Finding Freedom in an Unfree World with Kevin Koskella – EP 95

Interview with Kevin Koskella

Finding Freedom in an Unfree World with Kevin Koskella

We’re constantly bombarded with advice on how to live life and do business. If we follow that advice blindly, we risk drowning our authentic inner voice that can steer us toward our dream lifestyle.

Today’s guest, Kevin Koskella, wasn’t afraid to pursue his dream life even when his circumstances suggested otherwise. Kevin lost his job during the dot-com crash. Unsure what to do next, he decided that he wanted to be free of the corporate world.

Common sense and people around him suggested he find another job. Yet, he decided to be a part-time swim instructor and personal trainer. Later, he turned Tri Swim Coach, a business that teaches swimmers to become triathletes, into a full-time online location-independent business.

Kevin built his life around the values of independence and autonomy. Nothing he does goes against those values. He chose freedom, and that choice made him a happier and more confident person.

In this episode, we go over his journey from being laid off to starting a lucrative online business, his top investing strategies, the importance of designing and following your definition of success, and much more.

Featured on This Episode: Kevin Koskella

✅ What he does: Kevin Koskella is a world-renowned triathlon swim coach with over 27 years of swimming experience, an online entrepreneur, and a digital nomad. He’s been obsessed with freedom from a young age and has built his life around this concept with digital businesses, investments, and location independence. In 2017, Kevin founded Work Hero, a service that relieves online entrepreneurs of their technical and annoying tasks so they have the freedom to focus on the work they do best.

He also hosts the Freedom Lovin’ Podcast and is the author of The Rebel’s Guide to Freedom.

💬 Words of wisdom: “We need to heal those traumas that maybe are holding us back, the beliefs that are holding us back.” – Kevin Koskella

 🔎 Where to find Kevin Koskella: Twitter | LinkedIn | Instagram

Key Takeaways with Kevin Koskella

  • How Kevin developed a passion for travel and how that inspired him to seek freedom and independence.
  • Find something you’re passionate about and help people with it. Learn how Kevin went from being laid off to building a lucrative online business.
  • You can turn every obstacle in life into an opportunity. What Kevin learned from the real estate market crash and how it led to him finding crypto.
  • Kevin’s approach and mindset on investing in risky ventures.
  • We don’t have to sacrifice our freedoms to make the world a better place. The change starts with you and your idea of freedom.
  • Are you basing your definition of success on society’s or your parent’s expectations? Do the inner work, and define success on your terms.
  • Don’t be afraid to think outside of the box. It’s the only way to create a life that will be financially rewarding and fulfilling at the same time.

Kevin Koskella –  Why Dollar-Cost Averaging Is The Safest Crypto Strategy

Kevin Koskella Tweetables

“We can’t achieve freedom unless we dig inside and we really figure out ourselves.” - @freedomlovinway Click To Tweet “It’s really up to you, as an individual, to define success. You define it in your own terms.” - @freedomlovinway Click To Tweet


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Read the Full Transcript with Kevin Koskella

Justin Donald: What’s up, Kevin? It’s so good to have you on the show.


Kevin Koskella: Hey, Justin, thanks. It’s awesome to be here. And we are what, about a mile away?


Justin Donald: Yeah. It’s funny, we could definitely be doing this in person, but sometimes, and I think when we originally booked this, you were in Brazil. So, I wasn’t sure if you were going to be back or whatnot. But yeah, we totally could have done this in person.


Kevin Koskella: Yeah, you got to do that Lex Fridman thing, where you just have people coming to you and then it gives that personalization. I think it’s awesome.


Justin Donald: I love that. Yeah, there’s something to be said about that. And there are so many cool things that you can do with the in-person podcast. And so, I’ve debated a lot. Do I want to use the advantage of technology and Zoom where it really is effortless to do a podcast interview with someone anywhere in the world?


I mean, I’ve interviewed people for probably seven, well, let’s say six different continents and many countries. We’re probably at like 20 different countries where we’ve actually done recordings. But there’s just an ease with using an online platform, but there is definitely an intimacy and just something cool and unique about doing things in person.


Kevin Koskella: Yeah, for sure. But it is, I mean, just you’re saying that, and I’m thinking about how special a time we live in right now. It’s amazing that we can do this. I mean, it’s only a few years ago, this was not even happening. And here we are, you’re doing videos with people and audio and podcasts with people all over the world. And it’s just that was impossible.


I even remember doing one in 2009. I remember talking to this guy from New Zealand, and it was impossible. We could not communicate. It was like his bandwidth was too low, we couldn’t do it. And so, yeah.


Justin Donald: Yeah, it’s pretty cool. We live in such an interconnected world, and you got to love technology for all the things that it provides to bring people closer and make us more connected. Obviously, there are drawbacks with a lot of things. And I think there are pros and cons with virtually everything. But I’m excited to connect.


You’re a guy that lives a life after my own heart. You are a travel lover. Kevin, you’ve been to 46 countries around the world, and I just love the life that you lead. You have extended stay in all these different places and you’ve learned so much. And obviously, I love traveling as well. I’ve been to a ton of countries, and we just share this. So, I’d love to hear more about where your love and passion for travel came from and all the things you’ve kind of learned along the way.


Kevin Koskella: Yeah, that’s a great question. And as far as like going to countries, it’s funny because we put so much emphasis around these borders and it doesn’t really make any sense that we do this. And I don’t remember, I think I stopped counting at some point of the number of countries because you could go visit a country, you go to like the one city. And you saw almost none of the country. But you go, I’ve been to that country and it’s like you check it on, put on the list.


