Making six or seven figures but still feeling broke? You’re not alone. In this episode of Executive Connect, host Melissa Aarskaug sits down with Chris Miles, the “Cash Flow Expert” and founder of Money Ripples, to expose why traditional wealth strategies keep even the smartest professionals trapped in financial stress.
Chris explains how he went from over a million dollars in debt to retiring (twice) before the age of 40, without gambling on crypto or chasing risky investments. He shares how to create real financial freedom by rejecting conventional advice, unlocking cash flow, and investing for income instead of illusion.
If you’re a high achiever tired of living paycheck to paycheck despite a strong income, this episode is your roadmap to reclaiming control of your money and your time.
Chapters
00:00 The Wake-Up Call: When the Math Doesn’t Work
03:00 Breaking Free from Wall Street Thinking
07:45 The High-Income Hamster Wheel
09:00 Why 401(k)s and IRAs Keep You Stuck
14:00 The Real Path to Passive Income
19:00 What Financial Advisors Get Wrong
27:00 Wealth-Killing Habits You Don’t Notice
33:00 How to Rewire Your Money Mindset
48:00 When to Sell, When to Stay
50:00 Final Thoughts and Practical Advice
[Chris]
And it was just a month later, I’m talking with a friend of mine who I trained to be a financial advisor, but he quit, and he went to do this thing called real estate investing. And we get this argument about what’s better, stocks or real estate, and finally he just stops and he’s like, Chris, how many of your clients are actually financially free where they don’t worry about money? None.
Good job, Chris. How many of you guys as financial advisors are financially free? Not off the commission’s earnings, but actually doing these mutual fund investments.
I have to say none. There’s your problem. And so he got me to start really taking the matrix red pill, you know, he’s like, here you go.
Good luck. Go get this book by Robert Kiyosaki culture.
[Melissa]
Making six figures, but still feeling broke. Welcome to the high income hamster wheel. Today on the executive connect podcast, we’re joined by Chris Miles, aka the cashflow expert and anti financial advisor who didn’t just retire once, but twice before 40.
No crypto, no gambling, no Silicon Valley exit. He just paid off over a million dollars in debt and built real wealth by doing the exact opposite of what most advisors preach. If you’re ready to stop trading time for money and learn how wealthy really builds freedom.
Tune in today’s episode. It’s full of knowledge and your wake up call to financial wealth. Welcome, Chris.
[Chris]
It’s such a pleasure to be here, Melissa.
[Melissa]
Your story is wild. You went from massive debt to financial independence, not once, but twice. You did it without stocks and crazy risk.
My brain is thinking overachiever, but let’s walk us through this journey. What was the turning point? And what did you stop doing that?
Most people still think is smart.
[Chris]
Yeah, you know, so give you my back. So I actually started out as a financial advisor over 20 years ago. And I was I was the guy that was drinking the Kool-Aid, right?
I was the one telling everybody scream off the rooftops. You just got to set and forget it. Spend nothing.
Save everything. Save it forever. And hopefully someday you’ll have something, you know, and and so I was preaching that like crazy.
Like you just put it in my mutual funds. You’re going to be fine. Like you’ll make millions in here because I, I believed it too, right?
I believe that you’d be going to make 12% in the stock market. You know, it’s never done that long term. You know, I believe that, you know, you just keep putting away, you know, dollar cost average, all that kind of stuff you hear about.
That’s the answer. Well, four years in, my dad reaches out and he says, well, Chris, when are you going to advise me? Now, my dad, he had understand like he was like that penny pinching super saver, right?
He was like, he was like the guy that Dave Ramsey looked up to. It’s like, oh, I want to be like him when I grew up is what Dave Ramsey would say to my, you know, about my dad. And so my dad was like super cheap.
You know, he said, Frugal, we are like, no, you’re cheap. And he like, and he like, it was just always putting money away. That’s all he taught me.
So I, of course, was teaching the same thing as a financial advisor. When I sat down with him, you know, I grew up in Oregon, so I go back to Oregon. I sit down in his kitchen table, same one where he told me just to save everything.
And as I’m sitting down there, I’m looking at his money. I was like, dad, here’s the deal. Like, okay, you’re debt free, including your house.
Way to go. You know, he was really proud. He paid off his house in 18 years.
He’d been stuffing money as 401k, getting the company match like every good boy should. I said, but despite all this, dad, if you try to retire today at 61 years old, you’re going to have to die in five or six years because you’ll run out of money at that point. It’s like, okay, that’s not what I wanted to hear from you.
Like, what do I do? Like, how do I retire? This job is killing me, literally.
He’s like, I’ve already had heart attacks and strokes. I need out. I don’t know, dad.
You’ve done everything right from what I teach as a financial advisor. You just kind of keep saving or end work longer. And that’s obviously not what he wanted to hear.
And it wasn’t what I wanted to give him as advice either. And that really bothered me because I thought, wait a minute. I’ve been telling everybody to do just what he did.
And yet, even though he did it all right, it wasn’t enough. And it was just a month later. I’m talking with a friend of mine who I trained to be a financial advisor, but then he quit and he went to do this thing called real estate investing.
You kind of talk about it on the show a little bit, right? And so he’s doing real estate investing. And we get this argument about what’s better, stocks or real estate.
And finally, he just stops and he’s like, Chris, how many of your clients are actually financially free where they don’t worry about money? Well, they all worry about money. Even if they’re retired, they still worry about running out of money too soon.
Okay, great. So none. Good job, Chris.
How about this? How many of you guys as financial advisors are financially free, not off the commission’s earning, but actually doing these mutual fund investments? And at the time I started thinking about, I was like, well, there’s guys been working here since the 1970s.
They don’t seem like they’re slowing down anytime soon. So I have to say none. There’s your problem.
And so he got me to start, you know, really taking the matrix red pill. You know, he’s like, here you go. Good luck.
