in: Career, Career & Wealth, Podcast

• Last updated: September 30, 2021

Podcast #344: The Art of the Side Hustle

If you’re looking to pay down debt or save for a financial goal faster, there are two ways to to do it: either save more money or make more money. Let’s assume you’re knocking it out of the park with your frugality. How can you make more money? Well, one way is starting a side hustle. Besides providing you with extra income, my guest today argues that having a small business on the side can actually bring a lot more satisfaction and confidence to your life. His name is Chris Guillebeau and I’ve had him on the podcast before to discuss his book Born for This.

Today on the show Chris and I discuss his latest book, Side Hustle: From Idea to Income in 27 Days. Chris and I begin our conversation talking about why every man should have a side hustle — including those who are already very happy with their day jobs. Chris then walks us through the process of starting a side hustle from ideation to business formation to marketing. Along the way Chris busts some myths that people have about starting a business and provides examples of folks who have added $1,000 to $20,000 a month to their income with a business they work on in their free time. 

Show Highlights

  • What is a side hustle?
  • Why everyone should have a side hustle
  • Why it’s beneficial to do something rather different from your day job with your side hustle
  • How to go from an idea to making money in less than a month
  • Coming up with an idea for a side hustle
  • How to test your idea with $10 and a Facebook account
  • My own experience with side hustles
  • What makes for a successful side hustle
  • “Starter” ideas vs. “Next Level” ideas
  • How to make money even with saturated markets and ideas
  • The infrastructure you need (or more appropriately, don’t need) to start making money with a side hustle
  • How the Art of Manliness started as a side hustle
  • How to effectively market your new idea
  • What to do if your side hustle is a flop, or if it’s just a mediocre success
  • Defining your side hustle goal
  • The viability and desirability of having more than one side hustle
  • What Chris learned from his own side hustles
  • Using side hustles to teach your kids about entrepreneurship

Resources/People/Articles Mentioned in Podcast

Side hustle book cover, written by chris guillebeau.

If you’ve been looking to start a side hustle to earn a bit of extra cash, I highly recommend this book. Very actionable and practical. Be sure to check out Chris’ Side Hustle School podcast as well for real-life case studies.

Connect With Chris

Chris on Twitter

Chris’ website

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Read the Transcript

Brett McKay: Welcome to another edition of the Art of Manliness podcast. If you’re looking to pay down debt, or save up for a financial goal faster, there are two ways to do it. Save more money, or make more money. And let’s assume you’re knocking it out of the park with your frugality, you’re saving as much as you can. How can you make more money? We’re talking legally here. Well, one way is starting a side hustle. And besides providing you with extra income, my guest today argues that having a small business on the side can actually bring you a lot more satisfaction and confidence to your life. His name is Chris Guillebeau, and I’ve had him on the podcast before to discuss his book, “Born for This”.

Today, on the show, Chris and I discuss his latest book, “Side Hustle: From Idea to Income in 27 Days”. Chris and I begin our conversation talking about why every man should have a side hustle, including men who are already very happy with their day jobs. And then Chris walks us through the process of starting a side hustle from ideation to business formation to marketing. Along the way, Chris busts some myths that people have about starting a business, and provides examples of folks who have added $1,000 to $20,000 a month to their income with a business they work on in their free time.

Lots of actionable advice in this show, and after it’s over, check out the show notes at hustle where you can find links to resources, where you can delve deeper into this topic.

Chris Guillebeau, welcome back to the show.

Chris Guillebeau: Thank you for having me back. I think it’s like the seventh or eighth time I’ve been on the show, not quite seven or eight, but it’s a big honor.

Brett McKay: Yeah. A threepeter ’cause you’re always coming out with these books, so I gotta have you back on the show. You know, last time we had you on the show, we talked about building your dream career. And we got a lot of positive feedback from that. You’re new book is called “Side Hustle: From Idea to Income in 27 Days”. We’ve written about side hustles on the site before. We’re a big proponent of them. For those who aren’t familiar with the concept of a side hustle, how do you define a side hustle?

Chris Guillebeau: You know, a lot of people are talking about side hustles in a lot of different ways, and I’m glad to hear that you had some good feedback from our last conversation. I actually feel like this new book, Side Hustle, is probably the most relevant to your listeners that I’ve ever written. And I’m trying to focus my side hustle focus, or my side hustle push, on creating assets, on creating something that you have ownership over. And the reason why I’m doing that … well, one, it’s just smart. But then, also, I feel like in the culture some people are talking about side hustles as part of the gig economy, or as part of the notion that people have to have two or three jobs these days.

