The Art of Manliness - #344： The Art of the Side Hustle

00:00:00.000 Brett McKay here and welcome to another edition of the Art of Manliness podcast. If you're

00:00:18.540 looking to pay down debt or save it for a financial goal faster, there are two ways

00:00:21.900 to do it. You save more money or make more money. And let's assume you're knocking out

00:00:25.540 of the park with your frugality, you're saving as much as you can. How can you make more

00:00:28.980 money? We're talking legally here. Well, one way is starting a side hustle. And besides

00:00:33.320 providing you with extra income, my guest today argues that having a small business on

00:00:36.760 the side can actually bring you a lot more satisfaction and confidence to your life.

00:00:40.460 His name is Chris Guillebeau, and I've had him on the podcast before to discuss his book

00:00:43.560 Born for This. Today on the show, Chris and I discuss his latest book, Side Hustle from

00:00:47.680 Idea to Income in 27 Days. Chris and I begin our conversation talking about why every man

00:00:51.920 should have a side hustle, including men who are already very happy with their day jobs.

00:00:55.840 Chris walks us through the process of starting a side hustle from ideation to business formation

00:01:00.780 to marketing. Along the way, Chris busts some myths that people have about starting a business

00:01:04.900 and provides examples of folks who have added $1,000 to $20,000 a month to their income with

00:01:10.100 the business they work on in their free time. Lots of actionable advice in the show. And after

00:01:13.740 it's over, check out the show notes at aom.is slash side hustle, where you can find links

00:01:18.040 to resources, we can delve deeper into this topic. Chris Guillebeau, welcome back to the show.

00:01:32.860 Thank you for having me back. I think it's like the, you know, seventh or eighth time I've been

00:01:36.000 on the show. Not quite seven or eight, but it's a big honor. Yeah. A three, Peter, because you're

00:01:39.740 always coming out of these books. So I got to have you back on the show. The last time we had you on

00:01:43.960 the show, we talked about, you know, building your dream career. And we got a lot of positive

00:01:47.560 feedback from that. Your new book is called Side Hustle from Idea to Income in 27 Days.

00:01:53.520 We've written about side hustles on the site before. We're a big proponent of them.

00:01:57.120 For those who aren't familiar with the concept of a side hustle, how do you define a side hustle?

00:02:02.080 You know, a lot of people are talking about side hustles in a lot of different ways. And I really,

00:02:06.920 I'm glad to hear that you had some good feedback from our last conversation. I actually feel like

00:02:10.000 this new book, Side Hustle, is probably the most relevant to your listeners that I've ever

00:02:13.860 ever written. And I'm trying to focus my side hustle focus or my side hustle push on creating

00:02:19.520 assets, on creating something that you have ownership over. And the reason why I'm doing

00:02:24.960 that, well, one, it's just smart. But then also, I feel like in the culture, some people are talking

00:02:29.380 about side hustles as part of the gig economy or as part of like, you know, the notion that people

00:02:34.820 have to have two or three jobs these days. And I'm not really trying to encourage people to work

00:02:39.240 harder or to do a 40 hour a week, you know, job and then go and do a 20 hour a week job somewhere

00:02:44.380 else. I'm trying to help people create something that they can point to and say, you know, I have

00:02:48.860 ownership over this thing and it's making money for me. And maybe I never wanted to be an entrepreneur.

00:02:54.320 Maybe I still don't want to be an entrepreneur. But it's really great that, you know, at the end of

00:02:58.460 the month, I can have my paycheck and I can have this extra income coming in. And that just feels

00:03:02.240 really good. So that's what I'm trying to help people with.

00:03:04.440 So there's a lot of reason people start side hustles. And I think you argue that everyone

00:03:08.540 should have a side hustle. Even if you got a satisfying career, you love your job, you should

00:03:12.620 still have something on the side. Why is that?