Go get this book by Robert Kiyosaki called who took my money. It’s a lesser known rich dad book that says mutual funds suck. Right.
And then, and then he’s like, and the list of this am talk radio show with these two real estate investors. And so I did. And after a few months, I got to this point.
I said, either I keep teaching what I know to be false now, or I quit and keep my integrity intact. And so I chose a ladder. I said, I’ll never teach about money again.
I’ll be a mortgage broker. Cause in 2006, everybody could be a mortgage broker. I’ll be a mortgage broker and I’ll teach ballroom dancing on the side.
And that’s what I did. But of course I want to know what these guys knew, like all these real estate investors that were like in their twenties and thirties, they were like millionaires. I’m like, I want to know how to do this.
And so eventually I learned what they did. You know, and I, and I actually learned that I could even invest with them rather than me trying to learn to do what they did. I could just put my money with them.
They paid me interest and I can create passive income that way. So I could be hands off. And so later that next year, I actually became financially free the first time, right?
Where I had enough passive income coming in. I didn’t have to keep working anymore. And of course when that happens, then everybody wants to know how you did it.
Right. Cause they’re like, okay, you’re 28 years old. You’re not supposed to be retired yet.
And I was like, I didn’t expect it either. It just happened. You know?
And so finally 2007, I came out of retirement to teach people how to do what I did. It came out with a few partners and we started teaching that stuff. But then the course, as you know, the recession hit and it hit hard.
Our whole business was catering to a lot of real estate flippers who are now going broke in 2007. On top of that, I had to got my money trapped in my house. Like, cause I had paid extra money towards equity.
Cause Dave Ramsey taught me to do that. And then of course, when I went to go get it out, the bank said, sorry, you’re a business owner. We don’t like you anymore.
So no, no cash out refinance for you. And then as a result, the values of my real estate started dropping. I lost all my equity.
Eventually 2009, I had a foreclose of my house like two weeks, actually 92 weeks. It was a week after my fourth child was born. And we’re literally moving out of the house while my wife’s going through postpartum and everything and stuff.
And it was just, it was just a hard, hard time. Went like, I went from like millionaire to upside down. Millionaires, like over a million dollars in debt had to dig out of that debt hole.
Finally, by the end of 2016, I was able to rebuild. I even launched money ripples in 2012 with a new business and was able to dig out of that hole and finally did it the second time. And at the end of 2016, this time much wiser than I was in my twenties.
I was definitely much more secure in how I was going to do it this time around. So that’s kind of what I’ve been teaching people to do ever since, is how do you become work optional where you have enough passive income to work because you want to, not because you have to.
[Melissa]
Ready to lead smarter and invest wiser. On the executive connect podcast, we unpack executive strategies for wealth and influence. Hit the subscribe button now.
Don’t just watch act. I love it. This is so timely.
I think so much of my scroll lately, I’ve seen people match as funny enough today, a friend of mine who’s actually been on this podcast posted something about how high income is a trap these days. And so I want to talk to you. I know one of your boldest claims is that exactly that, that high income can actually be a trap.
So that definitely hits home hard for me for a lot of my executive friends, entrepreneurs, founders, and Austin that are earning high income, either salaries or, you know, in their businesses. Can you break that down specifically for the W two employees on how chasing income alone can keep you broke versus the lab that you were talking about. And then maybe like the second part of that, what should they be focusing on instead if it’s not the high income job?
[Chris]
Yeah, I think they kind of already know is in the back of your mind, you always have that little fear that what if I don’t have this job? Like what if I mean, 2020 was such a nice little, you know, shot across our bow. It was like a nice warning shot for wasn’t it?
Because I mean, we saw, we saw the world shut down for weeks or months on end. And a lot of people got furloughed, right? I mean, people that had great paying jobs all sudden didn’t have an income anymore.
And it makes you ask yourself if I didn’t have that income coming in, what would my life look like? If also my income stopped today, all of it, what would I do? And especially if you’re a high, you know, like a lot of my clients are the same way, right?
A lot of them are high level executives or they’re, you know, business owners and people like that where they know, they know that if that income isn’t coming in, even though it’s a great income, they have a great lifestyle, social media makes it look great. You know, like, like everything looks good because their wife posts everything that, and from the outside of their life, it looks wonderful because they can afford a nice lifestyle. But if that money were to dry up, they’d be just as broke as everybody else.
And yeah, sure. They may have some retirement plans. Maybe they’ve got some savings.
But the truth is I’ve had so many people come to me that are like the Dave Ramsey poster children that have no debt, a couple million or more sitting in retirement plans and saying, I can’t even retire. Even though I’m debt free and I’ve got money here because I was just told by my financial advisor, I can only pull off 3% a year. Well, that’s not an income.
I’ve got 3 million sitting here and that’s $90,000 a year. That’s not what I want to live on. That’s horrible.
Right. And I’m getting that all the time. And that’s the trap.
That’s the big trap. Plus everything you’ve been taught from financial advisors is always about putting your money in prison. Lock your money up by paying off all your debt, paying off your house.
That was the one mistakes I made the last recession. If I would not try to hurry up, paying off my house, trapping that equity in there, I would have had that cash on hand. I could have weathered the storm of the recession much better, but because I sunk all this money in thinking I could just pull it back out.
Because in 2006, 2007, especially as a mortgage broker, I thought, huh, I’m a mortgage broker. I can get that money whenever I need to, because they give out mortgages to anybody with a heartbeat. As long as you have a decent credit score.
And then of course, even despite great credit score, they say, no, you can’t have that money. And the banks can change that mind at any time. So I saw that firsthand how that was a bad thing.
You lock your money in prison and IRAs and 401ks like they lock it up. If you try to touch your own money, you get slapped with 10% penalties and then you get taxed on it, which is high paying executives. That’s the worst thing.
