Chris Guillebeau, New York Times Bestselling author of The $100 Startup, The Happiness of Pursuit, and The Money Tree talks about building an audience, the importance of serving your readership, the importance of discipline and why to have more luck you need to take more chances.
So you've started a blog, written a book. What next? How can you find your first 100 readers and grow that to 10,000 and beyond? Chris Guillebeau talks about how he grew his audience, one by one, from zero readers to thousands hanging on his every step. He's authored multiple New York Times bestsellers. And today when he launches a new book product or even an event, it sells out instantly. Join us for our conversation with Chris Guillebeau about becoming a disciplined writer, building a global community around your work, and making it as a full-time writer.
ABOUT CHRIS
Chris Guillebeau is the author of seven books. His first book, The Art of Non-Conformity, was translated into more than thirty languages. His second book, The $100 Startup, was a New York Times and Wall Street Journal bestseller, selling more than 700,000 copies worldwide. His newest book, The Money Tree is all about finding fortune in your own backyard. He’s also built Side Hustle School, a wildly popular podcast with more than 2 million monthly downloads, to help people create a new source of income without quitting their job.
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SHOW NOTES
[03:04] Chris talks about his secret to getting an NYT review
[04:28] Chris talks about his relationship with role models and the people that inspire him
[07:39] The core components of being a writer, and the importance of serving others
[10:36] Discipline as part of being professional and how doing things every day is sometimes easier than doing them less frequently
[13:53] The abundance mindset and why this is important
[17:16] Chris talks about what it's like transitioning from doing book tours to doing everything online during the pandemic.
[20:28] How to allocate time to finish different projects without feeling overwhelmed
[22:25] Chris talks about where he generates more income
[27:02] Chris shares his thoughts on monetizing his works
[29:21] How to build and grow an audience
[32:47] Blogging before vs now
[34:26] Chris shares his approach when it comes to talking about a difficult subject
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QUOTES FROM CHRIS GUILLEABEAU
“A guiding value has always been — there's gotta be something I can do today to help somebody … it could be highlighting other people's projects. It could be like doing whatever you can to get someone else to have attention or whatever it is.”
“The other secret about the podcast is it would be easier for me, or it's easier for me to do it seven days a week than it would be to do it like three to five days a week. Like if it was like Monday, Wednesday, Friday, it would be harder than every day because every day it has to happen, right. Whereas if it's on like a staggered schedule, it's like, oh, you just kind of get off the rhythm.”
“And so the only thing you can do is take more hits or try, you know, like you take more chances. That quote about, like, to be luckier…I'd like to have more luck, take more chances”
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“Most of the time I'm not selling anything. Like most of the time, it's like for months or years go by without doing much. The podcast is free. The blog is free. Other stuff is free. I'm not really working on trying to build out that part of the online business. So I guess when the time comes to launch the book, I don't hesitate to push it a little bit because I mean like I said, I know that that's going to help people, and then I know it's going to help me as well.”
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“...[A]nybody who joins my email list, that person has chosen to give me like their most valuable asset, which is their time and their attention…As much as possible, I want to build individual relationships with those people… And so for the first 10,000 people that joined over the course of, I don't know, two years, I wrote to each one of those people. Not just like an autoresponder, but I wrote an actual email to those people, and said, “Hey Matt, thanks so much for joining”, you know, “Hope you like it. Let me know what you're up to.” … [I built it] one by one.”
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SELECTED LINKS FROM THE EPISODE
Connect with Chris Guillebeau
Website: https://chrisguillebeau.com
Twitter: twitter.com/chrisguillebeau
Instagram: instagram.com/193countries
Gretchen Rubin & The Happiness Project
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CREDITS
Production by Victoria Spooner. Artwork by Emma Winterschladen
Matt: Hello, and welcome to season one of the London Writers’ Salon podcast. I'm Matt.
Parul: I’m Parul, and each week, we sit down with a writer that we admire to talk about the craft of writing and the arts of building a successful and sustainable writing career.
Matt: These interviews are recorded live with our global writing community. If you would like to join us for the next recording or write with us at our daily Writers’ Hour writing sessions, head to londonwriterssalon.com for more info. In this episode, we interviewed podcaster, entrepreneur, and New York Times bestselling author Chris Guillebeau. Chris’ entry into writing began as a blog, documenting his quest to visit every country in the world, 193 in total, before his 35th birthday. Chris has since authored seven books.
His first book was The Art of Non-Conformity, which has been translated into more than 30 languages and helped usher in a Renaissance of people living life on their own terms. And this was when I heard about Chris. I started following his blog, I read that book, and it really did shift my mindset with a bunch of things.
Other books by Chris included The $100 Startup and Side hustle. Both really wonderful books as well. And his latest book, The Money Tree, which is a parable about finding fortune in your own backyard. Chris also hosts a daily podcast called Side Hustle School, which has been downloaded more than 40 million times in which he's been posting and recording every day since he started it.
