In this revealing episode, Caleb shares gratitude for how Rich Dad, Poor Dad shaped his financial journey from humble beginnings to founding BetterWealth. He recounts meeting Robert Kiyosaki at a Tax-Free Wealth event hosted by Tom Wheelwright, reflects on Kiyosaki’s bold opinions including his thoughts on Dave Ramsey, and explores their contrasting philosophies. Caleb also opens up about evolving perspectives on life insurance and debt, practical advice for young investors, and his vision to bridge financial ideologies for greater impact.
"All coins have three sides. Wisdom is being able to see both sides." – Robert Kiyosaki
The full transcript of this insightful conversation follows below.
All right, so some of you guys have been following me on other platforms like LinkedIn, Instagram, even YouTube has a community function, and you may have seen a picture with me and Robert Kiyosaki. Recently, I had the opportunity to speak at my friend Tom Wheelwright's event, and he's like one of the most famous CPAs, wrote the Tax-Free Wealth. He's also very well known as being Robert Kiyosaki's CPA, and I had the opportunity to connect with Robert during that time, And it was actually my first time. meeting Robert. And I know that Robert, just like any public figure out there that speaks and all, there's many people that can clip him. He said some things that maybe I wouldn't necessarily 100% agree with. But overall, he's like the goat when it comes to entrepreneurial way of thinking about money. And I think many people, including myself, are aware I am because of books like Rich Dad, Poor Dad. And so what I had the opportunity to do is I got to... share my gratitude. And anytime I meet someone like Robert, my initial reaction is to say, listen, I don't want to necessarily leverage this time for me to gain. I just want to take time to say thank you. And so I just let him know. I said, hey, Robert, my name's Caleb. I run a company right now helping people with money. And I just want you to know that at 16 years old, my dad gave me your book. It was either 15 or 16. He gave me your book. And that book, I remember listening to that book. And again, I've read lots of incredible books. And I think early on in my life, a book meant more. It was like sometimes the first time you hear something, it's like the most powerful. So you could hear it over and over and over again. But it was like that first epiphany. And I think the way that Rich Dad, Poor Dad was written. So many people, including myself, could resonate with the takeaway of like, man, like that was big. And I just got to share with him like I am doing what I'm doing because I read that book. And it's true because when I was working at the chicken farm, for those of you that know my story, I was working at a chicken farm. I was gutting chickens. I was making a dollar for every chicken that I processed. And Rich Dad, Poor Dad was one of the first books I read along with Richest Man in Babylon and Good to Great by Jim Collins. Those are like... three books that were really pivotal in my life. And through that time, I got a job at a bank. And I had opportunities to make more money working at different companies. And I chose to work at the bank, made $8 an hour for almost until I left the bank, $8 an hour. And I got to learn in our investment department. I got to do marketing. I got to do other things. A lot of people, including people who love me a lot, said, Caleb, you could go make more money at State Farm and other things, and there's nothing wrong with State Farm, but I was very clear to me that I was not there at the bank to make money. I was there to learn skills. That was one of the things that I took away from Rich Dad, Poor Dad. And then just the other aspect of the overarching you're not free until you have enough cash flow to fulfill your expenses and the idea of an asset. And there's those aspects that, again, like... It's not like, yeah, was Robert the first one that shared that? Maybe, but it was the first time that it really stuck in my head. And so overall, it's those frameworks that were key. And then I remember playing Cashflow as a game, and that was really instrumental in my life. So I got to share all of this with him, and he was really gracious. And he's like, he was just, what impressed me so much about him, because he spent, he's sold. think over 21 million copies you can fact check me on that but i think he sold a crazy ton of copies and he hears store like he probably hears from so many people and yet he took the time to listen and i was it was just really really special and so that that was our interaction and then i you know sat down at the table with him and we were having interactions and the the subject of of of Dave Ramsey came up and, you know, Robert had some choice words to say. If you know Robert, if you've seen some of his videos, you know that he doesn't give a crap. I think that's a very fair term to use at this point. He doesn't give a crap about what people think. He's just going to say what he's going to say. And he said some words that I'm not going to repeat on this channel about Dave Ramsey. And I said, hey, Robert, one of the things I didn't mention, but I actually have a small YouTube channel. And if I could host a debate between you and Dave, would you be down? And he like, before I could even finish, he's like a hundred percent. And he's like, you can use my name as well. Get Dave Ramsey on let's, let's have a debate and a discussion. And do I think that's possible? If I'm being honest, no, that's not even the. the thing that I would necessarily go for at this point. If I can get Robert on the show and have a sit down interview, and if I could have a sit down interview with Dave Ramsey, that I would much rather prefer those two. And then if, if I have a good conversations with both and build up credibility with both of them, could I sit down and host that? Like, that would be incredible. I think we would have to do some type of like charity. Like, I don't know. We would get creative. I think we could raise money for charities. have a great time. Would Dave Ramsey change any of his opinions? No. Would