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If you'd like information on how you can join, please go to RadicalPersonalFinance.com/patron. So you got a bunch of kids, that means automatically that your life is finished, right? You know, you got six kids, so you need to buckle down and live where you don't wanna live and, you know, take 'em, have a big house with a big mortgage and work a job that you don't wanna work simply to support your family, right?

Sorry, not true. These are choices. My guest today, he and his wife have six kids and they're living on the road full-time, traveling the world with their entire family. It's pretty cool. (upbeat music) Welcome to the Radical Personal Finance podcast. My name is Joshua Sheets and today is Wednesday, Tuesday.

Today is Tuesday, Tuesday, February 24, 2015. (Joshua laughs) I don't wanna miss a day, I don't wanna get to another day. Today is Tuesday and my guest is an awesome guy. I think you're gonna like him. His name is Greg Danning and he and his wife, Rachel, are doing exactly that.

They're living on the road with their six kids. (upbeat music) I've been watching Greg and Rachel's website for years now. Their primary website is a site called discovershareinspire.com and it's just fascinated me. The lifestyle they've been able to build for themselves and I think you're really gonna enjoy this.

Showing how you can build a life. That, I mean, I don't even need to go into it anymore. You can build a lifestyle that's your choice. It's your choice and that's what we talk about on this show every day. Choose the life that you wanna live and live it and there's all kinds of aspects to that which is what we talk about.

We talk about the technical aspects of it. How do you actually technically accomplish it? How do you accomplish it in an efficient way? There's also the aspects of inspiration and encouragement and understanding how to go about things and understanding, frankly, that you have the permission to design things the way that you'd like to design them.

And one of the things that oftentimes holds people back is kids which is, or excuse me, it's not an actually hold people back. People feel like they're being held back is by their kids and that was one of the reasons why I wanted to bring Greg on the show to share this story.

Greg's an awesome guy. Again, he and his wife, Rachel, they have six kids, they're living on the road. He is one of the most enthusiastic people that I know and as you'll hear in the interview, it's not a front. Don't be, he actually is this enthusiastic all the time.

But you know what? I'll just let him share his story with you. Greg, welcome to the Radical Personal Finance Podcast. I appreciate you being with me. - Oh, I'm excited to be here. Thanks for having me. - So dude, you are a radical kind of guy and I think you wear that badge pretty proudly but you certainly don't fall into the norms of society in just about any way, do you?

- No, I was actually thinking about that the other day. I'm like, you know, I'm pretty unconventional and kind of out there. So yeah, it'll be fun. It'll be really fun to talk about. I think some of the things I might have to share might cause some thought and some, to see things a little differently.

- Well good, that's what we're all about. So kick it off. I'd love to hear a little bit of your story with how you went from wherever you started to living this crazy lifestyle with your whole family on the road full time. - Yeah, it's actually a really great story.

I grew up in a broken home. I ended up out on my own at an early age and sometimes with little to eat and nowhere to stay. And we went through some really hard years and so kind of fought through that. I knew I didn't want to stay in that kind of situation or that kind of poverty or ignorance or anything.

I really wanted to create a great life. You know, and you see people and you're like, hey man, they're living a great life. If it's doable, I can do it. So I really went after it, you know, and kind of set a course of, you know, go to school, get good grades, get a degree, get a good job, and we settled into that.

I had a great job and we, you know, picked up our mortgage and bought a little house and we're living, you know, the little American dream that it's kind of prescribed. And honestly, it was really good. We had a good life and we just kept reading and reading. My wife and I are voracious readers and learners and we came across some other ideas, you know, and some unconventional ideas.

And at first you kind of reject it like, that's crazy, you can't do that. And we started to think differently and made some investments and did some different things and kind of, you know, really felt strongly that we wanted to go out into developing countries and try to make a difference, you know.

I'd been through some tough times and I'd spent some time in Peru before I got married and thought, you know, honey, let's see if we can do this. And so several years ago, we did, okay, we're gonna go for it. We're gonna quit the paycheck that comes every other week and we're gonna sell our house and we're gonna sell our stuff and we're gonna try to live a different lifestyle.

And it has just been one amazing adventure, ups and downs, but it's absolutely incredible. And so together, we have six children now. We started out with four kids and, you know, went and lived in Central America and then in the Caribbean and Dominican Republic. Then we went to India.

Then we've driven really slow kind of overland travel through Alaska, the Yukon, Canada, the US, Mexico, Belize, Guatemala and Nicaragua and now in Costa Rica again where we're living now. And so it's been an absolutely wonderful journey and really unconventional, kind of crazy, but for us, it's been our dream and it's really been a wonderful, wonderful experience.

- Why do you wanna live this kind of lifestyle? - You know, it kind of resonates to live deliberately and that's what Rachel and I like to say. We wanna live consciously and deliberately. We really resist what for us would be a humdrum existence. And man, I wanna be really, really clear.

I don't recommend my life to anybody else. I just, I recommend that people live their dream, live their life, not my dream, but I say, you know, live your dream, whatever it is, live it. And for us, this is our dream. We wanna see this beautiful world and try to have a positive difference.

We wanna have new experiences and grow and learn. Every time we go somewhere new, I feel like I've come back a better person. Like I've learned something and grown. And I just feel, I guess if I could just sum it up, I feel alive. I don't wanna get up and dread my life.

Dread, I don't wanna go to a job I don't like. I don't wanna just live just to pay the bills. I wanna live deliberately. - How, when you originally set out and decided that travel was gonna play a big role in at least your dreams and then you were gonna try to build it into your lifestyle, were you rich?

- Whew, no. (laughs) But you know what, I bought into the idea that you had to have lots of money in order to travel. And so we had quite a bit of savings and I had some investments in the stock market and in real estate. And so we went out initially that way and we were spending a lot of money and we had expenses back home.

And then ended up, you know, when things kind of tightened up a little bit in 2007, 2008, we lost almost all of our investments. And so we had to refocus, we had to go back. And I'm grateful it happened because it forced us to question a few assumptions and a few common beliefs there and to revisit what's really necessary and what we really wanted as far as owning stuff and things and consumerism and what kind of lifestyle we wanted to live.

And so, I really went back to the drawing board and revisited that and so, no, you know, there's a different way to do it and you don't have to be rich. To live your lifestyle, there's other ways to do it. Being rich is great, it's wonderful. And there's a way to do that as well but you don't have to be rich to live an unconventional lifestyle.