And I’m not really trying to encourage people to work harder, or to do a 40 hour a week job and then go and do a 20 hour a week job somewhere else. I’m trying to help people create something that they can point to and say, “You know, I have ownership over this thing and it’s making money for me. And maybe I never wanted to be an entrepreneur. Maybe I still don’t wanna be an entrepreneur. But it’s really great that at the end of the month, I can have my paycheck and I can have this extra income coming in. And that just feels really good.” So that’s what I’m trying to help people with.

Brett McKay: So, there’s a lot of reasons people start side hustles, and I think you argue that everyone should have a side hustle, even if you got a satisfying career, you love your job, you should still have something on the side. Why is that?

Chris Guillebeau: You know, I’ve never felt more strongly about something I think, and about this concept in particular because I am not trying to encourage people to go out and quit their jobs. I did that a little bit with the previous book, “$100 Start-up” that I wrote, and kind of learned through that process. That book resonated with a lot of folks. And a lot of folks said, “well, that’s not really me. I actually love my job.” Or “Maybe eventually I wanna quit my job, but I can’t do that right now.”

I think everybody needs to have more than one support in their life. I think it’s smart for everyone. I think it’s good to have a back up plan. It’s good to have more freedom. There’s really no downside to it. I feel like if you invest in this process the right way. And by invest, I’m talking mostly about your time, not talking about spending money, then I feel like only good things come from it. And like I said, it gives people confidence, makes them feel empowered and, of course, it’s extra money.

So, you know, one way to look at it is like, “Oh, look at what’s happening in the world, in the economy, and people don’t have security in traditional jobs.” All that is true. I agree. The other way to look at it, in addition, is to say, “Well, this is something that’s creative, empowering, makes you look at it and say, like I mentioned, I made this thing. I own it.” And it also can be fun. It can be something that you look forward to doing. It’s not something you dread. It’s something you look forward to doing at the end of the day, or the 20 minutes in the morning, or whatever time you have for it.

Brett McKay: Yeah. I think that last point is a good one, because a lot of people who … they might not hate their job, but it’s not giving them the creative outlet that they might … are desiring. A side hustle allows them to do that and also make money in the process.

Chris Guillebeau: Yeah, yeah, yeah, exactly. I talked to a guy last night. I’m on this tour to do 100 cities, talk to people about side hustles, and I generally think it’s good to do something a little bit different for your side hustle than you do for your day job. And I did meet someone last night who was like, “Oh, I’m a web developer by day, and I’m a web developer at night.”

That can work. I mean, some people do that. What I tend to see people just having more enjoyment with and maybe even more success with is something that’s totally different. So, there’s a story I did recently about a guy who’s a manager and his side hustle is producing poetry slams. And he makes $1,000 a month putting on these poetry slams, which is great ’cause you never hear about a poet making money. Right? But then, also he’s the accountant by day, poet by night, so totally different kind of thought process and work and creative outlet, like you said.

Brett McKay: What does it take to start a side hustle? Does it require a lot? ‘Cause I think a lot of people … ’cause it’s a business. Right? So I think people think, “Oh. There’s a lot of hoops I gotta jump through.”  What does it actually take to start one?

Chris Guillebeau: Right. Right. It basically takes … It takes all your life savings, and you need to go back to school for four years, and … yeah, no, it takes none of that. What I’m trying to do with the book and the tour … show people this process and the process is idea to income in 27 days. So, I really am encouraging people to get this thing started quickly. And, as I said, it’s not about spending money. It’s also not about this extensive planning phase as well. So, basically what it’s about is helping people use the skills they already have to create some kind of product or service. And I think that’s key because people tend to think about “business ideas” and people, consumers, all of us … we don’t buy ideas, we buy products or services.

So, I’m helping people look at the skills they have and figure out …How can I package that into some kind of product or service? How can I then turn that into some kind of offer? And then, how can I get that out to the world, probably before I’m ready? So that I can get some real world feedback, not just asking my buddies like, “Hey. What do you think of this idea?” … but putting it out and seeing how people really respond, and then kind of regrouping from there.

So, 27 day process, it’s broken out into like five weeks. You do one thing a day, as I said, 20 to 30 minutes a day. And, at the end, you should have some real results. And you should be able to actually point to something and say, “Look. That’s my side hustle.”

Brett McKay: So, let’s talk about the ideation process. Where can people get ideas for side hustles? ‘Cause a lot of people say, “I wanna start a business but I don’t know what to do.” So, where can people find these ideas?

Chris Guillebeau: It’s really interesting. I’ve learned through a lot of research and eight years of working on this in different ways that half the people struggle with that, what you just mentioned … Where do ideas come from? I don’t know what I have is a good idea. The other half of people struggle with … I have an idea. Ideas aren’t my problem. I just don’t quite know what to do next. Or I can’t choose between different ideas. So, the first part because the book goes through for both sections.

