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Ep. 164: How this remote entrepreneur has created a unique business coaching surfers online with Chapin Kreuter

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In this week’s episode, I speak with Chapin who is an online entrepreneur and podcaster who has lived primarily in Nicaragua since 2005 running surf tours. 

Over the last 5 years, he has been podcasting and starting online businesses. 

His podcast is called Misfits and Rejects where he talks about lifestyle design of ex-pats, travelers, entrepreneurs, and adventurers. 

Listen on to find out how Chapin has created a unique online business as a surfer.

Listen Below:


Ep. 163: Bonus: How to land your first remote gig with Andrea Valeria

Ep. 162: How this nomad works remotely as a small business consultant with Susan Brooklyn

Ep. 161: How this remote brand designer helps women grow their brand with Chelsea Blackwell



Hey everyone! Thank you so much for joining us. I’m so excited to be here with Chapin.

Hi, how are you? 


Hey, Debbie. How are you? 


I am wonderful. Can you tell us a little bit more about you and why you live an offbeat life? 


Well, I found myself just young and excited to travel. And once I got that first taste of I’d say, life on the road or life as an ex-pat, it really sort of solidified a lifestyle that I wanted to pursue. And from that moment on, I just started trying to design my life in a way that I could maintain myself in, like, another country or a life on the road.

And it’s been kind of my mission for the last, I don’t know, I’d say fifteen, twenty years. And then the last five, I really started honing in on the online business side of things and trying to make my life location independent through that. 


When was the moment when you finally realized, when you had your “aha” moment that you wanted to go into this lifestyle full-time and kind of ditch your regular life, regular job and start traveling the world and start your own business?


The “aha” moment came for me when I visited my friend in Costa Rica and he’s living in a full jungle hut on the beach in Puerto Viejo, Costa Rica. And I saw how  simple his life was and it really was just in line with my value systems and how I want to design my life. That was really my “aha” moment. 

And then, having gone through years of making businesses in Nicaragua, Central America, and third world countries, it was a great lifestyle and I really like that lifestyle but I have my second “aha” moment when I came across Pat Flynn searching online how to become, like, more location-dependent for my job, create passive income.

And I stumbled into this world of being a digital nomad at making money online. The light bulb went off and that was like more of a sustainable model I felt for me and what I really wanted out of life. 


How did you decide what you actually wanted to do? Because when you look online, even going into articles, podcasts, and everything else in between, there’s so many different options that you’re given. 

But then, it becomes paralysis of analysis because its too much. How did you do that? How did you decide what was right for you?


Well, Pat Flynn became a really huge influence on me. And I was just listening to every single podcast he did, absorbing all his information and still really striving with a goal to create passive income. I really wanted to generate, like, five hundred bucks a month through online something that was passive because that was what I really kind of needed to sustain myself on the road in all these places like Thailand or whatever. 

And so, he first started talking about eBooks and in my mind started going in that direction. And then I heard a podcast you did with David Siteman Garland about creating online courses. And once I heard that, like, every cell in my body said, “That’s what you should do,” create an online course with a subject that I know really well which was surfing at the time or it is still.

So, I just started going down that path and, I mean, it took way longer than I expected. My goal was to start generating passive income through an online course within, like, 6 months of learning about how to build an online course.

And then, the end took two and a half years, then, three more years of trying to figure out how to market it, to actually generate passive income through it.


Well, it’s incredible that you heard about this and then you just dive into it. And I think, for a lot of us, we think it’s going to take this amount of time and then we realized years later that it’s going to take longer than what we had expected it to be. 

What was that process? Like what was the first thing that you did to actually become someone who could create a successful course? 


Well, I had to go through and learn the tech things that all these salespeople say is like, ”Oh, it’s not that hard. It’s not that hard to learn how to use Keynote or use ScreenFlow.” And I just started chipping away at every single third party app I needed to create the actual course and try to understand it and figure out how it worked. 

And so, for me, it really became, as you talked about, being overwhelmed in the beginning. Really just having to focus on one thing at a time because the overwhelm was going to be so incredible.

And I was getting overwhelmed with, for example, trying to learn Keynote. And so, I would spend, sometimes, months just trying to really master each app and thing I needed to create my course until I became proficient enough to then put all the pieces together and then, start focusing on the content.

And that’s kind of how it went for me. 


How did you actually start launching this? Because you took all of this time to create this product that you hope people would buy, right? What was your strategy like in marketing it? 


So I bought David Siteman Garland’s course on how to create awesome online courses and it kind of took me through, like, a rough draft of how to market it once it was created. So, I kind of started with that rough draft which was a slow process that wasn’t really working. Like I was reaching out to his YouTube channel subscribers ‘cause I didn’t really have an email list yet. 