- What did you do differently after your investments declined in value? What did you do differently from what you were doing before? - We became, in a way, minimalists. (laughing) We just thought, wait a minute, okay, you know, if we can clear out, I don't know, we just kind of came to the realization that everything you own or are buying or everything you have in your possession takes up thought or time or space or attention.

You have to move it, clean it, insure it, take care of it, pay for it, fix it up. I mean, everything you have. And so, we kind of moved to this idea of, let's keep the stuff that really brings great value in our life and let's get rid of everything else.

And so, we're not a kind of minimalist like sell everything and walk around in a loincloth and have nothing. But more so of, if it doesn't add real value to the kind of life we want to live or it ends up taking away time, attention, or resources from the kind of life we wanna live, then we're better off not having it.

And so, we got rid of the stuff and we don't acquire much. We try to keep it real simple but we live, we still live comfortably. I still have my MacBook Pro and my iPhone 6 and this microphone I'm talking into. I still got things that from work or for passion and purpose we use.

But other than that, we try to live really simply. - What have you learned in trying to do that with kids? This seems to be the challenge. My wife and I, we have two kids. One is 18 months old and the other is on the way coming this summer.

And one of the challenges is, and I know you, how old are your kids at this point? - So, first of all, congratulations. That's awesome. - Thanks. - Oh, and man, 18 months is fun, fun, fun. It's busy. So, my oldest is 12 and my youngest is, she just turned one.

- So, you have them right in that stage is all the way from the one where there's all of the paraphernalia for we little ones to, I guess, just kids all along the way. And one of the biggest challenges, my wife and I are also aspiring minimalists. So, we try to keep just things simple.

But man, at least in the US, kids come with a lot of stuff. Was your secret just to move out of the US where kids don't come with that much stuff? Or what strategies do you have to live this kind of lifestyle with kids? - No, you're right. It's kind of funny.

So, we've been back and forth. Well, I haven't been back in the States now. Well, I go back for visits and things. I go to speak and go to conferences and things like that. But living in the States, the last place we lived was Alaska. And that's kind of different.

It's kind of like its own country up there, which is really cool. I like Alaska a lot. But no, so I guess living in what the Alaskans call the lower 48, it's been a while. And yeah, we were practicing minimalists there too. And it was really, really funny. The neighbors would feel sorry for us.

And they would, like literally, they'd be like, "Hey, do you want us to buy some things for your kids?" (laughing) And we're like, "No, no, no, no, no. "No, you're misunderstanding. "We're not a charity project here. "We're doing this purposely. "We don't have a lot of stuff." And yeah, it's easier abroad, I think.

But to get caught up, a lot of us get caught up, we get consumed by consumerism, I like to say. And we get the stuff and the thing. And there's always an exchange rate for that. What we've found though, is the less we have in toys and gadgets and big bags and piles of things for the kids, the more creative they are, the more time they spend with each other and outdoors, which we're big, big advocates for spending time outdoors.

And they'll be so creative. We'll buy them, like our little ones love to do clay and they'll make these amazing creations. I mean, it's some incredible stuff. And they spend more time painting and drawing and practicing musical instruments and building things with their hands and playing outside. And for us, that's a lot of value.

Now, they still get on the iPad and they like to do their studies on there and some of those other things. But we found that even if we keep it simple with them, it makes their life more simple and more real. You know what I'm saying? And so you're more connected as a family and more connected to the people around you.

- So explain to me your trip so far. You started in Alaska and you just drove south or where have you gone and where are you going at this point with your family? - Yeah. So this was crazy. We were in India helping people who have leprosy. And it was just such Southern India out in the rural, way out in the middle of nowhere.

It was such a special experience. And we got pregnant with number five, Atlas. And we debated whether to have him over in India. It's pretty different over there. India's pretty different. I really love it. It's quite different. So we ended up, we said, you know, let's go back to the States somewhere and it just worked out to come back to have the baby.

And so we thought, where should we go? Well, my mother-in-law had just moved to Alaska and neither of us had been there. We thought, boy, let's go to Alaska. So our flight was into Atlanta, Georgia. We got off within two days. I'd bought a van for our family and we drove across the US and up the Alcan Highway up to through Canada, British Columbia and Alberta and the Yukon, Alaska.

Oh, it was wonderful. - Were you heading for a job or just, you decided we'll go and figure it out when we get there? - Yeah, just figured out when we get there. So we went up there and just, I mean, the goal was to experience Alaska and have a baby up there.

So we got up there, ended up spending a year, had a really great experience, just love Alaska. And then we said, you know what, where do we go next? And we were, we were trying, you know, Thailand was on the radar and Columbia was on the radar. And we thought, you know what?

We are all the way up the top here. And I've heard of people actually traveling from Alaska all the way to Argentina. And it was a crazy idea. I mean, it was nuts. And we're like, come on, no way, you know? But it started to grow on us and we thought, you know, we can do it slow and just kind of move along.

And so we ended up buying a big truck. We changed out our vehicle and it just worked out just right to get a vehicle that would work for the overlanding. And so we pulled out of Alaska four years ago and just slowly started making our way South, you know, exploring and experiencing, visiting with people, building incredible friendships, meeting wonderful people, and seeing things we never knew existed and just slowly meandered through, like I mentioned previously, through Canada and the Western United States.

Four months just meandering through Mexico and a month in Belize. Ended up staying a year and a half in Guatemala 'cause we set up a humanitarian organization to try to help them. They're pretty impoverished and undernourished there. And so that's still going. And so we stayed there for a while and then a couple months on the beach in Nicaragua.

And then we've been here in Costa Rica for a year. And that's where number six was born down here. - And from here, are you gonna ship over, ship around the Darien Gap and start in South America? Or what's next? - So that was the plan. And we still wanna do that.

So yeah, you drive into Panama, you go to Cologne, which is on the Caribbean side, just another side of Panama City. And you ship from Cologne into Cartagena, Colombia to get across the Darien Gap. And we will do that and then explore the rest of South America. We wanna see every country down there.

But we really, I don't know, it just kinda, without planning, it just kinda popped up, this desire and kind of impression to go over to Europe and Africa. And so we actually, this year, our plan is to head to, we're gonna fly into Barcelona and spend a few months in Spain, Portugal, and France, and then do a few months in Morocco and spend some time in Africa.

