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SPI 717: Making Money in an Economy that Hates You with Chris Guillebeau

You can’t know which of your ideas will take off before you try them. That’s why taking asymmetrical risks—where the potential upside is much greater than your investment—is essential to get ahead today. But how do you practically do this on your path to success, and what outdated rules should you break along the way?

In this episode, Chris Guillebeau of The Art of Non-Conformity shares an inside look at his new book, Gonzo Capitalism: How to Make Money in An Economy That Hates You [Amazon affiliate link]. I’m excited to have him back on the show—his experience in the online space is incredible!

So, how do you succeed even when the odds are stacked against you?

We cover a lot of ground in this session to answer that question. Chris and I discuss building hybrid communities that function online and offline, monetizing your existing skill set, creating in the age of AI, event planning, and more.

Chris is the author of several game-changing books, including The $100 Startup [Amazon affiliate link], and has traveled to and blogged about every country in the world. For more insights from him, go back to episodes 038 and 211 to hear our previous conversations!

Today’s Guest

Chris Guillebeau

Chris Guillebeau is a New York Times bestselling author, entrepreneur, podcast host, and modern-day explorer.

During a lifetime of self-employment that included a four-year commitment as a volunteer executive in West Africa, he visited every country in the world (193 in total) before his 35th birthday. Since then he has modeled the proven definition of an entrepreneur: “Someone who will work 24 hours a day for themselves to avoid working one hour a day for someone else.”

You’ll Learn


SPI 717: Making Money in an Economy that Hates You with Chris Guillebeau

Chris Guillebeau: Asymmetrical risks, you know, where the upside is so much greater than the downside, I think that’s something that people can start applying right away.

You’re constantly taking risks and making choices. How do I invest my time? What do I choose to learn about? You’re always taking risks, but wouldn’t it be great if you can take the kinds of risks where if it works, then it’s going to be amazing.

You know, you can write a book and the worst thing that happens is nobody reads it. Okay, well you’ve learned through that process, and you’ll write your next book, and you reach more people. You know, starting your side hustle, starting a new social account or whatever it is.

Pat Flynn: You know, I really enjoy bringing people on the show that have had an influence on my life in some way, shape or form. And one of those people is Chris Guillebeau. He’s a blogger and a world traveler and an author, a very well renowned author. And he’s got a new book now called Gonzo Capitalism. And we’re going to be talking about how to build a business today and how to succeed in an economy and in an environment that kind of hates us.

Things are kind of stacked against us when it comes to building things online and succeeding. We’re going to talk about what that means and how, but also get into some history with Chris because Chris has, like I said, had a massive impact on my life and many others. I mean, I’m talking tens of thousands of others.

He is the founder of an event that had run for a decade, called World Domination Summit. I learned a lot of things. I’ve met a lot of people through that event and what he’s done and how he’s helped people. Even from way back in the day with his manifesto about the overnight success or the quote unquote overnight success is just so profound and it’s so wide reaching.

So, Chris, thank you for everything you’ve done and I’m excited to catch up with you here today, talk about your new book and talk about how to succeed today and what a person can do to take their skills and amplify them and succeed in today’s world. Let’s have a chat. Here we go. This is session 717 of the Smart Passive Income Podcast, with Chris Guillebeau, author of the new book, Gonzo Capitalism. Let’s do it.

Announcer: You’re listening to the Smart Passive Income Podcast, a proud member of the Entrepreneur Podcast Network, a show that’s all about working hard now, so you can sit back and reap the benefits later. And now your host, he was on the news when he was 10 years old for a fire that happened at his elementary school, Pat Flynn.

Pat Flynn: Chris Guillebeau, welcome back to the show. It has been a while, my friend. Thank you for being here.

Chris Guillebeau: It has been too long, but thank you so much for having me back, man.

Pat Flynn: Yeah, and you know, here you are with another book, yet another book. You are a very proficient writer and author. Your books have done extremely well.

$100 Startup still continues to make an impact out there. And you have a new one now called Gonzo Capitalism. And before we get into what does that even mean? And what is this book about? I’d love to know about outside of the book, what is happening in your life right now? You are a world traveler. Are you just writing books all day or like, what else are you doing outside of that?

Chris Guillebeau: Yeah. I mean, I’m traveling a lot less than I used to, you know, I had this less. A lot less. Yeah. I mean, I have this quest of going to every country, right? And, you know, that kind of took up, you know, the better part of 11 years, at least in terms of focus. And so then I finished that and, you know, I kept traveling and doing some stuff, but then we had COVID and that was a good little reset in some ways in terms of, okay, I’ve been doing things a certain way.

