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Ep: 181: How this former pro cyclist became a remote business strategist with Derek Loudermilk

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In this episode, I speak with Derek who is a former cyclist turned professional author and lifestyle entrepreneur. 

Derek is known as a unique business strategist who helps unconventional entrepreneurs and thought leaders grow their business. 

Listen on to find out how Derek leads entrepreneurs and thought leaders in transformative adventure experiences around the world.

Listen Below:


Ep: 180: How this digital nomad travels the world with her family as a remote social media marketer with Julia Jerg

Ep: 179: How this mother of two decided to donate all her belongings and travel over 40 with Nubia Younge

Ep: 178: How this former Hollywood Television Executive found balance as a remote life and health coach with Jackie de Crinis



Hey everyone! Thank you so much for joining us. I’m really excited to be with my guest today. I’m here with Derek. 

Hey, Derek, how are you?


Debbie! I’m doing great. How are you?


I am wonderful. Well, with our circumstances and even through the circumstance, but can you tell us a little bit about you and why you live an offbeat life? 


Well, I’ve always, as a kid, wanted to build adventure into my life. I grew up being a Boy Scout and just spending a lot of time in the woods. And I tried to design a career a couple of times around adventure and this is actually the third time I’ve tried.

First, I was going to be a pro bike racer and travel the world racing bikes. It turned out that it’s actually really hard to make it as a pro athlete and I didn’t have quite the same natural genetic gifts as a lot of these Olympians and all these phenomenal athletes.

So then, I tried again in academics. I decided to work in Yellowstone National Park as a microbiologist. I was just trying to discover a new species living in the hot springs up there in the boiling acid hot springs – extremophiles. 

And that actually was really fun when I was in the field doing fieldwork. But most of the time, which I didn’t realize, I was spending in a dark room in front of a computer or in front of an electron microscope. So I wasn’t outside very much. 

So it wasn’t actually as adventurous as I hoped so I pivoted again. I said, “Okay. I really want to double down on being outside and adventurous.” But I also learned from grad school that I loved teaching. 

So I wanted to build teaching and about the time I read the 4-Hour Work Week about seven or eight years ago. And so I just started piecing together these little bits, stealing what was working from other people, stealing from Tim Ferriss and Lewis Howes. 

Slowly piece together this adventurous life that I’ve been doing for the last six or seven years.


Can you tell us a little bit more about what you’re currently doing to keep your life more adventurous?


Yeah. Especially, given there’s a couple of constraints that I’ve experienced recently, one, I have two young kids. So I went from being single and moving fast and just sort of exploring the world quickly to now, I have a wife and kids and also a house. And now we’re quarantined because of this virus. 

So there are all these sorts of physical constraints. 

So, my adventures have shifted a little bit to more, “What can I explore in my own mind? What can I explore during dream time?” They really getting into lucid dreaming and other non-ordinary states of consciousness through breathwork or plant medicines and really doubling down on the mental adventure which doesn’t require any physical travel. 


Well, that’s really what we need right now especially with everything that’s happening and we can’t really leave our house unless it’s for necessity. So this is really insane for somebody who’s so used to being on the road even with your family. What kind of toll has been taken on you mentally, specifically?


When you get used to something and you just have your patterns of life, I was used to living out of a carry-on bag for many years. We bought a house in November to kind of settle down. We were living in Portugal, we’re going to move to Romania.

Our pattern had been moving slowly every 3 months from one country to another. And my wife said, “I’m just kind of sick of this and I would like to establish more roots.” And there’s a balance. 

Now that I’m a parent I’m thinking like, “Okay, there’s an advantage to kids seeing the world exploring the world, and experiencing different cultures. And there’s a huge advantage to consistent, stable relationships growing up.” 

So you feel this safety and support in having your friends and that’s what I experienced growing up. My elementary school friends are still some of my closest friends 30 years later. So I wanted to give in that opportunity. 