And so, I’m always hesitant to brag about how many countries I’ve been to. But it gives you people an idea, a general idea, of kind of how much you’ve traveled and where you’ve been. And so, yeah, I mean, when I was a kid, I had this globe in my bedroom. It was one of those big globes you can spin around. And I was like, I would just look at that thing like all the time. I’d be looking at all these places around the world and going, oh, it’ll be so amazing to go to Russia or be so amazing to go to Madagascar or something.


And I’m just like, I just thought every place in the world, it was just so fascinating because it was different and everything, like for me, I had so much curiosity about things around me and the world that it just set me up for wanting to travel. And I remember memorizing all the capitals of every state of the United States, and then like even some other capitals of other countries and things like that.


And then in school, I even had one class where we would study a country like really in-depth. And that just got me thinking about that kind of stuff. And then, yeah, I think later on, I read Tim Ferris’ 4-Hour Workweek and I just clicked. It was like I was already thinking of these things. I almost thought like I could have written this book because I was already thinking like, I don’t want to just stay in one place my whole life and I’d like to travel. I like to move around and see places, whether it’s in the US or other places, and really get to know these places and get an idea of what it’s like to be there. So, yeah, that was kind of my start, so.


Justin Donald: Oh, I love it. And you’ve got the world map in your background. What you can’t see in my office, you’ve got a view of my bookshelf. For those of you that are listening and not watching where I have some of my favorite books I’ve ever read behind me here, some books that were inspirational. But what you don’t see is on the wall over here is a full-size wall map. It’s a magnet map.


I’ve got these little pieces that I can put in and I like putting them in where I went to this place on my own, I went to this place with my family, I went to this place with my daughter. I proposed to my wife in Bali. And so, we’ve got all these magic special moments. I’ve got all these little– they’re not pins. I used to have the old school map, they had a pin. And these are like the nice magnet things, although sometimes my cleaning team wipes them off, and we have to redo them, but…


Kevin Koskella: That’s real problem, right?


Justin Donald: Yeah, first world, for sure. But I just love to travel. I mean, my goal is to go to every country in the world. People think I’m crazy about that, but I just want to experience everything. And I realize that there are some places that maybe we wouldn’t be considered safe to travel to. I think in time they may be. But I also think that we’ve got a lot of media that kind of overexaggerates the danger of a lot of places.


I mean, even with a place like Colombia, we are going to Medellin. A lot of people here call it Medellin, but Medellin, Colombia, as they call it. And people here thought I was crazy, like, oh, no, don’t go there. You might die. And it’s like, no, no, I mean, there are certainly rough areas in any city. But we spent time, extended time. And many trips, we went there. We had family that was living there for five years. So, we spent a good amount of time over there and never once did we feel in danger. My wife went when she was pregnant. My wife went alone one time when she was pregnant.


And so, it’s just a beautiful country. But I think sometimes, if we listen to, I guess there are some fear mongers out there and people that want to create some level of news then, unfortunately, we miss out on these just gems. I want to call them hidden gems, but it’s not so hidden anymore. Like people are catching on that, hey, you can travel most places in the world pretty safely.


Kevin Koskella: Yeah. Instagram has kind of ruined that because there were hidden gems before. But now, everybody knows about them because of Instagram. But yeah, that’s true. The media definitely gives you the fear-mongering, and it’s really important to kind of like use your true self and then to think about this like what is it that you really want? And do you want to be kind of led around by the media and the fear and just kind of shelter yourself into a world of safety over having freedom? That’s not something I would ever choose. I know you wouldn’t either, so.


But yeah, I think that there are people that go through, there’s like YouTubers that go to the most “dangerous,” but some of them are actually dangerous places. And it’s really interesting. Like there’s a guy that I follow sometimes on YouTube. He’s Indigo Traveller. He goes to the most hardcore places. He’s gone to Afghanistan. He’s gone to like all sorts of places in Iraq, Iran. He went to Favelas in Brazil. I mean, he just goes to the most dangerous places. And he walks around with a camera and interviews people. He usually has a guide with him, but it’s like he’s never had any problems. So, it’s like, if he can do that, then we can go to Medellin.


Justin Donald: Right. Yeah, there’s no doubt. And by the way, I can tell you that like the favelas– I mean, what was that movie? City of God, I think.


Kevin Koskella: Yes.


Justin Donald: Which is just an incredible movie. But I mean, that is a depiction of what the favelas or the slums of Brazil, Rio de Janeiro specifically, are like. And we got a glimpse of that when we were there. Of course, I mean, that can be extremely dangerous. I don’t know that I would ever go in there, but at the same time, there are ways to be able to experience these things. There are ways to get into different cultures and different cities, different areas in a safe way. And I know that we just share this love for travel.


And by the way, part of the beauty of why you get to travel is exactly why I’m having you on the show, Kevin, which is, I love to interview lifestyle investors. What’s a lifestyle investor? Someone that has a lifestyle first orientation that has income that is covering their cost of living, that has made some investments where they have assets that really produce opportunity, cash flow, whatever it is.


You’ve done a lot of things, and I’d love to talk about your story and how you got to where you are because you’ve had success as an online entrepreneur, you’ve had success as an investor, you’ve owned real estate, you’ve owned Bitcoin early on and other cryptocurrencies. Like, there’s a lot of cool things that you’ve been able to figure out that have bought you this freedom that you now live and have and share with others. And I’d love to hear kind of how you got started.


