How Did He Retire Twice Before 40?

Ready to start working for your money and start living life on your own terms? In this no holes barred episode of Keeping It Real on Purpose, I'm joined by Chris Miles, the cash flow expert and founder of Money Ripples. I love the word ripples. By age 39, Chris had already retired twice and now is showing highincome earners how to escape the grind, unlock hidden cash flow, and build true financial freedom without relying on Wall Street's rules. Chris has been featured in CNN Money, Bigger Pockets. I used to belong to them. Yeah. Entrepreneurs on fire. But today, he's here to shatter the myths you've been told about money, wealth, and success. If you're tired of the traditional financial gain and ready to create a life that aligns with your purpose, this episode is for you and it's going to blow your mind. Welcome to the show, Chris. Thank you so much for having me today. I'm excited to have you. I I love talking about money. Love it. And money is a good thing. We like it. It's a good thing. So, you retired twice by age 39. What does that say about the system we've been taught to believe about work and money? And is it a lie? Yeah. You know, it definitely is a lie. I'll tell you the reason I did it twice because people are always impressed like how'd you do it twice by time you're 39. The simple answer is I screwed up the first time. That's how I did it twice. It should have only been one time, but I screwed up the first time. So, I had to do it again, right? Um, kind of give you a little bit more that backstory. Um, I actually started out in my as I was going into my entrepreneur journey. I was actually planning to become a business consultant, but I figured I should have real life business experience if I'm going to tell people what to do with their business. So, I actually dropped out of college, started trying to gain some experience, and I ended up my first business that I got into was being a financial adviser, you know, and it was pretty easy to become a financial adviser. All I had to do is not kill somebody or not steal from a bank and pass the test with at least 70% and you're in, you know, and and that's what I did for four years. And then after four years, what happened was uh you know, I I I sat down with my dad. My dad had reached out. He says, "Chris, I'm 61. I've already had heart attacks and strokes. I'm done. I've I've been sacrificing forever." I mean, the guy was like the penny pinching saver. He says frugal. We all say cheap, right? Yes. Yeah. Oh, yeah. Like he was he was like depression era mentality. And so I sat down with him. He had paid off his house totally 100% debtree. He had been stuffing money in his 401k. And yet at the end of that I had to tell him, "Dad, if you want to retire today at 61 years old, you're going to have to die in about five or six years because that's when you're going to run out of money. Right?" He said, "Well, that's not the answer I want to get from my financial advisor. Uh what do I do?" I said, "I don't know. you did everything right from what I teach everybody. So, the only thing I can tell you do is keep saving, keep working, right? Just maybe work into your 70s. And he did unfortunately um to the point where he was he was he's alive but he's not really living if that makes sense, right? Because now the health is sacrificed, you know, he doesn't have all that time anymore. And so, he lost it. And that bothered me. In fact, it bothered me so much that uh eventually I started looking for other answers. And it finally wasn't until I talked to a friend of mine who I trained to be a financial adviser, but then he left my team to go do real estate investing. As we're arguing about what's better, stocks or real estate, he finally just asked me, he's like, "Well, Chris, how many of your clients are financially free where they don't worry about money?" So, well, none of them. They're all like worried about running out of money too soon, even if they're retired. Yeah. Okay. How about this, Chris? How many of you guys' financial advisors are financially free, not off the commissions earning, but actually doing these investments? I said, 'Well, okay, none. There's guys been working here since the 1970s. This is back in 2005, right? I was like, there's guys been working for 30 years in this industry and they're still broke. He said, 'There's your problem. And so, I started to take that Matrix red pill, right? I went to this whole other world of like real estate investing and passive income and realizing I didn't have to be the active investor. I could invest with these guys that were real estate investors and get paid regular stable income off of this. And then next thing you know, one, I quit being a financial adviser because I couldn't teach a lie anymore because I realized it wasn't working. And then two, I realized too is like it's about passive income. Like having income coming in to cover your needs. It's not about how much money you save. It's about what the income that comes off of it is what it really what really matters. And when I did when I realized that, I found out later that next year in 2006, I was 28 years old. I had enough passive income coming in I could quit. And that blew my mind not thinking it was even possible to do that that young and yet I did. Right now of course you know I everyone wants to know how you did it. So in 2007 I came out of out of retirement to teach people how to do how to do what I did. Um got together some partners. We went all in into our business right when the recession hit. And we were focused on real estate investors primarily who were going broke. And so our business was failing. My real estate was starting to fail. Everything was going going up in smoke. Um, I went from millionaire to upside down millionaire where I was over a million dollars in debt after all was said and done with everything going on. And so eventually I was able to dig out that hole in my business. You know, I was able to shift and pivot away from teach about passive income and I started teaching about about how to find money, how to free up cash flow. And as I