Now we’re forced, you know, to do something different. And so, so traveling a lot less, still making a podcast, kind of followed in your footsteps, you know, with SPI, right? Because I forget which year you started that, but a few years after you started yours, I started this podcast called Side Hustle School. I do it every day.

I’ve been doing it for, I think it’s about 2,400 days. Amazing. So that takes some time. We wrapped up World Domination Summit last year. So, I don’t know, I just try to, try to make things and connect with cool people, you know, be inspired by folks, folks such as yourself.

Pat Flynn: People tell me this too, and I, I, and I have to remind myself about it, so I want to just take a second to remind you about the major impact that you’ve had on so many people’s lives.

And not just like a little impact, but like life changing impacts. I mean, there’s so many people who, when I think about where I met them or, or how I got to know them, it was through, world Domination Summit and what you did there. Now you say you wrapped it. So you’re done with that event. Why?

Chris Guillebeau: Yeah. Done with that.

Well, we did it for 10 years and you know, I think people don’t usually end things well, they just kind of keep going. I think it’s nice to be able to say this was a season. We did this for a long time. It was, it was powerful. It hopefully has some impact and now we’ll do something different. The other thing is when we started at WDS, there weren’t a lot of gatherings, you know, of interesting people or nomadic people, entrepreneurs, people who just saw the world differently or wanted to do something for themselves.

And now there are lots of gatherings, conferences. The world is much more connected in some ways. And that’s great. So it was for us it was always a volunteer effort. You know, it was we ran it as a nonprofit. It was something we did because we love to do it as opposed to like this is a great business model or a sustainable entity, you know, it’s going to continue forever. So I think when you do things for love, you know, there can sometimes be a limit of like how far you can take it. Just because it can kind of, you want to make sure you’re all, you’re always doing something that feels magical. And if it ever starts to like, feel more like a job or something, then you should say, well, maybe let’s put everything into making a big, like powerful conclusion and then figure out what, what else is exciting to do next, you know?

Pat Flynn: Yeah, for sure. And your podcast has done extremely well. Like I said, your books, I mean, you’ve had a huge impact on, on people’s lives. I’m sure you hear it every day and you get messages, but I just wanted to, to tell you here. Thank you for saying that. You’ve had a direct inspiration for my Pokemon efforts.

In fact, at my event recently, Card Party, we did a world record attempt and we actually obtained a world record. And I got that idea from you because you did that every year at World Domination Summit. So thank you for that.

Chris Guillebeau: Oh, it was cool. It was really fun to see. It was really fun to see the photos and videos of it.

You guys just crushed it. It was really fun.

Pat Flynn: Another thing that I’m thinking about all like the timestamps that you’ve had an impact on, on myself and other people. One of them was. One of those early manifestos that you wrote the blog posts about, you know, the 10 year overnight success and these kind of things that have become now a part of just our normal culture of talking with other entrepreneurs.

What’s on your mind these days? What’s what’s your manifesto about today?

Chris Guillebeau: Yeah, it’s so interesting to think about the, you know, the manifestos because I went the overnight success thing. I don’t think in my like 12 to 15 years of making things and sharing them. I don’t know that I’ve ever really had like a viral moment, you know I’ve just had stuff that I just I make and it goes out there and some of it has been fortunate to find an audience and lots of other things have it. And so I just I just kind of keep making it I think that’s the best, you know model for people to follow as for what the manifesto is now if there is such a thing, well, I’m interested in the, you know, the so called new economy, and that’s always a difficult phrase, right?

Because we’re talking about the new economy like all the time, but the new, new economy, I guess I do feel like something shifted during the pandemic in terms of how people think about both money and power. So that’s, that’s a lot of what the new book is about. So I’m doing some talks on that, just kind of exploring that.

I did a bunch of experiments during the pandemic, just my own kind of stuff of like, when I researched something. I want to kind of dive into it and really try to understand it. So I spent a lot of time learning about prediction markets where you can kind of bet on the outcome of political events or all kinds of events.

I spent a lot of time playing video games for money, which I was always interested in because I love playing video games. And then there was all like, oh, there’s blockchain video games. I’m like, how does that work? So lots of experiments. And I guess it’s just helping people understand, okay, what is different with power and money?

How can the average person, or how can the individual, you know, do things to better themselves, to improve their lives and to hopefully get ahead because a lot of people are feeling that the system is rigged or it’s impossible to get ahead or they have so much, you know, student loan debt or, you know, it’s hard to get a mortgage and all that kind of stuff.