Kevin Koskella: Yeah. So, I got laid off during the dot-com crash and I thought my life was over for a bit and I didn’t know what I was going to do because I was living in San Francisco, and the rent was insane. The rent has been insane in San Francisco since like the mid-90s. And so, I just sort of kind of pursuing some of my passions rather than trying to get more money. And I realized that I didn’t want to go back to the corporate world.


So, instead, I was reading all these books like Rich Dad, Poor Dad and I started realizing that I’m just not cut out for this corporate thing, and it doesn’t even make sense. And so, I thought, I really want to be an investor, I want to be a business owner. Those are the things I want. I want to get to those quadrants.


And so, I started doing like a self– it has the S quadrant where you do your own, it’s like you’re self-employed. So, you have to be there to make the money. And I did that for a while, but that was the way to get more freedom. But I felt actually not free at all. And I was making not much money at all.


So, I was like, man, there’s got to be a better way to do this. And then just randomly, I came up with this idea because I was teaching swimming. That was one of the things that I was passionate about at the time. And I came up with this idea because a lot of the people that were coming to me were triathletes, adults looking to get better at swimming or to learn swimming for triathlon.


And so, I’m like, huh, I wonder if anybody is teaching that online? And I found that really there was nobody. And so, I’m like, I’m going to do that. I’m going to create a website that is just triathlon swimming and just do that. And then, luckily, I had a mentor. I had somebody that taught me all about online business. And so, I was able to create a little website.


And yeah, it just started, I made my first sale of my e-book, or wasn’t even an e-book really, it was a PDF file. And that was enough, just that one sale was enough to be like, I’m done with corporate world, I’m done with jobs. I can’t go back to that. Even if I’m super poor and I’m making a little bit of money online that I can live off of, that’s much better for me. So, that’s how I kind of got into the whole, like creating business and doing things online.


For me, it was not an overnight sensation or success or anything where I don’t have a story of, oh, and then three months later, I was making 10 grand a month. It was like, no, it was like the first month, I made $50, then the next month, I made $150. And it was like that kind of thing, like really slow, but the fact is, it was a progress, and I was making money without being there.


It was like, I was on a flight to Europe and I arrived and I hadn’t even checked my email. I was like two days of not checking email and I had put my first product up. This is the PDF file. And by the time I checked my email, I was in one of those cafes where everybody was smoking weed and stuff and I had to check my email. There was a guy that had bought my PDF file and he was pissed. He was angry because he didn’t get it. I was like, oh shit.


So, I was freaking out. But then I ended up like, my first thought was, well, I made $15 while I was flying to Europe. Like, that’s amazing. Like, that is so mind-blowing. For me, at the time, it was. And then from there, I’m like, I fixed the problem. And then I started getting better, and the whole experience was much better after that. And then I built the website, I built up that website so that then I was selling DVDs, it wasn’t just like a little e-book, it was a DVD. And then it was a membership site. So, then it was like a full-blown thing where I was the resource for triathletes looking for swimming help. So, that’s what I did for a number of years.


Justin Donald: Yeah, that’s incredible. And what’s neat is I feel like you’ve had some great experiences where you figured things out and you learned some great lessons because you did well. You’ve also learned some great lessons because of failure. I know we’ve talked about this with even your real estate portfolio where it’s, at one point in time, I think you had built up this big single-family home portfolio. You had at least some single-family home rentals. I know that. And I think you may have been swayed into or your emotions led you to believe that you needed to sell during a down cycle, whereas I know we’ve talked and you’re like, if I would just hold on, and all of us could do that. But I think it’s the pain that teaches us the lesson.


When things are going great, you don’t learn the lesson as well. It almost doesn’t even register as much. So, it’s cool to go from the experience of, hey, I just made 15 bucks while I was on a flight, then compound that however many times over whatever time frame. And I know you’ve done very well in that space and you’ve done other niche projects like this, which is cool. But walk us through like your real estate experience, what you learned, what maybe you do next time, how that shaped your investor IQ.


Kevin Koskella: Yeah. And I wish I would have done what you did with the mobile park homes because that was something presented to me back then. This is like mid-2000s. I started getting into real estate because I just always liked real estate. I always thought it was cool, like just the whole thing about it was appealing to me.


So, I got in when you could get nothing down loans, like everything was so easy. And I started looking at, I was living in California, I was living in San Diego, and the numbers there just didn’t make any sense. So, I started looking out of state and I was looking at Arizona, and then Arizona was getting crazy. So, I went to Texas, went to Austin, and Austin at that time was super mellow. There wasn’t a big real estate boom going on. It was just kind of the norm. It was a flat market.


And so, I ended up starting to buy some properties there with no money down. I mean, you got to pay the closing cost, but it was like not that much. So, I started acquiring all these properties and I started with a duplex and then I bought a single-family home. And my idea, it’s a little more in-depth story than just like I bought them, I held them for a while. I had a plan to do rent-to-own, lease options. And I had all my properties on this option except for the duplex.


But everything, all the single-family homes that I was acquiring, I was putting right on a lease option. It was a great business. You can get people in. It’s a higher-quality tenant. They will pay a much bigger deposit. It’s non-refundable. They will pay more rent because part of their rent is going towards their costs. If they’re going to buy the house, they have the option to buy the house in either one or two years. So, I was doing that, and it was great.


