakespeare who said expectation is the root of all heartache. So check your expectations. I'm sure it probably differs depending on the land investor, but when you look at the cost of every lead who actually calls back — if somebody responds to your direct mail, it could be like a hundred bucks a person who's calling you back. So if you're paying that much for the privilege of somebody responding, are you really going to let that go, or are you going to seize that opportunity for everything it's worth? I had a guy yesterday call back, and it was funny — he was almost cussing out my voice AI agent, but when he heard it was a female voice he said, "I'm not going to say what I actually think." He was being polite to it. But I listened to the recording and thought, "I'm going to call this guy back," even though he's clearly saying no, no, no — why not call him back? I paid a bit of money for this. So when it gets harder, you start realizing maybe it is worth answering the call live if it's actually worth that much for every person calling — whereas when the deals came easier, it was much easier to just ignore people. Now it's like, no, I have to do what I've got to do to make this work.
Mike: I'm curious for you, Seth — you've been in the space for a long time. I'd say — and I might be a little biased because I'm a business partner of yours too — but I think you have the best podcast out there. You've been podcasting consistently for so long, and I'm sure you've seen seasons, as a podcaster, of more views and less views and everything in between. How do you keep going? Because I feel like it's very similar for us in this situation — your business might be a little different in the podcast world, but it still takes that consistency. How do you have it?
Seth: Yeah, we were talking about this yesterday. I'm an Enneagram type six, which is a loyalist. Most of my entrepreneurial friends are Enneagram type threes, the achiever — they're visionaries, great at starting new things, good leaders. I'm not really those things. I can do them when I have to, but it's not my forte. My forte is, when I figure out what I'm good at, I just put my head down and keep doing it. That's almost my happy place — when I've figured something out and I can just keep doing it, and it's really my happy place when it works. Part of why REtipster has lasted as long as it has is because I figured out it's something I like and I'm good at, and I just keep doing it. So as numbers dwindle, as people get out of the land business, as the internet changes — as lame as this sounds, it's what I know and I love it and I want to keep doing it. This idea of reinventing myself or starting something new — I can do it, and I have when I've had to, but it's not something I really enjoy, I don't find it exciting or fun. Whereas you guys, I think you kind of do find that exciting or fun. So maybe a screw is loose in my head, or my brain's just built a little different, but it's nothing heroic — it's just what I enjoy doing and want to keep doing as long as I can, and I'll change whatever I have to within the confines of being able to keep doing what I love. And if the day comes that I just can't do it, I'll figure something out.
Mike: What would have to be true for that day to come, where you can't do it — is there anything that would make you think, "Okay, this isn't working anymore"?
Seth: It kind of already has been happening over the past couple of years. It's not like the hammer comes down one day and everything has to change — it's more like, "Okay, I see things changing on the horizon, I should probably plan for this, figure out other things I can do, other ways I can contribute value." Which is part of why Stride exists — that's something I can still add value in. My self-storage business is another thing — part of it is an itch I've always wanted to scratch, a business I've wanted to get into, but it's also, "What if REtipster doesn't last forever, what if I get tired of it at some point?" I don't want to suddenly wake up and have to totally figure it all out in one day. So as the world starts changing, start diversifying a little — if you send your grain across the sea in five different ships and one of them doesn't come back, realize that's a possibility. Don't put all your eggs in one basket. That's kind of how I deal with it, and time will tell if that was smart or dumb. Actually, this past week, I posted a video about this idea of moving on from land — if you're good enough to succeed at land, you're probably good enough to succeed at a lot of other things, too. This idea of not being a one-trick pony — look at people like Arnold Schwarzenegger, Oprah Winfrey, Jessica Alba — they had massive success in one thing, but they didn't stop there. Arnold Schwarzenegger was a bodybuilder, then got into acting and was huge in that, then became the governor. Nobody would have faulted him if he'd just won Mr. Olympia seven times and said, "Yep, I'm good, I'm done, I'm going to retire" — people would see that as a smashing success. But he didn't stop there, he just kept going. I think it's similar for land investors.