So it seemed like the right time for us to kind of pick home base which is in St. Louis, the same city where I grew up. And so, just kind of, you redefine your routines – what is the new normal? This really tickled me: two years in a row, all of a sudden, we’re doing the same activities. Like, the same festival, the same trick or treating on the same street.

It’s really interesting to see life in the cycles of the seasons and in the patterns of a place from one spot versus trying to see the whole world and just, like, getting these bits and pieces even if you stay for a few months.

I’m kind of like just observing the difference between these two things still and everyone right now is slowing down, we’re caught in their houses. So everyone is being a little bit more still and there’s more space for reflection, for understanding where we’ve come from and in who we are right now in our lives.


What about as a parent? Because a lot of my friends are teachers. I used to be a teacher and I used to be a therapist for kids and my fiance, he is also a therapist right now and so many parents are going crazy, especially when you have multiple children like you do, Derek. 

How do you keep sane and how do you keep everything balanced? Because you still have to make sure that obviously, you’re taking care of them, you’re taking care of your business. How is that going for you? 


It’s kind of like a relay, I guess. I wake up with the kids then, while I’m feeding them breakfast and sort of getting them ready for their day, I’m also planning my day. So a couple of hours in, I hand off the kids,  hand off the baton so to speak. Boom, go to work, do little short bursts of working out 2 and 3 hours at a time.

My workdays tend to be, let’s say, three 3-hour bursts but they’re kind of split up, right? So, we’re relaying back and forth. So once my wife starts to get too frustrated with the kids, maybe that’s a great time for me to stop, work for a little bit, and focus for a few hours. 

So we sort of bounce the kids back and forth, both cooped up in the house. And yeah, it really is about trying to manage the sanity of everybody in the household. It’s no different if you’re living with a group of adults, you would be doing the same thing. But kids, obviously, don’t know how to keep a house neat, right? 

So you’re adding layers of destruction a group of adults wouldn’t have. 


Oh, it’s true, you definitely have to be strategic with your new routine. And having your kids with you and being in an enclosed space for this long of a time in god-knows-how-long. 

But it’s also really interesting. And I was talking to somebody about this before, even a few weeks ago, a few months ago, obviously, all of our lives were all about being on the phone. Even when we’re with our family and friends, we’re constantly on our phones, on our computer and we were just unconnected in a lot of ways.

But now that this has happened, we are trying to get more connected face-to-face. We want to be able to hold each other, to talk to each other in person, to shake a stranger’s hand even. Things that we really took for granted are something that we’re hoping to have. 


Yes. I mean, what’s reminding me is that paved paradise, put up a parking lot. Like, you don’t know what you got ‘till it’s gone.


Yes, I love that song.


Yeah. It’s like removing something and then you can appreciate it. And then, well get it back and it’ll be great. 


I think that’s really what I’m trying to appreciate at this time, at this moment right now. Because it all seems really bleak, especially if you talk to people and you watch the news -I try not to do that as much as possible otherwise, we’re just going to be, like, under the table, panicking under the blankets just like rocking ourselves back and forth. 


Yeah. I was just really curious just like everybody to track sort of what is developing but eventually, I stopped reading the news. And now, I just have other people tell me what’s going on because it’s the same as the news ever.

I mean, they’re going to get more clicks and more reads the more fear they can trigger. So, it’s going to shape your thinking, probably, if you follow the news a lot. Depends on where you’re placing your attention. If you’re following the news and you probably feel a lot more worried but if you’re thinking about where the opportunity here, for me personally, for humanity, or for my business. 

People become millionaires and billionaires in times of crisis because people that find solutions quickly get out there and help people. So it kind of depends on where you’re placing your focus during this time. It’s going to dictate how you feel.


Yeah, I think that’s really true. And also the fact that there’s so much time for us right now. Well, unless you have like a ton of family at home and you can’t concentrate but otherwise, hopefully, there’s more time for us to really reflect. And also more time for us to start, maybe, thinking about other ways to create income with our business or side hustles –  things like that.

