Adaptation, Self-Awareness and Art of the Side Hustle with Chris Guillebeau

Adaptation, Self-Awareness and Art of the Side Hustle with Chris Guillebeau

– Hey everybody what’s up? It’s Chase. Welcome to another episode of the show. That’s right the Chase Jarvis Live Show, here on Creative Live. You know the show. This is where I sit down
with the most amazing humans, and I do everything I can
to unpack their brains with the goal of helping
you live your dreams, and career, and hobby and in life. My guest today is one
of my favorite people. He’s a New York Times best-selling
author of lots of books, including “The $100 Startup,” “The Art of Non-Conformity,”
several other things. And he’s also the founder
of one of my favorite conferences in the world,
The World Domination Summit in, World Dom Summit? – Yeah.
– Yeah, World Domination Summit in Portland. – Tea parties, and conference.
– Tea party. (laughs) – My guest is the one and only, imitable Mr. Chris
Guillebeau in the house. – Chase Jarvis, thank you. (upbeat building guitar
and percussion music) (audience applauds) – We love you. – Hey man, great to be back. – Yes, new book! We got to talk about a lot of things, but I just, it was sitting
here, I couldn’t help it. This is gorgeous, I don’t know. Pa-pow! – So heavy, it’s just a like weapon also. – Yeah! This is… (makes crashing noise) Big time, fancy package, man. Congratulations.
– Thanks you. – We’ll get to that in a second. Welcome to Seattle. – Thank you, glad to be back, always. – Book talk tonight. – Yup. – How’s it going? – It’s going great! – Yeah?
– Yeah. Things are new, this book just came out. I actually haven’t been
traveling a whole lot, so it’s good to actually
get back on the road and talk with folks. – Well, for you, when you
haven’t been traveling, how many miles you gonna have now, only 200,000?
– Not that much, no, actually. – I’m going to like loosen
all my status and everything. – What?!
– I know it’s crazy. I turned 40 last year,
I’m like re-evaluate, I’m like it’s ridiculous. – You’re the icon of airline status. – I’m gonna pass that mentor onto somebody I guess. I’m still traveling some. I mean I went to Thailand
a couple months ago, got some other stuff up, but it’s not really has much as I used to. – Is that ’cause you’ve
focused on your book? – Focus on the book. Just kind of focus on my
life and it’s just like, what do I want? So some of it’s work, like
I do this daily podcast seven days a week. Mostly it’s just like what
brings me the most enjoyment, the most fulfillment, how do I want to spend my time? And so just found that I wasn’t enjoying as much travel, as much as I was, but it’s not like I’m
writing it off, or anything. – Yeah.
– I think there are seasons also, there are seasons where it’s like, – For sure.
– this is what you do for awhile, you create, you
rejuvenate or something. And then you’re like, I
want to go see the world. It all comes back around. – It does. Speaking of coming back around
I want to go back around to the first World Domination
Summit that I attended. – You spoke about that first
when you came to, right? 20 something, I don’t know– – 2012, 2013? I don’t know, ’13, ’14, ’13?
– Yeah I don’t know. 30 years ago or something. – (laughs) That’s where these dark circles under my eyes are from. Because I’m 100 years old now. I was so moved by the… I’ll call it audience, or tribe, or community that you’ve assembled. Truly global, people coming from all, this is what I love about
physical face to face stuff. It’s one of my favorite
things about Creative Live, that we’ve got thousands of classes. But all those classes were
made by people coming in from all over the world, sit in one room to make class. It’s not like just on a webcam, you know? You’ve done that, it’s almost the reverse. You bring thousands of
people together in one event. We bring tens of people,
or 50 people together for thousands of events. I was shocked at how diverse, and open, and inclusive, and
interesting and passionate. How have you built that around your work? – They bring so much to it,
I think that’s a key point. They really are super passionate. I mean you probably saw, as speaker, it’s one of the easiest
audiences to speak to. You can walk out and be like, “Hi.” And everybody’s like standing ovation. – Yes! – Okay, wow, okay great!
– Yeah. (laughs) – So I don’t know how
much of that comes from the top down as it is, it’s just I guess from the beginning of my work, really interesting people
who are kind of drawn to it. And I notice that. And so I kind of, I was like wow. I think that’s where a lot
of people that were drawn to it, kind of felt
like they didn’t fit in – Yeah, yeah.
– in some way. In the beginning I thought
I was just like writing about traveling the
world, or whatever, and realized pretty quickly
that some people were making more of an emotional connection to it. And so I just wanted to be
sensitive to that in turn, and provide a space for that. I think if you do that, then they come and bring so
much to it, as well. So I can’t take too much credit for it. – Well, that sounds exactly like you to not take too much credit for it, but you’re at the center
(laughs) of that community, you built it from the ground up. It’s made up of lots of different people. – Sure.
– But, part of what… I believe that, you know
the people grew up listening and watching right now. Largely there are two groups
trying to go from zero to one, start something and go from one to 10, get better at it, find
another, their next chapter. And what I’ve learned,
and what I’m enjoying, sort of a rediscovery, ’cause this was, it was known, but I wasn’t
acknowledging it that you choose the people
that you hang around with. And when you find the
thing that you want to do, if you’re at home in your
underwear and, ah-ha right now, and you’re saying, “Gosh
I really want to be, “get awesome at calligraphy, or whatever.” And none of that happens alone. You have to build a little
community around it. And that community over
time, there’s this, or I’ve always believed, but haven’t really
articulated until recently, you have to invest. So, clearly you’ve
invested in your community. But for someone who’s sitting at home, you launched an online business, or, yeah an online business I would say, 10 years ago or whatever. There’s someone at home in Ohio, or Oklahoma, or Oslo saying,
“Great, I want to do that. “But where do I find my people? “Where do I find my tribe?” Where did you find yours, and how did you start to create it? – Well you start with
the people that you know. And everybody knows somebody, right? The old joke about my blog
was like I started my blog, and five people are subscribed to it, and one of them is my grandma. And I’m like, okay cool, my
grandma’s reading my blog. I realized she had two email addresses and she had signed up twice. – (laughs)
– She’s actually 40% of the readership, you know? So everybody knows somebody. When you’re talking about
building this community. I was just thinking, well you know what? Last night I was in Denver, and I was talking to 100 people. And 100 people is not a
small group by any means. But still it was very much
like when I got started with the blog. for me I had this travel thing going, so I went to a lot of places. Not everybody can do
that who wants to do it. With the first book I had
I went to all 50 states. And meet readers, I was
like, “Whoever’s out there, “come show up.” And it was really just a beautiful thing, because sometimes 10 people would show up. And that was okay. So if you’re out there in
Ohio or Oslo, or whatever. First of all what is it that
you’re trying to create? What is that calligraphy
thing, what is your message? What do you want to show the world? I don’t think you need
to worry so much about how do I scale this message? You don’t have to worry
so much about that. How to go from the one
to the 10, or whatever, if you’re in that early position. It’s first of all just
be true to your message. And then once you have
one person out there that actually cares about it, then that person is
like, you’re a hero then. It’s kind of interesting,
’cause they’re looking up to you, but you’re
gonna drive a lot of energy and value from them, as well. And then from one person to five, to 10, to however many. So the numbers aren’t so important. I think it’s possible
to treat your customers, fans, readers, followers, et cetera, just like the most amazing
people in the world, because they really are to you. And I think if you had that
attitude and that spirit, and you try to carry that over
throughout all that you do, then you’re probably gonna go far. But if you don’t like far,
you’re going to be able to build a good little business. You’re going to be able to
work that you believe in. And you’ll be able to open your
doors and the opportunities. ‘Cause I had no idea when I
started what was gonna happen. You know I didn’t have a strategic plan. – Yeah. – It was just I’m doing
things I’m excited about. – You said something earlier about, about how you spend your time. Is that your primary lens
through which you looked at what you wanted to do? Or was like the other way around? I know I want to be a travel hack writer, however you described
yourself in the early days, and non-conformist. – Yeah, there’s very
broad labeling by design. – Yeah, of course.
