What happens when a Marine veteran, entrepreneur, nonprofit founder, and early power user of Agentic AI sits down with educators to talk about the future of learning?
You get a conversation that is practical, provocative, and deeply human.
In this episode of the AI x Higher Ed Podcast, Rich Brown shares how he is using AI agents across business, nonprofit leadership, curriculum development, and personal productivity. But this is not a conversation about replacing human judgment. It is about strengthening it.
Rich makes the case that AI should push education to focus less on final products and more on process: the questions students ask, the iterations they work through, the decisions they make, and the judgment they develop along the way.
We also discuss:
✅ Why AI is already transforming real-world workflows
✅ How Rich is using AI to help build a leadership academy for high school students
✅ Why “show me your process” may become one of the most important assessment questions in education
✅ What schools can learn from military leadership and mission-driven problem solving
✅ Why students need agency, judgment, and continuous learning skills in an AI-shaped world
✅ How veterans may play a powerful role in helping communities navigate disruption and rediscover purpose
One of the strongest takeaways: the future may not reward people who simply know the right answer. It may reward people who can identify meaningful problems, lead others, use powerful tools wisely, and keep learning as the world changes.
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Chapter 1: Welcome and Introduction to Rich Brown
Anand: Well, we’re excited to welcome you back and to have this conversation with Rich Brown. Rich is a Marine veteran and small business owner here in Fredericksburg, Virginia. He’s also the founder and president of the nonprofit Guideon Foundation, which supports veterans and first responders by sponsoring events and training for those groups and young people in the community. I met Rich recently after a speaking event and had a chance to meet and talk with him about his work. Welcome to the podcast, Rich. We appreciate you being here.
Rich: Thanks, Don. I appreciate you giving me your time.
Anand: Awesome. So we first connected over a discussion about agentic AI, and you were the one in the room who had a much better story about using agentic AI and a better experience than anybody else. Tell us a little bit about how you’ve been using AI, agentic AI, in your work over the last couple of months.
Rich: Sure. When we met up in person, I told you that I was a little ashamed that I had talked about my spending habit with agentic AI as if I’d worn it almost as a badge of honor. All in total over the last two months, I’ve spent somewhere between two and four thousand dollars in Anthropic tokens. But really, I shouldn’t celebrate the fact that I don’t budget well for agentic AI.
I have gotten much better. I’ve created an infrastructure in which my agents are a lot smarter about the tokens we’re using. And I think I said this when we met — I use this metaphor to tell somebody else about the setup, and the fact that if you’re speaking just about Anthropic, obviously there are other services, but if you’re using Haiku, Haiku is about on the level of a college graduate in terms of what it’s able to produce. If you’re using Sonnet, that’s more like somebody who has graduated from college and has some experience actually doing the work you’re asking it to do.
Then Opus 4.7 is like asking — it’s like paying someone who’s famously good at the thing you’re asking it to do. And I’ve been very, very poor about my spending when it comes to having someone famously good manage my calendar and my day-to-day functions. My famously good writer doesn’t need to be calculating my calories for the stuff I’m eating on a daily basis. So knowing which model you’re using and being deliberate about the usage is smart — and smarter than I have been, unfortunately.
Anand: Well, now we know why they had to move to the Colossus data center — because of all the demand in Fredericksburg coming from your agentic workflow. So tell us how you’ve been using it in business, because this is something I think a lot of educators don’t really have a good appreciation for — how transformative it’s been for some workflows.
Rich: Sure. To back up a little bit, I own two companies and I serve as president of a nonprofit. So we could take any path you want, whether it’s the executive protection business or the gym or the nonprofit. I can say for the nonprofit, right off the bat — because it’s something I’ve been working on lately — we have a Service Leadership Academy that we’re hosting this summer where we’re going to take 35 rising high school seniors and teach them leadership from the perspective of veterans and first responders in the community, and some guest speakers from around the country.
I like to move fast. Whereas a decade ago it would have cost dozens of thousands of dollars to put together the curriculum and have it all vetted and reviewed and so on, I’m speaking with an agentic AI agent and developing the curriculum rapidly. I’m using source material I take a lot of confidence in — whether it’s Jordan Peterson, Jocko Willink, books like Tribal Leadership, or the various team-leading books from military veterans — using that as the foundation.
Where I think a lot of people screw up with AI is they’ll make a good prompt — they’ll tell the AI the role they want it to fill and then they give it a well-crafted prompt, and then they ask it to produce something like “develop the curriculum for this eight-week course.” That’s good. That’s above-average usage. That’s not just using AI as an advanced Google search. But where they don’t go the next step is to say — for example, this curriculum I’m developing, we’re going back and forth on about 400 questions that my agent is asking me about the curriculum before we ever write a line of text. Really fleshing out your ideas and the intent and the application — I think that’s where a lot of people fall short. It’s one thing to use AI to answer questions or to solve homework problems. It’s another thing to help it really dive deep into what it is you want it to produce.