Seth: Well, I guess it depends on the person — if you love land, if that's all you ever want to do, awesome, maybe you found your happy place, like I found mine. But don't be afraid to try other things, use land as the springboard to bring you to something better. You don't have to keep doing this forever.
Mike: But aren't we contradicting our own discussion from 20 minutes ago, where we said be consistent and don't deviate?
Seth: I think for a season, yeah — but you don't have to do the same thing forever.
Mike: One thing I struggle with is, how do you know the difference between shiny object and diversification? And the opportunity cost of split attention — you run a lot of things, but you have REtipster and Stride, you have your land business, a fully operating machine, plus Stride. Do you guys feel like that comes at a pretty significant cost to the other one? Because I had my own land business plus my funding business, and I chose one — because it was bugging me, I felt like I was a B-minus in both, and I wanted to be an A-plus in just one. Do you guys feel that, and how do you deal with it?
Drew: Yeah, I think there's absolutely a cost to it — I don't want to sugarcoat that. But there's also a cost to choosing one thing and then the world changes on you and that one thing is no longer relevant, or you don't have the skill set, or you're not willing to adapt your mindset to the new world. So there are risks both ways. I feel like there's ultimately less risk with diversification if you choose your things well and don't overcommit or spread yourself too thin. I think that's really the key. There's kind of a hierarchy of things — it depends on what's paying the bills at the end of the day, but the first rung everything has to pass is, do I enjoy this? If it's like pulling teeth, it doesn't belong on my priority list. Then, do I have some competence and value to offer here — or I shouldn't be doing it. And then it's got to actually pay the bills. My kids' podcast, Storyland, is massively popular but doesn't pay the bills, so that's way at the bottom of the list — if I've got too much going on, it's not going to happen, I'm not making episodes that month. It's supposed to be a life-giving creative outlet, that's for fun, but if it doesn't check every box it's not a priority. The self-storage business I set up in such a way that it requires very little of my time, so luckily that's not a huge time suck.
Drew: To answer your original question — I feel like, as an entrepreneur, to make yourself bulletproof you need to be okay going back to zero once you stop expecting this up-and-to-the-right trajectory, and you're emotionally okay with starting over if whatever you're doing doesn't work and everything crashes and burns. If you're emotionally okay starting over, and you believe in yourself that, hey, I can open a donut shop if I want and be just fine — once I made that decision, I'm okay starting over, I just ignore all the noise, ignore a lot of the little waves that hit the ship.
Mike: I don't know — that could also be the ostrich method, just burying your head in the sand. It's hard to know the difference.
Drew: I think what it comes down to — it's interesting, because you're talking about diversifying, and Charlie Munger has a famous quote: put all your eggs in one basket and watch it very closely. For anyone listening who doesn't know, Charlie Munger was Warren Buffett's partner in everything they did. Unfortunately he passed away last year — he was in his 90s, multi-billionaire, great guy, best friends with Warren Buffett, just kept a little quieter than Warren but was so fascinating. I was talking to Josiah Ronco, a good mutual friend of ours, about a year, year and a half ago, about the land business, and he asked, "Are you worried it's getting too saturated, too many operators in the space?" It's interesting because now operators are leaving and we're like, "Huh, there's not enough land deals" — before we were like, "There's too much competition here." There's always something to complain about.
Drew: And I told him, what I think is great about what we do is we're learning business fundamentals — how to do things — so we can start from zero. Storyland is crushing it right now on the podcast charts. If you'd tried to start Storyland when you started REtipster, I don't think either one would have been successful, both would have been such a struggle. If you'd asked me three or four years ago to start Stride Rescue, both my land business and Stride would fail miserably. My land business is pretty well functioning now, and I'm fortunate enough to have hired a COO, Julian, who's phenomenal and runs that day to day, so now I probably spend 80% of my time on the Stride side of things, and that's nice. I don't think you can chase the shiny object when you're still building the first one — I think you have to do the ostrich technique to begin with. And I hope, as that grows and you get better at business and life in general — this is probably a horrible example, but like driving: when you first learn to drive there's so much to focus on, and now you see people driving while texting, changing the station, talking to their friends, putting on makeup — you just get somewhere without even knowing how you got there.