– ‘Cause I didn’t want to get pigeon-holed to it. – But, like, I don’t know. – I think I was also
interested in outcomes, and I was interested in like, I want to quote unquote build
some kind of community. I want to write a book, want
to have an online business. But again, it was really
vague in the beginning. In the beginning it was, I
don’t know if it was so much like deliverable based, or time-based, as it was feeling based. It was like I have a sense that I’m, I don’t want to get esoteric,
or overly spiritual, but a sense that there’s something out there that I have to discover. And I think a lot of people feel this way from a variety of backgrounds. There’s something out there
that’s either my calling, or my mission, or maybe
again I’ll think of it in a different way, but there’s
something out there for me. So I felt that and I was
interested on going on this path of discovery, to figure out what it was. And the only way that
you do that I think is when you see that next step,
you take that next step. You don’t actually know all the steps. – Right, you don’t have
to see the whole face, the whole staircase.
– You won’t actually, you won’t be able to. In fact I think, if you
think you can see the whole flight of staircase, or whatever it is, that you’re vision’s kind
of limited, actually. Because once you start taking these steps you’re like, wow, actually the vision is bigger than I thought. Didn’t know I was gonna
do that convference with thousands of people
coming, had no idea. I didn’t, I wanted to write one book. Now this is the sixth book,
and I love writing books, I love everything about it. All the other stuff that came it was like I just had the one step
and so I took that step. – Can we go into your
creative process a little bit? – Sure.
– ‘Cause I’m gonna ask you to think about it in
three different buckets. There’s the bucket of writing books, there’s the bucket of
creating all of the amazing online classes that you’ve created. Creative Live not aside. And then the event you’ve created the World Domination Summit which is just bonkers, you have thousand so
people coming to take over. Portland’s not a big place. – (laughs)
– So you put like 3,500 people. And I think you’ve decided
to scale it down now. When it was at 3,000 or
4,000 people, you’re like there’s not a person
important who doesn’t have the WDC… (stumbles)
– Right, right, right. – You’re like, “Hey, hey, hey.” You don’t go anywhere without seeing him. But each of those things, what are some of the creative process. Because I think, again I’m
trying to make this relevant for as many people.
– Yeah, of course. – And those are really big markers for creators and entrepreneurs. And you could see whether
it’s an online business, or a business in real
life, it doesn’t matter. What’s your creative process
for each of those process? – I actually think all three
of them start from the same desire, or again feeling or intent. If I look ahead I want to see
this book out in the world. I want to have this online course done. I have this, again,
vague internalized idea of having people together in a room, and talking about all
these different values, and explorations and so on. So it really starts with that. – The feeling that you are- – Yeah, very much, the feeling. What do I want to have for that? ‘Cause I’m actually a
pretty practical person. I know we’re talking big picture, but I’m actual really practical. Here’s my list of steps,
here’s what I’m gonna do today, because if I do these five things I’m getting closer to that product, or whatever at the end. But, I think it’s actually
sometimes a mistake to start with that, because you then spend
all your time making the wrong thing, basically. And I don’t want to put that on people, because if you’re not what
to make, just make something. But at the same time if
you’re trying to really pursue some kind of legacy work,
or do something you want to be proud of at the day. For me and you, and lots
of people out there, there’s lots of projects
that we could work on. So on the front end, what
is it that I want to create? And then from there it’s like, to bring people together for an event, the most important thing you have to have is interest in that event. You can figure out everything,
like the first year at WDS, we had no idea what
we were doing about anything, in terms of event planning, and AV stuff, and like
signing contracts with venues. I mean I’d go to have these meetings, and they would ask all these
questions, I have no idea. I’m sure they thought I was (laughs) ridiculously stupid, which I was. But the point we went away,
and then we fill that building. We filled that building,
the art museum in Portland the first year, the Newmark
Theater the second year. So if you have the demand in that way, you can figure everything
else out I think. And so the same is true for a book. If you have something you
really believe in, a message, then everything else is
just reverse engineering. Everything else is,
okay what’s the best way I put that out in the world. Do I need a publisher,
should I do it myself, what is the best format? How do I present this message,
what is the outline of it? And when it comes to the writing… Okay, so the book is gonna be x thousand words, approximately. What’s a reasonable figure
that I can write every day. Then of course there’s an editing process and all that kind of stuff. I feel like these are
just details, you know? – Yeah.
– These are just details. – And you discover, is your
premise that you discover those details when you get there? – Yeah.
– Is it like the, the next step in the process? – And the more you do
this stuff then the more you feel more confident in it. Experience kind of
produces this confidence, and you’re like, okay I did this before, so I know I can do it again. And hopefully I’m not just
doing the same thing over again, hopefully I’m like next leveling it. I think if there’s no
challenge then it’s also a time to be like, whoa, if I’m
just doing the same thing, and I’m not afraid of anything, if I don’t feel any nervousness, then I need to re-evaluate. Because I think that’s
actually the creative process. – That’s part of what made
me sort of try something besides just the commercial photography that I had done for a decade. Because like, when you like… I know exactly what to
say to the art director. She’s gonna walk over here,
and then I’m gonna say this, and she can go, “Oh my
god, that’s awesome.” Like when you can see everything – Yeah, sure.
– before it happens. And when it was still living a dream, but you were checking your watch. And it took some real
personal work to figure out that that was a sign to take another leap. – Most people don’t do that. Most people come to that place, and they have that same experience
that you just described, but then they don’t do anything about it. The way they evaluate is like,
well, it’s working, right? So therefore, nothing’s wrong. They just kind of stay in that place. And they eventually, I mean
it was not good outcomes from there, they get burned
out, they get depressed, they just stop doing their best work. They get angry, or bitter,
resentful of their colleagues, of their boss, or whatever. All kinds of bad stuff
happens when you don’t pay attention to that voice, I think. – Have you always been
good at hearing that voice? Is that why, no?
– No, I don’t think so. I don’t know, I mean
that’s a good question. – You strike me as someone who, it’s like you move on at the right time. You’ve just announced that
next year will be the last. How do you know that next year’s gonna be the last one right now? That’s amazing to me! Like yup, that’s gonna be my last one. – It’s always good to end
things on a high note. Maybe it goes back to, it’s
like I had this experience of being in West Africa as an aid worker, living on this hospital ship. I saw some people that
were there for 10 years, 15 years, I was there for four years. With a couple of exceptions, couple of notable exceptions, I saw that most people who are
there beyond a certain point really did get kind of burned out. – Yeah. – For better or worse, they
were still doing good work. You could tell they weren’t that happy. And so, nobody goes into a situation, whether it’s being an aid worker, or your creative director
job, or whatever it is. Nobody ever goes into
a situation thinking, one day I’m gonna get real sick of this. – (laughs)
– If it’s a good, if it’s your dream job, – Totally.
– nobody goes into it thinking that right? – To be square, I still love
photography, for example. – Of course! – I just didn’t want to do it that way. So if you could love aid work- – That role, that’s the
point that role, that thing. So I kind of noticed, you
know, first two years, I absolutely loved everything. I gave everything to it. And then the third year
I could tell a little bit of a shift was beginning to happen. It was like, okay I’m giving 95%. It’s still pretty good,
but that’s different than the 100%, or 110 or whatever. And so basically, I was
like, I wanted to leave before I get resentful, or
burned out, or whatever. And so that was that, so maybe
I’ve kind of carried that forward in some ways, just some other stuff that I do now. It’s hard.