00:03:15.260 You know, I've never felt more strongly about something, I think, and about this concept in

00:03:20.280 particular, because I am not trying to encourage people to go out and quit their jobs. Like I did

00:03:26.060 that a little bit with a previous book, $100 Startup that I wrote and kind of learned through that

00:03:30.320 process like that book resonated with a lot of folks. And a lot of folks said, well, that's not

00:03:34.300 really me. I actually love my job, you know, or maybe eventually I want to quit my job, but I

00:03:38.520 can't do that right now. Everybody needs to have more than one support for them, though. I think

00:03:43.780 it's smart for security. I think it's good to have a backup plan. It's good to have more option

00:03:49.100 freedom. There's really no downside to it. I feel like if you invest in this process the right way,

00:03:55.780 and by invest, I'm talking mostly about your time, not talking about spending money,

00:03:59.320 then I feel like only good things come from it. You know, and like I said, it gives people

00:04:04.500 confidence, makes them feel empowered. And of course, it's extra money. So, you know, one way

00:04:09.020 to look at it is like, oh, look at what's happening in the world and the economy and people don't have

00:04:12.600 security and traditional jobs. All that is true. I agree. The other way to look at it, in addition,

00:04:17.460 is to say, well, this is something that's, you know, creative, empowering, makes you look at it and

00:04:23.000 say, like I mentioned, you know, I made this thing, I own it. And it also can be fun. It can be

00:04:28.540 something that you look forward to doing. You know, it's not something you dread. It's something

00:04:31.600 you look forward to doing at the end of the day or your 20 minutes in the morning or whatever time

00:04:35.460 you have for it. Yeah. I think that last point is a good one because a lot of people who,

00:04:39.720 they might not hate their job, but it's not giving them the creative outlet that they might

00:04:44.500 are desiring. Like a side hustle allows them to do that and also make money in the process.

00:04:49.780 Yeah. Yeah, exactly. I talked to a guy last night. I'm on this tour to do 100 cities,

00:04:53.880 talk with people about side hustles. And I generally think it's good to do something a little bit

00:04:58.040 different for your side hustle than you do for your day job. And I did meet someone last night

00:05:02.680 who was like, oh, I'm a web developer by day and I'm a web developer at night. That can work. I mean,

00:05:07.320 some people do that. What I tend to see people just having more enjoyment with and maybe even more

00:05:11.780 success with is something that's totally different. So there's a story I did recently about a guy who's

00:05:16.240 a managerial accountant and his side hustle is producing poetry slams. And he makes like a thousand

00:05:23.080 dollars a month, you know, putting on these poetry slams, which is great because you never hear

00:05:26.180 about a poet making money. Right. But then also like he's the, you know, accountant by day,

00:05:30.240 poet by night. So totally different kind of thought process and work and creative outlet,

00:05:35.660 like you said.

00:05:36.200 What does it take to start a side hustle? Does it require a lot? Because I think a lot of people,

00:05:40.420 you know, because it's a business, right? And I think people think, oh, there's a lot of hoops

00:05:44.100 I got to jump through. What does it actually take to start one?

00:05:47.340 Right, right. Yeah. It basically takes all your life savings and you need to go back to school for

00:05:51.840 four years. And yeah, no, it takes none of that. What I'm trying to do with the book and the tour

00:05:57.840 show people this process and the process is idea to income in 27 days. So I really am encouraging

00:06:04.780 people to like get this, get this thing started quickly. And as I said, it's not about spending

00:06:09.720 money. It's also not about this extensive planning phase as well. So basically what it's about is,

00:06:15.240 is helping people use the skills they already have to, you know, create some kind of product or

00:06:21.440 service. And I think that's, that's key because people tend to think about business ideas, you

00:06:26.240 know, quote unquote, and people, consumers, like all of us, we don't buy ideas. Like we buy products

00:06:31.200 or services. So I'm helping people like look at the skills they have and figure out how can I package

00:06:36.040 that into some kind of product or service? How can I then turn that into some kind of offer?

