From Broke to Financially Free: How to Escape the Traditional Money Trap

My dad was the penny pitching saver. Yeah. I mean, he paid off his house in 18 years, he was 100% debt free. He had stuffed money as 401k. And then I said, dad, here's the deal. I'm looking at your finances right now. If you want to retire today at 61 years old, despite all your best efforts, you better hope you die in five or six years because that's when you'll run out of money.

Hello, everybody. Let's talk to Chris Miles. Hello, Chris.

Hey, Larry. It's good to see you, man.

And you know, I'm excited about what you're doing, about the people you're impacting and, you know, the message you've got out there, which is of overcoming financial situations and, you know, putting yourself in a position to win financially and in life. And how did you wind up, how did you move towards that kind of role in life? You know what, you know, as you came up, what were you interested in? What motivated you? What, what grabbed your curiosity?

I mean, I was raised by two very different parents. I had one parent, he was like, you work the corporate job, you get that good education, you work hard and then finally you'll make, you'll be successful. Then had another parent that she was an artist, believe she was a starving artist. She was actually trained by the same master painter that trained Bob Ross, you know, the guy that paints the happy little trees and stuff, Right? So she was trained by the same guy as him. So she was like, follow your dreams. And he's like, no, follow the money. And so of course I did neither. You know, I kind of did a little of both or neither, depending how you look at it. I, in college, I actually decided to go into sociology. Didn't even know what it was. I just felt I should probably major in sociology because it seems like psychology, but different. So I did, I went to sociology in college. But then as I was getting in college, I realized that the most successful professors I saw were not the lifetime professors. They're the ones that were out in the real world and then came back to teach. And so I decided I want to become a business consultant. And so my whole goal was I'm going to go out, get my mba, be a business consultant. But then I, then the words of my dad also came back to me saying, you know what? You need real life business experience. You can't just take, you know, get the book smarts. You need the real life smarts too. So I actually dropped out of college. I had one course to take Before I got my degree, I said, I'm going to take a year off, start some business to get some real resume experience, and then go back and get my mba. And so I did. And the first thing I actually found was a few months later that intrigued me was actually becoming a financial advisor. Because I figured, worst case, not only do I learn about business, I learned about investing, too. And so that was the path I took. And I love being an entrepreneur so much, I actually said, you know what? Screw my degree. I'm just going to take this route. I'm going to become an entrepreneur. I'm going to do that instead. And so I was, I was mo. I was. I was working full time on a corporate job and then also doing a side gig as a financial advisor for a few years. Did that actually eventually became full time into financial advising. Four years in, and, and after four years, and I was, I was. I drank the Kool Aid, you know, you know, because I know you and I kind of share a common history that way. We drank the company's Kool Aid, we took their training, we. We figured whatever they taught us was true. And so I did that. And I. I figure if I just, you know, save everything, spend nothing, save it forever, and hopefully someday I'll have something right. And it was actually that moment. It was. It's actually back in Thanksgiving, 2005, my dad said, well, Chris, when are you going to advise me now? My dad was the penny pitching saver, just like I was becoming, right? He was the guy that died Dave Ramsey would have looked up to, you know, like he, you know, I mean, he paid off his house in 18 years. He was 100 debt free. He had stuffed money in his 401k, got the match like every good boy should. And then I said, dad, here's the deal. I'm looking at your finances right now. If you want to retire today at 61 years old, despite all your best efforts, you better hope you die in five or six years, because that's when you'll run out of money. Said, all right, well, what do I do? I don't know. You did everything right. You did it by the book. For what I teach as a financial advisor, I don't know, work longer, save more. That's it. And, and that bothered me. And it was finally like, it was just a month later. I'm talking with a friend of mine who I trained to be a financial advisor on my team. He left to go do real estate