Brendan Leonard is a 45-year-old writer, illustrator, ultramarathon runner, new father, and former dirtbag who makes a living by sharing his love for the outdoors. (semi-rad.com / @semi_rad)
After spending many years focused on running, climbing, skiing, cycling, hiking, and traveling, Brendan Leonard has settled down in Montana with his wife and young son. He explains the original meaning of the word “dirtbag,” what his own dirtbag phase looked like, and how he cobbled together a multifaceted creative career in which he essentially gets paid to “go out, do interesting things, come back, and write about them.”
We discuss the nuances of making money from your hobbies, why Brendan tells stories of everyday adventure rather than epic expeditions, and his favorite way to measure his impact. He explains how having a child changed his life in deeply meaningful and entirely predictable ways, where exactly his money comes from, and how he and his wife (also a freelancer) managed to buy a house in a cute university town in Montana without family assistance.
Brendan concludes by defining the core ethos of dirtbagging: enjoying the freedom to wake up each day and decide what you’re going to do with your day—and by extension, your life.
I highly recommend Brendan’s most recent book, “Ultrasomething,” and his “Friday Inspiration” newsletter.
Full transcript: dirtbagrich.com/brendan
Recorded in October 2024.
AI Notes
This is an AI-generated summary and transcript. Typos and mistakes exist!
Summary
This is a transcript of an interview with Brandon Leonard, who discusses his experiences as a ‘dirtbag’ – someone who lives a minimalist lifestyle focused on outdoor pursuits like rock climbing and trail running. Brandon shares details about his dirtbag phase from 2004 to 2017, living out of a van and prioritizing adventures over material comforts. He talks about transitioning to a more conventional life with a house, wife, and child, but still maintaining a “semi-rad” lifestyle through freelance writing, illustration, and other creative projects related to the outdoor world. Brandon reflects on finding purpose, balancing creativity with parenting, and the freedom his unconventional career path provides. Key topics include his income sources, sacrifices made, and the joys of an adventurous yet grounded life.
Chapters
00:00:08 Introduction to Brendan Leonard and the concept of ‘dirtbag’
Brendan Leonard is introduced as the guest, and the term ‘dirtbag’ is explained as referring to people who lived minimally in pursuit of outdoor activities like rock climbing in the 1960s. Brendan shares his personal experience of living a dirtbag lifestyle from 2004 to around 2017, residing in vehicles and prioritizing outdoor adventures over material comforts.
00:07:55 Brendan’s creative career and income sources
Brendan discusses his journey as a freelance writer, starting a blog that became a brand called ‘Semi-Rad’. He now earns income from various sources, including Patreon, merchandise sales, traditionally published books, freelance work, and past sponsorships. He provides a breakdown of his income sources from a particular year, highlighting the diversity of his revenue streams.
00:15:48 Balancing outdoor pursuits and family life
Brendan reflects on how having a child has shifted his priorities and perspective. While he previously focused on outdoor adventures and creative work, he now finds immense joy in simple moments with his son. He discusses the challenges of balancing his passions with family responsibilities and the trade-offs he has made to accommodate his new role as a father.
00:29:17 Finding purpose and meaning in his work
Brendan shares his thoughts on the purpose and meaning he derives from his work. He finds fulfillment in creating content that resonates with his audience and facilitates connections between people. He values the freedom his lifestyle affords him, allowing him to pursue his interests while also being present for his family.
00:56:14 Financial considerations and lifestyle choices
Brendan discusses the financial aspects of his lifestyle, including the support he received from his parents early on and the strategic use of book advances to purchase property. He emphasizes living modestly, avoiding excessive spending on material possessions, and finding ways to incorporate travel into his work. He highlights the trade-offs and sacrifices he has made to maintain his desired lifestyle.
Transcript
Blake Boles 00:00
Brendan Leonard, welcome to Dirtbag Rich.
Brendan Leonard 00:03
Thanks for having me, Blake.
Blake Boles 00:05
What is a dirtbag?
Brendan Leonard 00:08
Well, historically, I think that the origin of the term is people who lived in the Yosemite Valley in the 60s who chose to not participate in capitalism very much so that they could climb rocks like El Capitan. So do big wall climbing. So lived with very few creature comforts in pursuit of a bigger outdoor goal, I guess. That’d be my best. That’s my best, most factual answer. Nowadays, I feel like it applies to anyone who tries to capture a little bit of that ethos.
Brendan Leonard 00:46
But I think a lot of us had not a safety net, but a lot of people are just like, yeah, I live in a van. And it’s not like you live in a van. You could go and retreat to your parents’ basement if you needed to or whatever for the most part. That was the case with me. So I’m not…
Blake Boles 01:08
Tell me about when you were a dirtbag or your most dirtbag phase.
Brendan Leonard 01:13
Yeah, I mean, I was like, legitimately not making a lot of money from, boy, 2004 to… You know, I’m not making a lot of money now. I don’t know what I’m talking about, but like…
Blake Boles 01:27
more now. Yeah, yeah.
Brendan Leonard 01:29
But 2004 to 2016, probably, 2017, I had a car I paid $4,000 for, spent every moment outside of work either trying to make a little bit of money as a writer or go rock climbing or doing things in the outdoors.
Brendan Leonard 01:49
And then, I think, aesthetically, my life was the most dirtbag-ish from 2011 to 2014. Just shy of three years that I spent living in a vehicle. So a Subaru Outback Impreza, which is a small Subaru that I could sleep in the back of barely.
Brendan Leonard 02:12
And then, I upgraded to a $6,500 Chevy Astrovan, which that was in 2012, early 2012, and lived out of that for a little over two years. And that was not a nice van. I don’t know if, I don’t know if, I remember a friend saying to me that the Subaru all -wheel drive and Chevy Astrovan all-wheel drive are completely different things.
Brendan Leonard 02:44
But that was my, that was for lack of a better, it was my house for those years. I had a storage unit that I kept all of my worldly possessions in and then the van, and I would just kind of tool around the west and return to my storage unit in Denver periodically to switch out winter things for summer things or if I needed a piece of gear that was in there or whatever.
Brendan Leonard 03:07
But yeah, so I lived out of the van, worked remotely and did some stuff in the outdoors and slept in a lot of roadside pull -offs, the occasional national park parking lot, national forest land, BLM land, and then got a hotel every 10 or 12 days to actually take a shower or I would pop by a friend’s house and use their shower if possible.
Brendan Leonard 03:37
But yeah, it was like, I didn’t have very much money, but I was kind of like pretend poor. I was like, a friend of mine always said, just because you don’t use it doesn’t mean the net’s not there. And were I really of different means and if I was really down to my last dollar, I would probably, that would be a much less comfortable way to pursue it.
Brendan Leonard 03:59
It was just like I was doing it because I could and didn’t have kids, a dog, a mortgage, anybody depending on me besides myself, parents were both doing okay, everything. So it was easy. And I think you at the time I was like, I’m a dirtbag, but you’re kind of like, you’re not saying all the privileges you have even though they might not be that big.
Brendan Leonard 04:29
It’s not like I had a trust fund I was living off of or really any money, but you can live out of a van and live freelance paycheck to freelance paycheck knowing that your last dollar is probably not your last option, I guess.
Brendan Leonard 04:49
Sorry, that was a pretty long answer.
Blake Boles 04:51
That’s great. You and I met summer 2022 when i was cycling through montana and again uh a year later and you have a pretty sweet house at this point you i got to hang out with you in the backyard
Brendan Leonard 05:06
Wow, do you think so? It’s like, I don’t think you came inside, man. It’s all right. Anyway, sorry, disaster. We have a house, but it’s like, definitely not. I would not have called it a nice house when we walked in.
Blake Boles 05:18
You were building a really nice looking shed in the backyard and I hear that’s finished now.
Brendan Leonard 05:21
That is literally the nicest room in the entire house, is the garden shed I renovated for my wife. But, yeah. I know.
Blake Boles 05:29
So have a house, you’re married, you have a son, do you still consider yourself a dirtbag in some way?