00:06:40.880 And then how can I get that out to the world? Probably before I'm ready, you know, so that I can get

00:06:45.520 some real world feedback, not just asking my buddies like, Hey, what do you think about this idea?

00:06:48.920 But putting it out and seeing how people really respond and then kind of regrouping from there.

00:06:53.720 So, you know, 27 day process, it's, it's broken out into like five weeks. You know, you do one

00:06:57.980 thing a day. As I said, 20 to 30 minutes a day. And at the end, you should have some, some real

00:07:03.580 results and you should be able to actually point to something and say, look, that's, that's my side

00:07:06.840 hustle. So let's talk about the start of the ideation process. Where can people get ideas for side

00:07:11.580 hustles? A lot of people are like, I want to start a business, but I don't know what to do. So where can

00:07:15.920 people find these ideas? Yeah. It's really interesting. I've learned through a lot of

00:07:18.900 research and like, you know, eight years of working on this in different ways that half

00:07:22.500 the people struggle with, with that, what you just mentioned, like, where do ideas come from?

00:07:26.480 I don't know what I have. That's a good idea. The other half of the people struggle with,

00:07:29.760 like, I have an idea. Ideas aren't my problem. I just don't quite know what to do next. Or I can't

00:07:33.520 choose between different ideas. So the first part, because like the book goes through both sections.

00:07:39.600 So learning where ideas come from is essentially a skill that, that nobody really learns in school.

00:07:45.020 Your parents didn't teach you, but it's not that hard to develop. So it's essentially about

00:07:48.680 developing your skill of curiosity or developing the power of observation and just beginning with

00:07:55.080 paying attention. So paying attention, first of all, to daily life, like as you kind of go through

00:07:59.800 the world, looking around and noticing not just things that you like, but what things do you not

00:08:05.220 like? And, you know, what frustrations do you encounter? What problems do you encounter? Like,

00:08:09.980 how could, you know, somebody create some kind of a solution to something? The second part is

00:08:14.840 also then looking at yourself. What are your skills? What are all your skills? It's not just

00:08:19.560 skills that you use, you know, for your day job or what you got your degree in if you went to

00:08:23.320 college. But what is something that we can actually like combine with these two things,

00:08:27.860 like your skill, your background, your interests, and then also like some kind of problem in the

00:08:32.000 world or something that, you know, can then turn into, as we've said, a side hustle. So I try to walk

00:08:37.380 people through all these different examples, you know, of like, okay, here's how this person did it.

00:08:42.100 And hopefully that gets you thinking, because you're not going to do the same thing that they

00:08:45.200 did or that I did or anybody else. But through this process, hopefully, you can get, you know,

00:08:50.440 the ideas that you need. And say you get some ideas, how do you determine if it's feasible,

00:08:54.780 right? Because like, you might have this idea, you think it sounds great on paper, but then,

00:08:58.720 okay, actually, I'm going to lose money trying to make this a business. So how do you figure that

00:09:03.700 out before you make too much of an investment of time or money into it?

00:09:07.280 Sure, sure. Well, I'll say two things about this. You know, one, one to your direct question,

00:09:11.640 like there is a process that I show in the book about how to test your idea with $10 in a Facebook

00:09:16.040 account. And it's this really simple process of basically like, you know, writing an ad and kind

00:09:21.200 of just kind of seeing how people respond. It's not that difficult to set up. And as I said,

00:09:24.740 it costs like $10. However, I'll also say that, like, I have this daily podcast called Side Hustle

00:09:30.680 School. And every day on the show, seven days a week, a story of somebody who does this. And so telling a

00:09:36.600 story of an employee who starts an income generating project without quitting their job,

00:09:40.920 how'd they get the idea? You know, what happened? How'd they develop it? What challenges did they

00:09:45.620 encounter? How much money did they make from it? And what I have seen is that it's actually not

00:09:50.260 always possible to like, to know in advance, like if this thing is going to work, or it's not possible,

00:09:55.600 not always possible to know if your ideas is going to be validated. And so sometimes you just have to,

