5: The Life of Chris Guillebeau – Visiting Every Country in the World While Building a Startup with $100, a High Traffic Blog, and Making a Difference

Nathan: Greeting from Melbourne, guys. Thank you for joining me today, and this is episode number five of the “Foundr” podcast. As I’ve mentioned in previous episodes, if you’re enjoying these interviews, please make sure you check out the magazine. “Foundr” is a digital magazine on the App Store and Google Play store, and it is action-packed with tactical, strategical, and just really gold content. It’s there for you, the entrepreneur that wants to know what it takes to build a successful business. If you’re sick and tired of all the glamorous success stories, this is a magazine for you. It’s where I spend all my time. Yeah, it’s really my life’s work. So, yeah, if you’re enjoying these interviews, please go and support me and check out the magazine. You can download it in the iTunes store or the Google Play store.

Now, this brings me to our episode with Chris Guillebeau. Guys, this guy is an absolute machine. He has visited every country in the world, is a nomad that travels the world on his laptop and lives a lifestyle that most people would envy. He runs “The Art of Non-Conformity” blog, which is a blog that teaches people how to challenge the status quo. He’s also a best-selling author, runs the world-renowned World Domination Summit every year. In this interview, Chris really shares with us what it takes to live the dream. We actually don’t talk tactics too much. But I found it really interesting to gain an insight into someone’s mind who is trying to have a massive impact on the world.

A lot of people talk about, you know, “I wanna change the world,” and as Chris describes in this interview, a really big thing to say. And he goes through his…how he’s tried to make an impact. I just want you to think about that for a second. Chris is a New York Times best-selling author, he runs an extremely high traffic blog. He runs one of the coolest events on the planet, hosting over 3,000 people from all around the world.

And yeah, he travels the world constantly and he’s living the life of freedom, fun, and adventure. And I found it really, really interesting to see how he thinks, see how he operates, see how he challenges himself, and see what goes through his mind. Yeah, it was a really, really cool, interesting interview today. So, that’s it for me, guys. If you are loving this podcast series, please do me a favor and leave me a five-star review. It helps more than you can imagine. Now let’s jump into this interview.

Today I’m speaking with Chris Guillebeau. He’s an entrepreneur, writer, “The New York Times” best-selling author, world changer, travel hacker, and is the founder and creator of the World Domination Summit. So, Chris, I just wanted to say thank you for taking the time, man.

Chris: Thank you for having me. It’s a big honor.

Nathan: Thank you. So, can you tell us about how you got your job?

Chris: Well, I’m not sure I count it as a job per se because I’m actually not a very good employee. You know, I’m not really good at working for anyone else. I discovered when I was quite young, maybe about 19 or 20 years old, that I’m basically unemployable and I had to find a way to make a living somehow. So I guess, for about 10 years or so, I did all kinds of different entrepreneurial adventures. I also lived overseas in West Africa for about four years as an aid worker. Just kind of doing anything I could to support myself and to allow myself to do the things that I was more interested in doing, whether that was traveling or playing music at night or volunteering. As I said, I did that for about 10 years.

And that was great but then when I was turning 30, I thought, “Well, this is all fine and well, but what’s next? What am I trying to work toward over time?” And that’s when I decided to begin a career as a writer. And so, I started a little blog in 2008 and I started this project of visiting every country in the world. And I said I’m gonna write about it and document it for anyone who cares. And slowly but surely, people started reading, and that blog then became kind of a business and community of its own.

And then I wrote my first book out of that experience, and then I kept writing books. And that’s what led to the World Domination Summit and a lot of other things. But I guess, for me, it’s just been about doing things that I’m excited about and finding a way to connect those things with something that’s valuable to other people, and that’s been, you know, probably the impetus for the whole journey.

Nathan: The thing with you is, you’ve achieved so much in such a short span in time, like the platform that you’ve built, the audience that you have, especially with The Art of Non-Conformity and the World Domination Summit. I’d just like to know how do you create a compelling story with your blog?

