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Season 02, Episode 13

The Process of Building a Side Hustle

with Author & Side Hustle Expert, Chris Guillebeau
Podcasts

In this episode, side hustle master, Chris Guillebeau, and I talk about the process of building a side hustle, what that’s looked like for Chris throughout the years, and how anyone is capable of starting a side hustle for themselves. We touch on what side hustles look like in the current economic climate and we also talk about Chris’s new book, The Money Tree, that was published on April 7th.

Chris is the New York Times bestselling author of The $100 Startup, Side Hustle, The Happiness of Pursuit, and other books. 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.

His daily podcast, Side Hustle School, is downloaded more than two million times a month. He is also the founder of the World Domination Summit, an event for cultural creatives that attracts thousands of attendees to Portland, Oregon every summer.

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Full Transcript

Chris G:

Like everyone's an expert at something that is kind of a core principle. I think of side hustling, everyone's an expert at something and it could be like some video game, it could be knitting, it could be some hobby that is very esoteric or random. But your friends always ask you about it or like you're really good at getting out of traffic tickets. A lot of successful side hustles are these really random kind of things, you know, like things that people haven't even thought about and ended up being like six figure business.

Chris R:

What's up everybody? I'm Chris Ronzio, founder and CEO of Trainual and this is Process Makes Perfect as always, we're talking with experts in process creation, automation and delegation. Basically the people that know how to make business easier. You just heard Chris Guillebeau and this episode is all about the process of creating a side hustle. Chris is the New York times bestselling author of The $100 Startup, Side Hustle, The Happiness of Pursuit Born for This. And his newest book, which comes out in April called The Money Tree during a lifetime of self-employment that included four years as a volunteer aid in West Africa. He visited every country in the world before his 35th birthday. That's 193 countries. He's the host of the side hustle school podcast, which is a daily podcast, downloaded more than 2 million times a month and I've gone to his events, the world domination summit. I've read his books and this guy has been hugely influential for me, so I think you're going to love this.

Chris R:

What I really liked about this episode is that Chris takes us behind the scenes on the podcast, on the events, and on his process of making books that have turned him into the thought leader that he is, and he'll share tips on how to develop your own side hustle. When he was getting started, he had to cobble together that income to afford him the ability to travel around the world. So whether you work for a company or you're trying to start your own, I think you'll find his tips really helpful and a process to get started is in this podcast. I hope you enjoy it. 

Chris R:

Welcome to Process. Makes Perfect. I'm your host, Chris, Ronzio, and as you heard in the intro today, we're talking with Chris Guillebeau. Chris, thank you so much. Welcome Chris. Thank you so much. This is easy. Chris and Chris, I won't mess this up. So today we're going to talk through a few things we focus on process in this podcast. So we're going to talk about the process of building side hustles, which I think could be more important than ever right now and the process of building communities, which is also probably more important than ever. So I don't know if you want to give us a brief background, if we should just dive right into it. Why don't I start. The first thing I ever read of yours was a manifesto you created called a brief guide to world domination, which is the best name ever. I would say very modest title. So I picture it being like a Jerry Maguire kind of moment where late at night you pound it out. This whole manifesto. What was the actual story? What was the

Chris G:

Yeah man, I love talking about process. I'm excited about process. I'm like, I had this project of going to every country in the world, which is kind of connected to The Brief Guide to World Domination. And for me, like I spent 11 years doing that, like trying to visit every country in the world, which I did. And it was all about process. Like, it was like I was, you know,  I had to love the process. I think if anybody did it and didn't love the process, that'd be very difficult, you know? So I've been thinking about that for a long time and with Brief Guide to World Domination, the process for that was like, well, I think I have something to share. This is going back 11 years now. I think I have something to share. Um, you know, I've, I've been an aid worker for four years.

