This episode details the construction of a personal AI board member through answering 115 deep questions across eight domains (core business operations, deal evaluation, personal performance, relationships, health, financial philosophy, purpose/legacy, mentor integration). The multi-week Whisper Flow-enabled process created a backlog of frameworks for conversational AI consultation, with the question-answering exercise itself generating unexpected insights and new mental models.
Key Takeaways:
- Questions force framework articulation Answering “describe your philosophy on debt and leverage personally versus in business” revealed gaps in previously assumed clarity—the writing process crystallizes nebulous thinking into actionable principles through forced consolidation.
- Purpose/legacy batch most valuable Batch seven covering destiny, legacy, 20-year impact vision provided the deepest value for reorienting daily action toward true north—getting lost in tactical weeds makes these fundamental questions essential for course correction.
- Whisper Flow enables depth Voice-to-text transcription made 115 detailed responses feasible over weeks versus months of typing—the 10X speed increase allowed comprehensive coverage impossible through traditional writing methods.
The value materialized before AI implementation—creating clarity across business and life domains through structured self-interrogation justified the effort regardless of eventual project performance.
(Podcast transcript below)
Welcome to get serious. Wanted to give you all an update on that Sage mode AI project that I had remarked on over the last couple of weeks. So I’m nearly done with the initial version of this. It’ll be ready by tomorrow. It’s taken me a longer time to get this ready, but you know, an ambitious.
project and to recap for those who aren’t familiar. so I really wanted to create, well, you know, to take even a step back, you know, just using AI everywhere within our business. some of the most impactful AI usage, that I’ve had personally is just, you know, utilizing it as a thought partner, especially for trickier decisions or mental frameworks to consider.
you know, almost like having a, pocket board member, especially the way you might program your personal AI, on how you might like to be answered. and to me, I created to be a, a bit more harsh and brutal in its assessments. Like, you know, high performing entrepreneur just like leave it to me, or give it to me.
as cutting in raw as necessary here, which I think is also a good compensation for the general obsequiousness of AI, meaning that it is more eager to please in general. So trying to give it a little bit more of a sharper tone to cut closer to the truth is generally more beneficial.
In my experience. so what I wanted to do is, you know, the initial inception was like, okay, most of us, um, uh, are ultimately our own best coaches. long as we actually follow, uh, our, our, our own advice, you know, sometimes we might need to hear it from, from others here, but, generally, um, like you have the tools to figure out what you need to do. Um, if you actually just take the time to.
Ask yourself it, consider it, and put it into motion. And so I wanted to build an AI project that had, you know, my quote unquote higher self, you know, my sage self, so to speak, answering tons of different questions across, you know, business life, et cetera. So that I would have a backlog of my own frameworks.
across life that I could just reference and, you know, discuss within a quad project, mainly within a speaking format. Like I don’t necessarily want, you know, we’ll see how it is in practice, but I more wanted to have conversations with this project, even on a daily basis or considering more difficult scenarios, versus just typing into the AI project. And additionally, beyond my own answers, like I would have my business partners.
Answers not you know the full 100 plus questions that I’ve been doing personally, but mainly related to the business Then I have you know a whole bunch of YouTube transcripts and mastermind notes and quotes That are are more
relevant to just general mindset and also business principles. And there’s probably going to be some overlap with this project, with other projects that I’ve built to answer certain questions here. fortunately, that’s the thing with AI, sometimes spending all this time on building up one project can have compounding effects for others. And it’s just experimental in general.