Chapter 2: The Cost of AI Experimentation and Smarter Token Use
Anand: And I was going to say — I think it’s definitely true in my experience that you should also get some free Claude tokens for your claim that it’s as good as a professional. I think I’m an unpaid fanboy spokesman.
Stefan: There’s got to be a way to maybe help monetize that with some short clips. But I think that’s definitely the case. And how are you using it? That curriculum example is something I think a lot of our listeners can relate to. But I’ve also heard — and this is incidental — I’ve heard from a number of kids who graduated last year or so, and they said, “Oh, our professors told us we can’t use AI. Don’t use AI in school, because you’re never going to get a job if you use AI at work, or if you tell the people who are hiring you that you used AI.” And obviously that’s kind of not the case. What are some ways that you or your employees you’re training are using AI, or that you’re encouraging them to use it?
Rich: Well, first I want to address the elephant in the room. I don’t want this to sound like a stab at you directly, because you work within the academic field — but I think a lot of professors are telling their students not to use AI when they’re developing anything for their academic pursuits. And unfortunately, it’s probably going to be the teachers and the professors who, in 10 to 20 years, aren’t going to have a job, all due to AI. I think the schools are going to have to figure out real quick what the future of academics looks like, because they’re not keeping up with what’s out there and what’s possible. I admire you two for trying to get ahead of that curve, and I think that’s what you’re doing with this podcast.
Your question was how I’m encouraging my employees to use AI. That’s a good question. I own an executive protection business — which is a really almost pretentious way of saying bodyguarding. But it is the very professional bodyguard. We’re not hoodlums protecting rappers — we’re protecting Fortune 50 CEOs. We’ve started using AI a lot in doing what’s called advance work.
Advancing any objective is when — let’s say I’m protecting a CEO who’s going to be meeting with the president at the White House. They’re going to fly into Dulles from probably California, and we’re going to pick them up at Dulles, drive them to their hotel, take them to whatever meetings they have scheduled in the area, meet with the president, maybe spend another day in town, and then get back on an airplane and head back to California. We will spend up to a week or two going to all of the places they plan on visiting before their actual visit. We’re looking for ingress and egress routes, all the different safety concerns, how our principal may be vulnerable in each venue, developing relationships with local security and local law enforcement — so that we are 100% ready long before they ever set foot in that room.
Rich: A decade ago, you had to physically go to all of those places, shake all those hands, get the phone numbers for all of those people. We’re able to do it much faster and easier and do most of our homework first. I’ve got an agent whose entire role is — I give them a location, and they immediately produce, if the information is public, the director of security for that location, and the nearest police, law enforcement, fire, and the closest emergency venue — all of that, if I just type in a location, because it knows what I’m looking for. Does that kind of answer your question?
Stefan: Yeah. One thing I’ve found doing this for a while is that just talking to people, you learn about all different types of use cases. The first time, I think it was in the class I was teaching at Mary Washington, a student said, “Oh, I have trouble communicating with my roommate, so I use it to help me draft my text.” I’m like — people are using this for so many different things. It’s really going to explode. And that’s another unique use case probably many people didn’t know about till right now.
Chapter 3: Using AI to Build Curriculum for a Service Leadership Academy
Rich: I’m not ashamed to tell you — and maybe I shouldn’t say this publicly — but I have an agent that acts as sort of an intermediary between me and my ex-wife in terms of custody matters and that sort of thing. It typically speaks from the point of view of an attorney and that kind of mindset. What I’ve done is created an agent where, if I give it a screenshot of a conversation, it has all of the history of the last two or three years’ worth of text-message exchanges between me and my ex-wife. If she sends me a message, I send a screenshot to my agent, and it gives me a kind of coaching of how I should respond.
What it’s looking for is: how do I stay — I’m not creating conflict, I’m trying to be as amiable as possible and keep 100% focus on what’s best for my daughter. It’s not about winning the argument. It’s not about winning more custody or anything like that. It’s just: how do we keep this 100% child-focused and move forward? If you prompt your agent in a way that those are the results you expect, it usually comes out pretty good.
Don: There’s a use case for everything, I think.
Stefan: What I like about your approach, Rich, is — I think this illustrates it, and also something you were saying before, like working on the curriculum — you don’t just offload it and tell the agent to go do it, or, “Hey, just handle this communication with so-and-so.” You have gone through this process so that you make sure the agent really understands your perspective. But I imagine that process also helps you flesh out that perspective. When you were telling me the other day about having that series of questions for every item, you put a lot of time into that.
Some people might say, how do you really save time if you’re spending all that time putting it in in the first place? But what I really appreciate, and would love to hear your thoughts on, is — how does that maintain your control over the thought and the idea, so that it’s not offloading it; it’s just extending your own ideas and capabilities?
Rich: Yeah. It’s more about refining things than offloading. To answer your question within a question, it saves time because you do it once, and then you know what to expect when you have to do it again. You don’t have to tell it twice — unlike an employee, where if it’s worth saying, it’s worth repeating. You don’t typically have to repeat yourself with AI.