In fact, you’re in the worst possible tax kind of a taxable income. You could be, which is ordinary income tax. Those 401ks and IRAs are ridiculous because you, all you’re, you don’t even have a tax advantage.
All you’re doing is you’re locking your money away. You’re deferring your income for a later date. Do you really trust that, that tax rates are going to be lower in the future than they are now with the Trump tax plan that just got passed?
I mean, we’re on one of the lowest tax brackets we’ve been in, in the 110 year history of the tax, the federal income tax. Why would we think in the future, we’re going to be in a better tax bracket? That’s, that’s just BS, right?
So we’re always taught to put our money in prison and lock it away, set it and forget it. And then somehow it’s going to work out. But what about the here and now, right?
What about today? What if you do lose that income stream, right? What happens down the road, if all of a sudden you’ve locked your money away and then you got to pay more in taxes than you would have if you just had that money work for you now, right?
And all those kinds of things. Nobody ever addressed that. Well, you’d be alive, you know, 10, 20, 30 years from now, right?
Do you know you’re going to be able to enjoy that money? All these what if scenarios, like people just plan your life in a calculator and your life is never meant to be that way. And so what I teach people instead is what about now?
Because everybody talks about future planning, but they never do present day planning. Like how can I actually plan for a good, prosperous present day so that even if I do get laid off, I’m okay. You know, give me an example.
I had a client where he is a, he worked for Hollywood and Hollywood, if you know, 2020 shut down half the year, right? 2022, they had a rider strike for half the year shut down for half the year. And that’s one of the most turbulent industries ever.
And, and fortunately that client started working with me like about 2018, 2019. And so instead of having his money locked up in his retirement plan, he got it out. And by the way, he wasn’t 60 yet.
So he was in his late forties, got that money out. And he says, I need to get this out of mutual funds. Let’s get it out and do something with it.
And that’s why I teach people is get lean, get liquid, get out, you know, make sure your wife’s student of money, but you don’t have to live on rice and beans to do it. That’s ridiculous. Get liquid means you have cash in your power and your control, not locked away from you.
And then get it out means get out to passive investments. So he did. He got it liquid.
And then he got it out. He bought several rental properties that he didn’t manage. Somebody else managed for him.
And, and right now, even though it was only a quarter million dollars he had invested that quarter million is now turned into about $4,000 a month passive income. Plus now just six years later, that quarter million now has turned into two thirds of a million of equity as a result. So he’s got all this equity.
He’s got 4,000 month coming in. He’s about to redo that’s where he could probably get up to 5,000 month, which was his whole goal in the first place. Right.
Most people don’t go for more. I had one client where he, he retired. He had, he was one of the top highest ranking generals in the state of California.
He retired, had a million dollars in his retirement plan. And then the financial advisor says, well, good. Now you’re 60 years old.
You can now live on 30,000 years. You pull off 3% a year, right? 4% rule was debunked a long time ago.
Now it’s 3%. If you’re in your sixties or if you’re in seventies, or if you’re trying to retire early and you’re trying to do with mutual funds, 2%. So this guy, he has a million dollars saved up.
He’s technically a millionaire. And he’s told he can live on $30,000 a year. Which he’s like, wait a minute.
There’s homeless guys that live on that in the state of California. Like you can’t live on 30,000 year in California. That’s impossible.
So that’s why he started looking around. He found our podcast eventually. And, and then when we started to diversify him into other things outside of wall street, more mainstream investing.
So like he did some things with apartment syndications. You know, he did some things in the oil and gas space, which I know you’re a fan of, right? He did some of that.
He even got a couple of duplexes that again, they were managed by somebody else that were out East where there’s better cashflow and things like that. And the next thing you know, his million wasn’t paying him 30,000 a year. Now he’s paying him over 130,000 a year.
What’s cool about that is, and not so cool, but what was the silver lining is he just passed away a few months ago. I found out he was 64 years old, but still instead of him making the excuse, like my dad did, which is he had to work longer and keep saving. And then he would have delayed it till he passed away.
He had four years of freedom, right? He had those four years where he was not only able to do what he wanted, like he actually started like volunteering, do some projects with the fire, the fire service, you know, with like wildfires and things like that in California. He actually took his kids to like different, different investor events, including things about oil and gas and try to teach his sons who are in their twenties, how to do what he was learning.
So he was able to pass on and create a bigger legacy. All by the time that finally, you know, just out of the blue, you know, he passed away with a heart attack and he was able to live those four years on his terms. I think that’s what’s so important is that you got to stop thinking that whole lock your money away, set and forget it, you know, dollar cause average, all that kind of dumb myths and fallacies that they teach you.
Instead, how do I get my money to work harder for me now? So I have to keep working so hard for that money.
[Melissa]
Money Rebels is on a mission to help professionals just like you get their money working harder for you. Their clients free up an average of $35,000 their very first year without having to work extra hours to show you how they’ve put together a powerful training called Cash Flow Secrets. And the listeners of the executive connect podcast can get it completely free.
Just visit MoneyRipples.com forward slash secrets and enter the promo code EXEC. Yeah, as you’re talking, it made me think you’re so right. I remember in high school, everybody kept saying, put your money to CD.
You get high, high interest rate. Put your money. So I did just that.
I put my, my college scholarship money in a CD. I’m like, okay, well, I’ll put it in. I’ve got a couple of months.
And then I went to take it out and they’re like, oh, you can’t take it out. I’m like, wait, it’s my money. And so you’re right.
You’re putting it in there. You may think that you’re getting higher interest rates, better tax deductions. But you know, back to, you know, my little financial knowledge that I knew in high school, it wasn’t the right fit.
And I think about, I want to, um, and I love that you mentioned Robert Kiyosaki because he was one of my first mentors back thing. I remember reading his, his cash flow quadrant and I was like, Oh my gosh, this is brilliant. And, uh, there’s so many nuggets in, um, in that book when I was in high school, that I really started setting myself up exactly how that, how that book said.
