The Rich Roll Podcast - Chris Guillebeau On Why You Need A Side Hustle (Even If You Love Your Job)

Episode Date: October 2, 2017

Maybe you love your job. Perhaps you don't. Either way, there's wisdom in cultivating a side hustle — not a second job, but a self-styled income-generating project you cultivate in your free time. Why do I need this? Ask Choose Yourself! author (and podcast guest) James Altucher and he'll wax rhapsodic about the precarious nature of conventional career paths and the misplaced trust we invest in their long-term security. Invest in ownership. For some, the thought of quitting their day job to pursue the entrepreneurial life is exhilarating. For most, however, this is a terrifying prospect. And not everyone has the means or the desire to take on the risks and responsibilities of working for themselves. But Chris Guillebeau contends it's not an either or scenario. Not only can you have both, you should. As traditional career trajectories give way to the rise of our freelance economy, it's wise to diversify your income stream. But creating something on the side entirely your own isn't just about extra cash. And it's not really about becoming an entrepreneur (because most people aren't). It's also about cultivating purpose. It's about elevating your sense of direction. And imbuing your path with greater personal meaning. A master of unconventional, purposeful living, Chris is a widely acclaimed author, blogger, entrepreneur and modern-day adventurer. Ripe with wanderlust after a 4-year stint as a NGO volunteer executive in West Africa, he embarked on a multi-year quest to travel to every country in the world, all 193, before his 35th birthday. Along the way, Chris began sharing his adventures on a newly hatched blog. What began as a rather ignored and somewhat turgid travelogue soon morphed into The Art of Non-Conformity, a globally revered portal that chronicles Chris' personal experiences and the wisdom of a dynamic multitude of unconventional people overcoming conventional social mores around work, life and travel to achieve personal goals and greater life satisfaction outside traditional paradigms. Enjoy! Rich

The manifesto of this book is that you need a side hustle. You need more than one source of income, even if you love your job. And it's not that hard to do it. There's a process. And if you've tried to do it before and you failed, well, I've failed at lots of things. But you should try again. You don't have to spend a lot of money. You don't have to go out and acquire a ton of new skills.

If you're not an app developer, don't try to develop an app. Just figure out what you're good at and find a way to translate that into something. Chris Guillebeau is back this week on the Rich Roll Podcast. The Rich Roll Podcast. The Rich Roll Podcast. Hey, everybody. My name is Rich Roll. I am your host.

This is my podcast. Welcome to it, the show where each and every week for the last five years, I have dug deep to bring you compelling conversations with some of the most inspiring paradigm-breaking changemakers all across the world. And today, I got a treat for you. I sit down once again with the amazing Chris Guillebeau. Long-time listeners will remember our first conversation from, I think it was September of last year, episode 247. And that was a conversation all about how to live an unconventional life, about the art of nonconformity. And if you missed it, it was deep. It was honest.

I highly recommend you guys check it out, especially if you missed it, it was deep. It was honest. I highly recommend you guys check it out, especially if you're new to Chris as we go into his backstory in depth on that occasion. For those newer to the show, Chris is the author behind a number of books you may know well, including the New York Times bestselling $100 Startup. I still see this book in every airport bookstore all over the country. The Art of Nonconformity, Born for This, and The Happiness of Pursuit. Chris is also a modern-day explorer. He visited all 193 countries before the age of 35, and he runs one of the most widely trafficked blogs on the internet, The Art of Nonconformity at chrisgilbo.com, where

he writes about how to live an unconventional life in a conventional world. In addition, Chris is the founder and ringmaster of something called the World Domination Summit, which is a truly spectacular conference held annually in his hometown of Portland. I had the honor and the pleasure of being a keynote speaker at WDS this past summer. And I can honestly say, as somebody who has spoken at a lot of events, it was one of the most impressive, professional, and moving experiences of my life. You guys should all check it out next summer. Today, Chris and I hone in on a specific topic, the hows and whys behind developing a side hustle. The title and subject of his daily podcast,

as well as his brand new book of the same name, it's all about why in this current economic climate, and even if you love your job, we can all benefit from cultivating our creative entrepreneurial flair in our free time as a way to create more ownership and bring more purpose and personal meaning into our lives. So even if you're not an entrepreneur, and don't feel bad if you're not, most people aren't, Chris's advice and his wisdom on this subject is apt, it's applicable to all, and I think you guys are going to really enjoy this one. We're brought to you today by recovery.com.

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Life in recovery is wonderful, and recovery.com is your partner in starting that journey. When you or a loved one need help, go to recovery.com and take the first step towards recovery. To find the best treatment option for you or a loved one, again, go to recovery.com. Okay, Chris, our time was a bit limited on this one. I met up with him in LA just before he gave a presentation as part of his 100 city tour for his new book side hustle. But I did my best to make the most of the time. Uh, we talk about his WDS conference and my experience speaking there this past July.

We talk about why everybody should explore having a second income besides their day job. Even if you love your job, it's not about becoming a full-fledged entrepreneur. It's about figuring out what you love, why you're good at it, and developing a practical way to turn that into some passive income. And we also talk about his recent foray into the world of podcasting, how he manages to write books, blog, produce the World Domination Summit, and put out an amazing podcast every single day, seven days a week. He puts up a new podcast episode every day, which is insane given that doing one to two episodes a week for me is essentially a full-time occupation.

Finally, I mentioned this before, but it's worth repeating. I'm back making videos. David Zamed and I are putting up about two to three new ones each week going forward. We have big plans for the future, including eventually moving into full video versions of the podcast on YouTube. And I just posted a vlog type video that takes you behind the scenes of this very podcast and my day in general. It's called It Always Gets Done, and you can find it at youtube.com forward slash richroll. I'm also going to embed it on the episode page for this episode at richroll.com. Okay. Like I said, Chris is one of my favorite people. He's warm. He's real. He's

just one of those stellar, empathetic humans that you want to hang out with and talk to all day. So let's spend an hour with them. Well, cool, man. It's good to, uh, it's good to see you. Thank you for making the time. Awesome. Thank you for having me. Yeah. So you're on day three of your a hundred city tour. Actually, yeah. Yesterday was Seattle and, uh, here we are in Los Angeles. So stop number two. Right. And you're only here for like a day, right? Yeah, pretty much once a day. actually yeah yesterday was seattle and uh here we are in los angeles so stop number two right and you're only here for like a day right yeah pretty much one city a day uh-huh it's that so that's how it's going to work going forward just literally oh man yeah it's usually five or six cities a week

usually i mean i i think that would test even the most seasoned of travelers like yourself as somebody who's flown everywhere to every country and and the like but i know that you love it right you love to travel well it's like i was saying it's all i got rich you know it's like it's all i don't do ultra marathons all you got i don't do all the crazy stuff that you do so this is my endurance event uh-huh and um embrace it yeah absolutely no i love it it's good it's good like i love getting on an airplane i do too it is the closest thing to time travel that we have in our culture and i just i love airports i like getting to the airport early i like same everything even when it's delayed like with all the hassle that comes with yeah you know commercial you know air air travel i still love

everything about it because it's it's packed with possibility you know it's like it's exciting even when you're doing it all the time like i look forward to it when people are like oh all the travel it doesn't get down i'm like no like sitting on a in a window seat and looking out the window as you're taking off and i mean it's the best it would be really hard if you didn't look forward to it right like all the travel that you have to do i guess there are a lot of people that are in that situation i mean i knew one guy another guy who's trying to go to every country in the world and he asked me for advice and he was like yeah i really just don't like the travel i really don't like the i'm like okay this is the wrong thing this is the wrong

thing dude basically like find something else because yeah right that's funny man well before we get into talking about side hustle and and you know the new book which i'm very excited about great job by the way it's a beautiful work of art that i think is going to help a lot of people. Um, I have to say that, uh, I can't believe what you have created with world domination summit. So glad you're able to come. Thank you for asking me to come and speak. It was really, uh, an extraordinary experience, not just an honor to be able to like share the stage with so many amazing speakers, but, and, and to get to know you know these amazing uh this collection of people that you you know sort of uh cultivate and and curate every year but also

like your community man just getting to know the people that you know weren't just there that year but like attended year after year after year after year like some of the coolest people like i've ever met like you've built like a really beautiful thing well it feels like it's kind of like the travel i feel fortunate that I can do it. Like it's just, it's great. So I'm really glad you were able to join us as well. I know that, uh, the community really responded very well to your talk. I've actually heard from several people that have made changes in their diet and lifestyle

from, from as a result of your talk. So good. Yeah. That's good to hear. That's good to hear. I mean, you know, that is how many years into it are you? You're seven. You're seven.

