I sat down with Chris Miles to unpack a question I see so many real estate entrepreneurs wrestle with: why does success still feel like a grind? In this conversation, we go deeper than doors and deal volume and talk about what actually creates freedom. Chris shares his journey from chasing scale to rebuilding around cash flow, liquidity, and true leverage after losing everything in the recession. If you’ve built something that looks successful on paper but still depends on you to run, this will help you rethink how you approach growth, income, and the role of support in your business.
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Hello everyone and welcome back. I’m Adrienne Green and today I have with me Chris Miles. Today we talk about how real estate entrepreneurs can escape the grind and create the freedom that they usually got into real estate for in the first place. So Chris, I’m excited to have a conversation about your life and how you escaped the grind and created some freedom.
Yeah, it’s gonna be a fun conversation. I can already tell.
So now to ground us, can you give us a quick snapshot of your real estate investing focus right now?
Yeah, I’m now more of a hands-off passive real estate investor at this point and various forms of real estate. Not just having turnkey rentals where I have property managers around the country that help take care of properties, but I also have things from raw land partnerships where somebody else is doing the raw land, but I finance it. I’m doing hard money lending and debt funds and things like that. Oil and gas, where I get paid on the lease of the land and things of that nature. So I do a pretty wide variety in the real estate space.
I love that and I love that you mentioned that you’re doing more passive hands-off investing because I feel like one of my little chips on my shoulders, sometimes people feel like it’s only about how many doors you have or how many you’re buying this year. And the truth is there are a million ways to invest in real estate. And honestly, when you are trying to escape the grind and create freedom, some passive real estate strategies are typically a part of that portfolio, if not the whole thing.
Yeah, I was told by a mentor a long time ago, it’s to fill your bank account, not your ego. And it’s fascinating because some people might know of Pace Morby. He’s been a little bit in the news lately, especially with his sub two type stuff that he’s been doing. But he’s been a friend of mine for several years and he came on my podcast a few years back and I did my opening talking about getting your money to work harder for you so you don’t have to work so hard for that money. And it hit him in a pretty sharp way.
And he said, Chris, I just heard the intro. I was trying to ask him about him. He’s like, I got to go back to this and ask you questions. Because the problem is I hear that intro and I’m not living that kind of life. He said, because I got in at first, the big milestone was a hundred doors. That was the big thing to hit. Then he hit the hundred doors and then he met a bunch of other real estate investors that have a thousand doors. So then it’s a thousand doors and then it has to be 10,000 doors. When does it ever stop? Maybe I could just go back to 50 doors and take care of all my needs and be happy and not have this massive huge team trying to manage all these doors because his ego was there.
And I think that’s the case. For me, I let that go quite a while ago when I nearly lost everything in the last recession during the global financial crisis. And so I was just like, I want the freedom. I want the time freedom. I want the money freedom that gives me that time freedom as a result.
Right.
Right, and like we were talking about before we hit record, you had the freedom that you could go to Tokyo to run a marathon.
Yeah, that’s right. I ran one of the world majors there in Tokyo just recently. So that was a lot of fun. It’s true. I do take that for granted. Sometimes I just think it’s like another business trip. But even just doing business and going here and there and everywhere. I remember my dad who was a penny pinching saver. We’ll probably talk about him in a little bit. But he was like,
I don’t even understand your life. That wasn’t me at all. For me, we didn’t travel much outside of Oregon and we didn’t travel much beyond the adjacent states. We didn’t fly anywhere growing up as kids. I remember he finally, when he empty nested, went to Mexico and Hawaii and things like that. But for him, just to hear me do all those things, it’s like I don’t even know that life. Because he was always just about trying to live cheap, almost like that Dave Ramsey type of lifestyle, to the point where it just kind of backfired.
penny pinching saver, post depression era mentality kind of guy. I remember several months back, I was telling him about some of the trips I was going on. He’s like,
I don’t even understand your life. That wasn’t me at all. For me, we didn’t travel much outside of Oregon and we didn’t travel much beyond the adjacent states. We didn’t fly anywhere growing up as kids. I remember he finally, when he empty nested, went to Mexico and Hawaii and things like that. But for him, just to hear me do all those things, it’s like I don’t even know that life. Because he was always just about trying to live cheap, almost like that Dave Ramsey type of lifestyle, to the point where it just kind of backfired.