So, learning where ideas come from is essentially a skill that nobody really learns in school. Your parents didn’t teach you. But it’s not that hard to develop. So, it’s just essentially about developing your skill of curiosity, or developing the power of observation. And just beginning with paying attention. So paying attention, first of all, to daily life. As you kind of go through the world, looking around and noticing things that you like, but what things do you not like. And what frustrations do you encounter? What problems do you encounter? How could somebody create some kind of a solution to something?

The second part is also then looking at yourself. What are your skills? What are all your skills … not just skills that you use for your day job, or what you got your degree in if you went to college? But what is something that we can actually combine with these two thing? Your skill, your background, your interests, and then also some kind of problem in the world or something that can then turn into, as we said, a side hustle. So I try to walk people through all these different examples of, okay, here’s how this person did it. And hopefully that gets you thinking ’cause you’re not gonna do the same thing that they did, or that I did, or anybody else, but through this process hopefully you can get the ideas that you need.

Brett McKay: And say you get some ideas. How do you determine if it’s feasible? Right? ‘Cause you might have this idea. You think it sounds great on paper. But then, actually I’m gonna lose money trying to make this a business. How do you figure that out before you make too much of an investment of time or money into it.

Chris Guillebeau: Sure. Well, I’ll say two things about this. One, to your direct question, there is a process that I show in the book about how to test your idea with $10 and a Facebook account. And it’s this really process of basically writing an ad and just kind of seeing how people respond. It’s not that difficult to set up, and as I said, it costs like $10. However, I’ll also say that I have this daily podcast called “Side Hustle School” and every day on the show, seven days of week, I have a story of somebody who does this and so telling a story of an employee who starts an income generating project without quitting their job. How’d they get the idea? What happened? How’d they develop it? What challenges did they encounter? How much money did they make from it? And what I have seen is that it’s actually not always possible to know in advance if this thing is going to work.

It’s not possible, not always possible to know if your ideas is going to be validated. And so, sometimes you just have to … you’re just gonna have to try. And that’s why the process is short. That’s why it’s 27 days, so that you’re not investing a huge amount of time or expending a year planning something that you don’t know if it’s gonna work or not. So I like to feature a bunch of quirky kind of different stories. The book begins with this guy who wrote a blog about fish tank reviews. And he was really into fish. And so, he spent a weekend, a short period of time writing these fish tank reviews and linking to Amazon, where he had a affiliate account, which anyone can create.

Then, he kind of went away and didn’t really think much about it. And a month later he got a check for $300 in the mail. And he’s like, “Oh. Okay. That’s interesting.” And so, he put a little bit more work into it, but eventually kind of left it because he was a construction project manager and a busy guy. So the short version of the punch line of that story is this was like three years ago, and three years on, like literally every single month, he’s been getting a check in the mail from Amazon for $700. So, $700 is not necessarily a life changing amount of money. You can’t live off of it. But it’s very significant, especially for something that you don’t do anything for. Right?

So, he’s been able to take his wife on extra vacation every year, and do all this kind of stuff. If you had tried to validate the fish tank review idea, before he started, I don’t know if you could. I think a lot of people would say that’s kind of a dumb idea. But, obviously it worked out pretty well for him.

Brett McKay: Yeah. $700 a month, that would pay for rent in a two bedroom apartment here in Tulsa Oklahoma.

Chris Guillebeau: Yeah. Right. Think about that. Yeah. Or help you pay off debt. I hear from a lot of people that have student loan debt, or credit card debt, or just whatever. It’s a real thing. And so, that’s why I actually, for the show and for the book itself, I have this minimum … you have to be making at least $500 a month to be featured on the show. Every story in the book … and actually my goal for people if you go through the book and you go through the process, I’m personally not gonna be satisfied, as the author, if the project you create is not doing at least $500 a month. And there’s a lot of stories in the book of people who’ve gone on to actually do six figure side hustles or much more. And I love those stories too.

We could get into those. But I think it’s also relatable in some ways to point to people who are like $500 and $1,000 a month.

Brett McKay: So, the idea is that a side hustle idea … you should invest so little into it, that it’s okay if you invest some time or some money because it’s so little that if it flops it’s not that big of a deal.

Chris Guillebeau: Yeah. Exactly. The risk is low. Right? And this is a counterpoint to traditional entrepreneurship because traditional entrepreneurship is all about … oh, you’re gonna take a big risk, you might get a big reward. You know, you’re out trying to start this start up or whatever it is. You know, maybe there’s this huge award that awaits on the other side but there’s also this huge chance of major failure. And I’m trying to take that huge chance of failure out of the process so that people can experiment and think of it like a hobby. It’s like a hobby. It’s something you look forward to, like we said. It’s something you enjoy.