Uh, but I’m curious. Um, one of the things I’m curious about, and I love this, um, you call yourself the anti financial advisor. I think that’s so interesting.
Um, kind of what you alluded to the beginning, I always, you know, thought the financial advisors knew everything. They had to be rich. They had to be retired and they were just doing this because they enjoy talking about money.
So as you were saying that I was laughing because it wasn’t until I learned how much money in my first financial advisor had that I really understood. I’m like, you, you don’t have that much money. I was thinking they had millions and millions of millions of dollars, but they didn’t.
And so let’s unpack what the anti financial advisor is. What are traditional advisors getting wrong? And what do you like, what are your thoughts?
And what do you say is incentivizing them to keep their clients? I don’t want to say poor, but poor.
[Chris]
Yeah. Man. Well, I’ll start with this.
I mean, one big difference, you know, like I wore the wrong teacher for this one and for this question, but I have my teacher says cashflow equals freedom. That’s. You know, one of my things plus I love past income.
I have another teacher. I don’t wear as often because it creates a lot of little fights that says it’s like the dictionary says financial advisor, like a dictionary definition. Like noun person that’s paid to sell you crap, not make you more money.
Right. That’s really what financial advisors do again. Good hearted people, right?
Just like I was, you know, cause I used to be a financial advisor. I was doing that stuff. But what the problem is this is that it’s one, I think it’s fun.
And so I’ve got a lot of money I can take it and I can take it and I And so that’s kind of almost ethically borderline. That they can make money even when I don’t. For example, you put a million dollars with them.
They make their 1% and fees every year. They’re going to pay 10,000 bucks, whether you make money or not. Granted.
They could argue saying, well, if the market drops 20%, now you’re done at 800,000. I only make eight thousand off you. Yeah, but I lost 200,000 and you’re still getting paid eight thousand a year.
How’s that fair? right? And they’re really like, if you ever seen the movie, Robin Hood, Men in Tights, no Brooks film, right?
Yeah. Remember Blinken, you know, the blind guy, he’s up on the watchtower, like looking around. They’re like, Blinken, what are you doing?
He’s like, I’m guessing. I’m guessing no one’s coming. You know, and then he falls off the watchtower because he’s blind, right?
And, uh, and that’s what financial advisors do. They’re literally just guessing. They don’t know the future.
By the way, I mean, it’s not hard to become a financial advisor. As long as you have not robbed a bank, killed someone, and you can at least pass the test with 70%, you can become a financial advisor too. It’s not hard to do.
Um, that’s the, it’s such a, I mean, you could be a broke person as long as you can know how to pass a test and you can become a financial advisor. Like, I mean, I was out of college doing, I dropped out of college to become a financial advisor and it’s just not, it’s just not what makes you good. And unfortunately the people that do look very successful in that, that game, it’s not because they made lots of money.
It’s because they’re really good at selling you. They have a lot of money under management that gets them paid that regular stable income. Um, it’s interesting.
They teach you high risk, creates high returns. Well, if that were true, why don’t they take all the risk? What if they would say, I have to pay you money.
If you lose money, that’s never going to happen. No financial institution will ever do that. Nor will financial advisor.
So again, they’re not equally yoked with you. And here’s the other issues too. Um, they always teach you that everything’s always over promised under the liver, right?
For example, they teach the stock market 12% a year is what it’s made since 2000 BC. But the last 30 years, even though we’ve had the best run we’ve had the last 15 plus years that we’ve haven’t seen in history, still our average is like, I just did it today, 8.47% as of the end of August, 2025. That’s the 30 year average, not 12, not even 10.
8.47. That’s the best I’ve seen it in the 20 years I’ve been tracking it. So usually it’s between seven and 8%. So you’re guessing you put into this calculator is 12%.
You think, Oh, I should have this much money. Well, cool. That would be great if that were real, but it’s not.
Um, I just showed today in a webinar that, um, that even if you expected 12%, but you only got nine in 40 years, you would have only a third of the money you expected third. So that’s how much difference it is. That’s why so many people retire broke.
Uh, other statistics, fidelity has 45 million account users. Only 2 million have at least a million dollars. And of those trans America surveyed them said 35% thinks there’ll be a miracle before they ever was retired.
Because again, they can only pull off 3%, not more, right? Um, we got guys like Dave Ramsey thinking you could pull off 8% a year. I’ve run numbers on my own podcast that shows if you pull out 8%, you can be broken 15 years.
So that’s the other problem, right? Don’t listen to Dave Ramsey. Yes.
They’ve heard me say many times. Um, other things, inflation, you keep telling inflation is supposed to be around 2%, right? No, it’s not.
Go to shadow stats.com. You’ll find out the real inflation rates closer to 8 or 9%. So if you only get 8% of the market and inflation’s 8%, guess what?
You’re not getting ahead, right? You need, that’s why Robert Kiyosaki says, he’s like, you need at least 12 to 15% a year even to have hope of any kind of financial freedom because of that kind of stuff. Um, you know, so just all those little things, dollar cost averaging, right?
They say you just got to keep buying. Isn’t that the most brilliant marketing strategy you’ve ever heard of? Think about it.
Like when the market goes up, what do they tell you to do? Keep buying, right? Yeah, it’s going up.
Keep buying. Well, what happens when it goes down? What do they say?
[Melissa]
Keep buying, keep buying.
[Chris]
It’s on sale, right? You can dollar cost average. You’re going to be cheap.
Now, actually, I just have it here because I just did a reactive video on it. So this is actually the sheet. I don’t think you can really see it.
I used to share the sheet over 20 years ago. You can tell it’s definitely been through some weathering. Um, 20 years ago, I showed that I shared the sheet with other people and the crazy thing is always shows you like if the market goes down, you buy it dirt cheap, like a dollar, like the great depression, you would be rich.
