Jack Schott is a 36-year-old summer camp consultant, former camp founder, and self-directed learning advocate who spends a lot of time thinking about money. (jackschott.com)
Jack occasionally earns $1,500-$3,500 in a single day by running corporate trainings and camp staff workshops: work that doesn’t always light him up, but work that is very useful for buying time, freedom, and very possibly, another summer camp that he can direct.
Jack describes the tension he feels between wanting to do meaningful work and not wanting to be tied down. At his most purposeful, he was co-running a camp in upstate New York with his ex, building cabins by hand and forming deep relationships with kids and staff—but he felt trapped. Now he’s trying to design a setup where he can direct a camp each summer without needing to live on site year-round.
He also shares how he thinks about money strategically: not just for personal comfort, but as a tool for long-term impact, particularly in making camps more self-directed and less top-down. In this vein, he describes how an average 22-year-old could quickly build a high-flexibility career from scratch by cold-emailing lawn care companies (or a similarly “boring,” everyday field of work).
Jack is less focused on outdoor adventure than past guests, but he’s laser-focused on building a life of flexible work and purposeful contribution. His version of “dirtbag” is getting to play outside with kids, every single summer, for the rest of his life.
Full transcript: dirtbagrich.com/jack
Recorded in May 2025.
Transcript
This is an AI-generated transcript. Typos and mistakes exist!
Blake Boles (00:01)
Jack Schott, welcome to Dirtbag Rich.
Jack Schott (00:03)
What’s up Blake? Can’t wait to be here. Can’t wait to be here? I’m already here, come on.
Blake Boles (00:09)
Jack, three years ago, you and I rode bicycles on the Camino de Santiago in the reverse direction, not the direction that most people walk going away from Santiago. And we were dressed in shark costumes, which you brought from the United States. This was a very silly, fun thing to do. We were out there for about three weeks. You were able to say yes to this. What was going on in your life that allowed you to say yes to some silly adventure like this, taking multiple weeks away from whatever you were doing at home. How is that even possible?
Jack Schott (00:39)
Well first I want to apologize for not getting salmon costumes as you desired for that for that trip. The idea was we were supposed to be swimming upstream not not sharks, but it was fun to hear “baby shark” in as many different sort of accents across Europe as we did. Blake, most of the time can take three weeks a month and go somewhere.
Blake Boles (00:51)
True.
Jack Schott (01:07)
And especially at that time, I’m a little self-conscious about whether or not I’m dirtbag rich at the moment in an effort to become more dirtbag rich or at least more purpose driven, more connected to purpose and more connected to and have more financial freedom in the next few years. And so I’m sort of in this like weird, can I take a huge level up in both of those things in the next like?
in past year or so and in the next 18 months or so. And so how did I do that? I just make what I think of still as an ungodly amount of money in single days of work. And some people maybe don’t think it’s that much money, but I make somewhere between 1500 bucks and 3500 bucks for one day of work. And for me, it’s totally still wild that that’s how it works. But that’s what I do.
Blake Boles (02:04)
So you’re an arms trafficker, you’re a tobacco sales rep, you must be breaking some sort of law or some ethical norm in order to make that amount of money in one day. Or you work for McKinsey, you’re Bain, you’re a traditional consultant. Tell me if I’m right.
Jack Schott (02:20)
well, you’re being an arms trafficker. It, while I morally doesn’t line up with the purpose of dirt bag rich does kind of sound, like an exciting, adventure to go on. No, I, so I do two things. One, I, sell trainings to summer camps. and the other thing I do is my friend Sylvia sends me into mostly manufacturing companies, mostly in the Midwest of the United States. And I put on my business costume, not my shark costume, and I help the executive teams sort of talk through problems and their feelings. And I, I, I code switch from authentically connecting or, all of our sort of buzzwords in the alternative education world and all the other sort of like worlds that you and I tend to swim in and code switch all that stuff into. All right. So
When you said you were going to have it done by the end of the day, did you mean 5 p.m. or midnight? And the head of HR has a hard conversation with the head of finance or whatever. And that is, you know, not where I ever thought I would be, but it pays my bills really well. And I listen to a lot of a lot of.
The dirtbag rich podcast before coming on it and we’ve been friends for a long time But I wanted to see like sort of what was happening and my big takeaway is I think about money a lot more than most of the people on The podcast I probably think about money more than most of the dirtbag rich folks that you interviewed or at least I’m happy to admit I think about it more I think maybe some people think about it and it from a stressful place, but
Blake Boles (04:06)
Hmm.