I've got this quest to go to every country I've been an entrepreneur. Um, but what, what is my message basically? And so started crafting like all these notes about what became the art of non-conformity, uh, my original blog under the tagline of you don't have to live your life the way others expect. And so the, the brief guide did not domination was kind of like a compilation of like some of my experiences from other people's experiences around that time and just kind of offering a different way to see the world. Um, and that it's, it's cool that you read that because that is, like I said, going back quite a ways. Um, but it's, it's what allowed me to kind of start doing what I'm doing now.

Chris R:

So when you think about the process of visiting every country and as you were writing that book, you were an aid worker. How'd you afford to visit every country? What were the logistics?

Chris G:

Absolutely. Yeah, so I mean, I've written quite a bit about this. Um, I did a whole book called the happiness of pursuit, which was, you know, a little bit of memoir of my journey in quest, but also like the global story of quests. I'm like, why do people do that? And you know, what did they learn? What did they sacrifice and such, but to try and give you like a direct concise answer. So the first 100 countries cost about $30,000. And when I realized, yeah, exactly, that was my response. Like when I actually realized like I was an aid worker for awhile, like I said, four years in West Africa, I just kind of naturally had traveled to like 30 countries. Um, by the time I was like 25 or so. And so I started by setting a goal of going to a hundred countries.

And that's when I added up the difference between what I had been to them and like a hundred. I was like, it's gotta be like $30,000. Then I was like, man, you know, people, I wrote about this too. Like people are buying SUVs, you know, back home, you know, at the time that cost $30,000 easily and cool. You're like nothing. I'm not saying people shouldn't buy a nice car or whatever, but for me, I was like the value of, you know, being able to go to a hundred countries, like that's, you know, immense. And so after a hundred countries, and I was like, let's go to every country in the world. And at that point I kind of had a career, you know, attached to it. I was writing books, I was doing little businesses and such, I don't know the exact cost for that final hundred. It was more than 30,000, I'm sure. Um, but it's not like an astronomical amount of money. I mean the biggest challenge was not money. It was logistics basically. It was process essentially.

Chris R:

Yeah. The first thing you said on here was, you know, when you have these big goals, you've got to love the process if you're going to accomplish those things. So you must've loved it. So did you have, did you have side gigs or side hustles through, through that to be able to fund your travels?

Chris G:

Yeah, so let's go back. So let's say like age 19 to 27. Basically I never had a job. Like I was always working outside the formal economy. I'm learning to sell stuff on online auctions. When those first came out, ebay.com was this cool new site, you know, back in 1999 basically. And I, um, you know, started by selling stuff around my apartment and I learned to like buy coffee and Lego and video games and other stuff and resell it. And it's not like I was getting rich, but it was really exciting because I was like, wow, I'm 19 years old and like, you know, the last job I had was paying $8 an hour and I'm making like a $10 an hour without even knowing what I'm doing, you know? And like if I get better at this I'll, I'll make more but not just so I can make more money.

It's like this is the key to freedom. Like this is the key to like a life that I want to live on my own. So I mean from there I learned about a lot of like internet marketing stuff and like building websites and affiliate income and Google AdSense and information products and all this stuff, but eventually kind of like coalesced into, okay, I'm going to write a blog and go to every country in the world and I want to write books. And that was my ambition at that point. Like age 30. Um, I had, you know, came back to the States from being overseas, um, and did grad school and with like, okay, what's next? And I had the choice to either do a PhD program or um, you know, kind of go all in with a blog and I'm so, so, so glad that I was actually rejected from most of the PhD programs I applied to. And I cannot imagine an alternate reality, uh, in which like I was accepted and I went, you know, like I'm really, really glad for that.

Chris R:

So. All right, so you, you built this, this business and this life for yourself, writing and doing your blog and you had other businesses too, like, uh, the travel cartel and was that all during the same time?