Pat Flynn: Yeah, I mean, that’s always been a common theme with the work that you’ve done. It’s always been for the regular person to figure things out and to learn how to, for example, with $100, start a startup. And it’s not, you know, akin to, you know, Four Hour Workweek, right? It’s like, well, it’s not actually a four hour workweek, but it’s the idea behind there.

The, the idea that, okay, it’s not, it’s going to cost an arm and a leg to start a business. You can do this right now. And you shared these different examples. You share it on your podcast as well. With Gonzo Capitalism, what, what is the sort of big takeaway or takeaways from it that we regular people can understand?

Cause you put in the research and like, where do we go from here?

Chris Guillebeau: Yeah. It’s funny you say that about a Hundred Dollars Startup. I used to get complaints. For people who would say, Oh, you use this case study where somebody spent 300, you know I’m like, okay, we’re talking about a principle here, you know, so Gonzo Capitalism, you know, first thing peak marketplace.

I think we are living in an age in which everything is for sale, like every talent can be monetized, every skill, every knowledge set. What people need to figure out is how to package it, essentially, like how to go from your, your set of skills, knowledge, experience, and then turn that into the right product or service.

I mean, you, you have talked about this in lots of different ways, so I’m, I’m just trying to kind of think what is modern, what is current and such, trying to help people take what I call asymmetrical risks, you know, where the upside is so much greater than the downside. I think that’s something that people can start applying right away.

You know, as you go through your life, and it’s not just about entrepreneurship, I mean, that’s like the obvious example, but as you go through your life, you’re constantly taking risks and making choices. How do I invest my time? What do I choose to learn about? What are the relationships that are important to me?

How do I choose, you know, to get closer in a relationship or further away? You’re always taking risks and some things work out. And some things don’t, but wouldn’t it be great if you can take the kinds of risks where if it works, then it’s going to be amazing. If it works, you’re going to, you know, like you’ve done with a whole new community with the Pokemon stuff.

Right? Yeah. If that hadn’t taken off, then the worst thing that would have happened would have been like, Oh, well, I really liked this topic. I enjoy making things, you know, about this. I enjoy the creators and turned out that it wasn’t a huge hit. So now I’ll go back to doing something else, but it did take off, right?

So the disproportionate rewards so encouraging people to focus on disproportionate rewards the asymmetrical risk. What is like that in life, you know writing a book is like that. You know, you can write a book and the worst thing that happens is nobody reads it. Okay, well you’ve learned through that process and you’ll write your next book you reach more people. You know, starting your side hustle, starting a streaming channel, starting a, you know, new social account or whatever it is.

Pat Flynn: How do you analyze the risk on either side, both good and bad? How do you truthfully determine what that might be before taking action on something?

Chris Guillebeau: I mean, just speaking for myself, I don’t really have a scientific process for it. I mean, I’m sure there are some people like with certain, certain businesses, especially where you are going to spend more money and it probably is wise to, you know, to do some more formal market research, validation and so on. But I tend to focus again, just from my own experience and people that I tend to, to work with and connect with, I just tend to focus on ideas that, you know, upfront are not going to have a lot of costs, you know, whether financial cost or, or time cost.

And so if you can so here’s an idea that I’m going to know within 30 days or 60 days at most if it’s going to have some traction or legs and it’s just not going to cost a lot of money because it’s not, then I tend to think, well, why not go for it? And eventually, you know, you as an entrepreneur, you have more ideas than you can, you know, than you have time for.

So you might have to get more specific and you might have to think, okay, what is my core focus? But I tend to think people accelerate that process too quickly sometimes. Especially when they’re starting because you don’t necessarily know like what your great thing is or what your life purpose is when you’re 20 or, you know, really at any age until you start trying stuff, you know, when I started the blog, art of nonconformity, it was, it was deliberately vague, you know, it was like art of nonconformity, here’s some stuff about life, work and travel, you know, it’s like the broadest possible topics you can get and so maybe in some ways it would have been more successful if I was like, here is the niche, you know, here is the thing in the beginning, but I don’t really operate well that way and I just had to kind of discover things along the way.

Pat Flynn: Now, it’s funny you mentioned blog. That was how a lot of us back then in early 2000s, early 2010s were packaging our information and putting it out there in the world. Google was a lot more friendly to us back then and people were subscribing to RSS feed, feeds and, you know, it was almost automatic at that point, but times have changed. And as you said, and as you’ve written in this book, it’s become a little bit more modern. It’s different. How, how does one or what are the different methods by which people are now packaging their stuff? Like what in your analysis is a great opportunity for us today?

Chris Guillebeau: Well, I think a big thing that has changed is the scale and the pace of things. You know, there are a lot of people on TikTok and other new streaming platforms that have enormous numbers of followers, you know, that like greatly eclipsed what we used to see in those early, early blogging days. It’s, I don’t know, it’s everything.