Brendan Leonard 05:39
Not, well, boy, that’s a tough question. I don’t think so. Like, A, what I was doing at the time, I would have called myself a dirt bag was pretty far from the original dirt bags. Um, you know, it was like, I was doing, I was spending a lot of time working on a laptop, you know?
Brendan Leonard 05:57
Um, and I don’t even think, you know, my wife lived with me while we were, we were dating at the time. So she’s just a girlfriend, but she lived with me. She was also a writer while we were. So we were spending, I would say we were spending over half of our time trying to find wifi or, you know, drum up freelance work or do the freelance work itself.
Brendan Leonard 06:18
Um, even though it was like not high paying gigs, and sometimes we actually lost money on the things we called work. Uh, but, um, they led to other things or whatever, but I, you know, I have this, I don’t think that like those early rock climbers like Yvonne Chouinard and Warren Harding, I would have a hard time explaining to them like how much I sit on a laptop and worked, uh, you know, um, whatever, despite what Instagram may have said. Um, but yeah, now I don’t know. I think like sometimes I think I like rejected a lot of, um, the things I was probably taught or the society I grew up in was like valued, I guess.
Brendan Leonard 07:01
Um, like I was like, yeah, I’m not going to be this sellout who gets a house and moves to the suburbs and has a family and blah, blah, blah. And becomes really uninteresting. And now I’m like 45 and I’m like, Oh, and I did all that stuff.
Brendan Leonard 07:13
I guess that’s right. So I think maybe I just succeeded in pushing it off later or in life, if that makes sense. Yeah.
Blake Boles 07:20
You do have a very interesting life though, and you haven’t just conformed to all the norms, even if you’re playing house. For sure. For people who don’t know you, can you just quickly summarize what you’re putting out into the world and how you’re making a living?
Brendan Leonard 07:35
Oh, I really wish I could, man. That would be ultimate challenge. I think that’s part of the problem behind my business plan. Uh, but yeah. Um, so I, you know, I started, um, my career as a freelance writer and, um, you know, trying to write for outdoor adventure publications and, um, was getting a lot of rejections.
Brendan Leonard 07:55
So I started my own blog, which when blogs were a thing in 2011 and that for, you know, to do to no real planning or brand vision on my end became what it, what you would probably call a brand. So it’s the website is semi rad .com.
Brendan Leonard 08:12
And I, you know, bought, or I got the, uh, the social media handles, um, semi rad. So that’s kind of just become what I do. And so it’s at this point, or over the past, let’s say 13 years, it’s been a mix of writing, illustration, filmmaking, um, for clients and for just YouTube, um, you know, some sponsorships, some book, some books I’ve written and gotten traditionally published and books I’ve written and self published.
Brendan Leonard 08:43
And, um, what else is in there? A little bit of photography. I’ve gotten paid for photos before. Um, so that’s, that’s kind of what I do. And like every week is just like trying to figure out which project to push forward a little bit.
Brendan Leonard 08:58
I write six, um, newsletter posts a month, roughly. So, um, that’s the most regular thing I do a little bit of illustration work for a couple of brands in the, uh, trail running, um, market scene, whatever.
Brendan Leonard 09:15
Um, and yeah, I’m just figuring it out on a year to year basis and every year the pie chart of what, how I make a living is different. Um, so that’s, that’s kind of what I do. Um, and it’s, you’re right.
Brendan Leonard 09:27
I have avoided getting, having a real job since 2012. I think that’s the last time I had a regular, a real regular paycheck with benefits. What was that? Um, I was, I, a friend of mine got me a job working writing, uh, copywriting for IBM, actually.
Brendan Leonard 09:46
IBM. Wow. Yeah. Didn’t, didn’t get me the job. Got me the introduction and was like, okay, you know, if you’ve improved these guys, you can do this. I think, you know, they, if they’re looking for people and it was like, that was 2000, 2011, I got that right.
Brendan Leonard 10:03
2011, I think. Yeah. And, uh, it was, um, yeah, I think I was making $30 an hour had, um, for your American audience, full health care benefits. I had vision inch dead dental insurance, which is like, I thought was kind of unheard of.
Brendan Leonard 10:20
And, um, it was fine. The work was, the work was fine. Um, but it was like, not really my jam in a lot of ways. And I was kind of doing that, you know, for my, I think I had to have 32 hours a week to keep my insurance.
Brendan Leonard 10:34
And then the rest of the time I was trying to drum up more outdoor adventure writing gigs. Um, and eventually after a year, year and a half at IBM, roughly, I was able to say, okay, I think I have enough regular work, uh, in the adventure space that I can pull the plug here and just go out of my own.
Brendan Leonard 10:53
And, um, it was like, I think I had like maybe $2 ,000 a month of guaranteed income, like before taxes, uh, that I was like, okay, I can, I’ll make it go with this and see what happens. Um, so, um, that was my, that was my last job.
Brendan Leonard 11:08
And I was like, I got a hundred dollar a month health insurance policy for, um, what do you call it? Emergencies basically. It was like, okay, I’m going for it. Um, and that’s, that’s, it’s been that way ever since I’ve better health insurance now. Um, but like, yeah.
Blake Boles 11:26
When you were in more of your dirtbag phase, what did you spend your time on? You mentioned a few things, but a lot of your writing has evolved to be about running and ultra running. What else is there? What do you do with all the time you’ve created for yourself?
Brendan Leonard 11:48
Wow, when you put it that way, I’m like, I don’t know that I have any more time. And nowadays, but I guess it’s just starting out, I think the thing that really grabbed me was rock climbing. And I started doing that in 2006.
Brendan Leonard 12:05
Yeah. And that was like the thing I did for like seven years. Like if I would do, I would go on backpacking trips, I would do, you know, whatever, do some mountaineering or just mountain climbing stuff.
Brendan Leonard 12:18
But I really wanted to rock climb mostly. And that was where that was all my stories, you know, went around that. And eventually, you know, was able to write for climbing magazine, had a regular column there for a year or two.
Brendan Leonard 12:34
And never surprisingly, never got that good at rock climbing. I just like to be out in the mountains and, you know, climb. And I think nowadays, I think really good climbers are more gymnasts than like the sort of mountaineers that I, you know, worshiped and like kind of wanted my adventures to be like I would rather walk 10 miles into something that would have no one else on it.
Brendan Leonard 13:00
And I think a lot of rock climbing nowadays is a much shorter walk to a like much shorter, harder routes that are very gymnastically difficult compared to I just wanted to like tie out a rope and kind of go up mountains for lack of a better description.
Brendan Leonard 13:16
But yeah, nowadays running is the thing I have time for. And it also is the place where I actually not really clear my head, but organize my head a little bit or just think about nothing for a couple hours and let things just kind of flow.
Brendan Leonard 13:31
And then that’s where I come up with ideas for creative projects, you know, sometimes. And we’ll have to stop on a trail and type in a note into my phone or most recently, like actually did some voice notes for the first time that were semi -coherent, if I may pat myself on the back, you know, so you’re like jogging and you’re like, and then this thing is blah, blah, blah.
Brendan Leonard 13:52
And like, and then, you know, sort of transcribed it for myself when I got home. It actually came out okay. But yeah, like, I’ve kind of just done a little bit of everything in the outdoor space besides white water kayaking.
Brendan Leonard 14:05
I’m not that’s terrifying, but like a little bit of back country skiing, a little bit of backpacking, a little bit of mountaineering, a little bit of rock climbing, ultra running, lots of hiking. Bicycle touring.
Brendan Leonard 14:17
Bike touring. Yep. A tiny bit of mountain biking, but I think I’m too old for it now. Not really, not really that interested. Bike packing is like way more interesting to me at this point. But yeah, so just kind of like all around with what are some ways to be outside and it’s all travel really, you know, even a rock climber who’s climbing a 10 foot tall boulder problem is travel, right?
Brendan Leonard 14:42
You’re traveling over this small surface as opposed to this larger surface where I maybe bicycle across America or whatever, you know. Can you dwell on that?
