In this episode, a year-plus software development project hit a critical inflection point after beta testing revealed the product took 45-60 minutes per property review when the market demands 10 minutes or less, forcing a complete strategic pivot after $80K+ in engineering costs with potential additional $50-100K needed to fix the workflow issues.
Key Takeaways:
- Speed Trumps Accuracy in Product Design The software prioritized pricing accuracy over workflow integration, causing even the creator and experienced team members to avoid using it, proving that perfect features mean nothing if users won’t adopt them.
- User Testing Should Start Day One Waiting months to introduce user testing and internal validation cost tens of thousands in misdirected engineering work that could have been caught with basic workflow checks in week one.
- Equity Partnerships Solve Cash Constraints When personal capital limits are reached, converting engineering agencies to equity partners (with CTO roles and vesting schedules) eliminates cash burn while keeping the team that knows the codebase best.
- ChatGPT as Strategic Advisor A single deep contextual prompt to ChatGPT provided board-level strategic advice including price point validation, equity structuring, and partnership frameworks that would typically require expensive consultants.
Listen to the full episode for the complete breakdown of how AI tools guided the turnaround strategy and what the revised 10-minute product roadmap looks like.
(Podcast transcript below)
Hi, Chris Duff over at Serious Land Capital vacant land funding partner. so I promised a, key land price or update on the previous podcast. huge kind of adjustments and updates and kind of changes that had to be made over the last week or so, to kind of fill you in if you haven’t been paying attention or maybe you,
are just kind of hearing about this for the first time. We’ve been trying to develop this land pricer software over the last year plus at this point with kind of progress being made and fits and starts. Most of the heavy lifting started in like August of last year, roughly. And the goal was to kind of take our serious land capital underwriting process.
for being so accurate pricing land and having great results across the US and build that into a software form so that other land investors would be able to simply and accurately price land deals. So they wouldn’t get trapped into potentially bad deals, stay in business for longer, move even faster within their own businesses.
That was the goal coming out of this. And I know I’ve recently mentioned, hey, we had beta testers come in. know, the software was finally in a place where, it could be fully tested. know, pricing was being summarized and so forth. So I had, you know, a lot of some of the biggest names in the land space testing this product. And…
You know, while the idea itself is like, there is promise inherent in this. and the pricing aspect seems to be mostly accurate, which is definitely a good sign. considering the name of the software, it just wasn’t fast enough. you know, it was taking, you know, there’s a bit of a learning curve to use it. was taking, you know, 45 minutes to an hour plus to review a land deal.
Even when I dramatically updated the script to try to shorten shorten it consistently Or In a really substantial manner like it was still just taking too long even within my own business You know, I wasn’t routinely turning to use it as soon as it was available reviewing land deals my assistant You know who really understands our
process thoroughly. Now they were taking upwards of an hour or so to review deals as well too. So like it wasn’t fitting the bill for what needed to be done. Like it was the software was weighted too far towards accuracy of information versus fitting in with the workflow of
you know, people pricing land deals and you know, so that was a major misstep on my side because you know, I had already invested over $80,000 personally into building this out and I had set a basically stop stop limit on myself roughly a year ago saying, okay, I can budget like roughly 75 K bootstrapped
before it just gets unreasonable to see whether I can build this out effectively and get some revenue traction or gonna have to really reconsider and back off. And my estimate from beta testing was that, okay, beta testing is gonna take like maybe a couple of weeks and maybe another five to 10K of engineering expenses to fix some bugs here and there, adjust things.
And it became clear to me, you know, from very, very trusted experienced land investors who provided, you know, deep, deep notes and reviews and really, you know, put time into reviewing this again. can’t thank them enough for their trust here. And, you know, belief in my own abilities to build something. I could just, it wasn’t going to fit within the workflow. Like it wasn’t going to get the usage and
You know, I was starting to have to estimate, like we’re going to need to overhaul this, this software more significantly. There’s probably another 50 to a hundred K of engineering updates that probably need to be done to make this a lot faster. so that was putting me in a, in a pretty tough spot earlier this week. Cause you know, I was just regretting a lot where I should have been first. I should have managed the costs better.