And then go over and maybe see a little bit of Israel, Egypt, Eastern Europe. And just kinda do that. We don't feel like that'll be long-term, but we just kinda go over there, we wanna experience that and get some different languages, different cultures. I've already started learning French now.

I'm practicing that to get over there. So just some different cultures, different customs, different languages, and then come back over and then finish the rest of this trip in South America. - So it sounds pretty cool, for those of us who are an adventurous sort. But how practically do you actually pay for your life on the road?

Are you earning income? Is it all, do you have real estate in the US still? Or how practically do you pay for your life on the road? - Right. And I know this sounds crazy. Some people were like, that is nuts. And it is, I acknowledge that. It is a crazy lifestyle.

But we'll rent a place. So we come down, we rent a place, a beautiful place on the beach or in the mountains. We enjoy the people and the culture and try to do some service and make things happen. And it actually is, it's slow, it's deliberate. We keep our family routines.

We do the same thing, the same things whether we're moving or staying in a place. And so we live a life that, it's a great life. It really is. So the way we pay for it is, we've done several different things, but now I'm an educational mentor. And so I mentor mostly youth and young adults in a classical based education.

And so I do, there's so many great softwares and so many great resources and technology that come along just even in the last five years that have made that possible. And so I meet with, on a daily basis, I meet with youth and young adults and some adults for educational mentoring.

And that's the bulk of what we do. We've also started a site called worldschoolacademy.com, which really is just, it's helping parents with other options. We're so passionate about education. And so helping whether people homeschool or unschool, or they wanna travel or live abroad or whatever they wanna do, public school, private school, just give educational resources for families.

So that's the bulk of what we're doing. My wife is also a web designer. So she does some web design when she wants to. And that's the bulk of what we're doing right now. And I can do that wherever there's a decent internet connection. - So this world, this tutoring, so essentially you're having Skype meetings, kind of coaching type of things.

Parents will hire you to coach their children and to mentor their children. Is that the type of thing you're talking about? - Yeah, exactly. I do teach a couple leadership courses on an academy, the Williamsburg Academy. I teach a couple leadership courses there and really, really great stuff, classical based liberal arts stuff, and just studying the great things and really preparing youth and young adults to lead out.

But yeah, the parents hire me to lead the educational and personal development pursuits for their young women and young men. - Did you have that established before leaving on your trip? Or was this something that you worked out while you were on the road? - No, I came along the road, yeah.

And we've done several different things along the road and explored many different ideas. And actually started a few different companies. And we just kind of fell into this. And this for us, one of the things I guess I gotta share is that we think it's so important to live purposely.

And I know people have strong feelings about that, but I feel like everyone has a purpose, a mission, maybe a gift, or like I like to call it, everyone has a song to sing, something they can offer. And so it's not merely about making money. It's not merely about having an income source.

I think it's possible to earn an income, a good income, doing something you love to do. And man, I'm in my spot. I'm singing my song and I love it. And so it's a great way to earn a good income and to do something you really love and are passionate about.

- On the road, I know you've been on the road for quite a while. You must have come across lots of people that are on the road and earning income and basically just weren't willing to wait until they were old and rich to head out. And I think if memory is correct, didn't you and your wife, I think you created a series of videos at some point profiling different people and their stories.

Could you share some of the ideas and some of the different paths that you've come across of other families, how they've taken their families on the road and paid for it while they traveled? - Yeah, so I mean, we found an astoundingly a lot of people out doing this and living unconventionally, either living abroad or traveling full-time or even kind of nomadic, either as single people or couples or families.

And we were shocked to find that many. So many of them who didn't have blogs were just out wandering the earth. And everywhere we went, we started meeting more and more people. And as we pulled out of Alaska with our website, people started to contact us all along the way and said, "Hey, we'll meet up here." And, "Hey, come stay with us here." And, "Oh, when you get there, we'll meet up there." And we've built some absolutely incredible friendships but also started meeting all these people.

And of course I'm a very curious person. I wanted to learn. So I started just asking all these great questions and getting these excellent stories. I thought, you know, I gotta get this on video. I gotta record these things and share it with people. And so we did. We started a series there, just interviewing all the travelers we met and the curiosity of, well, how are you funding this lifestyle?

How are you making it happen? And how are you building your life? And it was so fun and so insightful to see, a single guy who can live in Central America or Asia on as little as 500 bucks a month and live pretty well. I mean, you could do it.

If you're a minimalist, you can live pretty well at a few hundred bucks up to, you know, I interviewed families that are making $75,000 a month. No, $30,000 a month and several, 20, $25,000 a month. And they're mobile. They're completely mobile. They can do their work from wherever they want.

And so they choose where they wanna live just because they feel like living there for a while. And if they wanna move, they'll move. And so it was fascinating to see how they built their businesses, how they run their businesses, how they grow their businesses and how they build it around their lifestyle.

And I guess that was a common thing that most of them chose a lifestyle and then built a business around that instead of choosing a career or having a career choose them and then building their life around that career. So it was a really unconventional idea and pretty fascinating and powerful and fun to explore and understand that.

- So obviously all of the work was being done through an internet connection, but what were the types of actual careers? Was it all selling get-rich-quick schemes on the internet or were just some of them people had taken more traditional roles online? What were the types of jobs that people were doing?

- Yeah, that's a great question. And a lot of people kind of jump on that and immediately assume, oh, it's probably some blogger blogging about their travels and trying to sell something. And what I found for the most part, actually, it was quite different. Almost none of the people we interviewed did it that way.

They actually were doing things that were pretty normal and pretty simple. And some of them actually were in location. So there was a few of them that don't require internet, but nowadays, most of it's required internet. Let me think through a few of them. One of them, they were wholesale.

They had set up wholesale accounts selling watches and jewelry. Another one sold electronic cigarettes. Another one, several of them actually have been virtual assistants where they do either marketing or web design or assistant type work for businesses and entrepreneurs. Some of the others, one of them ran a running company, had a running company.

Some did some teaching. Some did multi-level marketing things or sold other products. Several of them did information products. They would create eBooks. Some of them were in travel, how to travel, how to travel with family, how to travel around the road, how to travel cheaply. Man, I'm trying to think through them.