Maybe you’ll spend a little bit of money on it, but you spend a little bit of money on your hobbies. Right? And this has the potential to be a hobby that actually pays you money. Right? So that’s the key to it.

Brett McKay: Yeah. I mean, here’s two examples from my own life of side hustles that didn’t cost me any money. One was a success. One was a flop. So when I … I used in Mexico for a few years, so I speak Spanish fluently. Well, not so much anymore. But, when I was in college, I offered tutoring services. So I just, all it is I printed off a little flyer and hung it up in where all the Spanish classes were at. And, it didn’t cost me anything … and within a week I had three clients paying me $20 a week for Spanish. And it took me 3 hours a week, and I was making $60 a week extra. It cost me nothing. The other side hustle that I tried was when iPods first came out.

And people … they had like these digital files, or they had CDs with all their music. And I tried to offer a service where I would rip their CDs and put ’em onto their iPod. I just printed fliers, and I hung up on doors. I spent maybe two hours and no money basically. And that didn’t go anywhere. I didn’t get any bites from that, but it was no harm no foul.

Chris Guillebeau: Exactly. Yeah. I mean, both examples, you printed some fliers, you know, like a small investment of your time, and one of them worked, and one of them didn’t. And you’re not … like I said, there’s no other start-up costs to that. None at all. So that’s good. Yeah. So, can I maybe make a quick comment on that first example. You know, there you’re obviously using a skill that you had. It was something that other people clearly needed and desired. They needed help improving their Spanish language skills. And then, in the second example, you thought there would be a need, or you wondered if there would be, and it turned out there wasn’t.

So, I had this concept of starter ideas and next level ideas in the book. And I think your example of the tutoring Spanish is a great example of a starter idea. And, when I say starter, it’s not any kind of negative context at all. It just means that it’s a fairly limited idea, in terms of the scope and availability of it because you can only tutor so much. People can only pay a certain amount of tutor … you can probably raise your rate at a certain point, but you can’t raise it indefinitely because eventually somebody’s just gonna go to another Spanish language tutor.

So, what I’m trying to help people do is definitely experiment with the starter ideas. That’s great. You can sell something on Etsy tomorrow. You can sign up for the platform Fiverr and offer some kind of service tomorrow. But the challenge there is you’re gonna be kind of locked into somebody else’s environment. You have to kind of play by their rules. They essentially can cap your income in some ways, just like driving for Uber or Lyft or whatever. So, next level idea is something that you actually do have this ownership over. It’s something that has the potential to earn a lot more money. So, very quick story about another guy who was also … he was actually trying to learn Spanish.

And he had lived in Argentina for a while, and had got somewhat proficient, but then he moved back to Canada and was kind of losing his skills. And so he downloaded an app. And he liked the app. I think it was Duolingo. He said it was good, but he’d also felt kind of impersonal. And then, at the same time, one of his buddies was also trying to brush up his Spanish, and hired a tutor on Craigslist, which is kind of like what you were doing. And he liked that process, but he was paying $25 an hour for it, so he thought this isn’t super efficient either. So, short version is this guy, I think his name is Sean, he created a platform that essentially allows Skype language lessons from people in the US and Canada, back with people in Argentina, or Chile, or elsewhere.

And so, then there’s an economic difference in terms of the cost, and people can log on at anytime. They don’t have to coordinate on meeting with Starbucks or whatever. So this project has actually super, super taken off. And within a year it’s actually more than $150,000 that he’s made from it. So, that’s kind of like the difference between a starter idea and something that could potentially go on to do much more.

Brett McKay: Right. The other idea. The next level idea that I thought was good was the Uber driver became an Uber driver coach, which was interesting.

Chris Guillebeau: Yes. Yeah, exactly. That’s a friend of mine named Harry Campbell, actually here in Southern California where I’m talking to you from. And it’s exactly what you just said. He was an Uber driver and was interested in learning more about how to do a better job, and how to increase his hourly rates, and get his rating higher, and stuff like that. So, he’s googling to try to find this information, feeling frustrated because there’s not a ton of stuff out there. And so, he decides to actually create this platform called “The Ride Share Guy”.

And so on this platform, which he’s now built out over I think about two years or so now, he has coaching sessions that he does. I think he has some kind of product. He’s also like speaking in the media about it. So he’s built this whole authority. So he went from driving for Uber, which is a good starter idea. You have some flexibility over your hours, et cetera. But, it’s also kind of limited because of competition and the rates are set by Uber, not by you. Now he’s gone to this thing that is more entrepreneurial in the sense that he can do whatever he wants. And he can take that in all lots of different directions.