investing, and he starts telling me how real estate's Best investing is way better than stocks, which pissed me off. And so I, we started getting into a little argument and he finally stops and he's like, chris, let me ask you this. How many of your clients are truly financially free where they don't worry about money? Said, well, they all worry about money. You know, even the retired ones still worry about outliving their money. Great. Good job, Chris. Way to go. Um, by the way, that's not all my people. That's from decades of advice before me too. Um, and then he says, well, Chris, how about this? How many of you guys as financial advisors are financially free, not enough the commissions you're earning, but actually doing these same investments. And I remember thinking back, I'm like, there's guy's been working in my, in my company for the last, really since the 1970s, you know, working for the same company that you and I work for, right? And I'm like, maybe none of them. And he's like, well, there's your problem. And, and finally I decided to like, take the Matrix red pill, right? I said, all right, I'll, I'll bite. You know, let's see. And I read books like who Took My Money? By Robert Kiyosaki, a lesser known rich dad book. And I this AM talk radio show with these two real estate investors talking back and forth about stuff. And, and pretty soon it was just months later I realized either I keep going down the path I was going on because I was at the height of my practice at that point, or I quit and keep my integrity intact. And so I chose a ladder. I decided, I'm going to quit. I'll never teach about money again. I'll just be a mortgage broker and teach some stock trading on the side. And I'll teach ballroom dancing, you know, because I used to be one of the nation's top amateur ballroom dancers. Thanks. So, yeah, it was another fun thing from college. I could have triple minored in, in ballroom dancing, Japanese and psychology. That was my, that was my triple minor there. So, so anyways, I, I, I started learning the things that they did in real estate, you know, instead. Cause I wanted to know what these guys knew. These guys were like multimillionaires in their 20s and 30s. So I started to do it myself. And later that year in 2006, I was, you know, 28, almost 29 years old. I was actually had enough passive income to stop working. I could have just retired. Where I call it work optional, where you work because you want to, not because you have to. And that blew my mind. I didn't even think that was possible because remember, I was the accumulation mentality of just set and forget it. And if I just accumulate enough money, I can live on less than the interest. Right. And, and that was completely different mindset of going for passive income and cash flow. Like Kiyosaki teaches in rich dad, poor dad versus the traditional way. And that's where I kind of eventually, you know, everyone wanted to know how this 28 year old nothing kid, you know, did what he did. And so that's why in 2007 I came out of retirement to teach people how to. I did what I did. That new business was at the perfect time because the recession hit. I went from millionaire to upside down millionaire. In 2008, Nine was able to dig back out. And finally at the end of 2016, partly real estate also tied up in the business. The new business we started and the business was focused towards real estate investors. So the business was suffering. Leaking cash. I personally was starting to leak cash not just from the real estate, but I'd actually try to pay off my house. You know, I try to pay down my mortgage. And then by the time I said, oh, maybe I should do a cash out refinance, the bank said, no, you can't do that anymore. You know, because I thought, I thought that was a safe place to put your money. You know, that's what Dave Ramsey taught me. And that didn't work either. So, so I eventually, you know, that's part of the reason I had all my money tied up and the real estate market dropped, so I couldn't even get to the equity that was in there. And it was, it got me close to bankruptcy. I didn't file for bankruptcy, but man, I mean it put me in a really tough spot.

Yeah, you can't, you can't really go through an entrepreneurial lifestyle without either going under financially once, once or twice or skating on the edge. You know, the trouble is we're out there skating on and you know, the deal is you're, you're out there and you got to work in the economy and the economy is something we don't control. And it's like you're out there skating on this ice lake, but you don't know how thick the ice is. And ordinarily it's thick enough to support you, but it's easy to. All of a sudden now there's been a warm spell over here, you fall through and again you were doing everything right, but now you're underwater.

