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Episode 105 – Chris Guillebeau: The School Of Side Hustle

Have you met someone who never tried working in a corporate world and is now a successful entrepreneur? Who believe it is much a safer choice to bet on yourself rather than to bet on someone else’ business? Our today’s podcast guest will tell you just that. He has been working for himself since he’s 19 years old, and even though at the beginning that is mostly because of his personality, we can take so much value as to why we should not hesitate to work for ourselves.

A lot of you might be able to connect to his life story. The young Chris was a juvenile delinquent and a high school dropout. At a young age he started selling anything online to support himself. Life took a turn when he had the opportunity to live and serve overseas in West Africa and began travelling to other places. He learned a lot that he knew he just got to share it to the world, and that is how the New York Times bestselling author and modern-day explorer Chris came about.

If you wanted to unlock the entrepreneur in you, if you wanted to start a side hustle, and eventually start something for yourself to benefit you in the long run, you got to listen to this episode in full and be ready to digest all the wisdom Chris has in store for all of us.

Here’s What You Missed

● Chris’ early life and his turning point
● How to find opportunities using the internet
● Why you got to work for yourself and why has that become the mainstream nowadays
● Tips on how to be successful in podcast
● How to boost your self-reliance
● Chris’ tips on how to stay disciplined

Knowledge Nuggets

A big part of Chris’ message is about self-reliance. Believe in yourself that you can do things on your own and that you can figure things out along the path. Don’t look back and dwell on your mistakes but always look ahead and determine how to can take a better step. Indulge in the following chunks of wisdom shared by Chris in this episode.

[5:50] This pandemic taught us that we can’t control a lot of things we thought were under our control, but there are still a few aspects that we can. When Chris hit desperation, like what a lot of people are going through now, he started to look for opportunities online. He tried selling things in his apartment then he learned about buying and selling. This is a basic business everyone can do and should take a look at. It’s not like you’ll be doing this forever, but it’ll generate some income now, and will teach you new skills.

[8:20] Another thing this pandemic taught us is that there actually is not a lot of security on that day job. So entrepreneurship now is so much more accessible and mainstream. It’s the best time that you start betting on yourself.

[11:12] For those working for someone else’ company now, ask yourself “What can I do to at least replicate the income this company receives because of the work I do for them?”

[13:05} Ask yourself, “What can I create that will give value in the long-term?”. When you think about starting your own business, sometimes it is not always about your passion or about what’s hot right now. Often times, these are just passing. Eventually, it would be fun to be doing works that aligns with your passion, but if you want to build something that will benefit you in the long run, think about a problem and how you can provide a solution through a service, product or a community.

[15;38] People always feel they are late to starting some stuff. People tend to get discourage when starting blogging, social media marketing and podcasting, etc. because they feel they are already late in implementing these and that everybody else has been doing it. But there will always be ways how you can stand out.

[16:30] First step to monetize podcast and other mediums is to build an audience. How? When you put out content, always think about that it’s about your community. Think about what your community would like and do it. Build relationships. At the first part of your journey, always see to it that you are always available. Show up wherever you can. So when the times comes that you launch a podcast, you will have a little bit of a platform.

[19:16] Second step to grow your podcast is to care. Do everything you can to care for the people who pay attention to you. Try to be helpful and put something out that will be useful for them, even for free. If you really want to build a business, invest in relationships.

[23:37] Don’t think a lot about the past. Sure, you can look back to understand what went wrong, or why it did great. However, whether it’s a success or a failure, don’t live off of that. Always think about ‘what’s next?’ How can I keep improving?

[25:17] Always work just as hard, as if you’re the underdog. Always be hungry, always be motivated.

[27:17] Most of us find our path by going down different paths. Be self-reliant. You don’t need other people telling you what to do or when you can start, like you wait for a permission from them. It’s OK to make mistakes, you learn and become better.

[28:26] Two tips to become disciplined: 1. Do something you actually want to do, and 2. Build a habit. The longer you’ve been doing it, the easier it is to keep going than to break it.

[32:14] How to get out of debt? Earn more money. You can save money and be frugal, but that won’t get you out of debt. Create something for yourself, and look for opportunities. It may sound daunting, but you can find ways to start side hustles without quitting your day job.

[35:57] Just start to do something. Research, read, and find those topics that you connect with. If you really can’t take that first step, stop listening and researching, because sometimes research is a way to kind of put things off. Just start what you need to do and take that first small step.

Important Reads and Links

Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear

The Money Tree: A Story About Finding the Fortune in Your Own Backyard by Chris Guillebeau

Chris Guillebeau: https://chrisguillebeau.com/
Chris Guillebeau Facebook: https://www.facebook.com/chrisguillebeau/
Chris Guillebeau Instagram: https://www.instagram.com/193countries/
Chris Guillebeau Twitter: https://twitter.com/chrisguillebeau

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Download this episode’s transcript HERE



Click Here for a full transcript of this episode:


Casanova Brooks:

What’s up Dream Nation today on the line, we have an episode that I can tell you. I have not been as excited for many episodes as I am for this one. And the reason being is because now we got an opportunity. It’s, it’s almost like when you got a mentor from afar and somebody who inspired you to get in the game and who’s kept you in the game and now you get an opportunity to bring them onto your show.