Even if it went up to $4 a share, you know, if it went four times, you made way more money. Well, the thing is the stock market, the one they say doesn’t make you as much money. It looks more like this one, doesn’t it?
Like this one on the side, doesn’t look like this or this. It’s like this, it’s going up. Well, wouldn’t that mean if there were smart advisor to say, you know what?
Market’s way too overvalued right now. It’s on the buffet indicator. It’s over 200% where it should be.
You should wait till the market crashes and then just dump all your money. And then don’t say that. Don’t say, Hey, wait till, you know, 2009, 2010, and then throw your money in the market.
No, they’re like, just keep buying. Cause they’ll tell you this, um, this is what I learned. The three T’s clients like the time, the training or the temperament to be able to do their own trading, to do their own investing.
So that’s why they should just trust you. And that’s just bull. You know, the thing that stocks are the only way to go.
Wall Street’s the only way to go because that’s the only way they get paid. That’s legally the only thing they can show you. Even if they know better, they can’t show you anything outside of Wall Street because that’s what those licenses restrict them to doing.
They can’t say, Hey, you know what? You can actually make more money in real estate over here and probably have less risk, but I can’t show you that because my license says I can only show you this. So just all those things.
There’s just so many myths. I mean, I actually have been doing myths on my podcast. I’ve gone up over 20 different myths that people buy into, but you just got to understand the returns aren’t as good as mediocre returns, high risk.
You take all the risks while they don’t, which is why high risk rates, high returns is a fallacy, right? Dollar cost averaging doesn’t work. It’s false.
It’s completely false in the way that they teach it. And the truth is that really like it’s just not enough, right? Everything else is just overpromised and delivered.
And the proof is there, right? If only 2% of people in fidelity have at least a million dollars, and that’s not even enough to retire. You got to wonder, maybe I shouldn’t be doing the same thing that and expecting different results.
[Melissa]
Yeah, it’s funny. I just showed up in my, when I was reading about the wealth yesterday, 85% of the employees in video now are millionaires. Oh, and everybody that I think they have only a very small percent of their employees that aren’t because of their stocks, but that’s a very rare case, right?
In, in the stock market. So I want to talk a little bit about some of these wealth killing habits that are affecting smart people today. So even like I would consider, you know, myself and my friends savvy with financial investing, but let’s talk a little bit about what you call wealth killing strategies.
What are those and, and how can somebody spot those? So if they’re in a bad relationship with a financial advisor, they have all their money tied up. Like what are those, I guess, symptoms they can look for if they’re actually killing their wealth instead of growing their wealth?
[Chris]
Well, the question you have to ask yourself is what am I doing about creating wealth now? And I don’t mean what’s on a computer screen that doesn’t do anything for my day to day. For example, someone who walks their money up in 401k plans and stuff, it’s a negative 100% return.
You’re literally spending money only getting nothing in return for it in hopes that someday you’ll have something more, right? Which the reality is it’s just not what I see a lot of times happening is that I’ll see these again and again, every time people that are asset rich, cash poor, I think that’s probably the number one bad habit. Again, they’re always taught to lock money up in prison because that’s what every financial institution wants you to do.
Lock your money with them. So they make their guaranteed fees off of you, right? They’re making their money off of money under management.
I’m just advisors, the companies like Goldman Sachs and Merrill Lynch, they’re making money off of you just locking your money away and not touching it. Banks as well also make money when you pay off your debt faster. That’s one thing I realized as a mortgage broker.
I used to tell people as a mortgage broker, hey, you want to screw the banks and screw these mortgage companies, pay this off faster. But that’s exactly what they taught me to teach them. Why would they, why would those banks and those mortgage companies tell me to teach you to pay off faster?
In fact, you should do a 15 year mortgage because it’s cheaper interest rate, not a 30 year. Why are they incentivizing you with a 15 year mortgage instead of a 30 year mortgage? If they want you to stay in a 30 year, it’s a, well, I’ll charge you a little less interest because we’ll make more over time.
That’s not what banks do. They love acceleration and speed of money, velocity. We’re taught to accumulate money.
The accumulation theory has been broken for a long time. They don’t use accumulation. They use acceleration.
They want every dollar back because every dollar you give them, they can now loan out $10 more dollars. So if you pay, you know, that 15 year mortgage, like 10 year mortgage, you pay it down faster. They’re saying, thank you very much for that extra thousand bucks.
I can now land out $10,000 and I can now make more money off of you faster because I can go and lend it out at higher speeds. That’s how they make all their money. You know, and the truth is we can do the same thing, just in a different way.
It’s not like we’re going to borrow people’s money and then try to, you know, loan out 10 times more. No, that’s not what we do. But have you ever gotten a mortgage?
Have you ever, you know, tried to pay all cash for a property versus saying, you know what? I’m going to do a smaller down payment and then get a mortgage instead. You’re literally turned the rules back around on the banks.
Now you think the mortgage is in their benefit and yeah, there is a benefit to them. But the benefit is, what if I can keep that cash on my hand? Because for example, let’s just say you put 20% down on the house.
Let’s just say the house is worth 500,000. Now if that house appreciates 10%, that’s now up to $550,000. Now what most people will tell you, they’re like, okay, well I made 10%.
Yay. You know, right? And maybe that took several years to do it, but that’s not what you made.
If you put a 20% down payment, that was a hundred thousand dollars you put down. If now you’ve earned 50,000 of appreciation, your money that you had made a 50% return, you just got a five X multiplier on your cash, on that rate of return from that appreciation. That was something I remember hearing as a financial advisor.
I didn’t want to believe it because I was like, no, no, no, that’s not right. Cause I remember a real estate investor. He did a little, you know, dinner thing, you know, and he’s like, Hey, if you put $10,000 down on a hundred thousand property, it appreciates 10%.
You just made a hundred percent return. I’m like, yeah, impossible. No, I don’t believe it.