We're just, right. And when you began that, I mean, could you have foreseen? Like you have this beautiful opera house. You've got 1,200 people. There's not an empty seat in the house, and everybody is so engaged. Like how did that start, and how did you continue to kind of fertilize that so that it could become what it has become? I don't think I could have foreseen that or,

but that's also the through line and everything that I've done. Maybe some of the things you've done as well. Like do you really have this, this vision of what your life is going to be like? And especially when you take on these kinds of projects, like I think the more you do them, then the more confidence you get and the more you're like, Oh, that was hard, but what's next? You know,

I'm always looking for what's next. So as for how it began, you know, it's funny because people do sometimes ask, like, you know, how can I put on an event? What do I need to know? You know, how do I get hundreds of people to come? The true story is, like, for that first version of World Domination Summit, 2011, the year before I had published my first book, The Art of Nonconformity, and I did a tour to all 50 States. It was kind of a precursor of what I'm doing now,

you know? And, um, I went to all 50 States because I was like going to every country in the world. So it just seemed like the right thing to do for book tour. And so I would go and I would personally invite everybody. That's the point.

I would go, but it's satisfied your obsessive compulsive nature, like every state because every country, right. Right. And every province in Canada also, you know, and and also it was there was a connection with community and like if there's somebody in you know nebraska or north carolina or not just north carolina but let's say north dakota or west virginia are places that most people don't go to do events so i would go to

these places and i would personally invite people i would say like hey we're doing this thing next year it's called world domination summit and that's about all i had i about all I had to say about it because I didn't know how to put on the bed. Didn't have much more of a description. Um, it's going to be really cool and you should come basically. And so I'm personally inviting everybody. And so I tell that story because people are like, how do I get people to sign up for an event?

Like you just go to all 50 States and personally invite people. It's on the ground, man. That's it. Yeah. And then that, that brought, you know, 400 people. Um, and that was like a three month effort, you know, and then that that brought you know 400 people uh i mean that was like a three-month effort you know and then 400 people came the next summer and then um i think we did a decent job with the first event because like most people pre-registered to come back for the

following year and that kind of grew from from there yeah yeah i mean i like that you know example of of the leap of faith and and you, you know, managing, you know, expectations and just being like, is this about getting one person, you know, one person at a time, traveling state to state to state. I think people, it's easy for people to, you know, attend an event like yours and go, well, this is what I want and not appreciate what went into cultivating that all the care and the love. And I can't imagine the obstacles and the setbacks you must have faced doing it. And every year it's like, it's, it does take a lot of, of my time. And, um, I kind of wonder sometimes, like usually in the spring we hit this lull period,

like we have this like periods of momentum and there's a period of kind of lull and like, wow, this is a lot of time we're spending on this, but then we actually do the event and, you know, see all the people that come and hear the stories of how they're impacted. And it's, it's totally worth it. So I really like how there's an integrated component of service and giving back. That's like built into the fabric of it. Like when you brought all those people up on stage and talked about, like, I forget what it's called, but that package that you put together for, uh, newly settled immigrants to help them integrate into the culture? Like, talk about that a little bit, because I'd never heard of that before, but that was

like a really beautiful thing. Yeah, well, this year, our theme was building a better world, just kind of in response to a lot of stuff that's been happening in the world. And every year, we try to do something pretty significant. And this year, we did focus on this notion of immigration, in particular people that were being resettled to the Portland area because we're based in Portland. And obviously we have attendees coming from around the world, but a lot of them feel a connection to Portland because they've been coming year after year. And so I just got to know this agency that is doing

work with families that get resettled. And they're often from Iraq and Afghanistan, Somalia, places like that. So they come to the U.S. and they get a bit of support they get support from the government for like six six months and during that time they have to you know find work and learn English and do all kinds of stuff like it's a monumental task right so one of these agencies that we got to know partners with the resettlement groups and gives them like what they call a restart kit and so the restart kit is essentially everything you need to like have a new apartment, basically like all the bedding and linens and your dishes for the

kitchen and like, you know, everything you would need to set up your first apartment, but it's for a family. And so we as a WDS community are taking that mission on essentially to provide that for all the families over the next year. Wow. But it's fun. It's good. Like it's service, but it's also, we're excited about that. It's great. Like I think it's really good because you hear all these messages about immigration and refugees and you know you always wonder like well what do um what do people perceive

about us you know it's not just like our perception of them like think about overseas like everybody has social media you know people in somalia have cell phones they hear the news and so when these families can be resettled like they're taking pictures of like their stuff look at this stuff we got you know americans you know gave us this yeah yeah and counter message the the positive impact of that is so immediate right right you know what i mean when you deliver that like it has an impact it's it's it has a very tangible um significant you know short-term impact on getting these people up on their feet. So I just love doing stuff like that. I just, whether it's my personal stuff,

travel or whatever, or stuff like that, I just think it's, it's interesting. It's good. Yeah. All right. So I want to talk about side hustle. And I think, I think maybe an interesting way into that is to kind of talk about the shifting tectonic plates of the workforce at large and how our economy is changing and our relationship with work in the workplace is, you know, evolving as a result of technology and forces beyond our control, et cetera. Cause I think that informs, you know, the why behind you writing this book. Sure. Sure. Yeah. I mean, there's a, there's a lot there. There's a lot to unpack with that. so it depends on where you want to where you want to start yeah well i think this idea that um that was kind of raised in james altucher's book choose yourself in that you know this idea of job security is now kind of an illusion this idea that you're

going to work for a company and you know work there for 40 years i mean this is not the reality for most people anymore and in fact this notion that you're going to get a job and have some level of security is also, um, you know, getting tossed out the window to a certain extent. And, and I think that puts pressure more on the individual to take greater responsibility and to be more fluid and flexible with how they're, they're thinking about their career long-term. Yeah. There. Yeah. There's a New Yorker cartoon that I show in my presentation for the Side Hustle Tour, and it shows two college graduates talking to each other, and one of them is saying,

what kind of job do you hope not to get after graduation? Right? You know? So there is that. I agree. I think maybe where I come into the picture is I've been writing about this kind of stuff for about eight years.

I mean, this is my whole life. I've done side hustles. I've always worked for myself in one way or another, but I think what is shifting is not just those things. I think that's been happening for a bit. I think there's a bit of a backlash to the idea that everyone should be an entrepreneur and that's probably where the side hustle thing comes in because I feel like, yes, even though there's not great job security, et cetera, there's a lot of people who are actually kind of happy in their jobs. And I feel like they have

been largely ignored by the whole entrepreneurial culture. Every business startup founder, then you should be ashamed of yourself. Exactly. Exactly. Like I really do perceive that people, you know, feel that. And so a lot of the books, a lot of the resources that are out there are kind of like, hey, quit your job, you know, quit your job, jump off a cliff, you know, reinvent yourself, fire your boss, et cetera. And I'm partially guilty for this, you know, because like I wrote a book called The $100 Startup, which had a subtitle like fire your boss, I think. So I didn't pick the subtitle, by the way, the publisher did, but still. So I guess still the bug stops. I know, I know. Exactly. The publisher did, but still.

