#344： The Art of the Side Hustle
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Summary
Chris Guillebeau's new book, Side Hustle: From Idea to Income in 27 Days, details the process of starting a side hustle from ideation to business formation to marketing. Along the way, Chris busts some myths about starting a business and provides examples of folks who have added $1,000 to $20,000 a month to their income with the business they work on in their free time.
Transcript
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Brett McKay here and welcome to another edition of the Art of Manliness podcast. If you're
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looking to pay down debt or save it for a financial goal faster, there are two ways
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to do it. You save more money or make more money. And let's assume you're knocking out
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of the park with your frugality, you're saving as much as you can. How can you make more
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money? We're talking legally here. Well, one way is starting a side hustle. And besides
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providing you with extra income, my guest today argues that having a small business on
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the side can actually bring you a lot more satisfaction and confidence to your life.
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His name is Chris Guillebeau, and I've had him on the podcast before to discuss his book
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Born for This. Today on the show, Chris and I discuss his latest book, Side Hustle from
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Idea to Income in 27 Days. Chris and I begin our conversation talking about why every man
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should have a side hustle, including men who are already very happy with their day jobs.
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Chris walks us through the process of starting a side hustle from ideation to business formation
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to marketing. Along the way, Chris busts some myths that people have about starting a business
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and provides examples of folks who have added $1,000 to $20,000 a month to their income with
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the business they work on in their free time. Lots of actionable advice in the show. And after
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it's over, check out the show notes at aom.is slash side hustle, where you can find links
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to resources, we can delve deeper into this topic. Chris Guillebeau, welcome back to the show.
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Thank you for having me back. I think it's like the, you know, seventh or eighth time I've been
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on the show. Not quite seven or eight, but it's a big honor. Yeah. A three, Peter, because you're
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always coming out of these books. So I got to have you back on the show. The last time we had you on
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the show, we talked about, you know, building your dream career. And we got a lot of positive
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feedback from that. Your new book is called Side Hustle from Idea to Income in 27 Days.
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We've written about side hustles on the site before. We're a big proponent of them.
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For those who aren't familiar with the concept of a side hustle, how do you define a side hustle?
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You know, a lot of people are talking about side hustles in a lot of different ways. And I really,
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I'm glad to hear that you had some good feedback from our last conversation. I actually feel like
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this new book, Side Hustle, is probably the most relevant to your listeners that I've ever
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ever written. And I'm trying to focus my side hustle focus or my side hustle push on creating
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assets, on creating something that you have ownership over. And the reason why I'm doing
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that, well, one, it's just smart. But then also, I feel like in the culture, some people are talking
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about side hustles as part of the gig economy or as part of like, you know, the notion that people
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have to have two or three jobs these days. And I'm not really trying to encourage people to work
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harder or to do a 40 hour a week, you know, job and then go and do a 20 hour a week job somewhere
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else. I'm trying to help people create something that they can point to and say, you know, I have
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ownership over this thing and it's making money for me. And maybe I never wanted to be an entrepreneur.
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Maybe I still don't want to be an entrepreneur. But it's really great that, you know, at the end of
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the month, I can have my paycheck and I can have this extra income coming in. And that just feels
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really good. So that's what I'm trying to help people with.
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So there's a lot of reason people start side hustles. And I think you argue that everyone
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should have a side hustle. Even if you got a satisfying career, you love your job, you should
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You know, I've never felt more strongly about something, I think, and about this concept in
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particular, because I am not trying to encourage people to go out and quit their jobs. Like I did
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that a little bit with a previous book, $100 Startup that I wrote and kind of learned through that
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process like that book resonated with a lot of folks. And a lot of folks said, well, that's not
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really me. I actually love my job, you know, or maybe eventually I want to quit my job, but I
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can't do that right now. Everybody needs to have more than one support for them, though. I think
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it's smart for security. I think it's good to have a backup plan. It's good to have more option
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freedom. There's really no downside to it. I feel like if you invest in this process the right way,
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and by invest, I'm talking mostly about your time, not talking about spending money,
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then I feel like only good things come from it. You know, and like I said, it gives people
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confidence, makes them feel empowered. And of course, it's extra money. So, you know, one way
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to look at it is like, oh, look at what's happening in the world and the economy and people don't have
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security and traditional jobs. All that is true. I agree. The other way to look at it, in addition,
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is to say, well, this is something that's, you know, creative, empowering, makes you look at it and
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say, like I mentioned, you know, I made this thing, I own it. And it also can be fun. It can be
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something that you look forward to doing. You know, it's not something you dread. It's something
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you look forward to doing at the end of the day or your 20 minutes in the morning or whatever time
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you have for it. Yeah. I think that last point is a good one because a lot of people who,
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they might not hate their job, but it's not giving them the creative outlet that they might
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are desiring. Like a side hustle allows them to do that and also make money in the process.
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Yeah. Yeah, exactly. I talked to a guy last night. I'm on this tour to do 100 cities,
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talk with people about side hustles. And I generally think it's good to do something a little bit
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different for your side hustle than you do for your day job. And I did meet someone last night
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who was like, oh, I'm a web developer by day and I'm a web developer at night. That can work. I mean,
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some people do that. What I tend to see people just having more enjoyment with and maybe even more
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success with is something that's totally different. So there's a story I did recently about a guy who's
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a managerial accountant and his side hustle is producing poetry slams. And he makes like a thousand
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dollars a month, you know, putting on these poetry slams, which is great because you never hear
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about a poet making money. Right. But then also like he's the, you know, accountant by day,
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poet by night. So totally different kind of thought process and work and creative outlet,
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What does it take to start a side hustle? Does it require a lot? Because I think a lot of people,
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you know, because it's a business, right? And I think people think, oh, there's a lot of hoops
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I got to jump through. What does it actually take to start one?
