Serious News

Chris Duff

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Cockroach Mode: Surviving the Worst Market in a Generation | Ep 301

In this episode, the current market environment gets a sober, unfiltered assessment as geopolitical uncertainty, AI-driven job disruption, and stalled real estate deal flow create what some of the most well-financed institutional voices are calling the worst market they have ever seen. Overhead has been cut despite having more personal liquidity than ever, and deal volume is down significantly from just months prior. The strategic posture is deliberate cockroach mode: not paralysis, but disciplined risk-off positioning while staying in action.

Key Takeaways:

  • Liquidity Does Not Equal Safety Having strong cash reserves does not justify holding overhead built for a higher-revenue environment, because idle capital still loses to inflation and opportunity cost.
  • Risk-Off Is the Harder Discipline Switching risk back on is easy; the real skill is staying genuinely risk-off when every entrepreneurial instinct pushes toward deployment.
  • Cockroach Mode Is Not the Bench Pulling back on overhead and deal pace is not an excuse to stop taking action, because continued movement generates data and separates operators from those who are fully paralyzed.
  • Belief as a Practical Tool Holding a strong conviction that difficulty is the price of operating in a historically unprecedented technological moment reframes uncertainty as obligation rather than obstacle.

Listen to the full episode for the unfiltered breakdown of how capital is being protected and positioned heading into what may be one of the roughest real estate cycles in the last century.

(Podcast transcript below)

Welcome to Get Serious. We’re at Serious Land Capital. We have successfully funded over $6 million worth of land deals with industry leading 41 % operating margins. So today, I wanted to provide more of a sobering assessment in relation to some of the just rampant excitement that I’d shared more on the AI side and especially the

you know, explosive capabilities of Claude cowork and just being able to lever effectively these harnesses on the, you know, highest quality AI models to, you know, really start to automate work and really cut down on workflows and, you know, total time invested for, you know, so many aspects of the business and to where,

Like it’s such a strange dichotomy right now where, know, I think historically, I know like almost any human being, you know, would just say, yeah, like the present is just, you know, the most exciting time to be alive and so forth. And like probably more often than not, that’s going to be the case because of discontinued technological progress. But I think there’s, you know, just a, very, very strong argument to be made that, you know, right now.

is like we’re just positioned for.

one of the most, if not the most, radical changes in terms of just the potential for technological impact upon humanity and the potential growth and life change that we can collectively experience, largely driven through the impacts of AI and these just absolutely most, the cutting edge.

models here. So we have that in one corner. And then this is countered by, you know, one of the trickiest, you know, most uncertain market environments on both a macro and many micro levels. Two, that just makes it really hard to reconcile

how to move forward strategically and tactically with both of those in mind. know, again, inherently as an entrepreneur, futuristic optimist. So, you know, I’m going to be more in that camp of, you know, longer term, yeah, this impact of AI and the, you know, explosive growth that we’re experiencing as a, you know, or

potentially as a species here in real time is like going to be the more positive driver for economic impact. But there is just so much nonsense and again, uncertainty going on with the general markets, real estate or otherwise, that it makes it really, really difficult to act appropriately.

with, you regardless of what type of information that you have in front of you. And some people that, you know, I trust, you know, deeply and have, you know, some of the most inside info for so many, you know, economic lovers and positions that, you know, some of the most well-financed institutions in the world

You know how they’re thinking and operating like some of these folks are just saying, yeah, this is the worst market that they’ve ever experienced. They’ve ever seen. Um, you know, just, you know, the market writ large here, which, know, is, certainly a sobering reality here. And that like largely matches up with my own assessment of the data. You know, obviously I pay the most attention to from real estate metrics, which you get into in a minute here. Um, but also, you know, what’s going on.

Stock market wise, how concentrated we are within these AI bets, a lot of really rough statistics surrounding job creation, job loss, anticipated disruptions from AI, just the unaffordable housing market, impacts of war. I mean, this is very current events here and I don’t…

tend to be an expert in regard to that. like, again, just to speak to the uncertainty and as you know, we record this in mid March, who knows when this, you know, may resolve, but like this Iran war situation, it’s almost daily where like I’m having to come to, uh, you know, a determination, like, is this conflict escalating? Is it deescalating? Like it’s, it’s, uh, uh, so foggy.

in such a gray area to determine, what direction are we even going? That, that again, it can start becoming paralyzing as an investor and just a business owner to, to attempt to make any kind of sense of this data. And like really the primary framework I try to keep in mind for any type of info that I’m trying to synthesize is like, okay, is this going to make it more likely or less likely for, you know,

people to want to buy real estate over like the next three to 12 months or so. And, you know, at what type of price points. You know, that secondary part of the question is much harder to answer, you know, heavily local, but like directionally, we want to indicate like, people feeling more bullish or bearish? Accounting for all these, you know, economic inputs to

to consider energy markets and so forth. We’re going to naturally be more insulated in the US economy compared to so many other parts of the world, but it’s still a pretty integrated global economy at the moment. If some of these other continents just get wrecked from…

energy availability and so forth and lose access to some other manufacturing and all that. Like it becomes a mess very, very quickly when there’s already so much uncertainty and fragility across the system here. So like all of that is just a key backdrop to where, you know, us as a funder and, know, just real estate operator. it’s been really tough to find the right deals here. mean, our

our revenue projections for this year. mean, compared to the last couple, I get it’s just really not even close. Like the funds are just not flowing as routinely as they had been. know, we’re fortunate because we have the backdrop that, you know, we’re more liquid than we’ve ever been. And like, personally, I’ve probably never had this much liquidity in my life, but it’s still