started to teach that during the recession, then our business started to turn around. It actually pulled us out of bankruptcy. And then that's why I was able to do it twice by the end of 2016 because then eventually launched money ripples and even though despite a divorce and everything in the middle I was still able to come out of it where this time around I was a lot wiser you know I had a lot more investments coming in pay multiple streams of passive income so that I was I was better off and that's where I've been ever since teaching people how to do the same thing. Right. So when you say multiple, is there a number? Because I know there's so many people, oh, you got to have this many, you got to have that many, but is there a limit to the multiples? I don't think there needs to be a limit necessarily. Um, and I think simpler the better. I think you can have too many. Maybe there is a maybe there's a number. Maybe there's too many. It depends on how comfortable you are in your stewardship of that money, right? Some people don't mind having dozens while other people are like, I can't manage more than like five or 10. And that's fine. Um, like in my case, I have about 15 or 16, I think, when I last counted. And so, it's awesome, but at the same time, you know, it's like there's still a stewardship. You have to manage that, right? And so, uh, that's one thing about passive income is that it's never 100% truly passive in the sense that you can just be brain off, never think about your money again. Yes. Let it somewhere and you could ignore it, you know, set and forget it. problem is that's what financial advisors teach you to do and that's why people think you can do that is oh I just said it and forget it but they have you do that because when the stock market crashes they don't want you looking at it they don't want you getting depressed and mad at them because they don't know what they're doing blind leading you as the blind person that is so true so you got to be careful that's very true I like that point because um I've heard people talk about passive income has been just set it and forget it and I'm learning uh no that doesn't happen there's something that you have to do in there to kind of like keep it on this the minds of everybody even though you may forget it. There's something you have to do. Do you hire teams to work with you on those? Yeah. So, here's what I do is uh so like with all my investments, there are usually some other real estate person operating the deal, right? So, for example, even even my most active I would say, right, is having rentals. But I buy what are called turnkey rentals from turnkey companies who help me find the property, finance the property, and then they also help me get the property, manage the property. So they're the ones taking care of it. They're the ones getting the renters in. I don't do any of that. I'm hands off. Now, right, if there's like a big repair that has to be done and they need to get permission, they might have to ask me. Now, now it's not passive any. Right. Now, if there's a renter or they got to evict somebody, they'll tell me about it, but they're doing all that hard work. Right. Right. Exactly. So, I am still hands off. Um, other ways I make money is like I lend money to real estate investors because a lot of real estate investors, especially lately, the last three years have been great because as interest rates climbed, now they're looking more for private money. And so, I can lend them money at 10, 12 or more percent a year, lend them the money, but then I could also be on the property. So, if they don't pay me, just like somebody who has a mortgage, right? If you don't pay your mortgage payment, the bank takes it from you, right? Same thing. I'm the bank now and if they don't pay me, I can take the property which usually has to have at least 30% equity in it, right? So even if they don't pay me, I know I can take that property back. I don't want it back. I don't have to go through that hassle, but I know I could turn around and sell it and probably make more than what they owe me. So those kind of things, right? Um oil and gas. I've got money in oil and gas. I've got money in raw land where um raw land in that partnership I actually have them buying and selling raw land and then they'll turn around and sell it to people at in five 10 15 year terms just like a mortgage, right? And so they'll sell it for triple the price of what we bought it for, you know? So it's kind of like a buy low, sell high, but then I get paid cash off of it, right? So I I put a half million into that partnership and I'm getting paid about 13,000 a month, you know? So there's there's things that you can do that again, you don't have to be actively doing. You can have have the real estate investors be the active ones, but you're the one financing it. And that's the important thing to remember. If you don't have any money, I will tell you this, it will never be passive. It will be using your time or energy to help create more money. And that's fine. That's what we all have to do in the beginning. But once you start to build up that cash, taking that money and then you can use that money to get to work harder for you so you don't have to work so hard for it anymore. Yeah. And that's the that's what you want. And you you don't you want the money to work for you. Correct. Yes. That's right. Say that. Okay. Right. You want somebody to work harder for you than you do, right? Yes. Absolutely. Absolutely. You've built your success by going against traditional financial advice. How do you deal with the push back from financial gurus who still swear by those things, those, you know, those games? Oh, I love it. It gives me it gives me podcast material, you know, for my own podcast. He gives me material for my long form, short form videos. It's great, right? Um because you got to have those Dave Ramseies of the world, right? I mean, bless his Tennessee heart, you know, he's out there helping a lot of people that are not able to make it paycheck to paycheck. He is really meant for the broke person, right? But the unfortunate thing is a lot of