Stefan: But your process — you really retain, you really maintain control over those ideas. Take the example of the curriculum: you go through this process where, for each point, you’ve trained it to ask you so many questions, so that you really flesh out an understanding of it, so that it’s really your idea. Talk about why you design it that way. What’s the benefit of doing it that way? Do you really feel like it’s still your idea and you control it?
Rich: Sure. There’s a quote I keep coming back to recently — I don’t want to paraphrase it or misquote it, but it’s: “Unspoken concerns are premeditated disappointments.” It’s a way of saying: if you don’t communicate every concern you have, every limitation you have, you’re just setting yourself and the other involved parties up for failure.
Rich: I would challenge the professors to say: use AI — absolutely use it, because it is a force multiplier. But be prepared, when you submit that final assessment, whether it’s a project or an exam or whatever, to tell us how you developed it. What questions you had. What obstacles you faced. What you had to do differently — you thought it was going to go this way, and then you had to change direction. Instead of focusing on preventing the use of AI at all, maybe you need some kind of counter, to say, “I had 14 different iterations. I had 87 iterations before I got to this final thing I turned in.” Because that’s where the work is — how many times did you have to iterate to get to the final project. Does that answer your question?
Anand: Yeah, that definitely helps. What you’re getting at is something we’ve talked a little bit about: we’ve got to find a better way to assess student work. It can’t just be “look at the final product.” What you’re really getting at is it’s got to be an interrogation of that process — how did they get there?
Rich: It kind of flips the coin, doesn’t it? Because if the teacher is giving the same student every assignment or every exam and then checking it against an answer key, and that’s how they do their work every day — well, that’s the laziness you’re trying to prevent in the student, isn’t it? What if, instead, you’re having conversations with the students and saying, “How did you come to this conclusion?” or, “In getting to this conclusion, what presumptions did you have to challenge?”
Chapter 4: Why Better AI Use Starts with Better Questions
Anand: That’s all active learning. Going from a system that largely trains everyone the same way with the same stuff and then gives everyone the same assessment, or similar assessment, to see who conquered it — it has limited use, and it’s going to be hard to move beyond that. But I’m wondering, with your summer program — I’m sure you’re not going to be giving papers and tests, or too many tests. What are some of the, to use a fancy word, instructional modalities or approaches you’re going to take to working with the students? How are they going to learn, demonstrate what they learned, and integrate, I assume, some AI into the projects they’re working on? What approach are you taking for the summer?
Rich: Sure. To give you some context, the eight-week leadership course is divided into four phases. Each week is two four-hour sessions, probably in the evening, but we’re going to try to feel out what works best for everyone involved. Maybe it’ll end up being mornings — I don’t know.
Rich: The first phase is self-awareness and self-leadership. If you can’t lead yourself, how can you lead others? So before they ever set foot in the classroom, we’re going to give them a number of assessments — MBTI, the Big Five. I’m a big fan of the CliftonStrengths test. We’re going to give them all those assessments before they ever come to us. Then they’re going to be divided into five teams, and those teams are going to be structured around conflict. We want them to be in teams where they’re going to have conflict.
We’re going to put them in groups based on people we think they may not get along with, based on their different personalities and how they look at the world. We’re not even going to talk about those assessments we gave them until the second week. First, we’re going to challenge them to produce things as a team and let that conflict come to the surface, and then we’ll talk to them about why they’re dealing with these conflicts in the second week.
The second phase is all about good and bad leadership — what it looks like. Case studies throughout history. We’re going to meet on a battlefield in the Fredericksburg area and do a battlefield study: what decisions had to be made, the decision-making process, how it looks in real life. The third phase is developing and leading teams. The fourth phase — the one I’m most excited about — is our community leadership project. Back in phase two, they’re going to start talking about what they want their leadership project to look like, because as a team, all five teams are going to go find a problem in their community and try to have a positive impact on it. You’re not going to cure cancer. You’re not going to end hunger. But you can find a problem in your local community and try to leave it better than you found it.
Stefan: I mean, that sounds incredible. They should put that in schools. Seriously. That kind of project-based learning is exactly what students need, because not only does it better motivate them — they see they actually have an impact, they’re doing something, it’s not just arbitrary, not just made up from exercises that don’t have a real-world impact — I think you’re going to find the students are going to rise to the challenge. I can’t wait to hear how that works. I definitely want to be in touch with you afterwards to find out how it goes. Maybe we can have you back to talk about that experience with it.
Rich: Love to.
Anand: One thing we were talking about a little when I met with you — you weren’t really designing this program to be AI-intensive, but it seems like it really prepares those students for the use of AI, or for an AI world. Can you speak to that a little? How do you think it prepares them for a world where they’re going to have to use AI, and AI is changing so many of their jobs?