Blake Boles 14:52
of travel, it’s all travel. I read that as it’s all movement. Yeah. And what is it, just for you, yourself, where does this this passion or obsession with movement come from? Where do you think, what was the genesis of this for you?
Brendan Leonard 15:10
Um, yeah, like maybe like movement and exploration in a little in the small sense, not like I’m finding, uh, new Like things that I do are not new to the human race, but they’re new to me, you know um so I guess uh when I I Actually moved to montana the first time and when I was 23 to go to graduate school to get a masters in journalism and um You know, I thought at that time I was like, oh the ideal thing would be to like write for rolling stone magazine write about music or whatever and um I took a magazine writing class and the requirement for grad students was that you had to get published,
Brendan Leonard 15:48
uh before you could pass the class and I thought That is insane. Like how am I ever going to convince rolling stone to like publish my story and A friend of mine said why don’t you write something for idaho magazine, which is like this small magazine that she’s like They could take anything they’d pay 40 bucks and it was like I mean that’s a that’s the pay is terrible but like they take anything I need to get published and um So I you know kind of approached them with a story about this little um 36 hour road trip my buddy and I did in idaho the previous summer and Just a few,
Brendan Leonard 16:23
you know, we climbed a mountain. We went to this national monument We visited hemmingway’s grave and I think that was it and they were like, yeah, we’ll take that sure And uh, that was my first publication and I think that um That showed me I could do the things that I wanted to do anyway and Also make a living from them in some some way obviously you like If you’re writing articles for 40 a piece even in 2004 You need to write many many many articles at that point To make a living but it was like oh I can get paid for this.
Brendan Leonard 16:59
So it became this sort of uh Model of go out do interesting things come back write about it or tell about it, you know um and that’s just kind of what i’ve been doing the entire time and um You know you can just tell people the nuts and bolts of what you’re doing or what you did and There’s all sorts of ways to do that And a lot of people who are probably way more financially successful.
Brendan Leonard 17:27
Just do that, you know, like Talk about popular things like here’s how to backpack, uh in the grand canyon or here’s how to Climb mount rainier. Here’s the gear you need. Here’s how long it takes, you know, and i’ve never done that I’m always like trying to find some other sort of lesson or you know, funny thing or some sort of scene so it um, it’s just kind of this font of material and um It also might be because i’m lazy and I don’t like to do reporting like in the newspaper sense where I talk to a bunch of people then form a story around it and And put it together and i’m like,
Brendan Leonard 17:59
ah, i’ll just go do the thing and Do stuff that’s fun. And then I can yeah, I know so it’s like it’s like sloth basically, but also You know You’re not you’re not obviously that lazy if you’re going out and like running 50 miles to like try to figure out what you know Try to figure out a story around it.
Brendan Leonard 18:16
But you know, like We make stories out of anything and like I grew up around Storytellers, you know who could just like You know some of the funniest things that ever happened to people were things that happened when they were on their way to work Or at the supermarket or just like whatever, you know And it was like if you can tell a story about that surely I can go climb to the top of mount shasta and ski down and try to figure out something to say about it, you know, um Or whatever it is you’re trying to do. So Yeah
Blake Boles 18:47
You produced, you’ve produced a lot of great stuff out there. I want to talk about two things in particular. One is the short film, I believe for REI called how to run 100 miles. And I showed that to a group of my teenage students recently as an example of what people do when they move up Maslow’s hierarchy of needs.
Blake Boles 19:10
When your basic needs for shelter and safety are fulfilled, respect, and then you get up into that narrow peak of self actualization. I mean, this is where a lot of modernity is biggest questions and problems come from.
Blake Boles 19:31
And your movie, it’s like humble and touching, but also you’re not lazy. You know, you are not sloth like Brendan, you and your friend were out there. I mean, the training runs to do a hundred mile ultra marathon can be 20 or 30 miles long, right? You can be doing a marathon as a training run.
Brendan Leonard 19:52
Well, with 100, you want to do more like 50 or 60 for the longest training run, which we did. I think we did something like 52 or 50. I don’t know. As a training man. Yeah. Yeah. And like, I mean, I always have to clarify.
Brendan Leonard 20:07
You’re not like an ultra marathon. You’re not running the entire time. Usually like the general population is not, you’re hiking the uphills and running the rest of it. And so, so it’s that it doesn’t, it’s not like just somebody who thinks of running.
Brendan Leonard 20:19
It’s like the New York city marathon. Yeah. You’re running almost all of that probably, but you know, ultra marathon, you’re not. So, um, but yeah, no, like Maslow’s hierarchy of needs, you get to the top and you’re like, Oh, I’ve taken care of shelter and safety and okay, I’m just gonna just like laugh in the face of all that stuff and you know, disregard my shelter and my safety and then go do this thing.
Brendan Leonard 20:38
And hopefully it translates into meaning. Um, so, um, I always think of those ultra marathons and trail running in general as being very safe compared to rock climbing. So I like, it’s all the pain and suffering of mountaineering without the fear of death constantly.
Blake Boles 20:57
So you also did a wonderful job of describing this in your book, Ultra Something, and I just wanted to use those two as entry points into the question of like, like, what is your obsession? I think a lot of people look at someone who runs 100 miles or look at someone who leads a dirtbag climbing life and says kind of, what’s their problem?
Blake Boles 21:22
And you can flip that around and say, what’s the obsession? What’s the fascination? What’s the, you’ve been doing this for such a long time now. This is not just a phase in your life. So what do you think is it that keeps tugging at you and makes you want to do more and more in the outdoors?
Brendan Leonard 21:39
Oh boy. Yeah, I mean, part of it’s just like, that’s what people or that’s where I can make a living, I guess, at this point, you know, I’m not trying to like, I’m trying a little bit more of like trying to share whatever I think is experience or knowledge in the creative world.
Brendan Leonard 22:02
But I don’t think I am a very prominent voice in that. And there’s a lot of people doing that. And the sort of the niche I’ve carved out for myself, you know, it doesn’t it sort of requires me to go out and do things in some way, even if it’s just like aching with my kid, you know.
Brendan Leonard 22:22
So largely, it’s like, that’s where I know how to make a living. And that’s where my contacts are. And that’s what my sort of quote unquote audience, you know, thinks of me as. So if I were to like go deep into woodworking, I think I would probably lose a lot of my income, you know, if I was going to be like, hey, turn flipping things around this year, everybody, I’m going to learn how to, you know, do like really artistic woodworking. And I’m going to tell all about that journey. And that’s going to be my writing career from now. And I think I don’t know that more than 10% of my current readership would hang out for that.
Brendan Leonard 22:58
But who knows? So part of it’s just like being scared of like not I’ve dipped into it like a tiny bit, like other things. And like sometimes but generally always comes back to like that sort of idea of adventure in the absolute broadest sense where like, you know, having a child is an adventure, you know, or just doing anything, you’re not sure if the result is an adventure, which is kind of every day for a lot of us, you know. So I don’t know, I like it’s, I don’t know if it’s an obsession or just like a rut maybe, but I like beating the rut, it doesn’t bother me.
Blake Boles 23:43
Well, it sounds like you’re describing audience capture, like this is now built into your economic reality. But clearly, there’s some sort of transition or gradient here because you started writing about this because you loved doing these activities.
Blake Boles 24:01
And I assume that you love being able to make money from doing something fun and meaningful. And you’ve built this sort of small online empire out of that. Can you chart the transition of your relationship towards your work and making money from doing something you love?
Blake Boles 24:25
Because the answer you just gave me actually surprised me a little bit. I’m wondering, do you still feel this pull, this tug? If you didn’t have to do it for money anymore, if you had some windfall money dropped into your account and that’s it, you can just spend your time as you like. I mean, would you stop doing things in the outdoors?
Brendan Leonard 24:52
Um, no. Like, boy, yeah, that would be, yeah. No, it, like, it, um, all these sorts of things really, um, are, I believe, good for me in so many different ways, you know? Like, I commented to a friend that I don’t actually run that much.