It’s a lot of fun. So without further ado, Chris, you want to go ahead and say what’s up to Dream Nation

Chris Gillebeau:

Dream Nation what’s good. thank you so much for having me on the program, man. I’m excited. I’ve been looking forward to this as well. Thank you.

Casanova Brooks:

Yeah, man, this is going to be a really fun one. And I always like to make sure that I give the proper introduction.

So a lot of people are going to know who you are within a couple of minutes, but for those people who don’t know you, you obviously you have the School of Side Hustle podcast. You have wrote multiple books. you’ve been on the biggest of stages and you’ve helped so many entrepreneurs just like myself, at least have the confidence to go after their dreams.

But I want to take it back because I always. I like to think of entrepreneurs is just like superheroes. We’re constantly putting on capes and we’re flying around trying to solve other people’s problems and other situations. But before all of the publications, the books, the podcasts, everything else, if we can take it back to when you were just a young boy, tell me.

Chris Gillebeau:

Yeah. well, I’m glad you, I’m glad you set it up like that because I feel like sometimes we look at people that might be a little bit further down the road or something, and we’re like, Oh, it’s cool that they did that, but I can’t really connect with that. Or I can’t relate to that myself and such, which is why I think your story is so powerful and motivational.

And, that was just, I was just an amazing experience for me. And that kind of like set me on this foundation for a lot of stuff that came. So I was an aid worker there and started traveling as part of that, both within Africa and then elsewhere around the world as well. And then, at a certain point I started writing about some of this and I’d always worked for myself also because I wasn’t good at working for other people.

Basically. I kind of learned that early on too. And so, at a certain point, I was like, I need to write about some of this or at least share it in some fashion. And like, what’s the, what’s the best way to do this? Cause you know, nobody knows who I am. So I started a blog called The Art Of Non-Conformity.

Like block by block. it was very much just about sharing stories and then eventually connecting with people. And then, you know, a lot of stuff happened after that, but I think it kind of goes back to like where I was, I was dissatisfied. Wasn’t happy with what I was doing. Felt like there was something more out there, you know, et cetera.

So for me, it’s all like that, that discontent that led to everything that came later.


Casanova Brooks:

it. And what made you feel like, because if you’re a mission ships and you’re in South Africa, you’re providing so much value to the world, at least you should feel like it because you know that you see how blessed you are, you know, coming from the U S and then going over there and all these other.

So talk to me about what made you dissatisfied. How did you recognize that? Like, listen, I still have a problem.

Chris Gillebeau:

“I still have a problem”. I like that phrase. I think it was so I, I figured out kind of how to work for myself a little bit. I wasn’t doing like, you know, massive real estate deals like you, but I I’d found a way to like sell stuff online with eBay and other online auctions.

And, you know, basically found a way to sustain my lifestyle and not be in debt and not have to go work for The Man or whatever. That’s kind of how I thought about it when I was 20. And the discontent came from believing. Like there has to be more like, this is pretty cool that I can do this. Like, wow.

I feel so lucky. I feel like I have such such privilege in this. So what am I going to give? Like, you know, great power, great responsibility, that whole kind of thing. And this was, Like after 9/11, I was a little bit depressed, like so many people were and, at the time, and it was like, what can I do to give back?

And so I heard about this organization, you know, in West Africa and that’s how that came to be. And I appreciate you saying, like, you know, that was giving value. Like hopefully I was supporting the, the hospital work that they were doing there. But I think it’s always good to just point out that, like I was, I was receiving a lot of value as well.

You know, like for me, it was like, this is really opening my eyes to so many different things and giving me experiences that I will have, you know, with me for the rest of my life. So it’s been a long time since then, but I still, you know, the memory is very, very clear, so I’m really grateful that I did that.

So I’m really glad I was able to do that.

Casanova Brooks:

Yeah. And, and I appreciate you, you know, I guess showcasing that as well. Cause most people would be like, yeah, you know, I gave value, but I received a

Chris Gillebeau:

lot of value.

Casanova Brooks:

You said that you were already started making a little bit of money online and I think that’s so relevant to today’s world because there’s a lot of people that this is their post 9/11. They didn’t really understand the 9/11, but now they’re like, man, And they see the opportunity on the internet is there’s never going to be a bigger one than right now.

Where to start in uncertainty

Right. So how did you know what areas to go into for somebody that’s listening right now? Like what do you recommend for them? If they’re saying, listen, I’m in that exact feeling, but I don’t even know where to

Chris Gillebeau:


Yeah. Yeah. I mean, that’s great. I think it’s a, it’s actually a very apt parallel to think back about that time.

Right. And then something happens that you realize, actually I’m not, there’s a whole lot of stuff I’m not in control of, you know? and that’s really hard. Like when it first happens, it hits you like this ton of bricks. You’re like, damn. I thought I was, I thought I, I had my own destiny or, you know, or whatever, but then, so then once you accept that, then you realize, okay, there’s a small amount of things within my control, whatever that is, you know, 1% or 2% or whatever the number is, what can I do for that?

