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Chris Duff

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The Uncomfortable Truth: How AI Exposed My Conservative Thinking | Ep. 177

This episode reveals how building an AI money coach during the Accelerate to Automate course forced confrontation with conservative revenue projections and psychological barriers around capital deployment, leading to defensive responses when the AI challenged assumptions about SLC and LandPricer growth potential with penetrating questions that human mentors rarely ask with such consistency.

Key Takeaways:

  • AI Thought Partners Require Extensive Context Building The transformational value only emerges after hours of answering questions and uploading relevant files—superficial interactions produce superficial results, making deep context the competitive moat.
  • Sub-0.5% of Claude Users Utilize Therapy-Style Conversations Despite concerns about AI therapists replacing humans, actual usage for deep psychological work remains extremely rare, indicating massive untapped potential for strategic thought partnership.
  • Uncomfortable AI Conversations Force Growth Without Social Consequences The ability to step away without facing human judgment makes it easier to engage with brutal truths and challenging questions that even close partners avoid in daily interactions.

Listen to the full episode for insights on building effective AI thought partner systems.

(Podcast transcript below)

Hi, welcome to Get Serious. Today, I have another update on utilizing AI within your business. Almost every single day that passes, there’s just another kind of eye-opening experience, some larger than others, but generally, it’s just upward-facing arrow in terms of just potential opportunity and actually realized opportunity.

as myself and my team continue to utilize these tools. So, as we near the end of Callan’s, accelerate to automate course, we had just built out this money coach. So I spent some extra time, like really, really deep diving, making sure we have the right info and, the name kind of gives it away. It’s just, you know, accounting for, you know, whatever, the status.

of your financials within your business and trying to kind of coach you along the path for breaking through boundaries and figuring out what your actual revenue goals should be and could be achieved if you really push yourself, especially with the 10x mentality over the next three months, six months, 12 months, up to five years or beyond.

And also, you know, approaching it from like a psychological perspective to not just, you know, the raw numbers, but how you think about money and past history of your experience with money or what type of environment you grew up in to. And that all comes into play when we actually make business decisions. So I spent a whole ton of time on this. you know, that’s the thing is like kind of realizing there’s a lot of overlap.

with some of these AI projects like that Sage mode I talked about the other day that I’m still building out. Like I’ll probably want to include a lot of this info from the money coach into Sage mode. They’re a bit different, more overarching strategic versus very money oriented CFO slash therapist kind of. But I think a lot of the info or the knowledge within both are probably relevant to each other. So I’m going to play around.

with that. But as I was wrapping up this kind of initial experiment with the money coach and just trying to set some revenue goals, and it took me a bit longer because I’m trying to do both serious land capital and land pricer and orient what the potential is for both of those. I imagine SLC is that that’s going to be kind of the primary driver. It’s just more capital intensive, but I really view the

to businesses as intertwined because, um, like inevitably I’ll need a tool like landpricer, um, to take SLC to, uh, the highest level possible anyway. Like I just don’t want to be continuing to have like an art associated to, uh, underwriting deals and just, you know, depending more on my mood or energy to figure out what all the right comps are.

or my team members, doesn’t matter whether I’m the one doing it or not. Ultimately, that’s going to be a bottleneck that we have to break through. So that software has to be created ultimately. whether they’re fully separate businesses or not, I was just trying to work that through and just talking to this AI money coach. It just helped really reorient strategically on how I should be thinking about land price or being.

Accelerant to SLC’s growth to you know, 10 15 50 million dollar top line business over time and You know whether Whether that is you know its core function or you know the ability to Bring it to the masses through B2C or potentially B2B

partnerships, like that’s an additive value. But like ultimately that core piece of like, okay, I need a piece of software to build out SLC to its top potential that will kind of keep the North Star oriented for both companies on the level of solution that is required, regardless of what each revenue stream might appear to be separately. and

AI kind of gave me different legal frameworks on how to potentially navigate that as well being in different LLCs. Obviously I own both of them. So that was kind of uplifting. Is that something I struggle with on a day-to-day basis? And then, yeah, especially accounting for, you know, we have this ambitious growth for serious land capital and

You know, and I was answering some of these questions about the revenue goals to the AI. Um, I almost found myself getting a bit, a bit defensive. You know, kept saying, Hey, here’s the real truth. Are you being a bit too conservative here? And, like, you have this capital on hand, like, why aren’t you use it? Like, if this is really your goal, why aren’t you going to be pushing in this direction? And it was just asking really savvy questions that, um, certainly, yeah, you can get from a good human mentor or, you know, another business coach, but like they’re not all.