There were so many different options and so many different ideas. Well, several of them were investors. I interviewed several investors. One did Forex trading. One did just straight stocks. One traded options. Others did real estate investing or sold real estate in that country wherever they chose to go live.

I mean, there's just so many different options. That's what astounded me is you kind of roll out thinking there's probably only a couple ways to really make money online. And the truth is there are more and more ways every day. And in fact, the variety of ways to do it was as unique as the people who were doing it.

- Right, that's exactly kind of where I was hoping you would go because the trend I see is in the early, so-called, we're still in the early days, but a decade or so ago, if you were gonna make money online, it was probably gonna be something relating to teaching people how to make money online or selling an info product or something like that.

And nothing wrong with that. That can be hugely valuable. But I see a couple of trends. Number one, if you have a physical job, many physical jobs are very much in danger of being outsourced. And so you need to be careful of the type of physical work you have.

If you're working in a factory or if you're working in a warehouse or something like that, it's only a matter of time until many of those jobs get outsourced. If you're driving a truck or driving a car for a living, it's only a matter of time, I don't know, a decade or two before all of those things will be self-driving.

But many jobs that have been traditionally done in offices have easily made a transition to being done just simply through the internet connection. So whether it's the type of work that I do with this podcast, with this show, whether it's the type of work I do as a financial advisor, whether it's, you know, there's just so many things where it's getting easier and easier.

And so I think more and more jobs or businesses that people are already engaged in can simply be moved virtually. And you might have to shuffle some clients around. You might have to fire a few and get a few new ones that are willing to work with you in that way.

But there are so many options open to people at this point that never existed before, where simply location is not that big a deal. And so you can, the world is truly open to you. - Oh, absolutely. I'm so glad you brought that up because it's critical that people understand that.

And in fact, you kind of sparked the memory of several people we interviewed who actually, you know, they asked their employer, "Hey, could I work remotely?" And in many cases, reporters are like, "Well, let's give it a try." And it worked. And then there's big, big organizations that have huge calling centers.

They're just saying, "You know what? "Let's figure out how we can get people "to answer the phones at home." And so they're getting rid of these huge office building and they're getting rid of all the overhead and the commute time and all these other obstacles. And they're moving things to, yeah, to the digital life.

So you can do it from home or you can do it wherever you are in the world. And it's changing. You know, and I love to think about that whole idea. You know, five years from now, there's gonna be something that we depend on that doesn't even exist today.

And we're gonna be, you know, using things that don't exist that we're gonna say, "We gotta have that." I mean, new technologies are gonna come out and they're gonna offer so many more jobs and so many more opportunities, but people have got to be willing to change and explore new ideas and stay current with things and with their own growth and their own skills and abilities and their knowledge.

I mean, think about how movie rental stores seemed like such a solid investment. Like, you know, people will always watch a movie. Let's open a movie rental store. They're gone. They're gone. It went from video cassettes to DVDs to now you just, you click a button on your computer and you can rent a movie.

And it's just fascinating. So you gotta be able to change and adapt to these exciting times we live in. - You tried a few different things, and you've tried many things, and I'm sure you'll try more before you've found what's currently effective for you, which is this online tutoring and mentoring, right?

- Right. So I just wanted to make that point because that's also something I've seen and heard, or I just have observed. There's a very uncomfortable, the transition that's happening in our society is very uncomfortable. So some businesses, I think it was a year ago that Yahoo was famous for kind of revoking a lot of their work from home stuff and saying we've got to come back in the office.

And so some things are working, some things aren't working. Some jobs and businesses, people are finding, no, I really do need this in-person interaction. And some people are finding, no, I really don't. So I would just say if you're gonna pursue this type of alternative lifestyle, be flexible and be willing to work at things and adapt and change and don't feel like if you do something and it doesn't work, that's the end of your life.

You can find a way to make, you can find a way to press through and assure the dream if you're willing to keep working at it. - Oh, absolutely. And it's almost essential, I would say. In fact, I'd be bold enough to say that you kind of have to fail a couple times.

You have to fail forward, you have to try stuff. Like I mentioned, I'm a voracious reader. I read biographies, autobiographies, and studies. And so many of the very successful people we look at and admire had failures, even bankruptcies. I know several multimillionaires who said, yeah, two or three bankruptcies, kind of the norm before you really get going and get humming.

And they fail forward, they try things that don't work out. And a lot of people we interviewed said, yeah, we tried this, we tried that, it didn't work, but we learned so many great lessons. And because of those lessons, we were able to start it up again and really make it happen.

So there's almost this failing forward process that I think you try things and don't throw in the towel, don't give up. And like you were saying, be very flexible and be able to move with what's happening in the current demographics and in society. - Greg, what makes people willing to fail?

- A vision. And I think where people lack a vision, they're afraid of failure and be willing to quit. Either one, not to try at all, or two, to give up, but you've got to have a clear vision of where you're going and what you want. 'Cause failing's not easy, and man, is it uncomfortable.

And it's brutal, but you have to be willing to fail, learn from your failures and get up, dust yourself off and do it again. And I think one of the main things, you've got to have a vision of where you're going or else you just can't stick through it.

- Reason I say it's interesting because to me, in my work, both in my own personal life and then in my work with financial planning clients, I think this is one of the areas where we could use some enhancements on I guess the literature that's available. 'Cause what I was always frustrated, I read a lot as well, and one of the things that always frustrated me was reading about people talking about, oh, failure is gonna be valuable for you.

And to be fair, very few authors say that failure is fun. It's certainly not fun. Most people acknowledge that it's not fun. But many times, people, authors or things that you read, they kind of just gloss over, I guess the reasons why you would be willing to accept failure.

And I know for me, I've watched so many people where I look at their situation, I say, look, it's simple, just do this, this, this, this. And no, I can't guarantee it's gonna work, but it's probably gonna work. But then I look at my own personal journey and I closed my financial planning practice to start Radical Personal Finance.

And there was zero chance of, excuse me, there's zero assurance of success. In fact, it's probably the most difficult, risky business venture that I could imagine doing. But I just came to the point where I didn't, I was more, I'm more, I still am. I'm more willing to just simply accept failure.

I'm more willing to sell my house. I'm more willing to go into debt. I'm more willing to, shoot, if I wind up bankrupt, whatever, I'll deal with it. And I just got to the point where I just didn't really care, meaning I do care. I'm not, my word is good.