Mike: That's a great analogy, I never thought about that. It's so true — there are so many things we do in life that we just get very good at over time, so it's not taking your focus anymore, because it's natural. Yesterday I said something to you and you said, "Don't Chris Bosh me" — and why did you say it? I'm like, "Would it be crazy if we went here?" and I didn't even notice I said it. It's such a habit for me to talk that way now — before I'd have to focus on it to get better at it. So as you stay consistent, you get better at these things, and then over time you can start venturing into other things. But if you do it all at once, it's going to fail.
Drew: That's very encouraging, because I feel like in any business model — 60% of it, I just made up that percentage, but 60% is entrepreneurial general skills, the other 40% is niche-specific knowledge. So guys who come into land from other business models — Clay's a great example — pick it up very fast, in six months they're off to the races, versus for me, land was my first entrepreneurial endeavor, so it took a year or two. If you're listening to this or watching this and it just feels hard, know that you're learning transferable skill sets for the rest of your life — negotiation, leadership, accounting, how to handle massive risk.
Drew: Mike, I know you're on the market currently for a spouse, so if you're listening to this and you know someone... but at least for Seth and I, and I know you've dated before — a lot of times, at least for me, I feel like my spouse cannot relate to my stress, and I also don't want to tell her, I don't want her to have to bear that burden that's mine. Entrepreneurship is often a very, very lonely road — and that's in any field, not just land. If you're learning how to deal with that now, hopefully in a healthy way — through sauna, prayer, getting enough sleep, exercise — that's going to transfer to other niches wherever you're at in 20 years, which is encouraging.
Mike: Yeah, you know that loneliness thing? I don't know if this totally fixes it, but it really does help to have other friends in the business — especially when it's kind of a market thing, like it's not just me doing dumb stuff, it's my business, but external factors are affecting all of us. It's like therapy to be able to call someone and say, "Dude, this is just not going well," and just being real about it. Inevitably that person will respond, "Yeah, no, I know what you're talking about, things aren't going well for me either," and even if they don't, they can at least empathize with you and say, "I've been there, I totally get it." It's like medicine for the soul. If you're working alone in the land business and you truly don't have friends in this, you should come to an event, or connect in our Facebook, or reach out to somebody and become friends, because it's hugely helpful.
Drew: A couple things there too — I'd say a big advantage I've been fortunate enough to have is having friends who are entrepreneurs in different spaces as well. That's nice because, A, you learn different ways of doing things that other people in our space may not be doing at all. And B, if you're an entrepreneur, your world is different — you eat last, you're the last one to get paid, and everything else. I was talking to my best friend Roland — he owns a cybersecurity company, that's what he does, he's an entrepreneur, went out on his own a few years ago — and we were working out together, complaining about life in general, running businesses, everything going on. We'd had a couple issues recently with Stride and some staffing things, and I was complaining to him about that. Then he's telling me about one of his clients — a warehouse where about 200 people work — and the internet stopped working there, there was a Cloudflare outage, and things had to get fixed on the back end. He's telling me, "Yeah, 200 people are at this office and they cannot work, and my client's losing revenue every second — they drove there, that's just a regular Monday, and they can't work." He's on a call with one of his vendors, and someone from Cloudflare, and there's a director of ops, a director of this, a director of that, and he's talking to all these high-up employees, but he's also been telling them how to fix the issue too — and it's like, no, they're the creators of this product, he shouldn't have to be doing this. And they're like, "Well, we should first restart it, there's going to be 45 minutes of downtime," and he's like, "Okay, before we do that, why don't we try fixing this first, and then restart it?" And they're like, "Our procedure is just to restart it first." He's like, "Okay, would it be crazy to do this?"