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Right, right. Yeah. It basically takes all your life savings and you need to go back to school for
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four years. And yeah, no, it takes none of that. What I'm trying to do with the book and the tour
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show people this process and the process is idea to income in 27 days. So I really am encouraging
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people to like get this, get this thing started quickly. And as I said, it's not about spending
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money. It's also not about this extensive planning phase as well. So basically what it's about is,
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is helping people use the skills they already have to, you know, create some kind of product or
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service. And I think that's, that's key because people tend to think about business ideas, you
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know, quote unquote, and people, consumers, like all of us, we don't buy ideas. Like we buy products
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or services. So I'm helping people like look at the skills they have and figure out how can I package
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that into some kind of product or service? How can I then turn that into some kind of offer?
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And then how can I get that out to the world? Probably before I'm ready, you know, so that I can get
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some real world feedback, not just asking my buddies like, Hey, what do you think about this idea?
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But putting it out and seeing how people really respond and then kind of regrouping from there.
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So, you know, 27 day process, it's, it's broken out into like five weeks. You know, you do one
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thing a day. As I said, 20 to 30 minutes a day. And at the end, you should have some, some real
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results and you should be able to actually point to something and say, look, that's, that's my side
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hustle. So let's talk about the start of the ideation process. Where can people get ideas for side
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hustles? A lot of people are like, I want to start a business, but I don't know what to do. So where can
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people find these ideas? Yeah. It's really interesting. I've learned through a lot of
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research and like, you know, eight years of working on this in different ways that half
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the people struggle with, with that, what you just mentioned, like, where do ideas come from?
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I don't know what I have. That's a good idea. The other half of the people struggle with,
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like, I have an idea. Ideas aren't my problem. I just don't quite know what to do next. Or I can't
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choose between different ideas. So the first part, because like the book goes through both sections.
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So learning where ideas come from is essentially a skill that, that nobody really learns in school.
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Your parents didn't teach you, but it's not that hard to develop. So it's essentially about
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developing your skill of curiosity or developing the power of observation and just beginning with
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paying attention. So paying attention, first of all, to daily life, like as you kind of go through
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the world, looking around and noticing not just things that you like, but what things do you not
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like? And, you know, what frustrations do you encounter? What problems do you encounter? Like,
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how could, you know, somebody create some kind of a solution to something? The second part is
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also then looking at yourself. What are your skills? What are all your skills? It's not just
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skills that you use, you know, for your day job or what you got your degree in if you went to
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college. But what is something that we can actually like combine with these two things,
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like your skill, your background, your interests, and then also like some kind of problem in the
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world or something that, you know, can then turn into, as we've said, a side hustle. So I try to walk
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people through all these different examples, you know, of like, okay, here's how this person did it.
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And hopefully that gets you thinking, because you're not going to do the same thing that they
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did or that I did or anybody else. But through this process, hopefully, you can get, you know,
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the ideas that you need. And say you get some ideas, how do you determine if it's feasible,
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right? Because like, you might have this idea, you think it sounds great on paper, but then,
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okay, actually, I'm going to lose money trying to make this a business. So how do you figure that
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out before you make too much of an investment of time or money into it?
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Sure, sure. Well, I'll say two things about this. You know, one, one to your direct question,
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like there is a process that I show in the book about how to test your idea with $10 in a Facebook
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account. And it's this really simple process of basically like, you know, writing an ad and kind
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of just kind of seeing how people respond. It's not that difficult to set up. And as I said,
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it costs like $10. However, I'll also say that, like, I have this daily podcast called Side Hustle
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School. And every day on the show, seven days a week, a story of somebody who does this. And so telling a
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story of an employee who starts an income generating project without quitting their job,
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how'd they get the idea? You know, what happened? How'd they develop it? What challenges did they
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encounter? How much money did they make from it? And what I have seen is that it's actually not
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always possible to like, to know in advance, like if this thing is going to work, or it's not possible,
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not always possible to know if your ideas is going to be validated. And so sometimes you just have to,
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you just kind of have to try. And that's why the process is short. That's why it's, you know,
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27 days so that you're not, you know, investing a huge amount of time or spending a year planning
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something that you don't know if it's, if it's going to work or not. So I like, I like to feature
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a bunch of like quirky kind of different stories. Like the book begins with this guy who wrote a blog
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about fish tank reviews and like, he was really into fish. And so he spent like a weekend, like a short
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period of time, like writing these fish tank reviews and linking to Amazon where he had an affiliate
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account, which anyone can create. And he kind of went away and didn't really think much about it.