That's that's the thing is, like, I mean, like you said, there's always different levels. Because I remember the very, you know, first time starting as entrepreneur, as a financial advisor, I was freaking out because I had a $5,000 credit card balance. I was like, oh, my goodness, are they gonna throw me in prison for having a $5,000 balance? Yeah. What do I do? I'm in debt. I would freak out. Cause I was always a cash only kind of guy, right? And then, of course, when the next recession hit, I'm thinking, man, 5,000 would be amazing versus a million dollars of debt to have to pay off. And, you know, again, I did it, but it was much harder the next time around. I mean, it's all numbers anyways. It's all mindset. But no, it's. It's. I mean, every challenge is different, the lesson there.

So people pick up the lesson as we go along. You got to make sure you got liquidity, you know? You know, in fact, they say that about. I don't know if it's true or not, but they say Elon Musk, you know, he has all the homes he owns. You know, he. He doesn't own any of them. You know, he's got, like, a dollar equity in every home. You know, because if. If there's a problem, that's the bank's problem, not his, you know, and so that, you know, you have your hands on your money, but you don't know that. If you came, you come up and you take conventional wisdom and you learn. So what we're hearing this, you were forced to learn to think for yourself, and it paid off. But then, you know, it kind of bought you. But all along, you know, all along the way, you're. You're learning lessons, you know, you. You did some things right. I don't know if you. You, yeah. Are aware of it. You did things like. Even when you were in college, you said, I don't know how many of us in college thought to say the most successful professors are the ones that are out working and they come in. I guess in my world, at Georgia Tech, there. There weren't any. Any great professors. They were all boring as hell. But, you know, had there. Had there been one with any kind of spark, it would have been obvious. I guess maybe they stand out because they're. They come in with a little fresh energy. But, you know, you did notice that early on, and you took a lesson from it. You know, you seem to be able to read the tea leaves pretty well in life.

Yeah, I Mean, despite the mistakes. Absolutely. Like there's a lot of times that you know, I'm a visionary, right. Like I do see things before they happen. Which is great when you're in business because you can kind of predict to say here's where the market's going. Or you could predict to say, you know what if I keep doing this, it's going to lead to destruction. Right. And, and I'll tell you, I actually felt it even in 2006 and 7. I'd felt that something was, was off. But I, I really, my pride and my ego got in the way where I was like, you know what? Doesn't matter. I've got the Golden Midas touch, right. Like I, whatever I touch terms of gold, it, I'll figure it out. Even if there's some challenge that comes up, I, I got my brain, I can do this. And that's what happened in 2007 is like 2007, like we're launching this new business. And I did, oh, that's the other mistake I did make. I did cut off my passive income streams to go all in with that business, right? So the very thing that got me to be free, ironically, we were teaching people how to create passive income streams. And what do I do? The opposite. Because why the partner says, hey, we need you to be all in. So stop this other, you know, know, passive income streams and just go all in this way. Stupidest thing ever. Like, I don't know why I didn't listen to my intuition then my gut, but I knew that something was off. But I was like, well, I'm a team player. I don't like when people say that I'm not a good team player, so I'm going to do what they ask. I would have been way better off doing what you said, being liquid with cash. I was liquid. I had my six month savings like they always recommend. That wasn't enough, you know, especially when you have all the other business and things coming in. And of course, you know, I, I cut off those passive income streams that could have helped me weather that storm better. And, and it is what it is. Like I learn now, right? But, but I did feel something was off then when he asked me that. And I felt something was off when I even bought that house in 2006. I bought a house, it was a nice show home. It was beautiful. I was buying it because I lacked my own self worth, right. I, I, I didn't believe I was worth much of anything, you know, so what do I do? I buy things that are worth a lot, that put it in front of me and say, look at how awesome I am, how valuable I am. Here's this beautiful house that you walk in, you go, oh right. And I went and bought the Mercedes and like, ooh, you know, like this is a successful guy. I'll tell you. My financial freedom really began to start not when I escaped the rat race in 2006. My financial freedom started about 2008, 2009, when I became detached, I turned in that Mercedes, said here, take it back, you're going to take it from me anyways. Eventually if I don't make payments. I eventually foreclosed on that. That nice 3/4 million dollar house which is back then was worth quite a bit now. 3/4 million is like an average home, just about. But I mean I, I, I, I got rid of all that stuff and when I stripped it all away, I was left with a choice. Am I valuable or not? Am I still the same person or not? And once I lost all that stuff, ironically by 2009, when I lost my house, it was just once I got to the point I was detached from all the things and I didn't care about impressing people anymore. Just four months later, things started to turn around. Right after I finally lost the last thing that I was holding onto, which was the house. Once I released that I was going back to renting a house again for a quarter of the payment and I was just going back to now nothing. That's when everything started to shift and turn around.