Rich: Yeah. So maybe what you’re speaking to is — I think you and I discussed — the smartest minds in our country right now are talking about a future where in three to five years, two-thirds of all white-collar jobs may be eliminated. And I think a lot of blue-collar jobs are going to go with it. I think they just think of white-collar jobs as being easier to automate, and they’re in the white-collar sector, so they concern themselves with white-collar business. But I think blue-collar jobs are right behind them.
What does that world look like? I think we’re going to move away from the current environment, where you graduate college, you try to find a career you can settle into for 45 years and make a long haul of it. I think we’re moving toward an economy of problem-solving. If it can be automated, it will be automated. So if you want to do something with your life, if you want to find value, you’re going to have to go find a problem to solve. Our SLA is structured around finding problems to solve and going out and leading people to fix those problems.
Chapter 5: Leadership
Don: You mention a lot of going to the battlefield and thinking about some great historical military examples to highlight this. I think some people in society — especially those who haven’t had any military background or family members in the military — kind of view that as separate from leadership in the rest of society. Obviously it’s not. But I’d love to hear you speak a little about that. How is it that the leadership skills, and learning about it from those that were in the military, veterans, or thinking about military experiences — how can we draw on those and have students draw on that, even if they’re not going to go into the military? What are the similarities between the two?
Rich: I think military leadership kind of gets a bad rap, in that it’s viewed as if there’s this commander or drill instructor who stands on a soapbox and barks down at people, gets in their face and yells at them and tells them how to do things — when in reality, the leadership I experienced in the military was all about serving those at the bottom. If I’m a corporal and I’m in charge of lance corporals and below, how do I best enable them to be better at their job and to achieve the mission?
One of the things I think industry has yet to learn from the military, especially the infantry, is — we’re really good at training everyone below you to be able to immediately step into your position and take over your job, because you may be the first one to get shot when things hit the fan. Sorry, I need to consider your audience. I’ll try to censor myself. We’re really good at that. But I think in industry, it’s much easier to find what I’d consider a gatekeeper — “I need to be the only one who can do my job to the best of their ability, and I need to be indispensable, or I’ll be easily replaced.“ I would challenge industry to say: look for the people who are actively trying to replace themselves with their subordinates. Those are the people you need to promote, because those are the people making sure everyone is capable of progressing. Military leadership at its heart is: leaders eat last. I need to take care of everyone in my charge and make sure they’re best enabled to achieve whatever the mission is today.
Stefan: One thing I’ve been thinking about a lot lately is that education can be very self-referential. I can create a content goal or a skills goal, and then we can see how many students met it — the whole system can kind of reference itself. In industry, you can’t really do that, because you have to compete against other companies. In the military, the stakes are even higher — they’re more existential in many ways. Now that you’ve been in the military and you have two of your own businesses, what are some things you think education can learn from either or both — business or the military — in terms of how we should prepare students for the future? I’m sure you reflect on what your own daughter is learning at school and how she’s learning, and you might reflect on that a bit.
Rich: That’s a big question. I think education is always going to be kind of handicapped, because the timeline it takes to get from what industry needs, and what industry is doing well, into the curriculum — and then to prepare students for that — especially as things change quickly… I think we talked about the OODA loop. It was Colonel Boyd who created the OODA loop, an acronym for Observe, Orient, Decide, and Act. He was an Air Force colonel teaching dogfights. If you have two airplanes in the air actively trying to defeat one another, the one who can observe the enemy, orient, decide to pull the trigger, and pull the trigger to eliminate their foe as quickly as possible — the one who can do it first wins.
He then applied that and said: we do thousands of these OODA loops every day in every part of our lives. The better you get at executing that loop, and at preventing people from interrupting yours, or the better you get at interrupting your opponent’s, the more effective you’re going to be. The problem we’re all facing with AI is that loop is getting tighter and tighter, and it’s difficult to keep up with.
Chapter 6: Learning with AI
Rich: Industry is going to change very rapidly over the next couple of years, and I don’t know how education can keep up with it. I don’t know if it’s possible to keep up with it in its current form. I’d pose the question back to you: how do you keep up with something so advanced? Government can’t do it in any way, shape, or form, and school is regulated by government. How do you take the lead and stay in front of that ship? I don’t know.
Stefan: It even goes back to your summer program — people, whether through the nonprofit or for-profit sector, offering students ways to learn outside of school. A lot of students are taking advantage of those opportunities in other ways. I think students have started just learning things online. I’ve had a couple of students where I am now who learned a lot about AI — they taught themselves both the math behind some of the models and some computer-science things. That’s probably not the average student, but there are a lot of opportunities to learn more than you need.
I don’t think schools are going to be able to provide all the instruction. I don’t think most faculty are going to learn that quickly at either the K–12 or university level. But to really make those resources available to students — encourage them to take classes on Coursera, or even just find things online where they can learn… I think the one thing schools can do that they’re not doing — that they’re almost afraid to do — is to tell students, “The world’s changing a lot. We can’t teach you everything you need to know. You’re going to have to take more responsibility.” Schools, especially K–12, are so protective of the kids, trying to make them do things, which is okay, but that’s not really going to be enough. I think schools could really empower students more than they are. Sometimes they’re almost disempowering them, saying, “Just do exactly what we tell you and you’re going to be set.” I don’t know how anyone can say that.