Brett McKay: So, let’s say you narrowed on an idea. It’s feasible. You think you can make a good go at it. But in your research, you discover that there are other people who are doing pretty much the same thing that you’re doing. Right? Like that example of the guy with the app, the Spanish app. He was able to find a way to tweak that a bit. But let’s say there’s no way to tweak your side hustle. There’s a lot of dog walkers in your town. What do you do in that case? Should you go ahead, or should you just be like, “Okay. I’m gonna do something else.”

Chris Guillebeau: Well, I guess I would say to that example … are there a lot of dogs in your town? Because one dog walker can’t serve the whole market. And in a lot of way, seeing that somebody else is doing your idea is actually validation itself because you can see, okay, somebody’s doing this, they’re actually getting paid for it. I’m not reinventing the wheel here. But you don’t have to reinvent the wheel. You know, and most people aren’t going to. I feel like people are kind of obsessed with like, “I don’t have a side hustle idea because I don’t know how to invent the next iPhone or whatever.”

Well, you’re probably not gonna do that in 27 days, 20 minutes a day or whatever. So, I don’t necessarily think it’s bad that somebody else is doing that. Even like the language thing … let’s say that somebody else was doing exactly the same model that he was doing, there’s still so many people out there that want to learn Spanish, or you could choose a different language, or do it in a different way. So … not necessarily a bad thing.

Brett McKay: Yes. And I … there’s a disadvantage to being the first mover.

Chris Guillebeau: Yeah. Because then you have to essentially educate people on, you know, why they need this thing that they’ve never heard of before.

Brett McKay: Let’s say you get the idea. What do you need to get started? ‘Cause I think … going back to the idea people think they need to do a lot. Like they have to get business licenses. They need to incorporate to have a business. They need a business account. They need cards. What exactly do you need to have sort of legally, through the back of the structure, to get a side hustle going? Or do you need any of that really?

Chris Guillebeau: Yeah. Well, it’s gonna depend on what you’re doing, but I will say over all … and it’s also gonna be different in your, you know, your state or your province or whatever, but I will say overall people focus far too much on that, on those kind of questions, which I don’t mean to say are unimportant, but they focus far too much on that and far less on the more important questions, which I think are … What is the project? How are you gonna turn it into a product or service? What’s it gonna cost? How are you gonna get it out to people? What is your marketing plan? Who are the 10 people you’re gonna ask for help? These are all the little exercises I have in the book to kind of help people with that.

Thinking through that stuff is far, far more important. As for like, what you need in terms of legality … in the US and Canada, and lots of other western countries, it’s usually very, very simple. I mean, you might need a business license, but you can just google your state plus business license. In most cases, you can go and do that online for $35 or maybe $50 or something. You can also even … usually, depending on what it is, you can do that actually after you’ve started the business. If you do need to incorporate, or if you feel like you need to incorporate, that might be a couple hundred bucks, or a few hundred bucks at the highest. But, again, it’s more important, I think, to get your projects up and running.

And if you end up having a success, if something actually takes off, then later you can go and get some advice. And later, you can see about … okay, what do I need to know in terms of tax liability, et cetera? But, I wanna help people to get things going and then figure that out.

Brett McKay: Yeah, that’s kind of what I do with the Art of Manliness. I didn’t have an LLC when I first started, didn’t have any of that. But … ’cause I didn’t know if it was gonna be a thing. And then, as it sort of gained steam, then I went and I found advice on that sort of stuff. So, you got the idea. You know it’s feasible. How do you get the word out about it? Right? So you can get customers. ‘Cause that’s a hard part. I guess … heres the, I think is a paradox. It’s easier than ever to reach people, thanks to social media and the internet. Right? You don’t have to go door to door, handing out flyers about your iPod service. But it’s hard because you’re competing with billions of people who are also possibly vying for attention.

So, how do you get the word out?

Chris Guillebeau: Yeah. Paradox is a good word because … yes, social media, et cetera, but are you really reaching those people, you know. Because like I’m sure a lot of people have experienced, if you try to do something, you can put something out, it doesn’t necessarily mean people are gonna pay attention to it or even care. Certainly less take action on it. So … yeah, I began to touch on that before about … as you get ready to put this into the world, there’s a couple things you can do.