Brendan Leonard 25:13
I only run about 30 miles a week, which is not very much for someone who does, you know, ultra marathon distances, uh, as far as, a few races a year, like this year, I’ll probably only do one race. But, uh, and he was like, no, that’s actually still a lot of running.
Brendan Leonard 25:29
And I was like, yeah, you’re right. I guess it is. Um, just considering, like, people who are like, most people just go to, go to the gym, I think. And they’re like, you know, I, however many hours a week they work out at the gym, it’s like, okay, that’s what I need to do to like stay fit and comfortable and like, you know, at the, whatever, you know, weight level I want to be or aesthetic, aesthetically, how I want to look. And I’m like, yeah, like running 30 miles a week is kind of ridiculous actually. Um, but it’s good for me. I get, you know, like that’s, that keeps me moving. It keeps my heart rate low.
Brendan Leonard 26:02
It keeps my arteries clear. I hope, um, as far as, as far as all tests have proven to this point. Um, and it’s like, now it’s become a place for me to think in the outdoors and like get my thinking done because the rest of my existence, I’m very close to a lot of distractions.
Brendan Leonard 26:20
And, um, so yeah, I don’t know. Like it’s definitely not an obsession. It’s definitely not super, um, I don’t feel I’m not like, uh, let’s see, it’s not like this obligation at this point, but it is like, this is where I gotta go to like find stories.
Brendan Leonard 26:40
Sometimes I worry about like, I love, I really enjoy doing hard things in so many different ways. Like writing a book is extremely difficult. Um, you know, getting a two year old to put their shoes on is also extremely difficult.
Brendan Leonard 26:53
I don’t know if I like that that much, actually not thinking about it, but, uh, but like running, you know, running long distances or climbing a mountain is extremely difficult. And I enjoy doing difficult things.
Brendan Leonard 27:03
Um, I think to a point, but sometimes I wonder like if I just keep doing the same difficult things, same types of difficult things, am I really growing as a person to, you know, like, yeah, okay. You ran, you know, 31 miles of this race this year.
Brendan Leonard 27:18
If you do that again next year, is that like progress or are you just doing the same thing over and over? But I don’t know. Um, I feel like I’m just wandering around your question and not really answering it.
Blake Boles 27:31
maybe we’ll find our way back to it. Let’s talk about purpose. Do you feel like the work that you’ve been doing, the writing videos, interviewing, the workshops, you do writing workshops also, do you feel like this is contributing something to the world, something meaningful? Do you derive meaning from your work or does it come from other places?
Brendan Leonard 27:57
Yeah, I mean like the the absolute best metric I have for that and this is like something you can only As far as I know you can only access through like instagram is there’s a you can see how many people shared your posts Not like um Like they literally hit this button that says share and messaged it to a friend or Or someone and I assume based on what my work is about.
Brendan Leonard 28:24
I assume it’s a positive interaction that they’re having um, or Maybe there’s maybe somebody’s hate following me and they’re like look at look at this jerk and what he just drew or wrote or whatever um, but sometimes I look at that and like it gets you know, there’s a few dozen or a few hundred or sometimes even like a few thousand shares and I don’t see who’s sharing it with people or You know What they’re saying to each other about it but I assume it’s this thing where somebody’s like Jeff this post made me think of you Or our friendship because we talk about that We talked about this three weeks ago or this reminds me of this thing we did a few years ago or whatever So I think that’s the best thing is that I sit in my little cubicle out here my office out here and like try to make something that I hope resonates with people and Maybe they email me and say hey, this was great. I you know Lost my dog too or i’m the father of a one -year -old or I ran a race that was really long or whatever it is but the better result is these things that I don’t actually get to see it’s these connections that people are like You’re helping them stay closer together or keep their relationship going by providing this little piece of art that they share um and for a lot of people like we all have this right where We go for a hike or walk or get coffee with somebody and say hey, did you see this show? Are you watching this show or you did you read this book that came out or? What are you listening? Like what music are you listening to and we bond through those pieces of art that we share and both appreciate So in a small way, that’s like the best way I can Know that I have any sort of effect on the world.
Brendan Leonard 30:08
Honestly Because if you think about it, like how many times do you actually just straight up write somebody and be like hey I really liked your book, you know, um I try to do it, but it’s not as I try to do it.
Brendan Leonard 30:18
Yeah, right. Yeah. I’m like, I’m like, man I should just be doing that once a week, but You know, we’re all busy But to see that this actually the stuff is actually being shared between people is is pretty cool and it’s a lot more It helps Me keep going a lot more than reading random comments that people leave And i’m not sure why they why they do that sometimes but Um So so it’s like that’s that’s the best you can do really, you know, you don’t know like if you were just an author like 40 years ago You would know that you sold some books But like I have books that have sold him for me really really well And I know for a fact that like probably fewer than five percent of people have ever opened that book that they bought. Um because the way it went out in the world was like part of a gift package that you could buy and like It was literally just a it’s like a manual on how to do everything in the outdoors I’m like, I met a guy once who read it cover to cover and I was like, wow Why you did that?
Brendan Leonard 31:18
Um, but I have other books that like have sold a few hundred copies and people have emailed me and said hey This really helped me get through Um, you know cancer treatment or my own addiction recovery journey or whatever and Did I make money on that book? Not really. Yeah, but that’s pretty cool, right? Like Pretty cool side effect is like actually hearing from someone who you you know, you played a small part in there In their life changing in a positive way um so
Blake Boles 31:49
Talk to me about how the purpose question shifted when you and your wife decided to have a kid and then you actually did have a kid when you went from just two people who love doing cool stuff in the outdoors and have freelance writing careers and I assume more time wealth and more time flexibility to where you are now.
Brendan Leonard 32:14
And, you know, I like would like to answer this and not like fall into all the cliches that you hear about having a kid, because I, when we found out we were going to have a baby, I immediately started doing video interviews with friends of mine who were dads and I ended up doing 40 of them and asking them the same 20 questions and, you know, I’m eventually going to turn this into a book, I just have to illustrate it at this point.
Brendan Leonard 32:39
But distilling down this sort of wisdom that people don’t even aren’t even aware that they have, you know, and you do hear a lot of the same things and one of the things somebody said was, yeah, it’s funny, like, one of the questions was what’s something nobody told you about this about being a parent and he said, well, something nobody told me is that there’s all these cliches about being a parent, but they’re all true, you know, he’s like, so that was that was a thing. But honestly, like, it’s really, I don’t know how to how to put this, like, there’s this saying that I, I don’t know who invented who, like, actually said this first, I think it was probably a Knowles instructor or a outward bound instructor.
Brendan Leonard 33:23
But it was if you always eat your best food first, you’re always eating your best food. So it’s like you go on a 10 day eight day backpacking trip and you bring this huge bag of food or whatever and, you know, say you really love M &Ms and you can like try to save all the M &Ms and like ration them out through throughout the week, you know, or whatever, or you can just eat them all in the first three days and then they’re gone. So your best food that’s remaining is your next that’s that’s the best food you have. So now you’re eating your best food. And I think, like, before a kid, what I was doing was still very important to me.
Brendan Leonard 34:00
Like, everything was important, like, just I need to I need to travel, I need to find new things to write about and my art was like literally the most important thing I could do, you know, besides, you know, keeping my relationship with my wife, you know, as good as it always has been.
Brendan Leonard 34:17
But immediately when you have a baby, it’s really hard to be like, no, dad needs to go through hike the Appalachian Trail. It’s very important, you know, it’s like, everything just kind of like the volume just gets turned down.
Brendan Leonard 34:29
And it’s not even like I’m not saying it’s in a negative way. It’s like it’s in a really positive way. Like I literally like the best part of my day, like, no matter what happens in my creative life or my, you know, outdoor life, like the best part of my day is often like sitting on the floor of the kitchen with my kid and like listening to him mispronounce grapes, you know, and like learn to talk and like try it and trying to be a real person or you know, he’s an amateur human being is what I call him. But so like we’re at the point where we can start adding these things back in and like, okay, what do I actually want to do with my time and what sorts of adventures can I do and balance that out and like it’s important to the extent it’s part of who I am still.