It’s overwhelming. It’s intimidating in some ways, but I like, I have this story of miss Excel. Do you know miss Excel?

Pat Flynn: I do. Yeah. I got to meet her at Social Media Marketing World last year.

Chris Guillebeau: Oh, that’s great. That’s great. You know, so, you know, for any, anybody who doesn’t know. You know, this is a woman who’s making a lot of money, like millions of dollars on Microsoft Excel courses and training and her entire lead generation tool is basically dance videos that she performs on TikTok with like spreadsheet tips and tutorials and such in the background.

And it’s just amazing because in the 100 startup many years ago, I wrote this story about this Indian guy who had a blog about Microsoft Excel. And in some ways it was like a similar model and he was making like 100,000 a year, which was a great income, especially in India. And I wrote that case study, you know, saying, isn’t it amazing?

And now with Gonzo capitalism, it’s like, okay, in less than a year, you know, this person who didn’t have much platform at all now reaches millions of people selling large numbers of these higher priced or at least mid priced courses and the pace, the change, you know, the scale and such. So obviously streaming is, I don’t, I don’t think like start a streaming account is the takeaway.

I think the takeaway is things can happen very quickly. You know, things can happen very quickly, so you might as well try something and if you can package it in a way that that connects to a core need, that’s that’s another thing why she’s done so well, then you’re going to make a lot more money. You know, if the goal specifically is making money, like I mentioned in the book that I know somebody else who has done this with houseplants and they’ve also done pretty well. But nowhere near as well financially as Miss Excel just because of the topic like she chose something that has this direct influence on so many people’s lives so many office workers who spend hours a day working with spreadsheets or databases and so she can charge a higher price than you know you can for houseplants.

Pat Flynn: Do you feel that Another thing that and this is something I’m noticing is that the longevity of the content that we’re creating is much shorter now, meaning in order to stay ahead or do well today, we like, like you said, we have to keep up with the pace of everything because back then, I mean, we could write a piece or create something and it can just work for a very long time for you and it almost feels like we’re in this sprint now to the next goal marker and then as soon as we get there We have to sprint to the next one and there’s not really any time for things to kind of just sit there and work for us anymore less passive really in a way. Do you notice that and and how do we how do we deal with that because that almost is kind of unhealthy.

Chris Guillebeau: Yeah, it is, it is undesirable, you know, so much greater to be able to like create, you know, I think what you and I and other people used to call like legacy work or like, here’s this, I’m really going to create this one blog post. It’s going to be so great.

It’s going to go on forever. And that was always like the Seth Godin model as well, like everything you put into the world is going to have its own little like life and ecosystem. But now, as you say, not so much. I mean, it happens sometimes, but unfortunately. It is this constant race and such. And so I think the question there is kind of like, people are like, what about AI? Like everybody’s asking me this, like every night of the events and isn’t AI going to take over the world? It’s unhealthy in some ways and such. And I think it is unhealthy in some ways. It’s also happening, right? It’s not going to stop, you know, and we’re not going to change the pace and the cadence of, you know, the latest social network, whatever it may happen to be, you know, in a year from now.

So I think because we can’t change that, we can only, you know, change ourselves, or we can only say, okay, well, I can’t try to keep up like it’s not possible for me to keep up with everything. I can’t be everywhere. I mean, maybe like the more team members you get, you know, the more you delegate and such, but I just feel it’s almost an arms race.

So you have to decide for yourself like what is enough. And you have to say, well, here is, and this is what I’ve had to do because I, I tend to get like overwhelmed or even depressed sometimes I’m like, Oh, I’m making these things, but it’s not necessarily having an impact or I’m not reaching, you know, X number of people. Or so and so it’s been more successful than me or whatever. I just have to like pull back and say, well, what, what is in front of me right now? What can I do right now? You know, what can I do right now? How can I create something that is hopefully helpful to someone out there, and then what’s the next thing, what’s the next person of the community or group.

And so I’m not really trying to control the, the broad universe of things, just trying to say, well, you know, I, I am a creator. I like to make things. I’m going to make things and I can’t be responsible for the outcome of everything because so much is beyond my control. Sometimes you make something and it works and it’s, it’s the thing you didn’t expect, right?

Pat Flynn: Yeah, it’s true.

Chris Guillebeau: Didn’t you say to me once that the, the Pokemon focus, you know, may actually end up being bigger than anything else you’ve done and you’ve done some huge things.

Pat Flynn: Yeah, I, it is trending that way. I’ve had people tell me the same thing who’ve been in this space for a while, so, and, and it wasn’t on purpose to do that.