There’s a million things. And I was over-delegating towards the technical experts that I was hiring to do this. should have had, you over the last couple of months, I took a much, much deeper managerial role into confirming the progress and updating where we need to be accordingly. I should have been doing that much, much earlier on. And I should have been introducing initial user tests, even like
really basic level ones and even testing internally, like within my own business, more off the start and seeing, are we trending to where this is actually gonna fit workflow? I didn’t…
Perceived that to be the most critical factor instead. I overweighted myself to like, Hey, we’re the best at pricing in the industry. like, let’s just take our process, throw it into a software. doesn’t really matter how long it takes because the accuracy is what matters. that ultimately was the incorrect approach there. that, know, here we are having to pivot and adjust.
So, you know, being in kind of this stuck place and obviously, you know, the economy is in a rough spot at the moment. And, you know, I was taking a lot of Callan’s teachings and I went to, you know, the pro version of Chet GPT and, you know, gave a super long contextual question. Like, yeah, be, you know, a
top level board member, et cetera. I really try to provide a lot of context and like, yeah, what should I do here? Cause I don’t feel comfortable spending any more money on this, but the product is also not ready. Like people expect the best from me. They expect the best from serious land capital. Like I’m not gonna release something that doesn’t fit that standard. And I’m gonna need like a lot more work done on this product that
just isn’t going to be ready with some minor bug fixes. So what’s the process then? you know, it asked me a whole bunch of other clarifying questions and so forth. And I couldn’t believe how kind of clear the follow-up from chat to be like, it’s just wild how good these LLMs. Like every single week I’m having like a new kind of mind blowing experience with AI, with how good it’s becoming. And it just was…
Some of the most key advice, I wish I’d consulted it much earlier. I know these models are getting better week by week, so it might not have been as handy, but something I should have been consulting with probably earlier, and really the key was just like, okay, yeah, you got free stuff to spend. And just like, yeah, hey, man, you…
tried to put your brain into the product here, that clearly wasn’t the right approach. You need to meet your users where they’re at. It’s got to fit the workflow. Even your own team, even you, aren’t utilizing it at the moment. So it’s like, OK, it’s way too long. We got to figure out how do we get this to 10 minutes or less of property reviews, be way more efficient.
and get like ballpark answers for the pricing here. more importantly, even beyond that, it’s like, okay, really test that price point. Like before we put any more potential effort into this, like go back to some of your testers, go back to other trusted land investors and some of you will be hearing from me over the coming days too, and like really test the price point if this thing like,
really changes to where, okay, 10 minutes or less fits within workflow. know, a hundred bucks a month for unlimited property reviews. Is that going to fit? And, even asking for prepayment for some folks, you know, fully guaranteed, hey, if I can’t deliver on this, get refunded. You know, really confirming that before, you know, doing anything else. And so I was already getting some, you know, initial positive responses. Hey, I think that’s reasonable to do.
But then the next step was like, okay, this engineering piece still has to be done. So then it’s a question of, okay, do you try, you know, I’ve been working with an agency that had been paying, you know, a lot of cash over the past several months. Do you need to find a different technical partner who is willing to work for equity? Or do you figure out what the rough estimate is for?
the remaining engineering work to get the product ready for launch based on all the feedback you’ve gotten. So then you can get your day one customers in the door and start generating revenue. And then, you know, maybe raise a small round of, you know, a hundred, 250 grand or so from, know, various angels and accelerators and so forth. So I wasn’t sure what the best approach was going to be there. I was probably leaning more towards.
Um, just raising a small round. feel like I would be able to do that pretty effectively. Like, you know, I have a lot of skin in the game, invest a lot of money. You know, we have a really successful business within the land space. Um, you know, we have day one customers ready to go and so forth. Like we’re not just entering into this space from nowhere. Um, and a really deep understanding on how pricing works. So, uh, that was the advantage there. And then I had a conversation with, um,
the main project manager at the agency who’s been doing all this work. Obviously they have the most info on how the code base is set up and all of that. We already have a built-in rapport. And I know I’ve remarked, there’s been some issues in the past and so forth mainly on communication. We resolved a lot of that more recently. And I take that upon myself of just over-delegating earlier on when I should have been having a firmer hand.
and a firmer grasp on being a manager on that side. And completely unexpected for me, know, the project manager was like, hey, we’re open to considering working on this further, like from an equity position. And to me, that’s like kind of best case scenario, because all of a sudden I can, you know, off my dev spend. Like I’m capped on personal financial
expenses from this, like, keeping my own word of like, okay, I’m at the limit of my risk tolerance for personal expenditures on this software. And, you know, can get the engineers who already know this product more deeply since they’ve already built the initial version and figure out, okay, that’s probably the fastest way to get to the next step.