So that was the overall impetus here and I got a lot of the parts done. know, naturally always procrastinate or at least I do. Um, but I think a lot of people can relate, um, you know, to save the hardest parts for last within a project. So it was easier for me to put together, you know, YouTube transcripts and, you know, compile some notes from masterminds quotes and so forth. That was just easier to upload in the project, but to actually go through the extensive process of answering.
a whole bunch of questions that I really asked Claude to, you know, create a ton of different questions oriented around this project. So it would cover like basically every domain within life, or the vast majority of them. that might have like more of a, a bent toward wisdom, and practical advice. that was really the goal here. And so,
Yeah, I have one more batch to do. It’s taken me quite a while to get through these. Cause like, you know, if you really want to build the best possible project, like that’s the thing, like AI when it works properly can, you know, be life changing and business changing when you start to implement the systems. But you know, to get the best results possible, I usually still have to do a lot of leg work. So, you know, inputting the correct amount of knowledge is just critical in order for you to get the,
project to actually work as intended. So, you I thought answering these questions like might be a couple day process, but it has been far longer than that. Because again, if you, know, some of these questions are super in depth, or you could answer them, you know, very in depth. And so, you know, if I want the best possible, you know, Sage mode project, like I need to take the time to answer these.
Effectively and there’s like minimal overlap between them as well So like I’m finished 99 questions so far and on the last batch. There’s like another 15 or so roughly and So then I would be finally ready to start testing this thing out But to give you an idea here on what those questions look like It was it was split over six domains, but they actually
broke it down into like eight different batches here. So the first batch, you know, it went more business oriented and then, you know, took steps back to more like, you know, abstract wisdom. Um, so first it was more on the core business operating system, you know, my decision making strategy, uh, you know, like an example question is, um, you know, describe a time when you made a difficult business decision that turned out brilliantly. What was your thought process and what principles guided you?
Like it’s not, you know, it’s not necessarily a question that you can answer within one or two sentences, right? Or you really got to break this down. Or I guess you could answer it shorter, but again, to actually like work through this and get the best project knowledge possible. Like you should really write this out. And like, again, but this has been using whisper flow over the last quarter, maybe a little bit more than that.
I, it’s just so much easier to do because I’m just, it’s basically transcribing as I’m speaking here. If I had to type this out, like I probably would have done like 10 questions so far. It would just be so much slower or you could just use, you know, a voice memo and have to transcribe later. But you know, the accuracy might be a bit off. like whisper flow, if you are not using that, like I basically never typed anymore. It would be so much more effective emails, text communications, you know, prompting, especially for AI. I guess just it’s key. So it allowed me to go way, way more in depth.
and then the next batch was deal evaluation and market positioning. That was a lot, you know, related to what we’re doing within the land business and land Pricer. and then it oriented more around the personal operating system, peak performance. you know, like what’s your weekly rhythm for maintaining peak performance across multiple businesses? How do you structure your weeks? again, to answer that in depth, like it takes.
You know, some real concentration, like some deep work to answer these questions appropriately. and I got a lot of insights doing these. Like I’m actually going to have a lot of different podcasts going over this because, you know, answering these questions actually helped me realize and create new frameworks that. I hadn’t necessarily had in mind before, or I hadn’t articulated because yeah, if you have to answer some of these questions, it just, it forces you to figure out, okay, what.
how do you actually feel about these subjects? And if I find myself more, you know, repeating certain frameworks and ways of thinking, it’s like, that’s also a trigger for me to realize, Hey, this, this line of thinking is probably more important to you and a more consistent through line versus, you know, other, other ideas that, you know, might be batted around in your mind a little bit, but when it actually, you know, when it actually counts and what’s
when you’re trying to answer as truthfully as possible. And I’ve done this over multiple days too, so like different moods and so, but again, I try to do it when I’m high energy, right? Because it’s, you know, 10 out of 10 self-answering. So, you know, I don’t want to slack on any of these questions either. And then it went into relationships and communication mastery, such as…
You know, describe your approach to building genuine relationships with high value content, contacts, um, for example, investors, partners, mentors without being transactional. Um, so again, like not, you know, yes or no questions, right? You really got to think through how, uh, how to answer this. Um, and then it went into health and vitality mastery. So lot on like, you know, physical fitness.
mental fitness as well. That was actually probably the easiest answer. I’m like probably the most locked in from a lot of these and answer these questions a lot. Probably most, one of the more consistent areas of my life. and then it went into, and just an example of one of those, like, you know, how, do you maintain physical energy, health and energy during intense business periods without letting it slide? so I generally have a pretty good framework for, for that. and then.
