Wake Up to Wealth - From Gypsy Living to Financial Freedom: Devon Ryan Johnson on Investing and Designing a Life of Wealth

Episode Date: April 10, 2026

In episode 60 of Wake Up to Wealth, Brandon Brittingham interviews powerhouse investor and entrepreneur Devon Ryan Johnson, who shares insights on the real, often challenging path to financial freedom—and why leadership, honest mentorship, intentional goal-setting, and authentic relationship-building are the cornerstones of scaling teams and wealth. Tune in for a masterclass in business, real estate, and living life by your own map.   SOCIAL MEDIA LINKS Brandon Brittingham Instagram: https://www.instagram.com/mailboxmoneyb/ Facebook: https://www.facebook.com/brandon.brittingham.1/   Devon Ryan Johnson Instagram: https://www.instagram.com/devonryanjohnson/ LinkedIn: https://www.linkedin.com/in/devonryanjohnson/   Facebook: https://www.facebook.com/devonryanjohnson/   WEBSITES Brandon Brittingham: https://www.brandonsbrain.org/home ========================== SUPPORT OUR SPONSORS: Rocketly: https://rocketly.ai/ Accruity: https://accruity.com/

This is Wake Up to Wealth, a podcast dedicated to helping you change the way you think about wealth. And now, here's your host, Brandon Brittingham. Hey, everybody, this next segment is brought to you by my good friends at Accruity. Now, if you run a business, most business owners neglect their back office, and they don't even know where to go or who to trust when it comes to their financials or CPA or taxes. That's where Accruity comes in. You can trust them. They can give you advice and they understand the back office. Listen, you're not running a business correctly if you don't have a hold of this and it's really hard to trust people that are out there. And most CPAs frankly work for the IRS and don't work for you. That's not the case with accruity. Check my good friends out at accruity for any needs that you have when it comes to helping with your back office, getting your book straight, getting your taxes correct. And they guide you and give you advice, which most firms don't. So check out my guys at a crudy, tell them I sent you. Hey, what's up everybody?

We are back with another episode of Wake Up to Wealth. And as I start the show, always, I just got to say thank you so much because as of today, we are number four in the United States on Apple Podcast. And if you look at the three shows that are ahead of us, they are huge studios, huge companies, huge brands, which is really cool because they've got insane buzz. budgets and huge corporate sponsors. And you guys continue making us make us one of the biggest shows in the country just off of bringing you guys really cool content and me getting to be able to bring really cool people on and teach you guys about investing in money. Which brings us to a guest today.

And one thing I'll say before I introduce her is this is how small the world is. So you should never burn bridges. we are in similar circles, and we got introduced by a mutual family office recently. And I was like, oh, my God, I recognize this name. We got on the phone. First thing I said is, dude, I've got to get you on the podcast. And it's just so cool that the serendipity of, when you climb the top of the mountain, you get to the top, it's the same people at the top.

And that's why you've got to be respectful and not. and bridges because when we get to the top of a mountain, we ain't going to let you up, motherfucker, if you do the wrong thing on the climb. And so it's pretty cool to have you on here today because we've been in similar circles for a really long time and we just got reconnected.

And Devin Johnson's here with us today. An extremely interesting background. Super cool person. Vived with her instantly because she's like me as far as she's going to show up how the fuck she wants. So I appreciate you coming on today.

I'm super excited. I will say one caveat to the don't burn, don't burn bridges is occasionally I will set them on fire intentionally. Yeah, that's different. Yeah. Totally different. Which is okay. Yeah. Sometimes that needs to happen. So tell for our listeners that don't know you, tell us about you, tell us about your background and then kind of lead us into what you're doing today. Yeah, I have a really, probably a really interesting background that it doesn't make any sense why I'm doing any of the things that I'm doing today. I always had the entrepreneurial bug. Even when I was like a little kid, I was always trying to figure out like how could I make money. I grew up in a divorced house.