– Was there a time where you didn’t, you
took your battery down to five, or 10, or zero? – Yeah I was trying to think about that. – That’s helped you realize that, oh look. Just you’re self awareness, oo 95%. – Right. – That’s an extreme
sense of self awareness, that I’m still crushing it, but it’s not happening internally. – Well I was thinking about your question, have I always been aware of that? I think I’ve always been
aware of it to a degree, but have I always listened to it? I don’t know, probably not, probably not. If I think about
different times in my life whether it’s creative burnout, or personal depression or anxiety. Or maybe a sense of purposelessness, or a lack of self worth,
or various struggles. I probably have missed
something along the way. I can actually be guilty of, I really like to work,
just like you, right? I like what I do, I feel very fortunate. I get up and I’m thinking about what’s on my list to do. And overall I think that’s positive. The concern there is
that you’re just stuck in it sometimes, or you get stuck in it, you don’t realize actually
something has changed, either in the external environment, or in your own internal motivation. And you’re not paying attention to it, ’cause you’re just kind of going along. So I think I definitely
have a tendency to do that. – I love the sense of self awareness. Something had to happen though for you to realize it.
– Oh sure, yeah, probably lots of, something had to happen–
– Did you have, were you just like throwing
pizzas in high school, and you were like, “I really don’t want “to do this anymore?”
– Yeah. – Something had to happen where you said, all right, this is the last time I’m gonna let this happen. – I wasn’t ever really very good in the traditional appointment world. I kind of learned I was unemployable at a pretty early age. I did have a pizza throwing job actually for about three months. Then I kind of just
quit and never returned. But that’s how everybody
quits their pizza job, right? I don’t think everybody, this is my life.
(crosstalk) – Well actually give me a
handful of what are some jobs you had growing up? – So I mean it’s a short list, because it stopped at age 19. And then age 19 was the last job. I’ve always worked for myself since then. So I did pizza. I delivered some other stuff. I delivered like, you know, flowers on Valentine’s Day. – Oh wow. – Delivered phone books,
for anybody out there who remembers what a telephone directory, yellow pages was. – You used to just like
show up on your porch. – And it’s just a huge
waste, it’s a colossal waste, and they still make it for some reason. Then, oh I was a
telemarketer for two days. – Oh, what’s the story behind that? – Well it was a job, I was like- – Sure, I’ll dial for– – Yeah, and I was terrible at it, I never made a single sale. We were trying to sell
photography packages, actually. – No way!
– Yeah. Yeah some ridiculous photography package, unfortunately nobody bought. And so then I never went back, obviously. And then the last job was working at FedEx in Memphis, Tennessee, loading boxes onto a truck. Then I learned how to sell things on eBay, and I never went back to that job and never looked back at any other job. – What were you selling
on eBay at the beginning? – Well in the beginning
it was just random stuff from my apartment. – So this– – Yeah, whatever, a bunch of video games, clothes, stuff, I mean. Then I learned about
buying and re-selling. And I was like, let’s see what’s
selling on these auctions, what’s the price? What are the closing prices? What’s the source of these items? How can I buy these items? That was so fun. That was so fun to learn about. – How long ago was that? – 20 years. – (laughs) – 21, 22 years now, I’m 41. – It’s so funny. We know a handful of
mutual people that are trying to make a big deal
about how this is something you do now because you’ve
got this resource called eBay and you’re like, “Yeah, I was selling
shit in my apartment 20-” – I remember when
came out, you know? That’s one of my pet peeves
actually, people thinking that like, so much of this
kind of stuff is new. – (laughs) – Or that it’s Western, you know? It’s like America invented like, being a- – Buying one thing and,
the arbitrage model. We invented it, right? Buy something cheaply and sell- – We used to like, be in Syria. You’d walk out in a village
and every single person is reselling, buying
stuff, and just hustling and making their own way. Ladies were carrying all
of this stuff to the market and that’s how human society
has existed for centuries. We have a lot to learn,
you know, obviously. – The idea of like, vlogging has… Someone said something like,
“Yeah, yeah, this whole new “idea of having a video person
on your team to make videos.” I was like, “Wow I had a full
time video person in 2005.” – Wow, right. – It was very unusual then. – Sure.
– But it doesn’t feel like, when someone labels it as new. It’s bizarre. The arbitrage model, eBay. You’re like yeah, the flip life man. – Commerce, you know.
– (laughs) Commerce. – I mean it is true that like, it’s so much more mainstream
now and people are doing it in a way that they didn’t 20 years ago. Like you said when you were
doing it then it was very unusual, for me as well. Like when I was working for
myself, nobody understood it. My friends didn’t get it. Parents were like, “He’s doing
something on the internet. “We hope it’s not bad.” You know?
– (laughs) – But now it’s much more common
and e-commerce is adopted more and more places so it
makes it easier and stuff. But yeah, everything’s
an evolution in that way. – What about the folks
are home who are sitting and literally listening and watching. There’s a desire to do
what I think they think the right thing is. There’s so many things I could do. How do I know my thing? And you have a magic formula. It’s similar to ikigai in Japanese, where overlapping circles. My personal, and I cite you
often whenever I’m sort of talking publicly or in a
blog post, I said your name a thousand times in this context as, you have a fantastic system
for how to understand what you should be doing. Also, when to quit. – Right. – Can you share those with us? – Yeah, well I’m a big
fan of quitting stuff but let’s, yeah, let’s come back to that. So I think you’re talking
about this model that we developed a few years
ago for the “Born for This” book and concept, which is all
about joy, money, and flow. And so basically this model
is like you have to have all three of these in your
life to be truly fulfilled and there’s different times
where you might just have two or something. But really, if you’re thinking
about “What’s my thing?”, you need to be thinking about
all three of these things and so, you know, money is
pretty self explanatory. What you do needs to be sustainable. Joy is kind of what makes you come alive. What does make you happy,
what are you passionate about? And flow is essentially that
state of doing something that you’re really good at, basically. – Aptitude, and-
– Yeah, aptitude. Yeah, competence and even
beyond just competence, mastery, or the potential to master something. You know I often think of it
in terms so when people are like, “What should I do?” They always start with
the joy, and that’s fine. Make a list of the things
that you like to do, sure. But I think it’s just as
important to make a list of the things that you’re good at. Make a list of all your
skills because often these things are connected.
– Yeah. – We tend to actually really
enjoy the things that we are really good at.
– Yeah. – And often if you focus on
skills rather than passion, then that’s going to lead you
to something more marketable. Right?
– Yeah. – Which will kind of bring
in the money a little bit. So joy, money, flow. It’s always good to just
kind of evaluate like where are you at in your life right now? With your job, with your side
hustle, with whatever it is. How is that thing contributing
to all three of these areas? And where are you strongest and where are you weakest, essentially. And it could be a season thing too, right. It could be like, right now
I really need some money. I’m in debt, I got to deal with that. So all right, in that
situation maybe for a time you’re working a job that
you don’t really believe in or something. But you know that you have to
have your eyes on the prize. That ultimately I need to make a change, or else I’m not going to be- – Get out of your debt, get
out of this pickle or whatever. – And then the whole thing
about like, you know, quitting stuff. I noticed a while back that
people always assume that persistence is the key to success. This is very much an American
culture kind of thing of winners never quit, and
you hear the stories about people who… “He failed 49 times in a row.” And then the 50th time,
you know, he succeeded, which is so ridiculous
because you’re like, “Well, he could’ve been doing
all kinds of other stuff.” You know?
– (laughs) – All during the 10 years that
he was trying 49 different things, you know, I mean
like good for him that he figured it out eventually. But what did he miss along the way? And I see, my observation
is that successful people, and this has really been true for myself. Successful people have no
problem with giving stuff up. Have no problem with quitting something. Have no problem with saying,
“I tried that and I thought “that was a good idea but I was wrong.” Right?