One is I encourage people to ask for help. I encourage people to ask for specific help, not just general help. But make a list of 10 people that you’re gonna go to to ask for something specific. I talk about how to do this. Generally you want to … I got my friend who’s gonna help me with the website. I’ve got somebody else who is pretty good at Instagram, they’re gonna show me how to do this. I’ve got somebody else who maybe might be connected to a group of people that I’m trying to reach. They’re gonna help me with that. There’s a whole other section called, “Sell like a Girl Scout,” which is kind of built on this notion that Girl Scouts don’t have to do a lot of salesmanship.

They’re basically out on the corner and their whole pitch is, “Hey. Would you like to buy some Girl Scout cookies.” And everybody who walks by is like, “Yes. Of Course.” So, how can you basically be like a Girl Scout as opposed to … the counterexample I use is like a street canvasser. If you’re walking down the street in a bigger city, there’s often people that are trying to get your attention, and draw attention to their cause, which may be a very valid and good cause. But it’s essentially … it’s a very hard sell because it’s hard to get people’s attention when they’re walking down the street, and they’re skeptical.

So, they have to kind of do this marketing by guilt. So, I’m trying to show people how to not do that, but how to sell like a Girl Scout. Find the right people. And then reach them, essentially.

Brett McKay: I’m imagining having a website is probably a basic. That’s a no brainer. You need to have that ’cause that’s how people are gonna find you.

Chris Guillebeau: Generally speaking, yeah, for the most part, for the most part I think so. And you know and probably some of the listeners know that it’s not necessarily that complicated to have a basic website. If you’re not a designer, you’re probably not gonna have an amazing website in 27 days, but that’s okay. Here’s a story about a guy who set up a really simple website, kind of doing some of the same stuff that we’ve been talking about. This guy’s name is Tanner, and he went on a cruise with his wife.

And, at first, he was kind of like, “I don’t know if I’m excited about cruises.” But his in laws gave him a gift certificate, so they went on a cruise. But before he went, he had all these questions that he couldn’t find answers to. He was like, “Well, I subscribed to Netflix. Will I be able to watch Netflix on a cruise? How does the internet access work? What are some hacks or tips or tweets to make my experience better? Couldn’t really find that stuff, so he comes back and he’s a copyrighter for his day job, so he’s using his skills here. And he creates a WordPress blog, super simple. The WordPress blog’s purpose is to answer commonly asked questions about cruises, like some of the questions that he had before.

And that’s all it is. It’s just basically like a series of posts, and the posts would be titled, “How can I watch Netflix on a cruise?” And he’d answer that. And they would be like, “How can I watch HBO or like whatever?” A whole series of things. So then he connects that site to Google Ad Sense, which is Googles advertising program. It’s kind of like the Amazon thing. Anybody can sign up for it. THere’s no gatekeeper or secret process to it. And when people visit that site, if they click through on the links to Google, he gets paid.

He starts building this out, just on his weekends or whatever. He does like one post a day, really simple. And about six months in, he’s earning $4,000 a month from this blog. And he’s still doing it. This has been going for a year. Its more than $50,000 a year from a basic website providing information that didn’t exist before. Or, if it did exist, it was hard to find. It was like the cruise lines have their own websites, but they’re telling their story. They have their pitch. And there’s lots of forums you can go to and read tens of thousands of posts, and comments, and contradictory opinions. But nobody wants to do that either. Or at least a lot of people don’t.

Some people just want the answer. So, he found a way to do that using his skills, providing information that people were looking for, and doing hugely, hugely well from it.

Brett McKay: Does he still have his day job?

Chris Guillebeau: I think he does. Yeah, I think so. I think so. Which is good, because he has choice now. He has choice. He has decision making ability. I don’t know exactly where he lives and what his costs are, and the long term plan. But, I hear from some people who do eventually quit their job if it’s going really well. And I hear from some other people who actually have these successes that are making a very significant income, but they like their job because they like the social environment or they like the mission, they believe that they are contributing to something bigger than themselves.

Or maybe, they just think, “I need this for now, and I’ve got this great back up plan. And so, if something changes and I don’t like the social environment, or I don’t like the direction the company is going in … well, now I can actually step away without fear.”

Brett McKay: Well, we’ll talk about if your side hustle’s a success, a smashing success here in a bit. Let’s talk about what if it’s a flop. Right? You put it out there and it’s like okay, no takers. What’s the next step?

Chris Guillebeau: Well, I think, if you do it right, in the way that we’ve been talking about, like your iPod flyer service, then it’s a learning experience. And you basically chalk it up to say, “Okay. Well, I thought that might have been a good idea, but it wasn’t. Or at least it wasn’t in this way.” Here’s what I think is … tends to be more common. People tend to think about the smashing success or the big flop, but it’s just as common to have this third outcome. And the third outcome is, okay, you do everything, you put it out there, and your idea sort of works. Your idea is like … you know, maybe you hoped to have three customers … or three clients or students for your Spanish tutoring business by the end of the week, but you got one.