Rich: Yeah. I think if the schools have any duty to the student, it’s to teach root principles and instill a sense of judgment. You can create anything with AI, and you can even ask it for five solutions to the same problem — but knowing which of those solutions is the best, that’s a skill that’s going to have to be taught, or it’s useless.
Stefan: I think that’s an incredibly important point, Rich. That’s something we’ve talked a bit about in other interviews and episodes, but most people in education don’t get that. It’s changing — there are some who are still resistant and thinking we can just hold off AI, and that’s not realistic, obviously.
Don: Yeah. I mean — why would they want to?
Stefan: But for many others, to appreciate this role of judgment… I think we’ve always thought we were teaching some of that, but it’s back to your example of the OODA loop — it’s happening so much faster, and that level of judgment has got to be so much more specific and more sophisticated than ever before. When I think about evaluating somebody’s arguments — if somebody made a claim, if we’re having a discussion about politics, the arguments we would have made a generation ago would probably be fairly basic. Now we have access to so much more information; things are far more sophisticated. Not only do I need to understand that argument, I need to be able to judge it in a more sophisticated way, evaluate it in a more sophisticated way. I think that’s where we’re falling behind — we’re still looking at it through the old lens.
Rich: Are you suggesting that critical thinking is important to know? It just might be.
Anand: This is something we’ve been on a soapbox about for a long time, because we both have a debate background. If you don’t have critical thinking, I don’t know how you survive in this society. You’re just going to be taken advantage of left and right.
Rich: I really appreciate Elon Musk’s stance on this whole subject — that he started very pessimistic, very doomer, saying this is not something we are ready for, not something we should be actively developing, and we need to pump the brakes. And then it wasn’t long after that that he came out and said, “You know, the genie’s out of the bottle. You can either participate or spectate. So I’m choosing to participate.” And in that — I’m obviously inserting my own thought process here — he’s saying the genie is out of the bottle. It’s up to us to decide whether that genie looks like Robin Williams or more like Jafar. The duty of our educators right now is: how do we make sure we’re producing students who want to create things that look like Robin Williams and not Jafar?
Chapter 7: Process Over Product: Rethinking Student Assessment
Anand: When you’re thinking about your own — I love a good Aladdin reference; you can tell somebody has a kid, they’ve watched that movie a number of times — when you’re thinking about your own daughter…
Rich: The OG Aladdin, right? Not the live.
Anand: Yeah. What do you want your daughter to develop as far as these skill sets? That’s the hard part. I have kids in public schools too, and they have to play the game — there are still things you have to do — but I’m also like, “Okay, this is what you really need. This is what you really need to be able to do.” How are you guiding that for your own child?
Rich: Yeah. Again, spectate or participate — and I’m choosing to participate as much as possible. We both have full schedules at the moment, and so we get a little bit of time in the evening and in the mornings. I’m very grateful that I’m fortunate enough to be a parent who can take my daughter to school and pick her up from school and have conversations around that. This summer I’m planning to give her her own AI agent, and sit down with her and — as we talked about over coffee — set it up in a way that not only doesn’t spend a ton of money on tokens, but doing all the work to dictate or direct the personality and the values of that agent to produce useful and meaningful things. We’re going to sit down this summer shoulder-to-shoulder and build her an AI agent — or ecosystem, or whatever it looks like. We’re going to learn a lot of it together, I’m sure, because by then things will be different and I’ll have to relearn things. Active participation is the best thing you can do as a parent, and that’s what I’m choosing to do.
Stefan: I’d love to be a fly on the wall on her first day back to school, and you know, sometimes a teacher says, “Hey, everybody, say what you did over the summer.” And your daughter says, “My dad built me an AI agent to do all my schoolwork.”
Rich: Well, that’s okay. Remember — I’m a military veteran and a bodyguard by trade. My biggest concern going into kindergarten was that she was going to tell her teacher that I hide guns and money in the walls. So I think we’ve progressed a little further. I think this is a safer topic for her to talk to her teacher about. That’s fine. Yeah, I think so. Maybe.
Anand: What I love about that example, though, is it’s not just “Yeah, kids are going to have AI, let them have AI.” It’s playing an active role in then guiding what your daughter’s going to do with AI, helping her build it, talking to her about it, and letting her see your process for building it out. One thing you told me about, with what you’ve done with your OpenClaw, is training it on certain materials so that it gains a particular perspective. Tell us a little bit about that. What went into that? Why do you think it’s important for that agent to have a particular perspective? This is something we’ve talked a lot about — what we call AI pluralism — this idea that every human obviously has a different perspective, AI is going to have a different perspective. This really resonated with me. Tell us a little bit about what went into it and why you did it.