No, stocks are better. I have the charts to prove it might seem all these charts. And you put a dollar in 1928, look where it goes.
You got way more money with me than you put in a real estate property. What they weren’t showing is the fact that there’s a multiplier effect is you can create leverage like the banks do with you. You can do the same thing with them and create more leverage.
It doesn’t mean you go excessively in debt or anything like that, but I’ve seen this happen time and time again, cause here’s why. And this goes back to your question, Melissa, because many times I get guys that are successful. They’re, I wouldn’t say, I wouldn’t just say they’re investing or money savvy.
I mean, they’ve got some savviness, but they’re more very disciplined savers, right? Very good savers. For example, I had another client that was a, he was a doctor out in California and he, he was his whole plan was six years, a hundred percent debt free.
I’ll pay off my house and I’ll pay off my investment property. I’ll be free and clear. That was like his goal.
And he was stuffing money in his IRAs and 401ks too, right? Um, he was in his forties. Now I looked at his situation.
I said, listen, you’ve got a lot of equity here. Like this rental property, for example, how much, how much net profit you make on this property? $200 a month.
Okay. That’s not much. You got like a lot of equity in this property is like, yeah, but Chris, when I pay it off though, I’ll have 2,400 a month coming in.
I said, okay, that’s fine. Well, let’s go back to what you have currently. That’s in six years when you aggressively pay this thing down right now, you’re making $200 a month.
You have $700,000 of equity, 700,000. That means you’re making a 0.3% return on your equity. You could literally sell your property, that 700,000, cash it out, put it in a CD and do way better than what you’re doing right now.
It’s like, Oh, I can’t because that’s our first property. Like my wife and I love it. It took me two years to convince them to finally get rid of it.
He finally sold it. Luckily at the height of the market, he got a 700,000. He then bought like six rental properties out in Louisiana, bought all those properties.
And then he started taking the cashflow from those. He was already cash flowing 6,000 a month. So think about this.
He was trying to beg for this $200 a month, hoping to get to 2,400 a month. He finally listened to me. He was already making from day one, 6,000 a month.
He’s only mistake was he should have done it two years prior because then he reinvest the cashflow. And now he reached out last year and he said, Chris, I’m now up to over, over a hundred thousand a year on that money that was making me 200 a month. It’s now over a hundred thousand a year.
He was hoping and praying to make 28,000 29,000 a year. And now he’s over a hundred thousand, right? That’s the difference.
I had just yesterday a guy from Australia, same sort of thing. He’s like, he’s got like 2 million a net worth. And he literally has 600 a month coming in of passive income.
I said, we could sell off your property, get out your million dollars of equity, go and invest that even in the U S over here and make easily 80 to a hundred thousand dollars a year instead of 600 a month. He’s like, he’s like, well, is that net or gross? I’m like, that’s net.
I wouldn’t tell you gross. That’s a dumb thing. And he’s like, Oh, cause like, that’s the thing that was to promise in Australia.
I’m like, yeah, Australia sucks. That’s why Australians come invest in America. Cause they’re, they’re real estate’s horrible, but here it’s great.
You know, even, even now, even though it’s not amazing, you can still make so much better, like double digit returns. And so that’s the thing. Everybody thinks he got to lock your money up in prison.
Like what if he’d get it out, you know, just like that, that client that was in Hollywood, he got a quarter million out and he was able to generate now 4,000 a month from just that quarter million. I’ve got another client that had like $8 million to sit in my sidelines, which I’m like 8 million at 10% can make 800,000 a year. Now the guy makes millions.
He’s worth like $25 million, right? I was like, man, you have a financial advisor full time working for you, almost like a family office guy that still will talk about real estate deals or whatever. And he’ll even mention some things, but he has to do all he spends like 10 hours a week doing due diligence on all these deals.
I was like, we already have the group. You’re going to help with the due diligence. You can take minutes per week versus 10 hours a week.
And so like he’s already like in just like since April, the guy’s like freaking like gone gangbusters and already making a couple hundred thousand more a year of passive income, just getting started. So that’s the fun thing. Like when you start to realize that you’ve been taught to lock your money away and let other people make money off your money and stay, you take back that control and you’re the one that you use your, your brilliant brain, but you don’t have to be genius to do this.
You just have to spend a little bit of time and, and completely question everything you’ve been taught by financial advisors. Do the opposite. Hence anti-financial advisor, right?
Do the opposite. You actually make money here and now in the present day, not hopefully someday in the future as long as the market doesn’t tank on me right before I’m going to retire. I can finally touch that one.
[Melissa]
Yeah. I’m curious to get your insights. So, uh, in Austin, we, you know, the, the home homes were really expensive.
They’ve been very expensive. The interest rates are high. So let’s take one of your examples.
You have an executive making seven, $750 to a million a year income. And instead of plugging that money into like you were saying, 401ks IRAs is your recommendation that they buy a rental property in Austin with the money that they would be putting into a 401k or their savings account.
[Chris]
Oh, I’d stay away from Austin altogether. Almost anything in the Western half of the U S I would stay away from. And for the most part, and that’s the thing that’s interesting is that things shift, right?
There’s always good timing for different things. You would have asked me three, four years ago. Yeah.
Rental market was amazing, right? And you could make 12% cash on cash returns, not including appreciation, you know, buying down your more, you know, like paying down equity into your mortgage and stuff that your, cause your renters are paying your mortgage off, not you all that stuff. Tax benefits.
That was great back then. Now, not so much. Now you’re lucky to make five or 6% cash on cash return on a property.
But right now, lending is amazing. You can lend to anybody across the country and make 10, 12% a year off that you might not get tax benefits. You may not get huge growth, but you get good cashflow, right?
Um, and that’s the thing. The market shifts. It just depends.
You know, we talked about oil and gas, oil and gas. I mean, oil and gas right now, the prices stink, you know, it’s not great, but still we know that oil and gas prices will go up and that you can make a lot of money off that. And it diversifies you away from the typical stuff, even from real estate, you know, um, even, I mean, I have raw land.