00:10:01.060 you just kind of have to try. And that's why the process is short. That's why it's, you know,

00:10:05.280 27 days so that you're not, you know, investing a huge amount of time or spending a year planning

00:10:10.240 something that you don't know if it's, if it's going to work or not. So I like, I like to feature

00:10:13.380 a bunch of like quirky kind of different stories. Like the book begins with this guy who wrote a blog

00:10:18.060 about fish tank reviews and like, he was really into fish. And so he spent like a weekend, like a short

00:10:23.360 period of time, like writing these fish tank reviews and linking to Amazon where he had an affiliate

00:10:28.500 account, which anyone can create. And he kind of went away and didn't really think much about it.

00:10:32.840 And a month later, he got a check for $300 in the mail. And he's like, Oh, okay. You know,

00:10:37.100 that's, that's interesting. And so he put a little bit more work into it, but eventually kind of left

00:10:41.320 it because he was a construction project manager and busy guy. So the short version of the punchline

00:10:46.280 of that story is this was like three years ago and three years on, like literally every single month,

00:10:51.900 he's been getting a check in the mail from Amazon for $700. So $700, you know, is not a necessarily a

00:10:58.640 life-changing amount of money. You can't live off of it, but it's very significant,

00:11:02.000 especially for something that you don't do anything for. Right. So he's been able to take

00:11:06.800 his wife on extra vacation every year and do all this kind of stuff. If you had tried to like

00:11:12.340 validate the fish tank review idea before he started it, I don't know if you, if you could,

00:11:16.220 you know, I think a lot of people would say that's kind of a dumb idea, but you know, obviously it

00:11:20.080 worked out pretty well for him. Yeah. $700 a month that would pay for rent in a two bedroom apartment 0.62

00:11:24.260 here in Tulsa, Oklahoma. Yeah. Right. Right. Think about that. Yeah. Or help you pay off debt.

00:11:28.700 You know, I hear from a lot of people that have student loan debt or credit card debt or,

00:11:32.300 you know, just, just whatever. It's like, it's, it's, it's a real thing. And so that's why I

00:11:37.040 actually like for the show and for the book itself, I have this minimum, like you have to be making at

00:11:41.060 least $500 a month, you know, to be featured on the show or every story in the book. And actually my

00:11:46.720 goal for people, if like you, if you go through the book and you go through the process, like I'm

00:11:50.620 personally not going to be satisfied as the author, if, if the project you create is not doing at least

00:11:54.340 $500 a month. And there's a lot of stories, uh, you know, in the book of people who've gone on to

00:11:58.780 actually do, you know, six figure side hustles or much more. And I love those stories too. Um,

00:12:03.540 we could get into those, but I think like, it's also relatable in some ways to, to point to people

00:12:07.660 who are like, you know, $500, $1,000 a month. So the idea is that a side hustle idea, like you,

00:12:13.180 you should invest so little into it that it's okay. If you invest some time or some money,

00:12:18.020 because it's so little that if it flops, it's not that big of a deal.

00:12:21.060 Yeah, exactly. The risk is low, right? And this is, this is like a counterpoint to traditional

00:12:25.620 entrepreneurship because traditional entrepreneurship is all about, oh, you're going

00:12:29.060 to take a big risk. You might get a big reward. You know, you're like trying to start this startup

00:12:33.540 or whatever it is. You know, maybe there's like this huge reward that waits, that awaits on the

00:12:37.940 other side, but there's also like this huge chance, a chance of major failure. And I'm trying to like

00:12:42.980 take that, that huge chance of failure out of the process, um, so that people can, can experiment.

00:12:47.800 And I think of it like a, like a hobby. It's like a hobby. It's something you look forward to. Like

00:12:52.540 we said, it's something you enjoy. Maybe you'll spend a little bit of money on it, but you spend

00:12:56.080 a little bit of money on your hobbies. Right. And this, this has the potential to be a hobby that

00:13:00.640 actually pays you money. Right. So that's the, that's the key. Yeah. I mean, here's two examples

00:13:04.420 from my own life of side hustles that didn't cost me any money. Um, one was a success. One was a flop.