– (laughs) – Or maybe it was a good idea for a time, and now I need to do something
different, just like you were talking about. So I think the key is not
persistence, it’s adaptation. The key is being willing to
like, ask on a regular basis, “Okay is this the right thing, now?” And if it’s not, there’s
a lot of value in just giving that up and moving on. Because life is short, right? – Yep. What’s your two question test? – Two questions. Oh yeah, when you’re trying
to decide if you’re going to like, “Do I want to
quit this thing or not?” Is it working, and do
I still believe in it? – It’s a very simple test. Super simple.
– Yeah, you make a lot of decisions that way. Is it working? Do I still believe in it? And if the answers are yes, then great. You keep doing it. And if the answers are no, then you stop. And so you only have to
think about it a little bit more deeply when the
answers are in conflict. – I was recently up at
5:00 in the morning making some notes about this thing. There’s this sort of confluence
of knowing when to quit. You talked about emotions
at the beginning. Like I want to do something
that brings me feelings and that other people might
share those similar feelings. I’m just more and more
over indexing on intuition, and what role does intuition
and sort of that inward listening to you gut, whatever
else you want to, you know, color you want to put around that. What does that play in your world? – Yeah, I think it’s very important. I think I kind of ignore
it at my peril, you know? But I also think it’s true
that over time you get better at listening to it.
– Yeah. – You know what I mean? Because in the beginning,
well I don’t know what the beginning is, but you know,
when you’re trying new things sometimes your gut can lead you astray. And sometimes your gut’s
like, “Don’t do this.” And you’re like, “I
should listen to my gut.” But if you kind of delve
a bit deeper, you’re like, “Why am I suggesting not to do this? “Because I’m afraid.” Well that actually means
maybe I should do it, right? So I think as you kind of get
to know yourself a little bit better, you understand what that is. But yeah, for me very much
now, if I’m evaluating do I do this project or this one. Not always but often, it’s kind of like what really makes me come alive here? What might have the greatest impact? What am I actually going to be good at? I think one of the problems of achieving a certain level
or being successful is that lots of opportunities
start to come to you. And so you think, “Well I should do that, “or I should do that.” Or like, “That sounds good.” And that worked for Chase,
so therefore I should do what Chase did, or for whoever. Of course you realize you’re
actually not going to be good at all these things. And just because the
opportunity comes to you, doesn’t mean it’s what you should pursue. And so I’m going to try to
listen to that intuition quite a bit. – I’ma change gears now. – Sure.
– That was very, very useful, very helpful.
– (laughs) – So one of the things that I have… I’m trying to ask more questions like this because we’re all at home
comparing our day-to-day or the worst parts of ourselves
to the highlight reels of everybody else that are on social. And so, like when someone looks at you. “Oh my God, he’s got six books. “New York Times best seller early on with “‘The $100 Startup’. “He’s got this huge conference. “He travels thousands, tens
of thousands, hundreds of “thousands of miles.” Like it’s very easy to look
at this life that you’ve been able to create for yourself. Chris is successful on every level. So to keep it real and balance
out, what’s hard for you? What’s hard right now? – Well I would say, I
mean, the very first thing that comes to mind is from time to time, not
infrequently, especially over the past five or six years
or so, but really like throughout my adult life and adolescence, I struggle with depression
and anxiety and lots of things that are correlated around that. And just a sense of
inferiority or a sense of… I like what you said
about you’re playing the highlight reels of everybody
else with your failures. I do that a lot and… – But the question that
someone in Ohio is asking right now, “But Chris,
you’re standing on stage. “You walk out, you don’t
even actually say anything, “and the whole thousands
of people stand up for you “and cheer, and you brought
all these people together.” – And that’s great, and that’s wonderful. But you know, you can have
these kinds of experiences and still have personal struggle. – Yeah.
– You know, you can still… I mean people who are much
higher levels than I would ever approach can have those
kinds of struggles too. So it’s not necessarily connected. Sometimes we just have to
like, go through stuff in life. Yeah, and I don’t know
if I have like a great five step answer for that. I think for me it starts
with just acknowledging that on a regular basis, I am kind
of like questioning myself where if I am kind of
like beating up on myself. You know, the answer is not
always just to work harder. The answer is not always
just to take on a project. I started doing therapy a few years ago. And extremely helpful to me,
I wish I had started earlier. If there’s anybody out there that’s like, I wish I had done it earlier actually. One of the things that I
learned really early on that I’ve kind of tried
to apply since then is, my first therapist said to me, she’s like, “Chris, you’ve been able to
do a lot of different things. “X, x, x. “Basically none of that’s
going to matter here. “What you’re trying to
accomplish now, these skills that you have learned are
not going to help you.” And that was very honest, you know? I was like, “Damn, okay.” I know how to send like email
marketing and I know how to post stuff online. The point is like, if you’re
going to do inner work on yourself then you have
to learn some new stuff. And so, I don’t mean to
derail the conversation- – This is exactly, this
is what the conversation needs to be about. That’s why I’m going here.
– Okay, good. – So keep going, I interrupted you. – Yeah I know, I think that’s… I was just saying, so
learning about self awareness. Understanding different
relationship styles, understanding how we form
these different styles at a young age and how that affects us later, understanding trauma of
childhood, which can be a lot of different things
for a lot of people. Understanding how we carry
that with us and if we never really deal with it, then it’s
going to always be with us. – Yeah.
– You know, basically. And so just in choosing to be
more intentional and kind of figuring that out, and by
the way it wasn’t like I was like, “Oh I’ve done all these things. “Next, I’m going to tackle my inner work.” It doesn’t work like that, you know? There’s like, what’s that quote about like the teacher appears
when the student’s ready or something like-
– (laughs) It’s almost like you start
working on this stuff when you’re in a hard
place in life, basically. When you have no choice, essentially. And I felt in particular,
I go back to a time. I don’t know exactly how
long ago it was now, but a couple of years when I
thought I had made a lot of progress and I thought I had
learned a bunch of stuff, and I’m like, “I’m doing better now.” I’d been on medication for
depression and I can get off it. And that actually ended up
being like the precipice to the worst time of all. And I didn’t see that coming. But that time like this
depressive period, kind of led me to take even a bigger,
broader look and say, “Okay. “What is it all about? “And I’m not going to do a
good job with anything else “that I’m doing in terms of
bring value to anyone else “unless I really actually
think about how to “care for myself.” That was surprisingly hard. – Yeah. But also brilliantly
insightful if you can like, catch yourself at a moment
where you can be that honest. – Eventually, at age 40, you know? I mean.
– Yeah. Well that’s your point,
you have to, right? You get yourself in a position where you, there’s literally no other choice. – That’s basically what happened, yeah. – Aside from, you talked about therapy. What are some other things that anxiety, that you helped
to, or that you find help you with anxiety? That’s, as I ask folks,
you know I get off stage after giving a talk and 50% of the people in
some way shape or form reference what I would call anxiety. Either their not doing the
right thing and their partner doesn’t approve of it, or
they’re trying to leave their job and their boss doesn’t
approve of them or their work, which causes them to-
– Right. – And I just put it all in
the bucket of anxiety, and I think there’s, this is sort
of the other side of this free life where we are able
to pursue the things we love and we have created, or
living a life for ourselves, that it’s all just a breeze. And the reality is that
there’s, I think, an increasing amount of anxiety. In part, because those same
tools that allow us the freedom to do what we want to do. They’re not always there just to help us. So punchline, a lot of
anxiety nowadays, and you mentioned it. What are, besides just
therapy, what are some things that you do to manage? – I think simple
observation is always good. For a long time, I went
through these states of anxiety without really understanding
what was going, I would just feel this anxiety, you know? – How did it manifest for you? – Yeah, how did it manifest? This is something that I
struggle with and kind of question in therapy because
I’m not very somatic in the sense of like, this is
how it felt in my chest and this is how it felt in my stomach. Which a lot of people can do.
