Serious News

Chris Duff

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I Teach This Mistake to Avoid… Then Made It Myself with a $90K Property | Ep. 122

In this episode, the Tennessee $90K property revealed previous MLS listings at $200K (early 2023) dropping to $125K, then relisted at $125K (late 2023) dropping to $100K without selling—yet all four team members missed this during DD despite checking listing history being standard protocol. The property is now listed at $190K with zero buyer interest.

Key Takeaways:

  • Expired Listings Hide Without Street Addresses Vacant land parcels lacking assigned addresses won’t surface in standard Redfin/Zillow searches—requires Google searches combining acreage + street name variations.
  • Parent and Child Parcel Searches Both Required Must search total acreage AND individual parcel acreage separately with “0 [Street Name]” format to catch all possible listing permutations.
  • Four-Person DD Still Missed Critical Data Having multiple reviewers means nothing without systematic search protocols—this mistake proves team size doesn’t prevent failures without proper process.
  • Lemon Properties = Instant Pass Even in bull markets, previously listed properties that dropped 50%+ and still didn’t move should trigger automatic rejection regardless of current pricing.

Listen to the full episode for the raw emotion of discovering a massive rookie mistake and the systematic fix to prevent it from happening again.

(Podcast transcript below)

Hi, Chris over at Serious Land Capital Vacant Land Funding Partner. You guys are getting…

getting me kind of dealing with a huge, huge blunder on our part here. So you’re hearing as I’m immediately working through some of this and trying to solve how to prevent this scenario from happening again. You know, I promised when I started this podcast, I wasn’t going to have it be all

You know roses and sunshine If we mess up you are going to hear from that So hopefully you won’t ever make those mistakes either So I know I’ve remarked Oftentimes over the last month or so on Offloading some of our portfolio that has not been moving ASAP basically fire sale there’s

properties in Tennessee in particular that are keeping me up at night when I just commented on yesterday the smaller near Lakefront lot a little less expensive then there’s this other one that’s roughly 25 acres that we bought for 90,000 I thought probably flip-flopped on it 20 times on whether to purchase or not we’ve built in a lot of preferred

preferred returns on it before funding Because it was it was just a slow market we just we just were not positive and this was you know again purchase prior to Trade war tariff situation when there was still a bit of a bull bull market within the land industry and depending on the area And we just have not gotten any real traction on it

you know, well over and long with listing this one. And so I was exploring a whole bunch of scenarios, including pursuing a possible auction, which, we did, and that’s a whole nother process. I’ll go into the actual mechanics of that, later, but, part of that required getting our current listing terminated with the listing agent because, you know, an auction is just a separate process. can’t be marketed twice for regulatory reasons, whatever.

Fortunately our broker is very understanding. He’s like, yeah No worries, you know, I’ll you the termination If you guys get this sold like just send me whatever to like cover the expense I did to market it He’s not looking for extra commission or anything, which is obviously gonna be helpful so You know, we probably still have this one listed at roughly double what we purchased it however

And it’s three separate parcels. So we initially were marketing them as separate ones based on the recommendation from our realtor But then I was like, okay, let’s also just list, you know the full 25 acres Even though it’s split like two of the properties the smaller ones are across the road from the main 16 acres So it’s like, you know, it’s a full 25 acres, but it doesn’t really make sense as one property But figured okay. Let’s list that one separately as well

a slight discount compared to each individual property all put together that are listed separately But when I was checking out the listing today the 25 acre which has been listed now for about a couple weeks and I I was just blown away because we made one of the biggest rookie mistakes one that You guys hear me comment on all the time

about checking for previous listing history from a property that a seller is looking to move. And lo and behold, as my mouth just or, you know, chin just dropped to the floor, this 25 acre property was listed twice within the last couple of years. One for once in early 2023 for just under 200,000 dropped all the way to

think 125 K and then taken off the market after several months listed with another broker in late 2023 for 125 K and then reduced over a six month period down to just under 100 K and then that listing expired as well. so now we’re sitting here. Okay. Re listing the property.

you know, 190 when it was previously listed at just about a year ago for half of that and did not move. So this is like an obvious, obvious example where sellers sold us a lemon and we didn’t realize that. And, yeah, and this is typically, you know, one of the first things that we check. And you guys hear me comment on this all the time. You know, I have four people, including myself, to be checking.

previous listing history and it slipped by everybody. Not blaming anybody else. Ultimately, that’s my system I set up and the buck stops with me. If I make that mistake, you know, I have to own up to it. No way around it. And I’m racking my brain because I’m like, we always find these things. So how is this one missed? How do we prevent this situation from coming up in the future?