I have a partnership where I have partners doing all this stuff with buying and selling raw land, my half a million or so that we’ve, we’ve invested over the last three to four years. He’s now kicking off almost 13,000 a month, you know? So like, again, like there’s, there’s always different timing of things to do.
Um, but no, I mean, coming to your question, like, what should they do with that cash? Well, one thing we often have our people do is like, first and foremost, instead of lock up at 401ks, yeah, you can get that money out and just invest it. Now, some people will say, well, what if I don’t have anything to invest in yet, or maybe I need to keep more cash on hand, but I hate the fact that the banks pay me 0.9%. Well, then we also use strategies like what I referred to as like max ROI infinite banking, where I can make 6% a year tax free on my cash, you know, and it’s protected from lawsuits and creditors by having it in a whole life insurance, very specifically designed. Don’t buy the traditional crap that’s out there. That stuff’s a ripoff, but there’s a way you can design it to where it’s like very cash rich, you know, and you can actually make much better returns.
And I can access it to make that money in two places at once by investing too. So there’s a lot of different ways you can save money instead of locking away in 401ks and IRAs. And then, and then of course, you have to go with whatever the government rules are at the time.
That’s the problem too. 401ks and IRAs, they change the rules. Anytime you have no say in the matter where I want my money in my control, I want to know that I can call the terms, not the government.
[Melissa]
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I think it’s, it’s interesting. And I think the other thing I always say is like the tax advantage of what you’re investing in. What are the tax advantages of the things I know for me, we optimize for tax as well, you know, for the higher income people, finding those investments that are going to optimize, you know, if you’re making seven 50 to a million dollars a year, you’re in a high tax bracket.
You need as many write offs as fast as possible because you’re paying the max amount of tax, which is then your biggest expense, way larger than your mortgage or any other bills that you have. So really optimizing for your tax situation. And so, I think that’s really key as well.
And I know, you know, I think one of the things that I think is interesting is there’s this kind of unique world going on with startups, the stock market, people that are exiting, you know, the tech exits that are going on right now. In my world, what advice would you give for the high income earners who feel like they’re hustling nonstop, but they feel like they aren’t free. So kind of what I was alluding to, you know, if they’re making seven 50 to a million, they’re really not making, you know, as much money as they they’re taking home because they’re in the top tax bracket.
So they need some, some strategies to help with that. So what would you suggest to them on how to maybe stop hustling so much and kind of building some of this residual income that we’re talking about today?
[Chris]
Yeah. I mean, one, stop funding those retirement plans, right? That’s a big one for sure.
Don’t lock your money up in that prison. You know, two, this is more of a warning. Beware of only investing for tax advantages.
I’ve seen so many people get duped into things and I’m not saying like, you know, what you’re talking about is that case, right? But so many times I’ve had people where the tax tail wags the dog, they’re just trying to save tax, but they’ll go into some really sketchy investments. You know, um, ATM funds is a good example, right?
Like I was telling people for years, I’m like, listen, like ATM funds fine, but I know we’re going digital here in the near future. Well, we want ATM funds or ATM type businesses where you buy an ATM, you get the depreciation and all that kind of business write off and people were making like 26% a year, you know, cashflow off of those things. And what happened last few years, they all go broke, right?
People lose lots and lots of money in those things because again, they were trying to say, Hey, I can make good cashflow and I get tax breaks. It’s the perfect combo. So don’t, don’t get duped just because it’s a tax benefit and make sure that the deal returns your money and then return on your money and tax ban is secondary, right?
So never let the tax tail wag the dog. The third thing I would also say too is, is, you know, really be careful where you put your money, you know, like make sure you’re putting your money in something that, that does have some more certainty behind it. I always tell people that boring is sexy, you know, and the more boring the investment is, the more I think it’s sexy, right?
That’s what my wife tells me about me all the time at least. So it must be good. I must be sexy.
But it’s true. Like, I mean, really, you want, you really want to make sure your money comes back and that’s the thing you have to be careful of. That’s just like that.
The guy mentioned that was like worth over $20 million. Like he was trying to do all the research himself, trying to figure out who was good. We were just, it’s funny cause we’re just sitting at lunch.
I went to visit him in Florida and he was just saying like, yeah, I’m like looking at these different deals. I’m like, Oh, well tell me about it. Like, who are you looking at?
He’s like, Oh, I’m looking at this company. And then this company, I’m like, Oh, actually I’m personal friends with the owner of that company. It’s legit.
Like that’s a good deal. He’s like, Oh, the good cause I’ve been looking at this thing for weeks trying to determine if it was good or not. I’m like, that’s the thing.
Like that one, I’ve noticed this is why you want to have good networks is that birds of a feather flock together. I’ll tell you, like the networks that I’m in, you usually won’t see the charlatans, the bad actors and the bad operators, people that are like just scamming people out of money. I just never run into those people because I’m not in those kinds of groups.
There are certain groups that attract those kinds of people. There’s a certain energy they give off while others don’t like, I tend to attract the people that are more like the nerds. Like they’re not good marketers.
They’re not good at like raising money. Um, but they’re really good at what they do. They’ve been doing it for, I’ll say this too.
If you’re looking at investments that are in the alternative space, I like people have been in the same space for at least 15 years. Like if they’ve been doing that, they’ve been through multiple market cycles with recessions and everything else. They’ve even had their teeth kicked in and learn from it and it got better, became better investors for it.
Those are the people I like. Um, I remember like apartment buildings were so popular going to 2020 and there were all these guys that would approach me. It’s like, Hey, refer your clients to us.
I’m like, great. Well, how long have you been doing this? You started in 2017.
I’m like, okay, everybody and their dog can make money in apartment buildings in 20, since 2017, you know, like what about when things go wrong? And those are the same people that are now bankrupt. Like after 2022, those guys are out of business, no longer even around, right?