It's very important to me to do things well. But I got to the point where I feared not trying and regretting something more than I feared trying something and failing at it. And it's hard to articulate that because it's a very transformative experience. But it's something I think a lot about and try to help, how to help people, not pursue something that's not gonna work, but be willing to have something that you want, that you're willing to pursue enough so that even if it doesn't work, you're still satisfied with your choice to pursue it.

- Yes, amen, amen. To be able to kind of put it on the line in order to live a better story, to take the risk to, well, like I mentioned, it being to live deliberately, to step out there and make it happen. Yeah, oh, it's what I call the exchange rate.

What are you willing to exchange your life and time for? And are you willing to take those risks in order to build something great, in order to build a life that you absolutely love? And part of that is that, well, I guess my favorite saying is that failure is fertilizer.

(laughing) And it stinks, but man, it's good. It gets the work done. And I love your story. That's a great story where you just, you gotta put it on the line and face the consequences or the potential consequences and say, I'll deal with that if it comes, but I'm willing to put it on the line here and to get, like Theodore Roosevelt says, to get in the arena and get dirty and maybe a little bloody, but to get in there and not be with those timid souls who know neither victory nor defeat.

- Love that quote. And again, it's not that good planning isn't important. You know, I certainly, I don't, I have zero intention of winding up bankrupt. I acknowledge that it's a theoretical possibility, but good planning can avoid that for the most part. And so I have zero intention of ever winding up in that place.

I guess the point is you get to a scenario, you get to a place in life where you just realize, no matter what, this is something that needs to be pursued. And I think there's a real joy in the work. There's a real joy in the struggle that we don't often discuss in our society.

It seems as though in our modern era, we look to pleasure as a source of happiness. And we assume that if life is easy and if life is pleasurable, then that's gonna be what's truly joyful. But the reality is there's a great joy in victory. And my proof for that is look at all the people that wake up at five in the morning and go out and run every day.

Look at all the people who sign up for an extreme sport or who sign up for a triathlon. Look at all the people who are looking desperately for this sense of accomplishment that comes through doing something that's difficult. And I would never tell someone where they should or shouldn't find it, but you can find it in running a triathlon, and you can also find it in building a business.

You can find it in traveling in a different country where it's a little bit more difficult to travel comfortably. And there's a real joy that I find, at least, being out there and working hard at something that's difficult because you get that sense of accomplishment, which it's easy not to get in modern Western society.

- Oh, man, I love that. It really resonates with me. And not even, the accomplishment's amazing, but some of us thrive on the challenge and the difficulty and the struggle. And I think that's what you mean by the accomplishment. Like you did something really hard. And I did triathlons for years, and so I'm sitting here, you're naming these things, and I'm like, oh, yeah, those were brutal.

And I get up every day at 4 a.m. So I can study and exercise, and I love pushing myself. And you're right. So I gotta share this 'cause it just changed, it changed my whole reality. It's a phrase called bread and circuses in Latin. I'm gonna kill the Latin, but it's panum et circensis is what it is, the bread and circuses.

And what it did, it brought about the fall of Rome. And it was the idea that came in, these politicians came in, and they wanted to win the votes. And the idea was, look, if I give, if we get the people to have food and entertainment, so bread and circuses, right, if we give 'em food, cheap food and cheap entertainment, right, then they'll have the, we give 'em, I'm quoting here, "The satisfaction "of the immediate shallow requirements of the populace." And so you just kinda get 'em to settle in and be content.

It's a means of appeasement, public approval. And it just kinda sets it open. So a lot of us, we settle in and we're like, well, no, let's find something that's easy and comfortable. Right, we love ease and comfort, we love entertainment. And I think sometimes we can really miss out on the great parts of life if what we often seek is food, cheap food and cheap entertainment.

And that brought down, Juvenile said this brought down the fall of Rome. It was that movement toward just, if we got food and we have entertainment, we're good to go. But I think you're absolutely right, that we can push ourselves and be wise and plan and prepare, you don't have to be crazy.

But to be willing at some point, you say, okay, it's never gonna be a perfect time. You gotta just take a step into the darkness and go for it. - How do you keep your energy high? And what I mean is that you are an extremely energetic and effusive person.

And if I weren't familiar with your work, I would think in many ways that it was a front. But having seen your work over the years, I'm convinced that it's actually probably how you express yourself on a daily basis. How do you keep your energy so high? - That's funny, Josh, you bring that up.

It's true, a lot of people are like, man, are you being fake? Are you putting, is this your microphone voice, your camera face or whatever? But this is how I live. I just, I'm a really excited and excitable guy and I live with high energy. Some of my friends call me the, it's like I'm a walking anti-depressant.

(laughing) I just love life. And like I mentioned at the beginning, I came from a dark place, man. And those were some hard years where I had no friends around, no family, just some real struggles in some tough areas. And I thought, life doesn't have to be like this.

Life can be great. And I live with a deep sense of gratitude. For me, my alarm clock is an opportunity clock, sincerely. I mean, I'm grateful to be alive and to count those blessings, to have my health and a family and be able to live and do things that I love to do and make a difference in the world, to live on purpose.

So how do I maintain the energy? I view myself as a holistic person, as a whole person. And it's spiritually, emotionally, mentally, physically, and socially. It's balancing those things, giving each of them not equal attention, but appropriate attention, as much as each of them needs to be healthy and well.

But too many of us get, we get burned out one way or the other. Maybe we don't have the physical health or the emotional strength or relationships are hurting or we neglected the spiritual side of ourselves. And so if we keep all those in an appropriate balance and we spend time each day working on our highest priorities, I eat very, very well.

I exercise vigorously every day. I spend time in meditation and prayer, work on emotional mastery and greatness and relationships. Man, it just makes for an absolutely fantastic life. And it's not a front. And I'm glad you have that experience with me to go know if to have time that this is consistently who I am and who I try to be.

And I really am excited and happy. And I sincerely love life. It's not a show. I just, I'm like this. My kids will tell you that. My wife will tell you that. My friends will tell you that. But it's, for me, it's a great way to live. I really live with enthusiasm.

And I just wanna be happy all the time and really, really not miss out on a fun day of life. - What were the catalysts in your early life? You said twice now that you said you came from a really a tough starting place. What were the catalysts in your early life that kind of made a real difference in the direction of your life?