Like we didn't have stability. We didn't have money. But I could see the neighbors over there. They had some money. And it seemed like they had choices. And we didn't. So I'm, you know, like babysitting. carrying groceries. So that bug was in me really early. And then I had a retail business in my 20s

that did really well, just like took off like gangbusters. It was a gourmet food business. I had no experience in retail. I just kind of had this idea. I thought it was cool. It took off. And I exited that business and I had some cash. And that's when I bought my first house to flip it. And that's when I really kind of was like, oh, I want to, I want to be an investor now instead of just like a retail store owner. So I bought the first house to flip it. And it was not nearly as much fun as it looked on HG. A lot harder, right? A lot harder.

Those bastards lied to me. Yeah. And I was like, I did everything myself. So it took me 18 months. It took me forever. I gave myself a black guy. It was like me on YouTube, crying on the phone to my dad. How do I use a tile saw by myself?

Like all of that kind of stuff. But I learned a ton. So I don't regret that I did it. But in hindsight, like I didn't really make any money on that project if you factor in how much time, headache, heartache, all of that that went into it. But that's what got me started in real estate. I got a real estate license, built a property management company. that really sucked.

That was awful. Like the worst thing I've ever done in my entire life. Because I thought the property management company was going to give me like residual income. That was the idea that I was going for. Oh, it will. It will. It's just not passive.

It's not passive and it'll give you heart palpitations from the first through the fifth of every month because the dog ate my homework and I can't pay my rent and somebody's mad at you all the time, whether it was the owner or the 10, minute and I'm also a recovering people pleaser. So that was like really fucking difficult that somebody was mad at me all the time. So I also was like working as a real estate agent. I ended up walking away and I started working for a fund. And I got a different kind of misery in that

experience where I started learning a lot, but I was, you know, it was a golden handcuff situation. I was making good money at my job. I hated my life. I was building up my rental portfolio. And then realized also, like, we were, I was selling a fake dream to people. We were telling them they could find financial freedom through buying rental properties. And that's bullshit. It doesn't work.

It breaks at scale. It's another job. It just became a nightmare. So I walked, after I, I, I left that company after a couple of years. I started getting hammered with people asking me, like, can you help me raise money? I'm like, I don't know if I do that. Can you help me with consulting on fundraising, investor relations and all this stuff?

And I was like, I don't know if I do any of that. A friend was working on a roll-up. Devin, you know lots of people. Can you help? Bibbidi-Bobbidi-boo, I raised $55 million. And then the light bulb came on. And I was like, oh, my skill set is actually. like relationships, you know, I get along really well with people and kind of understanding

what investors are looking for. And half the time, it's really just, it's the way that you communicate with them more than anything is what makes the big difference. So from there, you know, things just kind of took off. And I have a little investment community now that I've been running for a few years where I curate deals for people and I've been doing fundraising consulting for about four or five years now. And I've raised a lot of money. I've gotten a lot of capital commitments for the clients that I work for. And, you know, it was, I was the last person to think that I would ever be doing what I'm

doing now. I don't have a finance background. I didn't finish school. But being good with people can carry you so far. So I don't want to, I don't want to glance over this. You kind of said it very nonchalant. Hey, I raised $55 million. And because you're, you know, it's your zone of genius.

You're good at it. Like, go unpack that for me a little bit. Like, how in the hell did you do that? And you probably raised more than that now. But like, how did you, how did you get? I mean, for those of you that are listening to this that maybe don't understand the money raising world, that is not easy. like by no stretch of the imagination is that easy?

I think honestly, part of the unfair advantage that I had is number one, I didn't know that it was supposed to be hard. So say when I had my retail business, that was like 2008, the economy was in the toilet. And I was just so ignorant that I didn't know I was supposed to be scared. I just had a great idea and I was going to go for it. So in that case, yeah, the friend that was working on the roll-up just said, hey, you know, do you know anybody that could help? And I started calling people, hey, I have a friend that's working on this project.