Now, talking about that, Derek, how are you able to create an income as a digital nomad and remote worker? 


Yeah. So probably the biggest portion of my business is the business coaching that I do. I help thought leaders in a variety of different spaces: authors, coaches, speakers, online course creators, maybe retreat hosts. And we often create a unique business model to know how different pieces of their interests, different pieces of their skill sets can fit together to create a business.

Business coaching for these types of people is probably half of my income. And then, I write books. I never expected to be an author but I’ve written, I think, five books in the last 4 years. That kind of happened accidentally. So I read a lot of books and have my own online courses.

For a while, I was hosting some adventure trips. I haven’t posted one in a little while. We are canceling our upcoming one because of the virus. I don’t want to try to market travel right which I think would be a pain. 

So, yeah. And I’m always looking for new opportunities and I guess we can talk about affiliate tales as well. I have a lot of creative clients,  friends, and peers that have amazing programs. So I don’t have to create those.

I often help sell and promote other people’s work as well. So that’s part of it. 


I love that fact about affiliates because people do the work and then you get money as long as you market it well. So, as long as you’re a good marketer, it’s good to go. 


Yeah. And sometimes you’ll be like, “I really want to create a course about…,” ‘cause you really like it, you know something about it. But if somebody already has a really good course then, you have to decide, “Okay, do I want to create a course on the same topic or do I want a coach on the same topic as somebody else? Or are they doing it better or as good as I can do it?”

Because so many people have these great programs and courses, it also forces you to double down on what’s unique about you, how you teach with what you know, and your own unique position in the market. 

So, I think that’s really helpful and you can decide whether you actually need to create something and sell it on your own or if you want to tell somebody else that is already done. 


Now going back to when you first started your business as a coach, how did you get from being a pro cyclist and microbiologist? ‘Cause those two are very different already and now to a business coach. How did that turn into this current business right now?


Yeah. So when I read The 4-Hour Work Week, I was super excited to start a business that I could take anywhere – portable business. 

And I reasoned that places like Vietnam, which was the first place I went, the estimated cost of living is about $1,000 a month. So I said, “If I can earn $1,000 a month with a remote business then, I basically have an infinite runway to build a brand, to learn the business. 

And so I started coaching racing cyclists. I had 4 clients, $250 a month – there are your thousand bucks. And I was doing remote calls once a week with these athletes. Young athletes who wanted to eventually become pro cyclists. So, just teaching based on my experience.

And that’s kind of how I have approached coaching all along. I see a demand or there’s a request. people keep asking me about something. I started my podcast, The Art of Adventure, 5 years ago and I think you did a few podcasting mentorships or something like that.

People were asking me, “How do you start a podcast?” So what I was doing was a lot of times we would meet in the living room of my villa and we would do these podcast launch boot camps where like five or six people get together every week for six weeks and we all launch podcasts.

And we practice interviewing each other, we help each other design the cover art, use our network to find guests, and all these things. So it was really fun. And so whenever I needed money, I would run one of these boot camps and I think we’re charging 500 bucks for the whole program. 

So for 6 people, I would make $3,000 and do that a few times a year. And again, this is just kind of breaking even. Low cost of living in places in the world. Like, I was living in Bali at the time, I wasn’t banking a lot of money. I wasn’t spending a lot of money. So I don’t recall coconut cash now.

But you don’t have to earn a ton in order to be able just to sustain your lifestyle which is why so many, I think, digital nomads go to these low-cost places.


I love the fact that one of the things that you said which are so important is finding what people need and want and starting a business from that. So that’s really one of the easiest ways to do this, right? 

I think a lot of times people make this so much more complicated than it is. So you don’t need to reinvent anything. Sometimes it’s just asking people what they want or listening to what their pain points are and then creating a business from that. 