00:13:09.760 So when I, I lived in Mexico for a few years, so I speak Spanish fluently, not so much anymore,

00:13:14.240 but when I was in college, I, um, offer tutoring services. So I just, all it is, I printed off a

00:13:20.660 little flyer and hung it up in like where all the Spanish classes are at and didn't cost me anything.

00:13:26.260 And like within a week I had three clients pay me 20 bucks a week for Spanish. And it took me like

00:13:32.000 three hours a week and I was making 60 bucks a week extra and cost me nothing. The other side hustle

00:13:38.320 that I tried was like when iPods first came out and people like had all these, I had like these

00:13:44.460 digital files or they had CDs with all their music. And like, I, I tried to like offer a service where

00:13:50.920 I would rip their CDs and put them onto their iPod. I just printed a flyers and I like just hung up on

00:13:56.380 the doors. Didn't, I spent maybe like two hours and no money basically. And that didn't go anywhere.

00:14:02.660 I didn't get any bites from that, but it was no, no harm, no foul.

00:14:06.640 Exactly. Yeah. I mean, both examples, like you, you printed some flyers, you know,

00:14:10.360 like a small investment of your time and one of them, one of them worked and one of them didn't,

00:14:14.520 you know, that's good. And you're not, like I said, there's no other startup costs to that,

00:14:17.920 like none at all. So, so that's good. Yeah, that's good. I mean, so can I maybe make a quick

00:14:21.780 comment on that, that first example? Um, you know, there you're obviously using a skill that you had.

00:14:26.980 It was something that other people clearly needed and desired. They needed help, you know,

00:14:31.240 with like improving their, their Spanish language skills. And in the second example, like you thought there

00:14:36.040 would be a need, or you, you, you wondered if there would be, and it turned out there, there wasn't.

00:14:39.840 So I have this concept of, um, like starter ideas and next level ideas in the book. And I think your

00:14:46.880 example of like the tutoring Spanish is, is a great example of a starter idea. And when I say starter,

00:14:52.000 it's not any kind of negative, you know, context at all. Uh, it just means that it's, it's a fairly

00:14:56.960 limited idea in terms of like the scope and the scalability of it, because you can only tutor so much,

00:15:02.620 uh, people can only pay a certain amount of tutoring. Like you could, you can probably raise

00:15:05.720 your rate at a certain point, but you can't raise it indefinitely because eventually somebody's just

00:15:09.660 going to go to another Spanish language tutor. So what I'm trying to help people do is like

00:15:14.260 definitely experiment with the starter ideas. That's great. Like you can sell something on Etsy,

00:15:18.960 you know, tomorrow you can sign up for the platform Fiverr and like offer some kind of service tomorrow.

00:15:24.400 Um, but you know, the challenge there is like, you're going to be kind of locked into somebody else's

00:15:28.940 environment. Like you have to kind of play by their rules. Like they essentially can cap your

00:15:32.980 income in some ways, just like driving for Uber or Lyft or whatever. So next level idea is something

00:15:37.960 that you actually like do have this ownership over. Um, it's something that has the potential to earn

00:15:43.760 a lot more money. So very quick story about another guy who was also like, he was actually trying to

00:15:48.080 learn Spanish and he had lived in Argentina for a while and I got somewhat proficient, but then he moved

00:15:53.800 back to Canada and like was, was kind of losing his skills. And so he downloaded an app and like,

00:15:59.680 he liked the app. I think it was Duolingo. He said it was good, but he'd also felt kind of impersonal.