Robert Kiyosaki change any of his opinions? No. But it would be it would get a lot of clicks. And I would I think it would take my channel to the next level. So I'd be like my selfish plug to why I would love to do that. Well, anyways, he he shared that. And then we talked about lots of other things. And, you know, I asked him about crypto and his thoughts around that. And one of the questions that I love. asking anyone that I admire, I would ask the same thing today, Dave Ramsey, or anyone that I, that I interact with, that I respect what they've built or what they stand for is I essentially am like, okay, if you were my age, or if you were had to tell your 20 year old self, um, one thing, what would it be? And the reason I, the reason I do that is it's, it's a powerful question because all the things that you've learned, you know, there's, there's a hierarchy. And a lot of times, if you ask something like that, You just go to like what is the first principle? What's the thing in my life that I would go back to to say this is it? It's just a question that has served me well. If you could go back in time and tell yourself one thing or what's the biggest mistakes that you've made or the regret? Like those are those are the questions I like asking because they just I just, you know, I get the heart of the matter. And Robert said he said all coins. have three sides. All coins have three sides. That's what he said. It actually reminded me a little bit of when I spoke with Arnelson Nash before passing. You know, I would ask him a question and he would never give me like a direct like, here's a bullet point number one, here's a bullet point number two. He'd usually give me something that I would have to like chew on. And all coins have three sides. And it's interesting because it's true. The side that a coin would probably never land on, I guess if you flipped it a billion times, it probably would land on the corner maybe once or twice, but pretty much statistically impossible. But it is true. It's like you have two main sides and then you have the corner. And Robert said, wisdom is being able to see both sides. And I admire that. I appreciate that. I agree with that because When I look at early on in my life, especially learning about life insurance and writing the AND asset, which I have no copies of it right here. No, I don't have any copies of it here. When I wrote the AND asset, I literally thought this was going to change everyone's life. I really did. And sometimes being naive is a blessing. And I was just like, man, if life insurance could change the directory of people's lives and the nation. if everyone bought life insurance you could make the argument that these social programs would go away and you you could make the argument of that but i think it was just like i was young and i just like i just wanted to share the world like this is this is the best thing in the world and i didn't try i wasn't i didn't have ill intentions but when i look back on even my book the and asset when i look back at some of my first videos i very much was one-sided and it you could tell and And the part of that makes me cringe. And as I've learned, as I've grown older and more experienced and hopefully more wiser, I've realized that more of my stances are just not 100 percent right. And I'm actually uncomfortable in saying that. I don't think everyone should buy permanent life insurance. And it's like, well, Caleb, that's a big part of your business. Yeah, I think a fraction of the population should actually. do the thing that i represent and that doesn't make it a scam but that doesn't make it right for everybody and i wouldn't have said that earlier on um and i would have thought that statement alone was like a sellout like uh um you know you're you're you're selling yourself short or you're not believing or you're lacking conviction and it's like no actually life is a lot more complex and my views on a lot of things have just mellowed out a little bit but But what I, what I. tell people is my conviction has grown even more. Like my conviction around people having life insurance has grown and yet I've been less hypey. It's like, how is that possible? It's like, well, I'm number one when I learned, let's just take the life insurance as an example. I was just fixated just on the ability that my cash value was growing and I could use it. And now I look at that and go, well. If it was just those two components, growth and borrowing against something that could grow, you're actually better off putting your money in a high yield savings account, withdrawing that money and putting that back in. From a mathematical perspective, in most cases, you're way better off with that. So it's like that would have been like I would have been triggered seven years ago if I was like, well, you're not wrong. Like you're wrong. It's compounding and blah, blah, blah. And yet, no, I'm right. And yet why do I still proponent of life insurance is because there's things that I just didn't value at all that i value way more now like the death benefit like other benefits that all together i would argue i would argue that you would be better off having that asset using the borrowing function than using a high yield saves account or a bond and all and that's that's where it's like less hypey but more convicted that's that that that's that aspect and so you can look at that in almost any um place i've seen a lot of people that were like really big into real estate Like the Real estate is the solution. That's quite frankly one of the reasons. I think that would probably be one of the negatives of if I had to pick any negatives of like the Rich Dad book is a lot of people read this. He used real estate as an example, and a lot of people are like real estate is the answer. Real estate is the solution. I just talked to entrepreneurs, successful entrepreneurs that they were like they're like getting out of their business, and they want to do real estate, and yet their track record in real estate is really poor. Why? Because they're not real estate. people, they're entrepreneurs, and yet they want to be real estate moguls. And I'm not, I'm