It's still the bug stops with you. I know, I know. Exactly. So I feel like last year I did this tour for another book called Born for This. And I noticed that people responded disproportionately to this concept of having a side hustle. That was like two minutes of my 30-minute talk. And I got so many questions about that. And the message was and is now, you know, you don't have to quit your job. In fact, you probably shouldn't quit your job without a safety net. And if you love

your job, that's great too. But even if you love your job, you should have more than one source of income. And so I've created this process, you know, it's called from idea to income in 27 days, so that busy people who don't necessarily want to be entrepreneurs, right, you know, can still create that extra source of income. Yeah. And it's, it's, it's cool. It's cool. Whether you love your job or you're very disaffected in that, you know, and, and, and, and, and thus, you know, are being provided an outlet to, you know, be more of who you would like to be through that, you know, external pursuit outside of the nine to five so walk us through it like

you kind of have this i mean you have you have you know this this program this 27 day program baked in that you kind of take people from you know inception through you know execution which begins with essentially like cultivating ideas Yeah. There's a lot that goes into it before you're making any decisions about where you're exerting that energy. Exactly, yeah. So I've noticed in a lot of research and conversations that people tend to struggle with one of two things

when they're trying to do this for the first time. And the first thing is, I don't have an idea. Like, I don't know what idea is good for me. Like, I don't know what kind of side hustle do I start. And I have skills, but my skills seem to be kind of confined to my career or to my degree or whatever. So how do I find ideas? Right. And the second problem is I have ideas. Ideas are not my problem. You know, I, maybe I have too many ideas. I just can't figure out what to do next. I don't see the logical order of going from where I am to where I want to be. And so I try to design the program to address both of those concerns. And the first one is about

understanding where ideas come from. Where do good side hustle ideas come from? So where do they come from? From observation, from curiosity. And these are skills that are not really taught, but they're also not that difficult to learn. So a lot of the stories that I feature on the podcast and in the book are kind of quirky or unusual. I'm not really featuring internet marketers for the most part. I'm not featuring celebrities.

I'm not featuring people who are known. No, these are everyday people. And I think that it comes across in the podcast very well like it makes it very accessible and it allows the the listener or the reader because you know the stories overlap to be able to connect with that journey yeah i mean that's the goal the goal is to is to present people who are relatable so that your objections are countered essentially so you're like well, well, I can't do that because Chris did that or Rich or somebody else had some advantage. Okay, well, then what about this next person and this person after that?

And this person after that. So tell the great story about the fish tank guy. Oh, the fish tank guy. Yeah, actually kind of kick the book off of that story. And it's the story of this guy in the UK actually. And he's really into fish you know likes fish so I guess if you like fish and you know a little bit about fish tanks and if you're ever going to have fish probably the first thing you're going to google is like fish tank right or fish tank review

or buy fish tank or something so a few years ago and this guy was like a construction project manager or something so a few years ago this guy sets up a little blog, like a very simple WordPress blog, um, providing reviews of fish tanks, you know, and different little write-ups of why this fish tank is better than the other one or whatever, you know? Um, and then he, you know, linked all those products to Amazon, created an Amazon affiliate account, which anyone can do. Like it's, it's wide open and basically just kind of, kind of went away. Like he did this as a weekend project and then he kind of got sucked back into his, his work. And you know, a few weeks later he gets a notification that he's getting a check in the mail for like

$300. Right. And he's like, okay, that's interesting. You know? And so he spends a little bit more time, like adding some more links, some more reviews, um, over the next few months. Um, but eventually just kind of walks away from it because he's got other stuff that he does. The punchline is this, this is three years ago, three years on, he's still getting a check in the mail every single month for about $700. Right. And you know, just pass it. It's something that he figured out that he did probably spent, you know, 10 or 12 hours on it. Exactly. And so if you think about it first, you think that's just sounds really weird, but then you're like, okay, well, people who have fish, they're going to search for fish tank reviews.

Not a very competitive niche, like not a ton of people competing for that. And here's the other point about that. He's not necessarily trying to create like a million dollar business. Right. I think that's a very important point. You know, that this is not, you know, this is not about IPOs. Not at all this is just about like let's supplement your income let's diversify a little bit he talks about being able to take an extra vacation every year with his wife he talks about you know just it's kind of fun money it's just exciting that it's that it's there um so to me it's the potential

it's the possibility of how this can affect your life in a positive way and i see like especially people who have always been employees and their whole income, their whole life has come from a paycheck. The first time you get that like notification, you know, from PayPal or from wherever that like money has come from this different source. It feels really, really good. Yeah. Like at the events, I often ask people like, you know, who has had that feeling and what

is it like? They just like the smile comes across their face, you know? So it's very empowering. Yeah. That's cool. So what, what do you think are the qualities of a, of a good side hustle? Like how do you distinguish a good one from maybe one you shouldn't pursue? Right. So I think, you know, maybe it's a combination of two things. Uh, something that you, you are somewhat motivated to do or interested in, or we can even say passionate about. Um, I think that's important in your side hustle. I think you should look forward to what you're doing and not just dread it. So not just anybody could do the fish tank review thing.

But then the second thing is it has to be something that is marketable that other people have, you know, the other people value. And so in this example, it's like, you know, there are people searching for that information. Not a lot of, a lot of other people were providing it. Um, and so there you go. So curiosity and observation to go back to what we, we said a few moments ago, um, probably some other people had some idea to do something like that, but they didn't, they didn't do it. This guy decided to do it. And it's ideas ultimately are easy. It's about executing that. Um, and I think, you know, beneath what you're saying is this idea that it doesn't have to be for everybody. Like you have this, you know,

section about like imagining your customer or like, you know, taking your customer out to lunch or dinner or whatever. Like who is that one person that you're catering to? You know, it's like, it's a pretty select group of people that are going to be interested in fish tanks. Right. So the point being like, it shouldn't be for everybody. I mean, maybe it can be, but I think it's, if you can target in on filling a need, where is there a void, and something that you can do that's facile, that works within the construct

of the hours that you enjoy when you're not at work, that's something to look into. And a lot of the other stories in the book go on to do much more money. Some of them do $4,000 a month or $5,000 a month and some do become six-figure incomes or beyond. And I want to show those stories too because I want people to understand what really is possible through this. But you'll never really know unless you try.

If you have some idea. It's not like every story in the book is about a blog, but just cause we were just talking about that. There's another story about this guy who starts a cruise blog, like answering questions about cruises. And that one does grow to something like $50,000 a year. Wow. Again, just, again, just through a very simple WordPress site, anybody can set this up. His skill is essentially his, he was a copywriter by day. So he used the skill that he had to kind of distill this information and put it out. So I think what people don't understand, like you said, ideas are a dime a dozen. But some people struggle with understanding what skills they have can be applied in this way.

And that's something that's really surprising. They overlook that. I'm like, that's not a marketable skill. Yeah. That's really surprised me, actually. Because I thought 80% of the people would have the second problem of like i've got the ideas i don't know what to do with them but uh this year i think just through all the interactions i've had a lot of people are more than the first group interesting yeah um so that's the first thing step one david and i were on the

blogging thing david and i were talking the other day and he told me something i didn't know which is that uh maria popova's brain picking site started as a side hustle. Like she was a copywriter at an ad agency, right. At an ad agency and was doing it as like a newsletter. Right. And then, and then people were like, so into it that it kind of blossomed from there and became her not so side hustle, but that's how it started. Right.

I don't think she probably had any intention that this was going to be the thing that was going to leave her leaving her job. And so when you don't have that intention, it's, I feel like it's a lot easier because you don't think she probably had any intention that this was going to be the thing that was going to leave her leaving her job. And so when you don't have that intention, I feel like it's a lot easier because you don't have that pressure. You don't feel like you're taking this huge risk. You're just doing something that you enjoy. But it's a unique hobby because it's a hobby that can potentially pay you money as well. But you're also not depending on it. So that's key.

when i was reading the book i'm thinking like do i need a do i need a side hustle this is my problem yeah it's my problem every day i tell these stories i'm like i want to do that too like i started like i'm like can i like mine bitcoin can i like you know i know well it's funny i got a lot of friends that are doing the bitcoin thing and like and it gets me i'm like should i be doing that but then i'm like now i'm like i have my career and then i'm like wait a minute like i just what i do is it's a collection of side hustles that kind of cohere around a central theme but it's not any one thing that i do i do i do a series of side hustles and so and i and i unlike yourself like i came from the paycheck world you know and i i made that leap and it, you know, it started with one side hustle that built into many and whatever, but, um, but you know, I know what it's like to collect that paycheck.