Right. And so for me at the time, if I go back, like it’s actually quite similar, To what I think people can do now. Like I started reselling, I started, I was like this new website called eBay, had just come out right back in the day. And I started selling, you know, stuff from around my apartments. And then I learned to pay attention to like online auctions, the closing prices of different stuff.

And I was like, Oh, here’s what, here’s what people are buying electronics and computer equipment and photography gear. And like, wonder if I could buy something at one price and sell it for a higher price. Yeah, really, really basic business model. And the funny thing is, so I can wrote the new book, the money tree, and the main character in this book, he’s going through a kind of a similar process of like feeling all this financial pressure and lots of student loan debt, like so many people have now.

And he basically kind of does the same thing in terms of the reselling. So this is something that everybody can do, like especially, you know, Americans or anybody else in a, in a well off country. Even if you think of yourself as not well off, you probably have some stuff in your apartment, in your house, your dorm room, wherever that you can sell.

And, you know, to just be able to make a few hundred bucks, at least at first, it feels really good. And then it’s also going to teach you this skill. Like I said, I’ve noticing other stuff, like what could you buy and then resell. And then it’s not like you’re going to be a professional reseller, you know, for the rest of your life.

But this is a skill that can absolutely like lead to something else. you know, I help you to develop a service business, help you develop a product business of your own, or just, you know, go into like importing products. And I mean, I think what you said about. There’s never been more of an opportunity.

I think that’s totally true. Because back in the day when I was doing this, when I started, it was considered kind of weird, you know what I mean? Like, people didn’t understand, like, it was like this weird thing. Like, why don’t you have a job? Like what’s wrong with you or do it. You’re doing this now until, until you can get a better job or something.

And now I think. Even mainstream, you know, like, people used to ask me in interviews like mainstream journalists, they used to always say, but isn’t this really risky to do this. And don’t you think young people like want the security of a day job? And nobody’s really asking me that anymore because they understand there there’s actually not a lot of security on that day job.

So fortunately now, like I said, it’s mainstream and it’s so much more accessible.

Casanova Brooks:

Yeah, man. And I love that you said that the last piece, which is not a lot of security in a job, because. As I was talking to my team. And as I look at things in this world, we’re always taking a gamble, right. We’re always taking a gamble on something, our spouses, the jobs, whatever, like, and it’s it’s mutual ways, right?

It’s always a gamble because you don’t really know in the end, how it’s going to work out. You hope for the best. I think that you’ve prepared enough, but at the end of the day, we have to bet on something always. Right. We got to like a lot of people they’ll bet on Amazon, right. Or they’ll bet on Apple, if you can get a opportunity to work with those companies, but for those 5% of people that really have it in their heart, I would say.

You gotta be willing to bet on yourself. Right. And that’s what it sounded like. You did, like you took the opportunity and you said, I don’t know where this is going to go, but I know that if I go back to another job, there’s no security in that. Let me bet on myself. And then I’ll learn these skills. I’ll build these relationships and I’ll be able to spot these opportunities.

Where to start in uncertainty

Chris Gillebeau:

Yeah, it was so basic. I mean, if I think about what I was doing, then I don’t know that there was a lot of challenge in it.

It was all discovery. It was all like, I don’t know how to do any of this stuff. I don’t know how to copywrite or I don’t know how to like anything about marketing or, you know, photography, any of the stuff that you’re supposed to do to like. Have a good, you know, online auction listing or whatever, but it didn’t really matter.

You know? And I, and for me, it was like, I mean, I remember when I started making $15 an hour cause I was 19. And my previous job was like earning $8 an hour, you know, at FedEx, in Memphis, Tennessee, like putting boxes on a truck and stuff. And I was like, I have no idea what I’m doing and I’m making twice as much money.

And so if I can learn more, you know, then presumably I will do even better. And, and honestly like as powerful as it felt so like, You’re going to start making money. And eventually I made more than $15 an hour, you know? It was also like the freedom that came with it and the freedom and the sense of possibility and the sense of like, Oh, I can structure my life the way I want to, if there’s something that I want to do, you know, in the morning or in the afternoon, I don’t have to think how can I like work that out with my job or my boss, you know?

Right. Or, or, or whatever, essentially, and something else that you, you said that made me think of like that good job that people think about. Like, even if you are able to get that good job with Apple or Amazon or whatever, you know, assuming you’re doing a good job for them, whatever salary you’re being paid, like imagine it’s a good salary, a hundred thousand dollars a year, whatever the number is, they are obviously receiving a lot more value than that.

A hundred thousand dollars, because it’s a good investment for them. So they are paying you whatever the amount is. And they are receiving probably 3-5 X, 10 X, maybe in return. So the question is what could you do for yourself? You know, to extract more of that, more of that value, even if you can’t be as efficient as like hurting 10 X or whatever, like there’s something you can do to at least replicate that income.

And then from there, you know, from there, it’s like the sky’s the limit.