It’s just, I just did something that I loved and enjoyed, and I guess I’m able to keep up because I enjoy it, and, and because I approached it with passion versus, you know, like trying to, I mean, make money from this. The money is a by product of, of the passion and the service to the, to the people there.

That’s fantastic. Yeah, that, that’s really, that’s really interesting. Let’s talk about AI since you brought it up. I have a ton of people ask me about it as well. More of a, how do we use it and how do we automate everything in our lives using it? Because. That’s, that’s what we try to tend to do. What is your, your take on where we’re at with that?

And especially when it comes to jobs and, you know, the value that we have to provide for the world when a lot of the things that we could provide for the world are now able to just be typed into a bot and, and done for us now?

Chris Guillebeau: Well, I guess I think two things. I think, you know, one, it’s, it’s, it’s wise to remain current.

It’s wise to like educate ourselves. Like we don’t want to like put our head in the sand. You know, some of these things are exciting and new and they can have positive uses. And some of these things are going to be able to, to help us. And I think we ignore them at our peril, you know? And at the same time though, I mean, I think like the questions I’m hearing are, they kind of come from a place of anxiety, which I understand creator anxiety.

Why should, why should we even make anything right? If, as you said, you know, the bot is going to come along or other people can do it. And to me, that just goes back to the, like, the core reason of why, why are we creators, or if you like that term or whatever term, you know, artists, writers, etc. Why, why do we do that in the first place?

You know, is it, is it just a job or is, is it just a business opportunity, you know, or is there something more to it? And, you know, I’ve been writing books now for, I guess, about 12 years. This is the eighth book. I’m excited about my ninth book. I’m thinking about what, you know, the 10th book and I actually really like books and, you know, I, I guess I just have to believe that there is a market for that.

There are people out there who, you know, value that medium. And I’m sure there’s some ways that AI can help me, but I don’t envision, you know, completely changing my entire process. You know, I, I like everything about this medium and so I’m going to continue with it. So I think that’s the, like, if you are a creator, we need you to create.

We need you to, to keep making things. Because there is something special that I don’t think AI can, can replicate.

Pat Flynn: Agreed. And my advice is just… Just keep bringing the human elements into it. Make that the forefront. I mean, that’s the, the, the human touch, the personal experiences, those kinds of things are things that AI are never going to be able to compete with.

And so leaning into that is great. Why is the tagline of the book, how to make money in an economy that hates you? Like, does it, does the economy hate us? Like, what do you mean by that? And how is it actually working against us?

Chris Guillebeau: So I should say first, I didn’t come up with it. It was actually the, the UK publisher.

They acquired the UK commonwealth rights and so sometimes they do their own cover and I got a nice note from them maybe like six months or nine months ago that was like, Chris, we really like the book, which, which always means they don’t, they don’t like something like we really like the book, like what’s coming next, you know, let me get to the second sentence and I think the, the original title that we had actually gone with in the US was something about the new rules of money. And I ended up using that for like a, one of the chapter titles. But it’s been pointed out to me and I, I agree that like, people don’t like rules, especially my people are like, why are you selling a book about rules? Nobody, nobody wants rules, right? They want to like break the rules.

And so it was the, the UK team that was like, we like this approach. And I was like, I don’t know that I do like it at first. I was like, that’s really strong, you know? And I sent it around to a couple of people and everyone had a really strong reaction to it. I thought, okay, there is something to this.

And a lot of people feel that’s the system is rigged and that things are not working for them. And people are thinking very differently about capitalism than ever before as well. Even people who believe in commerce and marketplaces buying and selling, they still have a lot of skepticism about overall systems.

And so they believe that the system is rigged against them. Even people with good jobs now can’t always afford a mortgage because they’ve been priced out of the housing market. So it’s not only just young people, quote, unquote. It’s a lot of people who feel that way. And so, yes, I’m trying to always put my focus more on individuals, less on systems and less on corporations.

Less on, you know, it’s all about what is, you know, for that person out there who feels that there is something that they can do. They want to, but they also feel like there are things working against them. What can we do? You know, and I always want to encourage people don’t just get mad about like it’s okay to be mad Absolutely, but you also have to think what can you do for yourself?

And what are the actions you can take today to to better your life and give you more chances in the future? That’s what I’m trying to do.

Pat Flynn: Love it. What are the rules that we should be breaking today to get ahead?

Chris Guillebeau: Great question so the theme for You know, all of my work from the beginning has been, you don’t have to live your life the way others expect.