Parul: We're so curious about how Chris manages to produce so much and how he spends his time managing his different projects. So we really explored his mindset. We went deep. We asked him about his relentless focus on serving others. We talked about his discipline, why he strives for momentum and why he believes that writing or podcasting every day is sometimes easier than doing it less frequently.
We also asked Chris about how he grew his audience and what Chris would do if he was starting a blog today. We talk about the abundance mindset that runs through all his work. Really, he's so generous with his readers. And we talked about why that is and how that helps him stay focused and enjoy his work.
We asked Chris about where his income comes from. We talked about his thoughts on the different platforms that are out there, from Facebook pages to newsletters, blogging, and the medium of podcasting.
Matt: And Chris was super candid with us, and we really appreciated having a peek into his thought process about all of these. This conversation was recorded in front of a live audience of writers during the lockdown in May 2018. And without further ado, we really hope you enjoy this conversation with Chris.
Parul: We like to start off by talking about how you got started and your origin story, but one thing that comes to mind before we get into that is that you've been a New York times bestseller multiple times. So it's one thing to be a New York Times bestseller, but it's another thing for the New York Times to review your book, to have a featured review. So what's the secret of getting a New York Times review?
Chris: Right, right. They just reviewed the recent book, and I think I said on Instagram, the secret is you write six books that they ignore, and then the seventh one, you know, all of a sudden something happens. And the other thing is like for the first six, you do everything you can.
So like pitch it and like push it and then nothing happens, you know? And then you just kind of give up on the seventh one, and then all of a sudden, something shows up. So that was my experience.
Matt: I love that, Chris. Well, first, I mentioned this to you before we started, but you might be, I think, the guest that has gotten the most excitement when we announced that we were interviewing you.
So you've inspired a lot of writers here in the room, me included, and your journey is one of the guiding lights for me. And I used to work in Chicago in a corporate job, and I came to see you on your book tour in Milwaukee for [The] $100 Startup. It was right about when I was about to leave my job at IBM and start to travel and eventually launch a new career for myself.
And so I guess first, just on behalf of all of us, thank you for the work that you do.
Chris: Thank you. Thank you for saying that. Yeah. Expectations to live up to, though. So it's better to start with like a low standard, and then, well, he actually does something that's helpful, you know, but anyway, continue.
Matt: Yeah. And so, I would call you a role model, not only for me but for others. And I guess I was curious about…what's your own relationship with role models or heroes? Was there anyone that served as a guiding light for you either when you got started, and I guess even now, are there any people that you look up to and are guiding light role models for you?
Chris: Yeah. So I think broadly speaking, a lot of what I try to do is about self-reliance and helping people kind of consider different possibilities or options or realise that there is a non-traditional path; there are multiple nontraditional paths. And if you're happy with the traditional path in any given avenue in life, that's fine.
But for everybody else, you know, if you're dissatisfied, then it's important to know that there are alternatives out there. And so, I think a lot of self-reliance is that you don't necessarily look to other people for mentorship or for guidance. It doesn't mean you can't learn from other people, of course. Like I've learned from—I'll learn from this conversation, I hope, you know. But it's a little bit different than like, the role model of like, this is the path, this is the thing I'm going to kind of follow and such. So for me, it wasn't so much about other bloggers or authors. I mean, there certainly were some that influenced me. For me, it was more just like my life in general. I was an aid worker for several years, and whenever I think about people who influenced me, I think back about a lot of people that I worked with in West Africa, people living there. People from there are people that are just trying to make a difference in the world who are unseen.
You know, they're not necessarily on social media. They don't have [a] profile or platform, but when it comes to the blog and such, I mean, there were a few people that I look [up] to in my early days, like Gretchen Rubin, who I'm sure is an author most people [are] familiar with. She wrote The Happiness Project, among many other books.
So she was blogging for about a year or two before me in 2008. And I kind of looked to her among maybe two or three or three or four others. And I was like, “I like what she's doing. I like what they're doing. I want to create some kind of community sort of like that.” So I looked at that, and then these days, I mean, like I'm fortunate to be friends with Gretchen and lots of other people that I looked up to and have learned from, but also, in terms of inspiration, I would say a lot of it comes from my community itself.
And I try to have lots of conversations with people and discussions and when I'm able to travel, doing meetups and events. I was supposed to be doing a 40 city tour right now for the new book, and of course, I'm not doing that. I always enjoy different conversations and such. I kind of go away feeling like, oh, it's interesting, you know. Here are these folks in London that are all doing their own thing, but we had this shared conversation that kind of guides what I do next and such. So at a certain point in the journey, I started highlighting more of those stories. And I think for me, that's a big part of that inspiration or model.