people that listen to him are usually the penny pinching savers already. They're already doing all the stuff he's been asking. They've done it forever and yet they're still broke. Now, they'll say, "Oh, I'm not as broke as those people are." But the truth is, if you ask them, "Can you quit your job right now and comfortably live for the rest of your life, never have to worry about making a dime?" And the answer inevitably is no, right? You know, if they're truly honest, right? I've seen a few people that try to probably get the way it's like, "Well, I can live on $2,000 a month and I can make my, you know, 500,000 last." Like, maybe, maybe not, you know, depending on what you're doing with that money. But, uh, but that's the thing. And so I love the push back because the truth is like I always like to tell them it's like well look at the evidence right Tony Robbins says success leaves clues. Well there should be plenty of clues that if this has been working that whole set and forget it spend nothing save everything save it forever in your crappy mutual funds and hopefully someday you'll have something. Shouldn't there be just millions upon millions of people saying I have retired free financially free? Yeah right you're just not getting that. I mean, no, the only people I've seen that sometimes will say, "Well, I saved and it worked for me." They either had a business that they sold for millions of dollars or they also bought real estate to enhance what they're already doing in the market. But people that have 100% only put money in the stock market, unless they are really penny pinching cheap sons of guns to make it very nice on the show, keep it PG for you. um you know to keep I mean they're less there's like they're penny pinching everything their whole life and then they penny pinch even their quoteunquote retirement. Yeah, they might make it. They might be okay. But remember my dad was that guy. He was saving everything he could. He was debtree. He was doing everything right. But now he's lived longer than he expected. Now he's into his his early 80s. He's thinking my goodness like now I've got nothing. I've had to spend it or I've had to spend it on home health care and things like that for, you know, nurses to basically and hospitals to keep me alive longer than I wanted to, you know, and those kind of things. Yeah. And that's and that's the problem, you know, and many people I just tell them like you can always live on ramen noodles if you want. You you'll die faster, you know, and uh you'll you'll be cheap, too. But again, I don't want that for people. I want them to have an option. I want them to have choice to say, you know what, I'm going to splurge and I'm going to go visit my grandbabies, you know, I'm going to go do, you know, live my life and do stuff. Maybe I don't have to wait till I'm 70 years old. Maybe I can do it when I'm 50 years old or 55. That's the kind of stuff that gets to be fun for me. Yes, that's great. What's the most shocking thing you've uncovered about people's hidden cash flow? And how many of us literally are leaving money on the table without even realizing it? Everything you've been taught by financial institutions that then train the financial advisors that work for them, right? They're little their little pawns in the game. You know, you'll realize your whole life you've been told to put your money in prison. You were told to lock your money away into the equity of your house, right? And then you can't get to it unless because when you need it the most, that's when banks don't want to give you money. And so your only option is to sell it. But what if you don't want to sell? What if you don't want to leave home? What if it's a bad market to sell in? Do you really want to do that? Right. Um or lock your money away in a 401k or an IRA if you work for a company with a 401k. You hear that all the time. I hear it all the time. Yes. Yeah. I mean that that kind of stuff is is just locking away in prison. Now is there a purpose for it? Sure. But the problem is that so many people never feel free along the way. Think about when you put your money. Everybody gets so hot and you know hot and bothered about getting that that company match, right? Which by the way does not give you 100% return. The reason I know that because if you put into a calculator and you put 100% a year compounded interest, you will become a multi-trillionaire saving very little. I can promise you no one has ever been in the news saying this person made trillions of dollars saving their 401k for the last 20 years. Never. The news and so yeah, you do make a little bit more money, but it's it's much smaller than most people think. And 401ks have a bad performance. they actually underperform the stock market significantly to where the match just makes up for the bad performance and the high fees, right? So really you'd be doing the same doing it on your own, but at least that money would be free, but they lock have you lock it away. And so when I get people that come to us and say, "I want to be free. I want that financial freedom." I was like, "Great. Where's your money?" Well, I have in my company's 401k. Okay, cool. Well, the only way you can get to it is by quitting or getting fired. I don't recommend either of those, you know, like you you don't have to just change a job and possibly have, you know, be unemployed or have a bad job. So, right, people realize that like they've locked this money up and they can't do anything with it. Versus that when they change jobs, well, now it's free game. We can do stuff like we can roll over a 401k and have you invest in real estate. Most people don't know that, but you can actually do things like that. You can invest it and lend money just like I said, right? You can do all kinds of things. Makes sense. Like with one of my clients where she lost her job. She got fired last year. So 2025 she's been unemployed. I was like, you know what? You're not you're barely 55. You can use this rule of 55 or you can actually get the money without the penalty, but you still have to pay taxes. But if this is going to be your lowest income