Chris: Well, I don’t know if it’s about, you know, just deciding for yourself, like, “How am I going to create a compelling story?” I think a compelling story comes from within. It comes from our own lives and it’s more about, “Okay, what do I want to do with my life? What’s the story that I want to tell with my life? What do I want to live?” And, you know, for me, I was motivated by two things. I was motivated by pursuing my own dream, and that dream was very much about independence and freedom. You know, I didn’t wanna work for someone else. I wanted to be responsible for myself. I wanted to be able to travel, you know, whenever I wanted. I was very oriented toward goal setting, so that’s why I took the travel and the goal setting and put it together and decided to go to every country.

So that was one side of it. But then the other side, I guess what I found, like, ultimately unfulfilling on my own was just doing my own stuff. I wanted to connect that to other people. So, I guess whatever success the project has had in terms of the book and all that, has been on not just focusing within myself but on saying, “Okay, how are other people gonna care about this? Why is this gonna make a difference for other people’s lives?” Because if I’m just traveling, there’s nothing wrong with that, but no one else really benefits from it. It’s just me. But if I can find a way to maybe show other people how they can travel, or help other people become self employed, or help other people do something for themselves, and then maybe if I can connect some of those people to one another, you know, hopefully that has some value. So, I think whatever success I’ve had has come from putting those two things together as opposed to just treating them, you know, completely separate.

Nathan: Okay. So, there’s a lot of things there that I’d like to unpack. But the first thing that shouts out to me is you talk about goals. How do you set your goals?

Chris: You know, I’m pretty intentional with how I set my goals. I do this process called an annual review every year. I usually do it in December, and I go away for a few days and spend a lot of time thinking back about the year that’s just passed. And I look at, you know, what went well during that year, as well as what did not go well, what did I achieve, you know, what was I happy about, as well as what were my failures and my struggles. And then from there, I kind of look ahead to the next year and say, okay, you know, what’s next year gonna look like? And I have different categories. I have, you know, business goals, and writing goals, travel goals, community, you know, all that. And then I try to figure out, okay, you know, how can I make a few specific outcomes for each of these things? You know, what are my goals for my health? How much do I wanna exercise and workout? What’s that gonna look like?

And then I just try to structure my life around those things and say, “Okay, to achieve this, if I wanna write a book,” you can’t just say I’m gonna write a book next week. You know, for most people it takes months or the better part of a year to write a decent book. And so, you have to align the short-term actions with the desired long-term goal. So, in my case, a book for me is about 70,000 words. I break that up and say, “Okay, I need to write 15 chapters. And maybe I’m gonna write 1,000 words a day,” has been one of the habits that I try to maintain. I can’t write a 70,000-word book in one week, but if I write 1,000 words a day, you know, over time, I’m gonna get to that goal. So, it sounds kind of structured. And now that I’m telling you this, I worry maybe it sounds too, like, routinized or something. But, like, for me, having the goals actually helps me achieve what I want to do because they’re the goals that I’ve set. They’re not goals that someone else has, you know, imposed on me.

Nathan: Yeah, okay. I see. Yeah, no, I can hear the desire when you talk about it. And I think I’ve gone through a massive process this year with setting goals.

Chris: Excellent.

Nathan: For me, the biggest piece is the desire, how bad I really want it, and that’s, I think, how I’ve structured mine in order. Because everybody has a ton of goals, but you’re not going to achieve them all.

Chris: Yeah, yeah. Well, that’s great. No, I like the prioritization. And I think I also like…I sense maybe your goals are kind of specific as well, which is good because a lot of people have very vague goals. They’re like, “My goal is to, you know, I can improve my health or exercise more,” or “I want to make more money,” or whatever it is, and that’s not very specific. You know, you don’t know when you’ve achieved that goal. And so, I always like to kind of say, “Okay, here’s exactly what it’s gonna look like. I know I’m going to have achieved this goal when, you know, I meet this variable or whatever.” And I think it also helps to know what you really want and be willing to sacrifice for it because you’re willing to give something up in the short term to achieve something in the long term. So that’s a lot of what goals are about for me.