Mike: Just like him — hearing his "Chris Bosh" thing, he did another Chris Bosh thing, yeah.
Drew: You're right, and I'm sure he actually didn't say it that way either — he just said, "Why don't we do it this way?" Anyway, he's doing that, and here I am thinking, "I'm agitated because, unfortunately, we had a staff member leave us — she got an amazing opportunity, and we're so happy and blessed for her, it's phenomenal, she's moving into a great part of her life — but then finding that replacement, I'm complaining about this." And here he is complaining that his client has 200 employees who can't be working. It kind of shows you it's not that big of a deal — a lot of these things can easily feel like the sky is falling. A good friend of mine, Brian Lupin — shout out to him — runs a great small group called Action Academy, really for entrepreneurs. He talks about "dumpster fires" — there's going to be fires going on constantly, most fires are dumpster fires, they're going on outside, they're contained, and they really don't matter that much.
Drew: My business coach talks about this too — "new level, new devil." As you move up in business, in life, no matter where you're at, you have something else you're facing, something else you're struggling with. I hate to bring it to everyone listening, but you're always going to have struggles, whether this is your first time making $5,000 this month on a land deal, or you're making half a million dollars this month — there's struggles somewhere, because we get comfortable, and then whether it's income inflation or lifestyle inflation, you start spending more, or you have something going on in your personal life or business life — I think we always have issues, and it's just understanding that's okay. Put a smile on your face, because you're learning, and the next season of your life, when you have another issue, another struggle, it should be easier, ideally.
Mike: I think about the land space — I think I had a huge advantage because when I started five, six years ago, it wasn't super common for people to have VAs. I started with a smaller version of a standard guru program a lot of us went through, and a month in I had three VAs working for me. People were like, "How do you even find a VA?" It was unheard of back then — but the first time I hired a VA I was 19 years old, so I was used to it. And I think that's why it's so important to keep learning and making those small tweaks, because it's also too late when you finally hit the bottom of that curve — as it starts to go up, those who really tweaked those things and got good at this business will see a 4x, 8x, 10x return, and they're flying off. I talked to so many people four or five years ago who said, "I wish I would have tripled my mail back then," or their text, or anything else — and I wouldn't be surprised if we're saying that five years from now too, like, "Why did I play it safe?" It's been therapy for me — I told you guys this yesterday — I don't watch a lot of movies, but watching entrepreneurship-type movies, like the BlackBerry movie, or McDonald's, or Facebook, or The Big Short, and seeing their extreme frustration — you can relate to them, and they're doing it at a higher level, risking everything. In the BlackBerry movie, the outside business partner they bring in mortgages his house just to pay payroll — a reverse mortgage, I don't know how that works — and then you think, "Am I playing it too safe?" At least in America, what's really the worst-case scenario? Do you move in with your in-laws? You're still going to eat three meals a day, and you feel like a loser for two years.
Seth: Did that end up working out well for him — mortgaging his house to pay payroll? How did the story go?
Mike: So BlackBerry — I don't know, I was like, was that a swerve? But BlackBerry did this, right? It didn't have a fairytale ending, but just seeing their extreme frustration and the internal conflict between those founders, I think it's good for us to realize things are very, very messy, and that's okay.
Drew: We see these people on podcasts and everything looks polished. You do a good job of showing behind the curtain — hey, this is not polished, life is messy. But a lot of influencers in our space and other spaces make it look easy, and you doom-scroll and feel like you're behind on AI, and you should be doing this, and then you're getting marriage advice, and you should be doing that in your marriage, and you just feel constantly behind. In reality we all have pretty messy lives, and especially on social media you're only seeing the best 10% somebody presents to you, so you always feel behind, and that's not what reality is. That's why it's important to find a group, find a mastermind — doesn't have to be in the land space — find a group of guys and gals you can run with, and become this cohort of high performers where you're transacting, both in terms of deals and little emotional nuggets, for decades. That's the vision I have.