I don't really understand all of these words that he just said me, that he just said to me, like some of the terms and stuff. I didn't understand. But I started calling friends and, you know, One of those friends said, oh, yeah, I have a family office that likes to invest in those kinds of deals. And then that was that. So my role was not, I hunt the buffalo. I don't make the sausage, right? Like, I get the doors open.

I get the doors open. And this might be controversial, but I'm friendly, bubbly, pretty girl with purple hair. like I can get doors open and that's a little bit of my unfair advantage it's pretty privileged. I hate to say it, but it's true. And I also know what is not my place, which is like I don't need to be in the middle of all of the negotiations of the terms and the governance and like that's none of my freaking business. I don't belong there.

But what I can do is get the conversation started. So frequently when people ask me like, what do I do? I say that I'm a matchmaker. right? Because that's what I really, y'all got a date and see if you actually like each other and all of that. But I can, I can bring some suitors to the table. Yeah. What do you think, what is one of the kind of, to kind of go through this transition you've gone through, right? Like brokerage, property management, having another business, raise a money to where you are now. what do you think is kind of like a piece of advice that you would give to anyone listening to this of like you've you've had multiple iterations that you've obviously been successful at?

What do you think is one of the biggest pieces of advice that's helped you get to where you are? I have a really high tolerance for pain. Like an abnormally. A huge believer in that. Yeah, I have an abnormally high tolerance for pain. I have delusionally huge ambitions. I think that has served me a ton. And I, like, I move.

I just keep moving, even if I don't know what I'm doing. I frequently tell people, too, that I don't know what I'm doing. So, like, one of the, it's honesty. One of the private clients that I did. help with quite a few rounds of fundraising in the last couple of years. Guy is brilliant, one of the most brilliant tech founders I've ever met in my entire life. Somehow I ended up on a call. He tells me about this company that he's trying to buy. It's a public company, so I need 170 million bucks, but you can't tell anybody what I'm buying because it's a private company

and just like all of this super technical stuff that I didn't understand at all. And I'm sitting on the call like, I have no idea how the fuck I got here. Like, this guy has, this guy has no idea that I am completely unqualified. Right. Right. To be on the call. But I said to myself, like, I just got offered a chance to sit on a rocket ship. And I could totally fuck it up.

But like, I'm going to go for it. Even if I fall flat on my face, like, I'm just going to go for it. he ended up not buying that company because the stock started running, but I got him a term sheet somehow. Don't fucking know. And then he was like, hey, I've got some other things I'm working on. Like, do you want to help me out with some of those? So that's probably another piece of advice too is like if you're transparent with people

about what you can and can't actually do, but you're confident in your willingness and ability to just like try and take swings at it, you can get a ton of opportunities. I think where people mess up is they act like they can, if they're like, if they say they can do things that they're not actually totally sure that they can and you stick your foot in your mouth, that's totally different than saying, I have no idea if I can pull this off,

but I'm going to give it everything I got. Yep, 100%. Yeah, that's great advice. So obviously, you were not taught about money, right? Which most of us weren't. And so you've kind of learned. And in the last conversation that you and I had,

which I think is really intriguing, and I want you to share this, is you kind of were like, well, because what happens is, right, I raise money. I run funds and somebody to reach out to me and they're like, hey, I want to invest. And but they typically are clueless as to what they want to invest in or why. And when you and I talked last time, which I thought was really awesome, like you kind of led with this framework. Yeah.

And I think it's very important and powerful for my listeners to hear that. I love for you to share that. Yeah. I call it the investor fit filter. And I stumbled into this light bulb on accident from all of the mistakes that I had made over the years. There have been multiple times where I found myself over indexed on equity and I had no cash flow. And now I'm digging for change out of my designer handbag too. My portfolio looks great.