And I know like emotionally and mentally what that feels like and kind of what that does to you. It creates like this sort of invisible force field that makes doing something outside of that seem less accessible, just as a mental and emotional leap, I think. So this being like a welcome mat and a, and you know, and a roadmap and you know,

something that's accessible through the examples that you provide, I think is, is something that's going to really open people's, you know, minds up to the possibility like, Oh, it's just cause it's baby steps, right? It's not about like conquer the world and like, you're going to, you know minds up to the possibility like oh it's just because it's baby steps right

it's not about like conquer the world and like you're gonna you know yeah be the next you know whatever uber whatever it is exactly so no it's meant to be relatable accessible i want people to get excited about it and feel like they can do this you know they can like i really have tried to design it for people who are super busy and don't have a ton of time. But they want to also want to invest in themselves. You know, they also like, they like this idea. They're like, just show me how to do it.

And maybe they've tried before and they failed. Maybe this is also like part of the frustration. It's like they heard some of these stories like, oh, that's awesome. Like, so I try it, but it doesn't work out for me. And then, you know, it's a little bit disappointing. And so trying to get people past that basically and what do you think the biggest barrier is that people face in that like that trips them up i think they don't necessarily know what to do next i think that's a big thing um i guess i just say in general in life like knowing what to do next in whatever you're trying

to accomplish is, is a pretty powerful thing, even if it's something huge, if it's something small. And so even for something like this kind of side hustle thing, starting your business, if you've never done it before, like there's so much conflicting information out there. Maybe that's another thing is talk to people who have like, Oh, I wanted to do this. And so I took an eight week class at a community college in entrepreneurship and probably 80% of what I heard didn't really apply to me. It's not like it was wrong, you know, maybe it was right for some people, but, uh, I don't necessarily want to recruit investors and I don't necessarily want

to write an 80 page business plan. Um, how do I don't even have the information that I would need to do such a thing. Cause I don't know, you know, how people are going to respond when I do something. Right. Right. And that, and then they slink back to their job and then go down that shame spiral exactly because i'm not that kind of person and i think one of the things you talk about also is like you don't have to be some you know uh charismatic outgoing personality like you can be a bookish quiet introverted introverted person and find the side hustle that meets that you know personality niche yeah um that you can serve absolutely i mean a lot of my community identifies introverts i certainly do um you're the most extroverted

introvert that i know though no it's all it's just a skill it's not a personality but when you not at all i said this to you at wds when you're on stage you're so comfortable and so well spoken and articulate yeah well i appreciate you saying that but first of all i've had some practice like yeah over and over again and second like most introverts would probably know is like it's not so much like how you can behave in social groups it's like where do you get your energy from and so like i do an event like this like we're here tonight it's going to be a lot of people. It'll be great.

It'll be awesome. I'll be nervous before. That's fine. You just do it. Afterwards, I'm going to go back to my hotel and be by myself. People often invite me to stay. Like, oh, you want to stay on my couch? No, I can't do that.

I'm like that, though. I mean, I relate to that. I mean, a lot of the training and all that, I need that quiet time. It takes a long time for me to recharge my battery. And when I do, if I was doing an event like this, like even if it's, it's almost harder when it's less people than it is with a big event. That's true. That's true.

And it's very emotionally draining, you know, and I, and I, my like, uh, you know, rebound period is usually pretty long. Like, I don't know that I could do it every day, like on a book tour like that. Cause it, it, it emotionally takes it out and it takes a lot of energy to get up in front of people and muster that i think yeah well i think it's like a diminishing cost kind of thing to me it actually is easier in some ways to do it like night after night right because at least once i settle in yeah at least once i settle in i kind of know what to expect i know know what to do. Um, you know, I'm giving the same talk for the most part, which is actually beneficial because after a while it really is

kind of like in my head and I don't have to think about the words. I can think a lot more about connecting with the audience, which is always your goal as a speaker. But to be totally honest, if I'm speaking about something I've never spoken about before, I'm always thinking like, what's the next thing what's coming up, you know? Right. Um, so it actually becomes a lot easier for me the more often I do it. Gotcha. So I was with your friend, Gretchen Rubin, two days ago. Oh, great.

I did a podcast with her. I never met her before. I mean, I know you guys are close. Yeah. Yeah. She was fantastic. Yeah, she was great. Super cool.

And of course, we're talking about the four tendencies. Right, right. And we got along smashingly because I'm an upholder, you know? Oh, interesting. I was going to ask. Yeah. So are you, what are you? Apparently, I'm a rebel. You're a rebel Yeah, which I initially, you know argue with her about but then apparently she said every rebel argues with with her about that description And so I was like, okay, I guess so Well, I said to her I was like I bet every rebel is super glad that they're a rebel and she's like no

That's actually not true thing. Yeah Yeah, I mean I read the descriptions. I was like I want to be like more of a questioner I think but is super glad that they're a rebel. And she's like, no, that's actually not true. Yeah. Yeah. I mean, I read the descriptions. I was like, I want to be like more of a questioner, I think. But yeah, no, I think so. So why do you, what is it about you that makes you a rebel? And how does that play into how you, how you live your life and pursue your work? So, you know, according to her model, a rebel is someone who resists both inner and outer expectations. And that was my stumbling block with it for a little while, because I was like, well, outer expectations, absolutely. But, uh, you know, inner expectations, I I'm pretty disciplined. Like I have like a uphold, you know, what I believe in.

And she said, well, that's exactly it. If you believe in it, you know, you will absolutely like adhere to it. But if you don't believe in it, even if it's your inner expectation, it's going to be very difficult for you. Right. And you're not, you're not doing it because somebody told you that's what you should be doing. Right. Yeah. And it actually made a lot of sense to me because I can look and see like when I have my own struggles about things I commit to do that I struggle with, like I realized like, why did I commit to this in the first place? And I kind of can trace it back. And I'm like somewhere in this process, I committed to it because, uh, you know, I thought that I should, basically.

Or it seemed like a good idea, but I wasn't really into it. But I was like, okay, I'll try it. And that wasn't a good idea. Right. So I think the trick is, you know, to find the things that you're good at. Find those, like, that limited sphere of things that you're good at that you're also really excited about. And in terms of career stuff, hopefully that also has some impact on other people. And then just do more of that.

terms of career stuff hopefully that also has some impact on other people and then just do more of that and how do you balance the forward-facing you know chris the the wds guy and the hundred city tour guy with the you know the the more um introverted guy who likes to travel alone and write books well i'm still traveling alone i'm still spending a lot of time by myself you know and do you write do you are you writing all the time or do you pick your times? Like, okay, now I'm going into a writing phase or how does that practice look for you? Yeah, if I'm writing a book, then I have more of a writing phase, you know, and it's a few months. And I'm still doing other stuff during that time, but I'm not really doing like 100 city tours, you know, during that time. The podcast has really changed a lot of stuff for me, which is something new since we talked last.

Yeah, I want to talk about that. podcast has really changed a lot of stuff for me which is something new since yeah i want to talk about that i think when we got together the first time you were in the process of completing it or working on it and you hadn't i don't know i don't think you had announced it yet but we talked about it a little bit um it's unbelievable man you've got like over three million dollars where you're getting like millions of downloads a month something like that yeah i don't know i don't a podcast every single day that's the secret though right i'm gonna podcast every day more downloads a month right i know but still like i mean it it breaks my ass to put out one episode a week and sometimes two i can't imagine the amount of work and the structure that has to

go into putting one up every single day like first of first of all, like, how did you, how did you do this? Okay. Well, I mean, we can go back to how I, how I do it, but, uh, the format is very different, right? I mean, you have these very long form conversations. There's a lot of production that goes into it. But there's no, there's no, there's no journalistic, you know, scouring the earth to find, you know, 365 people that to talk to.