And, you know, throughout life, there are all kinds of people, sometimes well meaning people, sometimes your, your friends or family, who have like ideas and preferences and things they would like you to do, you know? And I always, my, what I just want people to understand is there are other ways. There are alternatives and it doesn’t mean that every alternative is always better than every conventional way.

It just means that there are alternatives and helping helping people understand like there’s another path you can take throughout life, throughout education, throughout entrepreneurship, throughout personal finance. You know, I am writing a little bit about personal finance in this book as well, because I feel that the so called rules to use that word of personal finance really have not been updated at all in many decades and people come along from time to time with stylistic updates, you know, it’s like here’s someone talking maybe to a different audience or in a different way. But they’re kind of saying much the same thing. I want to encourage people to think about their security as not as their security is not a savings account.

Their security is their skills, right? Their skills, your relationships, your life experience. You know, if you, if you lost everything, you would still be the person that you are. You would still know people. You would still have skills you could rebuild, right? So what can you do to keep investing in yourself as opposed to, I mean, it’s fine, it’s good to have savings accounts too, but I think investing in yourself is more important.

Pat Flynn: Agreed. A thousand percent. I’m curious to go back in time with you, to know when you decided not to go down the conventional route. Was there a moment or what in you made you go, I don’t want to do what everybody else is doing and then literally start a movement around it?

Chris Guillebeau: Well I think there’s a few things. I mean, I, I kind of goes back to like troubled adolescence, you know, and like juvenile, juvenile delinquent, Chris, you know so it depends on how far back we want to go. I can fast forward a little bit to like early twenties and, you know, I was an aid worker for several years in West Africa.

That was a really wonderful, transformative experience that kind of affected how I saw the world in lots of ways and, and started traveling out of that experience and, you know, had been to like maybe 50 countries when I started thinking about, okay, how could I turn this from just like something I’m doing from for myself into something that could be interesting and maybe, you know, helpful to others.

So there was a long process of like several years of thinking about that. And thinking what does it look like and finally started the blog like on my 30th birthday and kind of went from there. But even then, like even though I’d been thinking about it for a while, I started the blog and I was like, Hey, everybody, this is a blog about travel and, you know, come and follow my journey to these countries or whatever, which is a very like small vision, you know, and I learned really quickly that from people that were like emailing in or something that Oh, this actually has the potential to mean something much more.

This has a potential to mean a lot more than just like Chris’s travel journey or whatever. And I started hearing their stories of how they were connecting and what they wanted to do and realized that it made a much more like emotional connection with people. And so then I started thinking, okay, How can I help people to pursue their own goals and how can this be a model for other people?

And, you know, you use the word movement, which is very kind of you, but there wasn’t a great strategy behind that. It was just, let me start with what I got. Let me put out, put out some things. And then when you, when your work meets a connection with other people, that’s when the real magic happens, right?

And I started doing meetups and hearing stories of folks and everything went from there.

Pat Flynn: Yeah, the community has always been something that I know has always been important to you and I am taking sort of a spicy take in SPI right now to say like, you have to have community in your business and what you’re doing or else you’re going to be left behind this amplifies the human element right that I talked about earlier with relation to AI and we’ve been focusing on that the Pokemon thing is definitely that but you’ve you were early on on really bringing the community together with your event and your meetups and stuff.

What? Yeah, would be a low friction way to do that today. I’m curious to hear your thoughts because I feel like that would be a great way for people to fast forward their own version of something that feels good, it’s fulfilling, it’s also, you know, of service to people, and it’s something that I’m noticing everybody’s craving right now, we’re craving connection.

How would you start a community today?

Chris Guillebeau: I think I would think hybrid from the beginning, hybrid meaning online and offline. And this is just an idea, right? It could be different, different people. It depends on where you live and such, but I would try from the beginning to think what’s a way that we could bring people together through, okay, so maybe there is the, the online platform, but there’s also like we are planning some sort of in person meetup. I mean, you mentioned human, you know, and probably I’m thinking this cause I’m on book tour now, which I haven’t done in years. I just started this week basically. And it feels so strange and familiar at the same time.

Just the other night I went to, you know, like talk to people in Phoenix and I’m like, wow, it’s great to see you. While I, you know, like I used to do this all the time. So in my mind, this is fresh. So I guess if I was starting over, I would, it would be like, okay. I maybe I’m not known. I don’t have a lot of followers, but there are some people out there that I know, maybe I’m going to put together an event that has five people, or if we’re kind of spread out, maybe there’s a group that we’re going to meet online once a week, you know, with five people are going to talk about a topic, or we’re going to share a story, or there’s some theme to it.