There's the problem with experts and you should really watch your instincts. You know, the thing is an expert can get you to turn off your instincts a lot of times. But there's, there's a reason you have a gut that's right, you know, and in any situation you show up, you show up with your brain, with your experiences, with your, you know, backlog of things you've been through and things, you know, whether you know them or not. And that, you know, that subconscious thing can be very, very helpful if you pay attention. When did you, how do you think things turned around? You know, one reason I would, one thing would be a clue is you had less distraction. You know, the thing about a house is it takes up a lot of your time. It's really funny. People get the birth, they get the big house. And you know, in our business we've had a lot of people come from nothing and go out there and have incredible success and they all want the big house or at least the spouse does. And they only seem to really enjoy it unless you have a big family, a lot of kids and a lot of family coming in and out to enjoy it properly. The only time they really enjoy the house is when someone new comes over and they get to show it off. Because that's when you could show off, look at my house. And then after a while you'll go around and they'll say, you get to the end of it and you'll say, man, this is fantastic. It's really impressive. And then they'll say, well, do you want to buy it?

Yep.

Because they're tired of it. You know, it's true. They want to move on like you did. And so when you get rid of these things, you, you f you, you still got your time. You got to focus on something. And so what do you think happened in those four months? What were you doing in those four months after you kind of got rid of the, basically got rid of the expensive clutter out of your life and started thinking seriously about moving forward?

You know, it, I mean, 2007, I realized there was an issue. I mean, it was, it was becoming pretty obvious. And that was, in fact, it was the first time I started tracking my money. That's when I found I was in the hole 15,000, 16,000amonth between my business and my personal. What was going on because I just wasn't bringing in enough. Plus the business structure, the way I got paid was horrible because we're reinvesting so much money back in the business. So that was one big issue for sure. But I'll tell you, like it was after I realized that I could no longer teach getting people out of the rat race. When I was back in the rat race, which was probably about, probably end of 2007, going into 2008, I started really questioning what I teach because again, I can't teach something I don't believe in as evidence. Like when I left financial advising, right? And, and so I'm like, well, I can't teach something. I'm a horrible poker player. People can tell when I'm lying and bluffing. Well, what do I, what can I do? And what I realized is that I was getting very creative, trying to figure out how to stretch my dollars, how to like find cash that I didn't know I had or, or maybe is. Was buried or something like that. And, and just getting very resourceful and very often I have people and we, we had a high ticket coaching program. I mean, now it's not, it's not very high ticket in Today's days, It was like 7, 500 bucks. Now, you know, but back then it was 7500 was high ticket. And people would say, boy, I would love to know what you know. I would love to learn from you. I just don't have the money to pay you. And I would tell them, I was like, now in the back of my mind, I would say to myself, there's financial situation is way better than mine is right now. I wish I was in their situation, but what I. But that's business suicide. Say it out loud. So what I said instead was, well, what if I could help you find the money? Would you then pay me? I said, yeah, of course. My greatest rate. And so I just show them creative strategies, like, here. Here's a way to free up on taxes. Here's like, if you start looking at your money and where you're spending it, if we do this, this, and this, we'll free up like $400 a month or whatever. And like, hey, if we do this, it can, you know, consolidate debt or do this and this with your debt. We can free up money here. And the next thing I know, people are like, wow, that's incredible. I just fr. Freed up 2000 bucks a month or whatever. Right? And not. Not because they were necessarily overspending. A lot of them were good savers, but it was just money. They didn't realize they were leaking and they. The first place. And so I started to focus on that.