So what I learned the hard way is the most important question, if you're thinking about making any investments, is start first with what do I want this investment to do for me? Start there. The asset class doesn't matter. It doesn't matter if it's real estate, oil and gas, crypto, M&A, or whatever the fuck else is trending on TikTok today. Right? What's the primary question is, what do I want this investment to do for me? And there are basically six, There's six categories. Cash flow, pretty obvious. I'm looking for monthly or quarterly distributions. Second, growth. I'm thinking about the longer term three, five, ten years down the road. Number three, liquidity. I need to know that, number one, this money is productive, but also, if I need

access to it, it's not locked up in something for five, ten, fifteen years. Number four is impact. We want all of our dollars, you know, all of our investment dollars collectively, they have a job to make a return. But similar to kind of like a football team, every player on the team has a different thing that they're doing, right? So when it comes to impact, like, yes, I still want to make a return, but I also want to know that I'm, my dollars are doing something in the world, right? Is it green energy or, you know, it could be revolutionary medical research. or anything along those lines. The fifth is tax strategy, obvious, you know, right? Like, I want to get some kind of tax advantage from this investment. And they're not all created equal. You got to also look at, like, are we talking about active income or passive income? Because there are deals that will

help with active income and deals that will help with passive income. And then the sixth is return on joy, right? We're all going to fucking die someday. it's going to happen. And right now I'm sitting in my return on joy. I live in Costa Rica and I rent the place out when I'm not here. It doesn't really make money, but I don't care because of what it does for my heart and my spirit. Like you can't quantify that. But where I made mistakes, oh, sorry.

No, go ahead. Where I've made mistakes was investing in whatever was trending without asking the question of why. There was a huge rush of Airbnb's years ago. Great. But like why do you want to get into Airbnb? Is it because you want a lifestyle asset, like a beach house that pays for itself? Or is it because you want cash flow or tax advantages? Because those are completely different ways of thinking.

And that's an excellent. I mean, those are all great things. And that is a, that is a, I can't say that I've ever heard that. Like I've never had someone walk through that. matrix of investing, which I think is number one, brilliant, but I think there's a true reality to that. And I think to your point, I think you should have a basket of kind of all of it, right? Like when you walk through that, I think there should be a basket of all of it. What do you think also, obviously you've got a PhD in money now? Like, what do you, what do you

think is like, it's just, it's so strange to me and it still baffles me how many, you're people are just uneducated about getting on this side of the world, you know, what do you think that stems from? And what would be your advice for somebody that's listened to this of like, and I do think sometimes for the average person, it's overwhelming. It's like, holy shit, I got to think about all this stuff. But it actually, when you boil it down to just the example you gave, it can actually be really simple. Yeah. A lot of stuff is gate kept. and whether intentional or unintentional. And along with that framework,

I kind of feel like part of my mission in life is to democratize access to private deals. First, you've got to know what the hell it is that you're looking at them for. What do I want? And then there's not so much noise. Then you don't feel like you need to research 87,000 different things.

And I actually categorize investments by those six, categories. But a lot of information has been gate kept, or it's just not accessible. Because of private deals, like I get hammered. I know you get hammered with opportunities all the time. The average investor, if you're like a dentist in Ohio, you got 500 G's, a couple million bucks, maybe to invest. They're not going to get hammered the way that you and I are with opportunities. They don't get to see them. And then they get so overwhelmed with this or that asset class, this or that thing,

what should I do that they don't have their, they don't have their primary purpose of the investment figured out first. I think that really just helps to simplify things first. If you know what the hell you're doing, this is my plan. then the noise gets quieter. I'm glad you led with his gate kept, because I love to say this. My grandfather was a country dude. It was wise beyond his years.

And he used to say, one of my favorite things he used to say is they muddy the water so you think it's deep. And I think it's with a lot of investment vehicles, with a lot of Wall Street things with a lot of things. There's terminology and shit that really when you boil it down, it's just, it's just an investment. And it makes it sound so complicated and difficult.