So you got to make sure you’re finding somebody who’s got a great track record. If they, uh, they’ve only focused on their lane, they pick a lane and they just do really well at it, right? Like they just keep going.
Those are the people that I really, you know, give a much, I give a lot more credence to, uh, versus some people that like just are testing out the waters and they’re saying, Hey, whereas one, one operator told me, he’s like, yeah, I, I always do these vanilla deals that he’s done over and over again, but now I’m going to do chocolate deals. Instead of apartments, I’m going to do hotel conversions. I’m like, run, everybody run.
Like, don’t, don’t let him be your, give me, don’t let your money be beginning big, right? Like make sure you don’t do that. Go with somebody who has actually been time tested and has made it work and they have a system in place.
Even if the markets shift and change, you know that your money is safe.
[Melissa]
Yeah, I agree. I think, um, yeah, definitely don’t do an investment for just tax savings. I would agree with that as well because there are a lot of bad deals out there.
So I’m glad you brought that up. Um, for those that are trying to rewire, I guess, let me, let me say it a different way. So similar to what we were talking about in the beginning, we’re taught to get a job, max out your 401k, build a savings account, you know, all those things that we already have covered at length.
Um, but I feel like we need to do a little bit of the brain rewiring when we’ve been a W two employee. Um, it’s a whole different risk discussion. So how can those type of leaders start rewiring their thinking around money to prioritize financial freedom and I guess purpose for what’s next in their career?
And their goals.
[Chris]
And that’s the big thing I’ve been focusing on my money ripples podcast for the last couple of months is just all that rewiring have to do. You know, I say this started off, this is what got me, um, it got me, my, my dad, even though he was that person, like got the good job, saved everything, did everything right, but it just wasn’t enough, right? Even though he saved well, he saved like he was recommended to save, but it just didn’t end up being enough in reality because that’s the problem with over promised under delivered financial advisors.
But one thing he did teach me that was really good was look for evidence, look for real results, right? And that’s what got me to question everything as a financial advisor is I want real result, real results. Why can’t financial advisors really retire?
Not the money they’re earning off of you, but actually doing the investment they’ve been doing, unless they’ve made literally millions of dollars a year taking your money. And then they just pack them that away, right? That might be the only way they can do it, but not from a traditional average income standpoint, even if it’s more than average.
So understand that, you know, you look for evidence and the evidence is horribly against that whole, go to school, get a good job, right? Which is fine, right? But, but then keep putting your money away into retirement accounts, lock it away and pay, go debt free.
And you’ll be fine. If that really did work, why do I have so many of these poster children coming to us saying I need income. I have, I have all this, I’m asset rich, cash poor.
If that were, if it really did work, you wouldn’t see these people stressed out, but there are so many people stressed out because that net worth is worth less. And less becomes passive income. You’ve got to shift that perspective away from that net worth fallacy that they try to teach you.
That really is just, it does you no good if it’s not generating income for you.
[Melissa]
And I love what you said earlier. Um, I feel like you were reading into my mind here. I have a, a, a similar friend, your $700,000 friend with that much equity in their house, trying to pay off their house, pay off their house.
They don’t, they don’t want to sell their house because you know, is it a low interest rate and interest rates are never going back to the 4% that it was. So for those people that have those 4%, you know, interest rate loans and their house has doubled or tripled, what would you say to them right now when they’re struggling with, do I sell, do I stay, do I run to kind of discussion cause you’re right there. Cashflow is not there, right?
Versus what they can do with the money that’s sitting in equity. What would kind of be your final advice for those kind of people as we close up, know your priority, know what you really want.
[Chris]
I think that’s the big thing is what do you really want and why? So for example, I get so many clients are like, yeah, I’m paying off all my debt. I’m going to be debt free.
Okay. Why? Well, because then we’ll have a payment anymore.
Why is that important? Well, because it’s just less money coming out of pocket. I want, I want to be able to have that freedom, right?
I don’t want to have to make a payment and I rest my life. Okay. Well, you stuff to pay for toilet paper and food and taxes and insurance and everything else, right?
So are you going to get rid of everything? Like, no, I just want to get rid of that because I control it. I’m like, okay, cool.
That’s fine. In that itself is fine. But what is it you really want?
In many cases, it’s usually, they just want to have more than enough money coming in to pay all their bills and then some. Okay. Well, great.
Could we do something different? We do something that’s even better. What you’re thinking about, right?
Could it, could it be that we do sell your house? Would that be the priority? You know, do you really care about this house anyways?
So if you’re in your dream home, don’t sell the house. And if you get a 4% or less interest rate, great. Just don’t pay extra towards it, right?
Just keep paying your minimum payment, but see if you can take that cash elsewhere and make some more money. So it’s not just a eventually, eventually paid off house, but you got passive income coming in that can maybe more than pay off your house. What if we could do a cash out refinance that that money can be used to invest and then that actually pays you for mortgage payment for you.
What if that were like almost like paying off your house now, but you don’t have to pay off your house yet, right? Like there’s so many options that are there, but just know what you really want and why you want it. And the more clear you are on point Z, just like, you know, just like when you’re trying to put into a GPS, you know, your destination and you know where point A is, then we can figure out what’s the best route to get you there.
Unfortunately, most people take the long route, but a lot of times we can take a much quicker route to get there. It might just have to open up your mind to a different strategy than what you’ve been brainwashed to believe your entire life is the only way to go.
[Melissa]
So true. That’s so great. So many good insights today.
Chris, thank you so much for being here today and sharing your knowledge and your time with our listeners. What’s the best way for them to connect with you?
[Chris]
Everything’s money ripples, whether that’s money ripples.com, money ripples podcast or at money ripples on social media.
[Melissa]
I love it. Thank you so much again for being here. That’s the executive connect podcast.



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