I think that’ll, that’s very helpful. You know, some kind of theme or routine and rhythm to it. And maybe it’ll grow from there. Yeah. You know, and maybe it won’t that’s okay too, but anything that is like a regular cycle of humanity, I like that. I’m going to kind of think about that more and adopt that myself.

Pat Flynn: You know, I love that a lot. And going back to your point earlier about sort of risk assessment. I mean, the pros of bringing people together far outweigh the cons of, of attempting to do that. And I love how you, in a couple examples earlier, you always just say, well, worst case scenario, I think it’s important to think about that.

And sometimes we do think about that and we let our brains go a little too far of what the worst case scenario would be. I know I’m not, I’m that kind of way. When I first started speaking, I was like, I’m going to die on stage. I’m just going to die out there. I mean, that is a pretty worst case scenario.

Yeah, that is a pretty worst case scenario for sure. And and then I would make it even worse than that somehow. But when you think realistically about what, what the worst thing that can happen. It’s actually not that bad, but then, you know, the ceiling for how or where this could go is, is almost endless.

And, you know, to see you take an event and some meetups and turn that into a 10 year long tenure with World Domination Summit and the impact that that’s had and the friendships that I know people have made together there because of you. I mean, you’re always going to be the person and the reason why all those great things happen to a lot of us.

So it would behoove you to bring people together in whatever capacity you can. And like you said, it can just start with five and five can become ten and fifteen. And did you ever feel that World Domination Summit grew too big? I’m curious your thoughts on that and also selfishly asking that as well.

Chris Guillebeau: I don’t know if it grew too big.

It definitely did grow a little fast in the beginning. And then we kind of settled a little bit for years, I don’t know, years five through ten. I think years five through ten were our best years. In the beginning, we didn’t really know what we were doing. And in some ways that can, in some ways that can be a benefit, right?

Because you’re not doing things the way other people do them. But then there also is like a certain expertise and skill that comes from, Okay, we actually have learned like there is a good way to like organize programming and, you know, there are things we can do with logistics that will make it better for everyone, a better experience.

We can save money in certain ways than use that money towards things that have a greater impact. So I think the final years were probably the best years in that way. I think for me, the thing that was difficult was I don’t know, want to be a full time event planner, and I love the three weeks that surround the event.

Like I can go all in like a few weeks ahead of time, but it kind of requires a year long planning cycle or at least a nine month planning cycle, you know, to put that on. And I’m, I’m just doing other things. And a lot of the other team members kind of felt the same. And so we were really able to like rally for a time to do it.

But I think it would have, it would have been unhealthy to have continued it, at least for now. Maybe we’ll come back with something new. You know, Jonathan Fields, another mutual friend of ours. You know, he had a camp, Camp Good Life Project that he ran for five years and then stopped it. And I think he’s, he’s at least thinking about bringing it back now.

He’s had a couple of years off not just COVID, but also just like he wanted some space for it, but now he’s going to bring it back. So maybe we’ll, we’ll do something at some point.

Pat Flynn: Outside of books and events and the things you do for work, what are you doing for fun these days? And you don’t mind me asking, you know, with your success, are you using where you’re at now as a stepping stool to something else. Like what is the next bigger thing that Chris Guillebeau is going to, going to put into, I I’m reminded of, you know, James Clear and his success with Atomic Habits and, and kind of tremendous, tremendous success and, and the things that he’s investing in now to not amplify his success, but even bring others along the ride.

It’s, it’s amazing. Just want to get into your head a little bit about what you’re doing with the success that you’ve, you’ve earned.

Chris Guillebeau: Well, the past couple of years have been interesting. I did kind of step away from some stuff. I didn’t do a lot of social media. I kind of accepted that there were some things I was good at and some things I wasn’t, and I was just going to kind of focus on those things.

And I did take a lot more time for myself, focusing a lot more on health and wellness and exercise. You know, these days I run every day, and I love that. And I started playing video games during the pandemic after like a 15 year hiatus of not doing that. And so it’s like, oh, I have a hobby again. I tried to have a hobby for years and years, and I would always, I just… It wasn’t good at it. I was like, Oh, I gotta, I gotta be doing something. I need to like do something that has some sort of deliverable to it. And of course, that’s not a good way to live your life. So I’ve just been trying to be a little bit more intentional about health, wellness, relationships, spirituality, all that.

But I’ve got more, more lessons to learn. I’m sure.

Pat Flynn: What video games did you get into or are you into now?

Chris Guillebeau: I got a PlayStation, a PS4 during the pandemic, and then I had missed so many years of gaming. I felt like I was in a great place because, you know, over the past 10 years, there were all these like really great games that had come out, you know, like triple A titles that I had never played.