And then Texas, out of nowhere, the state of Texas decided to make lease options illegal. So, my entire business plan shattered. And then I had these houses where I was like, I pretty much had to turn them into just straight rentals because unless I wanted to just break the law and I just didn’t want to mess around with anything. So, I just turn everything into a straight rental.


And then my whole life changed for the worse because suddenly, I had all these problems that I never had before because before, I had these people that wanted to buy a house and they were pretty close, but they had some credit issues or they needed to get a little more money. And then, I’m just dealing with the average tenant, and the average tenant is not very good, as you probably know. It’s like they’re difficult. And there are just so many problems. I mean, I have story after story after story about people that were flaking on rent, that disappear, that they had a story that they wanted me to wait on, not like the rent. So, that started happening.


So, then fast forward a couple more years, and then I got a divorce and I ended up, we had 10 properties. And then they were pretty much all pains in the as*es. They were all like really difficult to manage. And so, she gave them all to me and said, you can have them. I’m like, all right, I’ll take all of them. Because it was a burden, it wasn’t something where she didn’t want them, and I really didn’t want them either. But I was like, all right, we’ll take them.


So, this is like 2007. I started selling them. I got to get rid of these because I didn’t want the responsibility, I didn’t want the headaches, I didn’t want any of the stuff. So, I start selling one by one by one. I sold six houses, and then the market just completely went to a screeching halt. There was like no buyers. I mean, there was nothing. I was like nothing I could do.


So, I had to keep these four properties and I was forced to keep them because I couldn’t sell them. So, I made the best of it. But I had a lot of months where I was underwater or I was losing money, and it was really, really stressful. So, my goal in life was to sell everything I had because I just didn’t want the stress even though I had property managers and all that. But even now, you have to manage your property manager, and that’s never fun.


So, I started looking at it going, okay, I don’t want to do real estate anymore. But that was around the time at some point Bitcoin came out, and I was like really intrigued by that. So, I kind of shifted my entire focus to Bitcoin and crypto, in general. And knowing that I didn’t have to deal with tenant problems, it was like, I mean, monumentally better, so.


Justin Donald: Yeah, it’s interesting. I love your story because there are so many positives and opportunities. And one of the things you talk about is this lease option. And I love a lease option. And by the way, for all intents and purposes, there are probably some grandfathering laws if you really dug into it where if you had a lease already signed, you may have been able to keep that lease without penalty. I mean, we’d have to dig into it.


But we always talk about pride of ownership. When you own your home or if you’re on a lease option, sometimes we’ll call it a rent credit, depending on the property, you have this opportunity to bring in tenants and we like to call them residents that really want to be homeowners. And so, they care for the home like it is their own. And it is a whole different type of tenant or resident than a pure renter.


And so, I think you’re on to something there. But flip side, so, yes, we could talk about like, oh, if you’d only held on, look what’s happened to Austin. But at the same time, you made a very calculated decision and this is where you pivoted into Bitcoin and you got in pretty early. And I would say of anyone I know, you’re one of the smartest, most well-rounded people in the crypto space, even though you like to keep a low profile. I’ve learned so much from you over the years and I just love to hear a little bit more of your rationale and when you got in and kind of that journey with Bitcoin and expanding beyond Bitcoin into crypto.


Kevin Koskella: Yeah, for sure, man. Yeah, I love our conversations about Bitcoin too. We’re so aligned with the principles behind Bitcoin and everything. And that’s how I got into it, was the principles, like for years, I saw that the fiat money system was not going to last, like all fiat currencies die, they all die.


And the US dollar is not special, it’s backed by military force and it doesn’t have intrinsic value, like there is no intrinsic value in the dollar. So, I knew that the dollar was going to crash eventually. It was going to come way down, and I was a little bit ahead, like I was thinking a little bit ahead because I thought it was going to happen in the mid-2015, 2016, 2017, something like that. But somehow, it’s still hanging on and it’s still maintaining some value.


But that was the initial thing. I could see that there was something that was needed. It wasn’t a government currency, and Bitcoin came along and it was like it’s decentralized. That was the main thing that I was like, wow, it’s totally decentralized. There isn’t a Bitcoin CEO. There’s not a Bitcoin founder that someone could contact. There’s no way to bring down Bitcoin itself. Like you can’t just– and I thought that was just so awesome.


And so, when I started, I had no money. I literally had no money. And I’m not lying, I’m not exaggerating about that. But I got a little bit of money over the holidays, Christmas. And obviously, it was a gift. And I was like, well, I got 300 bucks, I’m going to put it into Bitcoin. And in my head, I was like, I’m prepared that this $300 is gone. Like, in my mind, it’s gone. I’m putting it into Bitcoin. It’s essentially just gone.


And I didn’t think that it would go up in value. I just thought I’m probably going to lose it, but I did think that it’s safer in the long run because it’s not in the dollar. And I’m like, I want to get out of the dollar. I want to get into something that’s decentralized. So, I started doing that. And then every month, if I had 100 bucks, I would just put it into Bitcoin. I was just like little by little, and it was going up and it was like, wow, this is actually going up.


And so, all of the gains, all of these big moves and stuff have always been really surprising to me. Like, I’m never prepared. I’m a terrible day trader or short-term investor. I have no idea where anything is going. People will ask me often, like, where do you think it’s going? Where do you think Bitcoin’s going? And I always have no idea because if I start to think, if I start to take guesses, I’m almost always right, 80% of the time I’m wrong.