Yeah. But, you know, at this point they're kind of coming people that to talk to yeah but you know at this point they're kind of coming to to me at least a lot of them are we still have to follow up quite a bit with them but we have like an intake form where people nominate themselves to be featured so there's a process for that but to go back to like how it started you know i was thinking last summer i was like okay i think i should probably start a podcast which is funny because if you'd asked me like three years ago when when did you start your podcast? Was it three or four years ago? It was four years ago.

Yeah. If you'd asked me four years ago, almost five years ago. Yeah. I'm a terrible futurist because I would have said like, I wouldn't say it's a mistake. So you do whatever you want to do. But I would say like podcasts are kind of on the way out. You know, that's what I would have said. Yeah.

So famous last words. It was touch and go there. You know what I mean? Like they kind of came out and no one really thought it was going to be anything and it was kind of just a tepid thing for a long period of time so there was no indication that it's not like you know people knew what they were and it just wasn't growing right you know so yeah so i still thought i was like okay i'm like i'm at least five years late you know party, if not more. And so what can I do that's different? And also, to be very candid, the idea of speaking with people,

like doing these kind of interviews, really stressed me out. I don't mind being interviewed. I like this conversation. And I feel like since I have a relationship with you, I could maybe flip it. But the idea of just meeting strangers all the time, I would hate that, basically, myself. And so I was like, I need a different format. So I'm going to do no guests. It's just going to be me. Um, it's going to be short because I'm designing this program for, you know, busy people. Um, every day I'm going to tell a story, different story of somebody who,

you know, starts a side hustle without quitting their day job. How'd they do it? How'd they get the idea? What happened along the way? What challenges did they face? What was the outcome? How much money did they make, et cetera? Try to be really specific, nuts and bolts. And, um, and then the last point was, okay, I'm going to do this every single day. And here's the funny thing. The more I thought about that, I was like, Oh, that's crazy. It's like the hundred city tour, like going to every country in the world. It's very similar to that, but it, really attracted me i honestly don't think i would have been nearly as interested in this idea if i didn't do it this way it's you set yourself up for a challenge for sure i liked it yeah i know i thought about i'm like that's the way to do it and uh funny story like i do the podcast with uh with a network

they're basically like the publisher of the podcast and uh panoply yeah yeah same with gretchen same as gretchen's and uh we had like three conference calls last summer to talk about you know all kinds of stuff and at the end of the third one it was like we'd had like 45 minutes you know times three calls the guy who makes the decisions he was like it's like okay let me get this let me get this through my head because i still don't you know don't quite get it you want to do this every day, like five days a week. And I was like, five days a week. Are there only five days in your week?

You know, like, I mean, every day, seven days a week. He's like, oh, I had no idea. You know, so yeah, seven days a week, right? Seven days a week, no exceptions. And he's like, this guy has no idea, you know, like what that's going to entail. And I'm sure you didn't. No, I didn't. no i didn't i didn't yeah so how did you create a system uh-huh that allows you to do that and still go on 100 city tours and you know do all the other things that you do yeah well we're

recording this in your life we're recording this in september and so i started in january so i've had a little bit of time to kind of get more of a process. And then when you launched, how many did you have in the can? Like five. I just assumed you had like half of them done already. That's so funny. People have said that on some of my events. And like, I thought you had recorded like all 365. No, I had five. I had five done and maybe another five to ten identified that i knew what i

was going to do it just hadn't happened yeah yeah no it's very much a real-time thing it's not real time like it's not like i'm literally recording each day and it goes out that same day but it's pretty close i mean it's like a seven day i've got like a seven day you know backlog no more than that wow yeah i like that actually i think it's better because i want to have more of a backlog but i don't want to have too much because i feel like it loses like the kind of an element of the organic right i understand that yeah i've had that situation where i've done interviews and then i have a you know a glut of like backlog stuff and it takes a long time like that my most recent episode was like that and i felt really bad it just felt weird to like put something up that

had been sitting around for a long time even even though it's totally fine or whatever. It's me, but, um, wow. So there were a couple of days early on, I think it was in maybe January, February before I got better at it.

And I have a wonderful assistant named Whitney and she really helps me a ton with the process of a lot of things. Um, but I think before we kind of really found a rhythm, there were a couple of times when it was like, I'm recording the episode for tomorrow at the end of the day. And couple times when it was like i'm recording the episode for tomorrow at the end of the day and i'm you know i'm on the west coast so i'm sending it to new york uh for them to produce it over there so they're getting it like eight eight o'clock in

the evening and it goes up the next day so that kind of that was kind of stressful yeah i would imagine like you're like okay i got i'm getting on a plane if it's delayed then i'm gonna be and i've got to get there yeah that's like that's a lot of stress to carry around a lot of responsibility also technology like i'm not uh i'm not like an av guy i had to learn like how that whole stuff works all right i'm fascinated by it so like you have you must have like a obviously you have a travel kit thing that you and you're just doing this in hotel rooms and then uploading it to your producer wherever she is in new york and they just edit it and put it up and that's your relationship with it. Yep. That's great.

Right. And they do, they do a really wonderful job too. Like I have to give them credit because I don't do like the music and the next lot of stuff. For sure. Of course. So, so these things are just constantly being sourced and you're,

Oh my God. That's also another challenge. That's been another challenge too, because this is something that I would like to have a lot more stories in the queue. So if there's any listeners who have a side hustle, we'd love to be featured. On the sidehustleschool.com website, there's an intake form. On the About page, you scroll down, it's like Submit Your Story.

I'd actually love to feature folks from this community. Because in the beginning, I knew the first month or so because I know so many people. As I thought about this from like June of last year, all the way to January, I had a bunch of folks identified. But then, then after that, like if I run out of my like a list, you know, at a certain point I knew that the show had to carry itself in terms of bringing new people in. So there were some times when, you know, like to be again, very honest with you and your listeners,

I think out of 263 episodes so far, there's definitely a few of them. And I'm like, I really wish we hadn't done that one. Well, of course you can't, it's like being, you know, if you're Johnny Carson, you know, it's like not every night, you're not going to hit it out of the park every night with the guests that you want to talk to. Like, it just doesn't work that way. If you're going to do that kind of volume, you know, so.

Yeah, but I want to increase the quality. I think that's my goal is to increase the quality. And if I have more to choose from, then I can be more selective, which is what I would like to be. I go on. I want every story to be great. I want people to listen to each one. And my goal isn't for them to listen to each story and for every time to say, like, I want to do that thing.

Yeah. My goal is that they really will learn something each time or that each story will spark something in a different way. And that's what I hope. And it's also like a daily reminder that it's doable. You know, it's empowering to hear these stories. And if you just, you know, even if you're you have to listen to doable you know it's empowering to hear these stories and if you just you know even if you're you have to listen to you know 10 in a row or whatever over the

course of a couple weeks like you it just kind of percolates in in the consciousness and then eventually you you because it's a lot of these things are timing you know it's like people just they're interested in it but like the stars aren't aligned for them to actually make that decision and that's a very individuated kind of thing right i agree and but the more listen the more the more yeah everybody who's listening like send it in like because if you get tons of stuff then i can help reduce your stress a little that's nice and then also we could feature some great stories yeah of course man actually makes me happy because now that the podcast has had some traction it's really good for the people who are featured on the show at least sometimes like i never want to promise like oh you're going to get a bunch of you know new

customers or whatever but there have been some good stories of you know people that have been helped through it well and you know my podcast started as it definitely was a side hustle i did it for a long time before it generated any revenue i just did it because i loved it i would have done it anyway and maybe i'd still be doing it if it wasn't you know making any money it's become more of a professional thing but it certainly didn't start like that it started because it sounded cool and i was a fan of the medium you know and i felt like i could you know have a voice in it and now five years later and then you know still doing it like but i would have never foreseen that it would be you know take up the amount of time that it would be

kind of like the tip of the spear of all the other things that i did right but you've also raised the bars you've gone along and you learn and you know of course you know i look back and i can't i never listened to anything that i've done i would never read my early blog i would never go back same thing yeah read your first blog post right the same but it's a good lesson for listeners perhaps because when they look at successful people and they're trying to do something similar like start the podcast or write the book or whatever, I always tell them, like, don't do it with me because my early stuff is terrible, but like go back to somebody you admire

and like actually like see where they started. Listen to that first podcast episode and read those first few entries on the blog and it's probably not going to be that great. And that's good because it's relatable. Or at least you can see if maybe it's great, but you can see how they evolved. You can see like the path that they went on.