So, what do you do then? It’s not a smashing success or a complete flop. And so, either way I think you kind of reevaluate and say, “Okay. Is there something I can change about this idea? Do I need to tweak it? Do I still believe in this idea, I just need some refinement of maybe some more marketing or something? Or do I actually think, now that I’ve been through this experience, there might be something I’d be better at. And, in that case I’m gonna go back to, like I said, it’s like a five week process. I’m gonna go back to week number two, which is select my idea. I’m gonna choose a different idea and then pursue it.”

Brett McKay: Right. But again, since you had … you spent so little time and hopefully so little money on it, no harm no foul, you’re okay.

Chris Guillebeau: I think what’s dangerous is when people spend, I don’t know, eight months or even longer than that, and maybe they have invested some real money, and then it’s not a success. You know, I’ve done that in different ways and stuff in the past, but that’s what I think is harder. Right? Because, it’s hard to let go of something like that. Whereas, if you haven’t invested a ton of time, you’re not attached to it as much and so you’re able to make more logical, rational decisions.

Brett McKay: Let’s talk about success. ‘Cause that can … you’re like, “Oh great, I’m successful. I’m making lots of money.” But that can bring its own problems because then you’re under this pressure possibly to expand, because there’s so much demand for it. But you’re like, “Ahhh. I don’t really wanna do that. I don’t have the time.”

At what point should you decide, “Well, maybe I should expand. Or maybe I’m okay where I’m at.” How do you deal with that angst that might exist?

Chris Guillebeau: Yeah. Well, I mean, I think first thing is to acknowledge these are good problems to have. I’m not saying they’re not problems, but it’s good to be in a situation of like how do I pay taxes on all the money that I’ve made? And how do I choose if I’m gonna do the job I’ve been doing, or this side business is actually doing very well? So, still an issue, but great place to be in. So first thing you should do is congratulate yourself And then, I think it just kind of goes back to … what are your goals?

Don’t necessarily let the side business, or your job, or anything else drive the decision. The decision should be within your control, and your influence. And step one of my plan, day one is to find your side hustle goal. And some people just want some extra cash to pay off their debt, or to save for that vacation. And other people want to create this really significant source of income. And other people want to replace their day job in common. It’s okay if your goals change along the way, of course. But still, it’s like what is your goal? What is your intention? What is essentially … not to get super woo woo, but what is the life that you want to live?

And how does your side hustle fit into that? How does everything else in your life, your family, your other responsibilities, et cetera? And then, I feel like, that’s when you start making those decisions. And don’t let something else just kind of take it away.

Brett McKay: At what point do you see most of the people you’ve talked to … they’ve been a success, that they decide to go full time with their side hustle? Is there like a threshold that they meet and they’re like “Okay. I can do this full time”?

Chris Guillebeau: Yeah. If it is your goal to do that, then I think their threshold is essentially whatever you determine to be the minimum amount of income that you need to not just like pay your basic bills, but to feel somewhat secure. And then, when you ge to that point, then you’re able to make that decision as long as you feel that the income is sustainable. Right. Because, sometimes it might not be. But if you feel like you can predict, with reasonable certitude, that this is gonna continue in this world, and it’s only gonna grow, potentially at least, if you devote more time to it. Then, that’s when you make that decision, but not before.

Brett McKay: So, you raise another issue with side hustles that some people … I think I’ve seen people overlook, is the issue of taxes. ‘Cause unlike your job where the company’s taking taxes out automatically. You’re in charge of that. And I’ve seen people with a hell of a side hustle, and their like, “Oh, $700. I spend the entire $700”

And then, tax time comes around and they’re like, “Oh, don’t have enough money for that.”

Chris Guillebeau: Yeah. So, heres a simple recommendation for that. And it’s not even just like to earn the $700. I hear from people that have earned $70,000 and never done that before. They don’t really think about it, and so that’s a much bigger problem. So, a very simple recommendation. Obviously every relations gonna be different. People are in different tax brackets, et cetera, but simple recommendation is the first and most essential thing you should do is you should separate your side hustle income and whatever associated expenses from your personal income. Probably should have said that about the business license, but that is one thing that you should do.

And then, once you actually start making some money, you should just set aside about 25 percent of that for that tax burden that’s gonna come up, and like I said, it may be a little bit higher, may be a little bit lower, but at least that way you’ve got this risen. So when stuff is coming in you know just don’t touch that 25 percent because it’s gonna eventually be due.

Brett McKay: Right. Right. That’s what I … I had an account just for taxes. It goes in there and it’s like a locked safety box. You can’t get to it.