So, I’d just rather be that long-term dollar cost average and just keep putting a little bit in, a little bit in, and in the long run, it’s going to be great, and that works for so many things. But for me, that’s the only style of investing in Bitcoin that I do. I don’t have any tricks or trying to catch the bottom. I mean, I have no idea, even right now, like, have we already bottomed out or is it going to go for I have no clue?


Justin Donald: Well, it’s interesting to hear that. And I think that’s such a healthy perspective because no one really knows. I mean, people speculate all the time. The smartest people recognize that no one knows. Just like no one knows what’s going to happen with the stock market. No one knows. Some people may guess it right, but those people aren’t going to consistently guess it right.


And even when you have a track record of guessing it right for a period of time, you’re going to be wrong. No one knows. And when we can keep a level hat on our shoulders and say, hey, we don’t know, I like your strategy, though, I’m in it for the long haul. I’m going to dollar cost average in. I’m going to start with 300 bucks. And then every extra hundred bucks I have, I put in. And that doesn’t sound like a lot of money.


But over time, in a growing asset that it definitely can be. And the idea here isn’t to take, like I know some people, it’s a very small percentage, but I know some people that kind of did the, all right, I’m all in. This is Texas Hold’em style. I’m pushing all my chips in. It’s a very, very small percentage of my friends that did that.


And by the way, they’re reaping the rewards of having done that. Most of the people that I know that did this, they made some calculated move at some point in time. They weren’t sure if it was– no one really knew. They’re hopeful that maybe it went up and this was good. But I think the purists would say, hey, I believe in the ideology of having a decentralized currency. I think that’s better for the long run.


And if I’m in this long term, then it really doesn’t matter what the highs and lows are because I’m playing the long game. And if I look at it from a long game standpoint, every dollar in, every dollar out, this is just a dollar cost average over a long period of time. And so, that’s something that gives me a lot of peace of mind that I don’t have to time the market.


I’ve just found if you try and time the market, you miss, then you feel bad about it, and then you wish you would have done it differently. I’ve just come to the realization, and anything I’m investing in, I’m probably not going to time the market great. Can I time it well enough to like that it’s long run a good decision? I can feel good about that. But that takes the pressure and stress off of like, ooh, you have to buy at this price. I just said, hey, if I believe in something long-term, whether it be real estate, Bitcoin, operating companies, you name it, if it’s a long-term play, and I think the value long term is going to be greater than the price today, then that’s a buy. And I don’t have to get all bent out of shape about timing, which takes so much stress out of making these decisions.


Kevin Koskella: Yeah. And it’s like that Andreas quote where he says, people asking me my strategy, and I say, buy on Mondays. That’s it. Like just buy on Mondays and always do it. You don’t have to look at the price and go, oh, it’s too much. I mean, I remember, this is back when I was living in L.A., I was talking to this girl at a happy hour, and she’s like, I really want to buy Bitcoin, but it’s so high right now. And I’m like, how do you know it’s high? I don’t know that it’s high, I don’t know that it’s low. I have no ideas.


At the time, I remember it was $5,000 and she’s like, yeah, I’m just going to wait for it to go down a little bit and then I’ll buy. And I’m like, okay. And then we went to the same happy hour like two weeks later or whatever that was, like two or three weeks later. And I’m like, oh, did you buy? And she’s like, no. I’m like, well, it doubled. Like, it went to 10. Now, it’s 10. I’m like, is it now? And she goes, now, it’s way too high. I was like, how do you know? How do you know it’s like going to 20? I mean, you just like– so those are things, the FOMO and just the fear and greed thing is such a crucial thing.


And I learned so much of this, just being in Bitcoin and watching it and seeing that fear-greed. There’s a fear greed index where you can see how much fear there is in the market. And that’s a pretty good indicator. Of all indicators, I would say, that is one that is pretty accurate where when the fear is the highest, that’s when you want to buy it. When it starts getting into greed and everybody, like last year, when everybody knew it was going to 100k, we all knew it was going to 100k, that’s when you want to sell, so.


Justin Donald: That’s right. And you’ve got to learn to not trust your emotions on financial decisions. So, this is why I talk to my mastermind all the time. With anyone in The Lifestyle Investor community, I say, have your investment criteria, figure it out when you’re in a good place, in a good standing of sound mind, not emotionally swayed of what decisions you want to make, what type of cash flow you want to have, what this looks like long term. So, that way, when it comes to making these investments, you can lean back on this one-page investment criteria and say, oh, I actually said, back then that I was going to buy at inside of this window or I wasn’t going to be swayed when the price drops and I can hold. And so, I think that is just a really smart practice to put into place.


And then the other thing is we don’t know what this is going to do long-term. Ideologically, I think that this is unparalleled to anything else that’s out there. I think that it stands alone. Bitcoin specifically is kind of a stand-alone product with no rival today and it solves a lot of problems. So, to me, and again, this is not financial advice, I don’t give financial advice. I just like to share some of the things that I do.


But just like people, just like experts say, you should have 1% to 2%, maybe up to 5% of your net worth in gold and silver. I feel like the same is true. Like what if it was half a percent or 1% or 2% of Bitcoin where if anything goes wrong, it dies. You’re not out. No one’s at that low of a percentage of net worth. No one’s losing all their stuff.