You know, so uncertain and difficult to operate here that like you can’t rest on your laurels or just like sit around holding cash, um, for a long period of time either. Cause I mean, you’re effective. Like if you’re holding on to cash, you’re, you’re, you’re losing money, you know, by, uh, uh, inflation, um, and, uh, at minimum, let alone, you know, opportunity cost for, you know, even lower risk.

investments. So, you know, I know a lot of people within the industry have talked about, you know, these

you know, there are just some structurally.

different mechanisms that we have to consider for how to build and run a land business in our current and future environment here. And like, we’re going through the same thing. And my partner and I like, you know, even as well positioned as we are and like, and we, you know, full optimist, know, entrepreneur till my very last dollar till the day I die is the approach here.

what’s it gonna take for us to get through this cycle and come out stronger than ever before? Like if I was gonna bet on anybody to do that, like I’d bet on us. I mean, that’s kind of the mentality you have to have as a business owner if you’re be in the game here. But it’s like, even if currently we’re well positioned here, like what do we still need to do to set ourselves up?

to potentially get through again, like one of the roughest markets ever, or at least in the last century and not blow ourselves up in the process. like part of that is just, again, relentlessly looking at overhead. I mean, we’ve had to make some really tough cuts recently where, yeah, ostensibly, like we could run our overhead month over month, potentially for years.

and still be fine, but it’s not smart decision-making when you have to account for, the opportunity cost of that capital sitting in these accounts compared to other more favorable investments that it could be in. That always has to be the objective approach for how you look for any type of capital deployments and utilization.

And so, you know, if we’re not doing as many deals, like overhead just naturally can’t be as high. So what do we need to cut? that made sense when we had a lot more revenue and profits flowing, like even a matter of months ago, compared to now where, we’re just being even safer and we’re trying to work through such, you know, again, a tricky, tricky environment and like not pull any riskier.

levers financially. I part like even considering, you know, potential leverage, you know, can be a massive, massive boon used properly and utilizing debt. But can also be, you know, something that blows you up in my partner’s like, yeah, there there’s like, virtually no scenario to think about even using leverage in a in a market like this and like,

I trust him from a structural perspective, more so than effectively anybody. And he’s seen so many just blown up situations and businesses that were very, profitable. then just, again, just blew themselves up by just not managing overhead and just having improper structures within their business. So like, we did have to be mindful of all of that.

Again, what does it take to be successful in potentially the worst market that we’ve ever encountered? Or at least professionally, mid-30s recording this and during the global financial crisis, 08, 09, I was still in college during that. And we kind of heard talk on what was going on and…

a family was in a bit more fortunate situation or it like, yeah, you got to tighten belts, but like, it didn’t like materially affect, you know, I dated a decision-making or, um, you know, I didn’t have the responsibility of running a business and so forth and supporting a family and all that. Like it was just a completely different scenario because you weren’t actually tested in, um, uh, uh, a situation like that. Um,

And so, you know, now we’re actually pressed up against the wall to, okay, you’re, you’re facing, um, just, know, incredibly difficult market. What do you have to do to actually succeed and get to the other side? And like, to me, you know, uh, no matter, like all that matters is the longterm here. And so long as you have cash and you have the ability to continue, like, I could care less on really how we get there.

You don’t want to sacrifice like your morals or ethics and so forth, right? Like stuff that can put you in jail or blow up your reputation. those are effectively never events in my opinion, like the Nassim Taleb, like what does it take to hit ruin? Yeah. Go to jail or destroy your reputation or die. So those are kind of the main pieces to avoid.

Anything short of that, like what does it take to continue along? And like, if I have to be a cockroach, you know, our business has to be a cockroach for a while. like there’s absolutely no shame in that. I, it’s so, you know, it’s hard to make some of those decisions, even from like an overhead perspective and so forth or slow, you know, be, being act slower, in regard to, you know, deals and so forth. And you might’ve been accustomed to.

But like compared to the alternative of like blowing yourself up and not giving yourself a chance to continue, like it’s the easiest decision in the world. And again, people would like, if they saw the amount of liquidity that we had and runway that we could work with and also like the relatively lower overhead that we would have and like what…

What world are you complaining about this from or like, why are you making these decisions or, so forth. But again, we’re just, we’re always trying to stay ahead of the curve and where the puck is going. So that it gives us the ability to, you know, adapt and still succeed in, potentially more, more pain to come, which is where we’re betting on again, it’s so easy to switch risk back on.