Parul: Yeah, I love that. I love the idea of listening to your community and being on that journey with them. You write a little bit about expanding the pie—this abundant writer mentality. I actually found a blog post from just before you got your first book deal. And you're very excited, and you said, sure, I'm not getting rich at the moment, but I'm still travelling, right. And then you went on to say that even though you were in this very early stage, You would continue to expand the pie, this idea. It's not a zero-sum game. We can all grow together, which I'm getting from how you're talking about your community. That's how you still feel, and you also spoke about being professional, how it was very important for you to switch like Steven Pressfield talks about, you know, becoming pro. I'm curious over the last decade, what that means practically when you expand the pie, particularly when you don't have much and you start off. What does that look like in practical terms, and what are the core components of being professional as a writer?
Chris: I think those are two things that—I'm sure they're connected in some ways—but just to take them a bit separate, I think. Expanding the pie, It's an interesting phrase. I haven't thought about that in many years to think. That post was a long time ago, as you mentioned, but I like the concept of it's not a zero-sum game, as you said. And so if you don't have much of the pie, I mean, or, you know, whatever it is that you want to think of, you can still be helpful.
Like for me, a guiding value has always been like, there's gotta be something I can do today to help somebody. You know, it's not like I'm the saviour of the world, but there's something that I can do somewhere that is of use to someone. And I think everybody can have that mindset.
And so it could be highlighting other people's projects. It could be like doing whatever you can to get someone else to have attention or whatever it is. And so, I mean, when I started, I just tried to have kind of a mix. I was going to say balance, but I don't really love that word. It's more of a mix of here are some of the things that I'm doing. Here's a message that I'm trying to put forward and, you know, I want to grow my audience just like everybody else, but I also want to, you know, the very nature of my work about nonconformity is I want to look at people who are doing things differently and like, what can we learn from them? What can we take from them?
You know, I've been helped all along the way by all kinds of other authors and other people who have shared my work or been kind to like blurb a book or something. I also think we're just happier when we do that. I think we are intrinsically happier when we're a little bit less focused on ourselves and more about, like, what can we do to contribute to something?
And then the professional thing, I don't know, I guess for me being maybe—it's like some kind of self-discipline or something of like—I feel very fortunate to have this life, and I feel very fortunate even like, you know, ten years ago when I got that first book. I was very excited about that. And like, I didn't get paid a lot for that first book. I was thrilled to do it. I was thrilled. Anybody who's a writer here who’s had that experience, you probably relate. It was like, I remember when I got an agent and he pitched the book around and after like 12 rejections, you know, finally the 13th publisher … and he called to tell me that they wanted it.
And I was like, “Oh, that's amazing.” I didn't even think until later like to ask what were they offering? You know, it was like, that was the second secondary kind of thing. I feel very fortunate to be able to do what I do. And so, as part of that, it's like, well, since I am able to do this—like a friend of mine said to me a long time ago, if you're fortunate to find a way of life that works for you, first to understand how amazing that is, and second, like do everything you can to protect it. And so for me, protecting it as like, okay, well I get to do this. It's not that I have to do this. I get to do this. I get to write and do the podcast or whatever. So why would I not want to do everything I can to continue that and to support it however and such? So it's not drudgery, it's not a chore [or[ a task. It's very much like this is exciting, or this is meaningful. And so maybe not every part of it's exciting or meaningful, but together it is. And so, I'm going to try to stay on that path as much as I can.
Matt: That's great, Chris, and you mentioned the idea of discipline being part of being professional. And that was one of the notes that we had about you is that you have this history of discipline, whether it's 193 countries by the time I'm 35, or I think I heard you say you've done your side hustle school podcast over 1200 days in a row. I think you did working out for 365 days. So you're a very disciplined person, and I guess what we are curious about is, does this discipline come naturally to you? Is this kind of like an OCD tendency you have, or was there a moment where something shifted in you, and you became the professional? You became disciplined.
Chris: I mean, I was going to say, when you said disciplined, I almost thought as disciplinary is a compulsion, right? So maybe it's a little bit of both, and I think what I've noticed is that having a streak is really powerful. When I started the podcast, I was like, I feel like I'm late to the podcast world. Everybody's been doing a podcast. What can I do that's different. One of the thoughts was, okay, I'm not going to have guests. I'm going to make it really short. I'm just going to teach. And then the last thing was like, “I'm going to do it every day. I'm gonna do it every single day.” And I really liked that.
Like I latched onto that as soon as I thought about it. I remember talking with the publisher or the distributor of the podcast when we first set it up. And I was like, and I want to do it every day. And they were like, you know, “Wow.” That's a lot like five days a week.” That's a big commitment like five days or seven days a week, you know, like every day, right.
Like, oh, okay. I really liked that. And I think it's whether it's a podcast or anything else [like] writing, you know, people are writing a thousand words a day or maybe more. If you do it over time, it becomes harder not to do it. It would be harder to like stop the streak than it is to keep, you know. It might come to like at the end of the day, and you're tired from your day job or whatever else, but you're like, man, I've been doing this for 54 days in a row. I've got to find a way to move forward with it. So I think it's positive in that way. And as for whether I've always been like that, I think just over time, I began to kind of recognise the power of that. Maybe also to make the right choices on the front end or like, you obviously don't want to choose that for everything.