And when you actually get behind it and understand it, it's actually really not that difficult. And a lot of people don't realize that you can invest your money safely, get a good return. And over time, that compounds, and that will change your life financially. You don't have to do anything fucking crazy. or wild, right? Yeah. And I think that's one of the biggest misconceptions people have.

So I'm glad you said that because I also always say there's two economies in this world and it's the educated and the non-educated. And educated not like you went to college because I didn't go to college, did you? For a little bit. I didn't finish. Yeah. There you go. Exactly.

But I got educated on money. And there's people that are friends of mine that have Ivy League. educations but are still not educated on money. So if you're listening to the show, one of the big things I always stress is you got to learn about money and it's not the way we've been taught. Oh, no, not at all. If you follow what is like, you know, recommended by society to do, you're kind of fucked.

100%. Another question I want to ask you and then, well, I'm going to go to the final wrap up question that we always do is, I think it's really cool that you live in Costa Rica. Like, how did you end up there and why? After I got out of that job that was sucking the life out of me, I just started living like a gypsy. I always wanted to travel. And a lot of the things that I was doing through my 20s and 30s was I was trying to get to a

place where I could afford to travel and live the life. of my dreams. And when I got out of that job, I was like, what the, what am I waiting for? Why don't I just go do it? So everything that I do today, everything that I've built today, I have multiple businesses, you know, I have a fund. I've got the investor community. I do my consulting. I've constructed everything in a way where I have total location freedom. So for a couple of years, I just lived like a gypsy. I'd go spend a month in Morocco, a couple of months in Bali, going here, there and everywhere. And I just kept coming back to this one little surf town

and decided, you know, being a total gypsy is fun for about two years. But then you start to feel like I need some kind of roots. And there's like, they don't believe in stress in Costa Rica. Yeah. Yeah. It just, it doesn't exist here, you know? Yeah, I, you know, it's a good point is to, you know,

we kind of have this hustle work culture inside the United States, which, you know, we've both been sucked into. You know, get outside of this country and it's good for you because you'll see the rest of the world views, work, money, everything a lot different than we do. And it's good to get that perspective. Totally. And for me, ultimately, the money, the purpose of the money is to live the life that I want. Right?

Absolutely. I realized that I could actually start living the life that I wanted a lot sooner. Like, I'm not taking a private jet everywhere, right? But I still, I control where I do, what I do. I go surfing. I live in paradise. And that has given me so much of that return on joy, too, that it's like, in general, I think a lot of the things that people really want to do in life, like we make it so much

bigger and harder in our head than it really is. And who's to say that you can't work in finance and live like a gypsy and have purple hair and all that if you want to, you know, just like make the decision to do the thing that you really want to do. And I think after getting out of the job that had made me just made me so miserable, I just did a massive pendulum swing of like, okay, fuck, I'm just not going to do. do, I'm just tired of, I'm tired of people pleasing and being accommodating and not doing it anymore.

So, you know, that's fucking awesome. But I think a point that needs to be made on this, because I think it's extremely powerful for people listening to this, you had some extreme intentionality behind this, right? Like you thought about it. You took the time to think about it and you said, I'm going to design my. a life where I can still figure out the money part, but I'm going to live where the fuck I want to live and do what I want to do. And I think you obviously had a navigation and a map in your head to do it.

And then you constructed it into your life. And I think one of the biggest, and I'm making a point about this because I think it's so powerful. I think a lot of time with entrepreneurs, their only map and guide is money. Right? It's like, well, if I make a certain amount of money, then and then the false narrative is, is then you, if you're good, you end up getting it. And then you're like, well, fuck, now what?

I'm not happy. Right? And so I think it's a powerful and it's why I asked you because I thought that this is the answer I would get that if you're listening to this, you can build the life of design that you want, number one. You can figure out the money. Number two, but you have to have some intentionality behind it that you actually go out and do it and not just talk about it.