And there's definitely going to be a trajectory there. And think that that's helpful yeah i think that's absolutely true it would be interesting to talk a little bit about um you know because it's in the context of of the side hustle uh the evolution of the digital space. You know, you're somebody who began, I mean, you kind of began as a travel blogger. You know, it was the early days of blogging. And then there was that moment in time where there were blogger superstars. And, you know, you had your Seth Godin's and all these people that were getting massive, you know, readerships. And that kind of, you know know elevated these people into becoming cultural influencers

and then you know these things are always changing right social media kind of shifts that when i look at the blogosphere now it's it's very different right i can't imagine there's any big bloggers that have the same level of readership that they had during that period of time because the way that we consume content is different it's not really about driving people to your website anymore it's about going where people are exactly and you know in many ways podcasting has supplanted you know part of that blogosphere and now you see all these people vlogging and like you know who knows what's going to come next with this and and the way the habits with which we um you know consume this content are are changing and at the same time there's so much of it that we by our very nature have to be more discerning about okay what did what we we have a limited

amount of time what are we going to consume and as somebody who is a you know an author in a very traditional you know way with publishing books but but also somebody who has all these side hustles and is a podcaster and a blogger and all of that. How do you look at that and how do you forward cast and think about, are you paying attention to what other people, are you looking for, how do we respond to the marketplace in that way? Because I'm always trying to,

just, it doesn't necessarily modify my behavior, but i'm just interested in kind of paying attention to how these things continue to change and evolve yeah i don't know if i do forward cast very well because like i said you know i started my podcast you know what six months ago but i would say yeah but you you think of that as being late to the party but i look at that and going you've made the choice at the right time you know what i mean it would been, you could have started a long time ago. Yeah, you would have been an early, more of an early adopter, but the audience wouldn't have been there. I mean, when I started my blog, what, eight years ago or something now,

I thought I was late then because I looked around and there was lots of other, and Gretchen's actually one of them. Gretchen had been doing this thing for a while. I'm like, wow, you know, like should have done this two years ago. So I guess the, you know, the right time to start is now is always the classic lesson. But as for, you know, the content saturation, I think content saturation is probably the biggest problem. Yeah.

It's not just the shifting medium, the shifting medium, like there's always going to be new mediums, as you said. But the problem is the old mediums don't completely go away. So yes, blogs have diminished in influence, but they're still out there. And, you know, now you have so many different social networks and platforms and ways for people to get all kinds of things. So you're not just competing against other blogs or other podcasts or whatever it's, it's Netflix and everything else that's out there. Right. Right. That's what's, that's, what's hard, I think. Right. And so you

don't, you don't really think about how that impacts what you do. You just, you just stay steady on like whatever you're for better or worse, yeah for better or worse no it's good to hear i know what i know i do too you know but you know what i mean and like i'm like there's other people that are smarter than me no doubt and they're like you know figured out the next big thing but this is that's kind of like where we started about like why are you doing these hundred city tours i'm like it's because it's what i got it's what i know how to do yeah you know but it's fun for It is. You would choose to do that anyway, I would imagine. I would, yeah. This is your wanderlust.

Yeah. As long as people, as long as it makes sense. It has to make some degree of sense, not just commercially, but in terms of impact. And like if nobody came out to the events, I think that would be kind of depressing. Right. So, yeah. So, I do want people to come out. I've had events like that.

I've had some before the past for sure of course that's how you get started you know right of course that that first tour i mean the first tour was really interesting because back to back you know when you do all 50 states you don't really go in like ascending order you know from like smallest to biggest or you go in like a geographical order and so i would like have these back-to-back events where you know it would be like los angeles you know and like i don't know 100 200 people or something would be there and i'm like wow i'm a superstar and then the next day i'd go to reno you know there'd be like 12 people there and i'm like okay you know yeah i'm sitting there like five minutes you know before

the start time and i'm like looking at you know looking at the chairs what am i doing yeah i'm like it actually cost me a lot of money to get here. I know, yeah, exactly. Right, so it was a good little lesson in humility. Yeah, yeah. I like that you're still doing it, that you didn't decide that you had graduated from that. I think there's a humility in that.

Yeah, I think it's important for me. That's all I know. It's like, for me, it's what I should be doing. And I do look forward to it. And i get frustrated when i don't do it like as well as i want to or whatever but i do think it's it's something that's going to stick with me and when you develop these new like with each book you have to develop a new presentation a new talk like what is your process for doing that do you look in the mirror and rehearse it like i do i mean I rehearse quite a bit yeah I mean it's not like improvised you know it's always funny sometimes people come up at like the 40 second stop of the tour and they're like do you write that talk just for tonight yeah

I'm like yeah I write an original one every night you know every single night I'm like you know three hours you know what am I with my speech writer that travels with me exactly um but what's the process well most of them come out of the book right so I feel like I have this natural extension like what is the message of the book? What am I trying to share with the book? And I write prescriptive nonfiction in the sense that I'm not just trying to document something. I am putting forward an agenda. Like, I definitely want to challenge people's thoughts and, like, provide them some kind of, you know, something to go away with.

Like, I want them to take action. I don't necessarily need to agree with me all the time, but i want them to know like here's my manifesto so if i start with a manifesto then it's like how do i translate that you know to about a 25 minute talk basically and so i'm not even sure that you articulated the manifesto of this book the manifesto of this book is that you need a side hustle. You need more than one source of income, even if you love your job. And it's not that hard to do it. There's a process. And if you've tried to do it before and you failed, like, well, I failed at lots of things, but you should try again. And you don't have to spend a lot of money doing it either. You don't have to spend a lot of money. You don't have to go out and acquire a ton of new skills. If you're not an app developer,

don't try to develop an app. Let's figure're what you're good at and find a way to translate that into something i know that you started dozens of these side hustles what are some of the some of the ones that worked and some of the ones that didn't yeah my whole life like you said uh has been side hustles and um i mean i started you know 20 years ago ago now, I'm almost 40 and started with like importing coffee from Jamaica and resold it on eBay, you know, to the US. And I learned how to do that because I saw these people selling coffee for like $18 a pound or whatever. I'm like, where do they get that from? And I tracked down the distributor. I'm like, they get it for like $11.

If I buy this and sell, you know, and once I started doing that, it was just I love the creativity of it. Like I was really attracted to that, um, that kind of thinking and process. So let's see over, over the course of a long time. Um, I mean, these days, pretty much everything is kind of associated with my career one way or another, but I, I once, uh, I once tried to have this golf membership business and I hate golf, which is a good first kind of you know sign that it wasn't the smartest i don't say i hate it i just don't like it i just don't care i have no opinion on golf and unlike malcolm gladwell yeah listen to his no i don't know he did in revisions history he did a whole thing about how much he hates golf oh okay yeah no i'm just neutral on golf but anyway

i had this idea and uh i forget exactly how it went but it involved it was basically like selling this golf membership for, for a dollar. And there wasn't really any backend to it. There wasn't really an upsell to it. And I remember sitting with the web designer at the time, this is like 15 years ago and sitting with the guy who was building the website. And he was like, Chris, how are you going to make money on like a dollar a customer? And I was like, just build a website.