And then, David brought in on his bonus section of this course some of his clients who are using different strategies for marketing. And one guy really just seemed like the path I should take which was using Facebook ads and a lead magnet.

And so, I created my lead magnet and I just started marketing my lead magnet and it went viral. I was getting a hundred new leads a day and that lasted, like, nine months. I generated close to 5,000 emails in a 9-month period. 

And then, once I had those leads and I had my course created I just started marketing it to my email list through a 3-part video series leading up to the actual pitch. All just steps I followed through David’s course and it worked to an extent. 

I guess the only satisfaction I had from it was that I made my money back on what I paid David to learn all this information. But it definitely wasn’t like the $23,000 payday that I thought I was going to have.


Yeah. It takes a lot of effort and also money to do all of that until you learn it. But now you have all the skills to really market new courses that you’re going to make or will make, right? 




And also make sure you all check out the extended interview because I’m going to be picking his brains more about how he created those lead magnets, Facebook ads, and how to create a successful course. Were going to be digging deeper into that with you. 




Now, let’s go back to when you didn’t have your ideas yet and you, still, were confused like most of us before we got into this lifestyle, right? What were you doing before actually? I love learning people’s day jobs before they get into this lifestyle ‘cause it’s always interesting. 


I was actually living in Nicaragua and I’ve been running surf tours in Nicaragua for quite a few years. And the times were changing. All the people I loved had left the business that we had created together and it was just time for a lifestyle change.

And, simultaneously, my mother had gotten sick and so it was time for me to come back to California. So, through 2014, I was just kind of, like, cruising around California. 

And then, I was desperate to get back on the road. So, sitting in California and having, like, an odd job just because I had to be in California to be with my mom. and I was like, “I need to get back out there. What am I going to do?” 

So that’s when I found Pat – I started Googling. I didn’t ask for wanting to go back to Nicaragua and I was desperate to get back on the road and then found Pat and I moved straight to Thailand which is kind of Mecca for all the digital nomads. Yearly, everyone kind of migrates there.

And I just started trying to, like, network and meet people and absorb all of the knowledge that they had on how to become a digital nomad. 


A lot of people really want to get to the point where you are. And we look at all these articles about how to become a digital nomad, how to find work online. But can you tell us what the reality actually is when you are in this type of lifestyle? What is it like living as a digital nomad? What has your experience been in: the good, the bad, and the ugly?


There are two parts of the question: to get started and then the reality. 

Getting started, you can teach English online. That’s I think fairly easy for most Americans or Western English-speaking people. So, getting into it could be an easy first step. 

If you don’t want to do that and you have a skill set that you can mark it as a freelancer, for example, like you understand SEO or website design – something like that. That’s another barrier to enter, that’s easy for someone who has that skill set. 

If you’re like me and you don’t have any of those skills then, English is going to be the obvious option.

The reality of being on the road is that all the photos you see of people with their laptops on a beach under a palm tree writing like, “This is my office for the day,” is bullshit. Like most of it is sitting in a hotel room, whether you have a desk or not, trying to get shit done and try to make it work.

And it’s not as glamorous in the sense of, like, your work environment as people portray it. However, you make your own schedule and if you only want to work 4 hours a day, you’re usually in a tropical place, you do have an affordable bungalow on the beach that you can walk out and go enjoy the sun and the surf or go for a hike.

So, I think, that is more of a realistic picture of, like, you’re grinding like a normal person: you’re in a hotel room or work environment or co-working space trying to hustle. But you’re in a super cool place with really interesting people and you get to have some really great adventures along the way.


I think, for most of us who really stick it out in this lifestyle, it’s about the freedom, right? Because, like you said, it’s all BS that we’re working by the ocean. Honestly, it would be horrible to do that because first of all, you don’t want to get sand on everything. And it can get really hot when you’re underneath that sun and you’re working – that’s not very comfortable.

And I like to make fun of myself a lot because whenever I have to travel for work, I take those photos and be like, “This is actually not reality, guys. This is just for you to want this lifestyle but everything else is just us grinding on our desk or somewhere.” That’s not as fabulous like you just said and honestly, I like to make fun of that a lot. So it’s pretty cool. 




It seems like you’ve started a few companies and few businesses and you’ve been really a nomad for a long time. When you are doing all of these different things that you’ve done with your life, what has been the biggest setback that you’ve encountered that really kind of pushed you down and how did you get over it? 


I was in Nicaragua, we didn’t have the internet. I’ve never had any interest in computer games or anything like that. Using a computer was just needed to communicate with family when I was on the road. So my internet use was like once every few months, just going to an internet cafe and letting my family know I was still alive. 