Because a lot of times with these vacant land parcels, you know, they don’t have an assigned street address and so For their various MLS listings illa redfin, whatever they might Be listed in a different way, you know, they might have like a zero thrown in front of a street name to be listed but not always and

you know, if it’s an expired listing, it’s not going to be showing up on, you know, for sale or pending or sold comps or anything like that. Otherwise we would have obviously seen that before purchasing. and so now I’m just trying to think, okay,

The way that we missed that is like, it’s almost like this previous listing history only appeared once we bought the property and are now listing it again. So how do we figure out how to get that listing history that’s not necessarily obviously showing up when we’re diligencing a property to come up? And so we’re gonna have to experiment, but the…

To me, the way to be most conservative with it is take the actual acreage or like all the different types of acreage. So this was like three different properties. So I would be taking the parent parcel, all the acreage put together, and then each of the individual properties. And then I would just be plugging in the street that the property is on. And in this particular case, even though it’s on one street, they have different, it’s a different street name depending on what side of the street that you’re on. It’s really weird.

So I would be taking each of those streets and putting the acreage next to it and then searching that within Google or maybe perplexity. It probably doesn’t matter seeing if it returns anything that leads to a previously active listing and then also throwing a zero in front of the street name to give it an assigned street address and see if we can figure out.

anything. I think that would be conservative enough to find a previous listing.

to prevent this from happening again. Because again, this is land investing 101. This is something you should be learning the first week. here, I’ve been doing this for years now and I just, again, you’re hearing this live, I figured this out half an hour ago and I’m still just, I’m incensed. I’m incensed at myself that I cannot believe.

that we made such a critical, critical mistake in this economy to be buying a lemon property for 90 grand too. That’s going to be a nasty hit. Our auctioneer thinks, and that’s the thing, sometimes properties that don’t move on market can have much better success in an auction format. Properties that were sitting for months on market can move at a premium on auction.

The guy I’m working with comes very highly recommended, referred over, has worked in that area a lot, he’s viewed the property, has had a lot of success with his auctions, he thinks he can get us a reserve price for at least getting our purchase price back net of expenses, which would be incredible. That would be honestly a miracle in this situation. Otherwise, I’m not sure what type of loss.

we might have to eat on this. fact that we basically bought this at the price where it was not moving on market previously, it’s…

I’m so disappointed. I’m so so disappointed So, you know just want to give that to you live here So, you know, sometimes you got to feel the emotion and like feel that loss like I just I cannot stand losing like that It’s just it kills me. It absolutely kills me And then you know just trying to work through okay it happened This is the situation speed of recovery. We’re talk about what are the next steps to prevent this and how am I gonna solve?

immediate fire of getting this property off our books for At least what the money we put in or mitigating loss as much as possible here so Don’t get caught in a situation like this you’re hearing it from me And it’s something I again remarked on Tons of times to other land investors something I teach and here I go

making a mistake like that.

I will let you guys know how we sort this one out. It is obviously top of mind with that. Looking for funding, serious land, dot capital, land, daily diligence, Facebook group for zero cost view of your land deals and landpricer.ai. At least I can feel better about that. I huge progress done on that earlier today when I was hitting kind of a block.

with some of the AI elements. you know what? Stay focused on the long-term, what you can control and take wins where you can, because not every day is gonna be a great one when you’re a business owner. And this has been a mixed bag, mostly negative right now. With that, subscribe and share. I hope you guys appreciate the candor and hearing.

from me real and raw at the moment. Talk to you next time. Bye.

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