Mike: I prefer to find masterminds where everybody else in the group is behind me, so I can feel better by comparison — it's usually the healthiest setup for me.
Drew: For you that's easy.
Mike: You're right, you're right — I totally agree with you, Drew, I think just having a tribe is so important, and it's easy to get caught up in social media. I think it's easier now for us to isolate ourselves than ever before in history. And it's also, if we're feeling bad now, it's like, "Oh, I can go talk to my best friend Claude," you know, ChatGPT, and it's like — that's not the same. I'm fortunate too — like, my best friend, his wife, and some other friends of ours, every Saturday we'll get together in the morning and usually go on a five-mile walk, and we just chat and talk about life, and we'll be having a discussion very similar to what we're having now. It's weird, because now we're on camera recording a podcast, but honestly we've been having conversations like this the last 48 hours, and it's beautiful. It's just so great to get away — anybody listening, go outside right now, take your socks and shoes off, hopefully you're not listening to this in wintertime up north, and put your feet in the grass, and just realize the world is beautiful, life is beautiful, and how blessed are we to have these struggles.
Drew: Do you guys think AI has made the isolation problem worse? Maybe it depends on the person and how much they use it, but I feel like it's...
Mike: I don't know if I feel more isolated per se, but I can think of many times over the past year where I've had a question I would have asked a human, and now it's like, what's the point of doing that, AI knows better, I'll ask AI. So it makes me wonder — if that's happening with me, it must be happening with other people too.
Drew: Also, if you're a faith-based entrepreneur, the questions we used to pray about, now we just go to AI.
Seth: Interesting, I thought about that too — AI has become our God in a way, because if you're approaching God trying to find an answer, sometimes it takes a while, it just doesn't come through at all, versus AI, it tells you right away, and it's designed to make you happy.
Drew: Yeah, man, we are seeing a spike — a massive spike in in-person events, run clubs, hiking meetups — and people are craving that, because now I don't trust videos I see. I don't know if it's AI or not — I saw a bear holding an AR-15, and I know that's real, that's real, but then you see some cute girl walking on a hiking trail doing her talking-head stuff with her AirPods and the white cord, and, anyway, that could be AI, you don't know — there's no way to know. It's crazy, like, everybody listening to this right now thinks we're actually human beings — what if this was AI they're listening to?
Mike: No, no — yeah, and so it's true, people are trusting what they see on social media less and less, and they crave — we crave — human interaction, we need it, biologically we need it so much. So if you're running a business model right now and your SaaS moat is gone — well, build a moat with a community, where people are coming to your software to interact with each other. I believe human connection is the new moat, and if you can somehow weave that into your business model — for example, with Rooster Capital, we don't just fund deals, we host in-person events that are either free or super cheap, my operators come to my house, my wife cooks for them, and we hang out for a few days. It's invite only, but my operators love these events, because we get to connect face to face, and there's a community piece involved. The group chat stays active for months because these guys are connecting — I even had two operators start doing a self-storage deal together because they met at my event. So they're building friendships, and I think that's super important. At least for me, that's probably been the biggest reason for my own relative success in this niche — I show up to events and connect with people. I'll also mention retipsterinnercircle.com, if you're looking for more of a curated experience with me and Neil Clements, you can check that out too. But the point is, do something, connect with someone somehow, because it goes a long way.
Drew: I don't think anyone's really replaced that with AI or social media or whatever. What's funny is when I started the land business in 2020, we created our own little mastermind from our initial education cohort — we were in a course, and five of us got together and said, "Let's keep meeting." That's how my first one worked too — we met for five and a half years, then we just stopped meeting. My motivation, selfishly, for creating that group was because Buck Rizvi was in the group. At the time, in 2020, Buck was way ahead of me, and my thought was selfishly, "I'm going to get really close to Buck so that if I screw everything up, at least I can work for Buck." That was my motivation — at least Plan B, I'm somebody else's employee, and that's not the end of the world, we could move to a cheaper part of the country and live off a fraction of what a business owner makes. But for me at the time that was my psychological safety net, and we met for five and a half years, it was great — the group changes, people branch off and try different stuff, and out of the five of us, maybe two or three are still in land full-time. Find a group, guys. Find a way to connect with people, and if you don't have one, create one.