So when it became time, and I knew for a fact that this is what I wanted to do. I definitely wanted to create something online, generate passive income, at least generate something that created a location to pin a business for myself. 

I had to go to square one. I bought a laptop, I sat watching YouTube videos and how to use my laptop. I sat for years on YouTube trying to just learn everything I need you to. And it’s still like that to this day, I mean, every step of the way, every new thing that I need to implement or incorporate into you know, the system that I have.

It’s a giant learning process for me that I struggle with. Kind of frustrating ‘cause I look at everybody else like all these Millennials have it good because they kind of grew up with it. I was right at the tail-end where it’s like the technology wasn’t quite there yet and I didn’t have any interest in it, to begin with. 

So I really feel I started from square one, ground zero. And if created over the last 5 years at least a high school education with how to use technology and how it all fits together within this online digital nomad space. 


But I love the fact that you are so determined and also really resilient that even though it took you how many years, you still went with it. You are definitely a learner and you also implemented it because I think for a lot of people it really gets you down, right? Especially when it’s something that you’re not good at and it’s hard to do that. 

It’s hard to go into something that you don’t know a lot about. And then, you keep going and it’s hard to motivate yourself a lot of times when that happens.


Absolutely. And I think like you, Debbie, the freedom and the allure of the realities is a driver and keeps us focused and motivated. Through those hard times, you weigh the options like, “What am I going to do? Go back and get a nine-to-five?” 

At this point, I’m a 40-year-old man, I’ve never had a nine-to-five aside from little side jobs to make ends meet when I need the money. Like it’s just for me, at this point, not a reality and I have to make it work. It’s just there’s no other option at this point. 

So you stick with it, you grind and figure it out and you have a lot of down years. And then, the skills that I’ve developed I think you know my day will come. And I just keep grinding and hoping.


Definitely, the alternative of going back to a nine-to-five is a lot worse than what you’re currently facing. So for the most part, that’s usually what we think about if we’re faced with all of these obstacles, so I definitely get that.




Now, we all have that “what now ?” moment and I’m sure you’ve had it too. Whether it was throughout the years when you were trying to build this business and then realize, “Oh my gosh, have I gone in over my head.” 

What was yours like and how did that go?


I have a lot of “what now? moments every single day. And I deal with it by standing up and I walk circles around my kitchen or go wash the dishes hoping for another light bulb moment, another sort of idea to come into my head that I can implement. 

And so yeah, like I said on a daily basis, it’s really like, “What do I do now?” Like I don’t have another question I can ask Google to help me get through this process that I don’t understand. 

And then, on a bigger scale, it’s like, “What now?” I’ve done this for five years. I just spoke about this on my own podcast and it has really worked in the way I thought it would. It generates passive income. It’s not $500 a month, but it’s still a little bit which doesn’t sustain my life on the road at more or less just pays for itself. 

So what now? We just talked about perseverance which is important, but it’s also really important that you know when to fold your hand and take that thing that you have created, put it to bed, put it to rest, maybe kill it altogether. Pivot, change, and start something new. 

So my “what now?” moment currently is trimming all the fat off this little enterprise I built online which is a surf instruction, surf regression technique which is an online surf instruction for surfers. And automating that so it’s like I literally don’t do anything anymore and just let it kind of pay for itself and be helpful to all individuals who want to utilize it and start building something new.

Because, yeah, at this point I have the knowledge of creating courses. I have knowledge of marketing, I have knowledge of SEO, I have knowledge of building websites. And now, it’s time to pivot and transition and just start anew.

So 2020 is going to be a year of maybe starting 1 or 2 new businesses online, trying to generate a few streams of income. And then, just try to maintain life on the road. 


So, where do you see yourself in the next 5 years? Because, like you said, you built up this business, maybe you want to pivot.


5 years… I see it fully automated. I see multiple flows of income, multiple cash flows coming in from various enterprises I’ve built or online businesses and being, I must say, a real or legit digital nomad. 

I mean, these peer groups who I consider, like, real digital nomads who’ve built very successful businesses and really don’t ever have to do the side work that I have to do to maintain my lifestyle. Like that’s where I will be in 5 years. I will be like them, one of them, one of their peers who has created something more sustainable. 


I think having a mentor and people around you that understand the hustle and the struggle is so crucial to making this work because it can also get really lonely. And it’s not like a day job where you have co-workers or a boss that’s constantly nagging you to do things or even supporting you.

That’s why I think having these people around you is really crucial. 