Nathan: Yeah, no, that’s awesome. And this leads on perfectly to the next question I was gonna ask you, and that is, people look at someone like you, Chris, and they only see the end product sometimes. So I wanna know, what do you have to sacrifice to be where you are today? What did you have to give up? Can you give us a little bit of an insight to that?

Chris: Yeah, what did I have to give up? Wow. I had to give up some of my pride, I think, some of my insecurities. You know, I was always kind of a private person, just did my own thing and traveled and didn’t really want to, like, put something forward to the world because I was worried that people would criticize it and, you know, I was always kind of sensitive to that. And for a long time, it was just much more comfortable to kind of, you know, have a…I had a business. I had a decent income. I could travel and do my own thing. But I didn’t have something, you know, bigger, and that bothered me. And so I guess, you know, finally I was like, “Well, I’m just tired of doing my own thing and not really challenging myself.”

So that’s one thing. But I would also say, you know, I don’t feel like I’ve sacrificed, you know, a great deal because what I’ve received in return, just the amazing people that I’m fortunate to connect with, this career, all these great projects that people are doing that I have a small part in, for me it’s like far much more gain than any kind of sacrifice.

Nathan: I love your blog, “The Art of Non-Conformity.” The question that I had for you is, is the feeling that I get when I think of your message. It’s really that you don’t have to live your life the way other people expect you to. I wanna hear your opinion on why is that. Why do you feel that way?

Chris: I think maybe at first it’s important to think about why so many people do live their lives, you know, according to other people’s assumptions or expectations. I think it’s often because they don’t realize there’s any alternative out there. And I’m not really interested in encouraging people just to rebel, you know, for no good reason. I did that when I was a teenager and I didn’t have the best results from that. You know, I just didn’t like authority and I just kind of wanted to do my own thing and not go to class or whatever. And that’s fine, but you don’t really benefit from that. You don’t gain from that.

So, I guess what I came to realize later and what I saw many other people doing was, you know, they weren’t really intentional about their lives. They just kind of followed a certain path because that’s what everybody else was doing. You know, in terms of their education, in terms of their career, decisions that they made about money and debt, relationship decisions, all these kind of things.

And there’s nothing wrong with those decisions. You know, I’m not interested in criticizing other people or, you know, second guessing other people’s motivations, but I think so many people aren’t aware that you don’t have to do it that way. You know, if you want to, there are different paths, and, you know, education is changing so much and careers are changing so much. And this isn’t something that you have to go through a normal process of education and then work for someone else for 20 years, and then maybe one day you can do something different. You know, I feel like people of all ages are questioning these different assumptions, and not just questioning them but then taking action.

So, you know, I guess what I hope to do with that message, you don’t have to live your life the way other people expect, is just to show people that there’s more than one way. There’s more than one path. And if you’ve ever wanted to do something different but you feel this pressure from society, from your family, from friends, you’re not alone. There’s all kinds of people all over the world, you know, who are doing good things for themselves. They are pursuing a dream of their own and they’re also making the world a better place. And, you know, it’s not just about some author, some blogger, some celebrity or anybody else kind of telling you this. It’s about shining a spotlight on all kinds of people from different cultures who are doing it in their own way. And that’s probably, like, the primary motivation for the work I do with that message.

Nathan: Love it. So tell us about changing the world. One thing that I’ve noticed among every single successful entrepreneur, somebody that’s achieved massive amounts of success in “the world of society,” you know, they’re doing amazing things, having a massive impact on the world, these are the people that, you know, they want to change the world on a fundamental level. Tell us about how you want to change the world.