Yeah. And yep, there's so many stories, and we know so many people that are constantly talking about how broke they are, yet they never stop buying. You know, I got this, you know, this got this, and they got that, and they got the, you know, the expensive lunch and the, you know, it's always something new, but they're broke, and so they. They can't connect that dot. But you don't want to be your. The lesson there is you don't want to be your own worst enemy. And so you. That led you. How quick did that lead you to writing the book Money Ripples?

But then, you know, after a few years with those partners, I realized, like, there was a diversion. Certain hap happened, you know, like difference of cultures and beliefs and value Systems. And so 2012, I launched out and created Money Ripples. I wasn't planning on it, funny enough. I was only trying to create another business to be another marketing arm for the business I was in, because I was planning to take over the business. Have you ever heard of a guy named Garrett Gunderson? He Wrote the book called Killing Sacred Cows, which is a financial book talking about the common sacred cows or myths that people buy into with money. You know, I was working with him. My plan was to take over his business, you know, because eventually, like my, the things I was teaching became our coaching program, right? Because it was the thing that kind of revolutionized everything he did. Still to this day, the now company called Wealth Factory still teaches my stuff, stuff from 2012 when I left. They're still teaching the same thing, my same horrible diagrams they're still using to this day, you know, but I, I knew that, you know, I wanted to try to do something more. And eventually we got to a point where he just said, I don't know how this is going to work, you know, so even though I was trying to align with them, he just said, no. I feel like there's too much conflict here that it doesn't seem like it's working. Here's your termination letter. And so I was fired right off the get go. A company that helped build from the get go, from the start, helped even rev, keep, keep, save the company, essentially, right? And they're like, you're, you're fired. I almost felt like Steve Jobs a little bit, right? It's like, wait a minute, like, you can't fire me, you know, Like, I, this is my baby. But they did. And, and the crazy thing is they say, hey, here's a little severance check for you for as a thank you for the millions you've helped us make. I remember I, I pulled over into a parking lot of a church. I started praying and, and I remember just getting the feeling like, you know what? This is going to be part of your story. In fact, this will inspire a lot of people to not give up. And so I, I, I got done with that prayer. I decided to open up that severance check. It was a whopping thousand bucks. Needless to say, I gave him the proverbial finger for that one. I was like, I'm, I actually left there, I left on good terms. I'm like, listen, I'll help you build out anything, anything you need to replace me, I'll do it. I'll help you out. Thank you so much for giving me a check. I saw a check. I'm like, you guys are on your own. Like, I need to use this money to start up my company. And fortunately, Jeff, I'm going to crush you.

Yeah.