And that would just be a recipe for burnout or whatever, but if you're doing it around something that you are personally motivated to do and it connects to one of your long-term goals, then I think it's positive. At least for me, it's been positive and helpful. So it's not so much like a bragging point. It's not like, “Hey everybody, I did this thing.” The accountability is probably as much for myself as anything else because it's not like anybody's going to care if, like, oh, the podcast is like one day later or something. Nobody cares, right. But I would. It would bother me. Part of it is just like [it] keeps me going essentially.
Parul: Tim Grahl talks a lot about momentum for his podcast, and there are other writers. I think that's what strikes me about you is that you have the patience for this momentum to build whether you actually have the patience or you're sitting there thinking, why isn't anyone listening to me at first? I don't know. Yeah, I find that really inspiring. And that's something that Matt and I have been trying to keep a streak for the London Writers’ Salon and write every single morning. And a lot of the writers actually in this room have been showing up even when they don't want to.
Chris: Right. That's how it works. And I was going to say also for me, it would—the other secret about the podcast is it would be easier for me, or it's easier for me to do it seven days a week than it would be to do it like three to five days a week. Like if it was like Monday, Wednesday, Friday, it would be harder than every day because every day it has to happen, right. Whereas if it's on like a staggered schedule, it's like, oh, you just kind of get off the rhythm.
Matt: It's binary. You're doing it, or you're not. Yeah. I want to go back to this idea of, I'm not sure we framed it as such, but expanding the pie or another way is an abundance mindset versus a scarcity mindset. And this seems to be a theme that runs through a lot of your work and especially your newest book, The Money Tree, which is a diversion from your other books—all your other books. Your six books have been nonfiction. This one's fiction. It's a parable [that] talks about a character, Jake, taking agency for his life and career, and part of it [about] embracing an abundance mindset.
Could you tell us a little bit about just the premise of the book that you'd like us to know about it?
Chris: Yeah, it is a diversion, and publishers don't like diversions. Usually, publishers don't like anything. That's like if you're like, this is your lane, you should stay in your lane, you know, because that's what we know works, right. And especially if you want to do anything that's kind of like a hybrid model, which this is very much a hybrid as it is a fiction. It is a novel, but it's also—it's prescriptive fiction and that I'm trying to teach something, essentially. So it is a parable, as you said. Although I don't like the word parable just among writers here, because I feel like a lot of parable books are not that great.
And so I wanted to just kind of think a little bit apart from that. I used to be asked about the setup of the book and such. So this guy, Jake, is [a] millennial who has a decent job and he's a hard worker, but he also is experiencing a lot of financial pressure, like so many people in the states and the UK and all over the world are right now. For him, it comes first in the form of student loan debt, which is a huge problem in America and elsewhere. And that debt then starts to affect the rest of his life, his relationship, his day job, et cetera. And he has to kind of figure out what do I do? How do I get out of this? And he can't just work harder. He's already working pretty hard.
He can't just drive for Uber or something. That's not really gonna solve the problem. And so he ends up going to a group called The Third Way. Everybody at this group is trying to create a little income-generating project for themselves using this model of starting with the skill you already have and not going into debt and beginning quickly and such.
And so he kind of learned through that process. There's a bit of a hero's journey thing to it. And then he experiments with lots of different stuff. So I was excited about this book, but it was definitely an interesting thing to share with publishers because I had several publishers that said to my agent, “Wow. We really like Chris. We would love to do a book with Chris. Does he have a different book?” Oh yeah. Here's another book in my pocket. I actually had a second book that I was going to talk to you [right] after we pitched it, you know, like it doesn't quite work that way.
Parul: I guess, and also what's good about your approaches is you have a following, which means that they probably have to be a bit more leaning with you than a writer who had a smaller following. It gives you leverage.
Chris: Maybe. I think these things are kind of ephemeral, or it's like, what does it mean to have a following, you know? To have—supposedly you have people that are a number on this social network or such, does that mean they're going to buy books, you know? Some, maybe it does, maybe it doesn't. I mean, I try. I mean, obviously like when you're pitching the book, you want to be like, yes, you know, millions of people will buy it; therefore you should pay the most for it on the front end, et cetera. But you never really know, at least, I don't know. I don't take anything for granted. When somebody says they bought my book, I'm like, “Thank you. Like that's so cool. I hope you like it. Let me know what you think. I hope it makes some difference in your life.” I don't take anything for granted or try not to.
Matt: Let's talk a little bit about the book and also just the current state of affairs. So you had a what? A 30 city book tour planned, you know, you love travelling, you love meeting readers in person. How has this transition been for you? And do you find that you've been able to replicate kind of the impact and the connection that you've had in-person with online? Um, yes or no. And, or has anything surprised you about this. That maybe it's better or worse than you thought it would be?
