This episode documents a costly delegation mistake in LandPricer.AI development where prematurely ending the scripting agency retainer before full audit completion revealed major logic flow errors requiring 3-5 hours of manual rework. The lesson contrasts successful VA delegation with proper feedback loops for deal diligence against hasty software project management decisions driven by budget pressure and timeline urgency.
Key Takeaways:
- Delegation Requires Continuous Feedback Loops Successful VA deal diligence delegation involves recorded Loom reviews of every property analysis, creating systematic improvement through hundreds of reps with constant quality verification.
- Premature Agency Termination Creates Low-Value Manual Work Ending scripting retainer before complete video recording audit exposed missing numeric logic flow for comp assessment, forcing founder-level attention on tedious data entry instead of high-leverage activities.
- Budget Pressure Accelerates Poor Decisions Over-budget project status combined with reduced perceived utility triggered hasty retainer termination, illustrating how financial stress compounds into operational mistakes requiring greater time investment than originally saved.
Get the complete analysis of effective delegation systems, software project management pitfalls, and how to structure auditing processes before cutting contractor relationships.
(Podcast transcript below)
Hi, Chris Duff here at Serious Land Capital, vacant land funding partner. So today, going over just a key issue where I, again, absolutely shot myself in the foot. And I’ve remarked on some of these negative issues even over the past week. It’s just daily lessons of running your own business and
trying to be as efficient as possible when growing. So something that I think everybody has to find the right balance in is being able to delegate versus abdicate. I know that’s been a common phrase and remarked upon by many different entrepreneurs, but just to share a little bit more tactical example related to our business.
First, we have gotten a lot better at delegation over the last two and a half years, especially. So we have one core VA who works internally at our serious land capital business. And I’ve been able to, over the past several months, delegate a lot more of the initial diligence of funding deals for him to
review and it makes it much more efficient when I can go in, check his work and see all kind of the relevant comps. But because ultimately I’m going to need to sign off on it and if it’s high dollar value, then my partners are going to need to sign off. Plus we have a third party due diligence expert that we bring into. So we have multiple different levels of approval for
various deals that we fund, but that initial piece is usually done by my VA to kind of sort out what might be most useful related to the property and kind of key questions and setting up some of the copy to send back via email for every particular land deal. Nevertheless, all of those, some of them are very easy to review.
Frankly, they might just be terrible properties and, you know, it’s kind of clear issues or they’re active lots and, you know, just obviously wrong in terms of value. So things like those I can spend a couple of minutes on and, you know, just have my VA follow up accordingly. But the vast majority I’ll then be doing another pass and setting up a separate loom.
to review those properties as well as, any that we review on the land daily diligence Facebook group. I’m having him watch those because it’s also reviewing the work that he did to prep more efficient processes while I’m on the, live diligence session. So that is our internal review mechanism and has helped him get a lot better over the months. Just rep after rep after rep.
Um, that allowed me to become, uh, the key, key expert within our business and handing over a lot of that initial look for him to get better. Um, yeah, just like any other skill, you just have to spend hours and hours and hours to get good at it, especially complicated, um, tasks like reviewing and trying to value any piece of land in the U S. Uh, so
That part we’ve been better at in terms of delegating and constantly reviewing work because then they’re just a good feedback loop within that. It was a little trickier for the land price for software. So I had hired an agency who were the scripting engineers for the software and really the backend.
of what the software looks like is, you know, since we’re trying to price any, any parcel in the U S and we have to work through this full logic flow of various questions, a lot of branch, branching logic. and as you can imagine, when you’re trying to price any type of property, there’s, you know, several different directions, almost infinite different directions that, the questions can flow through in order to arrive at the appropriate price.