00:16:04.240 And then at the same time, one of his, one of his buddies was like, uh, also trying to like brush

00:16:08.760 up his Spanish and hired a tutor on Craigslist, which is kind of like what you were doing. And

00:16:12.620 he liked that process, but he was paying $25 an hour for it. So I thought this isn't super

00:16:17.140 efficient either. So short version is this guy, I think his name is Sean. He created a,

00:16:22.040 he created a platform that essentially allows like Skype language lessons, you know, from people

00:16:27.660 in the U S and Canada back with, you know, people in Argentina or Chile or elsewhere. And so then

00:16:32.480 there's like an economic difference in terms of the cost and people can log on at any time. They

00:16:37.740 don't have to like coordinate on meeting with Starbucks or whatever. So this project has

00:16:42.400 actually super, super taken off. And within a year, it's actually more than $150,000 that he's made

00:16:47.360 from it. So that's kind of like a difference between a starter idea and something that could

00:16:50.780 potentially go on to do much more. Right. The other idea, the next level idea that I thought

00:16:54.520 was good was the Uber driver became an Uber driver coach, which was interesting.

00:17:00.340 Yes. Yeah, exactly. That's a friend of mine named Harry Campbell, actually here in Southern

00:17:04.280 California where I'm talking to you from. And, uh, it's exactly what you just said. He,

00:17:08.940 he was an Uber driver and was interested in, you know, learning more about how to, how to do a better

00:17:14.560 job and how to increase his hourly rates and, you know, get his rating higher and stuff like that.

00:17:19.360 And so he's, he's like Googling to try to find this information feeling frustrated because there's

00:17:24.220 not a ton of stuff out there. And so he decides to actually create this platform called, you know,

00:17:28.920 the, the ride share guy. And so on this platform, which he's now built out over, I think about two

00:17:33.300 years or so now, um, you know, he has, he has coaching sessions that he does. I think he has some

00:17:38.160 kind of product. He's also like, you know, speaking in the media a lot about it. So he's built this

00:17:41.920 whole authority. So, uh, he, you know, he went from driving to for Uber, which is a good starter

00:17:46.100 idea. Like you have some flexibility over your hours, et cetera, but it's also kind of limited

00:17:50.700 because of competition and the rates are set by Uber, not by you. Now he's gone to this thing that

00:17:55.340 is, it is more entrepreneurial in the sense that he can do whatever he wants and he can take that in

00:17:59.560 lots of different directions. So let's say you, you, you narrowed on an idea. It's feasible. You

00:18:04.980 think you can make a good go at it, but you, in your research, you discover that there are other

00:18:09.240 people who are doing pretty much the same thing that you're doing, right? Like, I mean,

00:18:13.380 that example of the guy with the app, the Spanish app, I mean, he, he able to find, he was able to

00:18:18.700 find a way to tweak that a bit, but let's say there's no way to tweak your side hustle. There's

00:18:22.400 like a lot of dog walkers in your town. What do you do in that case? Should you go ahead? Or she's 1.00

00:18:27.300 like, okay, I'm going to do something else. Well, you know, I guess I would, I would say to that

00:18:30.920 example, like, are there a lot of dogs in your town? Because, you know, one dog walker can't serve

00:18:35.820 the whole market. And in a lot of ways, seeing that somebody else is, is, you know, doing your ideas

00:18:41.240 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 0.86

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

00:23:38.200 know, then reach them essentially.

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.

00:26:02.800 Does he still have his day job?

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

00:26:47.940 without fear.

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

00:28:38.460 rational, logical decisions.

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

00:29:02.660 might exist?

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

00:31:05.820 you make that decision, but not before.

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

00:31:27.600 money for that.

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%

00:32:17.560 because it's going to eventually be due.

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

00:35:32.660 know, four years in like business.

00:35:34.280 That's awesome. Well, Chris, this has been a great conversation. Where can people go to

00:35:37.300 learn more about the book?

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.

00:36:00.740 Thank you, sir.

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

00:36:21.660 deeper into this topic.

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.

00:37:12.640 you

00:37:18.260 you

00:37:24.660 you

The Art of Manliness - October 03, 2017

#344： The Art of the Side Hustle

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