– Yeah. – For me it was just like this
wave of uncertainty or chaos or confusion that kind of came with me. Or sadness, but it was
like the cycling and stuff. So I think just like observing,
being able to kind of step out and stuff and say,
“Okay I’m feeling this way, “but I have some experience with it now.” If it’s specific to something,
then I kind of understand. Like okay, here’s the situation. If it’s generalized, then
I know it’s going to pass. You know? I know it’s going to pass and
so I can make my peace with it a little bit. And just some really simple
stuff like exercising more and being really careful about what I eat. – Isn’t it weird how those
things are that simple? – It really is simple. – There’s this stuff that
is very nuanced and personal and has to be very specific things. And then on the other end of
the same spectrum is like, how are you sleeping?
– Yeah. – What are you putting in your body? – Right, right, right.
– How many, how many drinks a week are you having? – Which I mean, all of
those things make more a bit of difference as you get older, too. But even at any age, if you’re
struggling that’s always a good start. But I would say the number one thing is to not try to hide it. I don’t feel like I was hiding
it per say, but I don’t know that I was being super open about it. – Yeah. – So I think that’s helped. A lot of people around you
probably care about you and want to help you, but they don’t know what
to do or they don’t know what’s going on unless you show them. – Yeah.
– And so I think understanding that was also good for me. – Did you create some tools for yourself in order to do that? How have you decided to
like, “Ah this is something “I need to share.” – Well you know, it’s interesting. Because I just started being,
I was going to say more honest but I don’t want to say that
I was being dishonest before. I just started being more open and upfront about certain things. I don’t know if that
was always a good thing, because like here’s a story. – (laughs)
– So… – I love it when you smirk
and it’s like three sentences ahead, you’re like (mumbles) – I just remember this, I
needed to talk about this for a long time. So, I mean… In the summer of 2015, my brother died. And I know you know about
that and that’s something that’s, you know
obviously, understatement, affected my life a great deal. And that always will affect
my life a great deal. But what I was going to
say about the story is, it was like a few months later that I was doing some kind of
like businessy interview somewhere and I think
it was in San Fransisco. It was some Internet marketing
kind of thing or whatever. They asked, they were
like, “What’s your greatest “struggle right now?” And I was just like, “Do
you want an honest answer?” And she said yes, but
she didn’t really want an honest answer, but that’s what she said. And I was just like, “Well,
this is what’s going on “in my life, to be very honest with you. “Here’s what happened with
my brother and I still “don’t know how to process it “and I don’t know if I ever will. “And for anybody out
there who’s struggling, “let’s talk about it a little bit.” And the whole time I’m just
like, this is not the answer she wanted at all. – Her eyeballs are as
big as saucers, probably. – I kind of went away
thinking, I was like, I went away from that interview thinking, well I didn’t give them what
they wanted, but I was honest. I was really honest. She’s like, “What’s really
hard for you right now?” I’m like, “Well let me tell
you, here’s what’s hard for me.” It’s not nothing to do with
running my online business. It really doesn’t. It’s got nothing to do with my blog. It’s not nothing to do with all that stuff.
– Oh my growth is slowing or my email open rate isn’t- – Yeah, and if you want to talk about that stuff, that’s fine. – Yeah.
– But let’s just, let’s just say what’s
your greatest struggle when it comes to email marketing? As opposed to like- – Ask a better question, right? – You know, so. I guess what I’m saying is
like, to come full circle, is I just started being,
whenever people would ask, if they were really
asking me how I was doing I would say really here’s what’s going on. Which people aren’t always
used to or comfortable with. – I think you’ve always
done a fantastic job of bringing that sort of
awareness and openness in your community. You’ve bubbled that up really well. That’s one thing that,
having attended hundreds of conferences, maybe attended
thousands, spoken at hundreds. What you’ve done with the
World Domination Summit, it just feels very, very special. It’s sort of like you’re aiming
to celebrate those things. So, A, thank you for that. B, that it seems like out of the dispositions people
for really good work. There’s that internal
honesty that affects the gut. The gut affects you, then
you work on the right things. You pursue what you love. You realize that time is short. There’s this sort of personal
authenticity that I always walk away from any time
we get to hang out. Even beyond when we’re recording (laughs) a podcast. I’d like to shift gears again now. Thank you for sharing that.
– Of course. – So sixth book.
– Mm-hmm. – When I saw that you’d
launched Side Hustle School and that you were doing
a podcast every day, like every single day, I
was like who does that? – You would do something like that. – (laughs)
– You would. – I’d do it for very small bursts. What was it, we did 30 days of g’s. 30 days in a row, I was like all right, and these were like hour long interviews. You were aware of that. But 30 days is not how
many, how many episodes into Side Hustle School? – At the time we’re making this
episode, this conversation, I think I’m on day 873. 8-7-3, yeah. – (laughs)
– I haven’t missed day. Seven days a week. The streak is really powerful. The thing is the streak keeps you going. It would be harder to stop
now than it is to keep going. Right?
– Yep. – So for me it’s actually
beneficial to do it every single day. It would be harder to do it
two to three days a week, for me. Because I would just forget about it. You know what I mean? If it’s every day, I
can’t forget about it. If it was just like one of many projects, that would not be good.
– Do you literally record them daily or do you sit
down and bash five or six? – I actually record almost every day. So I will batch occasionally,
but batching for me is more like, two to three
episodes as opposed to like, I’m doing ten at once or something. Pretty much every single
day, I’m recording. I have a setup that comes
with me when I travel, and so I’ve actually kind of- – Is it in your backpack over there? – It is not in my backpack,
but it’s in my carryon bag. – Okay, back at the house.
– It’s small, you know? I actually like the routine
and the ritual of like, okay I got to do this, you know? – What made you decide
to do something like that every day? – Okay well I mean let’s
talk about why I did the program in the first place. It’s called Side Hustle School. – Right.
– And it’s all about regular people, not necessarily
people like you and me who are like, want to be
entrepreneurs and unemployable and all that, but regular
people who have jobs. You’re right. People who have jobs and
don’t necessarily want to jump into the startup culture thing, but they understand that it’s
good to have more than one source of income. And so, and how do they do
that, because so many resources these days are targeted
toward entrepreneurs or people who are aspirational entrepreneurs. It’s very much about like,
quit your job and go, you know. – All in.
– Right, all in. Right, and so there’s like
a huge group of people who, for whatever reason,
can’t just go all in or quit their job, or they
actually like their job. They actually enjoy what
they do and they like working with their
colleagues or on the projects or whatever. I kind of think about my mom. She worked for NASA for I
don’t know, 20, 30 years. You can’t be a freelancer
working for NASA, you know? – (laughs)
– On upwork or whatever. You’ve got to commit. – Please design shuttle fin.
– Right, right. A $150 bin, you know? (mumbles) So for anybody in that
situation, how are they supposed to learn about starting a little business, which I believe you can
do without spending a lot of money, without going into
debts, without following this traditional path of
you know, startup culture. So anyway, that’s the whole
point of the show, is to show different stories. A different story, a different
example every single day of somebody doing that. I’m not even teaching that much. I’m just storytelling. It’s 80% storytelling, maybe 20% like- – That is part of what I love about it. – Well I think nobody was
doing that either, that way. You know, and so that’s part of it. And then why seven days a week? I just, I like to commit, or I like to… Just like, what would
make it badass, okay, every single day. I remember talking with the
CEO of the podcast network that we work with and we had
like three conference calls with him. And on the third call, he
still didn’t, he was still like every single day, that’s
like five day a week. That’s a lot. I was like five days a week? How many days are there
in the week, you know? Seven days. So that’s why every day. – Can you tell me a little
bit more about the back end? Like who you’re working with and are you working with a CDN or an MCN? I’m sorry, CDN, MSN or did you find someone to
partner with for people at home like, “I want to get started.” I guess my first advice is
just start recording things before you start sharing them. Make five episodes only
you are listening to. But how have you though about it? Because that’s, you know,
what’s the publishing platform and how do you think about it? Go a little bit of detail for me. – I wasn’t actually sure what I was going to do in the beginning in terms of am I going to be on a network? Am I just going to do it all myself? I didn’t even have ad
mole, I was just like, I’m just going to make it. It just so happened that
a good friend of mine, Gretchen Ruben, came to me. I think you know Gretchen right? – Of course, yeah.