And I’m thinking too of the generational shift that your dad was in. I know that it’s something I faced with my parents of the best thing to do is work for corporate. What could be better than having a title like VP at such and such company. And then they’ve got us entrepreneurial kids who have titles that we make up at our own businesses.
That’s true. I’m the anti-financial advisor. Most people are like, what is that. It’s a different game than the traditional path. It’s like Robert Kiyosaki talks about rich dad poor dad. His poor dad wanted that steady, stable job, that government job. If you go to school and get a good education, get good grades, you get a good job, and if you get a good job, then you’ll finally have a good retirement. My dad thought the same thing and it did not work out that way at all. It was very much like that poor dad type of story.
Right. And if you compare objectively stepping back from the lifestyle, very few flights growing up, staying around Oregon versus now you have this life where you can travel and go do all these big things and really have hobbies and dreams and the freedom to be a full person and not just an employee.
Absolutely. You’re in Vietnam right now. When I married my wife almost 10 years ago, one of the conditions was she said, I cannot do another Utah winter. She’s a tropics girl. So that’s why we picked every year to go travel and snowbird. We fly south for the winter.
And I was at first so nervous to do something like that because I had never left that environment. Especially when you have a whole bunch of kids, you don’t go anywhere. You don’t think you can take off time from your business. Then to see that happen in real life, where we took a couple months off and I still operated my business to a certain degree, I was still producing my podcast, but other than that, I was very low maintenance. Especially when you get to that point where I was financially independent the second time. It was a big leap of faith to say I’m going to travel and live somewhere for a few months. But now I can’t wait to do those kinds of things.
And now let’s get back to the real estate piece and how you got into all of this in the first place. It sounds like you’ve lived several lifetimes. We only have so much time, so I’m curious, how did you get to where you are today?
Yeah. Not the way I intended. Going to college, I was a sociology major with a potential triple minor in psychology, Japanese, and ballroom dancing. I was one of the nation’s top amateur ballroom dancers back in the day. While I was doing that, I realized after taking a lot of different classes that I loved social psychology and testing measurements. I actually love statistics. I wanted to go into business consulting.
But I figured if I’m going to do that, instead of just going and get an MBA and come out as an arrogant kid who has no experience, I would take a sabbatical. So I took a break from college for a year and tried to find some business to start. The first one that intrigued me was becoming a financial advisor because I figured worst case scenario, I learn about business and I learn about money and investing.
I got into it and I loved being an entrepreneur so much. It was 100 percent commission only and I loved it. So I never finished my degree. I dropped out of college and kept going down that path.
Four years in, I’m drinking the Kool-Aid. This is my mid to late twenties. I’m loving everything I’m teaching. I’m telling people if you just set and forget it, save a hundred dollars a month for the next 40 years, you’ll make 12 percent a year and be a millionaire.
After a while, my dad reaches out and says, are you going to advise me at some point?
My dad believed his job would kill him from the stress. He had strokes in his forties, heart attacks in his fifties. When I was in college, I came home and he was being rushed off in an ambulance telling me if I don’t make it back, there’s some money on top of the cupboard.
He came back, but I figured I’m going to sit down with him. This guy who is a penny pinching saver should have it figured out.
He’s 61 and says, I want to retire. What do I need to do?
I look at his finances for the first time. He’s 100 percent debt free, including his house. He’s been putting money in his 401k for decades.
I said, if you want to retire right now at 61, you’re going to need to die in about five or six years because you’ll run out of money.
There just wasn’t enough. This was 2005. The market hadn’t fully recovered yet.
He said, what do I need to do?
I said, I don’t know. You did everything right based on what I teach.
I walked away very bothered because I realized this is my future. I’m following the same path and it doesn’t work.
A month later, I’m talking with a friend I trained as a financial advisor who left to do real estate investing. He’s flipping properties and making money.