Chris: You know, changing the world is great, but it also sounds kind of…you know, it sounds really high level. It sounds, you know, “How am I gonna do that?” Like, I don’t know. You know, who’s gonna change the world? So, I guess, for me, I always focus on, okay, what is my sphere of influence? You know, who am I? Not just me answering this question but anybody, like, who reads the magazine, you know, who hears this interview. You know, everyone has a circle of influence. They have people that trust and respect them and look to them for certain things. And I would say you start by, you know, changing yourself. You start by being helpful to people. You start by asking yourself, you know, what can I contribute to? What can I be a part of?

You know, when I went to West Africa, you know, I didn’t really have any specialized skills. I was just a part of this organization that needed volunteers and it was a hospital ship. And so, most of the people on the ship were highly qualified in these medical areas or else they were qualified in maritime areas. And I just went to manage a warehouse and to carry boxes around. And I absolutely loved it. It was so, so good because I felt like I was tangibly making a difference. I felt like I’m carrying medical supplies, you know, into a village in Sierra Leone that had just emerged from a civil war and if I didn’t actually bring those medical supplies then they wouldn’t have any at the clinic. So it was a very direct correlation, as opposed to just, you know, writing a check to somewhere and you hope something good’s gonna happen with it but you don’t really know because you’re not there.

And so, the other point is, I benefited from this. You know, like, I would come home and go back to the States and see, like, friends and family once a year, and everybody would say, “Oh, it’s so great what you’re doing. Thank you for helping.” And I always felt kind of false about that because, you know, I was like, “Well, hopefully I’m helping. Hopefully, there’s something good that’s coming of this, but it’s actually really good for me, too. Like, I’m being changed through this process.” And so, I think anyone who wants to do something big with their life or has big dreams, by focusing on that question of how they can help, you know, it’s good for humanity but hopefully it’s also good for them too. Because it certainly has been for me.

Nathan: Yeah, no, that sounds really well for me because it always comes back to the value and the problem that you’re solving. The bigger the problem, the more you’ll be rewarded.

Chris: Yeah, I like it. That sounds good. But, you know, for me, when I had that opportunity to go overseas, it did sound kind of big. But I’m so glad that I did. You know, it led to so much later. So, I guess I would say if you have an opportunity or if you see some challenge and you’re trying to decide, like, “Should I or shouldn’t I?” it sounds kind of cliché but I really like this statement about how we tend to regret the things that we don’t do more than we regret the things that we do. And, you know, in the case of that experience of going to West Africa, if I went there and I didn’t like it, or I wasn’t happy or it just wasn’t good, I mean, the worst thing that could happen is I just decide to go home. So I think you should always try something. You should always experiment.

Nathan: That’s right. Because it all comes back to your comfort zone too. How actively do you push your comfort zone?

Chris: You know, that’s a good question. These days, I don’t feel like I push it very much, and it’s kind of bothering me. You know, you can get into a routine with anything you do, right? You could even get into a routine of, like, telling people not to be in their routine. So, I wanna be careful, like, not to get into some meta thing in my own life, you know, where I’m not challenging myself. So, I guess one thing, you know, that I haven’t done recently, I haven’t had a new book out. And so, I haven’t been going out on the road to meet readers. I’ve been traveling still, but in 2012 I went to 40 cities. I did events in 40 cities and I had conversations with readers everywhere I went. And I didn’t do as much of that in 2013.

And so, when I was thinking about the annual review, I was thinking, “This is something that I miss.” And so, like, later this year I’ll have a new book and I’m gonna be going to at least 40 cities, hopefully more, all over the world. And it’s not just about promoting a book. It’s about, you know, having these conversations and hearing from people, and I’m always changed through that process. And so, hopefully, I’ll get back to pushing my comfort zone a little bit more soon.

Nathan: Awesome. It’s such an awesome feeling to have an impact on somebody else’s life, like doing the work that you’re doing today. It’s amazing.

Chris: That’s kind of you to say. As I said, I feel very fortunate that I can do what I do.

Nathan: Love it. So, let’s talk about travel. You’ve traveled to every country in the world. Is that every single country? There’s 200…

Chris: One hundred and ninety-three.