year because you're not you don't have any working income coming in. This might be your year to get the money out of that 401k and get it in your hands and then you can create passive income to pay you right now instead of waiting until you're 60 years old, you know? So there's options, but most people don't realize that they're always taught to lock that money away and then they're stuck. And instead, if you can get that money out of prison, get it liquid, and then get it out to somewhere else, then you can actually create freedom right now versus waiting decades from now. I hear your your correlation now. It's make, you know, that's a really good correlation. You're not debtree because you lock your money away. That is so good. That is so good. Is that the same now? I know 401ks work differently, but you know, I've heard a lot of women that I work with um you know, coaching them and they they're so intent on this pension now. Can you talk about that? You know, pensions if you can get one and they're so rare because it's usually just with a few select government employees, you know, great. You know, pensions are great. Um and the nice thing is the company contributes to it anyways, right? So, it's not coming out of your pocket. But even if you have a pension, don't think that that's going to save you because we've seen over time companies have, you know, violated it or they've even just said, "Hey, we know we're going to say you're going to get this much. It's now only going to be this much instead." Right. Right. Social Security, right? Like people count on social security. Same thing. So pensions, I think pensions are great if you get one. Um, and that's awesome. But do something else with your money that you can control. That's out of your control. And if when you have no control, you can never have true freedom because you know that your freedom is always reliant upon somebody else. It's like it's like being a child again, right? It's like, you know, you never really know you're safe unless your parents keep you safe. Well, what if they don't, right? And that's the same thing with pensions, government, social security, and everything else. You've got to do something. They also keep you safe as well. Yeah. Right. Right. A lot of people are scared to break free from that grind. What's the biggest fear that holds them back from financial freedom? How do you help them shatter that illusion? I think the biggest fear is that there are a lot of charlatans out there trying to sell you on your dreams, right? I mean, I'm talking about, you know, real dreams and whatnot, but I'll tell you, and you know, people ask me like, "Who's your competitor in the space?" And we do like one-on-one coaching with people and help them create this kind of plan. There's not really anybody that does what we do very well, right? Um, but there's a lot of people that claim to do that kind of stuff or like they've got some, you know, some online program that you just have to watch a couple videos and you're gonna be financially free, right? And that's just not the case. Or a lot of times these people aren't free themselves, you know, and they're literally lying to you about what they've done, you know, and and that bothers me. That's that's the reason why I can't just retire off into the sunset, you know, you know, just just disappear is because I really feel responsibility that to not just fight against what financial advisors are doing, but fighting against what other people are doing that are trying to to really play on your fears and then never deliver and then you just lose money. Right? I've seen so many people lose money in different investments, including investments I talk about, but because they put it with either bad actors or bad operators, one of the two, they end up losing a lot of money. And then, of course, the normal everyday crowd is going to say, "See, I told you so. That's too risky. You shouldn't have done that." You know, you you try to break out of the mold, break out of the box, and look what happened. You got you got, you know, you put your hand outside the box, you got bit. So, just stay in the box with the rest of us. And that's not what like you should be able to break out of that box and say, you know what, this box, I know there's tens of millions of people just like myself that are doing it right now, living it. Again, we're not financial advisors getting paid to tell you that, right? So, that's the thing is that you have to make sure that you're listening to the right people if you're going to try to do something different. But I'll tell you, if you want the same results as every other American, and like I said, look for evidence. If you want the same results as everybody else, which are not pretty, keep doing what you're doing. keep doing what everybody's telling you to do. The reality is you've got to do something different. So, kind of like Jerry Seinfeld said in in a in an episode with George Castanza, if you guys ever seen that TV show and uh there's an episode called Opposite George, because George is a loser in every episode, but one, he decided to do the opposite in that one episode. He got a different sandwich and then he got the girl of his dreams. He got the job of his dreams of the New York Yankees and everything else, right? All because he decided to do the opposite of his normal behavior and it worked. And I just tell people do the same is like listen if millions and millions and millions of people have done the same thing it hasn't worked why do you expect it to work for you do something different do it different I'm in that place right now I'm telling you I am so in that place I I'm I I work with people that have you know experienced trauma generational or what have you with trauma right um I hear a lot about about their money situations because trauma does get into money and I want to hear your take on that on um how it affects people's finances and what steps would you take to kind of unlock that real wealth in them. Yeah, it's very important to understand how you were raised around money, especially if you're in a a marriage or some kind