– Of course, yeah you did that thing with her.
– She’s awesome. – Came to me and said, “I’m
starting a little imprint. “Have you ever thought
about doing a podcast?” I’m like, “Gretchen,
funny you mentioned that, “because I’m actually outlining
this project right now. “But it’s really specific,
I don’t know if it’s going “to work with your vision.” But anyway, so I ended up
kind of looping in with her. And then we were part of
a network called Panoply for the first two years and then this year we switched to a different one. So I have a producer,
thankfully, because I don’t do any audio editing. I’m not good at that stuff. – You just send raw files off? – Yep. So it’s actually not a ton
of editing that’s really required in my show because it’s just me. I’m not doing interviews.
– Yeah. So you’re just talking
or do you write a script and then read the script, like how- – Yeah I have a script, yeah. Now we have a team of writers
actually that’s working on the stories.
– Wow. – So I can’t take all the
credit for that, either. But I obviously am doing the
analysis on the final edits and all of that. And I have a wonderful
assistant, who now has kind of migrated to the role of
content manager, named Whitney, and she’s actually been with
me for all 872 or 73 episodes. – Wow.
– Kind of working with the people who are featured and
then fact checking and like, doing all the different stuff. I’m definitely really grateful
to have those folks around. – Wow, amazing. And clearly fuel for
your new project here. – Yeah, oh exactly.
– We’re just going to have a look at this beast. Look at this thing. This is, well first of
all, I’m going to… Four color. – Yep, 330 pages.
– 330 pages. Hard back. A, gorgeous, nice spot
varnish so that designers in the world are going
to be happy with this. Feels really cool.
– Mm-hmm. – But obviously, the meat is
300 stories, or 300 pages. 100 separate stories of
people’s side hustle. Is the book 100% mirror of the podcast? – It’s not 100% mirror. All of the stories come from the podcast, but a lot of them have updates or- – God, if there’s 800 of
them, you chose the top 15%. – Yeah, we chose a lot
of the most popular ones from the first year, in particular. So I wanted to show the stories
in addition to telling them so it’s like this visual
depiction of a lot of these different people that are
doing different kind of creative, unusual things to make money. I try to be really
specific about it because I feel like there’s a lack
of specificity in this world often and so I try to be really specific. Like, it cost them $150
to start their business. At the end of year one,
they were making $24,000 or whatever it is. I want to be really just clear
about the practical details. And so the idea is like,
people can just kid of flip through it. I mean, you can read it cover
to cover or you can just kind of flip through it and
see what resonates with you. You’re not going to connect
with all 100 stories, but I really would be surprised
if somebody reads this and doesn’t find a couple
of things and they’re like, “Oh I want to go and do
something like that.” You know, and that’s my
whole motivation with it. – That’s the motivation, is to provide a menu of ideas that, yeah I got it. – Jumping off point to
know some inspiration. A lot of the stories that
we feature on the show now are coming from listeners
who were listening in the first season or the second
season and have started their projects, which is really cool. – Like, “I want to be on the show. “Here’s my idea.” – I don’t think that was their motive. I think they were trying
to actually make money for themselves, you know. But secondary benefit, being on the show. So I’m hopeful that when
people read the book, same kind of thing. – But it is a, it’s beautiful, it’s giant. Huge great photography in there. – Well again, a team effort, relax. I’m not traveling the
country taking photos. That’s not my skill. A wonderful interior
designer, Ian McCampian, he worked on that, all that stuff. A lot of photographers, a lot of people. – Huge, huge. Most surprising side hustle? – Most surprising-
– Well, I hate superlative questions, so I’ll restate that. A couple of just surprise,
that surprised you. – A couple of people tend to enjoy… There’s this guy who’s like,
drop shipping live crickets to reptile owners. So there’s a market of people
who are buying live crickets. They need to feed their reptile. And so he gets into this
business, but doesn’t actually like stock the inventory. So he works with cricket
farms, takes the orders in, processes the order,
and does that, you know. He’s making like $1,000 a
month or something doing this. The funny part about this story,
if that’s not funny enough, is one time in the beginning, he’s like, “I should actually order
once, to see what the product “is like, just for quality control.” And so he orders a batch
of crickets from the farm, and the crickets arrive. And there was supposed
to be some instructions that are included, but
he opens the box and they’re not there. And then he learns that the
crickets will eat anything that has paper in it. So from that lesson, he’s
like, “Oh I can’t include “any instructions. “I need to email them, the
instructions need to be digital.” So I got the guy doing that. There’s a woman in New York
who has this business called Troll Cakes. Troll Cakes Bakery and Detective Agency. And so every single day,
she is baking a cake. This is a good story for
anybody out there who’s ever had like a negative comment
on Facebook or a hurtful comment directed to you. She’s baking these cakes
and she frosts them with the negative comments written on it. So it’s like, “You’re going to Hell.” Like, “What’s up with your hairstyle?” You know, “How about that
contract you made with Satan?” And then she mails it to the
person who left that comment. And she calls it Detective
Agency because for an additional fee, if you don’t
know who left the comment, she’ll find their address. – No.
– Basically. And she’s doing this every single day. We got a whole gallery of photos. So that’s like, you know,
never would imagine people would get paid to do this.
– (laughing) Oh my God. – And this isn’t her
retirement plan, you know. But it’s like a crazy thing
that she’s doing and she’s making some money with it
and she’s going to have this story for the rest of her life. – Can you give me one
more level of detail? – One more level of detail? – On her like, I don’t think I want to
reveal the source of how, because that sounds like
it could get into some gangster shit. What is the cost to send a troll- – Oh it’s pretty cheap actually. I think it was like 50 bucks
or something, you know? Something like that.
– You have a human bake a cake and frost it with the comment
and then mail it to them. – Yeah, and you’ll get a
picture obviously so you can post it if you want, or
not, or whatever, yeah. – Wow.
– You know? And some people are doing
it as a joke of course but I think it’s also kind of like, can you imagine if you’re
the person who’s like leaving these jackass comments on people’s Facebook or whatever. I think she started
when she read something on Dolly Parton’s blog and
somebody was criticizing Dolly. It’s like why are you doing that? And people like Britney
Spears, “You need Jesus.” All this kind of stuff, so can you just imagine getting
that in the mail and like, it might actually cause somebody to think. Who knows? – Wow. All right, I’m looking for trends now. So those were interesting. – Yeah.