Yeah, definitely. And once you’ve done this a couple of times, you can kind of go about it two ways. Like, you can start a business based around a problem that you’re currently solving for yourself and just solve it for everybody else at the same time. 

So, friends have started, like, they’re trying to keep track of their annual goals. So they create an app that does it for them all of a sudden that’s just available as a tool solution for everybody. 

Then the other way that I often go about it is what I have already figured out in my life. I figured out how to write a book, publish it. I figured out how to start a podcast, figured out how to run a remote business.

So I can just teach from experience and then as I’m continuing to develop the business, I can sort of share, “Here’s what I’m doing right now. Here’s what’s working in marketing. Here’s what working in building a network – all these things.” 

And so, a lot of my clients, I’m just sharing up-to-date stuff, “Here’s what we’re doing now. Here’s what we’re seeing. Here’s what working and not working.”


Currently, what is the biggest setback that you’re encountering as an entrepreneur? Because someone may look at you, Derek, and say, “Well, he’s doing really well. He’s traveling the world now. He has a base. He has a beautiful family. Everything must be going so well.”

Little did they know that there are still issues and problems. It’s just different in different parts of your business and different times in your business.


Yeah, I think that’s a great question. 

What I’m working on right now is learning Facebook ads. I’ve built this entire business and I think a lot of people, because there’s such leverage in social media and online marketing, they double down on that skill set right away.

And I’ve grown my business pretty much entirely based on personal relationships. So, just going and building relationships with ideal customers and clients or podcast guests – whoever. And so just looking and saying, “Here are the skills that I think I need to develop for the long term, for this career.” 

Having a solid sense of Facebook ads or Instagram ads will really help. Even if I don’t end up hiring an agency to run these ads for me eventually, I want to know the inner workings of it so that I can speak knowledgeably about it. 

So right now, yeah, I’m actually running my first Facebook ads campaign. Basically, I’m giving away copies of my book and then people sign up and I’m growing my list in that way.


I’m also on the same boat. I’m trying to figure out Facebook ads as well. I think it’s definitely a different sort of ball game.

And I agree,I also feel like we have to learn it before we hand it off because for me it’s so important to understand what they’re doing just in case anything happens.  And also to understand what’s going on. I think that’s so important to do with your own business. 


Yeah. It’s very fun and enjoyable just to think about this line of marketing and how people engage. Because I’ve clicked on ads on my Facebook and it has led me to eventually buying something. 

I watched a video, I read about something, I get to know a new person – all of a sudden their ads came up. And I never met them before but all of a sudden now, there’s a real person behind it, a real business behind it. 

Now, being on the other side and how I want to build a relationship with people that I never met before through these ads is kind of a fun way to think about it.


And to figure out their strategies, how they get people to click on their ads is also really fun. I think it’s anything that we learn from. I think a lot of times, as entrepreneurs, we’re always trying to problem-solve something. 

So the more you learn, the more you know, and the more money you make.


Yeah. And one of the things I’m experiencing right now is that there are some best practices in marketing but really marketing is an experiment – let’s see what works. So there’s a huge space for playfulness there. 

Like, here’s an idea that we have, let’s try it and if it gains traction or people are into it, if you’re doing a challenge or if you write a funny headline or whatever it might be, there’s just a lot of joyful playing that can happen in marketing. 

What was that show? Mad Men? In that show, he’s like, “Imagine there’s a guy. His driving this car and looks down at his watch.” He’s like painting the picture but he’s just kind of making it up, it’s just a story that he’s making up. Everyone’s like, “I love it. It’s amazing.” 

Getting to experience that is really fun.


And seeing it come to life and then understanding if people are drawn to it or maybe you have to pivot and change strategy. So it is. It’s really interesting to figure these things out. 

Now, Derek, let’s fast forward to 30 to 40 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 


40 years from now. Well, what I expect is kind of a different planet. 