Brendan Leonard 35:18
And it’s also how I make a living in some way. And sometimes things come along and it’s like, this is literally a lifetime, you know, once in a lifetime opportunity, I should take it. But it’s like, I’m like, there’s such a huge part of me.
Brendan Leonard 35:31
It’s like, I don’t actually really want to go and be gone for 11 days, I just want to hang out with my kid. He’s gonna be, he’s gonna be two for a year, you know, and like, when you’re gonna miss two weeks of that year all at once, it’s like, oh boy, you know.
Brendan Leonard 35:47
So I don’t know, it’s, I was at when we were about to have a kid, when we were talking about it, I was starting to enter this, you know, this data have reflected that people enter this sort of, you know, maybe like mild depression or even a severe depression.
Brendan Leonard 36:05
We used to think it’s like a midlife crisis, but it’s a U -shaped curve in life where you kind of like get to this point in your 40s where you’re like, is this all there is, you know. And I was definitely starting to get that like, okay, am I just gonna keep doing this stuff?
Brendan Leonard 36:19
And I’m like, I think I’d be okay with that, you know, it would be okay, you know. But having a kid was like, it may, it… they definitely answered that question. No, this is not all there is. There’s this huge, huge thing.
Brendan Leonard 36:35
It’s probably the biggest thing you’re ever going to do in your life, you know, um, and that made things, it’s like, okay, I bet that kind of pulled me out of that with, um, maybe not necessarily purpose at first, but triage for sure.
Brendan Leonard 36:50
You know, you’re like, oh my God, this baby, it’s like a time bomb. We got to diffuse it like a couple of times, like several times a day for like six months. It’s like, okay. And you’re not just being like, you’re not staring out the window going, ah, what’s my purpose in life?
Brendan Leonard 37:04
You’re like, I just gotta get this thing to stop crying and make it comfortable, like feed it, like change type, whatever. That’s what I gotta do. You know? And it’s like, yeah, I didn’t have time for those thoughts.
Brendan Leonard 37:11
And now they’re starting to, you know, he’s two and it’s our only kid we’re going to have, you know, and I’m happy with that. That’s good. It’s like enough, it’s enough of the experience that I can relate to people who have kids, but I can still also relate to people who don’t have kids.
Brendan Leonard 37:25
You know, it’s like this happy, happy, happy medium, you know, on a, I’m still getting my ass kicked. You know, I’m like not anywhere close to the person who doesn’t have kids, but like you starting to be able to sprinkle these things back in.
Brendan Leonard 37:37
Um, you know, and like I used to, it used to be nothing for me to be gone for a couple of weeks or whatever, you know, when we do, it was just us or it was just us and the dog. And now it’s like a couple of weeks.
Brendan Leonard 37:48
That’s huge. Um, I don’t know if I can do that even a day. Like I went out with a buddy, you know, I was just trying to climb a few new to me mountains peaks, you know, like kind of hike in and run down if you could and just do it like semi -efficiently fast and, um, pick this one and didn’t really have that much information on it because there isn’t any.
Brendan Leonard 38:11
And we just got like, it was like, you had to climb between three different summits to like kind of say you’d done the thing. We kind of just really got hung up and we were, we were late and I was like, man, I was going to try to be home by the time, our little guy got up from his nap at three.
Brendan Leonard 38:27
And then it was like, I got, I don’t want to try to be home for dinner at five 30 or six. And I missed, like I left so early in the morning and got home after he went to bed. And I was like really, really bummed about it for, I mean, I wasn’t like crying, but I was like, Oh man, I was so disappointed, you know, and it was like one day, like I’m not saying I need to be there for every single event in his life,
Brendan Leonard 38:50
but it was just like, I just didn’t even see the guy today, you know, and that was so tough. Um, and then if he was, you know, I was sore the next day and he was just like totally, you know, it’s very energetic self and I just got my ass kicked, watched him the entire day.
Brendan Leonard 39:05
So that made up for it. But it was like, it was this thing I never thought I would experience, you know, like, Oh wow, I can’t believe, I can’t believe these feelings. Like nobody told me this was going to happen.
Brendan Leonard 39:16
Um, but I definitely try to avoid that nowadays. Um, being gone for the whole day.
Blake Boles 39:23
But do you think having the kid is somehow related to your shift in your attitude towards your paid work? When you said earlier, I’m doing the outdoor stuff because this is what my audience, this is where they are, and this is how I make a living.
Blake Boles 39:42
Do you feel like you’ve moved into a more practical stage of your creative career where it’s less about the art? It’s less about creating something new and different and yeah, more security focused.
Brendan Leonard 40:01
I mean, um, you know, I think like I was able to do, there were certain things that happened where I was able to like take these big trips and do things that were like what I thought were big adventures.
Brendan Leonard 40:15
And I thought that’s what people want to read about. And that was kind of coming from this sort of like magazine feature writing sense where, you know, it was like, uh, if I want to write for adventure cyclist magazine, I could go to Norway and do a 10 day bike packing trip there.
Brendan Leonard 40:34
And, you know, that was, that was a way to like, that was an easy pitch for the magazine. You’re like, Oh, it’s the scenery sells it. You know, it’s fine. Yeah, you can write whatever, you know, go for it.
Brendan Leonard 40:44
Um, and I knew the tourism people and I could go, I’d go there for essentially sort of free, you know, like they would pay for flights and like a hotel on either end. And then pretty cheap as far as travel writers go, we’re not like, Hey, we need to stay at these spas and like, you know, get these like, you know, four star restaurants, blah, blah, blah.
Brendan Leonard 41:01
It was like, yeah, we’re literally coming over on a plane. We need one hotel room for two nights, get our bikes, ride, you know, one hotel on the other end and fly home. It’s like pretty chill for them.
Brendan Leonard 41:12
Um, and I could do those things and it was like, that was, that was easy. And like, I thought that’s, I’m not sure that that’s what the audience always wants. You know what I mean? Like I think of like there’s, you know, you follow other adventure people and they’re doing all sorts of these crazy trips all over the world, maybe three or four a year, maybe expeditions where they’re like climbing some un,
Brendan Leonard 41:38
you know, unexplored peak in Pakistan or whatever. And they’re gone for like eight weeks or whatever. And that stuff is really cool and inspiring, but I’ve always had like, I already, I know what it’s like to be somebody who lives in the Midwest and has a real job and may get you to do like one big trip a year or like, how do we tell stories that that person can relate to, you know, um, and what,
Brendan Leonard 42:00
what winds them up a little bit. And I think that’s, you know, like your peers, if that, if you think those people are your peers who are, who are doing all these big trips and living out of a van and like staying out of, um, you know, real productivity, productive society, quote unquote, that might be a small portion of it, but I really think people are following people like me, maybe for like some of that,
Brendan Leonard 42:26
but I think they really, I think a lot of people really enjoy these sorts of things. Like, how do I incorporate this into a life that’s already very full with other things? Um, you know, and now I’m like, you just kind of, kind of Asian into it.
Brendan Leonard 42:40
You’re like, well, okay, I’m 45. I got a kid. I got a, you know, a mortgage, very modest mortgage, you know, it’s not like we’re underwater or anything. But, uh, but it’s like, I kind of have those things and like, I do want to explore closer to where I live.
Brendan Leonard 42:53
Um, cause I think it’s very easy to get on a plane and go to an exotic destination and be like, well, exotic to us, you know, a Western audience, um, like check out what I, what I saw. And it’s way harder to like, do those like tell stories about where you live or these small places that aren’t famous or like kind of take a microscope versus, you know, a telescope or, uh, that’s probably not a very good metaphor,
Brendan Leonard 43:19
but like explore where you live and then make it relevant to somebody who lives in, uh, you know, Minnesota, Wisconsin, um, you know, somewhere that doesn’t have 14 ,000 foot peaks. So as opposed to like,
Blake Boles 43:34
The origin of the name is that you’re not a hardcore adventurer, you’re semi -rad. Can you just explain that?
