Anthony WeilerI teach people how to flip vacant land in rural America for an average profit of $25k-$50k per deal

Why Land Investors Lose Deals (The Follow Up Problem)

12 Dec 2025 · 2 min

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1:45

In this discussion, the speakers dissect why many land investors lose deals, pinpointing ineffective follow‑up habits as the core issue. They explain that sellers often request a future callback (e.g., in two weeks or two months), but land investors typically wait the full period, allowing competitors to move faster. The recommended strategy is to halve the seller’s requested callback window—calling back in half the time they suggest—to stay ahead. The conversation contrasts land investors, who are described as “lazy” in follow‑ups, with house investors, who are portrayed as aggressively persistent. To operationalize the aggressive follow‑up, they advise using any tracking system—CRMs, Monday.com, or even simple Excel sheets—to schedule reminders for calls or texts, ensuring consistent, proactive outreach. By adopting a “savage” follow‑up mindset, land investors can convert interest into signed agreements before competitors intervene.

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I completely agree. And I would love for you to kind of unpack that a little bit because when people hear like, oh, it's in the follow-up, like, oh, I called him yesterday and then that's it though. Like they call him once and that's done. Help people understand what you mean by following up effectively or being a savage with follow-ups.
So every seller, like not every seller is going to be like, hey, let me sign something right today for you. I'm going to sell it at 50 cents on the dollar or whatever it might be. So things come up where they're like, hey, I'm definitely interested in selling, but maybe not right at this moment. Okay, so then we've got to put up a follow-up in our system that says, hey, if they say call back in 2 months, that means I'm calling back in a month. So I cut it in half. Like, I don't go on what they say. Hey, call back in 2 weeks. I'm probably going to call back in a week, to be honest. Like, so I want to be ahead of everyone else out there. And most land investors compared to house. House people are crazy. Like, their follow-ups are nuts. Land people are very lazy. I'm just going to be honest with you. It's like, talk— because I know probably 100 land investors I've worked with. I mean, probably 70 to 80. Obviously, Anthony probably can attest to this too. Like, we get it kind of easy because land's a lot easier. They're like, just like, hey, we got a deal. Now let's send out a signed agreement and they're going to sign it. Like, so we get kind of lackadaisical, if you will. So following up is just like, hey, they might not be ready right now. So you've got to set up, hey, I'm going to call them, whatever CRM you're using, Anthony's, just even in monday.com, or even if you're using Excel spreadsheets, like you've got to have something saying, hey, on this day, I've got to reach back out to that person or send them a text.