Tell me what you obsess over and tell me what’s going through your head when you’re thinking about money.
Jack Schott (04:11)
I think.
Well, so would I I don’t like being stressed about money. And so I have thought a lot about money to try to get good at money. And I think if you want to get good at something, you have to think about it. And most of the time, people in the worlds that I love to live in are stressed about money and they don’t want to think about it. And so it becomes reactionary. It’s this place of scarcity. It’s like, I don’t have enough of this, so I can’t.
And that’s not how everyone thinks, certainly, but a lot of people live in that world that I know and I don’t want to be like that. I don’t like that feeling. So I want to think about money and I’m willing to sacrifice, you know, sacrifice, quote unquote. It’s like, whatever. I will fly to Cleveland, Ohio. Actually, recently I drove to Cleveland, Ohio, and I’ll sit down and, you know, put on a business costume and code switch into sort of much more sort of synergy style language.
than maybe the clowning that I do when I’m sitting on a bench at summer camp and be able to pay for the next month at least from doing one day of work. And I’m really lucky to get to do that. I…
Blake Boles (05:22)
Hmm. Let’s zoom out a bit. You’ve mentioned the worlds or the communities that you and I are part of. What are these? And give listeners a little bit of background about where you came from.
Jack Schott (05:34)
Yeah, so I grew up going to summer camp and summer camp has been the sort of like through line for my entire career. I tried to leave for a little while, but I love summer camp. love the incredible depth of connection and intensity that happens at summer camp. You were interviewing some folks talking about like through hiking and these adventure activities, and they’re not exactly the same as summer camp, but there’s this similar sort of
time warp that you get to enter when you go and do something that is has that level of intensity and I think you now do this through a lot of the trips that you run the getting back to not back to school camp when you can and I don’t think you’ll be there this summer bummer for them and um but also through the dance weekends and the other sort of gatherings that you throw and that I’m addicted to that I love it it feels so good and
Blake Boles (06:06)
Hmm, mhm.
Jack Schott (06:35)
I grew up going to camp. ended up driving around the country after I graduated from college. And I, with my girlfriend at the time, we visited 200 and something summer camps all over the US. And we lived in the back of a Honda Civic, which like I see all this van life stuff now. And I’m like, damn, those things are so cool. how do you afford that? And now the way I would afford it now is I would work very, very specifically.
for these silly manufacturing companies one day a month. But I don’t do that at the moment. Anyway, I think I grew up going to summer camp. I grew up loving summer camp, end up starting a summer camp after driving around the country. And one of the things I love about summer camp is that it is this intense, you know, couple of months or couple of weeks that can pay for most of the rest of my year. And there’s work to be done. There’s computer work to be done and there’s families to talk to and there’s whatever, but
It is a very intense, you’re locked and loaded in a very specific place for a very specific time. And it ends as a start date and an end date. And I love the experience and I love the financial realities that come from that kind of work. And so then I chased that. And most of my life, except for camp, I’m, I trade the purpose part for the flexibility part. So I’m happy to.
show up and work with a manufacturing company to work through whatever sort of cultural problems they’re having. And I don’t particularly like, know, sorry, no offense to American manufacturing. I don’t have a huge passion around increasing throughput on the factory floor. But it gives me the huge flexibility that I have in my time to say I’m going to block out a month and go to Spain and wear a Shark Costume with Blake.
Blake Boles (08:32)
There’s so much to unpack here, Jack. I want to start with the money realities of working at summer camp or doing something similarly intense for this very specific period of time that you were talking about. Because as you know, I have organized my life similarly to run these intense trips or retreats. I know exactly when they’re starting, when they’re ending. It’s 24-7 when you’re doing it. And there is some computer prep work beforehand. There’s a little bit of computer stuff to do after, you can really do that from anywhere when you want. It’s super flexible.
So after you do this super intense period with a little bit of computer admin before and after, then you have a pretty good idea of how much money you’ve made. And ideally, you can have the sense of freedom and spaciousness because you’re like, okay, I will be done working. And everything else I need to do after that is really quite easy and straightforward. And I know how much money I have to work with. And for me, that has led to this natural sense of budgeting.
And it’s like, okay, I have this much money that I made from this program and I have X number of months to live off of it. So I need to be careful and not just look at this large number in my account temporarily and think that that’s gonna be there forever. Is this the kind of money awareness or skills that you’re thinking of that you’ve learned by doing this kind of work?