Casanova Brooks:

it now, is there one industry because there’s people out there right now, they’re saying, okay. Like, I think I could find things for lower and then sell it for higher. Is there one industry that you tell people at least over the last six months that you should be looking into or is it all just, they have to go off of their passion and what they, you know, love to do.

Chris Gillebeau:

I don’t know if it’s either of those two things. I think I’m okay. You know, if you think about your passion, it’s like, I don’t know if that’s always the right approach, because when I was like selling stuff online, I was selling like Lego kits and I was selling like cigars and like fashion and stuff. And I didn’t care.

Like it was about the, it was like, what do people buy? You know, what people buy is what I’m passionate about selling, you know what I mean? Like for me, it was exciting to learn how this stuff works. And so I think we can get hung up on thinking like, Oh man, I really love X-Men comic books. You know, that’s gotta be my market.

You know, maybe it does, but I think like if you’re learning all this stuff, there’s so many other different directions to go. And I mean, ultimately in life, you want to do something that you are excited about. Okay. Like ultimately life you are, but it’s also a mistake, I think, to think too much about trends.

Cause if you’re always like, what’s hot, what’s hot right now. What’s hot right now. Well, I mean, we can have that conversation. We can say, okay, what’s hot right now. Well, You got millions of people that are working from home for the first time. They’ve never done that before. So they’re trying to figure that out and like there’s room for like home office consultants, like at home exercise stuff, you know, Peloton is huge, right?

Any kind of thing. That’s helping people like live the life they used to have, but not, you know, be out and about. And so the problem with thinking that way is like, that’s not going to be like that forever. Right, right. So it’s more helpful to like, develop this sense of observation of being able to look and say, what can I create?

You know, that’s not dependent on the outside world. What can I create? That’s actually going to have some value, you know, in the, in the longterm. So you’ve got this powerful motivational story. You’ve also got some sales experience you’ve got, I think it’s really helpful for people to like, make an inventory of like all these things, you know, all these experiences I’ve had, the skills I’ve, I’ve acquired.

You know, if you went to college or whatever education you had, whatever jobs you’ve had, like all these things together, they can lead to something, you know, they can lead to you, help you finding that business opportunity. Even if you have your job right now. Yeah,

Casanova Brooks:

I love it. And so another thing, and then why it ties in so beautifully is because you’ve been a pioneer in the podcasting world for how many years now.

I know we’re just over 1200 episodes on The School Of Side Hustles. So for how many years now?

Chris Gillebeau:

Well, I’ve done it every single day for the past 1,225 days or so. So I started January one, 2017. So this is the, this is the going into the fourth year.

Casanova Brooks:

Got it. And so where did that idea come from? Did you sell it online now?

You make it a little bit of money. So where all of a sudden was it, was it about. You know, opportunity for monetization and podcast. So what did that look like?

Chris Gillebeau:

Well, I mean, I had, I wasn’t really like selling too much stuff online at that point. I mean, I’ve been an author for nine years and writing books and such.

Yeah. I think for me it was, it’s something I’m motivated to start projects I’m motivated to like impact. I try to have some try to be helpful in some way. And so I thought this is a different medium, you know, I haven’t tried this before. And then I also thought, well, I feel like I’m a little bit late to it, you know, which has always, like, people always feel like they’re late to stuff, you know?

And that’s maybe that’s another message is like, when I started my blog 10 years ago, I felt like I was late because I was like, man, everybody else has been doing this. And like this personal development space is like saturated, you know? And like, obviously I was able to like, You know, make it work. So the same with podcasting, but I also thought like so many podcasts out there.

How am I going to stand out? So the way I decided to stand out was like, it’s going to be 10 minutes a day, you know, 10 minute episodes, no interviews, no guests. I’m just going to teach for it. I’m going to tell different stories of people who are finding ways to make extra money without quitting their job.

I had the first seven episodes, you know, like outlined when I started. But, fortunately there’s a lot of people out there doing this stuff, so had a lot of stories and then we just kept it going since then.

Casanova Brooks:

I love it. And at what point did you start? Because a lot of people right now are thinking they want to start a podcast and maybe they can figure out, you know, what their area they’re laying, how they’re going to be different, but they struggle with, okay, I got to get money because I got to get equipment and yes, we know that there’s ways you could do it at a very low cost.

But monetization has become something that a lot of people are thinking like, look, I can provide entertainment and education. So at what point did you start to monetize your podcast? And what does that look like? That you tell other people when they say, Hey, Chris, I want to start a podcast and I want to make money from my podcast.

Chris Gillebeau:

So I would say more than just thinking about podcasts, because it could be anything. It could be your YouTube. It could be. you know, your blog, it could be some other format. It could be whatever medium is invented, you know, in the next week or two or a month, or, you know, so I think the bigger thing is audience, like, who is your audience?

How are you trying to actually build an audience? Because you know, your audience can be with you, your community. Let’s say it can be with you for years and years. And your community will adapt to new platforms just as you are adapting. And you’re learning new stuff, you know? I mean, one of the reasons why I finally started a podcast, cause I’m, I’m actually not an auditory learner myself.