Yeah. And that’s a good point that I like to touch upon because I was like, again, living this fishing village in Nicaragua, trying to be a digital nomad or at least build my first business and there weren’t any like-minded people around me. I mean, there are tons of entrepreneurs ‘cause you have to be entrepreneurial living out of your own country, sustaining yourself. 

But I didn’t have anybody to talk to about how to use ScreenFlow and what I should do next. Then, I found this group called The Dynamite Circle, which is like an international Mastermind and that has been just a game-changer. It’s just meeting these people and hearing their stories and networking with them and utilizing some of their services that they provide. 

I mean, that’s where I think I really found my tribe, found my group of people that I’m going to stick with and be a partner for a long time to come.


Absolutely. And also, I think when you have a podcast like this where we’re interviewing people who are doing something that we want to do and we get inspired by their story and their journey is also a really great way to create that community as well. 

That’s why I love podcasting because I get to meet people like you and it’s pretty interesting when you have that type of dynamic as well. 


Absolutely. Yeah. I mean, I was just in Bangkok recently and it kind of like “what next? what now?” moment and just praying that I had an epiphany and it did come. Day five of multiple seminars and just networking people talking about their sales funnels and email sequences. I  was like, light bulb moment, “I get it. Now I know what to do.”

And then, I went to Chiang Mai and I implemented it and it totally didn’t work but it was still I think the light bulb moment I was looking for and just, yeah, it was great. I wouldn’t have had it, is the point, if I hadn’t been with a network of people. 


I think it’s also just doing something, right? Just a test that somebody pushes you to do because even if it doesn’t work, at least it got you off your butt to do something productive for a little while and you don’t feel so bad about yourself. And that usually gets you going for the next few weeks or even a few days which is really helpful. 


It’s so true. I mean, yeah, like we talked about earlier being in that hotel room by yourself not knowing what to ask Google next and just in front of a wall not knowing how to get around it. 

Yeah, it’s easy to kind of lose productivity and get down on yourself. So having that network around you kind of cheering you on, rallying for you like, “You can do this. Think about it like this.” It makes such a difference.


So, let’s talk a little bit more about mental health because I don’t think that’s touched up on enough in our industry. What would you say is the one thing that has really been a setback for you in that sense and how do you usually deal with it?


I think, for me, like I fell in love with the road a long time ago. And so the road itself for me is just a warm blanket. I can wrap myself in if I have a negative thought, if I feel myself getting depressed like, “Oh, I’m not smart enough to do this. I don’t know if I’ll ever achieve this ‘cause I’m not good at technology.”

There’s always a local pub that has some interesting people to go chat with that just brings me so much peace and joy. ‘Cause I’m on the road and my podcast is basically similar to yours, which is interviewing interesting ex-pats and people around the world doing unique things and making a living doing it. 

So, I always have that to fall back on so I never find myself depressed, I guess, or feeling like something is unaccomplishable. I only feel that way when I come back to the States and I’m just like, “What am I doing? I’m back here again.” ‘Cause I have an opportunity to always make money back with States being American and fairly easy to make a little bit of side cash in America. 

So, when I do come through and I see the family night, spend a month or two making a little bit of money to get myself through the next few months. It’s tremendously depressing and I don’t have that sort of local bar that I can go talk to an ex-pat at.


So, coming back to the U.S. is your version of being in a nine-to-five in that sense. 


Exactly. I mean, just being in America is like being in a nine-to-five. And I don’t mean to sound negative towards America. It’s my home country and there are so many beautiful things about it and beautiful people who live here.

I mean, like I said, it’s one of the easiest places to make money if you apply yourself, but it’s just not a place I ever fit in and feel like I want to be here.


I’m sure that feeling is shared by a lot of people especially the ones that want to leave their nine-to-five right now and go off on the road just like you.

So, talking about creating income here in the United States, how much did you save before you set off to do your long-term travel and how were you able to budget it 2to last? 


So, I’ve always had a rule of having at least $2,000 in savings when I landed a new place, $2000 or $3,000 is kind of my comfort zone. And then budgeting wise, most places I prefer to travel are third world countries. Street food is generally very cheap. Accommodations, I can usually keep between a $5 and $10 a night. And I’m a walker, I like taking local transportation. 

So it’s like, if I’m moving from one country to another, I’m usually not flying. I’m usually overlanding it and taking long bus rides or hitchhiking. I like to move very slowly and keep my budget. Nowadays my budget is at $20 a day, back when I was going really hard at this lifestyle stuff it was the $10 a day range which was super hard to do and I think really not that sustainable for a digital nomad who’s trying to build something that’s more for like a traveler.