Jack Schott (09:56)
Yeah, and I think that the, where I struggle, and I was struggling at not back to school camp last time we saw each other, with this problem of purpose and freedom having tension in my life. Like I couldn’t figure out how to.
Continue to have the kind of freedom that I wanted to have and Start to do more work that I felt purposeful about like I wasn’t running a camp at the time I was doing much more of the corporate consulting that I just was describing I was running staff trainings for for summer camps, which is like a Great, it’s fun, but it’s not you know, it’s like I go in for a day I do a bunch of activities and help people think about how to connect with kids and then I leave which is again a great way to earn a buck, but it doesn’t make me feel like
Blake Boles (10:27)
Mm-hmm.
Jack Schott (10:49)
you know, waking up every day and being excited to do the next thing. And so.
Blake Boles (10:52)
So let me just jump in here. What was your maximum purpose moment? If you can just choose a moment or a season of your life where you’re like, am doing stuff that matters, I matter, this all feels like it’s dripping with purpose and meaning.
Jack Schott (11:08)
Yeah, probably my maximum purposeful moment was toward the end of my time at stomping ground. So I started a sleepaway camp in New York with my girlfriend at the time, ran it for seven years. went from zero kids to with 64 kids the first summer for one week. We rented a site. And then when I left, we had acquired a property. It’s an independent nonprofit. So, you know, we being this like entity had acquired a property and built it from, you know, by hand we were building cabins and running water lines and it was, it was awesome. It felt like really connected both to the place and to the kids and the families and to the team that we were working with to build it. So full of purpose, but really lacking flexibility at that time. You know, like I was locked in. Like if I wasn’t there and the water went out, like George was hopefully going to be able to fix it, but you know, it’s going to be really stressful on everyone. And so I was locked into this, this place. And so it felt really good to be doing the work and I loved the team. I felt felt purposeful with the team, but also I was, you know, stuck.
Blake Boles (12:24)
Do you think this whole dirtbag rich concept is kind of a sham? Like that people are actually not made for this high degree of flexibility and freedom and they really find purpose in these like deep attachments to person to place to community. Like you need to be locked in. You need to not be able to leave so easily. Kind of like you were at stomping ground for something to actually feel purposeful in the same way that when you’re a parent, you know, you’re not just going to leave, you know, someone really needs you and is depending upon you. Give it to me straight, Jack.
Jack Schott (13:00)
I hope not because I’ve, I’ve designed, I’ve designed this the last, I’ve, committed to, to about two and a half years of trying to get back to maximum freedom while getting maximum purpose. And I need more financial reality to more, more money to be able to make that happen. So, so I I’ve decided to spend the last year and about the next 18 months to hopefully get back to running a camp, having a camp that can.
that can sustain itself, deep connection to the space for folks that come every summer and the ability for me to have a lot more autonomy in where I spend my time and how I spend my time. So I hope not. I do think that there is a depth of connection that happens over time and most people have built their lives around
Blake Boles (13:55)
Hmm.
Jack Schott (14:00)
repetitive things so it’s easy it’s much easier to Be connected to the barista at your local coffee shop if you go every day for 10 years Absolutely, and most people sort of live relatively stationary so it makes sense that that most of our models are built that way, but but you Have communities that you go back to regularly and
Blake Boles (14:10)
Mm-hmm.
Jack Schott (14:31)
You have people that you go back to regularly and you have work that you’re doing right now. I don’t think you’re doing this podcast to make a lot of money. Hopefully, I hope that dirtbag rich, the idea of dirtbag rich, the book, whatever makes you some money. But that’s not why you’re doing it. You’re doing it because you are trying to explore this idea. I’m guessing you’re trying to explore this idea for yourself and you’re trying to make it more accessible and create an opportunity for other folks who are feeling this itch, who have itchy feet, who are like, I feel like I want to keep moving. I loved being an outdoor educator when I was 22, but how do I make this a thing that I can do for longer, where I feel like what I do matters and I don’t have to be stuck in the same place?
Blake Boles (15:21)
I’m doing it because it’s the most interesting thing I can imagine doing at this moment in life. And it’s for other people, but it’s also more for myself and to figure out my own psychology and motivations and history and like have some, have like a cohesive narrative. So you’re right on most counts there.
Jack Schott (15:43)
But you’re doing it for me too, right? Like like, like you, you’re, I’m happy to pay $23 or whatever for your book. And I’m happy to, listen and, and, you know, because you’re, you’re, you’re working for me and you’re doing that because you’re going out and finding out about what it means to be dirtbag rich, which like you and I are not the same, but we have lots of overlap around this.