But if it does take off, you’ve got a piece of something that’s pretty big and some exposure. And this is kind of how I like to treat any of these new frontier markets, frontier industries, whether it be cannabis investing, e-commerce. Any of the new trends that come in, if you pay attention to like where are millennials spending money, what are the spending patterns, what are the businesses, what’s the technology that’s going to boom?


I like to be on the cutting edge of that, and I like to at least have a little bit of an allocation of my portfolio into these different things because it doesn’t take a huge amount of money to make a lot of money, especially when that investment is already coming from cash flow of assets that are basically producing passive income. Then you’re not trading principal that could be earning you cash flow. You’re actually using the cash flow of that investment for something that maybe you would deem a little higher risk.


Kevin Koskella: Yeah. And I think in the coming years, we’re going to have opportunities with what you just said with Bitcoin. Like you can make money on your Bitcoin. It’s there now, but it’s just in such early stages that I haven’t dabbled in it at all, but I’m sure that we’re going to get there. Where I saw there was a new thing that just came out where I think it was one of the companies, I can’t remember which one, not BlockFi, but the other one that’s similar to BlockFi. They’re offering to be able to invest in real estate with Bitcoin. And it’s kind of like where you still hold on to your Bitcoin, but you’re able to use that to invest in real estate. So, it sounds interesting. I’m not quite there ready to do that, that kind of thing yet, but I think, in the next two to three years, that’s going to be really common.


Justin Donald: Yeah. The industry is going to continue to evolve as more mass adoption happens. You’re going to have better technology. You’re going to have better supporting like architecture, infrastructure, a lot more optionality with what you do. And I also think that like the winter that has happened where we’re in this bear market, both for the stock market, but also the crypto market, it pushes the fools out. It exposes the frauds.


And I think that’s good because you can learn from, hey, let’s not do this or let’s learn from this company that ended up being a Ponzi scheme or whatever it might be. Like, I want to flush out all the junk that’s out there so that we can streamline better practices and ideology and programs that are actually going to work. It’s really cool to me some of the stuff you’re doing, Kevin, because you’re financially free. You don’t have to work. You get to work. You have the choice of being able to work. You spend a lot of your time traveling and you spend a lot of your time like coming up with just different cool ideas.


And so, you’ve got this new book that I’m so excited to talk about, where you want to help educate people about kind of the inner rebel in them. And the name of the book is called The Rebel’s Guide to Freedom: Becoming Resilient, Owning Your Life, and Thriving. And I love the title and I love everything that you’re doing there, but I’d love to know more. Tell me, tell all of us, those watching and those listening, what it is that you’re looking to accomplish with the book. I’ve got it right in front of me right now.


Kevin Koskella: There it is.


Justin Donald: There you go. Perfect.


Kevin Koskella: Yeah. So, we’re just printing it now. So, it’s going to be out in about two weeks, two weeks from the time it is recording, August 16. Yeah, so talking about freedom…


Justin Donald: Just to clarify, those of you listening right now, it’s probably out right now.


Kevin Koskella: That’s right.


Justin Donald: We’re launching this in tandem with Kevin’s book launch. So, don’t wait two weeks. It’ll be right now.


Kevin Koskella: Yeah, that’s right. So, yeah, thank you. That’s great. So, I’ve always been a freedom-loving person. And I started a podcast in 2013 called Freedom Lovin’, so, Freedom Lovin’ podcast. And I started just interviewing people and talking about freedom and all the ways in which the world is not free and how we can get more free.


And through the years, I just really honed in on freedom, the idea that freedom is an inside job, like all the politics and all the external factors and things like that are not how we’re going to achieve freedom, both either individually on the individual level or on a bigger societal level. We can’t achieve freedom unless we dig inside and we really figure out ourselves.


We understand ourselves, we have more self-knowledge. We know, like what motivates us. We need to heal those traumas that maybe are holding us back, the beliefs that are holding us back, like all those things are the only way that we are going to achieve freedom because, as we know, the world is going pretty crazy right now. And that’s what really motivated me.


So, in the summer of 2020, I was up in Taos, New Mexico in the mountains. I was staying in a ski resort where there was no people and I was just by myself. And I just randomly decided to write a book. And I was like, I never thought I’d ever really thought much about writing a book, but I just decided to do it.


And I was motivated because I think that the world needs this message right now. And it’s not necessarily that there’s one thing and there’s a silver bullet or here’s the top 10 ways that you can be free or anything like that. I think those things are kind of overrated and I think there’s a lot of deeper stuff that we need to work through as individuals. And so, that’s what my book is really about, it’s like, look, the world is pretty crazy, and how can we change this? Because there are so many people that have the ideas of how we can fix the world and make it a much better place and not have these lockdowns and shutting down businesses and isolating people and all this stuff that is so anti-human.


It’s anti-everything that most people really stand for, like freedom, love, autonomy, all these things that most people really value. And it’s kind of turning in this other direction. But the way to change that is not to write your congressman or go vote in the next election, like that’s really not a viable way to change things around you.


So, my book gets into the idea, I started out really by talking about some of the problems. Then I get into like what is safety and what is security? And does it make sense to trade that for freedom, to exchange some level of security or some level of freedom for security? And I get really deep into that concept because I think it was really misunderstood by so many people in the last couple of years. And yeah, and then I go out from there and then I go into like some of the personal stuff of relationships, money. Like how do you look at money? How do you look at success?