Chris: Yeah. That's a good way to frame it. I think it's like, yes and no. It's both, in some ways, one of the things I thought of pretty early on. So the book came out April 7th, and we had the tour planned for January, February. We're working on it. And obviously like, as February goes on and like early March starts for like, hmm what's going to happen, you know? For like a week there, it's like, oh, you know, maybe it's like piecemeal. Maybe we can, like—there are some places we can go, and some places we can't and finally realise it's better to just not even try to do that.
And so after I made the decision to postpone, which I'm still thinking of it as postponement, obviously it depends on what happens in the world, but if it's possible to travel and do events in the states this fall, I will do that. But we'll see. At first, I was disappointed, and I mean, I still am a little bit disappointed about that because I liked that process and really enjoyed the in-person stuff. But I also kind of realised maybe I've been doing it that way because that's what I know how to do, you know? And that's comfortable to me; therefore, it's not necessarily the best thing, right. It's just like, oh, I do that because that's what I've done before. When I met you, Matt, in Milwaukee, you know, that was, I don't know how many years ago? Eight years or something? Probably.
Matt: Yeah.
Chris: I started by doing that a lot. It's like for that first book, I went to all 50 states, every province in Canada, 63 cities, and then for a $100 Startup, I went to a hundred cities around the world, and I loved that. I loved everything about it, but I also like—so now I fast forward.
That was great. No regrets, but am I supposed to be doing that for every book? You know, maybe not. Maybe it's actually more effective these days to talk to 72 writers in London or to people in Singapore or wherever they are through these kinds of virtual digital things. So it was a good way to kind of reframe and to say everybody needs to adapt. Am I adapting? What am I going to do differently about that? I think it's still possible to have very effective connections and community. And I think we're all seeing that in different ways. And I think this is a little bit of like a side note, but just the way that remote work is changing around the world.
I mean, I think if COVID-19 were not a thing tomorrow, like tomorrow, it completely goes away. The world of remote work has forever changed, regardless, because so many companies now are—a lot of their employees are not going to necessarily want to go back to the office like every single day, at least.
And they're going to say, “Well, this worked before, like you said, it wouldn't work, but now it did work.” But I think that's an interesting, interesting thing. This book, in particular, is the kind of book that will rise and fall based on what people think about it and what they say about it.
There's not much I can do to make some magic happen. It's going to work if people are moved by it and refer to it and talk about it. And if not, then it won't. So that's also interesting to kind of let go a little bit of [the] outcomes. I want to control the outcome, but I can't. So that's interesting.
Parul: No, that's a really interesting way of looking at it. A lot of the writers in the room and the ones who come to our Writers’ Hour talk about all the content that they want to create, whether it's a blog or a podcast or being more present on social media. You've put out a lot over the years, and so we had a question from Joe and myself. Uh, Joe is one of the writers who—
And we were looking at the idea that you have books, got multiple websites, you've got the podcast, got social media. How have you, and maybe do you now decide to allocate time across so many different areas because it can seem really overwhelming for someone who's new to it.
Chris: If you're new to it, and not just if you're new to it, but no matter what part of the journey you're on, you don't have to do all those things, and you might actually be more effective if you don't. You know, I might be more effective if I just did, you know, one or two things. For me, it's partly a reflection of my personality, and I like to start different projects. That's how I'm motivated. Some of my colleagues, you know, some other authors who are just very much like this is my lane, I'm going to stay in it.
And they actually can do very, very well with that and probably reach more people and have more book sales or whatever the metric is and such. So it's not necessarily a bad thing, but in terms of how I decide, it's not—that's also not really strategic. It's not like I had some plan of like, this is—okay, this is going to happen.
And then this, you know, step one, step two, step three. I think that's reflective of both like historical journeys in terms of ten years ago. I didn't know we were going to be having this conversation now. And I was going to look back and say, “Oh, then I did this and this and this.” I just did the things I was excited about, and whatever made sense next, I was like, this is the next piece I'm going to do this, and this is after that, then I'm going to start this event in Portland. And [when] I started that event, I didn't know it was going to be an annual event that goes on for ten years. I wanted to write a book, a second book, and then a third book. So even if we fast forward to now and say, “Okay, what's my workflow, or what's anybody's workflow this week?” It's like, I've got some things in place. I have a calendar, I have certain deadlines and such, but then I also have a room to move the building blocks around and do whatever I feel like, whatever seems, right. So it's not so much like a strategic plan.
Parul: Yeah, no, that makes sense. I think you're making some decisions, but as you're saying, you're responding to real-time events properly and building things that you want to get done. I'm curious about these different mediums and platforms. Do some generate more money than others? Do you keep track of that, or do some of that give you more of a headache than others? Therefore you pull back?