But as a digital nomad, if I keep my budget around twenty bucks – I’m as good as gold. Like I’m eating well, I’m having a few beers at night, I have a comfortable private room sometimes with a private bath.


That reminds me of a book that Nomadic Matt wrote about living off of $50 a day and you’re doing it at $25 a day. So, you definitely have some good secrets for that, huh? 


It’s not a secret. I mean, I don’t do anything that I really don’t want to do. I think for a lot of people who are traveling, maybe they want to do a lot of terroristic things, see things, museums for example, or go on paid,  guided tours. 

My enjoyment is just like sitting and absorbing the culture and, like, watching go by. And I don’t really do like elephant tours in Chiang Mai. It’s just not where my head’s at, not enjoyable to me.

And so, I save a lot of money doing it like that.


And I think, on a long-term travel, you also have that luxury to take your time to sit around and really absorb the culture, like you said, if you only have five days.

I don’t know. For me, I definitely don’t do that anymore. In my early twenties I was like, “Oh my God, I got to see everything!” Everything has to be so fast. I got to take off as many countries and now I’m like, “I don’t even know how many countries I’ve been in. Honestly, I don’t really care. I want to know more about the country than how many I’m going to go to.”

So, I think it’s all so different as time passes and your priorities become different.


Yeah. I agree. And that’s a normal sort of growth and evolution in us as humans. Things are going to change and that’s okay. 


Now, let’s fast-forward to 40 years from now, Chapin, and you’re looking back at your life. What legacy would you like to leave and what do you want to be remembered for?


I don’t. I get this a lot. I don’t have any desire to leave a legacy or be remembered for anything in particular. I think a byproduct of what I am doing with my podcast since I’m recording myself and I can keep my listeners in the loop with, like, the evolution of my business in my life and my lifestyle both personally and professionally.

That will be a legacy that I leave but it’s not something that is motivating to me or drives me anyway. You hear a lot of these gurus talking about the legacy. Like Pat Flynn talks about it and Chris Ducker and it’s like, “That’s not me, man. I don’t care.” 


Well, it doesn’t have to be on a big scale. It could just be for people that really know and love you, like what would they remember you as.


A good friend’s uncle once said something else really profound and he was talking about dating and the females that you have in your life that may be just don’t work out. He said if you imagine all the females that you dated and didn’t work are sitting at a table together, you always want their conversation to be positive about you.

And I think the if you talk about legacy and you talk about how I want to be perceived after I’m dead, I want everyone sitting at the table who knew me personally, love me says only positive things about me and I only ever meant to do positive, loving things to the individuals that are sitting at a table and the world in general. 


You see? So, that’s a good one? 

So, what are you currently working on that is really exciting to you?


I’m currently, like, pitching my podcast out to figure enterprises. Maybe taking it inhouse somewhere is a thought I’ve had which I think sounds interesting to get a little bit more financial support, allowing me a little bit more freedom to kinda stay in one place longer.

And really I think interviewing all the people that I want to interview ‘cause a lot of these little backwater towns have some fascinating ex-pats that I’d love to spend more time with. I’m also developing a few new ideas to, like, put out there online, like a supplement company. 

And just things that I’m really passionate about. Within this industry a lot of people are talking about, “You got to test the market. You gotta do what the market wants. Just building brands because you want to build them isn’t the right way to do it.”

And there’s so much truth to that but at the same time for me as an entrepreneur, I can’t get behind anything I don’t believe in. So I’m taking the approach of finding the things that I know I can at least focus on, build, and follow through on to deliver to the market. Rather than trying to just like be fine with what the market wants.

So, the supplement company I’m really passionate about, that’ll be all online, all automated – probably do it through an affiliate by Amazon. And then, I might be going, instead of digitized service-based businesses, to more product-based services, physical product paid services.


Now, if our listeners want to know more about you, where can they find you?

Chapin:, that’s my podcast and place of which you can hear about me. I give you, like every 10 episodes, an update on myself. I mean if you happen to have an audience member who is a surfer and wants some online surf coaching, you can please reach out at, I’m more than happy to help you with whatever questions you may have.

And If you want me to make you a little video analysis of your surfing. Kind of like: imagine the golf swing, people film themselves swing golf clubs. A lot of my clients film themselves surfing. Send me the footage and I create little instructional videos for him. 


That is a really cool idea.

Thank you so much for being here today. I really appreciate you sharing your incredible journey with us.


Debbie, thank you for having me. It’s been a pleasure.

Listen to Chapin’s extended interview where he shares how to create a successful online course.

What you’ll find:

In this episode, Chapin talks about his secret sauce on creating online courses and what makes them successful.






Show Credits:

Audio Engineer: Ben Smith

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