I love my own entrepreneurship and I love helping other entrepreneurs but ultimately, I think, humanity uniting and, sort of, instead of all this separation we feel, whether it’s wars or politics or us versus them – just tribalism, I really like to have my work and the businesses of people that I’m coaching help people come together as a species. 

I think this pandemic right now is really going to help see that we’re all one so to speak. We’re all interconnected, we’re all part of this same broader human experience. 

And ultimately, I’d like to be remembered for assisting in that process to move from sort of an egocentric based way of doing business or living life to how can we serve others, how can we experience joy and gratitude and everybody get to daily experience their bliss, their joy. 

And that’s kind of what I see in what I’m trying to create in my own experience right now for my family, for my clients. And I think, as entrepreneurs, we have this great position where we can have a business that will fund our purpose and our mission at an end. That’s the way I see a lot of it.

I talked to a lot of entrepreneurs and they say, “I just need enough money. I’m not in this for the money.” So money really then just becomes a tool and if you grow your business all of a sudden you can do more of the things that you really care about. 

That’s what I love. It’s just helping people with the tools to sort of really take their experience of being human to the next level. 


Yeah. But also another way to think about that, I think I hear this a lot from people especially creatives is that yes, you are not doing it technically for the money but in order for you to make a larger impact in the world, you have to create money.

And it’s not evil. It’s what you do with it that would be evil. But the more you make, the more people you can actually help, and the more you can be able to change the world in that sense. 

So whether you want to feed more people in the world or whether you want to create more jobs so that people can feed their families and create more impacts, I think it’s also something to think about.


My friend and mentor said money is doubly useful. It’s useful first as an indicator that you’re on the right track. So if you’re doing something valuable, you’re often rewarded financially. So, if your business isn’t really serving what people actually need, it’s not gonna be successful. The more successful the business is in actually helping people, you’re going to generate money. 

And then all a sudden you have the money to help people. So it’s, like, valuable two times.


Yeah. Absolutely. And I love what he said. It definitely makes sense ‘cause he’s right.

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


Well, there’s a project that I am really sad about which is on pause right now because it involves a large group of people. A friend of mine was talking about If you want to make a contribution in the city.

I live in St. Louis which has a lot of violent crime. There’s a lot of gun violence here and it always bothered me and I always wished I could do something about it. But I was not really excited about trying to volunteer for some organization. 

So it got me thinking like, “How can I align my interests with solving this problem?” And for the last couple of years, I’ve been really exploring a lot of physics and metaphysics and how our thoughts create physical reality. 

There’s a bunch of science that shows exactly how our thoughts create a reality which is super cool, it’s amazing. I didn’t even realize it before. 

Maybe this is going to happen already, maybe we’re going to see a reduction in violence just because people are going outside. So maybe it’s already taken care of and I wouldn’t have to do this project. 

But the plan was to set up a giant, sort of group intention experiment to see if we could reduce violence simply by focusing on everybody’s intention. Like, church groups and locals. Like, all the people in St. Louis that care about reducing violence all at the same point in time. 

If we have the same intention for reducing gun violence in our city, there’s actually a bunch of experiments that they’ve done in prisons and other cities around the world. This has been shown to be effective. 

And so I wanted to bring that to my city of St. Louis with a special little twist. We’re going to try to set the world record for the world’s largest crystal grid. And basically use the grid as an amplification mechanism. 

So this is just a big experiment that I was setting up and going to try here in my city. So definitely I think we’ll do something like that once the quarantine gets lifted. 


I can’t wait to see that and definitely keep us posted with that event and that information as well.

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


You can find everything that I do on and my podcast is The Art of Adventure. 


Perfect. Thank you so much for being here and for sharing your incredible story with us. 


Debbie, thanks for having me.

Listen to Derek’s extended interview where he shares The quantum leap to have more impact and how to push your limits to run a successful business.

What you’ll find:

In this episode, Derek guides you on how to make that quantum leap and push your limits to run your business and reach your goals.

Follow Derek:

Show Credits:

Audio Engineer: Ben Smith

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