Brendan Leonard 43:43
Yeah, it was like at the time, it was like, I feel like outdoor writing in this may this may or may not be true, but this was early. I was getting all my all my stores are getting rejected by magazines.
Brendan Leonard 43:54
And I was like, I just want to write like what regular people are doing. I want to appeal to that because I think we would cover all these sports, quote unquote, sports, rock climbing, mountaineering, mountain biking or whatever.
Brendan Leonard 44:07
We focus on the people who are the best at it. So it’s very similar to how we cover basketball or football or baseball or soccer slash football. You know, it’s like, who are the people who are the best in the world at this?
Brendan Leonard 44:21
But the thing is, you know, most of us who are in our thirties and forties are not playing American football. It’s just not a thing. You need 11 people on each side. You need pads, helmets, blah, blah, blah.
Brendan Leonard 44:33
So they’re all communicating to a completely spectator audience, probably. Aside from, you know, maybe some high school, college football players, whatever, and maybe their families. But but unlike that, like if you’re talking about marathons, there’s a million people who run a marathon every year around the world, you know, probably more than that, actually.
Brendan Leonard 44:54
That’s like the estimate. Right. And we still focus only on, you know, the front runners like, oh, here’s the top three or whoever is on the podium. But I didn’t really like, I didn’t really grab me about journalism, about the sort of, you know, adventure writing that we did, like who are the best people at it, who are the hardest climbers.
Brendan Leonard 45:13
And like, there’s so many people who are just like, we just do like, you know, we’re pretty average. We got jobs and, you know, credit card bills and maybe families and like all sorts of stuff. And we go to the climbing gym a couple of times a week, maybe we climb outside every weekend or whatever.
Brendan Leonard 45:28
And we’re not we’re not climbing the hardest stuff in the world. So what’s that experience like? And I feel like being able to communicate what the experience is like does end up being relevant to the people who are the best in the world, you know, but also the people who just do it and like maybe barely finished the ultra marathon.
Brendan Leonard 45:50
And like, when I started drawing charts about trail running and ultra running, it was just like, this is the stuff I noticed that’s going through my head or this is what happens or these are like what I think are maybe these sort of things that are relevant or sort of universal to people.
Brendan Leonard 46:07
And like some of the most successful ultra runners in the world follow my social media accounts. And I was like, oh, that’s that’s pretty cool. You know, and I mean, like, I don’t know these people, but I’m like, they must find they must find the humor like relevant, you know, in some way or whoever runs their social media accounts.
Brendan Leonard 46:27
I don’t know. But I think that’s what I was shooting shooting for. Right. Like, how does this feel the same to somebody who works a desk job, but also the person who is like, yeah, living out of a van and is a sponsored athlete and, you know, spends their entire year focused on what they’re going to do to like push the envelope.
Blake Boles 46:48
I feel like you’re speaking to this little dirt bag within a lot of people out there who say it does sound fun to totally dedicate yourself to some outdoor sport or pursuit or travel or even being an artist.
Blake Boles 47:05
But I have bills to pay. There are realities here. And can someone speak to this messy middle ground for the rest of us? Well, I can see why you don’t want to abandon your audience, Brendan.
Brendan Leonard 47:22
Well, it’s also like, I’m just like a real dude, you know, I’m not really just a regular guy. So, and I think like more and more like, you know, even when I talk about my writing workshops I teach, it’s like that I used to talk a lot about how to pitch publications and like publications have shrunk and I’ve sort of come to realize that not everybody really wants to like, not everybody who comes to that workshop and not everybody who wants to learn how to write has like the New Yorker in mind as their end goal.
Brendan Leonard 47:49
And I think it’s important for people to just write stories about their families, even if it’s just like, Oh, this will be something, you know, my kids can read. So they’ll know more about my mother, you know, or whatever her life, you know, like those are important stories and like very few of us have access to that sort of thing because nobody ever thought to write it down, you know, or whatever.
Brendan Leonard 48:11
So I want to try to speak to that sort of thing, like, what are your personal stories that may matter to a dozen people, but may not matter to like hundreds of thousands of people, you know, like, I think that that’s equally important, you know, so it’s sort of that same ethos, I guess, applied to creativity.
Blake Boles 48:34
Yeah, you have this great Patreon post called How to Make a Living as a Creative in which you explained and of course illustrated how you’ve made money over the years and have a great pie chart of your annual income, which I’m sure shifts all the time.
Blake Boles 48:54
For those who cannot see this article magically right now, just tell us approximately where your money comes from, all the different slices in the pie chart.
Brendan Leonard 49:07
Yeah. So, like, I think I actually made that post because I wanted people to know, hey, you’re kicking in a couple of bucks a month to this Patreon thing, which is a way of supporting creators, you know, like, here’s how important your money is, you know, to me.
Brendan Leonard 49:24
So, at that time, I think this is based on what year was my taxes. I had to literally have to go into my income taxes to find this out because I’m very sloppy with accounting. But 29% of my income came from Patreon, which is, yeah, like I said, people just saying, hey, I like, you know, your newsletter or the illustrations you do.
Brendan Leonard 49:47
Here’s three bucks a month or five bucks a month or whatever it is. And, of course, Patreon takes a chunk of that. So, I get whatever that is. But that was 29% of my income that year. The next biggest chunk was merchandise sales because I’ve sold t -shirts and coffee mugs that I’ve designed.
Brendan Leonard 50:08
That seems very lofty. I, like, put some words or an illustration on a mug or a t -shirt and people buy it. That was 29% that year. That has definitely decreased in the last few years. Traditionally published books was 15% that year.
Brendan Leonard 50:24
That’s going to be very close to 0% this year. Because with traditional publishing, you get an advance against your sales and then your book has to sell. Some of my books have had to sell like 30 ,000 copies for me to ever see another check.
Brendan Leonard 50:42
So, I must have gotten an advance that year or payment on something. And that was 15% that year. Freelance work was 17%. I don’t do a lot of pitching nowadays, but I have a column for Outside Magazine, which they literally just republish what I put in my newsletter.
Brendan Leonard 51:02
Beautiful. Yeah, it is, too. But it’s, like, without any sort of editorial input. I think they tend to lose a lot of my stuff because they don’t know what to do with it, which is fine. I still get paid, so I don’t care.
Brendan Leonard 51:15
But anyway, then I’ll get the occasional brand that will ask me to do something or whatever. So, that was 17% that year, freelance work. And then I had a sponsorship through Arcterix, the clothing company that year that has since ended.
Brendan Leonard 51:34
That ended in March. And that was 9%. And then I made 1% off of self -published books that year. So, you know this, too, Blake. We’ve probably self -published about the same amount of books, but you can self -publish them through Amazon and another service called IngramSpark or Lightning Source.
Brendan Leonard 51:56
And you get these little checks or direct deposits. And they send you a report every time you get one, but I never look at these, but every once in a while I do. And I’m like, oh, cool. I made $1 .47 from someone buying my book in Italy.
Brendan Leonard 52:12
It does amount to generally a few hundred dollars a month for me, depending on how things are going or if I’ve been talking about the book or whatever. And I’ve put resources and money into those self -published books.
Brendan Leonard 52:25
It’s not like I’m just raking in free dough, but they make a little bit of money and it helps. I just forget about it because it’s just this direct deposit that keeps happening. But if you dig into it, it’s like comical.
Brendan Leonard 52:40
Like on one hand, yeah, I’m going to be an author so I can make a lot of money. And you’re like, wow, I sold two books in Australia this year. But then you can say, oh my God, two people in Australia bought my book.
Brendan Leonard 52:53
Wow, that’s cool. So I don’t know. But that’s the whole pie chart. That was the entire thing there.
Blake Boles 53:00
Yeah, and the merchandise sales to those come from people reading your posts on your website and then clicking some links and saying cool hat.
Brendan Leonard 53:10
Well, it’s probably more often where I say, hey, this just so you know, I’m still selling these t -shirts or I, you know, you know, I’ll put I sign copies of my books and the fulfillment centers actually just at the airport here in town.