Chris G:

Yeah, I mean it's all a little bit kind of like, you know, mixed together. I mean, like that membership side, travel cartel, um, I started that, I don't remember exactly the year, but it was after I had been blogging and I did that for like five years now. We eventually just kind of like retired. It sunsetted it and I mean it had lots of little little project of business called unconventional guides. It was like information publishing and such. And I mean I, I was never good at like scaling a business, you know, I was never good at like this whole like model of um, you know, creating a sass or whatever. Like for me was, it was very much like how can I create a liar, a lifestyle that allows me to do what's important to me and contribute meaningfully and not be dependent on anyone else for my income and my wellbeing.

And I mean the, and like right now obviously like people are asking themselves like, how can I not be dependent on the corporation, on the government, on like I have to be able to provide for myself. Even if you have a job, even if you have a good job that's cool. Like it's fine. But like what if you didn't have that job? You know, what if you didn't, what if next year you don't love that job anymore? What if something changes? So like I always, I was very attracted to that value of self reliance. And for me it was like, how can I express that and then hopefully pass it on in some way to others.

Chris R:

Do you think that everyone could have a side hustle or is there something innate that people need in order to pull it off?

Chris G:

I don't think there's anything in Nate about it, man. I think like, you know, I used to live in West Africa and like every person in the world there, every person in the country has a side hustle. Like you can't live in that. Lots of countries in the world without doing something to make your own way because there's not much of a formal economy. There's not like LinkedIn, you know, in the village in Sierra Leone or, um, so I would never say it's easy. I never want to be like, this is the get rich quick plan or anything at all like that. But do I believe that everybody has something within themselves that they can offer to someone else, you know? And can they learn the very basic business skills of creating a product or a service? Yes, of course. You know, and not only can they, but I think, I think most people probably should.

Chris R:

So since this is a process show, I've gotten asked those questions too from people that say, I want to start something, I don't know what, what to start. What would be the step-by-step sequence that you would tell that person to figure out how to make money for themselves?

Chris G:

Yeah, I mean, so it's usually like a little bit of a back and forth interview. Right? And so we can't obviously interview every single listener who's, you know, part of this conversation. But what I would say, like, the first thing I would say to them is, okay, well let's, let's talk a bit about your skillsets. Um, which is quite different from saying like, what are you passionate about? You know, like, what do you like to, I don't, I don't usually start with that. It's like, what are you good at? And some people you know have an answer for that. Other people are like, well I don't actually know what I'm good at in terms of, you know, making money or in terms of being marketable. And so then you have to unpack it a little bit because, you know, I think some people think I'm only good at something from my career.

Like I was trained in this kind of engineering or this kind of software development or firefighting or you know, whatever it was, but I don't know how to take this skill and apply it in the new economy. And that's essentially what I'm trying to help people do is like, okay, so you got your education, you've got your work experience, you've got the things that you're an expert in. Like everyone's an expert at something that is kind of a core principle. I think of side hustling. Everyone's an expert at something. And it could be like some video game, it could be knitting, it could be some hobby that, that, um, is very esoteric or random. But your friends always ask you about it or like, you're really good at, I don't getting out of traffic tickets or you're like, I a lot of successful side hustles are these really random kind of things, you know, like things that people haven't even thought about and ended up being like six figure businesses. 

So then it's like how can we go from your, like your skillset to your idea and then from your idea to an offer because everybody has ideas. You ask the average person on the street, like you have a business idea. Oh yeah, I got this idea, you know, but nothing's happening with it. And so, I'm trying to help people, like, what is your product? What is your service like, how has this idea offered to the world? How can I as a consumer give you money for it? You know, where do I go to do that? What's your Venmo, your PayPal, your website, you know, your shopping cart. So I'm trying to get people like nuts and bolts. Um, so I think it starts with that skills, idea, offer, product, service, you know, then launch.

Chris R:

Nice. So I remember another book of yours I read was the $100 Startup, which was kind of like the playbook for this, right? So if, if people are going through that, didn't it have kind of the sheets that you could fill out to craft your offer?