nothing against real estate. That's just that, that's the example of, it's, it's not that easy. It's not, you can't just say like, this is a solution. And so that would be like the critique on the other side is, you know, Robert Kiyosaki is a big fan of debt. And yet you could, you could have case study after case study of case study of how using debt made you worse off because you you know weren't investing in underlying assets or you were being done with it or you weren't doing proper underwriting and all and so is The debt the issue or is the investment the issue and the same thing with Dave Ramsey and Dave Ramsey is like so strong on Certain aspects Dave Ramsey's asked if you were given Bitcoin He wouldn't accept it because he'd be hypocritical Robert Kiyosaki told me that free like pre the internet He had a professor that he was talking with that was talking about the function of Bitcoin And that was when he was like that's gonna be Genius and so he was an early adapter to Bitcoin that would be an interesting conversation to have obviously debt Would be interesting we I talked to Robert about the idea of the Federal Reserve and the how our dollars say their Federal Reserve Note so even the people that are pro cash are using debt instruments by paying cash That would be an interesting conversation with Dave Ramsey not sure their stances on life insurance. I didn't ask Robert Kiyosaki stance. I think he's he's probably neutral i i know that he knows people that are life insurance i know i've heard i've never heard it from him directly i've heard it indirectly that you know he's a fan of the concept of what we use but not as like the underlying place or investment not sure if that's true or not that would be something i would ask him if i had the opportunity to sit down but i also would be super fascinated with how his thoughts around education i mean i i have a daughter and i'm curious if robert had to go back What would he teach and how would he teach? What would be those aspects that he would share? If he had to rewrite Rich Dad, Poor Dad or take out one chapter or add one thing, what would he add? Does he have regrets? I know that he's had, like any successful person, he's had lawsuits in his past and all. What did he learn from all that? And, you know, nearing as you get older, like as you reflect back, what would be the things that you would change? And one of the things that you're, you know, dialed in and more convicted than others. So I would just say if anyone's in Dave Ramsey's camp watching this, and if anyone's in the Robert Kiyosaki's camp that are watching this, just know my heart. Just know like that is something that I would love to do. And we don't have unlimited time. Neither Dave or Robert are spring chickens. And I, so I feel the gravity of that and I want to be able to take advantage of that. in due time. One of the, one of the things that I'm going to end with is how, what, what are going to be the next steps? Well, I, there's someone told me that I should get a, a billboard outside of Dave Ramsey's office that says something and, you know, egg him on. I'm not going to do that. I'm not going to do that. Um, I don't, I think it could be potentially good marketing, but it's like how to, how to not win friends and influence people. Who am I? I'm, I'm not going to try to be a punk and. I live 30 minutes away. Could I go and do something crazy at their office and get attention? Maybe I'm just not going to do that. That's not how I roll. What I'm what I'm going to do is I'm I'm working on a gift for Robert Kiyosaki and I'm working on a gift for Dave Ramsey. I'll keep you guys in the loop with how that goes. And I would love to give. give them that and invite them on the show and not as a bribery, but just as a, hey, thank you. And at any time I'll drop what I'm doing, fly to you and in Dave Ramsey's case, drive to you and host a sit down. And so that's the thought process. I'll keep you in the loop. I think regardless, I think there's a lot that you can learn on this journey of even how we're going to gift. I think there's a lot that you can learn by the route that we're going. And I will say I've in the past, I've reached out to the Ramsey team. I've tried to get George Camel on the show and been turned down at this time. But that might change as well. And so anyways, that is that is the thought process. And again, I just want to thank you all for being a part of my story, a part of this journey. And this is a unique video, but I just wanted to be real and just share some of the exciting things that are going on. And sometimes I have to pinch myself because when I first started, I literally made videos just so I wouldn't have to repeat the same thing over and over. And now some of our videos are getting over a thousand views, which are insane. YouTube's paying us because people are watching our videos, which are insane. And we're getting clients almost every day from this channel. I never would have thought this would have been possible. The purpose of this video is to let you know, like. I just want to thank you. This is like a non-traditional video of me just kind of reflecting on some of the things that I've learned and some of where we're going. And I just want you to know that this would not be possible if it wasn't for you. This would not be possible if it wasn't for those of you that have trusted us and then clients of Better Wealth and those of you that subscribe and like our videos and for those of you that share this content. Like we just I wouldn't even have the ability to have Robert Kiyosaki say I'll do the debate if we didn't have a platform. And I wouldn't even have been at this event speaking if it wasn't for the people that have entrusted us and helped us get to where we are. So from the bottom of my heart, I want to say thank you. And if you're watching this and you're like, I want to learn more about how we can be part of what we're doing at Better Wealth, we'll have links down below. You can follow those links on whatever resonates with you. And we want to be able to serve you. So thank you. Subscribe for more videos. And we'll see you next time.