Rich: Yeah, I’ve kind of created my own little internal LLM for my agents. I’ve downloaded ebooks and PDFs of what I think is important work, and the things that shape my mindset — therefore I wanted to shape the mindset of my agents who work for me. That’s a whole lot of books on leadership, from Jocko Willink, Jordan Peterson, military generals throughout history. The very foundation was the Stoics — my agent is called Marcus, because Marcus Aurelius was a layup for me — and the disciples.
You can see it in a lot of the content we produce — it’ll very often reference the Stoics, or the disciples, or Jocko Willink. Because that’s the information that has developed my brain, it’s also the information I wanted to put into my agent. I think that revolves around a conversation we had — if the next iPhone doesn’t have an agentic AI platform built into it that is shaped and developed around the information they’ve already gathered on you as their user, they’ve missed the off-ramp completely. These big data users have gathered so much information — as we talked about, if you have Tinder installed on your phone for a week, how much information they’ve gathered on you, about when you’re lonely and when to serve you different types of ads — if they don’t start using that to actively develop your own agent for you, that’s a huge missed opportunity.
Anand: So are you thinking about helping your daughter to train her agent in a similar way — to take some of her favorite books or materials? What I love about that is — it would be highly egocentric of me to think that my daughter wants to learn from the Stoics, but…
Rich: Yeah, I think there’s some of it in there. I want her to have the same idea as I do.
Stefan: I mean, hers might be train on Diary of a Wimpy Kid or something — whatever she feels is important. I love that idea of imprinting yourself on it so that it better represents you as the user.
Rich: Absolutely. It’s kind of like the quote, “If you don’t define success for yourself, others will define it for you.” In the same way, if you don’t tell your agent how you want it to think and what you value, you’re waiting for these companies to do it for you — and I think that’s the wrong approach.
Anand: Yeah — if you don’t imprint yourself, you’re going to be imprinted, right? It’ll gather, like you say, potentially all that information they have on you, and most people don’t understand the totality of it — what they’ve gathered on you for decades. That still may shape, or kind of misunderstand you, at least according to you. Maybe they understand you better than you understand yourself, so to speak. But you want to have an opportunity to influence that — that’s one thing.
Chapter 8: The Service Leadership Academy Model
Stefan: The two other things that stand out to me, as I’ve listened to you talk: one is that now you need to be a continuous learner. It seems like you’ve taught yourself all this stuff on your own. Agents are a new thing; OpenClaw is a new thing. You’ve learned a lot of this on your own. Can you talk about how you went about learning how to build your own agent and use OpenClaw?
Rich: Well, to give a little more context — I think I told this already — I was a freshman in high school reading Rich Dad Poor Dad and books about starting your own business. I was 100% drinking the Robert Kiyosaki Kool-Aid, and I wanted to own the cash-printing machine. I didn’t want to be a part of someone else’s machine. Then as a sophomore, a couple of guys flew airplanes into the World Trade Center, and I could not join someone else’s machine fast enough. I enlisted in the Marine Corps the day after my 17th birthday, and I left for boot camp four days after high school graduation.
I spent eight years in the Marine Corps. I was diagnosed with traumatic brain injury as a result of an IED about three and a half years before I got out of the Marine Corps. I started my first business two years before I got out. They had told me at the time that I was doing well teaching student lieutenants, and so they were going to allow me to continue to do that, but they didn’t see me going back to the fleet and leading troops in combat with my brain injury. So I had to make a huge adjustment. I had to pivot, and I started having ideas about being a business owner again.
Backing up a little — as a freshman, I think I probably had a 4.0 GPA. Then I joined the Marine Corps, and I knew all I had to do was get a certificate, get that diploma, and I’d be fine. So I spent all my time from that point forward focusing on sports and girls. About the only thing I have in common with Patrick Bet-David, other than some of our values, is that we both graduated high school with a 1.8 GPA. I have gone back to school — I’ve done the community college route, and I used a bunch of my GI Bill to go to professional schools like Executive Security International out in Colorado. So I definitely view the importance of knowledge and education. I don’t necessarily agree with how it’s being delivered nowadays.
Rich: By the time I adopted OpenClaw — to get back to the root of your question — there was already way too much information on YouTube. I get most of the information I need to do the things I want to do either from YouTube or from the AI itself. You can learn a lot about how to use AI by asking AI how to use AI, and having it teach you. Now, it’s in a vacuum — it’s going to tell you based on what else is out there. But I think the combination of the two for me, whether it’s YouTube or X or asking AI, has done well to teach me what I need to know. And I tell you what — refining AI production by having a different AI check the work of the predominant AI you’re using produces pretty good results.
Don: It does. Yeah. It’s just really incredible how AI can teach you so many things. There are so many ways to learn. It’s kind of a theme I’ve picked up on. Sometimes it doesn’t go over well with educators, but I’ll say: ask your students what some ways they learn are besides in the classroom. Even just regular school math or whatever — they can get it from the teacher, they can go on YouTube, they can ask the AI; some kids have tutors. We get upset when kids aren’t paying attention in class, but it’s not the only place they can learn content. In some instances, it’s not the easiest place for them to learn. There are so many opportunities to learn and grow and build businesses. It can be a little scary — you’ve got people losing jobs, and you need to be aware of hallucinations — but you can do the same thing with an AI agent that you can with a student, and say, “Show me your work. Show me the citation.”