Chris G:

Yeah, that was a very how to driven book. Um, and also a Side Hustle, um, provide you the income in 27 days. That's a very process driven book. Um, which is good. And like I'm a process oriented person as we said. I just have learned a little bit like the new book, the money tree is a story and I'm trying to teach to a story. So there is still a process there, but it's not presented in a didactic form. It isn't, it's not like step one, do this, step two do this. I think in some ways, we actually learn more from, from stories and we retain more information from stories. Um, so you actually might learn more from, from, you know, reading that than you would from reading the checklist or whatever. Like I like both of course, but if I think back about like, think about songs that you heard as a kid, you can sometimes remember the entire lyrics, you know, to these songs, right. Because it's a, it's something that's different than just like a how to, you know, a process driven thing.

Chris R:

Gangster's Paradise by Coolio.

Chris G:

Yeah. Right. Live in most of our lives. Right. And then also the know what's the other parody of it. Right. I forget that. That one then paradise.

Chris R:

Weird Al. Yeah. Okay. So, as the, as the side hustle expert, you also have a podcast called Side Hustle School. So how long have you been doing the podcast for?

Chris G:

I've been doing it for 1,153 days approximately. I started at January one 2017 and doing it every single day since then. Um, and uh, every day for the first three years, every day I told a different story. It was all case study model. It was extremely processed. It was like, this is this person, this is Chris over here from so-and-so. And like there was his idea and here's how he made it happen and here's what tripped him up a little bit. Here's what he got wrong, here's what you got right. You know, here was the outcome 10 minutes a day, like really short because trying to make it for, you know, busy people, right. Busy people who actually have jobs and don't have time to listen to like super long stuff, you know, all the time. And now I'm doing a, I'm still doing two stories a week, but rest of the time I'm doing like question and answer from listeners who are launching their projects. It's really cool because, um, I, I committed to doing it for a year and then just kinda kept going because now a lot of the stories on the program are coming from listeners who've been listening in like year one and year two and like they have started their project. And, um, so that's really fun. I like that.

Chris R:

Yeah. And the format is different too, because you're reading these stories. So it's not necessarily an interview format, it's more curated and it's easy to listen to, which I like. So definitely check out the podcast if you haven't already. Now in this kind of coven 19 era that we're living in, that we're recording this. And what, what do side hustles look like today? Is there any recommendation you're making?

Chris G:

My recommendation is to, um, embrace the uncertainty and to get comfortable with being uncomfortable. And you know, if this sounds like too philosophical, like I assure you, it's very practical. Like it's meant to actually be like very, like, how can I, you know, uh, how can I apply, you know, what's happening essentially? And so I always have to be careful when I talk about this cause I want to just say like, I'm not, you know, making light of something that is extremely disruptive and obviously damaging, you know? Right. Um, so that's, that's that, but it's not like I'm saying there's a silver lining. It's more like also in addition to like the destruction and the disruption. Um, you know, systems are being changed, all kinds of people are working from home, uh, who have never done that before. I hear from a lot of people that I have wanted to work remotely.

Um, and their boss has always said no, you know, or whatever. Like now here's our chance. You know, and people are also having to like learn new habits and your rituals and your routine. I'm hearing from a lot of people that are actually like, I'm actually working on my side also during the day now and I wasn't able to do that before, whatever. So I think um, there's always like winners and losers in the marketplace for you know, anything like that. The most obvious thing is like, don't you wish you could go back in time and like start that hand sanitizer company that you dreamed of as a kid. You know, like that's like, that's like super like, you know, obvious but also like people are looking for security, they are looking for assurance, you know, they are looking for community. Like you mentioned that at the beginning.