I don’t learn a lot through through podcast. I don’t listen to audio books that much myself, but finally I realized, you know, it’s not about me, right? It’s about your audience. Like it’s about your community. You know, you might have community that like, if you don’t like video, it doesn’t matter if it is your community, like it will, you should be doing it.

Right. So that’s partly why I started that, that, That show. But anyway, for 10 years, I’ve been like trying to build relationships one by one. Whenever I have a book out, I go, when I’m able to travel, at least I’m able to try to go to as many places as I can for the first book. this is not, I’m not trying to like Dodge the question.

I’m going to come back to it because it’s it’s relevant. for the first book I went to all 50 States. I went to every province in Canada. I was like, dude, if there’s four people in North Dakota who’ve ever heard of me, I’m going to meet those four people, you know? Like, and so that’s the attitude that I’ve had for 10 years is like, I want to show up wherever I can, you know, like you have a big show, you have a big platform, right?

But for a long time, I have to be a little bit more selective now, but for a long time, if somebody wrote me and said, I’ve got a podcast with two listeners, you know, will you come on and talk to me for 30 minutes? I’ll be like, absolutely. Here I am. So the point is, I’m just trying to build this thing so that when the time comes to launch a podcast, then I have a little bit of a platform.

And like I’m working with a publisher distributor on it. So I can go to them and like mutually, we come to a, to a deal where they’re like, I realize I have something to say, I have a little bit of an audience. They have a distribution network. So we actually started right from the beginning with sponsorship, you know, and I know not everybody watching can do that, but that’s why I tell the story of like, it’s not just that I’m lucky.

Like I think I am lucky. I realized that, but I also put in a lot of work over the past 10 years to get to the point of people actually caring to the point where I can start new stuff.

Casanova Brooks:

I got it. So for somebody else that comes into this and they say, listen, I don’t have an audience yet. Right. I’m looking at this.

And I am willing to put in that sweat equity of anybody who has, you know, two guests or whatever, two listeners I’m there.

Build your tribe through Caring

How do I start to build my tribe? Because it’s taking you 10 years, but I’m sure you’ve learned a lot in this years of building your tribe. Now, if you have a mentee. What are you going to tell them, is there a three step process?

Is there a formula that they should be looking at? Is there one kind of hack that they could do to small win?

Chris Gillebeau:

That’s great. Yeah. They just need to pray, you know, to the podcast fairy. It’s like the podcasts ferry will show up and then like one day you’re like, Oh my God, look, look, I got all, you know, all these listeners know, I think the hack is to care.

You know, the hack is to like it’s to do everything. You care, everything you can to care for the people who pay attention to you, even if it is just those two people. And that’s how I like with the blog. I started, I had like five subscribers, you know, after like 10 days, you know, a blogging or whatever.

And one of them is my grandma, you know? And the other four people that I had spammed, you know, people I went to, Hey, come and read the, come and sign up, you know? And I mean, it’s, I, I’ve never had like a big viral. Moment. It’s not like there was one thing that was like, Oh, all of a sudden, not people know Chris Guillebeau, it was a combination of like that blog.

And I’m going to try to be helpful and put something out. That’s useful. I wrote a manifesto called A Brief Guide To World Domination and that got shared a bunch and such. but again, it was all helpful and nothing was for sale, you know, for a long time, for a long time, nothing is for sale. I’m going to, when I do the book tour, I mean, yeah, there’s a book, but the book it $14, you know, I’m going to show up and talk to everybody, whether they have the book or not.

And. I honestly think if you just, if you build this, are you in it for the short term or the long term? That’s the question. Like, if you’re in it for the short term, then that’s a totally different conversation. We could talk more about like the arbitrage thing and here’s the hack and here’s what people are doing to like take advantage of a system.

And there’s nothing wrong with that. Like, it’s fine. It’s going to be fun sometimes, but you’re not really building a business that like, if you actually want to build a business, then that is about relationships. And so you might not actually make a hundred thousand dollars next month or next year or whatever, but.

There, you have it. I love that when you talk about relationships, because just as I was telling you before we hit record, when I did those, those deals in real estate, and I’m still in real estate doing deals, but it’s always about relationships.

Casanova Brooks:

When people look at how have I been able to get five-star guests? On the podcast. And people ask me that all the time, how are you getting these big names? And it’s like, I’m just trying to build relationships. And I truly do care just like what you said. And so there’s so many things of what you could do to go the extra mile, but so many people they want and it’s, and I get it and I bring that up because I want it.

Them to learn from somebody who’s already been a pioneer in the game. And the reason why I say that is because every day when we turn on our smartphones, we’re constantly blasted by somebody who looks like they have it all figured out by somebody who’s ridden the Lambo and you don’t even have that part of it, but they got the Lambo and they say,

And so it’s like, Oh my

Chris Gillebeau:

God, you gotta judge not pay attention to that stuff, man. You got to drown that stuff out because a lot of it is fake. A lot of it’s fraudulent. And even if it’s not fake or fraudulent, it’s just a myth, you know, it’s like, it’s part of their story that they’re doing to convince you that you’re not good enough, but you need to pay them so that you can actually become good enough to eventually rent the Lambo or whatever.