Anand: This sense of being able to learn in other places — we’ve got to lean into that. So much of the traditional educational approach is that the classroom is this sacred place. Stefan and I are educators, so we have drunk that Kool-Aid before — but we also, I think, realized as debate coaches, and from our experience in debate, that I learned a lot more from debate than I ever did in a classroom. Because I was motivated. I wanted to win that debate. I wanted to make sure that I didn’t look like an idiot when I was in the middle of a debate. So you find other ways to learn. We’ve got to find a way for students to be motivated to learn like that.
Rich, if you could speak to most — let’s say K–12 educators or higher ed — what would you tell educators about how do they make that pivot? It’s not easy when you’ve been doing something for a long time the same way and you realize, “Hey, things have to change.” I’m not sure how to change. What would you say they should start with?
Rich: Well — you brought up debate. One of my favorite debaters is Dennis Prager. I don’t know if you’re familiar. He’s a conservative Jewish debater. He owns an organization called Prager University; the YouTube is PragerU. He will tell you that the reason he often gets invited to debate in circles that a lot of other conservatives don’t — or anyone who challenges the view of the people in that circle — is because he doesn’t seek to win the debate, necessarily. Anytime he’s on a debate stage, he certainly doesn’t look for gotcha moments, but he doesn’t necessarily look to win the argument so much as to better understand the person he’s debating against.
If he can better understand what’s brought them to the conclusions they have, and what’s driving their thought processes — whether he wins or loses, that’s a better state at the end of the debate. With every single student, if you seek to better understand what’s driving them to where they are, how they got to the conclusions they have, and then use that to better influence them and better educate them, I think you’re going to be light-years ahead of where you started.
Stefan: And talk about creating a space where the students are going to feel valued. That’s a great approach.
I’ve really enjoyed this conversation, just thinking so far outside the box. You talk about how your educational pathway was not traditional — some educators may look down on it and say, “Well, this person graduated from high school with less than a 2.0” — but you’re talking about project-based learning, you’re having educational programs for students, you talk about your own learning path. It’s a lifelong learning, and having agency, and developing businesses. A lot of students who go through the traditional pathways are not going to end up there, and they’re not going to end up with the skills they need to succeed — not just in this new world, but to some degree as in previous worlds, too.
Rich: Maybe — maybe as we get students through the program, and we’ve graduated a handful of them, I can start branding myself as the heretical educator.
Stefan: That’s awesome. That’s awesome.
Chapter 9: Preparing Students for an AI-Driven Economy of Problem Solving
Don: I know — we met on LinkedIn, and that’s where a lot of this conversation happens. It is project-based learning, and he’s doing this pretty well, but he’s just working so hard to get schools to do it on a really limited basis — like a special thing in the class — and you’ve come up with it, and you’ve taught yourself all this stuff, and you designed the program and thought through all the iterations of it, like you said, with an AI. It’s really awesome. It’s just a demonstration of not just doing well, but — like you said, you could take this powerful AI and you could basically do good or bad with it. You’re doing good with it.
Rich: I appreciate that.
Stefan: I’m really excited about the summer program, and I definitely want to follow up with you to find out how it’s going, because that’s exactly the kind of education students need. When we were talking a little earlier in the conversation about the problem with more traditional approaches — somebody going and getting a degree takes years, and even a course will take so long when you need the skills now. We have to find ways for education to adapt, or maybe for traditional education to get out of the way for people to be able to develop those skills. If you waited and said, “Hey, I heard about OpenClaw — I think I’ll sign up for a class next fall to learn about OpenClaw,” and then maybe by December there would have been a class about it, at that point OpenClaw is not even going to be around. Things will change so rapidly. It’s just laughable to think about a traditional educational process working with something that’s changing that quickly.
Anand: There are some areas — I still want to have a doctor that’s gone through a lot of training. You’re right, root principles matter. But for most of us, when we’re thinking about these skill sets, we’ve got to find ways for students to be motivated to go and learn it right away. It’s got to be just in time, and it’s going to come down to their motivation. That’s one thing I love about what you’ve outlined — giving students that agency and that motivation is key. I think you have a great way for them to develop that.
Rich: Well, I want you to think about the words you just chose. You said, “I want a doctor that’s had a lot of training.” And we’re getting very close to having AI models that have far more training than any human can get in a 20-year education. So — I think we agreed — the future is equal parts exciting and terrifying. It’s going to be a hell of a ride.
Stefan: That it is. That it is.
Anand: If you don’t mind, one last question I want to ask you about: I hear often from people that they’re — especially living in Fredericksburg — resistant to AI because of data centers. They don’t want AI to displace their jobs. They just want to put up roadblocks. What do you say to them? How do you get people to appreciate that maybe we need to take a different approach?