Nathan: One hundred and ninety-three.

Chris: Using the United Nations’ standard of member states. There’s 193 member states. There’s a number of other places, you know, which are somewhat unique but they aren’t actually, you know, classified as countries. So I’ve been to many of those places as well. But just for the purposes of the goal, I count the 193 UN countries.

Nathan: Wow. Now, that’s an amazing feat. And I know that you’re a travel hacking expert. I don’t wanna go into it too much. I’m more interested in the driver behind that. What is it that excites you about travel?

Chris: Well, I just always loved the process of discovery and exploration, and I loved kind of just getting out of what was normal to me and seeing how life was different around the world. And then after I lived in Africa for a time, I also kind of came to love the process of travel, or the “pro-cess,” you might say. I liked the part about figuring out how to go from place to place and deciphering all the logistics. And I actually liked being in transit to go places. And I noticed that not everybody likes that. Some people just want to be somewhere. They don’t want to actually, like, plan it out and get on the plane and deal with the bus or whatever, but I actually like that.

And so, into about 50 countries, that’s when I decided to go to 100. My first goal was I wanna go to 100 countries, like, sometime in my life. And then I started working toward that goal and I realized it wasn’t actually that difficult because I could choose which countries to go to. If I didn’t want to go to a hard country or if I had a problem getting a visa or something, I could just omit that country and go somewhere else. And so, as I got closer to the 100, I decided to set the goal to go to all of them. And that’s what I’ve been doing for the past 10 years.

So the driver, I guess, was, first of all, a love of travel. But then also a love of a challenge itself. I really liked the idea of making the list and then figuring out, “Okay, how many countries are there in the world?” like you said and, “How do you get to them all? Are there countries that are dangerous or difficult? Are there countries that are just remote and really hard to get to?” I remember when I was in Australia and I went to Nauru. Almost no one goes to Nauru. But when I went from Brisbane, there was six people on my flight. There was six people total, and that was a weekly flight. And I liked figuring that out. I liked figuring all that stuff out and seeing how to make it possible. So that was the motivator.

Nathan: It’s crazy to even think about. Because some of these countries would be extremely dangerous. Were you ever scared?

Chris: Most of them were not, though. That’s the thing. You know, 193 countries in the world, the vast, vast majority of them are totally safe. At least no more dangerous than places at home. You know, there are different neighborhoods in almost any city in the world that you wanna be careful in. So I guess I always tried to be cautious, and there were a few times that I was frightened. But I would say, like, you know, 180 countries out of 193 always felt very safe and was always treated with respect and hospitality. So, it was a great experience.

Nathan: Wow. I’m sure it would have been more than just a great experience. To be able to even say that is an amazing feat. But that’s awesome. I love it. Let’s switch gears and talk about “The $100 Startup” and business. The majority of the readers and people listening would be either just about to start their entrepreneurial journey or just on it. So I’d like to hear what are the components that you believe it takes to build a successful business to fund a life of freedom, fun, and adventure?

Chris: Yeah, excellent question. So, with “The $100 Startup,” we did a lot of research, talked to more than 1,500 people all over the world, who had all started a successful small business without spending a lot of money. Most of them spent less than $1,000, a lot of them $100 or less, thus the title. Almost none of them had gone to business school. Most of them did it by, you know, kind of following their passion or at least pursuing a skill that they had and then finding a way to make that valuable to other people. So not just following any passion but following, you know, the specific kind of passion that other people recognize as well.

You know, one of the biggest lessons was just helping people simplify. Because if you haven’t started a business before, you feel like it’s this really big thing, kind of like changing the world, and you imagine writing a business plan of like 60 pages or more. Because if you read most books, that’s what they tell you to do. And if you talk to a banker, that’s what they tell you to do. But that’s not how most small businesses are started. A business is simply a product or a service. It’s something that you make or offer. It’s a group of people who are willing to purchase that or otherwise exchange money for it, and it’s a means of getting paid.