Chris: Yes, so in terms of the monetary stuff, the podcast has really surprised me, and the podcast is disproportionate in terms of the income it brings in. And I think that's partly because of that medium, basically, and that medium’s natural tying with advertising. And when I started, this is an interesting thing about podcast because I had never done any kind of corporate partnerships, you know, at all.
I never had any advertising in my blog. I was very, very wary of that kind of thing. And when I started the podcast, because I was working with a distributor and like this is their model. They have an advertising model. I was like, okay, well, this is how most podcasts work, and it seems like people understand it, so it's fine. I'll try it.
But even in the first six months, I was very, I don't know, I was very cautious about it and very soft in like pitching the ads. And I would have arguments with the distributor over various things they wanted me to say and such like, “Oh, this is too much”, you know? And then I just kinda noticed over time, like the podcast is really taking off, and nobody's complaining, like, not like—I get to the end of the year, and it was like, oh, 2 million downloads, and I might have got like two complaints about ads during the year. And I went on tour and then people actually would—I'm calling people for question and answer and somebody was, “I want to thank you so much for introducing me to the sponsor of your podcast, because…”, I'm like, “What?”, you know like I did not expect that at all.
Parul: That’s interesting. I didn't think that people would thank you for it. Wow.
Chris: Yeah. Well, I don't think most people are thinking podcasts is for ads, but I think most people understand that's kind of the model of how it works. They understand their costs. You listen to this, and you can fast forward if you want, you know, as long as it's not too annoying.
That's okay. So the point is that it is disproportionate in terms of revenue, for sure. And in terms of the books, I mean, so I have a back catalogue of six books now and a $100 Startup, you know, it continues to do very well. That's like the book that's done the best. A couple of the earlier ones will bring in like some amount of royalties, and then a couple of them, like nothing happens, you know. And I wish it were more distributed. Like every author, I think, wants there to be like, you write a book, and then this is like a long-term income stream. You write another book, and it just keeps building.
But I think it really is like a hit or miss kind of thing. And so the only thing you can do is take more hits or try, you know, like you take more chances. That quote about, like, to be luckier…I'd like to have more luck, take more chances, basically. So I think that's the only thing there. As for headaches, I don't know. I don't want to say that anything's—I mean, I'm sure there are headaches with all of it in some ways, but the joy of it or the joy or the reward or whatever it is greatly exceeds whatever headaches there are.
Parul: Makes sense. Is there anything you'd just—out of interest, is there anything you delegate? Is there one medium, like maybe on social media where you find yourself wanting to delegate more, or you do delegate?
Chris: Yeah, I'm really bad at delegation. I'm really bad at delegation, really about outsourcing. I have one assistant that works with me. I have a few contractors doing different things, but I've never been like, I'm going to build my team around. I'm going to like—I haven't really done a great job with that. So no. Hmm. I mean, I'm sure I could do it better if you're asking, like, what would I love to do more, I'm sure. But I just—that is a skill. That is something that people really have to develop. And I, again, I respect people who choose to be intentional about it because you will be able to like scale more that way. For better or worse, I've always tried to prioritise my own creativity over that, which is not to say you can't do both. I'm sure some people can, but I think most people tend to do one or the other.
Parul: Yeah. It's interesting. And I want to go back a little bit to this point, you’re talking about books and how some books have been good and made money and others, not so much, but money aside, I'm curious, is prestige important for publishing books? Do you do it for any other reason?
Chris: Sure. I have [an] ego, I mean, is there anybody that would say otherwise, you know, like I care about what people think of me. I would love to say otherwise. I'd be like, “No, I don't. I just, I do it for love. And like, I don't care if anybody ever reads the book”, but no, that's not really—that wouldn't be accurate. I wouldn't be honest with you.
Parul: I guess the question is more, do you find that having books gives you press like it's a good opener into different areas?
Chris: Yeah, I think so. I think there's a certain part of the population that is impressed with an author where—which is kind of odd, you know, in some ways, but you could do all kinds of other things in your life and then like—that are actually maybe let's say more significant perhaps than writing a book, but then when you write a book—
Parul: Like 40 million downloads for a podcast?
Chris: Most of them are just me just clicking…and like, my cat is like downloading. But like when I've had the first book, then it was almost like it was something respectable for my parents to talk about, you know. It's like, “Oh, Chris, he's got a book now.” Cause they didn't know what I did for a living before. They didn't understand the internet. I think that was like the parental prestige I don't know about for myself.
Matt: That's great. So, Chris, if we can kind of go into this—keep going down this money path for a bit. Obviously, asking for money, whether it's through a sale of a book or goods or services, which is a lot of your other work around side hustles and such, but also other forms of selling even if we're not selling something that doesn't cost money [like] sharing a blog post, asking people to read, how do you think about selling, whether it's monetary or otherwise? And has that shifted, or is there any kind of tools or tricks you've become better at sharing and selling your work?