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And a month later, he got a check for $300 in the mail. And he's like, Oh, okay. You know,
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that's, that's interesting. And so he put a little bit more work into it, but eventually kind of left
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it because he was a construction project manager and busy guy. So the short version of the punchline
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of that story is this was like three years ago and three years on, like literally every single month,
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he's been getting a check in the mail from Amazon for $700. So $700, you know, is not a necessarily a
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life-changing amount of money. You can't live off of it, but it's very significant,
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especially for something that you don't do anything for. Right. So he's been able to take
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his wife on extra vacation every year and do all this kind of stuff. If you had tried to like
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validate the fish tank review idea before he started it, I don't know if you, if you could,
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you know, I think a lot of people would say that's kind of a dumb idea, but you know, obviously it
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worked out pretty well for him. Yeah. $700 a month that would pay for rent in a two bedroom apartment
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here in Tulsa, Oklahoma. Yeah. Right. Right. Think about that. Yeah. Or help you pay off debt.
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You know, I hear from a lot of people that have student loan debt or credit card debt or,
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you know, just, just whatever. It's like, it's, it's, it's a real thing. And so that's why I
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actually like for the show and for the book itself, I have this minimum, like you have to be making at
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least $500 a month, you know, to be featured on the show or every story in the book. And actually my
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goal for people, if like you, if you go through the book and you go through the process, like I'm
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personally not going to be satisfied as the author, if, if the project you create is not doing at least
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$500 a month. And there's a lot of stories, uh, you know, in the book of people who've gone on to
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actually do, you know, six figure side hustles or much more. And I love those stories too. Um,
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we could get into those, but I think like, it's also relatable in some ways to, to point to people
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who are like, you know, $500, $1,000 a month. So the idea is that a side hustle idea, like you,
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you should invest so little into it that it's okay. If you invest some time or some money,
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because it's so little that if it flops, it's not that big of a deal.
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Yeah, exactly. The risk is low, right? And this is, this is like a counterpoint to traditional
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entrepreneurship because traditional entrepreneurship is all about, oh, you're going
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to take a big risk. You might get a big reward. You know, you're like trying to start this startup
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or whatever it is. You know, maybe there's like this huge reward that waits, that awaits on the
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other side, but there's also like this huge chance, a chance of major failure. And I'm trying to like
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take that, that huge chance of failure out of the process, um, so that people can, can experiment.
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And I think of it like a, like a hobby. It's like a hobby. It's something you look forward to. Like
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we said, it's something you enjoy. Maybe you'll spend a little bit of money on it, but you spend
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a little bit of money on your hobbies. Right. And this, this has the potential to be a hobby that
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actually pays you money. Right. So that's the, that's the key. Yeah. I mean, here's two examples
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from my own life of side hustles that didn't cost me any money. Um, one was a success. One was a flop.
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So when I, I lived in Mexico for a few years, so I speak Spanish fluently, not so much anymore,
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but when I was in college, I, um, offer tutoring services. So I just, all it is, I printed off a
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little flyer and hung it up in like where all the Spanish classes are at and didn't cost me anything.
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And like within a week I had three clients pay me 20 bucks a week for Spanish. And it took me like
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three hours a week and I was making 60 bucks a week extra and cost me nothing. The other side hustle
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that I tried was like when iPods first came out and people like had all these, I had like these
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digital files or they had CDs with all their music. And like, I, I tried to like offer a service where
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I would rip their CDs and put them onto their iPod. I just printed a flyers and I like just hung up on
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the doors. Didn't, I spent maybe like two hours and no money basically. And that didn't go anywhere.
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I didn't get any bites from that, but it was no, no harm, no foul.
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Exactly. Yeah. I mean, both examples, like you, you printed some flyers, you know,
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like a small investment of your time and one of them, one of them worked and one of them didn't,
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you know, that's good. And you're not, like I said, there's no other startup costs to that,
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like none at all. So, so that's good. Yeah, that's good. I mean, so can I maybe make a quick
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comment on that, that first example? Um, you know, there you're obviously using a skill that you had.
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It was something that other people clearly needed and desired. They needed help, you know,
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with like improving their, their Spanish language skills. And in the second example, like you thought there
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would be a need, or you, you, you wondered if there would be, and it turned out there, there wasn't.
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So I have this concept of, um, like starter ideas and next level ideas in the book. And I think your
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example of like the tutoring Spanish is, is a great example of a starter idea. And when I say starter,
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it's not any kind of negative, you know, context at all. Uh, it just means that it's, it's a fairly
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limited idea in terms of like the scope and the scalability of it, because you can only tutor so much,
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uh, people can only pay a certain amount of tutoring. Like you could, you can probably raise
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your rate at a certain point, but you can't raise it indefinitely because eventually somebody's just
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going to go to another Spanish language tutor. So what I'm trying to help people do is like
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definitely experiment with the starter ideas. That's great. Like you can sell something on Etsy,
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you know, tomorrow you can sign up for the platform Fiverr and like offer some kind of service tomorrow.
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Um, but you know, the challenge there is like, you're going to be kind of locked into somebody else's
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environment. Like you have to kind of play by their rules. Like they essentially can cap your
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income in some ways, just like driving for Uber or Lyft or whatever. So next level idea is something
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that you actually like do have this ownership over. Um, it's something that has the potential to earn
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a lot more money. So very quick story about another guy who was also like, he was actually trying to
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learn Spanish and he had lived in Argentina for a while and I got somewhat proficient, but then he moved
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back to Canada and like was, was kind of losing his skills. And so he downloaded an app and like,
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he liked the app. I think it was Duolingo. He said it was good, but he'd also felt kind of impersonal.