Rich: I would say: keep up. The data center problem — by the time we’re done arguing about it, Elon will have data centers in space, and it won’t be something to argue about anymore. It was the same thing we saw in the ‘90s and early 2000s, when Congress couldn’t come to an agreement about whether we should be cloning sheep, or using stem cells from fetal material to study DNA. They couldn’t finish having the argument and come to a consensus before science came back and said, “Yeah, we don’t need that anymore.” So the thing is — you can either keep up, or get left in the dust, because there’s really no alternative.
Stefan: It’s hard to find something more powerful to end on. What a great — you should open a keynote at a university. That can be your opening line. Very serious.
Rich: I’ll do that one on pay-per-view, you know.
Anand: Rich, what Stefan’s saying is — you’re among kindred spirits here. We’re all on the same page on this, and our worry is that people aren’t going to keep up, and we’re mostly worried about our students. We’ve got to find a way for them to keep up and be given these opportunities. That’s one of the reasons I’m so excited about your program this summer — because even if you never even mention AI, those students are going to be better prepared for an AI world than most other student experiences they would have. So I applaud that, and I encourage you to keep building that.
Stefan: Reverse education. They’re being told, like, “Don’t keep up, don’t do this” — it’s kind of the opposite of what they mean.
Chapter 10: What Education Can Learn from Military Leadership
Rich: I don’t know how much more time you have, but I want to give you a real quick, bigger view of what we are doing. The SLA — the Service Leadership Academy — is one aspect of what the Guideon Foundation is doing. The Ronin Leadership Activation Program — there’s kind of a huge big picture here.
Rich: Veterans are committing suicide at a rate of 22 per day. There’s another whole number of veterans who are going homeless every day. It’s a misconception that that’s all due to combat trauma and PTSD — that’s a misconception, because most of them haven’t been seeing combat. So why are they removing themselves from society? I think it’s because we’re not preparing them for the huge transition that takes place when you go from wearing the uniform and having a certain amount of reverence — but also having a built-in purpose and identity that goes along with that uniform. You never question your purpose or your tribe while you’re in uniform. Then to separate from that tribe and have to struggle to figure out who you are and what your worth is, because you’ve been tying your entire self-worth up in what you do for a living for the last four to 30 years — that’s a very difficult transition to make.
Rich: I only recently realized that veterans and stay-at-home moms who are empty-nesters have a very strong connection. They’ve tied their entire identity to this one job they do for the last 20 years, and now that job doesn’t exist. So how do you find value in yourself?
I say all this because — it’s kind of like the LA wildfires. The dumbest thing about the LA wildfires was that we had these wildfires that were wrecking people’s livelihoods, and we had this huge reservoir of water to put out those fires with — that we refused to touch. We had the problem right there, and we refused to use the solution to solve the problem. More recently, we had 500 tons of food in Africa that was paid for by American taxpayers to feed the poor in Africa, and we destroyed all that food because of bureaucracy. We had the solution, and we chose not to use it to solve the problem.
Rich: Again — we’ve got veterans throughout this country who have millions of dollars and countless hours in training to be leaders. And we have a nation that’s starving for leadership. So why not use those veterans to solve that problem? And if we have two-thirds of all people having to go through the same transition in the next three to five years — where now they’re struggling to find identity because the career they’ve had for 20 years is completely gone because of AI and robotics — well, they’re going to be going through that struggle too. So what the Guideon Foundation is hoping to do is to get veterans in a position to better help the rest of our population, who very soon is going to be saying, “What value do I have in myself if my career doesn’t exist anymore?”
Stefan: That is really powerful, and I think you’re right. It’s a tragedy that veterans are experiencing this, so it’s important to address that. But you’ve tapped into something much bigger. This is going to be a transition that will affect so many people, that if you’re able to work on this, it could benefit so many sectors of society.
Rich: Yeah. Equal parts terrifying and exciting.
Anand: More of an emphasis on terrifying for some of us. But it’s exciting to see you working on this, and it’s really great that you’re giving your time to work in these areas.
Rich: Well, it’s the one way I’ve found to try to be useful.
Stefan: Thank you, Rich. Thanks so much for being part of this. If somebody wants to find out more about the Guideon Foundation, how can they find you or the foundation’s materials?
Rich: Sure. guideonfoundation.com — guideonfoundation, no spaces, no periods, nothing. On Instagram, Facebook, YouTube — all the places.
Anand: Rich, thanks for joining us. We’re going to follow up. We want to hear more about what happens this summer, and as I said before, I want to bring you on campus for some discussions. I think a panel discussion with local business people about how they’re using AI would be so valuable for our students, and to be able to share what you’re doing with the Guideon Foundation. I think that’d be great.
Rich: However and wherever we follow up, I’m already looking forward to it.
Anand: Excellent. Hey, thanks so much.
Rich: Thank you.