Oh, yeah, Yeah. I mean, now, again, you mentioned, like, going with that intuition, right? Just weeks prior, I was feeling like I Needed to create something. And I was trying to come up with a clever name for this company I was creating. And, and I remember I was on a run because it's usually when my best ideas happen, I'm on a run. I started thinking about the vision. I was like, and I was thinking about the hundreds of people we'd already served. Like we freed up millions of dollars for people, on average 2,800amonth. And there's one particular client I thought of that is out of South Dakota. We freed up $6,000 a month for them by restructuring some, some of their loans and stuff. Again, good savers. But, but you know, with business and everything else and the recession, like they built up some, some debt and so I helped them restructure it and free up like 6,000amonth. What did they do? The first thing they did, they bought a $6,000 four wheeler. Now a Dave Ramsey would have judged him for it, say, oh, you horrible, you know, sack of crap. You know, like, how dare you do that? But I remember the wife even said, she's like, I know people might judge me for this, but here's the thing. That $6,000 four wheeler represent more than the four wheeler. Because what it did, he was working five or six days a week in his, in his business, but now he felt like he didn't have to work so much. He felt like he could come home with us on the weekends. So what did we do? We bought that four wheeler and now he's riding that four wheeler with his sons every single day. My kids got their father back and I got my husband back. And I realized at that moment I'm like, you know, when I'm on this run rethinking about that, it's like, what does that really do? What's my vision? I was like, well, that creates a ripple effect because it not just blesses the family, it creates a new legacy for the children to follow of new prosperity and abundance with money. And that ultimately gets them away from worrying about their own needs and starts looking outside themselves that could bless the community and ultimately that ripples across the world. And that's when the name money ripples came to mind. And I've got this 150 page book now called Work Optional Blueprint that's coming out, actually launching in September, late September of 2025. And so super excited for that book because it's, it really is a labor of love. And I hate to say that some team members probably worked on it more hours than I did. I just had to talk a lot and then, you know, do some fine editing on some of the details. But I mean, they, I could not have done without my team. And so it's, it's something I'm really excited because it really teaches people how to do what I did, which is become work optional twice. And we've had now, since then I've, I've stopped focusing just, just on freeing up cash flow. Now it's focused on how do you create passive income enough that you can work because you want to, not because you have to. You, you really have enough money working harder for you, so you have to work so hard for that money. And so it's really that how to, of how do you make it actually make that happen in your life?

Well, I'd like to wrap this up by giving you a chance to kind of encapsule what you would say to people the old way, the new way, the smarter way to think about their money. And maybe they'll come over and, you know, I want to get into the podcast and the things, you know, the specifics of how you're building your, your outreach now and making that impact. But we'll do that. We'll, we'll do that on the behind closed door session that we take for the, the community. But what I wanted to do now is could you put into words, you know, you came up what, what you learned from your f. Your father and traditional and versus now what you. The how can you put into a nutshell the change that people need to go through so that they can get on track to be financially independent and not be in a doomsday scenario financially for sure?

Well, definitely, I would say question everything you said. I mean, you really talked really well about critical thinking, right? Like turning your brain on when you do these things. Question what's being taught to you. What I've learned is that money, the success with money is not about being a good saver. Savers still lose. It's about being a wise steward of your money. Stewards, they're willing to be like savers and be wise with their money. But like spenders. See, spenders are easy come, easy go, and they always get the bad rap. But the truth is spenders are at least willing to use money. What if you can use money in a way that comes back to you, how can you get your money to actually expand and multiply like a steward would do? Right? Stewards want to multiply their money. They want to amplify, they want to make it better, and they do it with a three step process is first you get lean. Right? We've talked about that. Like, how do you be a wise steward? Doesn't mean you cut out that latte, doesn't mean you live on rice and beans like some people teach out there. But it does mean how do I make sure that if I'm paying for things that I'm paying for the right things in my life that bring value to me versus the things that don't? Then you get liquid. You mentioned this too, right? So important to get liquid. So you need to have cash available. Unfortunately, almost everybody in financial advising teaches you to put it in prison. Lock in your four 1Ks and IRAs forever, don't touch it. Right. Set and forget it. As I always say, lock your money in equity in your house, which I learned was not good. Right? If you keep putting in equity, then how do you get it back out? You have to ask for permission to get back out. Or sell your house, which you may not want to do, is have that money liquid, get out of prison, and then you can get it out into things that do produce tangible, predictable, passive income right now. And that's the thing that you just won't really hear in the financial world today, and that's if you walk away with nothing, is remember to get lean, get liquid, and then get it out.

And we'll refer them for follow up in more detail on that to your podcast, which is Money Ripples, right?

Yep, that's right.

And I'm sure you can find it anywhere. Thanks so much, Chris. It's really been fun talking with you and I'm looking forward to seeing the feedback I get from people who hear this and start thinking about changing how they're going about their own personal finance, you know, and so congratulations and thanks for being with us.

Thank you so much.