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And then at the same time, one of his, one of his buddies was like, uh, also trying to like brush
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up his Spanish and hired a tutor on Craigslist, which is kind of like what you were doing. And
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he liked that process, but he was paying $25 an hour for it. So I thought this isn't super
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efficient either. So short version is this guy, I think his name is Sean. He created a,
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he created a platform that essentially allows like Skype language lessons, you know, from people
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in the U S and Canada back with, you know, people in Argentina or Chile or elsewhere. And so then
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there's like an economic difference in terms of the cost and people can log on at any time. They
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don't have to like coordinate on meeting with Starbucks or whatever. So this project has
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actually super, super taken off. And within a year, it's actually more than $150,000 that he's made
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from it. So that's kind of like a difference between a starter idea and something that could
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potentially go on to do much more. Right. The other idea, the next level idea that I thought
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was good was the Uber driver became an Uber driver coach, which was interesting.
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Yes. Yeah, exactly. That's a friend of mine named Harry Campbell, actually here in Southern
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California where I'm talking to you from. And, uh, it's exactly what you just said. He,
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he was an Uber driver and was interested in, you know, learning more about how to, how to do a better
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job and how to increase his hourly rates and, you know, get his rating higher and stuff like that.
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And so he's, he's like Googling to try to find this information feeling frustrated because there's
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not a ton of stuff out there. And so he decides to actually create this platform called, you know,
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the, the ride share guy. And so on this platform, which he's now built out over, I think about two
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years or so now, um, you know, he has, he has coaching sessions that he does. I think he has some
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kind of product. He's also like, you know, speaking in the media a lot about it. So he's built this
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whole authority. So, uh, he, you know, he went from driving to for Uber, which is a good starter
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idea. Like you have some flexibility over your hours, et cetera, but it's also kind of limited
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because of competition and the rates are set by Uber, not by you. Now he's gone to this thing that
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is, it is more entrepreneurial in the sense that he can do whatever he wants and he can take that in
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lots of different directions. So let's say you, you, you narrowed on an idea. It's feasible. You
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think you can make a good go at it, but you, in your research, you discover that there are other
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people who are doing pretty much the same thing that you're doing, right? Like, I mean,
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that example of the guy with the app, the Spanish app, I mean, he, he able to find, he was able to
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find a way to tweak that a bit, but let's say there's no way to tweak your side hustle. There's
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like a lot of dog walkers in your town. What do you do in that case? Should you go ahead? Or she's
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like, okay, I'm going to do something else. Well, you know, I guess I would, I would say to that
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example, like, are there a lot of dogs in your town? Because, you know, one dog walker can't serve
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the whole market. And in a lot of ways, seeing that somebody else is, is, you know, doing your ideas
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is actually validation itself because you can see, okay, somebody is doing this. They're
00:18:44.900
actually getting paid for it. I'm not reinventing the wheel here, but you don't have to reinvent
00:18:48.900
the wheel. You know, most, most people aren't going to, like, I feel like people are kind
00:18:53.860
of obsessed with like, you know, I don't have a side hustle idea because I don't know how
00:18:58.700
to invent the next iPhone or whatever. Well, you're, you're probably not going to, going
00:19:02.240
to do that, you know, in 27 days, you know, 20 minutes a day or whatever. So I don't necessarily
00:19:07.360
think it's bad that somebody else is doing that. Even like the language thing, like,
00:19:10.960
let's say that somebody else was doing exactly the same model that he was doing. There's
00:19:14.960
still like so many people out there that, you know, want to learn Spanish or it could
00:19:18.600
choose a different language or do it in a different way. So not necessarily a bad thing.
00:19:23.200
Yeah. Sometimes there's a, there's a disadvantage to being the first mover.
00:19:26.220
Yeah. Because then you have to essentially educate people on, you know, why they, why they
00:19:31.340
need this thing that they've never heard of before.
00:19:33.100
Let's say you get the idea, what do you need to get started? Because I think going back to
00:19:36.200
that, yeah, people think they need to do a lot. Like they have to get business licenses.
00:19:39.580
They need to incorporate to have a business. They need a business account. They need cards.
00:19:43.380
Like what exactly do you need to have sort of legally sort of the back, the structure
00:19:48.900
to get a side hustle going? Or do you need any of that really?
00:19:51.700
Yeah. Well, it's going to depend on what you're doing, but I will say overall, it's also going
00:19:56.200
to be different in your, you know, your state or your province or whatever. But I will say overall
00:19:59.760
people, people focus, you know, far too much on, on that, on those kinds of questions,
00:20:05.680
which I don't mean to say are unimportant, but they focus far too much on that and far,
00:20:09.800
far less on the more important questions, which I think are like, okay, what, what is
00:20:14.100
the project? Like, how are you going to turn it into a product or service? How, what's
00:20:17.480
it going to cost? How are you going to get it out to people? Like, what is your marketing
00:20:20.380
plan? Like, who are the 10 people you're going to ask for help? Which these are all the little
00:20:24.060
exercises I have in the book to help, to help people with that. That, like thinking through
00:20:27.620
that stuff is far, far more important. Um, as for like, you know, what kind of, you know,
00:20:32.200
what do you need in terms of legality, you know, in the U S and Canada and lots of other
00:20:36.120
like Western countries, it's, it's usually very, very simple. I mean, you might need a
00:20:39.300
business license, but you can just Google like your state, you know, plus business
00:20:43.060
license. In most cases, uh, you can, you know, go and do that online for $35 or maybe
00:20:48.820
50 bucks or something. Um, you can also, also even, you know, usually depending on what it
00:20:53.120
is, you can do that actually after you've started the business. Um, if you do need to
00:20:56.760
incorporate, or if you feel like you need to incorporate, that might be like a couple
00:20:59.200
hundred bucks or a few hundred bucks at the, at the highest. But, uh, again, it's
00:21:03.320
more important, I think, to get your projects like up and running. And, uh, you
00:21:07.080
know, if you end up having a success, you know, if it's something actually takes
00:21:10.040
off, well then later you can go and get some advice and later you can see about,
00:21:14.060
okay, what do I need to know in terms of tax liability, et cetera. But, um, I want to
00:21:17.640
help people get things going and then figure that out.