Seth: So we were talking yesterday — would you rather be super successful, with all the money you need, and bored? Or struggling financially and stressed, but excited and reinventing yourself? What were your answers to those questions?
Drew: I think life is all about the pursuit. There's some saying — when you listen to music you don't just hear the cymbals crash at the end, that's not the point of it, otherwise all songs would be a second long. It's going through the journey, which I think is what's great, and also what sucks — like climbing a mountain sucks, it's hard, and there are times you're thinking, "Why did I do this, I just want to go back to base camp, I want to quit." But then once you hit the top, you see the view, and it's like, "This is amazing." But then it's also important to realize there are other views in the world too.
Mike: I'd rather struggle. I think money's meaningless without a reason to wake up in the morning. I went through a season in 2024 where everything was easy — I didn't really have an incentive to grow Rooster Capital, I had two or three operators doing 100-something deals a year together, and I hit this funk where I was making good money and thought, "What's the point of life?" Life got easy. I'm in a grind season now, so I don't feel that currently, but I've had the opportunity to taste what it's like to be the bored, rich guy, and I can tell you from personal experience it's way more fun to be the scrappy guy with no backup plan, because I miss those days. I had a W-2, I was a company commander in the Army Reserve, and I was running my land business — I had two and a half full-time jobs, basically. I miss those days of being on seller-lead calls at 11 p.m., I miss the scrappy days where there was so much uncertainty, and I'd much rather be stressed than bored.
Drew: Who talked about this extensively yesterday — the only experience I've ever had with what I thought was depression is when things were going really well and the business was easy. I wouldn't even call it boredom, but when there's not this drive, this urgency to get to the next level, we're just coasting — I don't think we were meant for that, we were meant to build something, not just rest on our laurels. That's not to say I enjoy being stressed and struggling, but there's something kind of sweet about the pursuit — being in the fight, not in the stands.
Mike: The gladiator metaphor isn't the best, because they were slaves, but being in the arena fighting is much more fun than being in the stands not experiencing it. The thing that confuses me — I don't know how you guys feel about this — if you asked me what my goal is, I'd tell you, get to X amount of revenue and profit, have this lifestyle, get this thing. But if I got there and didn't have a plan for what's next, I'd get into a weird, depressed funk again. So it's like, is my goal to get into a weird, depressed funk? It's weird — if I actually got there, everything becomes meaningless.
Drew: But I don't want to continuously struggle either. Maybe the objective is to always have the next goal in mind — figure out, when you get there, what's next. Don't just have a finish line where you're done. I totally agree with you. The caveat I'd put on this for everyone out there, my personal thought — it doesn't have to be financial. As entrepreneurs, and as Americans, it's very much that capitalist mentality, go out, hustle, earn money — but there's nothing wrong with becoming a great cook, nothing wrong with building a treehouse for your kids. There are so many beautiful things out there. We talked about this a bit yesterday — I almost feel like other countries do better than America in terms of happiness, because here it's like you almost always feel behind, whereas in these other countries, they'll take a two-hour lunch break, go to someone's house for lunch even while working their regular W-2, have a home-cooked meal together, build that rapport, that brotherhood, in a social way — where we isolate ourselves. And also, you're never going to hit the top of the mountain, no matter what — it's always higher. I don't think any of us — I sure hope you do, Seth, especially with Stride — but I don't think any of us are beating Elon Musk anytime soon, or Jeff Bezos, or Zuckerberg, the titans of the world. But it's also important to stop and smell the roses, enjoy the joy of life.