Brendan Leonard 53:26
So I just like drive a few boxes of books out there a couple times a year. So it’s like signed books, coffee mugs, t -shirts, some posters, do some limited edition stuff. But generally it’s me mentioning that it, that I’m selling stuff and or the holidays.
Brendan Leonard 53:44
At one point, at one point it was bringing in like 30 or $40 ,000 a year and it is definitely not now just because Instagram has made it very hard for me to anything to be seen. And I’ve culled back the number of things I’m actually making to like a few things.
Brendan Leonard 54:09
But there was a point there I was like really trying hard to sell t -shirts and sell coffee mugs and they do make fun gifts and the way it’s done for me is they’re not, they’re printed on demand. So I’m not like printing 500 t -shirts and then hopefully selling all of them, but probably not.
Brendan Leonard 54:25
And then having to like literally create this waste into the in the world, you know, so you order a shirt, it gets printed, it goes to you. Same thing with the coffee mugs. So that’s kind of cool. But it’s not a, it’s not a huge risk as far as overhead for me.
Brendan Leonard 54:42
But it’s a minimum way of creating art where it’s like, okay, I’m selling this thing that says something on it. Do people want to wear this on the front of their shirt or would they rather just put it on a coffee mug and maybe not advertise it to the world or how does that work? So it’s been interesting that way too.
Blake Boles 54:58
you and your wife both have creative professions and you live in a cool university town in Montana and you’re able to build a shed in your backyard. You got some space and you’re raising the kid. I feel like there’s a lot of people who think that even that description that I just laid out feels rather impossible today. And I’m wondering, do you guys have any secrets? Did you get any help from your own family members or any forms of intergenerational wealth? Were you able to pull this off as two freelancers genuinely? And perhaps what have you traded? What have you traded away? What have you said no to in order to get to where you are? That’s a lot, sorry.
Brendan Leonard 55:48
Oh, yeah, no big questions. Yeah, for sure. And you know, like, I don’t think of myself as having come from money, but I obviously do at some point, you know, like, I graduated undergrad with I think around $18 ,000 in student loans, but my mom paid my rent when I was in college, which was nice, even though one of the years I was paying $175 a month to live in an attic.
Brendan Leonard 56:14
No, 135, I think. Anyway, there’s that. And I think I got a little help from my parents. The last car I bought in 2005. Like, I think my dad was like, we want to send you some money. And I’m like, don’t dude, I got it.
Brendan Leonard 56:31
You know, he’s like, and I think he sent me 1000 bucks. So and they had, you know, I have a whole this whole backstory about addiction and recovery. And I was a disaster until I was about 23, and was able to go to rehab while still on my parents insurance, which was enormous.
Brendan Leonard 56:51
And then they, they paid off a credit card I had racked up, I think, like $3 ,000 on at that time, which was massive. This is me just listing off all my privileges here. So and I have not had. And then they moved me to Montana the first time in 2002.
Brendan Leonard 57:10
So if they were going to total that up, that’s probably some significant money. And I tried to pay them back by paying for them to go on vacations with me in my 30s, making making some money as a way of saying, okay, thanks for all the, you know, support.
Brendan Leonard 57:27
But yeah, no, we, we have not, I have not had a car payment since college, I had a car payment in college a little bit. So 2000 at 2000, I haven’t had a car payment like 25 years. So we just pay cash for cars that are not, they’re not nice, you know.
Brendan Leonard 57:49
And the house, so I got a, I got a book contract in 2014. And we had just moved into a crappy apartment on Colfax Avenue in Denver, in out of the van. Well, the van, the van was still there, obviously.
Brendan Leonard 58:09
But we moved into this apartment, I got this book contract. And it was a big like, to me, it was a small, a small New York publisher, but to me, it was a big publisher. And they were like, Hey, we pay, we pay you $35 ,000 advance to do this book.
Brendan Leonard 58:22
And I was like, Oh, absolutely. I don’t care what it is. And just broke broken into three payments of whatever 35 divided by three is, but like 11, 11, 667 or whatever. And I was like, this is the biggest check I’ve ever cashed my entire life, right?
Brendan Leonard 58:37
And I write this book, which took several sessions of just like it was like this how to do everything in the outdoors book. Not like hunting and foraging and stuff like that, but like, how to snowboard, how to like set up a tent, you know, how to, how to navigate with a mapping compass or whatever.
Brendan Leonard 58:56
Big amount of work really paid off well. And so with that advance, I was able to put down, what did we put down like a $7 ,000 down payment on a condo that was 500 square feet in this rotting old Victorian house that had been repurposed.
Brendan Leonard 59:16
And anyway, it was, it was fantastic dump, but it was, it was, uh, I can’t believe that house is still standing honestly. Um, but we bought that, we bought that condo in, uh, ooh, jeez, 2016. No, 28.
Brendan Leonard 59:33
Sorry. 2016 bought the condo central Denver, 2016 very good time to buy and sell things. Um, all we did to it was put in a new floor and painted some stuff. Um, which is also money from the book advance and then sold that bought another place, use the money that we profited from the condo to basically kind of flip this place.
Brendan Leonard 59:58
It was pretty not, not awesomely livable. Um, had, uh, bed bugs and a lot of gross things going on. Uh, but we, we sort of just like made it into a home as a little duplex and sold that in 2020 and moved here.
Brendan Leonard 01:00:14
And we are the people who were like out of state money ruining Montana. not in a huge way. We weren’t like, we’re not like rich, but we did buy a house that other people would probably would have liked.
Brendan Leonard 01:00:26
And if this thing was a project, man, and it still is in so many ways, but it’s very funky. And we don’t live, we have lots of friends who live in the nicer neighborhoods in Missoula. And we live in sort of like, we’re one of the neighborhoods that orbit the nicer neighborhoods.
Brendan Leonard 01:00:42
And we live far from the trail heads, but it’s close to me. I’m very excited about it. But yeah, we avoid a lot of the, you know, I don’t have, we don’t have nice cars. I don’t really identify with like the automobile is not really part of my identity.
Brendan Leonard 01:00:58
Like I’m sure, you know, if I was more aesthetically minded, I would not drive a 2015 Subaru Forester because it’s just like not an attractive car, but you know, I’m not like stepping out of the car and like looking around and being like, Hey, you guys looking at me?
Brendan Leonard 01:01:13
Yeah, it’s more like, it’s like this thing is what I use when I can’t bike, or I need to move something heavier than 60 pounds or whatever, you know, and like, yeah, it’s literally a tool. And the other car we own is, you know, somebody scraped FU into the hood, the windshield’s broken.
Brendan Leonard 01:01:33
This happened in Denver when we told this story, but it’s like, is my wife’s car. And she’s just like, you know, I really love this car. And I’m like, yeah, it’s fine. You know, it still works, but she bought it for $5 ,000 in 2012, I think, or 13.
Brendan Leonard 01:01:51
And it’s still cranking, you know, 200 and some thousand miles. But yeah, we just like, we’re not trying to have super nice stuff in very many ways. And I think your question was like, what do you, what do you, what do you avoid?
Brendan Leonard 01:02:06
That was, that’s like, yeah, what if you have,
Blake Boles 01:02:09
had to give up or to say no to in order to get where you are. Nice cars, clearly.
Brendan Leonard 01:02:17
Well, yeah, yeah. And like, that’s, I don’t know, man, you’re a bike guy. And I’m like, no matter how nice the car is, it still sucks to be stuck in traffic. And I’ve always been aware of that. And I’m like, okay, cool.
Brendan Leonard 01:02:29
It’s got all these features and stuff, but I don’t need that in my life. I’m like, it’s literally a tool, like you said. So yeah, I don’t know. We don’t, what do we not spend money on? Thankfully that, I’m not going to get in trouble for saying this, but the restaurant scene in this town is not that amazing.
Brendan Leonard 01:02:47
So it’s like, we used to go, we used to go to a lot of restaurants in Denver that I, and not like, we don’t, we’re not fancy restaurant people. I just like to go to like Mexican joints and Ethiopian restaurants and stuff like that for the experience.