of relationship with a partner or something like that because you bring two different paths and other people's trauma and weird stuff with you, right? This is why people are like, "You got to pay off your mortgage." Why? because our grandparents during the Great Depression literally at that time it was legal for the the bank to say listen you haven't paid off your mortgage pay it off or we take it away from you right now and because banks were you know short of money but after the 19 but in the 1930s they created a law saying no as long as you're making on-time payments the mortgage company cannot take it back from you different rules different game yet we're still living by those same rules as way back when and that's the problem is that we're playing by old rules that don't apply anymore 401k. People are like, "Oh, I'm going to be in a cheaper tax bracket when I'm older." How do you know? The truth is with inflation, you're gonna have to spend more money. Even the tax brackets don't change. Guess what? You're going to be in a higher tax bracket. But they always tell you you're going to be a lower tax bracket, but that's just not the reality, right? So, things like that. Um, so if you have trauma, there's three money mindsets you should think about. Um, most people are either a spender or a saver. Both of these mindsets are in scarcity. Neither of them work. Neither of them serve you. A spender, we get the spender, right? It's easy come, easy go. You hyperfocus on the income you're making, but you ignore what you're spending because you just kind of the money comes in and it goes out and it's gone. The saver does the opposite. The saver hyperfocuses on all the expenses. If they pay a bill, they feel bad about having to pay a bill. I had a saver try to convince me they were a spender because they pay bills. I was like, if that's ever evidence that you're a saver, you know, if you're feeling guilty about being alive, paying a water bill, that's a problem, right? That's how you really good one. I like that. Yeah. Like, think about it. Like, he created all that trauma, you know? Um, I mean, that's that's ridiculous. I've known so many people that have have convinced other people that they were broke, absolutely flat broke, yet they had hundreds of thousands of dollars lying around, but they were just like, "No, I'm broke. I'm broke." See, neither of those work. Neither of them work. A saver can never spend money, you know, can never save enough. They can never pay off their debt fast enough. They're always feeling bad. Spenders, they always spend the money, but they never have freedom. They always have to keep hustling. You need to be learn to be a steward, a wise steward of your money, which is the best of the spender and the saver in one person. Because spenders are willing to use money. They just use it unwisely. Savers want to be wise with their money, but they just hoard it. They cash it away and it does nothing. They let other people make money off of them instead of them make money. stewards say how what's the highest and best use of this money that can actually generate more freedom that can create you know not just improve my life but improve improve the lives of those around me right that's why we call the company money ripples right what's the ripple effect you can create when you financially prosper you know and that's the same thing here is like you know you got to be a wise steward of your resources how do you grow it and multiply it just like the parable of the talents in the Bible right like how do you actually grow and multiply it not hort it away like that third servant in the Bible who then got cast out Right? That's a saver. Savers get cast out. You don't want to be that. You want to be the steward that's willing to take money and use it in ways that not just enhances your life and creates passive income, but blesses the lives of people around you. Yeah. I like that. Oh, I love that. I just love it. Oh, this is so good. This is so good. Audience, I tell you, I love talking about money because of course I'm from trauma, so I'm always healing and going in those dark corners kind of finding things. Hey, got to heal myself on those things. This is really good information. You know, I always say every time I have a a a new guest, I say it's for me first and my audience second. Right. Audience. So, where and what are you doing now, Chris, that you can share with the audience what you're doing, where you're going, where we can find you. Let us all know about the goings on. Yeah. Well, I've mentioned a few times Moneyripples, right? anything money ripples, moneyripples.com, moneyripples podcast on all platforms. Uh we also have uh like you know even atmoney ripples with social media. Um but the main thing we're doing is really just educating people to break free as as we've been talking about here, right? Um even that abundance mentality that goes along with trauma too. Like many people have just trained in scarcity like I was, you know, I lived in a trailer park for 5 years, you know, like money was never an abundant thing until later when I became an adult, you know, when I changed my mentality around that. So, we talked a lot about that and strategies and whatnot. Um, and actually I'm even writing a book called Work Optional Blueprint talking about that story and how I was able to, you know, eventually, you know, like I said, become financially free twice. And, uh, so that book's going to be released here this fall. So, be looking for that, too. Awesome. That's terrific. Well, if you're feeling inspired by Chris's message, make sure you check him out. Money Ripples, okay? And start creating your own path to financial freedom today. You know, you can do this. He's saying you can do it. I believe you can do it. We both believe that you can do it. So, make sure you look for him because I am definitely going to look him up even more now and pay attention to what he's saying. This is Edna White, your host of Keeping It Real, and my guest, none other than the money man himself. And we want to thank you for being here. And remember, keep it real. Bye for now.