The next batch was financial and wealth philosophy. So, for example, like,
What’s your philosophy on debt and leverage both personally and in your businesses? And like sometimes when I was answering that, like especially quite a question like that, you know, I started to backtrack a little bit and realized maybe I don’t, I don’t have the best answer to this particular question. So that’s the thing is like, you can always come back and edit this as you grow as a person. and you know, just have different strategies.
across the course of, of your career here. But like, you know, again, the point is some of these questions are like, start delineating. Okay. What’s, what’s your real truths here and how do you, are you actually taking action? within, you know, some of these pieces of life that, you know, cause I definitely have levered up and I definitely use equity, but like, what’s my strategy and more comfortable from the personal side or from the business side and what’s your track record of.
of doing that. you know, again, answering some of these questions. Realistically, like it takes a lot of work. And then the next batch was purpose and legacy. So I just finished this one. This was batch seven. So again, like pretty. Pretty deep stuff, like how do you think about concepts like destiny, luck and personal responsibility in your success like this batch?
or, know, how do you want to be remembered? What legacy do you want to leave behind? What’s your 20 year vision for the impact you want to have in the world through your businesses and beyond? like really forcing you to boil it down what you’re working for and put it into words. Like we sometimes might have more nebulous goals, or what we think we want, but you know, when you actually have to note it all down, it just, it forces a certain consolidation of thoughts.
so that was really deep. I feel like this batch might even be the most valuable out of all of them, just in terms of reorienting. Okay. What is your purpose? What are you going for on a day-to-day basis, especially from a thought partner perspective, because we get lost in the weeds so often, that what is going to bring us back to what our true North is.
And then the last batch that I have to answer is just a mentor integration and frameworks. So it’s like, you know, if I had a couple of core mentors, either people I know personally or not, you know, like a Hermosy or Trevor McGregor, Andrew Lee, for instance, you know, how am I incorporating their frameworks and advice within my life? And, I also have different knowledge, project knowledge within the project that is based around their own frameworks. like,
creating this additional piece of project knowledge on how I utilize it within my personal frameworks is just another callback for how the AI would relate to me on those various subjects. So I clawed to, you know, this is an excellent job, like almost 115 questions, really, really in depth, pretty much no, nothing repetitive or nothing that I felt was pretty irrelevant.
for for suggestions here and then it’s all going to go into the project knowledge and then then we’ll be off to the races and Being able to share more on how this is actually being implemented But you know, even if I never used this Project or just you know, it’s kind of a dud and didn’t work as I intended it to be which I find to be far-fetched Like this was a very helpful exercise for orienting
around, okay, getting clarity on so many parts of my life and my business, so that I readily have these answers in mind, even if I’m not necessarily consulting them again. But, you know, have it all written down and within notion for ready consultation as needed. by itself, it was just a very helpful exercise. And if you haven’t done something like this, I know there’s a lot of like journal prompting effectively, like it’s a really hardcore project. me a long time to do almost all of this.
But you know very worth it to gain that clarity within your life So I’ll be doing some other podcasts about this just for some of these other breakthroughs of questions that really made me think and create other new frameworks here, so We’ll get back to that, but we’ll go ahead and wrap this one up today Serious land dot capital for any of your funding needs
Land Daily Diligence Facebook group for zero cost review of your land deals and landpricer.ai for the most reliable land pricing tool on the market. We are going to have it ready for testing by the end of this week. I was just getting my last kind of product updates assigned to my engineering team yesterday. So rolling on that, I really can’t wait to use this in my own business ASAP here. Like every time I’m reviewing a property now, it’s like, man, I just.
I’d rather have land pricer to do this and just losing sight of what I’m trying to do. So subscribe and share. Catch you all next time. Take care, everybody. Bye.