Brendan Leonard 01:03:00
But that adds up. So, so yeah, we’re like, we’re pretty free from that. Plus having a toddler doesn’t, it means we’re not going out in very many nights. We don’t do a lot of streaming services, like, because we just don’t watch a lot of shows.
Brendan Leonard 01:03:16
But yeah, I don’t know. I don’t think we’re like, I don’t think we’re like, you know, avoiding like things that we’re really, would miss, you know, we do have friends who have like a cleaning person come over and clean their house.
Brendan Leonard 01:03:32
And I personally am opposed to that. Cause I just want, you know, Jay, our little guy to see like the dad cleans toilets. Like that’s just, that’s what we do. You know, I don’t want him to grow up and not know how to clean a toilet and like get an apartment and be like, dad, where’s the cleaning lady?
Brendan Leonard 01:03:48
You know, like, but you know, um, I think we can probably arguably afford that and our house would probably be a little cleaner, but honestly, it’s like, I feel like it’s more honest for me to, to do that work.
Brendan Leonard 01:04:01
Um, and, or are both of us to do that work. So, um, maybe having somebody dust would be good. Like there’s just a dust dusting, sir.
Blake Boles 01:04:09
but there’s probably a drone for that.
Brendan Leonard 01:04:12
Yeah. Right. Oh boy. That’d be something. Yeah. Yeah. Sorry.
Blake Boles 01:04:17
I’ll just hit you with one last question, Brandon, which is because it doesn’t sound like you’ve sacrificed very much to be where you are. That’s fine. That’s great news.
Brendan Leonard 01:04:27
The trick, too, is like, I should say this, is like, as far as sacrificing, like, we don’t basically, we basically don’t take vacations, right? Like, we’re not working for a two -week stay somewhere, you know?
Brendan Leonard 01:04:40
It’s like, we sort of figure out how to make it part of the job in some way where, okay, we’re both traveling there, but we need to take some photos or write about it in some sense so that it can become a business expense.
Brendan Leonard 01:04:53
So that’s kind of, maybe the IRS is going to come after me now, but like, everything I’ve ever done where I’ve gotten to travel has been something I’ve written about in some way, so it is part of my job.
Brendan Leonard 01:05:04
So we’re not socking away money to be like, oh, we’re going to try to go to Japan next year, let’s figure out how much money we need. It’s more like, well, let’s figure out how to make this something that is you were able to write about or tell a story about in some way so that it is part of your business, you know, which I think is a huge, huge factor in the fact that we’re not, that’s, yeah, we are sacrificing the,
Brendan Leonard 01:05:32
we always call it a semi -paid, semi -vacation, because we’d be like, oh, we’re in Norway, we’re on this bike tour, and like, okay, can you hold that bowl up and like back up just a little bit, and I’m just going to try to get some photos of this campsite, and like, so you’re kind of working the whole time, but it’s, you’re also enjoying it, but it’s like, you’re not relaxing with your feet in the sand,
Brendan Leonard 01:05:52
so to speak. So.
Blake Boles 01:05:54
You’re talking to someone who has a travel company and can write off literally anywhere I go as research.
Brendan Leonard 01:06:00
Yeah, as my friend would point out, writing it off doesn’t mean you have the money left over. But yeah, anyway, sorry, your last question.
Blake Boles 01:06:11
Well, you’ve managed to create this life that started as more of a traditional dirtbag existence a lot of time in the outdoors, not earning very much money. You were able to develop your freelance writing career expanded into this, this small empire, the semi rad empire.
Blake Boles 01:06:32
And now you have a life that looks a bit more traditional or conventional, I think, by your own words. And you seem genuinely happy with it. And you’ve already talked about the the joys of fatherhood.
Blake Boles 01:06:50
I’m wondering if you can close by trying to think of some recent moment where you have been able to take advantage of kind of everything that you’ve created. I know you said you don’t feel like you have a lot of time, wealth or a lot of flexibility these days.
Blake Boles 01:07:08
But is there something you can point to? That’s like a moment of beauty or meaning or transcendence, some moment where maybe you’re drawing something or you’re on an adventure that you’re going to write about, or you’re traveling to meet someone.
Blake Boles 01:07:20
Someone sends you an email. And it reminds you why you decided to lead this life or to build this in the first place. You know, one of those magic moments. Anything pop into your head?
Brendan Leonard 01:07:34
Oh, that’s pretty big, man. Yeah, I mean. Gosh, bringing it all together is like sort of difficult, and I guess I would just say like every day is really different, but like the focus I have. Like, OK, so the the entire to me, this you may have a different definition for this, but like being, quote unquote, a dirtbag is about freedom, you know, not in the like American man spreading freedom sense where my rights to do whatever I want,
Brendan Leonard 01:08:08
trump your comfort or, you know, your experience. And I don’t have to consider your feelings, but more like freedom that I can do generally what I want to do with my day or my life or whatever in a larger sense.
Brendan Leonard 01:08:23
So it’s like, I wake up today and after we drop Jay off at daycare, one of us bikes him to daycare, I got eight hours to do whatever I want with, you know, most of that is governed by what is the deadline for this thing?
Brendan Leonard 01:08:38
I need to get this done, you know, and like, so it’s not not stress free, but to a pretty big extent, I can kind of do whatever I want, you know, provided that somehow it’s going to lead to money or serve some other purpose.
Brendan Leonard 01:08:53
So a lot of days I’m able to drop him off at daycare and then ride this ridiculous cargo bike with a seat on the back and this giant basket on the front over to the trailhead and then run up Mount Sentinel here, run down, get back on the bike, bike home.
Brendan Leonard 01:09:06
And I don’t get home until like 1045 and then I start working and work can involve a lot of different things. The creative process is very, you know, it’s very nebulous and like things, whatever can be part of your art.
Brendan Leonard 01:09:23
So I think the big thing for me is freedom and there’s, if I were to sit back and say, wow, this is great. I can, I’m doing what I want or whatever I want. I should have more of those moments in the day.
Brendan Leonard 01:09:34
I’m more of an anxiety -ridden person. I’m like, oh God, I gotta get this thing done. I gotta get done by the end of the week and blah, blah, blah, blah, blah, you know? So that’s more of what I think, but in a macro sense, I’m doing less and less stuff that I don’t wanna do for money.
Brendan Leonard 01:09:48
So in general, it’s actually pretty fun on a regular basis. And, you know, you get a, you get to be generous if you run your own business, if you want to, you know, you can pinch pennies or whatever, or you can just be like, hey, I’d like to give away this product or this thing I made, you know, if, you know, to people who support me or whatever, you can choose to try to make money off things.
Brendan Leonard 01:10:16
You can try to make more money. You can refuse to work for free. You can, you know, you can ask people for more money, whatever, but it’s largely up to you. And it’s like, yeah, I am acting on freedom mostly.
Brendan Leonard 01:10:34
That’s the main consideration, you know? If I wasn’t, like we’re able to have Jay in daycare only four days a week instead of five, because we don’t necessarily have to work on Fridays. Generally, a lot of days, we like just trade off watching him while one of us works, but we’re able to be at home with him and watch him grow up and learn to be a human being.
Brendan Leonard 01:10:54
So that’s pretty, pretty amazing too. But yeah, I would just say freedom is like kind of the main consideration. And like, it’s lucky to be able to have enough money come in through what you do to be able to say, oh yeah, I can focus on freedom and not money.
Brendan Leonard 01:11:09
We could have a much nicer house and nicer cars or just like, you know, less, less drafty doors or, you know, whatever. Probably gonna need to upgrade this boiler sometime. But it’s like, you know, this is what we chose.
Brendan Leonard 01:11:25
So it’s cool. But yeah, do I ever think about getting a real job? Probably like three, four times a week, yeah.
Blake Boles 01:11:33
So, yet here we are. Here we are. Brendan, thanks so much.
Brendan Leonard 01:11:40
Thank you for having me Blake, this was super fun.