I mean, something I want to talk about on this podcast is, what is success? I feel like a lot of people, they inherit the idea of what success is from their parents or maybe from their peers or from school or something where they just see, like, oh, success is being a doctor or success is making a lot of money or success is doing something that my parents would approve of, that they would be happy with. And those are how a lot of people would define success.


But it’s really up to you, as an individual, to define success. You define it in your own terms. I mean, I never was money motivated, but I was freedom motivated. And to some level, freedom takes some level of money. So, I knew, I had to get to a certain point to have some freedom in that realm.


But I mean, I’m a minimalist. I love minimalism. I think it’s awesome. And that fits me great. And I would never preach it and say that everybody should be a minimalist. But for me, that’s worked, and I’ve been able to define success in my own way of like, how free am I? That’s what I always ask myself, like, am I doing the things I want to do? Do I feel free? And then, money is down the line. Like, I don’t need a lot of stuff. So, I don’t need this really fancy car or big house or anything like that. So, it’s a little bit different.


And so, I never know what’s going to define it all the difference. So, I think there’s a lot there that your audience here could probably just kind of take a step back and think about like, what are you doing on this planet? And then how are you defining success? Are you always on a treadmill where you’re like, I got to prove myself, I got to prove myself? Well, then you’re not really free.


Justin Donald: Yeah, the achievement treadmill. It gets to the point of you talking about being minimalistic. And Jennifer, my wife, I would say she’s less minimalistic than she was when I met her. But she’s very much in the camp of having less and not to the extreme that you’re at, Kevin, but there’s just this beauty to not having things own you. And I think what I see around me is a lot of “successful” people own all these material possessions, but in reality, those possessions own them.


So, if you own another home and you’ve got another mortgage and it takes a certain amount of income, maybe you’re not renting it out or maybe you’re not fully covering it, I’ve got a lot of friends that own other homes and they don’t like to run them out because their goal wasn’t necessarily to make money, they just wanted another home. And so, then they have to work hard at their job or their business to make the money to cover that second mortgage. And the list goes on and on of those types of things, whether it be a boat, a plane, an additional car, whatever it is.


And I think we’ve got to be careful that the possessions that we want to own so bad, they don’t create the golden handcuffs of tying us down to something where we have to make a certain income because we become accustomed to this lifestyle and this certain expense. And you had said something earlier about kind of safety and security. And I actually want to bring– I’ve talked about this before, but I want to bring this up again. I think in a lot of senses, safety and security is an illusion, right?


People think, for whatever reason, the banking industry thinks that if you have a W-2 job, you have a safe job compared to an entrepreneur or a sole proprietor that has a “risky” job. And during the pandemic, we’ve learned that at any point in time, people can get fired and their safe job is not really a safe job. And I think that there’s this illusion of safety, this illusion of security, where I’ve got friends that live in a gated neighborhood. Why do you live in a gated neighborhood? Well, it’s nice, and I’ve got kids and I want to make sure I keep them safe. Hey, that’s great. I hope that we can live in a world where we can keep our kids safe.


But the reality is, a gated community is an illusion of safety. It is not. I mean, if it gives you the peace of mind, great. By all means, do it. I think that’s awesome. And for some people, they live in a gated community for other reasons. But the whole idea of a gate keeping a perpetrator out is laughable. Like, there’s no gate that’s going to keep someone out that wants to get in.


Kevin Koskella: I live in a gated community. And there was a car that was stolen here last year. I mean, my car was broken into where the gate is.


Justin Donald: That’s right. And so, security and safety is not sometimes what we drum up in our minds. And I think the more that we can get in touch with what is real safety and security, well, I think that’s having great health, I think that’s having great relationships I think that’s being intentional with life and living life on your terms, like that is you’re going to find fulfillment in that which is going to feel a lot better than just safe or secure, though you may still have the byproduct of doing what you want so you do feel safe and secure.


Kevin Koskella: Yeah. And then just what is safety? And what was safety during COVID? Now that we look back on it, we can have different views on what– at the time, a lot of people thought that safety was staying inside and never leaving. And if you did have to leave, you would strap on the mask, the double mask, and put your gloves on and go grocery shopping. And that was safe.


But then it turns out that we actually need something called vitamin D and it comes from the sun. And avoiding that was actually making people more vulnerable to viruses and things like that. So, you end up with what they call the pandemic. And everything turned out to be, a lot of it turned out to be backwards. What was safe was not actually safe.


And then, giving up your freedoms in your life is not actually leading to any sort of happiness. So, when it comes to safety, you always have to weigh out all the costs. It’s not just like, oh, I could be safe by never leaving my house. But what about all the other costs that it involves? What about things that you like to do? What if you like to go to the park and the beach and all these things, and then you’re like, but I want to be safe. And it’s like, well, where can you make that balance? Everyone’s going to be a little different, obviously, but there isn’t some top-down. The government can’t tell you how to be safe. That’s impossible.


Justin Donald: Yeah. And you talk about this big in your book, like where you start talking about like just this whole idea of traditionalisms and like a lot of people not questioning things and just taking it as is. And I think about, even with my parents, my parents would say things that today, I take as a fact, even though I didn’t do my own homework, I didn’t question it. I just kind of took their belief system as fact without doing my own due diligence on it. And I’d love to hear some of your thoughts about that, like mindset, worldview, traditionalisms, and what you believe around that.