00:21:20.080
Yeah. That's kind of what I do with the art of manliness. Uh, didn't have an LLC when
00:21:23.200
I first started, didn't have any of that, but cause I just, I didn't know it was
00:21:26.760
going to be a thing. And then as it scored against steam, then I went and I found
00:21:30.280
advice on that sort of stuff. So you got the idea you've, you, you know, it's
00:21:34.160
feasible. How do you get the word out about it? Right. So you can get customers
00:21:38.900
cause that's, that's, that's a hard part. I guess here's the, I think it's a
00:21:42.260
paradox. Like it's easier, it's easier than ever to reach people thanks to social
00:21:46.860
media and the internet, right? You don't have to go door to door handing out
00:21:49.880
flyers about your iPod service, but it's hard because you're competing with
00:21:54.000
billions of people who are also possibly vying for attention. So how do you get
00:21:59.080
the word out? Yeah. Paradox is a good word because yes, you know, like social
00:22:02.620
media, et cetera, but are you really reaching those people? You know, because
00:22:05.660
like, I'm sure a lot of people have experienced, uh, if you've tried to do
00:22:08.700
something, like you can put something out, but it doesn't necessarily mean people
00:22:11.320
are going to pay attention to it or even, even care certainly less, you know, take
00:22:14.920
action on it. So yeah, I, you know, began to touch on that before about like, uh, you
00:22:19.480
know, as you get ready to, to put this into the world, like there's a couple of
00:22:22.920
things you can do. Um, one is I encourage people to ask for help. Uh,
00:22:26.680
I encourage people to ask for specific help, not just like general help, but
00:22:29.380
make a list of, you know, 10 people that you're going to go to, to ask for
00:22:33.860
something specific. And I talk about how to do this. Like generally you won't
00:22:37.460
want to, like, I mean, I got my friend who's going to help me like with the
00:22:39.780
website. I've got somebody else who is pretty good at Instagram. They're going to
00:22:42.920
show me how to do this. I've got somebody else who, you know, maybe he could,
00:22:46.360
might be connected to a group of people that I'm trying to reach. They're going to
00:22:49.040
help me with that. Um, there's a whole other section called sell like a
00:22:52.220
Girl Scout, um, which is kind of built on this notion that, um, you know,
00:22:56.480
Girl Scouts don't have to do a lot of salesmanship. Like they're basically like
00:22:59.360
out on the corner and their, their whole pitch is like, Hey, would you like to
00:23:01.880
buy some Girl Scout cookies? And everybody who walks by is like, yes, you know, of
00:23:05.760
course. So how can you basically be like a Girl Scout, you know, as opposed to like
00:23:11.320
the, the counter example I use is like a street canvasser. Like if you're walking
00:23:14.580
down the street in a, in a bigger city, there's often people that are trying to get
00:23:17.560
your attention and like, you know, draw attention to their cause, which may be a
00:23:20.580
very valid and good cause, but it's essentially, it's a very hard sell because
00:23:24.820
it's hard to get people's attention when they're walking down the street and
00:23:27.400
they're skeptical. And, you know, so they have to kind of do this like
00:23:30.080
marketing by guilt. So I'm trying to show people how to not do that, um, but how
00:23:33.800
to, you know, sell like a Girl Scout, uh, find the right people and then, you
00:23:39.640
I imagine having a website is probably a basic, like that's a no brainer. You need
00:23:43.180
to have that because that's how people are going to find you.
00:23:45.480
Generally speaking. Yeah. For, for the most part, you know, for the most part,
00:23:47.940
I think so. And, and I mean, you know, and probably some of the listeners know
00:23:51.400
that, you know, it's not necessarily that complicated to have a basic website.
00:23:54.920
You know, um, if you're not a designer, you're probably not going to have an
00:23:57.940
amazing website in 27 days, but that's okay. You know, here's a, here's a story
00:24:02.000
about a guy who, who set up a really simple website, kind of doing some of the
00:24:05.760
same stuff that we've been talking about. This guy's name is Tanner. And, uh, he
00:24:09.760
went on a cruise with his wife and at first he was kind of like, I don't know if I'm
00:24:13.700
excited about cruises, but his in-laws gave them a gift certificate. So they went on the
00:24:17.720
cruise. Um, but before he went, he had all these questions that he couldn't
00:24:20.780
find answers to. He was like, well, I subscribe to Netflix. Like, well, I'd be
00:24:24.220
able to watch Netflix on the cruise. Like how does the internet access work?