I think a lot of people, they've never given themselves permission to want what they truly want. That's powerful. Just start there. If nobody was watching, if nobody was judging, if nobody was judging, if there was nothing to prove to anybody, what is it that you really want? and then like what is stopping you from from going for it you know i don't know kind of get a little off on a tangent what everybody's like different spiritual beliefs and stuff are like this is i don't remember having any other lives so why why am i not going to just like go for it in this one with whatever that might be for me for somebody else it might be they just want to play

golf on Tuesday and live in the suburbs. And if that's what you want, then just go fucking do that. You know, I want to climb mountains and I like jumping out of planes and, you know, doing all kinds of weird, bizarreo adventures. That's what gives me joy. Yeah, that's awesome. I could talk to you all day, but I do want to ask you one more question before we wrap. So what do you, so tell us what you're doing now because I think you're doing some pretty cool shit right now, too. Uh, yeah, I've, um, so yes, I do fundraising consulting. I don't take on a ton of clients,

but for people that if they need help, half the time, it's not even so much that they don't have the right connections. It's, they don't know how to tell their story, right, which if you can't start there, it doesn't matter how many investors you talk to, like, you're not going to get anywhere. So, um, so I do some consulting. And then, uh, my group, the Capital Club, is growing exponentially. And that's a great place for any investors that are like, they're looking for deals. They want them organized by those purposes. And then I also, I have a fund that we just launched at the end of last year, Quant Fund.

It's not, no tax advantages. This is about, you know, cash flow and long-term growth. Basically, just like printing money. That's awesome. Awesome, awesome stuff today. So I ask everybody the same question. And I'm actually very interested in your answer to this. So I call the show Wake Up to Wealth. And it's because like a lot of entrepreneurs, I grew up poor. And I was always told things about money from my parents and grandparents that weren't true. Nothing wrong with that. They did the best they could with the information that they had. But when I got into rooms that, like you've, been in and I've been in and I got around people that had real wealth and real money, I got an education around money that was completely different. And so I call this show Wake Up to Wealth for two reasons.

One, I want everyone to wake up and understand what money really is and understand the science of money and really how your world can change when you understand it. And then number two, I actually want people to wake up one day and be wealthy. And waking up to wealth is different for everyone. and ask everyone the same question at the end of the show, what does waking up to wealth mean to you? It is sovereignty, meaning today I choose what I do,

with whom for how long and where. You know, that's, to me, that's true wealth, is I have the freedom of choice. what am I going to do today? Fair enough. That's a good enough answer for me. If anyone's listening to this and they want to reach out to you, check you out, where can they find you? Yeah, I've, Instagram, at Devin Ryan Johnson is probably the most accurate depiction of my life.

And then the Capital Club.com.com. That stuff that I shared about the framework and all of that, we put together some free information if anybody wants a little more help. Like, how do I learn to think that way? But yeah, social media, Devin Ryan Johnson, there's not a ton out there about me. I've been a little incognito. We might have to change that. Yeah, yeah.

Well, and we're going to put the, she was, she told me before we got on here that, for we're going to put this in the show notes, kind of the framework. She's being gracious enough to give that to it. our audience, so I appreciate that. Number one, I knew I was excited about this because I just, I knew the, the gems you would drop. So I'm very grateful that you came on here today and shared with my audience. Thank you for your time. And thank you so much for coming on here and pouring into my folks. Thank you. It's been absolutely my pleasure. It's fun conversation. Hey, this next segment is brought to you, but my good friends at rockately.a.I. That is Rocketley,

If you're in the real estate business, especially the investment side, and you need a platform that can run your real estate business and talk to leads through AI when you're not able to talk to them and can qualify and get to all the leads you can't get to, plus it has an amazing piece of technology with it called lead detector that helps get all the people that come to your site and not opt in to opt in to turn into a lead. these are my good friends at rocketly.com. A.I'm part of this company as well. I use it to run my real estate business, my real estate investment business. Go check them out. Again, rocketly.com. And thank you guys for sponsoring the segment. Thanks so much for tuning into this episode of

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