Drew: I know — we were talking to Ajay recently, and he said the problems you're having now are a blessing you prayed for years ago. How blessed are you to have these problems now? We were talking the other day — when you're in your early 20s it's like, I could just make 100K a year, I'd be so happy, I'd be set. But as you move up, the goalpost keeps moving. There's nothing wrong with sitting off the field for a minute to watch other people play, and enjoy where you've gotten to, and realize there's a lot more to life than just the grind and entrepreneurship — you can have the grind and also discover who you are as a human being, seeing the world.
Mike: We've talked about this a bit too — pain is pain no matter what you're going through, emotions are emotions. When you feel like you're struggling, this is the worst — but if you go to a third-world country and see people there, it's like, you've never really struggled. Have you been sleeping on the streets? Have you not known where your next meal is coming from? Have you been suppressed by a government? Have you truly been homeless? I think it's easy for us to play these head games with ourselves, especially because we see other people out there crushing it, so we think... but it's like, communicate with each other, create that brotherhood, that sisterhood, whatever you need — create your family, create your tribe, and enjoy the world, enjoy the earth, ride it, hike it, and build, because how fun is it, what a blessing is it, to have these stressors, these issues, to be in the pursuit. Don't let it get the better of you — realize life is still beautiful.
Seth: So true. If you have the opportunity just to be listening to this podcast, you're doing better than 99% of the world right now — you're not in a war, and hopefully you don't have a life-threatening disease you're fighting with right now. You have the luxury to take time out of your day to listen to this podcast. How many people don't?
Drew: Yeah, and that's a blessing, and I think it's easy for us to take that for granted, especially when we have a deal falling apart, a lawsuit threatening us, bankruptcy — so many different stressors constantly. But no, life is always stressful, you will always have stressors, no matter whether you're at the top, the bottom, or anywhere in between. So enjoy the ride — this is our shot — and if you don't have stressors, because I've been through seasons where there are none, it's actually worse, you get bored. So be grateful for your problems. I heard this thing the other day, from a book I'm reading — Warren Buffett's got all the money in the world, he's 94 years old, would you switch places with him right now?
Seth: No.
Mike: Yeah, I mean, nobody in their right mind would, because life's almost done. It's like, what's all the money in the world if you've got no time? So that should be very telling — if you're even remotely young, 50 or younger, 60 or younger — you've got time, you've got time wealth, and that can be worth a heck of a lot more than all the money in the world.
Drew: Yeah, so there's that to think about too.
Seth: Love it. You want to make some plugs?
Drew: Yeah, go ahead — what do you want to plug?
Seth: Yeah, really quick, Drew — if I have a $10 million deal, I can just bring it to you and you'll fund it, and I'll be good to go? Or what's going on with Rooster Capital 2.0 right now?
Drew: Right now we are focusing on funding land flips, let's say sub-$250K purchase price. Minor subdivides — if you have entitlement deals I'll look at them, I'll give you my two cents, though there's a low chance it'll work out, but I like underwriting them. Same thing with major subdivides as well.
Seth: I know you guys, I'd like to talk about some events coming up. Do you have a REtipster event coming up?
Seth: We do — it's sold out, though. But we have another one planned for April 2027, a ways out, but check it out at retipsterinnercircle.com if you want the list details.
Mike: Talk about Stride.
Seth: Yeah. So far, Seth — StrideCRM.co, best CRM of all time for land investors, seriously. It can do just about anything for probably a lower price than whatever you're currently using, if you're using anything else. There's tons of new developments happening all the time — we've got a new MCP API connection that's kind of mind-blowing. If you're using Claude Code or anything like that, you can basically access and do anything in your CRM without even logging in, you can connect it to other software. We've got a voice AI agent that can answer your phone calls for you, help with direct mail, project management. If you have any interest, check out stridecrm.co, shoot us an email at [email protected], happy to do a demo with you. Anything else we should mention about that?