00:24:27.340
Like what are some like hacks, you know, or tips or tweaks to make my experience
00:24:31.440
better? Couldn't really find that stuff. So he comes back and he's a copywriter
00:24:35.960
for his day job. So he's like using his, his skills here. And he creates a
00:24:41.020
WordPress blog, super simple. Um, the WordPress blog's purpose is to answer
00:24:45.780
like commonly asked questions about cruises, like some of the questions that
00:24:49.000
he had before. And that's all it is. Like, it's just basically like a series
00:24:52.020
of posts. Like, and a post would be titled like, how can I watch Netflix on a
00:24:56.040
cruise? And so he'd like answer that. And then it would be like, how can I watch
00:24:58.920
HBO or like whatever, like a whole series of things. So then he connects that, um,
00:25:03.560
connects that site to, um, Google AdSense, which is Google's advertising
00:25:07.540
program. It's kind of like the Amazon thing. Anybody can sign up for it. There's no,
00:25:10.700
like, there's no gatekeeper or thing or like process to it. And when people visit
00:25:14.920
that site, if they click through on the links to Google, he gets paid. But he
00:25:19.000
starts building this out just like, you know, on his weekends or whatever, he
00:25:22.120
does like one post a day, like really simple. And about six months in he's
00:25:26.780
earning $4,000 a month from this blog and he's still doing it. Like this has
00:25:31.780
been going for like a year. It's like more than $50,000 a year, you know, from
00:25:35.640
basic website, providing information that didn't exist before. Or if it did
00:25:39.840
exist, it was hard to find, you know, it was like the cruise lines have their
00:25:42.660
own websites, but they're telling their story. Like they have their pitch and
00:25:45.920
there's lots of forums you can go to and read like tens of thousands of posts
00:25:50.080
and comments and contradictory opinions, but nobody wants to do that either.
00:25:53.360
At least a lot of people don't. Some people just want the answer. So he found a
00:25:56.740
way to do that, like using his skills, providing information that people are
00:25:59.840
looking for and like doing hugely, hugely well from it.
00:26:04.360
I think he does. Yeah, I think so. I think so. But you know, it's, which is good
00:26:07.900
because like he has, he has choice now. He has choice. He has decision-making
00:26:11.960
ability. I don't, I don't know exactly like, you know, where he lives and what
00:26:15.140
his costs are and like the long-term plan. But I, I hear from some people who,
00:26:19.200
you know, do eventually like quit their job if it's going really well. And I hear
00:26:22.840
from some other people who actually have these successes that are making a very
00:26:26.340
significant income, but they like their job because they like, you know, the
00:26:29.920
social environments or they, they like the mission. Like they believe that they're
00:26:33.780
contributing to something bigger than themselves. Or maybe they just think like,
00:26:37.300
I need this for now. And like, I've got this great backup plan. And so if, if
00:26:40.920
something changes and I don't like the social environment or I don't like the
00:26:43.840
direction the company's going in, well, now I can actually, you know, step away
00:26:48.940
Well, we'll talk about if your side hustle is a success, a smashing success here
00:26:52.540
in a bit, but let's talk about what if it's a flop, right? You put it out there
00:26:56.240
and it's like, okay, nope, no takers. What's the next step?
00:27:00.300
Yeah. Well, I think if you do it right, like in the way that we've been talking about,
00:27:03.160
like your, your iPod, you know, flyer service, then it's a learning experience. And
00:27:07.720
you basically chalk it up to say, okay, well, you know, I thought that might've
00:27:10.700
been a good idea, but it wasn't, or at least it wasn't in this, this way.
00:27:15.240
Here's what I think is, is tends to be more common. I think people, people tend to
00:27:18.520
think about the smashing success or the big flop, but it's just as common to have
00:27:23.480
like this third outcome. And the third outcome is like, okay, you do everything and
00:27:27.220
you put it out there and your, your idea like sort of works. Like your idea is
00:27:32.380
like, you know, maybe you, you hope to have like three customers or three clients
00:27:36.680
or students for your Spanish tutoring business by the end of the week, but you
00:27:40.000
got one. So what do you do then? Like it's not a smashing success or a complete
00:27:43.420
flop. And so either way, I think you, you kind of reevaluate and say, okay, you
00:27:47.600
know, is there something I can change about this idea? Do I need to tweak it? Do I
00:27:52.320
still believe in this idea? I just need some refinement or maybe some more
00:27:55.340
marketing or something, or do I actually think now that I've been through this
00:27:57.980
experience, there might be something I'd be, I'd be better at. And in that case,
00:28:01.540
I'm going to go back to, like I said, it's like a five week process. I'm going
00:28:04.300
to go back to week number two, which is select my idea. I'm going to choose a
00:28:07.840
different idea and then, and then pursue. Right. But again, since you had, you
00:28:10.700
spent so little time and hopefully it's a little money on it, no big, no harm, no
00:28:14.860
foul. You're okay. I think what's, I think what's dangerous is when people
00:28:17.820
spend, spend, you know, I don't know, like eight months or even longer than
00:28:21.820
that. And maybe they have invested some real money and then it's not a
00:28:25.260
success. I mean, and, and, you know, I've done that in different ways and
00:28:28.140
stuff in the past, but that's what I think is, is harder, right? Because
00:28:31.360
it's hard to let go of something like that. Whereas if you haven't invested a
00:28:35.180
ton of time, you're not attached to it as much. And so you're able to make more
00:28:40.200