So I think you just have to ignore that stuff.

Casanova Brooks:

Yeah, man. And so that’s, that’s a big deal. So I’m glad that you said that. Talk to me about, was there ever one day, you know, and I’m sure there’s been many, but talk to me about one time that you thought, like I’m done with this and you were like, you know what?

I just want to, I want to go, I want to be done with this. And then how did you overcome that mindset?

Chris Gillebeau:

You know, man. I don’t know if I’ve ever thought I’m done with this. I mean, I think I’ve, I’ve thought a lot of times, like, here’s this challenge, here’s this obstacle, here’s this, I launched this course and I was really excited about it.

I put a lot of work into it and guess what? I launched it. And nobody else cared, you know, like nobody bought it. People said it was, people are like, Oh, that’s a really nice, you know, of course that you did. Mike, did you, did you buy it? Like, Nope. Just, it looks cool. You know, it doesn’t help you right. When you’re trying to sell something.

A couple of them have done, you know? Okay. And then a couple of them that I worked on for a year. You know, not, not so great. And it’s not like in retrospect I can look back and say, Oh, here’s why this book did better than the other one. But when it’s, when it’s happening at the time, like you really have no idea what was happening at the time.

You think this is the thing that I’ve made, that I’m the most proud of, you know, everybody’s going to love it. The last one, sold X number of copies. So this one’s going to sell that and more, you never think it’s going to be like much less, you know, but that happens. And so, I don’t know. I mean, I’ve had all these ups and downs and such, but for me, I don’t think a lot about the past.

I don’t think a lot about like, whether it’s a success or a failure. I don’t really want to, I don’t live off of that. Right. If it’s a success, I don’t want to live off of it because then you’re just, it’s all nostalgia. It’s all like, who cares what you did last year? Right? I don’t even talk very much anymore about like the going to every country in the world thing, because it’s been a while.

I don’t want to like live in that. and it, but if it’s a failure also, like if you just stay in the failure, you’re going to be stuck. So for me, I’m always like, what’s next, what’s next? You know, how can I improve day to day with the gifts that I’ve been given with whoever I have access to and whatever challenge I have, you know, that 1% that’s within my control.

Like we talked about earlier, how can I keep improving? That’s what I think about.

I love it. Was there a time where you ever felt that, like “now my wheels are spinning.”? did you feel like listen and you didn’t want to bask in it, but at one point, did you feel like, look, I got this thing, like I’m the man.

Chris Gillebeau:

Dude. I never try to think like that. I think that’s a mistake, you know, it’s like when a politician loses their election, once they start taking things for granted, you know, like the politicians that are succesful, I don’t want to be a politician, but like, I just an example of like, I want to be the person that’s like.

Fighting for every vote. You know what I mean? Like, it doesn’t matter if I’m 15 points up. I want to be working just as hard, you know, as if I was the underdog. So I’ve never thought I have made it, you know, there’s always, it’s always like, there’s always something else that you can do or improve.

Casanova Brooks:

I love it. Always staying hungry. Right? Always staying hungry, always staying motivated, finding one little piece to let you know that there’s a way that you can improve on it. How much of this would you say? Cause your mindset right now is definitely one of somebody who’s noble. Right. And somebody who is realistic is what I love to think about.

Right. But. At what point did you ever have a mentor? Did you have somebody or was your mindset always like this? Because a lot of people right now they’re struggling and mentorship has been the big thing over the last year, two years. I need somebody to help me. I need a mentor, Chris, will you coach me? Do you, did you ever start out that way?

Did you have one person that really helped you and challenged your mindsets? And now you’re at this spot in life?

Chris Gillebeau:

Well, I want to be careful how I answer the question because there’s a lot of people that have helped me. And so like, I’ve learned from a lot of people, you know, whether it’s, you know, authors and like people online, but more just like regular people in my life, or like other aid workers that I worked with in Africa.

And like, they don’t have, you know, social media, you know, huge followings or anything. They’re just like, you know, changing the world and like serving and such. So I’ve learned from a lot of people, but.


A big part of my, my message is about self-reliance. And I think a lot of people are looking, it looks sometimes, you know, for somebody to tell them what to do when they already know what they need to do, or they like, they’re just afraid to do it.

They’re looking for somebody else to give them permission. You know, it’s like a lot of people that go on Shark Tank or whatever, they’re like, like they’re hoping that somebody will, it’s not just about the check. It’s like they want Mark Cuban or whoever just say like, yes, you can go and start your business and go for this.

And they don’t need that. You know, like they can, you can do this on your own. Like there, there are a lot of answers that you can figure out, you know, whether it’s something technical or I don’t know, something else, like, I don’t think you need somebody who’s like always telling you, like, here’s how, here’s how you find your path.

I think most of us find our path by going down different paths, you know? And you might make some mistakes. That’s okay. Right. If you don’t make mistakes, like if you’re achieving a hundred percent of what you’re trying to. To accomplish, then I think your goals are too small, right? Like your goal is like, I’m going to walk down and get the mail today and come back like, okay, I did it a hundred percent success.