And now there were like $20, you know, so I never had to like buy the new game. So I went to play through the Uncharted series, which I really liked. I enjoyed it. Yeah. So good. Felt almost, like, I don’t know, just felt really, really special. I’m trying to think what else I played. I don’t like the open world games that you can just go, there’s like, it can go on for hundreds of hours.

I actually like to have like a little bit of an objective, you know, and like we’re on this, this mission. I got a Switch also, so play some, play some Switch.

Pat Flynn: My audience knows this, I’ve found a new hobby in fishing lately during the pandemic. And that has been great because it’s gotten me outdoors again.

Chris Guillebeau: Yeah, it’s so tactile.

Pat Flynn: Very tactile and out in nature and I can do it with my family and friends and it’ll, you know, I’ll have it till the day I die. And, you know, it’s also reminiscent of a lot of Good memories that I have from childhood as well. So it’s been neat to find that and I can put the device down.

And what I’m finding is that, you know, the only trouble with it is that when I am actually actively fishing and it’s bass fishing on a lake, which is a lot more strategic than, you know, fishing for carp or trout, where you just put your bait in and you kind of just wait, I have to, if I want to get good at it, which I want to get good at everything I do, there’s so many factors from water color, water temperature to barometric pressures to what kind of bader kind of around the time that I’m fishing and seasons, all this stuff. The time goes by so quickly. I don’t know if you feel this when you play video games, but a 12 hour fishing session feels like an hour.

Chris Guillebeau: 12 hours. That’s incredible.


Pat Flynn: It’s, it’s flow state to the max. I’ve never felt it in anything other than maybe writing actually. When I’m in a good state of mind, but what’s putting you in the flow state these days and how do you get into that mode, especially when you’re working? I’m curious.

Chris Guillebeau: I don’t have a 12 hour flow state that I’m impressed.

I’ve got it. Maybe I have to learn about bass fishing. Maybe this is going to be your next podcast or your next.

Pat Flynn: Oh, I’m trying hard not to make a YouTube channel about it, Chris. That’s the problem.

Chris Guillebeau: YouTube channel. Oh my gosh. Well no, no, honestly, I think you win there. You win with a lot of things, but I definitely don’t have a 12 hour flow state hobby.

And video games, I think, are good, but I don’t actually want to play video games for 12 hours a day. You know, I think, right, to have something you can… It’s probably a good thing. Right, exactly. I mean, people do that, obviously. A lot of people, a lot more people play video games for 12 hours a day than go fishing for 12 hours a day.

But I don’t necessarily think it’s it’s healthy.

Pat Flynn: Agreed. Chris, this was great to catch up with you on, and everybody should definitely check out Gonzo Capitalism, check it out on Amazon, or do you have a page, perhaps, that you want to drive people toward?

Chris Guillebeau: I mean, I’m happy for them to buy it wherever is good for them, but on my website, Obviously, there’s an Audible, there’s Kindle, whatever people like. And the podcast is called Side Hustle School.

Pat Flynn: And do you record your own audiobooks?

Chris Guillebeau: I do.

Pat Flynn: Nice. That’s what I like to hear. I love it. Yeah. Gonzo Capitalism, check it out. How to make money in an economy that hates you. This has been great.

Thank you, Chris. Appreciate you. If there’s anything I can do for you, let me know. And, you know, just happy to call you a friend and, and thank you for inspiring me and millions of others.

Chris Guillebeau: Amazing. Thank you for all you do.

Pat Flynn: Alright, I hope you enjoyed that conversation with Chris Guillebeau. You can check out his work, everything from $100 Startup to Gonzo Capitalism on Amazon, of course, or on his website.

Just such a joy to chat and catch up with him. I know he’s usually super busy and traveling around the world. I mean, he’s probably the only person I know who’s literally been to every single country. He just seems to accomplish so much incredible things and I’m very inspired by him and by his work. And I hope you are too.

So definitely check them out. Chris, thank you so much again for your time and what you’re doing today. And thank you for your book. And I look forward to chatting with you in the next conversation we have on Friday, this coming Friday. Every Friday we have an episode coming your way in addition to these interviews that we have on Wednesday.

So make sure you hit subscribe if you haven’t already. Thank you so much. Take care and I will see you in the next one. Cheers, everybody. All the best.

Thank you so much for listening to the Smart Passive Income podcast at I’m your host, Pat Flynn. Sound editing by Duncan Brown. Our senior producer is David Grabowski, and our executive producer is Matt Gartland. The Smart Passive Income Podcast is a production of SPI Media, and a proud member of the Entrepreneur Podcast Network. Catch you next week!

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