He says he and his dad doubled his dad’s income as a professor.
I said that’s impossible.
He asked me, how many of your clients are financially free?
None.
How many financial advisors are financially free from their investments?
None.
He said, there’s your problem.
He told me to read “Who Took My Money” and listen to a talk radio show.
I did, and I started questioning everything.
A few months later, I had a choice. Keep going or quit.
I quit.
I couldn’t teach something I didn’t believe in.
I became a mortgage broker and started learning real estate.
I was blown away. In the traditional world, you save everything and live on 3 percent later. If you have a million dollars, that’s $30,000 a year.
But with lending, that same million could produce $10,000 a month.
That’s when everything changed.
I realized I had been teaching people the wrong thing.
I turned my starter home into a rental. I started lending. By 28, I only needed $3,500 a month to live and I was making $4,000 to $5,000 a month.
Then the recession hit.
I got arrogant. I started buying bigger properties thinking leverage would multiply gains.
Instead, everything collapsed.
By 2008, I was a million dollars in debt and losing $15,000 a month.
I stopped teaching financial freedom because I wasn’t free.
I pivoted and started teaching people how to find money.
By 2009, things started to reverse. I slowly dug out of debt.
By December 2016, I was financially independent again at 39.
I love that and I love what we get from conversations like this, especially when people share both the peaks and the valleys. We can learn so much from both.
What I’d love to hear is your transition from active to passive.
Absolutely. When I first started, I had my starter home as a rental. I managed it myself and I was terrible at it. I let tenants slide on payments and eventually had to evict them. They trashed the house.
It was devastating.
That experience gave me a lot of fear around real estate.
When I came back in the mid-2010s, it was a leap of faith. I started with turnkey rentals with property managers.
One property, then another.
Then I expanded into other investments like debt funds and syndications.
Over time, I built confidence again.
And that’s how it works. You build the muscle by doing it one step at a time.
And then you start doubling down.
I teach something called the income avalanche. Once you hit a certain level of passive income, you reinvest it and it compounds into more income.
That’s when it gets exciting.
You also have to stay diversified and not rely on one operator.
I’ve done things like mineral rights and oil and gas after being cautious for years.
But I only do that once there’s enough liquidity.
You need at least $100,000 outside of your emergency fund before doing those kinds of investments.
I teach people to get lean, get liquid, and get out.
Get lean means understand your money.
Get liquid means have access to capital.
Get out means don’t lock your money in places that don’t produce income.
That shift changed everything for me.
It wasn’t about making more money. It was about creating consistent cash flow.
I love that because it highlights that it’s not just about building a portfolio, it’s about building one that supports your life.
Exactly.
A lot of people build something that still requires all their time.
That’s not freedom.
Right.
So what does your day-to-day look like now?
It’s completely different. Before, I was doing everything.
Now it’s oversight. Reviewing opportunities, making decisions, and letting others execute.
That’s the shift.
If your business depends on you, it’s not a business. It’s a job.
Exactly.
And that’s why you have to remove yourself from day-to-day operations.
That doesn’t mean you’re not involved. You’re just involved at a higher level.
And that’s where things change.
I love that because it ties back to creating freedom with your time.
Money is just a tool to create that.
If you’re making more money but have less time, that’s not a win.
Right.
So for someone earlier in their journey, what’s the first step?
Awareness.
Recognizing you can’t do everything forever.
Then identifying tasks that don’t require you.
Then finding the right people to take those off your plate.
That could be a property manager, a virtual assistant, or other team members.
The key is being willing to let go.
That’s hard for a lot of people.
They think no one can do it as well as they can.
Maybe not at first, but with the right systems and people, they can.
That’s how you grow.
Otherwise, you become the bottleneck.
Exactly.
Most people don’t have a scaling problem. They have a delegation problem.
Once you fix that, everything opens up.
I love that.
So where can people learn more about you?
The best place is my podcast, Money Ripples, and my website.
Perfect.
Thank you so much for coming on and sharing your story and your insights.
Absolutely. Thanks for having me.
And to everyone listening, thank you for being here.