Were there people? Was there influences? Was there books? What made a real difference in your life in those early years? - Oh man, that's such a great question. There was, I was reading great books. I realized that life didn't have to be that way. At some point, I don't even know if I would have cognitively have stated it this way, but at some point I kind of came to the realization that life is exactly what you make of it.

And if other people were living happy, successful lives, then I could too. And I came to the realization that nothing will get better until I do. And that's just a great truth there, that nothing gets better until you do. And then everything gets better as you do. And that I wasn't a victim.

And so along the way, there were, yes, of course, there were great people who reached out and helped and mentored, led me. And then great books that started to shift my reality. And I just came to this clear idea that I was accountable. Yes, people had done things to me.

Yes, my parents had made mistakes. And yes, I'd been wronged. And that was my past. But living in the past wasn't gonna help me. And I came to this day where I just realized, you know what, I am accountable from this point on, I am accountable for how my life turns out and I better make it awesome.

Why not? You know, if I get to choose, then choose awesome. And so I just said, I'm gonna go after it vigorously. That was 20 years ago. And I have been studying voraciously in personal development and history and great classics and the best books and the great questions and really pushing after personal development and trying to make the most of myself.

And I believe, I guess I would say that the greatest tragedy in the world is when a person, you or I, does not reach their full potential. And so I go after it vigorously, trying to be my very best self. And when we take full responsibility for our lives and we make a clear plan to build life as we wanna live it, then there's a path and there's a way.

And it's awesome. It's not all roses and not all fun. There's always challenges and obstacles. But man, life is great. - When you and your wife originally had the idea to start traveling, was one of you really the champion of that idea and had to get the other person on board or did you come to it together?

- Fortunately, because we both read so much, it was easy. It wasn't one of us convincing the other. We both had come across all these different books. We'd say, hey, this great book, why don't you read it? And we'd read it and go, oh, hey, that's a great idea.

And we kinda discussed these ideas. And so luckily, really from the time we were married, we've grown together in our vision. And fortunately, we both felt strongly about this and we've read the same books and had the same discussions and really same experiences and come to similar conclusions at least.

We don't agree on everything, but we really came to these conclusions like, yeah, there's a different way to live. There's an unconventional way to live. And at least for our family, we wanna grow up with a global perspective and get out and see this beautiful world and make a difference while we're doing it.

So it's just been a really great blessing that most of those things we've seen eye to eye have been able to move together. And man, it's so much better when you can move together like that. - Absolutely. A couple of final questions here. And I wanna probe just a little bit with regard to, let's start with just some of the, let's start with this.

What is the biggest challenge or a few of the biggest challenges? And I understand that it's great and it's exciting and it's really wonderful, but every lifestyle that we choose certainly has things that are difficult. What are the biggest difficulties and challenges of the lifestyle that you've chosen? - So I guess I would have to say conveniences is what it is.

Especially if people are interested in traveling or living abroad long-term or kind of traveling long-term. And I guess that's kind of our lifestyle. In each place, it's very different. And if you go in with certain expectations or you want every place to be, say, for example, you want every place to be like the United States.

Well, you know, you say, hey, well, back in the States, we do it like this, we do it like that. But you can drive yourself crazy going, ah, always comparing to how it is somewhere else. And I think there's just inconveniences. And my wife and I were talking about that last night.

So, you know, it's just, it's absolutely worth it for us. And for some people it's not worth it, but for us it's worth some of the inconveniences with different visas or the inability to get different products. You know, in some of the countries, it's really hard to find the things you're after.

Whether it be books or certain appliances or getting your computer repaired or something. There's some of those things that just come with travel that are some of the inconveniences, but too big of an exchange rate to be inconvenienced. But I would say for us personally, I would say that's it.

We clearly, the school or what we call world school, our children, and so the schools hasn't been a big issue, but it is for some. But yeah, you know, and you're away from family and there's a lot of, you get a lot of criticism for living unconventionally. And that you have to be able to handle some of that too as it comes in.

- Are you concerned about your children and your family not feeling a sense of community as they get older? - Oh, really great question. And we are very passionate about that and very intentional about that. We want to raise leaders who have great social skills and a great education and are willing to and able to communicate effectively and relate to both young and old and rich and poor and black and white and everything in between and every race and religion and to really connect.

And it's been fun as a family to connect in the communities where we've had. So we don't have an in-person really long-term connection, like we don't spend 10 years in one place, but we've connected deeply with a lot of people in a lot of places. And literally it's been fun.

We have friends all over this world and our children have friends all over the world. And it's just a great experience. And now technology is so good that we can do video, video conferencing constantly with family and friends all over the place. And so, no, I'm not concerned about that lack of community because wherever we are, we dig in and we connect.

And when we stay connected to our close friends and where travel has become inexpensive and easy, we're constantly all over the place and connecting. So, no, I'm not concerned about that with them. - If you were gonna pick a day and not the ideal day that if you were gonna write a blog post about the ideal day to tell people why travel is so great, but an actual day, I'm interested to know what, for you as a father with six active children and your wife and you both have a lot of responsibility and you're trying to earn an income and manage your children and learn where to go to get the type of shampoo that doesn't make your hair flake and all of that kind of stuff.

What does an actual day look like for you as far as how you run your schedule at this point with your family and your online work and all of your responsibilities? - Yeah, awesome, awesome question. And you have to be pretty intense about it. If you wanna stay prioritized, you have to stick to your things because there's so many distractions.

And that's true whether you move or you stay in one place. There's always the laundry, the dishes, the people calling here, the little urgencies, the fires to put out. You have to be intense about reaching your biggest priorities each day. So, like I mentioned, I wake up really early, usually around four, and I spend time doing meditation and planning goals.

I read scripture and I read great books. I do all my studying and just kind of my personal priorities and I get some exercise in. That's what we do first thing in the morning. And then we have a morning devotional that we do. And we always stick to it where we sit down as a family.

We have all our meals together as a family. But in the morning, we do our studying, we do our memorizing as a family, we memorize great things. And then they jump right into the education. And that's where I'll go do my mentoring and my work, and my wife will spend time then the first few hours of the day helping each kid get their education and work on each of their subjects and kind of dig into that.

And then we always try to, and they'll do that for several hours. And then they get their playtime, their adventure time, they get out and run around in the rainforest here and play and have a good time. And we always like to do, we always like to do some kind of adventure, either to go for a run or a hike or run down to the beach.