– Give me some trends. Most repeatable possible,
most common, solid, middle of down the road side
hustle where people can like, hey, most people can be
successful with this thing. – I’m glad you asked, actually,
because I like telling the kind of crazy stories,
but I’m not trying to tell people they should go out
and do this stuff, you know? It’s just kind of like-
– Cricket farming is a little esoteric. – Right, so we talked a
little bit about reselling. So anybody can buy and resell. Anybody can buy something
and then resell it. There’s lots of different
models to do that. I think that’s actually
the number one suggestion I would make if somebody’s like, “How do I get started
with a side hustle now?” You can do this right now. There’s all kinds of
stuff that you can do. Lots of platforms for that. Also a lot of service businesses, of like, there’s something that you’re good at and there’s somebody out
there who needs help with it. There’s a guy in the book
who, he’s lived a lot of different places around
the world and now he’s got a family. And so he’s often meeting
other families who are like, “I want to bring up my kids
in different countries, “but I don’t know. “I got questions about
education and taxes and “vaccinations and all kinds of stuff.” So he’s doing like consultations for that. There’s a woman in, I think
it’s upstate New York, who she’s got a few different sisters. She’s got three different sisters. She was part of a couple
different wedding plannings, and notices that all
these wedding accessories are super expensive, like
the veil and the tiara and then whatever else. And she’s like, “Why isn’t
there a rental market “for these things? “Nobody’s doing that.” – And what do you do? You’re going to hold it, you’re
going to keep your thing? – Yeah, do you need all
of these keepsakes for the rest of your life? You got the dress, that’s
enough of a racket right? But here’s like all this other stuff. So she starts a business
called Happily Ever Borrowed. And she’s like renting this
out to people all over the country and she’s really got it. She did like $80,000 last year,
you know, as a side hustle. So also I should point that
out, a lot of the stories, they’re not people that are
just making a few hundred dollars a month.
– Yeah. – Like a lot of them actually
are six figure incomes. – Wow. – Or even more in some cases. I’m trying to help people
truly get ahead and truly create an asset for themselves, which you’re not going to get
by driving for Uber or Lyft. – Yeah.
– You’re not going to get it by participating in the gig economy. To really create something
for yourself, you have to actually make something for yourself. And it’s not as hard
as people think it is. – Do you have… Baked in that last little
phrase, like it’s not driving for Lyft. It sounds like you’re into
value creation for yourself on some sort of beyond just
transaction time money. But what are your biases
on steering people towards or away from… And I think this is,
honestly, this is the perfect, you’re such an amazing guy,
so anyone at home is like, taking notes like crazy right now. You really, you know,
the creative audience is, you know how to speak their language. But give a little bit of council. – So a couple of questions you
can ask yourself, you know, about any different idea or opportunity. Does someone else control all the rules, the entire environment
for this opportunity? Which is how it is for the
gig economy, with all these different platforms. If they do, that’s not a bad part time job but that’s all it is. So just understand, that’s all it is. – Give me an example. – Well again, like
driving for Uber or Lyft. You know? That’s not bad to make
extra money and you can set your own schedule, but
then they’re setting your competition, they’re
capping your compensation. You’re not going to have
the chance to earn money while you’re doing something else. You are trading time for money doing that. So I mean, ultimately, so
let’s say the next question is does this have the potential
to earn money for you while you’re doing something else? And this is I think the
greatest thing in the world is to like wake up in the
morning and check your email and somebody has sent you
a PapPal payment overnight. Or a Venmo or however it works. I mean, that I think is,
that’s the goal, right? So whatever your
opportunity is or your idea, does it have the potential to do that? That’s great, so are you
in control, does that have potential to earn some
sort of passive income even if you have to then
do something for it. And again, is it something
you’re excited about? Is it something that’s
really bringing value to other people? It has be not just interesting
to you, but interesting to other folks. Has anybody done it before? And if so, that’s not bad, by the way. If somebody has done your
idea before, that doesn’t mean you can’t do it. It’s actually probably a
good sign because it shows there’s a market for it. I’m trying to think what else. Those are, that’s a good start. – Yeah, that’s deep. There’s plenty, I mean, it’s
a lifetime of stuff there. You said something earlier,
you see you tried ten of those things, you’re like… You talked about this, we
talked about the intersection of what you love, what
you’re good at, and I think all of those probably are still in play. But this idea of scalable
making money while you sleep, not transactional. I’m going to bring something
you said early, early on into the picture, which
I think is just genius, and I want you to tell me about it. It doesn’t have to be big. – Absolutely.
– It doesn’t have to scale. – It probably won’t be big at first. That’s good.
– Talk about this. – Not only does it not have to be big- – They’re like, “Wait a
minute, I want to be able to “make a million dollars, Chris.” – Well, great, maybe you will. But if you’re not making
any money at all now, start with making $100. Start with making $1,000 because one, it can lead to something
else but also, just on its own, that thousand dollars
is going to feel really good. If you have never made
money for yourself before, the first time you make
a few hundred dollars, the first time you make like 50 bucks it’s going to feel good. I know that. I’ve heard these stories over and over. On my book tour, I ask
people like, “Raise your hand “if you’ve ever been paid
for something apart from “your paycheck.” And probably like half the
audience raises their hand, and then I ask, “Do you
remember when that happened?” Everybody still remembers,
like so many people. It’s this memorable thing. So it doesn’t have to be big,
in face it probably won’t be. And also, just remember
that you’re not making a lifetime commitment, which
is another reason why people don’t start projects. ‘Cause they’re like, “I
don’t know what to do because “it might not be the
right blah, blah, blah.” It doesn’t matter. This is not a life partnership
kind of situation here. You’re trying to decide
what is the project that I start right now. That live cricket dropshipping
guy, he’s not going to be doing that forever but that’s okay. All these projects, maybe they’ll go on to be huge businesses. In lots of cases, they’re
great learning experiences. They’re bringing in a lot
of money, they’re bringing them security and options to go on and do something different.
– Yeah. – So it doesn’t have to be
big and it doesn’t have to be a life commitment. – In fact, it sort of
shouldn’t be big, almost. – Yeah, absolutely. – I think of everything on
any sort of side project that ever turned, I mean
Creative Live was a side project. – Yeah, right.
– You know? Or I think of getting on
back, even taking pictures on my iPhone, that was cool,
and I went and did an app. And I think, it’s interesting. It’s almost the things that
were started without the pressure of desire to make them
big, had the most potential. Is that a commonality or-
– Yeah, that’s interesting. Yeah. I’m trying to think, most people that… ‘Cause most people in my world
are not from that startup culture, you know? So most people that I tend
to encounter across middle America or wherever, they’re
just, they’re out there trying to do something for
themselves and for their family. For them, the motivation
is how can I have options, how can I have choices so
that if I don’t want to go to my job anymore, I don’t have to. Or if something changes at my job. Like I’m enjoying it now, but what if that situation changes? Then I’ve got some security
to do something else. So it’s not so much about
like, I’m going to build a huge company as it is. I’m going to do something for myself. And so I’ve always, all of
my work is for individuals, not companies. I think that’s a key distinction. There’s lots of people doing
lots of wonderful work for so-called more experienced
or skilled entrepreneurs who have built large organizations. And that’s not me, because
I’ve never done that myself. But I’ve spent more than
20 years making a living without a job, essentially. So that’s what I do. – What were some of the
most surprising things from the research to
put together the book? – Yeah.