You know, what do you, what do you know? I mean, I don't say it like that, but I'm just, you know, I don't, I got a plan, you know, I didn't really have a plan. So it didn't really go that well. But you, but hold on a second. Like, I don't even understand how that works from a foundational point of view. The idea was, I think there's a little bit more. So there was like, I mean, this is going way back. I haven't thought about this much, but there was like a catalog of courses where you got like two for one green fees or something. And so, uh uh my business model was like the selling the membership for a dollar and then i think to redeem it you had to pay 14 or something so i guess there was a little bit of back end but it

was still very very little compared to the cost of you know acquiring a customer or whatever so it's just some idea that i thought was a good idea at the time didn't work out right you know then i mean it's not that exciting of a story but that's most of the stories that didn't work out are not that exciting right and do you think of like do you think of what you do now as a collection of side hustles also like do you or do you just are you you consider yourself like a writer who does other things or an author yeah i mean i guess these days it's kind of an integrated cohesive thing like you said about your stuff like i do see myself first and foremost as a writer i don't write books as a as like a funnel for something else right you know i don't it's not like a you know this is my secret to get people into my world and then i'm going to sell you a

thousand dollar program or something like it's done some infusion soft no exactly that you can't escape from yeah i mean some people i mean yeah if it works for people that's fine but it's not that's not me so you know i first and foremost an author and, uh, and I'm actually trying to start fewer side hustles these days just because I don't feel like I always do a good job with what's in front of me. And I'm trying to like, not really stay in my lane because that sounds restrictive, but like a more positive way of thinking of it is like, what is the work that has been given to me?

You know, like by the universe, by God, by me seeking it out, whatever you think of it as like, what, what is in front of has been given to me? By the universe, by God, by me seeking it out, whatever you think of it as, what is in front of me that I can do? I do have this influence. It is kind of rare. How can I use that well? And so for me, it's probably not the smartest thing to mine Bitcoin or to write the blog about fish tanks

or whatever. But like I said, when I work on this stuff, there are lots of times I'm like, I really wish I could do that. I wish I could have like 20 extra hours, you know, even 10 extra hours a week to just, cause I love the creative process of that kind of thing.

But I don't, I don't have that time right now. Do you think you're going to continue the podcast for another year? Or is it, this is going to be a one year thing. Are you going to keep going? What do you think I should do? Are you enjoying yourself?

Yeah. Then you should keep going. Great. You know, I will. All right, good. I'm glad you made that decision right now. are you enjoying yourself yeah then you should keep going great you know i will all right good i'm glad you made that decision right now thanks rich yeah well i think you've set it up in a way i mean the longer you do it the easier it gets it becomes more like rote for you i think and and then the challenge becomes maintaining your enthusiasm for it because then it just

becomes like oh i gotta do this thing you know blah blah oh here's the submission I'll just like write this thing up and say it you know and be done with right so I think you do it as long as you can you're you're sure that you're doing it for the right reasons and not just because you've made this commitment totally great yeah I think the right time to leave you know like I feel like I have the best job in the world in lots of different ways and the right time to leave the best job in the world and whatever you whatever outlet it is, is like right before you get tired of it. You know what I mean? Yeah.

And I think that's the role I've set up for myself. Like I still love it and I look forward to the, you know, and I get, I get nervous before, you know, it's like it takes, it's, this is actually the second podcast that I've done today. Okay. And that never happened. Like I never do more than one in a day because it does take a lot of energy just because you were only here for a day i was like thank you for making time for me i appreciate it thank you no no i mean i didn't there was no way this wasn't

going to happen oh it's awesome um but as long as it as long as i can approach these conversations with that enthusiasm i'm not looking forward to it then you know i'll keep doing it but the minute i start to dread it or anything like that like it's time to do something else great totally right um all right cool we have like the the event's gonna start pretty soon right yeah so let's let's talk a little let's leave some people with some actionable sort of steps that they can take um i think they're you know there's a lot of people that listen to this podcast who are in jobs and many of them like their jobs and many of them are dissatisfied in, in cubicles that they wish they could figure out some way to reach escape velocity. But in the meantime, you know, how can they, how can they get off the dime and start thinking about like how they can bring the side hustle into their experience?

Great. So we spent a lot of time talking about ideas. Let's maybe go to the next stage and say, okay, you've got an idea. What's like a practical thing that you can do? Most people, when they do this for the first time, their idea is not that specific or their idea is certainly not an offer. And so I encourage people to take their idea and translate it or transform it into an offer as quickly as possible. So an offer has a promise, which is like the benefits, like how are you going to change the world or at least change this one person's life with what you're offering? And then a pitch basically like, how are you, you know, what is it? Is it copy that you're writing? Is it some like way for them to sign up and then a price?

So people don't buy ideas, they buy offers. So the kind of the takeaway is like, once you have your little business idea, whatever it is, um, what exactly are you going to offer people? Like, how are they going to sign up? What are they going to pay for it? Making those kinds of decisions. And there's a process to do that in the book, but even without the book, you can just start thinking that way. And I feel that that's, that's helpful because it's more concrete. Mm-hmm. And then you have this, uh, this thing about, um, you know, testing it out, like proofing it or whatever, like working out the kinks and you have the thing

about like, you know, ask 10 people for advice or, you know, you know, broaden your horizon. Don't try to just do this, you know, in isolation. And then this idea of like, look, you have to be on some level, you gotta be a marketer and an advertiser. Right. And you have this idea of like, look, you have to be on some level, you got to be a marketer and an advertiser. Right. And you have this idea of like, you know, channeling your inner Girl Scout. Right. So like a Girl Scout. Tell me what you mean by that. So like a Girl Scout. I was thinking about this because, you know, I live in Portland, Oregon, and it's probably the same in lots of other cities, too. But, you know, in Portland, I walked on the street and they have these street canvassers that are always like pitching for various causes. And they're, they're pitching for causes that are

often good causes that, you know, I might believe in, but it also does feel kind of annoying. You know, it feels like you feel like you feel like you're accosted and they have all these psychological tricks to get you to talk to them. Right. And that's like the salesmanship. And meanwhile, you can go, you know, in the spring out in front of the drugstore or anywhere else. And the Girl Scouts are out there selling cookies and everybody's buying them, right? Like people are lined up to buy them. And the pitch is really simple. Like, you want to buy my Girl Scout cookies?

Okay. You know, here's $5 a box. Here's 20 bucks, you know, right? So what are the Girl Scouts doing differently, you know, from the street canvassers, essentially? Like they figured out the right products, like they've been in the right place. You know, they're finding people that are already interested in it rather than kind of trying to, you know, nail people down. So there's something about that in there.

Or make you feel bad about yourself. Yeah, exactly. Guilt. It's marketing by guilt. And so when you said like, you have to be a marketer, I think that's true, but I think people sometimes shy away from it because they think, oh, I'm going to be like that street canvasser. Yeah.

When really just marketing is, uh, marketing is connecting with people, right? It's connecting with the right kind of people. That's why you can be an introvert and have a side hustle because you're not like the street canvassers you know you're like the you're like the girl scouts people want to come to you right i think also uh you know we live in a time where where these tools are available i mean when i when i was a kid like you couldn't like if you want to start a business it was like what are you going to go to the small better business small business association it's like yeah you know now you can get squarespace or you know these tools that you don't really need to know that i mean you got to like have enough of a you know desire to research

these things and learn a little bit but like that's knowledge that anyone can acquire yeah like anything exactly knowledge and there's a YouTube video for any question that I would want answered about whatever it is that you're facing I have a lot of stories about people who have started their side hustle but learning how to do something by watching YouTube like there's one I'll tell tonight it's actually I don't know if it's in the book or not I forget but guy who makes candles and he's actually doing like $2,000 a month on Amazon like completely passively we has to make the candles but then the sales are passive right and he's actually doing like two thousand dollars a month on amazon like completely passively uh well he has to make the candles but then the sales are passive right and he learned

how to make candles by googling how to make candles on youtube right right well i started this podcast by googling how do you start a podcast because i was like i don't know like how do you okay so like i understand you have to record your voice right then like how does that end up on itunes you know it's magic isn't it right so i googled it and then pat flynn had this series of videos like literally he had i think five or six videos that took you from beginning to end like here's the mic you get here's the wire you need and here's the thing you here's how you work it and here's here's the you know step by step how you get it and i was like and i just followed that exactly the way he said it like had that had that tool not existed there maybe I would have just felt like the

barrier was too impenetrable and just never have done it. Right. You know? So information is accessible. The tools are much easier than they've ever been. More people are online now than ever. So you have more access to customers and more people are used to buying things online also. Right.