Chris: It's interesting. Cause I mean, I write about marketing a fair amount, like I talk about it on the podcast. Obviously, that's okay—my books. But actually, I don't necessarily do a great job with it myself. Like I haven't built out a funnel system. I don't sell a lot of courses. I'm not trying to like, “Here's my lead generation tool to get you into my thing or whatever I know.” And again, that's not bad. I mean, that works. It's effective. And those tools can make people's lives better in some cases. But for me, I guess I just try to think about it as I'm putting a lot of work into something. Do I fundamentally believe it can help people or not? And if I do, then why wouldn't I want to do everything I can to share it. And also, I realised just the reality of like this career and the industry and such as like, you are kind of judged based on how the book sales are doing and like the opportunities that are available to you in the future are kind of dependent on what's happening now and such. It doesn't mean you can't break out of that. It doesn't mean you can't do something different and go on your own completely. But I do try to be cognizant of that.
So what I try to do is, you know, most of the time I'm not selling anything. Like most of the time, it's like for months or years go by without doing much. The podcast is free. The blog is free. Other stuff is free. I'm not really working on trying to build out that part of the online business. So I guess when the time comes to launch the book, I don't hesitate to push it a little bit because I mean like I said, I know that that's going to help people, and then I know it's going to help me as well.
So probably other people could answer that question better, I think. I'm sure you could ask some people who are much more successful and better at that than me.
Parul: That's still a really good—it's still an interesting approach that actually your jab, jab, hook is just a lot of jabs before the hook, but it seems like it's working for you. You're not so sure you're dismissive.
Chris: I mean, it seems like it's working, I guess. I mean, like what's the standard of working, you know. What's the—
Parul: For those of us who are a bit early on in having a readership or maybe particularly for writers who are starting from scratch, what would you suggest they might do to start out growing a readership and audience?
Matt: And maybe another way to think of it is if you were starting, you had no audience, you were starting from scratch today, what might you do?
Chris: Well, I'm curious what you guys think because I'm sure you talk about these things. I'm sure everybody has ideas about that. I also don't want to just say the same things that everybody else says, but I guess when I think about the question, and I'm like, “What would I do?” I'm not sure it would be any different than what I did ten years ago. Maybe the mediums have changed, or maybe the tactic has changed or something, but what I did, you know, I guess more than ten years ago now—11 or 12 years ago, it was like, okay, I'm starting this thing. I'm starting a blog. It's called The Art of Non-Conformity.
And it was very vague, very generic at the beginning or like general. No, not generic, but general. Part of that was to accommodate my own personality like my ADD personality. I was like, I don't want to get—I don't want to start something and get tired of it. So like, I've started a lot of projects and then stopped them because that's just how it works. And I don't actually want to really invest in this one and try to do something with it. So let's make it really broad. And I just went to everybody that I knew, which was not a lot of people. This is like pre-social media for the most part. I mean, Twitter had been out like a year, obviously Facebook and such.
I didn't even have a Facebook account, but I went to people I knew, like people I had gone to university with. I wrote to my friends, “I'm starting this blog, you know, will you come and check it out? And if you like it, please subscribe. And if you know somebody that might be good for, will you share it?”
And it was like five people in the beginning. And I started writing and like focusing on content and then…I focus on content, but not just that. I also focus on content, and I also started reaching out to other people that I respected, you know. I mentioned Gretchen, I wrote to Gretchen, I wrote to Seth Godin. I wrote to anybody else who was an author that I was reading or respected at the time just to say, “Hey, here's this thing that I started.” And I never had a viral moment. I never had like a “Here's like Chris Guillebeau, his debut on it.” It was one by one. I had this perspective of like anybody who joins my email list, that person has chosen to give me like their most valuable asset, which is their time and their attention.
As much as possible, I want to build individual relationships with those people, which is, you know, people always say like, “Well, does that scale?” It's like, well, that's a problem to deal with at some points, right? But you can do that for a long time. And so I think it was the first—for the first 10,000 people that joined over the course of, I don't know, two years or something, maybe a year and a half, like I wrote to each one of those people. Not just like an autoresponder, but I wrote an actual email to those people, and said, “Hey Matt, thanks so much for joining”, you know, “Hope you like it. Let me know what you're up to.” You know, enough of those people write back over to like, “Is this a fake? Is this a real person?” Yeah. It was me, you know, you're actually building some kind of relationship. I would do something like that. I mean, maybe that, like I said, maybe the tool has changed. It was social media.
I would go on, and I always start commenting on everybody's posts, not in like a spammy way, but more just like I'm contributing way or something. I would build it one by one.
Matt: Yeah. And me being on the other side of that, I think every time I've emailed you, whether it was two weeks ago about this or eight years ago, you were always responding. I would probably echo that in saying that's—yeah, from a reader's perspective, that's probably one thing that's kept people on your side and along the journey is that generosity.