– Was it, was there some weird commonality? Was it geographic? Was it particular attitudes? Was it fear of some fear? Like, what were- – Yeah, yeah, good, let’s go. I’m just thinking so I can
give you a real answer. I mean, I would say to
your last point about fear, very, very common to hear, “I wanted to start this for
a long time but I never did “because I thought I wasn’t
good enough, or I thought “I was missing something. “I was missing X.” Whether X is like money
or access to something or just permission, essentially. Like endorsement, you know,
like “Hey go do that, Chase.” You know? A lot of people say that,
and they’re always like, “I wish I had started sooner.” I think another commonality is like, this blend of curiosity, the
willingness to say what if. “What if I could actually
make money doing this thing?” “This service sounds kind of
crazy, but what if it worked?” So that’s the curiosity factor. But then you can be curious
and never actually do anything, so the combination of
curiosity and willingness to take action, like the
willingness to actually do something with it. So you’ve got lots of people
that are like, charging ahead, but they don’t really have ideas. And you’ve got the people
that have all the ideas but aren’t doing something, and
so I think the commonality is like, you’re practicing
your skill of observation, which you never really
learned in school but it’s not that hard to learn. It’s just, pay attention, you know? Pay attention, and then
you’re willing to kind of follow up on what you noticed. I think that’s what leads
people to start these kinds of projects, and the
ones who succeed do that. The ones that are just
kind of on the outside don’t take action. – Amazing. And this is, did you have a favorite? – No, I don’t. That’s kind of like everything. Favorite country, you know. I don’t know, well there’s
a story I’ve been telling about this guy who makes
teddy bears dressed up in Marine uniforms or Army
uniforms, and he calls them like Sargent Sleep Tight. It’s to help kids sleep better at night. Especially for military
families and families with one of the parents is deployed
overseas and the kid’s having a hard time sleeping
and so he makes these teddy bears and like, the
bear’s going to watch over you at night. So that’s just really cute. He’s got all these good stories from it. I like it as well,
because this guy was like a copywriter. He didn’t have a Master’s
degree in making teddy bears. He’s just like, “How do I do that? “How do I learn to source,
how do I learn to source “my product from an overseas manufacturer “or from the US, and then
how do I distribute it?” All that stuff is, like
you can figure it out. There’s a path to figuring it out. – What’s the best resource? Clearly, you’re starting
to see patterns in like, oh everyone needs a
Shopify account or like, what are some resources
that you see time and time and again that if people
are asking questions or wondering like, “God,
I’d like to do that.” There’s probably ten buckets
of things, but what are some popular buckets and
what would you recommend? – Yeah, I think it kind
of depends on what project you want to have, right? So if you’re like, e-commerce,
okay I got a product. I’ve got this thing I’m going to sell. Got a guy in there who did
like, anti-mosquito wristbands and like, ends up making
a lot of money with that. So for there, like a Shopify
site or something else. Some kind of e-commerce platform. We’ve got some projects that
are really content driven, like blog driven. Okay, so you need a blog. You need a website. Lots of different ways to do that- – Do you have some recommendations? – $10 a month.
– You mentioned Spotify, or Shopify. Do you have a particular- – I mean I’ve always worked
with WordPress, you know, for most of my Internet life. has like
a moderate charge to it but WordPress itself is free, open source. It doesn’t cost you more
than five or ten dollars a month to have a hosted
account somewhere. So you probably need an
email list of some kind. Stuff like this, I’m not going
to say it’s not important, but I just think it’s
very easy to figure out. People get hung up on that
stuff, and I don’t think that’s where they should get hung up. Does it really matter? Does it matter which
email list program you, not really, there’s a whole bunch of them. Does it matter? Nobody cares about that from the outside. I have to remind myself of
that as well about like, book publishing, because
I’m really into like, I’m a geek about book publishing. I know all the nuances and
stuff, and my literary agent has to remind me from time to time. He’s like, “Readers don’t care about that. “Readers do not care who the publisher is. “Readers don’t care about
the knitty-gritty and “the behind the scenes.” I’m like, “Oh that’s good to remember.” So same for all your
online business stuff. They don’t care about that. Your customer doesn’t
care whether it’s Shopify or something else. They care about, do you have
a product that they want. Is it clear how they
can give you their money to receive that product? If yes, then they’re good. If not, they’re confused. – And then you can help them. So you are famous for
doing mega book tours. – Yeah.
– Mega book tours. Like every 50 states. – That was great, that was great. – That was fun.
– All 50 states and every province in Canada, I
did that on my first run. That was 63 cities, it was great, epic. I should do it again. I feel like I’m a slacker,
I’m just doing 14 cities for this tour. – Which is seven more than 99% of authors. – Yeah, most authors don’t do it at all, but I think they should. I learned so much through
this process and talking with my readers, and it’s not
so much like a strict economic thing, you know, it’s
like in Denver last night, 100 people, we sold 40
or 50 books or something, but like think about what
it costs to travel there and the time investment. It’s not about the economics,
it’s about the conversation and the interaction and that
first tour, when I went to North Dakota and there were
10 people, some of those are still with me now. Like it made an impact on those people. Some of them are still following me. I’m doing 14 cities because I
have World Domination Summit coming up and so it’s kind
of bookended because of that, so I’m hoping I can go back
out later in the summer, in the fall, and do some more. – World Domination Summit,
there’s only a couple left. This year and next. – Yes. – Any tickets left? – We got maybe 10 tickets
for this one, which is coming up very soon, if you might
be watching this later. And next year might very
well be sold out because a lot of our alumni want to come back. But you can check it out, – Where else, if people are wanting to, is it like, to book sites
or to you personally? (mumbles)
– Yeah it’s all a mess but you know,, which nobody can ever spell- – I can spell it.
– Can you, yeah you can. That’s good, I can spell your name too. That’s cool. – That’s true friendship right there. You know how to spell your buddy’s name. – Especially mine, that’s true friendship. Or, the podcast is at, or
Apple Podcast or Spotify or wherever people listen.
– Wherever you listen. And next big project that you
haven’t talked about publicly. – I’m not unwilling to say,
I’m just kind of in the mist of this right now. I will say I want to do a
different kind of writing project, I will say that. – A different kind of writing project. All right, well congrats on the book. It’s a beast, it’s beautiful. There, like it is very well documented. I was shocked at the level of research. Shocked. Interviews with 100 people,
photographs, all the details, income per year, websites,
URL’s, fun facts, like it is a research beast. – Team effort, like I said. – Congratulations, man. Thank you so much-
– Thank you, sir. Thank you, Chase. – And good luck tonight on your book talk. – Awesome, cheers.
– What’s your next couple of locations? – Where am I going next? I don’t know when you’re-
– Yeah I don’t know how soon this is going to come out, oh my gosh. But just so the people
knew that they missed you. – Right, great, next week
I’m on the east coast, so New York, Boston, I
think back to the south, and then Canada the following week. – Got it. Awesome. Canada. You’re next week, Canada. Thank you very much for being on the show. Super happy you’re here. Congrats on the book.
– Cheers man, thank you. – And thanks for being a guest again. This is the second or third maybe. – Second.
– Second? Dang (percussion sounds) Check out Chris, all on the Internet. He’s also got a couple of
amazing Creative Live classes. Travel.
– That’s right. Make your dream trip a reality. – Yeah.
– It was actually really fun to make that course. – That was, it’s- – Still got people watching it, actually. – Yeah, still getting those checks. – Yeah. – Wait a minute, people are,
that was three years ago. – It’s got a find my trip
to Denver to talk to people about the book. – It was like, you’re the master mile. How many miles do you have right now? – Now like, a couple million or something. Miles are always being devalued
you know, so you got to like, use them, right? – Sorry this is the slowest
ending to a podcast ever. I literally just keep
thinking of things I want to ask you about. Thanks for being on the show, bud. – Awesome.
– Appreciate it. – Cheers.
– Bye, everybody. See you again, hopefully,
or hear you again. Or you know what I mean. Audio you tomorrow. Signing off, till then. (electric music)

9 thoughts on “Adaptation, Self-Awareness and Art of the Side Hustle with Chris Guillebeau

  1. Thank you thank you thank you! I’ve wanted to figure out a side hustle for a little while now, but I wasn’t sure where to start. Just ordered the book and can’t wait to be even more inspired. Thank you both for all you do, you’re amazing!

  2. I just started selling furniture and things for friends for the past 3 weeks. This video came out in perfect timing! Thanks

  3. Really good call on: "You can have these type of experiences and still have personal struggles", thanks for being honest there. It's often forgotten in many of the news stories. Cheers.

  4. Fantastically real conversation! This is humanness in all its greatness and vulnerable places. Happy to see more of this rather than the peak performance gurus claiming to have it all figured out.

  5. Thanks for this amazing interview. What a guy. Chase I remember seeing you at WDS a few years back talking about Creativity and it's great to see you still on that mission – ideas the world needs to hear.

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