We need to have a better goal than that.


And that’s huge because just like you said, a lot of us, we already know what to do because we’ve been living this life. We’ve we’ve had other mentors, whether it was our parents, whether it was teachers or somebody who’s kind of tried to help put us on the right, you know, straight and narrow path.

And they’ve given us some of their wisdom, but yet, even though we know better, we don’t do better. And in a lot of the times it just comes down to discipline. Right. And so for you, I wanted to ask, what is your cause? You said, Hey, I made this a goal. This is how I’m going to stand out. And now for 1200 and some odd days, you’ve committed to that goal and still staying true to it.

What’s that tip for discipline. How do you stay disciplined and committed enough to, to finish things out like this?

Chris Gillebeau:

Okay. So two tips. the first thing is I think that the number one thing you can do to be productive and disciplined is to be doing something that you actually want to do, because it’s really hard to like, just motivate yourself and be like, suck it up.

You know, one more, one more day, I’m going to keep going. Like, you can do that for a time, but that’s very discouraging. And the longterm, like we’re motivated to do work that we believe in to do something that we. We care about. So I would spend a lot of time on the front end trying to figure out what that thing is.

Like it’s, it’s going to be harder for you to stop doing something that it is to keep doing it. So like with my like Apple watch, I got this streak going for like more than a year now, every day I’m getting my steps or my workout and stuff. And like, I don’t want to stop. I got like for me to stop it, it would be harder than to just, okay.

It’s 8:00 PM and I haven’t. You know, ran today or haven’t done any exercise, I gotta get out and do it. So a streak, a streak can be really powerful and it’s hard in the beginning. It’s a new habit, but whatever it is that you’re trying to do, if you’re trying to like eat healthier, I don’t know, like the longer that you do it, the easier it’s going to be to keep doing that thing.

Casanova Brooks:

Got it. That’s that’s right. They’re two key points. And it reminds me of the book by James Clear “Atomic Habits”. Yeah. And he talks about that a lot and just finding small wins. Right? It’s you can’t eat the whole elephant in one bite. You got to take small bites, but if you start out with five steps, 10 steps, and then you get up to a thousand steps, 5,000 steps a day after that, you know, you almost feel like you’re letting yourself down.

Along. Your journey. Has, has there been, has it always kind of worked out where it just felt like there’s been a lot of luck involved or have you had times where you felt like maybe I do need to go back and get a job?

Chris Gillebeau:

I think it would be like a terrible thing for me to get, like, if I was to get a job or even try to get a job, let’s say, cause I can’t, I wouldn’t even assume I could get a job. Like a good, a good one. What, what kind of job would I do? Like I’m, I’m, I’m 42. I’ve been working for myself since I was 19. Like I’ve never been in a corporate environment.

I don’t like to listen to people. Tell me what to do. you know, I have A.D.D. I’m really good at doing stuff that I care about. If I’m, if I believe in it, I will give 120%. Like I will work harder than anybody that I know, but if I don’t believe in it, it’s like 20%. And so that’s pretty difficult in most corporate environments.

Right. Because you don’t get to choose, like, here’s everything that you do, stuff that you just have to do, because that’s how it works. So I, I mean, honestly, I think I’m not, you talked about risks earlier, but I think I’m living a pretty conservative life in that way. Right. And that particular way, because.

You know, it would be pretty risky for me to be like, what can I, how can I write a resume and posted on LinkedIn and hope that somebody notices me, like that would be a gamble. Right. Whereas I think investing in yourself and like, what, what is it that I can do next? You know, for me, I think that’s much, much safer choice.

Got it.

Casanova Brooks:

Well, there you have it. I love that part too. The next thing is you wrote the book, The Money Tree, right? Because you said, you mentioned early, a lot of people are in student loan debt, right. And they’ve now gotten laid off of these jobs. Right. They got all of this debt to get. Right. And so now how do you advise people without being a financial advisor?

Is there a couple, like steps of what you tell people all the time to get their finances in order? So then they can have more risk tolerance to go out there and bet on themselves.

Chris Gillebeau:

Well, I think the number one thing they needed to do is earn more money. I think it’s not about getting your house in order or like saving money.

And I mean, saving money is not going to help you. If you have a below average income or even an average income, and you have a lot of debts, like you can, you can be frugal, but that’s not going to get you out of that situation that you’re in. Like ultimately you’re going to have to make more money.

That is the, that is the number one thing that you have to do. And so if you accept that as a principle, then the next question is, okay, well, how are you going to do it? Well, you know, if you’re already working a lot or maybe you’re already driving for Uber or something like that, it’s not going to actually get you out of that situation.

So you’re going to have to find a way to create something for yourself, which I realize might sound a little bit daunting, but like we’ve been talking about in this conversation. I think it actually is an opportunity. For people. And I think people can do better, you know, on their own by, by finding a way to buy and sell something by starting a little service by figuring out how to create a product.

I mean, that is a, that is like the number one and number two things they need to do. because I feel like people get caught up in like, Oh, I’m not going to buy my coffee today. And you know, and I’m going to save that $3 and then like, Going to put it toward my debt, which is $60,000. And like, you know, one day, I mean, however many coffees that is later, it’s just not, it’s not going to work.