A little bit about blogging: so obviously blogging, the state of blogging has changed quite a bit. Where do you think blogs sit right now? We have a lot of people—I mean, I have a blog. I know the idea of being a blogger is kind of now newsletters of the new blogging. And do you have a sense that—
Chris: Yeah, I mean, like, I'd be curious what your take is. I actually still like blogging a lot. I actually think I don't blog enough. That's something I would like to do more of cause I really do enjoy that medium. I kind of find that my time is increasingly filled up with other stuff, which obviously I have put—you know, it's like, nobody has imposed this upon me.
I'm the one who's filled my schedule, but I don't know if I have like a take—like here's how the blogging industry is. There will always be room for people to share messages, to share your content. Like, if you have a story, if you have something, maybe in some ways, you know, other mediums or other formats are seen as more prescient or more like—that's not quite the word—but more in the forefront now.
But I don't know that I would hesitate on starting a blog like if that was the medium that I most connected with. And like, if I was starting over, I might still start a blog of some kind. I mean, everything has a pro and a con, right? Everything has like a, yes, you know, newsletters are big, but now, I mean, I have a lot of people on my newsletter who never read my newsletter because they don't get it.
Gmail filters it out or whatever, just like on Facebook, so many X number of people follow my page or whatever. But if I make a post, I can go and see it is a tiny percentage of actually seeing it because the algorithm doesn't serve it to them. There are always limitations to each medium. It looks like strengths and limitations, you know?
Parul: First of all, I agree with you. I think that for different people, different mediums back. And for some people, [a] blog may be the way forward; it might be preferable to a podcast. Maybe they don't like the sound of their voice, or they don't like the public nature of it, but whatever you are, whatever one does do on content, and maybe particularly for you…what about difficult subjects?
How do you talk about difficult subjects? Because you can work your shit out on the page, or you can publicly share it. Where does the line come in?
Chris: I think it's a personal choice. I don't think it's a business decision. I think it's a personal choice. It's like, what are you comfortable with sharing? Again, if you have some experience that might be helpful to some people and you are, you know, willing and comfortable to share it, then maybe you should because there's probably somebody out there that is not expecting it and they're going through something similar, and they're going to relate to it. I mean, I started writing a little bit about mental health a few years ago, and some personal experiences that I had and I got, you know, it's not like I get like a ton of fan mail over it, but I get like some really meaningful things over time.
Like you hear some really deep connections and such with people. So I think my rule is you don't have to. You certainly don't have to share anything vulnerable or personal that you don't want to, but if you are going to share, then I think whatever it is you choose to share—that I think you have to be pretty open and transparent about it.
It's kind of weird to share halfway. I think, sometimes, people try to split a difference and like, whatever you're going to talk about, let's talk about it or let's not, you know. And it's okay. It's perfectly okay to say, like, it's not, I'm not here to talk about whatever the subject is or what—I think it's not something that you have to say.
What is the best career choice for me here? It's more just like, what do I feel comfortable with and how will I feel? I mean, I always think like regret is a good thing to think about. Regret of like, if you fast forward a year or something, and you've got an idea to write a book, or you're going through something, and it's like, should I share this or not, or should I start that podcast or that YouTube channel or whatever. And you fast forward a year in your head and say, “How am I going to feel if I don't do that?” “If you're like, eh, okay. I don't—”, you know, then that's fine. But if you're like, “You know what, I probably wish I would have tried that”, then that's your answer, right?
That's your answer. It’s like, make your decisions based on future regret. And so, if you can have that kind of perspective, that helps a lot for me, at least.
Parul: Yeah. Thank you for sharing that. That's interesting.
Matt: Thank you so much, Chris. So Chris’ book is on sale, pretty sure everywhere. We're so happy, and this has been such a privilege to sit here and chat with you. We really appreciate it. Is there anything you'd like to leave us with? Any parting wisdom on our journey or maybe a kick in the butt?
Chris: I don't think I have any parting words like that. This has been a wonderful conversation. And thank you for the wonderful questions. Hopefully, we'll get a chance to actually hang out in London at some point. And I'm very grateful for this time. Thank you.
Parul: Thank you so much. There are some great links. We'll be sharing. Chris was recently interviewed by Ryan Holiday on his podcast, and there are some other great interviews that we've heard that we'll share with you.
Matt: Any other asks of us other than check out the book?
Chris: No, no, no. Just go do your—go do your thing. Everybody's here because they want to invest in themselves, right? That's the thing, you know, I always think it's, like, why are you here and not watching Netflix or something? And it's probably because you—like, I actually believe in this work that I'm doing.
So go do your work, you know, do your work and share it. And I look forward to being on the other side and asking you all these questions sometime.
Parul: Thank you.
Matt: Beautiful. Thank you so much, Chris.
Parul: Thank you for tuning into the London Writers’ Salon podcast. If you'd like to join these weekly interviews live for the chance to ask our guest writers your burning questions. Well, you can become a member at londonwriterssalon.com forward slash pound membership. You'll get access to our library of salon interviews and workshops, our private online community, where you'll find world-class resources on the craft of writing and find creative friends.
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