It’s way, way harder to be risk off. like that’s just inherently more difficult for pretty much every entrepreneur, to, properly be risk off. or, know, even if you think you’re being risk off, but you’re actually like more risk on than, that, that, then you might anticipate. that that’s kind of the, key paradigm to, keep in mind here. and so, you know,

Like when I’m saying, you know, we’re being a, going into a cockroach mode, it’s not necessarily indicative of the underlying, finances that, that, that we have a little liquidity in the capital that we have available, but it’s more of a consideration of the underlying market mechanics, how the model is performing right now and how comfortable we are with deploying capital in such an uncertain environment.

So that is the key nuance distinction that I wanted to make here. And to put a bow on this, so I know that this one’s already going a bit long and I really wanted to get into some additional historical context on like, worst market ever, et cetera.

or some of the worst market conditions, like what’s the true historical precedent? A lot of people mentioned the GFC, the dotcom and so forth and how it applies to real estate. I’m going to save that for later because it’s really, really informative. We’ll probably do that next week. But suffice to say, there’s so many negative indicators on what’s going on right now. Everybody knows this.

uh, anecdotally or, you know, true hard data. Like it’s just, um, objectively a harder market, uh, across so many different reasons. Um, but you know, as far as continuing to find a path forward here, I, you know, I always return to, you know, okay, what, what’s your mindset here and what, what’s your belief cycle, um, to move forward. like, even if you, you’re operating in a cockroach mode,

you know, some people might like take that as an excuse. like just, you know, taking the foot off the gas pedal. not going to take any action, just like purely sitting on the sidelines, which I just disagree with. Like there there’s an inherent bias to want to do that, but like, you still have to do something. You still have to continue to take action, even in the face of such difficult circumstances or constraints on, on, your ability to.

act as broadly as you might like. But continued action taking still provides more insights and informs future actions that will continue to lead you past others who are just completely paralyzed. you have to keep that in mind. But then also from just the psychological perspective, which again, I don’t think it’s enough.

attention or it’s pushed more into the woo category. Again, to me, I’m like very anti woo, like I want, you know, real objective truths wherever possible. And so I really attribute a lot of these psychological frameworks in relation to actual behaviors and, you know, results that are created from those thought processes.

So like, always like to remind folks on that and how I utilize these frameworks myself, but, um, you know, I was listening to a podcast recently where, you know, they were kind of separating between factual frameworks, faith level frameworks, and just, you belief level. And so facts, you know, we’re just considering as we’re considering as like objective truths here, like a two plus two equals four, um, type of truth, you know, faith.

You’re going to believe in something regardless of any evidence provided to you And then belief almost sits in between the two where, you know, it’s effectively the strong, strong convictions weekly held theory and, you know, choosing to believe in, you know, a certain framework, a certain idea, certain thought process. But it continues to be informed by evidence that can,

change what you actually believe going forward. And so I thought that was very helpful to keep in mind, again, just boiling down some frameworks that we might have heard piecemeal here and there, that how useful it is, just like humans, are hardwired to have these beliefs and that…

because some folks just like, I can’t believe in anything short of evidence here. But on average, if you have an approach like that, it tends to lead to more negative outcomes, both longevity-wise and happiness and so forth and all the things we kind of care about as a species. Whereas, you

we can readily adapt certain beliefs and just utilize them as tools. And, you know, always inform ourselves later on if, you know, there’s any reason to not believe this thing further. And some of them can be so strange or, you know, people might think they’re foolhardy and they might only work for, you know, a certain person, but, you they might encourage the right behaviors that still lead to

you know, objectively positive results. And so I always like to really keep that in mind.

And we’re like ultimately settled out. It’s like, you know, we were now given these tools to almost give ourselves superpowers as a species, as a, you know,

you know, thinking people. But we were also given a set of circumstances that are some of the most collectively challenging that humanity has ever encountered in its entire history as well. And we are being asked to rise up to the challenge. Are we going to be able to, you know, take the potential golden age in our hands and all the…

you know, again, rapid technological progress that that is in our grasp right now and be able to lead ourselves through to a more positive future collectively as a species or are we going to go the other direction? You know, there have been examples on both sides throughout human history, which is, a whole other discussion here. So we are put

at this fulcrum, at this critical point here, how are we going to contribute? It was too foolhardy to expect that things were going to be easy in order to like we’re handed these incredible gifts. Then what’s the phrasing of the person who is

You know, much was given, you know, much is expected. It’s effectively that like that. That’s the belief I choose to hold. so now that’s even more invigorating because it’s like, okay, you were given, you know, all the most, you know, the talents and knowledge and so forth. And you’ve, earned your right to be here as well, too. How are you going to lead yourself and your community and your family and, you know, audience and so forth through this, um, to contribute to humanity, getting past these uncertain times.

in order to flourish more long-term. Like it was always going to be hard. So do you have what it takes to play your role and show up every day to help us all collectively move forward? And so that’s the reframe, that’s the belief that I can maintain to adapt to this.

high level of uncertainty, high level of difficulty that we’re all dealing with in some capacity or others. So with that, we’ll wrap this one up here, kind of heavy topics. I’m sure it resonates with many of you, subscribe and share. Looking forward to next time. Take care everybody, bye.

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