That's true. There's less, less skepticism than there used to be. Like my grandma has a PayPal account now. And I was like, okay, I know that this has officially kind of jumped the shark if my grandma is buying things on PayPal. What's your favorite story of all the submissions that you've gotten or the people that you've spoken to? Oh, I don't know.

I don't know if I have a single favorite story. Well, give me one. I know I should get better at that question, right? Well, we were just talking about YouTube. So here's another one. There's a, there's a woman who is, is helping people pass citizenship courses, um, by providing this teaching through YouTube tutorials. So she's actually producing this content. She's doing like voiceover and like, you know, teaching people like, here's how to prepare for the citizenship test. Here's what you need to know. And there's all these different sections. So she's built like voiceover and like you know teaching people like here's how to prepare for the citizenship test here's what you need to know there's all these different sections so she's built

this whole like youtube channel for it um and she's actually doing really well it's like three thousand dollars a month or something with it the thing i like about it is it's a social good she's basically like helping people like in some cases who might be disadvantaged or not have access to go to private tutoring or whatever and uh the way the money works is it's like a youtube advertising model right it's sponsorship a YouTube advertising model, right? It's sponsorship. So the people who benefit from it aren't actually paying for it.

So they get access to this information for free. They get prepared. She's got all these great testimonials of people who have passed the citizenship test and become US citizens from her work, but they've paid nothing for it because of how this world works. So I like that one.

Yeah, that's pretty cool. There's others too, but that's good. Yeah, yeah, yeah yeah give me one more and then we'll wrap it up okay there's another woman who um and we're all the same kind of thread line here but just a little bit different uh woman uh who's a little bit older actually and um she does these online courses about baking bread and so two years ago she created a course about sourdough bread she was really into baking bread that was her thing and she didn't know anything about how to use like technology and she figured it out essentially and uh she also didn't have a lot of money before and so this course two years ago uh made twenty five thousand dollars and then last year she like you know kind of really

delved into it further and made like five more courses all still about bread and most of the mostly about sourdough bread in fact like that's her niche like she's really into like the sourdough bread thing so you have like that's a whole thing extreme sourdough and advanced sourdough and uh so she made 85 000 last year wow from it and like i said she was a bit older and had never had money and um she actually had some trauma in her life and was on food stamps for a while like true story and uh she was now able to pay put a down payment on her first home you know in her mid-60s or whatever from that wow that's a beautiful story and as somebody who who you know your life is invested in learning about you know business and entrepreneurship and self-actualization this is what you spend most of your time thinking about and writing about.

And then you encounter these people who have these amazing stories. Like, what have you learned from them? Or how have you changed how you look at this as a result of those experiences? Yeah, I think for me, I guess maybe for a time, I kind of made light of some of these things,

not consciously, but I think I was trying to, that's cute. Yeah, exactly. Like maybe like, I want to be like more of a philosopher, like a thought leader or something, you know what I mean? Like, but actually like there's a lot of beauty in this and this actually is really affecting people's lives in a very positive way. And I actually want to do more things like this. Right. And so I kind of go away. I also feel challenged personally, because I think back about all the different projects I've started and started. And it's fun to kind of be on the weeds of that, uh, at least through other people's stories in a way that I haven't been for a long

time myself. Right. So, so is this, uh, helping you think about what you're going to be writing next? We'll see. I kind of want to stay on this, this topic, uh, helping you think about what you're going to be writing next? We'll see. I kind of want to stay on this, this topic, uh, like broadly speaking for, for a while. I'm actually really enjoying this, especially if I do the podcast another year, you know, I'm going to have to do an extension of this. So I've got a hundred cities. I'm here in number two. So I have a little bit of time before I, you know, do something totally different.

Right. I mean, have you thought about doing a bricks and mortar version of the Side Hustle School where there's actually sort of an institutional version of that where people can come and learn in person? I did Side Hustle School workshops. I did about eight of them this year. It's kind of like a little test model to see,

do I want to continue this way or do something different? If I did it, it would be like a traveling model. Of course, it wouldn't just be in one place. And that's what I was doing, but now I'm kind of like shifting to the tour, which are mostly free events. So I have to figure out where to go from, from there. I mean, you could do an online course as well, right? Yeah. And I think I, and I think that's good. I think it's good. I think there's definitely people have expressed to me like over and over, they want to connect with more people who are doing this and one of the things they need is support and i don't always build good systems in the sense that people are emailing me all the time which is fine like i'm honored to hear from

my readers and listeners but then it's really hard for me to like provide you know personalized coaching or consulting and your responses to everybody and so i feel like i need to if i'm if i'm truly, if I'm truly going to, if I'm truly going to help like a population, so to speak, then I should spend some time creating a foundation or a structure that would then serve them better. So yeah, that, that can scale appropriately. We'll see. Chris Killivere is good talking to you. Thank you, sir. Yeah. Awesome. So the new book is side hustle.

You can find it wherever you uh enjoy your literature please patronize independent bookstores when you can um chris gillibow is easy to find on the internet uh at chris gill i know i like how you're started to do instagram stories i'm trying i'm learning from you that's good i've learned so much from you i chuckled the first time you're like okay so i'm gonna be doing because i'm doing this thing i was laughing i was like i was like i'm gonna be embarrassed no it's fantastic i've learned so much from you yeah uh so if you want to check out chris he's probably coming to a city near you that's right if you live in a city right so where do they find the uh the schedule

for where you're going to be yeah it's actually going to be worldwide it's uh the first you know 40 cities are u.s and canada but then it's going to go worldwide side hustle school.com slash tour nice there you go man anything else you want to say no it's a big honor thank you for the conversation and thank you for listening yeah thank you thank you for having it with me chris all right man let's let's go have fun with these people out here right rock and roll sounds good all. All right. Peace. Thanks. All right. We did it. What do you guys think? Did you enjoy that? Did you figure out what your side hustle is yet? Do you know how to move forward and start bringing in some passive income

into your life? No? That's okay. Check out Chris's latest book, Side Hustle, From Idea to Income in 27 Days. You can also find him online, chrisgillibeau.com. And on Instagram, he's at 193countries. So give him a shout out, let him know what you thought about the conversation. Tell him how much you enjoyed listening to him. And be sure to check out the video that David and I made behind the scenes of this episode.

Again, it's called It Always Gets Done. It's on YouTube. My channel is youtube.com forward slash richroll. If you enjoy it, if you enjoy my other videos, please hit subscribe. I'm also, and again, I'm telling you this again, I have embedded it on the episode page for this episode at richroll.com where you will also find copious show notes for this episode. Jason and I put in a lot of time into crafting and creating basically a bibliography that goes with every

episode of the podcast. Lots of things, tons of information, links to everything relevant and pertinent to the conversation to help take your edification and infotainment beyond that ear hole. Also, check out Chris's podcast at SideHustleSchool.com. It's called Side Hustle. You can find it on iTunes as well. How's the eating going? How's the nutrition going?

Look, my mission in life is to help you guys experience your version of what I have experienced, eating and living the way that I do. And everything that I do, books, podcasts, public speaking, my athletic endeavors, they're all designed to advance this purpose. And I know that you guys get it intellectually. And yet every day I get emails and messages from people telling me that they're still struggling with how to implement a plant-based diet, a plant-centric lifestyle. How do I eat more plants?

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