Like I think actually now more than ever people need community because like we're stuck in different places and we're taught to kind of be afraid of people. It's like that's not what it's said, but that's kind of what's implied. And um, so like it's, it's a certain, it's disturbing to the psyche. It's to serving to like society. Um, but hopefully you know, out of it will also come a lot of stories that people that are like never would've done this if it hadn't been for this. Cause I get a lot of that stuff. You're like in $100 startup. Like the whole book begins with this guy who's like open this mattress store and he was a retired or he was a laid off advertising executive and had been doing advertising for 20 years and now he's like this entrepreneur, it's actually a seven figure business now. And he said, I never would have imagined in a million years I was gonna open like a retail store by, you know, I kinda got pushed and that led to something different. 

Chris R:

that's amazing. Well, even in the, yeah, and even in the right now I saw a story that's I think local. Do you, are you, are you in the Portland area? Is that right? So there's a distillery, I think in the Portland area that started making hand sanitizer. Did you hear about that?

Chris G:

Right. They already have a good business model now without doing that, you know, it's right this time making the gender or whatever. But yes, that's, that's pretty cool. I didn't see that.

Chris R:

Yeah. And so the exposure that they're getting, the presses almost like another kind of currency that you know, you can do. So. So that's kind of a good shift, I guess, into community building. You know, you started this, this whole journey, you said 1112 years ago, and you've built an amazing following and published books and you've got this World Domination Summit that you've put on every summer, right. And, and there is a incredible community behind you. So do you think it was right place right time that you started the thing or do you think it's something anyone can do even today?

Chris G:

I mean, there's always the right place and right time element to any success. You know, I think anybody who says like 100%, I built everything myself. You know, you're like, well, you probably had some good, you know, you had some good chances as well. And, but it doesn't mean that they don't work. It's like the whole thing about luck is like, you know, to be lucky or take more chances, right. To be, you know, to be, you know, to be more fortunate, like more, you know, swings at the bat or whatever. But so I'm sure there is like timing to it, but for me it was, I do believe that now more than ever, people are looking for connection now more than ever eCommerce is like widespread. Like it's not just mainstream, it's everywhere. You know, it was a lot more unusual when I started doing stuff 20 years ago.

Um, everybody has a PayPal or Venmo account. If you walk into every coffee shop, lyou know, it was like a lot of people, they're just kind of working on their side hustle, which was also, you know, everybody thought you were on drugs or like you were selling drugs or like porn, like they thought there was only two internet industries that existed like 20 years ago. You know, probably kind of shady about it actually. And now it's like everybody does it. So I think there's always times when some one thing is easier, one thing is harder, but, so those specific things change over time, but the chance to put forward a message and connect with people, like that's always there.

Chris R:

Yeah. Well like you said, people could embrace this, you know, this is the time where I'm seeing a lot of virtual events popping up, so it's even easier to do those types of events, so, so may make it happen, I guess. All right. So I guess to wrap this up, you've got a new book that is, did it just come out or it's coming out the money tree?

Chris G:

Yup. Yeah. Well depends on when people are listening to this. A publication date is April 7th. It's called The Money Tree. A story about finding the fortune in your own backyard.

Chris R:

I love it. And what, what can people expect to get out of that book?

Chris G:

Well, they can't expect, first of all to enjoy the story. It's a story of this young guy who, you know, has a good job and is a hard worker, but has a lot of student loan debt, like so many people these days. Um, and he's kind of really, it's actually affecting his entire life. Like he has a lot of debt. She's getting kicked out of his apartment, it's affecting his relationship, all that kind of stuff. And he realizes that he can't just work harder. He can't just like, he's already doing a good job. He can't just start driving for Uber. That's not going to solve this problem. He has to do something different. And so he goes on this exploration of first learning to resell stuff like his, his college textbooks, and it gets a thousand dollar challenge. Like somebody is like, can you make $1,000 in the next week?