When I was initially trying to just run that process myself, uh, about a year ago, um, I was just getting nowhere. It was just so busy anyway, like that, that task just kept getting pushed further and further behind. Yeah. Ultimately, you could say, Hey, you didn’t have the discipline wherewithal to stick with it. And yes, that’s true. Um, but you know, it’s also a lesson in the who, not how mentality of like, okay, well, I can set the direction of what we’re looking to do with the script and then get.
these engineers to follow my pathway and line of thinking to actually draft out the relevant copy and the exact, you know, numeric logic flow for all these questions. And ultimately, yeah, I was willing to throw, you know, a few, you know, tens of thousands of dollars to get that done. Otherwise, it just was never going to get done. So, you know,
Trading time for money usually is a bad trade unless you literally have no money. So that is the ultimate decision that we made for that piece. And admittedly there were a lot of kind of growing pains, both issues on my side, just being a bit inexperienced from a software project management role. And initially we didn’t have the best middle manager.
and direct liaison for the scripting management team and we had to get them shifted around to somebody who was more apt to work directly with me and that helped loosen things up a lot more. But as the script engineering requirements for the product diminished, especially over the last four weeks or so, and a lot more of the focus came back to the…
true front and back end coding for the actual software product. I was spending less time auditing and reviewing the work of the script engineers and ultimately a few things slipped. I would do a lot of looms and review here and there and continue to improve the process. But because
I’ve already been over budget on the project. I, initially had a deadline with their agency for my current retainer arrangement with them to end tomorrow. But, ultimately, I retroactively decided, Hey, let’s end it as of last Friday instead. Cause I just didn’t seem to have any further utility for them. at least in the immediate term.
But we could still have an ongoing arrangement for separate hourly smaller scope of work type projects that might still be related to the land price here. But as I’ve been going through the process of recording all the various videos to augment the direction for
the actual software. Ultimately, I’m figuring out, oh yeah, there’s errors in some of the logic flow that this isn’t going to be as clear or useful for users. So it’s additional deeper level of analysis and auditing that I’m doing as I’m going through these videos. And then the last couple of days, I’ve found major, major errors with
whole pieces of logic flow that were associated with assessing subject properties that are supposed to be repeated for, sold and active and under contract comps, in order to accurately price the properties that were just completely missing. And it just requires a lot of manual work then to go back in because the numeric logic flow is just going to be separate. I know this might just sound like a lot of,
jumbled words at the moment. Suffice to say, there’s probably at least another three to five hours of just nasty manual work that needs to be done, where I already let go of the team that could have fixed this, that I more hastily decided on before I had fully audited the process. And ultimately that was me dropping the ball.
in delegating too liberally and not having as close of eyes on the process as I should have. I just rushed it and now I’m regretting it because ultimately that nasty manual work is just going to have to fall on me for the sake of just time and my own fault. I won’t make that mistake again, but I’m already under enough.
pressure to get this out that I just have to carve out. It’s not like that much, you know, extra work from a creativity standpoint. It’s just like, gosh, it’s just mistakes here and just inputting in cells, like really low value, low value work. But now I have to pay for it. And I just wanted to remark on that.
One example earlier on how we’re doing better at delegating and reinforcing a good feedback loop. Whereas today and yesterday, I’ve just been kicking myself, getting really frustrated in the morning, just realizing, oh man, I just added hours and hours more work that I thought was already done and now I need to fix it. So just keep that in mind for your own business. Always new frustrations, always new ways to learn.
But that’s where we’re at. So Sirius Land Capital, SiriusLand.Capital for any of your land funding needs. Check out landpricer.ai for this software that I’ve just been mentioning to accurately price any land in the U.S. And check out Land Daily Diligence Group on Facebook for zero cost review of any land deal, whether you are seeking funding or not. And lastly, again,
Check out Dave Denniston’s unconference, just Google it, it will show up. I think it’s the second link for the 2025 event in early August. You have to apply, you’ll get in so long as you’re making at least six figures, top line revenue for your land business. And assuming you are making that when it comes time for checkout, just use my name, all lowercase, Duff D-U-F-F.
in order to get $200 off your ticket. Again, this is the only large land conference I’m going to this year. Hope to see you there. Couldn’t recommend it highly enough. All my best. Bye.