So I think you should buy whatever coffee you want and figure out how to make more money to pay for that and get out of debt. And so on.

Casanova Brooks:

Got it. I love it. And that’s where we talk. When people ask me all the time, like, should they pay off all their debt versus should they start investing first for real estate?

I always say, make sure you start investing first because if you buy the property right, and you can create some cashflow out of that, then you can use that cash flow to then pay down your debt. And then you’re also getting appreciation and everything else.

So I love that you brought that part up. Was there, has there been one?

Cause you say you’re not auditorial, so you don’t listen to a lot of things is do, do you read a lot? Yeah. Where do you tend to sourcing content?

Chris Gillebeau:

Sure. I mean, I tend to read a lot. Yeah. I mean, I do a few different things. I mean, I’ve watched videos. I do listen to some stuff, but, I read a lot. I have, I have a lot of friends and people in my community.

Like, when you talked about being inspired and like mentors, I don’t really have mentors, but like the people that are in my community, like I regularly feel inspired by them. And so I get a lot of emails from people and. When I’m able to tour, like right now, I’m not of course, but like when I’m able to go out and, you know, for this, for this book, I was going to do a 40 cities.

I was going to be all across North America for probably about two months, you know, every night talking to, you know, a group of a hundred, 200 people or whatever. And like, I always go away from that feeling really like energized and also like, Oh man, I had this conversation with this guy that actually makes me think a little bit differently about how I’m gonna write my next book or the next talk or something.

So it’s a process of like, co-creation in that way.

Casanova Brooks:

Got it right now, but there’s not one. Who’s your favorite author? You said you read a lot. Who’s your favorite author?

Chris Gillebeau:

I mean, I read mostly fiction. I don’t read a lot of like nonfiction business books. Cause I cause like I’m an, I’m a business author, so I don’t, I don’t want to read a lot of other people in my space.

Like a lot of them are my friends and they’re doing, they’re all doing good work. It’s not a criticism. I just, I want to be kind of informed by my own perspective without.

Casanova Brooks:

Cool. Well, Hey man, this has been a phenomenal episode and I think that it’s been, just amazing to have you on the show. And I think people have gotten a lot of value out of this.

I hope they, they have

Chris Gillebeau:


Casanova Brooks:

There’s still somebody out there though. That’s maybe in your same situation, but they’re saying that, Hey. I don’t have that audience. I don’t have, you know, the publisher, I’m not smart enough. I don’t have enough resources. What’s the one thing that you say to that person to get them to just take action.

Chris Gillebeau:

Well, I think what you just said, like, I just have to take, actually have to do something. Don’t worry about the audience. Don’t worry about the publisher. What is the thing that you can do right now? Like on the podcast? I mean, I’ve got 1200 episodes, you know, 1200 examples essentially of people that have done different stuff.

So I would say listen to somebody it’s all free, you know, listen to some of that stuff and. You’re not going to connect with every story or every episode, but the point is to like, find the ones that you do connect with like, Oh, this is interesting. This guy, you know, he got a drone and started doing drone photography for real estate agents.

Actually. I mean, that’s like a big, big market right now, especially for like high, high end properties and such, this guy’s doing really, really well with that. This other woman just talked to, she was doing like virtual meditation circles on Zoom, you know, right now, and she’s got a subscription, you know, thing that people pay 20 bucks a month for, and I forget how many she’s got signed up now, but she’s making two to $3,000 a month on the side with it.

There, there is something out there that you can do. And so I would say, you know, take action. As you said, don’t worry about spending money, you know, any, any idea that costs a lot of money, just discard that one, because the ideas are everywhere. You can find another idea that doesn’t cost money. And ask yourself what the first step is.

And then, you know, if you really can’t take that step, I would say, stop listening to podcasts and stop reading books and start and just start doing what you need to do before you, before you do more research, because sometimes research is like a way to just kind of put things off.

Casanova Brooks:

Yeah, it becomes yeah.

Paralysis of analysis. Cause you’re just, like you said, you’re here so many different perspectives and then it just gets, you stopped in your tracks.

Chris Gillebeau:


Casanova Brooks:

This has been great, man. We’re going to make sure that we put links in the show notes for The Money Tree book also for The School Of, Side JHustle podcast, and also for your website, but for anybody else that just wants to stay connected with you.

Where’s the best place to reach out to you at?.

Chris Gillebeau:

Yeah, man. Thanks. so the podcast is that side hustle, school.com. the new book you can go to moneytreebooks.com, or I am Chris Guillebeau on most social media. It’s @193countries on Instagram. So 1-9-3-countries

Casanova Brooks:

Wow there you have it. Well, remember Dream Nation.

You must take action. Just like you said. And if you are right now suffering from paralysis of analysis, maybe it is time for you cut everything off and just really do some soul searching on what does it take for you to have at least your first step, so then you can get a small wind and build off of there.

But remember, even though it’s in the dream we trust, we must take action. Otherwise it’ll only merely be a fantasy. We’ll see you on the next one.




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