Mike: We think it's a great product, there are real people behind it, and we're very fortunate we've been able to implement it with the changes in the world right now. We released mail not too long ago, so you can mail from the platform, do almost anything you want, and it's nice that it has that API connection, because as we get more and more into the AI age, most people want to automate things that we may have mild limitations on in the platform — you can now do a lot of that. I use it too, just to send this to my COO every morning — how many calls did my team make, how many appointments did they book, what's their conversion rate, what time did they make those calls, were they early or late for their scheduled appointments, what am I noticing, what are the pattern recognitions — these are all things Claude is doing now. It's like we almost have another employee tied into this.
Drew: Well, because it's weird too — I hear you talk about it, like you don't even have to log into the CRM, which is true, but you still need a CRM that will connect to the back end of your phone system to send contracts. I think it's great as you level up as an operator, with more team members — it's also easier to oversee them, and you could run almost everything through it if you wanted to. You'd still have to go to your phone or online to make phone calls with the contracts right now — actually, I guess you could automate the contract sending too.
Seth: And you use it for your own land business too, which I know has been really helpful for you as well.
Mike: Yeah, selfishly, I loved it — that's how Seth and I ended up creating this. I felt like there wasn't a phenomenal product out there just for the land niche. There are some good ones out there, but some weren't made directly for land investors — you end up using something like Salesforce, Follow Up Boss, Podio, that's not made for your niche. I feel like Stride is able to bypass almost any limitation you may be having. There are still some caveats, though — don't get me wrong, you should not be mass-SMSing in Stride, you could in theory, and we've had some people do it, but you'll probably get your phone number shut down, so keep that in mind — you'll still want to use a service for mass outbound texting.
Mike: On the texting and cold-calling front, StrideSkip is also worth checking out — strideskip.co, it's the cheapest skip tracing you'll find just about anywhere, and that's even if you're not using Stride. You don't have to be a Stride CRM user to use strideskip.co, but if you are, you get an additional 40% discount. So if skip tracing is something you have an ongoing need for, check that out too. And we have "Ask AI" in that platform now, so anytime you have any issues, ask AI — it's right there in the browser, ready to go, and it understands how your CRM is built, and if you make changes to your own CRM, it sees those changes. I think you made a video on this too, so check that out — askai.com/ret. I have no idea what the actual link is, that's Seth's department, but I'll throw a link in the show notes. But yeah, it's nice having that there — so now if you have an issue with your CRM you're not waiting on a support agent, or going to ChatGPT or Claude trying to explain the issue — here's an AI that understands how your system is built, and if you change your system you don't have to explain what workflows you've built or what's going on. This AI can understand a lot of that — it can find out where John Smith is in your system, when's the last time you talked to him, right away.
Seth: Go for it, Drew — all you, man.
Drew: Plugs for Rooster Capital — if you want to hang out with myself and Rooster Capital as a whole, you can go to roostercapital.land, that's where you'll submit deals. There's also an events button you can click — any event that's a Rooster Capital event is invite only, you can request to attend, mostly for operators doing deals currently with Rooster Capital or with intentions of doing a lot of volume with us. Also, I'll be at Ajay's event, Landscalingsummit.com — I'm sure we'll have promo codes, try Mike, Drew, or Seth as a promo code, I'll talk with Ajay after this and get some live promo codes going. Also, I'm co-hosting an event in Bali with Sumner Healy from LIA and Land Insights — the website for that is balilandmastermind.com, starting in late January, our second annual Bali Land Mastermind. Feel free to join us there as well.
Seth: Cool, sounds good to me. That's right, we'll be there — well, hopefully. I was planning to join last year too — he's had some issues with thunderstorms blocking his flights getting to Drew, so second time in a row we've had some flight complications due to thunderstorms with Mike's airplane. Prayers for his bad luck there.
Mike: You just gotta be consistent, keep trying, keep going — eventually we'll get together like we did here.
Seth: Oh, awesome, cool. Well, thanks everybody for joining us — thanks to Mike and Drew for coming out here, braving the weather, and making this happen. We will talk to you next time.
Mike/Drew: See you guys, see everyone.