And he's like, well if I knew how to do that, I wouldn't be in this problem. And they're like, we'll just try. And so we kind of has to work that out and then he starts a service business and you know, a lot of different stuff happens along the way. But I think they're going to learn through that process. They're going to learn. Like there is something that I can do and my hope is always like with all my books, whether it's the how to books or like this book is that people will finish the book and not just say like, Oh that was a cool book. You know, like that's nice to hear. But I'd rather hear you're like, Oh this is a good book. And it got me thinking about something and then I went and like, you know, got online and started my thing. Or you know, I don't know, whatever it is, I helped them take action. That's what I hope it will help.

Chris R:

Absolutely. Well your books have done that for me. So I'll say thank you on behalf of all the listeners. It's, you know, it's funny that $100 Startup book, I already mentioned it, but a friend and I actually booked a hotel room, read the book and started a business that night and we had a sale within eight hours, which was pretty cool. So back in the day and you tweeted me back, so you've had an influence on me, so thank you for that man. That's awesome. So as we wrap this up, um, we do this thing called the double tap. Like if we were to just double, double click, double tap on you. A couple of questions, rapid fire, just tell me whatever, whatever comes to mind. Uh, all right. So first, what is a brand that you think has perfected its process that you admire?

Chris G:

I was just hanging out with Donald Miller, who's the CEO of StoryBrand. He's also an author and he's just done an amazing job with helping businesses reduce confusion, which is a huge problem. So StoryBrand, he's like super invested in process and logistics and I just soaked so, so good. I'm just so admiring of him. StoryBrand,

Chris R:

who is someone who's coached or mentored you?

Chris G:

I'm not super into mentorship. Um, but I have, it doesn't mean I have to learn. No. Yeah, I mean I think everybody has the power within themselves to learn stuff and like, um, but it doesn't mean that, it's not to say that you haven't learned from people, right. It's like, it's just kind of like a nuance thing. So, um, Jonathan Fields is a good friend of mine. I learned from him all the time. He's the founder of Good Life Project, which is also very popular podcast and um, except this new like personality test called spark a types. And I learned from him all the time, but I also like, I also want to say I learned from my community. I learned from just all the people out there that are like tweeting or sending emails. Like, no, that's who I've always tried to be focused on them as opposed to focused on like, who is like above me or next to me or anything like that.

Chris R:

I love that. Okay. Um, your favorite book or podcast other than all of your own?

Chris G:

I'm giving all these long form answers to your quick question. Sorry. I need to like pick it up here. You know, a podcast. I like reply all. I like happier with Gretchen Rubin. I'm going to go with those to reply all happier with Gretchen Ruben.

Chris R:

Okay, great. Most entertaining person you follow online.

Speaker 4:

Okay.

Chris G:

Most entertaining person. Uh, okay. Who is really good with stuff? Um, Johnny [inaudible], he does a great job

Chris R:

and one app you can't live without.

Chris G:

Alright. OmniFocus. I'm going to go OmniFocus. I use that for all my, my tasks and like, it's actually opening another window while we're talking here. It's like when I finished this conversation, here's what I'm going to do next. All my projects on my task gotta use that

Chris R:

Focused. All right, so everybody that didn't know you before this now knows that you're focused, you're process oriented, you've built a community, you've written dozens of books, probably a soon to be dozens. But is there anything else you want to leave people with other than to go by the money tree?

Chris G:

Uh, no. That's great. Wonderful conversation. Uh, yeah, check out the money tree. Let me know what you think. Um, if I can help with anything. Uh, yeah, just give a shot.

Chris R:

Amazing. Chris, thanks so much for your time. We appreciate it.

Topics Covered

  • Chris’s manifesto, Brief Guide to World Domination 
  • Spending 11 years visiting every country in the world and loving the process
  • Chris’s early side hustles that funded his travels
  • How anyone can have a side hustle and should
  • Focusing on your skillset vs what you’re passionate about
  • The Side Hustle School Podcast
  • Should you start a side hustle during the current economic climate?
  • How side hustles have evolved over the years 
  • Chris’s new book, The Money Tree
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