All right. Let's talk about success. Cause that can, you're like, oh great, I'm
00:28:43.800
successful. I'm making lots of money, but that can bring its own problems
00:28:46.620
because then you're under this pressure possibly to expand because there's so
00:28:51.220
much demand for it. But you're like, ah, I don't really want to do that. I
00:28:54.280
don't have the time. At what point should you decide, well, maybe I should
00:28:58.880
expand or maybe I'm okay where I'm at. How do you deal with that angst that
00:29:03.340
Yeah. Well, I mean, I think first thing is to acknowledge, like, these are good
00:29:05.560
problems to have. Like, I'm not saying they're not problems, right? But it's,
00:29:08.540
it's good. It's good to be in a situation of like, you know, how do I, how do I pay
00:29:12.420
taxes on like all the money that I've made? And like, how do I choose, you know, if
00:29:16.260
I'm going to do the job I've been doing or this, you know, side business that's
00:29:19.480
actually doing very well. So it's still an issue, but like great place to begin. So
00:29:23.100
the first thing you should do is congratulate yourself. And then I think
00:29:25.900
I could kind of just kind of goes back to like, what are your goals? Like
00:29:29.200
don't necessarily let the side business or your job or anything else drive the
00:29:33.120
decision. Like the decision should be, the decision should be within your
00:29:37.660
control and your influence. And like step, step one of my plan, like day one is
00:29:42.260
like define your side hustle goal. And some people just want some extra cash, you
00:29:46.960
know, to pay off their debt or to save for that vacation. And other people want to
00:29:50.500
connect to create this really significant, you know, source of
00:29:53.820
income and other people want to replace their day job income. And it's okay if
00:29:57.080
your job, if your goals change along the way, of course, you know, but still
00:29:59.560
it's like, what is your goal? Like, what is your intention? You know, what is
00:30:02.440
essentially like, not, not to get like super, you know, woo woo, but like, what is
00:30:06.200
the life that you want to live? And, you know, how does your, your side hustle fit
00:30:10.120
into that? How does everything else in your life, your family, your other
00:30:12.460
responsibilities, et cetera. And then I feel like that's when you start
00:30:16.200
making those decisions and don't let something else just kind of, you
00:30:18.580
know, take, take it away. At what point do you see most of the people you've
00:30:21.840
talked to, you know, they've been a success that they decide to go full
00:30:25.900
time with their side hustles. They're like a threshold that they meet and
00:30:28.760
they're like, okay, I can do this full time. Yeah. I think if it, if it is your
00:30:32.220
goal to do that, then I think the threshold is essentially like whatever you
00:30:37.040
determine to be the minimum amount of income that you need to, to not just
00:30:43.340
like pay your basic bills, but to feel somewhat secure. And then when you get to
00:30:46.960
that point, then you're able to make that decision as long as you feel that the
00:30:50.460
income is, is sustainable, right? Because sometimes it might not be, but if you
00:30:54.100
feel like you can, you can predict, you know, with reasonable certitude that this
00:30:59.560
is going to continue in this way and it's only going to, only going to grow, you
00:31:02.540
know, potentially at least if you devote more time to it, then, then that's when
00:31:07.340
So you raise another issue with side hustles that some people, I think I've seen
00:31:10.680
people overlook is the issue of taxes because unlike your job where, you know,
00:31:15.340
the company's taking taxes out automatically, like you're in charge of
00:31:19.120
that. And I've seen people that have a side hustle and like, Oh, $700. I spend
00:31:22.380
the entire $700. And then tax time comes around and like, Oh, don't have enough
00:31:28.400
Yeah. So here's a simple recommendation for that. And it's not even just like the
00:31:32.020
earned the $700. It's, you know, I hear from people that have earned $70,000, you
00:31:35.680
know, and never done that before. And, you know, they don't really think about it. And so
00:31:39.440
that's a much, much bigger problem. So very simple recommendation. Obviously,
00:31:43.640
everyone's going to be different. People are in different taxes, et cetera. But
00:31:46.740
simple recommendation is the first and most essential thing you should do is you
00:31:52.720
should, you should separate your side hustle income and whatever associated
00:31:55.980
expenses from your personal income and expenses. So probably should have said that
00:31:59.560
about the business license, but that is one thing that you should do. And then, you
00:32:03.380
know, once you actually start making some money, you should just set aside about
00:32:06.360
25% of that for that tax burden that's going to come up. And like I said, it may be a
00:32:11.100
little bit higher, maybe a little bit lower, but at least that way you've got
00:32:13.280
this reason. So when stuff is coming in, you know, just don't touch that 25%
00:32:19.160
Right, right. That's what I, that's what I have an account just for taxes. And like
00:32:22.180
it goes in there and it's like a, it's a lock safety box. You can't get to it.
00:32:26.160
Yeah. Cause you know, it's eventually going to have to go away. So yeah.
00:32:29.060
Yeah. Can you have more than one side hustle going on?
00:32:31.420
You can. I mean, it's up to you. It's, I've seen people do it every way. You know,
00:32:35.060
some people like have a whole lot. It's a collection of side hustles. Other people have
00:32:38.860
kind of a demanding job and, you know, family responsibility, other stuff. And
00:32:41.820
they're like, I've got this like limited window. You know, I really just have like
00:32:45.160
a brief period of time, uh, you know, every day to work on something. So it's
00:32:47.900
got to be one thing. So it's really your, your own, your own personality.