And where, you know, the project manager would consider, okay, even a possible CTO or fractional CTO type role with us. So, and he was like, okay, you know, put up to put a deck together. Like let’s have a brainstorming session, start figuring out the user feedback. What are the next steps need to be so we can get this down to 10 minutes or less. So we already started having those meetings and I threw a deck together and like, that’s so outside of my day to day is like trying to figure out vested, you know, vesting schedules and.
what equity even might look like in a situation like this in rev share and everything. So I went back to the chat GPT and we put together a deck within less than an hour and had just incredible suggestions again on how to structure equity and so forth and threw all that over. And it’s not like firm or anything, but it’s really trending into a good place. Cause again, I think just being a,
being a leader when you’re looking for the right who’s and this is something Chetri Pati was telling me. was like, Hey man, you’ve been in a builder mode for too long. You got to be a CEO. got to leverage, use leverage more effectively and find more who’s in a kind of more strategic manner. And you know, that’s always back to the Dan Sullivan thing is like as a leader, it’s your job to figure out the what and the why. And you know, the who’s, the who’s will figure out how.
how to do that. So, I’ve just kind of really embraced that, especially over the last couple of years, like, Hey, your, your results within your core business are really compelling and you as a leader within that are also really compelling individuals. So, people see that vision and want to be a part of it. And, that is what, you know, now it might set up to where I can completely eliminate my cash burn.
Get people to work for equity. Yeah, obviously giving up some ownership, but to me, okay That’s worth it if I can actually get this this product off off the ground here And you know still work with the people who already understand this product the most So, you know clearly a lot was happening over this last week in the midst of like all the markets crashing and everything too It’s been a kind of Wild West time But I wanted to update you all where we’re at
You know, it’s much to my regret again. I wish I could have delivered on this product based on like the original timeline at end of 2024. It just kept getting delayed. Now it’s going to be delayed probably at least another few months. We’re going to try to sprint as much as we can. And if the agency decides like they don’t want to move forward with it, I’d say like we’re probably 90 % going to be there. I’m feeling just based on already some of the initial conversations and work going on, I think we’ll be able to work something out.
in a fair manner But you know if I had to go raise outside and so forth or find a different partner like I’ll go do that It’s just gonna take take extra time To accomplish that so, you know, it’s gonna be a few a few more months But again, I’m not gonna release anything. I promise you guys that that won’t both fit my own standards from my own business as well as the industry as a whole and a lot of lessons a lot a lot of lessons learned
building the serious land capital business is just very different from land price or its own set of problems and situations to deal with. yeah, got like 103 items probably that I would have done either much differently or somewhat differently over the last year or so. But here we are, business is messy, business is hard. It’s no surprise.
Uh, things have to change on a week by week basis and you got to roll roll with, what comes up. Um, again, go back to my mentor, like Trevor McGregor and everything. Um, you know, it’s all about speed recovery, speed recovery. Uh, you know, can’t get trapped in your own bad thoughts and all that for. Yeah. And any longer than the necessary. And I just really embraced that and got a lot better about that over the last few months, especially of like, okay, yeah, this sucks.
Let’s figure out a solution here and moving forward. A lot of people struggle with that. I used to struggle with that all the time. Get stuck into dark spirals. And now I just feel like I’m able to bounce back, figure out the next step and move forward. So hopefully you guys are picking up some lessons from this. Obviously it’s vulnerable to talk about it. It’s not an immediate win. That’s for sure. I mean, I think there’s some small wins now of.
moving things back in the right direction to solve. But again, another lesson, like I always say now more recently, like don’t wish it were easier, wish you were better. So even though I really wish it were kind of easier, like I have to remind myself, yeah, you just weren’t good enough. Now you have to be better in order to get over this hurdle. Other people have done it before. If you believe in yourself, you can do it. You have the right resources, right relationships in place.
figure it out. that’s where we’re at. If you’re looking for funding, SeriousLand.Capital, land daily diligence on Mondays and Thursdays, zero cost review land deals. Remember April 17th, we’re going to be doing a mini-unconference. So if you’re open to having a hot seat and being coached by multimillionaire or multimillion dollar land investors,
to help you solve problems in your own business, please let me know. Those are gonna fill up fast, I’m sure. And lambpricer.ai, which I just talked about for quite a while here. With that, take care everybody. Subscribe and share, bye.