So, it’s a PayPal account, essentially. And PayPal is now in, I think, more than 150 countries. So almost anyone listening to this or reading this interview should be able to have a means of getting paid. Almost everyone has something that they can offer to the world, some kind of…something kind of skill or knowledge that can be transferred into a product or service. And then it’s a question of finding the right people.

So, in “The $100 Startup,” there’s a one-page business plan, which if you don’t have the book, you don’t have to buy it. You can get the one-page business plan for free on 100startup.com. And there’s lots of other resources that kind of show exactly how people have done this in different ways. But the other thing I’m a big fan of encouraging people to do is to start quickly, to start within 30 days or less. So really try to figure out, okay, what is it that I can create and offer? How can I make a really simple website and get it up? It’s okay if it’s not, you know, gonna win some design award or something. It’s okay if it’s not super successful because it’s not gonna cost a lot of money, but hopefully I’m gonna learn something from it.

And a lot of the stories that we looked at, not only did they learn something from it, but they actually did make a lot of money, you know, right from the beginning. So, those are a few of the first things I think of.

Nathan: Awesome. And can you tell us the components about what you believe it takes to build a successful business?

Chris: Ultimately, it takes convergence, which is what we’ve been talking about a little bit in this interview in some different ways. It’s about saying, okay, here’s…if you make a list of all the things that you’re good at, all the things that you like and that you like spending your time on, and then think about, okay, what are the things out of this list that other people are also interested in? How can I make this valuable and interesting? There’s a lot of stories about people who’ve created different kinds of information products by helping people to be educated about certain things. There’s a story in the book about a guy in California who wrote an eBook about Evernote, the free software. You know, just helping people to use this software. No one had ever done this before. He wrote an eBook. It took him a month or two, and it ended up making more than $100,000 over the first year.

Now, he made a great product. You know, he spent a lot of time compiling the information, but ultimately, he provided something that he was really passionate about. He loved the software and was a geek for Evernote. And other people also were using this but there was no one helping. So he did that.

You know, in some of the travel hacking stuff that I do, no one ever pays me to travel. I’m just a traveler. But when I found a way to say, okay, you know, I’ve had a lot of experience going to places without spending a lot of money, maybe there’s a way I can document that and offer that to people who have the same need. That’s when that business became successful. So it’s about focusing on something that you love but that other people are willing to pay for.

Nathan: Love it. Awesome. So, look, we have to look at wrapping things up. So, I’m gonna ask you one question that I ask every single person that I interview and share their story in the magazine, and that is, do you have any final words of wisdom? Or is there a question that you wanted me to ask you but that I haven’t asked you yet that you wanted to share?

Chris: Yeah, no, I wasn’t prepared for final words of wisdom. My whole life has been just a process of trying things and seeing what works, and some things don’t work, but I don’t worry about those things. I keep focusing on what does. You were kind enough to say some nice things about this whole project, The Art of Non-Conformity and everything else. But all of that, you know, if you go to read the beginnings of the blog, you’ll probably see that it’s not very good. And I always encourage people to do that. Because if you look at someone who is a little bit more successful or maybe they have more platform or whatever it is you’re trying to achieve, you can feel intimidated.

But you should go back and see where they started, and you’ll probably see the whole process of how they built that and the mistakes that they made and the things that they did well. So I guess all I’ve done is I persisted. You know, I believed in this, and so, I kept going. And so, I would encourage people, if you find something that you believe in, then you should keep going.

Nathan: That’s awesome. The quote, “Eighty percent of success is showing up,” from Woody Allen.

Chris: I agree. Like I said, it sounds kind of like a cliché kind of thing, but a lot of people don’t show up. So if you show up, you’re ahead of 80% of them.

Nathan: Awesome. Well, look, Chris, I really appreciate you taking the time, and I feel honored to be speaking with you right now. So, thank you very much.

Chris: Cheers, man. Thank you.