00:32:50.700
Any side hustles from your own life? I mean, I think one of the nice things about
00:32:54.300
the books, you give so many examples, but I'm curious about your own life. Are there
00:32:57.000
side hustles that you've used that were a success that flopped, et cetera?
00:33:01.400
Yeah. I mean, my, like my life has been side hustles and nothing, but essentially, uh,
00:33:05.040
um, because I, I discovered a world of like micro entrepreneurship, essentially like when
00:33:10.300
I was, uh, basically 18, 19 and I learned how to sell, sell things on eBay. And I learned
00:33:15.980
how to buy coffee from Jamaica, found this like reseller online and have it shipped to
00:33:19.920
my apartment and have like coffee, like bags of coffee, like spread out across my living
00:33:24.240
room table. And I'm like repackaging it and then sending it out to people. And it was,
00:33:27.660
it was like so fun. I just, I love the whole process of learning about how to do all that.
00:33:31.420
And then at the time, like eBay was a very new site and it's kind of an inefficient market.
00:33:36.500
So people would sometimes pay more for things online than they would, like you could buy
00:33:39.860
in stores. This is like the early days of the internet, you know? And so I would go to
00:33:43.600
the store and buy like Toys R Us and buy Legos and then would resell them, you know, for 20%
00:33:48.160
more online. So learning about how to do all that stuff, it was just a fun little process.
00:33:51.840
And it's been like literally 20 years of doing, you know, various things like that. And some
00:33:57.220
stuff has worked and some stuff hasn't. You know, I once made this huge mistake. I had built
00:34:02.760
like a really substantial email list for something about like travel related. And at the time there
00:34:07.300
was this whole trend about like automating your business and outsourcing and things and, and
00:34:11.240
like, you know, not being like in the weeds of your business. And so I thought I was doing
00:34:15.220
something smart. I did this promotion, sent out this email and I like walked away and didn't
00:34:20.300
like pay attention at all. And I was really proud of myself. So I was like, I'm going to check
00:34:23.300
back like two days later and I'm going to see like all this money that's coming in. So
00:34:26.700
I checked back two days later and I had sent the wrong link in the email basically. And
00:34:31.900
so, you know, and I, not only did I send the wrong link, which is a terrible mistake, but
00:34:35.680
a lot of people have made that. The bigger mistake was I didn't check for two days, you
00:34:38.820
know? So, so literally I go back and there's like $0 and then a bunch of replies that are
00:34:43.160
like, Hey, the link doesn't work. And I'm like, Oh, okay, great.
00:34:46.020
You know, as you were saying, talking, I thought side hustles are a great way to maybe if you
00:34:50.660
have kids teach your kids about entrepreneurship.
00:34:52.900
Yeah. Yeah. Of course. There's some fun stories about kids that are kids that are doing their
00:34:56.860
own side hustles or families that are doing together. There's like a, it was like a mom
00:35:00.760
and son. Uh, son is really into baseball. And so they actually designed like a designed
00:35:06.300
a new kind of athletic cup because like the ones who was wearing really uncomfortable or
00:35:10.960
whatever. So they actually created this, forget what it's called, but they're, they're actually
00:35:13.560
doing like significant, you know, side income from this and together the whole family,
00:35:17.100
like there's a, there's a sister as well. And then the dad, like all four of them kind of
00:35:20.460
got into the process of learning how manufacturing works and how to like get this stuff made in
00:35:24.520
China and which has some, some costs to it, but it's not like a normal cost that they found
00:35:28.700
out over time, like how to do it kind of on the cheap. And, and now this is like, you
00:35:34.280
That's awesome. Well, Chris, this has been a great conversation. Where can people go to
00:35:38.720
Yeah. Thank you. It has been a great conversation. Um, would love to hear from some listeners
00:35:42.140
sometime. Uh, the book is called side hustle from idea to income in 27 days. Uh, it should
00:35:47.180
be at any bookstore or any online retailer, including Amazon, Barnes and Noble, wherever
00:35:51.100
you shop for books, uh, books, uh, and the website is side hustle school.com. And there's
00:35:56.080
a daily podcast as well called side hustle school.
00:35:58.080
Awesome. Chris Guillebeau. Thank you so much for your time. It's been a pleasure.
00:36:01.460
Like I say was Chris Guillebeau. He's the author of the book side hustle from idea to income
00:36:05.200
in 27 days. It's available on amazon.com and bookstores everywhere. You can also find out
00:36:09.220
more information about his work at side hustle school.com where he has a podcast where he
00:36:13.360
interviews people who started side hustles and digs into how they did it. Also check
00:36:17.200
out our show notes at aom.is slash side hustle. We can find links to resources. We can delve
00:36:32.480
Well, that wraps up another edition of the art of manliness podcast. For more manly tips
00:36:36.220
and advice, make sure to check out the art of manliness website at artofmanliness.com.
00:36:39.700
And if you enjoy the show, you feel like you got something out of it, share it with a friend.
00:36:42.640
And one thing I've discovered when I talk to people about how they discover the podcast,
00:36:46.260
most say a friend or family member told them about it. It wasn't social media. It wasn't
00:36:50.480
Facebook. It wasn't Twitter. So please, I really mean a lot if you tell, you know, a few friends
00:36:55.200
about the show, the more the merrier. As always, I appreciate the continued support. And until
00:36:59.900
next time, this is Brett McKay telling you to stay manly.