Chris Guillebeau: Yep. ‘Cause you know it’s eventually gonna have to go away. So … yeah.

Brett McKay: Yeah. Can you have more than one side hustle going on?

Chris Guillebeau: You can. I mean, it’s up to you. I’ve seen people do it every way. Some people have a whole lots of collection of side hustles. Other people have kind of a demanding job, and family responsibility stuff, and they’re like, “I’ve got this limited window. I really just have like a brief period of time every day to work on something, so it’s gotta be one thing.” So, it’s really your own personality?

Brett McKay: Any side hustles from your own life? I mean, I think one of the nice things about the book, you give so many examples. But I’m curious about your own life. Are there side hustles that you’ve used that were a success, that flopped, et cetera?

Chris Guillebeau: Yeah. I mean, my life has been side hustles and nothing but essentially because I discovered a world of micro entrepreneurship essentially when I was 18, 19. I learned how to sell things on eBay, and I learned how to buy coffee from Jamaica, found this reseller on line, and I’d have it shipped to my apartment, and have coffee, bags of coffee spread out across my living room table. And then, repackaging it and sending it out to people. It was so fun, the whole process of learning about how to do all that.

And then, at the time, eBay was a very new site. It was kind of an inefficient market, so some went to pay more for things online than they would actually to buy in stores. This is like the early days of the internet, and so I could go to the store and buy … like Toys Rus and buy Leggo’s and then we’d resell them for 20 percent more online. So, learning about how to do all that stuff, it was just a fun little process. And it’s been literally 20 years of doing various things like that and some stuff has worked, and some stuff hasn’t. I once made this huge mistake.

I built a really substantial email list for something about travel related. And, at the time, there was this whole trend about automating your business, and outsourcing and things, and not being in the weeds of your business. And so, I thought I was doing something smart. I did this promotion, sent out this email, and I like walked away and didn’t pay attention at all. And I was really proud of myself. So I was like, “I’m gonna check back like two, to days later, and I’m gonna see all this money that’s come in.”

So, I checked back two days later, and I had sent the wrong link in the email basically. And so … and not only did I send the wrong link, which is a terrible mistake, but a lot of people have made that. The bigger mistake was I didn’t check for two days. So, literally I go back and it’s like zero dollars and a whole bunch of replies that are like, “Hey. The link doesn’t work.” And I’m like, “Oh. Okay. Great.”

Brett McKay: You know what? As you were saying, talking, I thought side hustles are a great way to maybe, if you have kids, teach your kids about entrepreneurship.

Chris Guillebeau: Yeah. Yeah. Of course. We have some fun stories about kids that are doing their own side hustles, or families that are doing ’em together. There’s like a mom and son. The son is really into baseball. And so, they actually designed a new kind of athletic cup because the ones he was wearing were really uncomfortable or whatever, so they actually created this … I forget what it was called, but they’re actually doing a significant side income from this. And together, the whole family … there’s a sister as well, and then the dad, all four of them kind of got into the process of learning how manufacturing works, and how to get this stuff made in China … which has some costs to it, but it’s not like an enormous cost.

They found out over time how to do it kind of on the cheap. And now they’re just like four years in that business.

Brett McKay: That’s awesome. Well Chris, this has been a great conversation. Where can people go to learn more about the book?

Chris Guillebeau: Yeah. Thank you. It has been a great conversation. We’d love to hear from some listeners some time. The book is called, “Side Hustle: From Idea to Income in 27 Days.” It should be at any book store, or any online reseller including Amazon, Barnes & Noble, wherever you shop for books. And the website is And there’s a daily podcast as well called “Side Hustle School.”

Brett McKay: Awesome. Chris Guillebeau, thank you so much for your time. It’s been a pleasure.

Chris Guillebeau: Thank you sir.

Brett McKay: Like I say, it was Chris Guillebeau, he’s the author of the book “Side Hustle: From Idea to Income in 27 Days.” It’s available on and bookstores everywhere. You can also find out more information about his work at, where he has a podcast where he interviews people who started side hustles and digs in to how they did it. Also, check out our show notes at hustle where you can find links to resources, where you can delve deeper into this topic.

Well, that wraps up another edition of The Art of Manliness podcast. For more manly tips and advice, make sure to check out the Art of Manliness website at And if you enjoyed the show, you feel like you got something out of it, share with a friend. One thing I discover when I talk to people about how they discover the podcast, most say a friend or family member told them about it. It wasn’t social media. It wasn’t Facebook. It wasn’t Twitter. So please … it would really mean a lot if you tell a few friends about the show, the more, the merrier.

As always, I appreciate the continued support, and until next time this is Brett McKay, telling you to stay manly.

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