you know, always available at any given time. or you’re not necessarily going out of your way to be asking these routine questions. And most of time it’s just you in your head trying to work through things, or maybe you have, you know, some partners or employees in the business, but that’s kind of an echo chamber, as well here, especially if you have, you know, more charismatic personality, which I would include myself in, in that sense. And you can kind of just steamroll over other ideas and

just rationalize through your thought process, but having these really thoughtful questions being asked and just really challenging my assumptions to the point where I was almost starting to sweat a little bit in terms of like, this is kind of tough to answer here. And maybe I’m not being as open-minded as I could be or

as confident with my decision-making as the numbers would seem to suggest we have the capability of doing. And so that was just an extremely helpful exercise that, you know, it’s probably AI’s biggest gift at the moment is just serving as a potential thought partner. know, you know, like, you know, 95 % plus of people who’ve ever used AI are still using AI or like kind of treating it as a souped up.

Google search which is just you know, doesn’t even scratch the surface of its potential here But yeah when you can really get into these thought partner Conversations that have the proper context especially about your life in your business like it’s it’s truly transformational especially because I’m using whisper flow and some just talking natural language not wasting time typing It’s just a back-and-forth to to really sort through thoughts and

You know, just the way you can quickly kind of orient numbers as well, too, just running through, okay, here’s some revenue projections. Here’s like typical SAS churn rates and stuff. Like a lot of outside knowledge that I wasn’t necessarily having on hand or I was just pushing off. I’ll get to that later on. I was like, okay, now I can start building some of this stuff in and what actually might be realistic or, know, like kind of like conservatives, you know, middle of the road to kind of aggressive targets for revenue across both.

both of the businesses and giving me some different ideas on how to approach each. yeah, just again, kind of stunning conversations in terms of both the level of the quality of feedback that I was getting and improving my own decision-making as well as just, again, it was just making me uncomfortable to answer these questions. Like these are just tough.

Deep questions and I orient my AI like tell me like hey, I’m a high performing entrepreneur Just give me the real truth. Like don’t hold back on this Like I I prefer that type of response there and that’s the thing like a lot of even if you ask that of people You know, we’re social creatures like usually, you know, unless you really really know someone and sometimes even then it can you want to be? Even more careful on how you say things but you know How many times do you actually have a

Face-to-face or even a phone conversation where somebody is saying like here’s the brutal truth about it like you’re just You got to change your mind. So it’s pretty rare. I feel like I’m around people who are pretty honest And forthcoming with the way that they speak but like those type of conversations Certainly don’t happen every day At least not in my life even in my own marriage. Like you’d think your closest partners

I mean, sometimes we’ll have more serious conversations, probably more often than a lot of couples just because we’ve built that into our cadence. But they’re rarely comfortable, right? Like none of these, really rarely like go out of your way to get into them. And so sometimes I think even having to say I words like, okay, I can step away from the conversation anytime. And I don’t have like another face kind of judging me at the same time too. Like it’s just maybe a little bit easier to work with.

And again, I just don’t think that many people are using stuff like this. We don’t know the numbers behind Chet CPT, for instance, but I know they did a recent study on Claude and everybody’s worried out like therapists, everybody’s gonna use an AI therapist, but it’s like sub point 5 % of all conversations on the platform, maybe even less than that. But yeah, I mean, it’s super, super small are actually using it for that, for that primary objective. So,

Yeah, there’s still a lot of room for us all to adapt in our own usage and determine what feels best for us at any given time. But I’m continue to be bought in just because like, again, you got to do a lot of work with the context and the knowledge. you can’t, I mean, it can be helpful just going to the AI and like just kind of working through things. But if it doesn’t know your situation, like the quality of the results are just not going to be nearly as good. like that’s the moat.

that you have to build and kind of cross over. You know, can take hours of work to properly answer all these questions and pull all the relevant files and data that are going to inform the decisions. But you know, that’s what it takes to get a proper thought partner, right? So just wanted to share that there. Yeah, just give it a shot if you haven’t already. Like these are…

These are truly transformational conversations. I’m to be returning to this often. With that in mind, SeriousLand.Capital for any of your funding needs, zero cost review of your land deals, Land Daily Diligence Facebook group, and LandPricer.ai for the most reliable land funding to our land pricing tool on the market. Subscribe and share. I will talk to you all next time. Bye.

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