Kevin Koskella: Yeah. Well, I talk about this in the book, but we all go through, most of us go through a rebellious phase. There’s an inner rebel in most people, like that’s just normal humanity. We have a rebellious phase, and it manifests differently in everybody. Some people might turn into like a punk rocker and shave their head and have a mohawk, whatever, and dress in a tattered leather jacket with a little– I mean, that might be some version of a rebel, but that’s only one version. And some people might just rebel quietly inside and be like, yeah, I don’t really fit in with everybody here. So, I’m just going to kind of do my own thing. And that’s their version of rebelling.


But what a lot of people do and what I think that we need to change, each of us individually, is that they sort of reject that inner rebel. They go through the phase and they go, oh, that was just a phase. And then they get to be in their 20s, 30s, they start having kids and they’re like, yeah, I need to be an adult now. That was just something I felt like when I was that age. When I was 19 years old and 20 years old, I was that way. But I’m not that way anymore and I need to go with whatever the program plan is. Now, I need to be like everybody else in society. I can’t rebel.


And I think that’s wrong. I think it’s not that we should all be super rebellious our entire lives and rebel against everything. I mean, that’s an unhealthy way of rebelling, but we should hold on to some of that, that part, and realize that it’s going to be with us our whole lives. And so, to have that part be heard within us and to say, yeah, I recognize that I still have that part and I can use it or I can have it come out in healthy ways that can help me.


Like, for example, being a contrarian investor or something, where you’re like, no, everyone’s doing it this way, I’m going to go do it this other way. And it’s the same thing in your life where you’re making all these decisions, and how much freedom are you going to get by just doing things the way it’s always been done? That’s the thing that has held humanity back is when people have this traditionalist mindset where it’s like, you ask somebody, well, why do you do that? Why are you doing it that way? And they say, well, that’s how it’s always been done.


But they haven’t even thought about all the other ways that it could be done, that an entrepreneur could come and solve, like, oh, there’s a better way here. And that’s how this inner rebel can come through and can create businesses and do things that have never been done before. And it can really make humanity move forward in a way that is beneficial to everybody.


Justin Donald: Yeah, there’s no doubt. I mean, I love hearing you speak and share kind of your belief systems and your thought process. And by the way, being a contrarian thinker, a contrarian investor, that has really served me well because I got into a lot of things that people said, don’t do it. When I got into really specialized dividend paying whole life, I used someone that is really outside the box, crafting these unique policies that no one else is doing, no one else has heard of.


And people in my network said, don’t do it. And this was back when I was single, I wasn’t dating anyone, I didn’t have kids, but I just saw that this is what the wealthiest of wealthy did. And so, I was like, well, I would like to get my start. And that has proven to be one of the best things that I’ve ever done because I basically have my own bank now that I can borrow against for all the investments that I do because of funding that for 15, 20 years, mobile home park investing.


People told me I was crazy, that I should not do this. And this happens to be one of the most sought-after asset classes out there, even with single-family homes before that was an asset class. People are like, are you crazy? What are you talking about? And now, it’s actually an asset class, and people love it, like the big institutional PE firms are buying these up like crazy.


And so, I think it pays to think through and not just follow the crowd. And I would say with conventional investment wisdom, do not follow the crowd because most people do not have it right. If you look at how many people are retiring the way that they want to retire, the way that they thought they would retire, it’s a very small sliver. And that’s because most are following this traditional approach.


That is like what Wall Street says, which is just it’s totally flawed. They want your money. They make a ton of money. You may or you may not. And the people that are selling these packaged products via financial planners, advisors, etc., a lot of them aren’t questioning it. They’re just like, hey, this is the way that it is.


And so, I think it’s important that we kind of ask our own questions and come to our own conclusions and really dig in and just try to figure out, just say, hey, could things be different than the way that they’re presented here? Could I do things a different way? What could the reality be? And I think you’re posing some great questions and some very thought-provoking topics, Kevin. So, if someone wants to learn more about you, get your book, learn about your podcast, just dive in more with you, where can we go to find out more about you, Kevin?


Kevin Koskella: Yeah, sure. My website is So, that’s Freedom Lovin with no G at the end, dot com. And yeah, that’s really the place. I’m going to have all the book information there. I’ve got a weekly podcast. I talk about these kind of topics. I talk about some of the more macro stuff as well. I get into Bitcoin, a lot of the decentralized sort of countering these ideas to the mainstream ideas. I talk a lot about that and how you can achieve more freedom and how we can achieve more freedom as a society as well. So, I get into that on the podcast. And then, yeah, the book is just at I’m not really doing a lot of social media, but I’m on Twitter @freedomlovinway.


Justin Donald: Awesome. Well, hey, Kevin, thanks so much for joining us. This has been an awesome episode, and I just want to share with my audience that if you’re looking for more content like this or more investment deals via The Lifestyle Investor Community, apply to join the world’s most exclusive mastermind that turns everyday people into savvy investors who really regain control of their time, build their wealth all through investing in invisible deals not available to the general public. These are deals that have been de-risked with preferred terms, accelerated returns, oftentimes. So, you can learn more at


And I want to close out our episode today the way I do every single week, which is this. What is one step that you can take today to move towards financial freedom and living a life that you truly desire that’s on your terms, so not by default, but by design? Thanks for tuning in and we will catch you next week.


Kevin Koskella: Thanks, Justin. That was awesome being on your show. I really appreciate what you’re doing, why you’re doing your business, your lifestyle, and you’re helping the world. So, really appreciate that.


Justin Donald: Thanks, Kevin. I really appreciate you saying that. And it’s always a pleasure to connect.

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