I like to go down early in the morning. Sometimes I'll go down and surf with my sons just a couple of weeks ago, we were surfing and these baby sea turtles swam past us. We grabbed one and played with her for a minute. It was just, it was epic, man.

It was awesome. Watch the sunrise, play with a little sea turtle on the surfboard there with my son who's 10. And have those bonding experiences, it was a great experience together. We'll go jump in a waterfall down here or just go do something fun or we'll go surf. And this isn't every day, but we try to throw this in where we go out and serve someone who's in need, go visit someone.

And then every night before bed, I read to the kids. And so that's kind of these rituals we stick to and then they change. You gotta run to town for the, get the groceries in the open markets here. You gotta go down and visit with some friends or something.

But for the most part, that's usually how the day goes. - Do you restrict your work to those hours in the morning in which your kids are studying? - Yes. For the most part, my schedule is usually from like eight to two, eight to three. Now I do a ton of reading.

And so I'll, in the morning or in the afternoons, late afternoons, I'll sit down and do some reading or some studying or prep work, which is part of my work. But I count on being interrupted. Little baby needs to be held or a little boy wants to show me something he's working on or my daughter wants to do something, go share me, show me something or have a little venture.

And so I plan on being interrupted, but I spend some time and I'm with them. And I guess that's cool. That's kind of lifestyle we've kind of designed that I'm here and I can be sitting there doing some reading or some studying or prep work, but I'm right here and I can be interrupted.

- Why, is it a big deal to you that you and your wife are involved with your kids' educations? Is it just circumstantial because that's the way you have to do it if you want to travel? Or was that important to you even if you weren't traveling? - Yeah, absolutely.

Right after we got married, we decided that's the way it'd be. That's not something we wanted to outsource completely. Now, obviously there's tons of resources and we like hiring tutors to come in and help with specialties that we may not cover as well. Or often, sometimes your child respond better to a third party than to you.

But we want to be hands-on with our kids' education because it's so important to us that they get literally a world-class education and a leadership education. And so we are hands-on to that and always involved and always will be. That's important to us and has been from the beginning.

So if we were back in the States just living out the life that we were doing before, we'd still do the same thing. - Practically, there in Costa Rica, how practically are your kids studying right now? Do you have a bunch of books and they're working their way through books?

Are they all sharing one computer? Do you have six iPads floating around the living room? How do you practically do it? (laughing) - Yeah, it's awesome. And it's funny. We pack hundreds of books all over the world. I feel like a pack mule sometimes moving the books. But we feel it's important to have books in hand.

And yes, we have lots of digital books and lots of audio books. We use all three media there, but we definitely are using paper books, have lots of them, we pack them all over. So, and ours is a classical-based curriculum, I guess you could call it. So a lot of great books, the best books that have been written throughout time.

We also do have the iPad, the iPhone, couple computers, a couple Kindle Fires. And so the kids will do like Khan Academy, excellent resource. They do Duolingo, which is also a phenomenal resource for languages. They'll get on, they'll do math games. And we do a lot of researching for the sciences, the arts.

I kind of think like there isn't anything you can't do with YouTube. You can learn almost anything. It's really great. And then, we can do some tutoring and meet up with other people. You can do a Skype session or something with someone who's got a gift. You can even take music lessons online or other resources.

So it really is, it's such an exciting time to be alive because with some books in hand and access to the internet and a computer and iPad, you can really get access to just about anything you need to for a great education. - So my final question is this.

I'm a big fan of travel and at this stage in my life and with my family, we've decided it's not something that we're pursuing at this stage, but it may in the future. We'll see how time works out. But one of the things I think is most valuable about travel that many people don't talk about is everyone focuses on perhaps, many people focus on the romance of travel, the idea of doing something different.

But I think there are some lessons from travel that could be applied when you're living in one space. So I'm curious to know, if I put a situation in your life, let's say that you had ailing parents, either you or your wife or a relative that you needed to be close to and you were gonna be in and I were gonna bring you back to the United States and put you in a place that you were familiar with and you were gonna be there for a few years.

I'm interested to know, after all your years on the road, how would you structure your days? How would you structure your life? And what lessons would you apply to that more common, so to speak, type of life, more conventional looking life? What lessons would you apply to that type of lifestyle that you've learned from your time on the road?

- Woo, man, that's a really great question. That's well thought out. I like that a lot. My initial reaction to that would be like, no! I can't do it. Except for what's called adult ADD, adventure deficit disorder. (laughing) - Like it. - I gotta get out and play. So no, but I've thought about that often and I have a lot of friends and people who contact us constantly on our websites and say, you know what, we're not gonna get out.

How do we, yeah, basically what your question is, what do you apply all these things you've learned, how do you make it happen? And here's what I would do as I've thought through that often. I've literally thought about that question often. I think we all need novelty, new experiences.

And actually, you can study this physiologically. There's neural connections that happen with novelty and there's actually dopamine and serotonin and endorphins that get released into your body as you're having new experiences. And I think one of the things we miss out if we're staying in one place is we don't create enough new experiences.

We get comfortable with one thing and we kind of settle in, sometimes mentally, emotionally, socially, physically, we just kind of settle in and we stay. And that doesn't have to be the case even if you live in the same place. You can go to new restaurants, you can run at different places, you can go out and meet new people, you can have new experiences.

And I would just say you'd have to be, and I especially would have to be very deliberate about having adventures and challenges. I would be signed up for all kinds of different races. I'd sign up for a decathlon or something, just something to challenge me in all kinds of levels.

I would get involved in community projects or organizations or groups that were challenging me mentally and socially. And I would be planning, I'd be very, very strategic. I'd plan out a year and do one small adventure a week, one pretty great adventure a month, and one epic adventure every quarter to make sure that I personally am feeling alive and getting out and connecting.

And I would be intense about learning another language and practicing it with anyone I can find, taking new classes, and especially in the States because we miss that down here. I'd be spending a lot of time at the library. - Right, right. Yeah, I think it's, and that's why I wanted to wrap up on one of those places because oftentimes, that's why I wanted to wrap up with that question.

Oftentimes we romanticize another person's life. We romanticize another person's experiences. And I think each of us hopefully should just be focused on living the life that is right for us. But I'll tell you, one of the, for me, I've been blessed at a young age, and I'm almost 30, and I've been blessed to be able to visit a lot of places and do a good amount of travel.

And I'd like to do it, I'd like to do more in the future, but for me, some of the most transformative experiences of my life have occurred because of the travel. And it wasn't necessarily the travel of itself, but rather it was the change of mindset. So whether it's my ability to feel content with my standard of living, I'll tell you, for our honeymoon, my wife and I, we went to the Dominican Republic and then to Haiti.

And every time we travel in a place like that, we spent several days in Haiti, and you spend time in a place like that, you come back home and we started off our life in a little 200, I think it was 234 square foot studio apartment after we were married.

But we had just come back from Haiti and that apartment was beautiful. And I had friends that would say to me, like, "How on earth can you live in this place?" And I'd just say, "Listen, what on earth more do I need? I have a bed, I have a chair, I have a table, we have a kitchen and have a bathroom and a closet, a place for our clothes.

We're two people, why do we need anything more? Why should I spend to fulfill this external expectation of the US American culture? After all, I'm thankful. You don't know where I just was. I'm thankful to be in this situation. I'm thankful to have such a beautiful place to live where it's clean and it's bright and it's pretty and it's beautiful and it's safe and it's easy.

I turn on the tap and there's hot water and I plug something into the wall and there's electricity. And so that would be an example for me. Or another one is that I have to continually remind myself of, I'm very, me personally, I'm very much a people pleaser and it's difficult for me to go against the grain.

So I'm heavily influenced by peer pressure. And so it's easy for me to feel like I've got to keep up with everyone else. I've got to have the fanciest toy. I've got to drive the fanciest car. I need to look like everyone else. But when I travel sometimes and all that's stripped away and I don't ever have to compare myself to the other people, then I learn to be a little bit more confident in me.

And so as an example, one of my visions for my life is I don't want to be disconnected from my family. I don't want to live this common existence where I wake up early in the morning and I scarf down a bite to eat and then I'm away from my family for the next 10 hours and I come home exhausted at 6.30 at night or 7 o'clock at night, maybe my kids are already in bed and I scarf down some food and flip on the TV.

To me, that's not living. So I've worked hard and I'm working hard on creating. I'm able, in the US-American context, I have three meals a day with my family. I wake up and I work from home and I do work that I care about. And then I still need to work on-- and we try.

This afternoon, as soon as we finish up interviewing, it's a beautiful day here in South Florida. And I've got some more work that I probably should do. But you know what? It can wait. And I'm going to take my family on a little adventure and figure that out. So these lessons from travel can be applied in any context.

And you don't have to just be on the road. You don't just have to live in an RV to live simply. You don't just have to go to Costa Rica to learn Spanish and engage with new cultures and new cuisine. You don't have to go and eat street food in Nicaragua to eat street food.

There's street food everywhere. You can make a choice other than TGI Fridays. And that's a lesson that I think we don't talk enough about. Man, I so agree. That is such a beautiful paradigm you have across the board there. And I think that's the perspective you gain from getting out and having new experiences outside of our common experiences.

It makes you just come back with a different perspective. I love that. Oh, I love that. I guess that's one thing I might add to that. I think I would come back and try living in one of those tiny houses that are becoming popular, just to say, hey, we did it.

I don't know. I think your wife is an adventurous sort. But unless that tiny house is parked on the beach with six kids and the two of you, I think you need something a little bigger, at least a fifth wheel. Everybody is going crazy. I floated that idea with my wife.

She didn't fly for it. So I'm thankful. And I'm thankful for it. If I were a single person, maybe. But like I said, we've got two kids. And we're hoping for more in the future. That's awesome. So you need a little bit of space. So Greg, we're-- let's see, discovershareinspire.com.

And then was it gregdenning.com? What are your websites? Yep, discovershareinspire.com, gregdenning.com, and then worldschoolacademy.com. Man, I appreciate it so much. You're coming on the show today. This was super fun. And I would encourage people to check out some of your adventures and others of your riding. And I'll make sure to link to all that stuff in the notes.

Awesome. Thanks, Joshua. This was really enjoyable. Now, what do you need to apply from this to your life? Take it and apply it. I think probably the biggest gem might be even there at the end. Just because you're not traveling doesn't mean you can't live the life of adventure.

Plan it out. Think it through. Make a plan for how you can accomplish your personal adventure goals. It really is pretty inconvenient in many ways live on the road. A lot of benefits from it. But it's also pretty inconvenient. And if you can take the desire for adventure and apply it to your situation, it might bring a little bit more zest to your daily life.

Just a thought. Walk around your town. Schedule a tour with a tour guide of your town. Walk around your town with your phone and do a photojournalist shot. Take pictures of interesting things. I'm always a little bit envious of photographers because they seem to just notice so many interesting things because they're always looking through the lens of a camera.

Interesting buildings and interesting just stuff everywhere. So how can you apply that to your life? I'm working on applying it to mine. Thrilled to be here sharing the journey with you. Thank you so much for each of you who are supporting the show. Again, as mentioned in the beginning, if you'd like to make sure we keep the show here free of corporate interest, please go to radicalpersonalfinance.com/patron.

I would be thrilled if you would do that. It would help so much. By June 1, the goal is by June 1, we need to get the show to $6,000 a month, and I can avoid taking advertising. That would be in excess. If I-- under the rates today of the listenership of the show, that's basically the number that I could get from advertisers with the number of shows that I do and the frequency.

It would be about that $5,000 to $6,000 a month number. So that's why it's one of the goals. If we can get to that with listener support, I would really love to do that. So I just ask you for your help. radicalpersonalfinance.com/patron. Tomorrow, I'll be back with a special show.

If you are a patron of the show, check out the Patreon page, the activity feed, for the details of that, and you can have input into it. That's it. See you all tomorrow. , Thank you for listening to-- Thank you for listening to today's show. If you'd like to contact me personally, my email address is joshua@radicalpersonalfinance.com.

You can also connect with the show on Twitter, @radicalpf, and at facebook.com/radicalpersonalfinance. This show is intended to provide entertainment, education, and financial enlightenment. But your situation is unique, and I cannot deliver any actionable advice without knowing anything about you. Please, develop a team of professional advisors who you find to be caring, competent, and trustworthy, and consult them, because they are the ones who can understand your specific needs, your specific goals, and provide specific answers to your questions.

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