You know around so much of what you write about so you’re by telling the story better about being about dirtbag rich You’re helping me and so That’s where the purpose Community overlap happens and I don’t I don’t know how to define all this. This is why you’re the the dirtbag rich guy But i’m appreciative of what you do and I think that many people are also Use you as a sort of blurry mirror to see themselves a little bit.
Blake Boles (16:44)
Hmm. Thank you. Let’s dig a bit more into your current situation, which you’ve been describing, Jack. Be a bit more specific. Tell me where you are in this process of trying to get back into the summer camp world, how involved you’re going to be or not be, and how this is going to be different from the last time you were running the summer camp.
Jack Schott (17:09)
I heard a quote recently that was, solve rich people problems, charge rich people prices. And, I, it really made me think about the way that I’ve been able to design my life, which is when I go and do these consulting and training things for summer camps, I do them for camps that charge a ton of money. their kids to go to camp or they have some kind of endowment or they’ve somehow gotten their hands on a lot more capital than we had at stomping ground where we were just eking out everything that we could do just like every other alternative school is trying to do our best to figure out how to do this. And I don’t have any moral
I have anything negative. I don’t I don’t care. I don’t I’m not one of the eat the rich people. I don’t care. I hope everyone can live their awesome life and So I started thinking about how could I get purpose out of running camp as well as get more flexibility for my life and be able to you know have the freedom that I that I want to continue to have and so I started trying to understand these camps that are much more expensive to go to for kids. And I realized that there’s a lot of them. There’s a lot of camps out there that charge a bunch of money for kids to go to camp. And they’re awesome. They’re awesome camps. They care a lot about kids. are in many ways the most self-directed time for kids to spend in a year because these kids tend to be in conventional schools and… They are told what to do most of the time. The average kid sits for seven hours a day. And so I was like, okay, well, let me learn more about that. And how do you become someone who runs one of these camps? And so I took a page out of my Blake Bowles book and I put together a group of people around my age who are on their way to or already owned these camps. And I invited 11 of them to spend a weekend with me in New York.
I talked to them, heard them. They, tried to help them solve their problems and we all brainstormed and came up with cool ideas and whatever. Awesome people. And so then I said, okay, well, how do I own a camp? And I’m not rich. My, didn’t, I’ve never made more than $60,000 a year and I’ve never, um, you know, my parents are, my dad was a professor and my mom was a teacher. Like, you know, I didn’t grow up super wealthy. And so what I did is figured out that what happens is there’s all these boomers, there’s all these boomers who have businesses and they want to not own them anymore because they don’t want to run them. But who can run a summer camp? There’s not many private equity funds that are out there trying to buy up summer camps. And so I said, OK, well, let me go make some friends with people that own camps and be the guy that they think of when they might want to sell their camp. And so now I’m in the process of acquiring a camp that I will, you know.
I don’t have the capital to put down myself. And so there’s, you sell or finance it and there’s all these things. And again, back to understanding money is a huge part of how to not stress about money for me is I opened up ChatGPT and asked a thousand questions. And hopefully in the next year, I’ll be able to tell you, Hey Blake, I own a camp. You should come run another program at the camp. And the hope for me in running this camp is that
The camp is a full business. It’s got employees and it has a whole system. And what I’ll be able to do is run camp in the summer, be there all summer, be connected, talk to families, be the sort of cultural head of the community, which is what the camp director is at every camp, but not be stuck in a spot, not have to be in New Hampshire for the entire year. And I know that that’s possible because I went and met all the camp directors that I know and most of them that run these kinds of camps don’t live at their camp and they have extreme flexibility whether they choose to use it or not. Some of them do and some of them don’t.
Blake Boles (21:36)
Let me see if I got this straight. Earlier, when you were running Camp Stomping Ground, you were a bit more in like the, social entrepreneurship kind of startup realm where you’re, constantly bootstrapped looking for new ways to bring in money, not trying to charge too much money to people. Cause it’s really this idealistic, mission at its core. And you worked your butt off. You enjoyed a lot of it, but you also felt a bit, swamped by that. Then you went into this.
interim period where you took the skills you built during that time and you became a consultant. You put it on your business suit. You went and taught the manufacturing executives how to talk nice to each other. You play some working out games with them and you made a lot of money doing it, which purchased you free time, but left you feeling a little bit hollow inside and thinking, I don’t want to do this for the next 30 years. And now you’re trying to get back into this summer camp game, but not in the same way that you did before. You want to be a bit more of what seems to be a traditional owner of a camp that, as you said, maybe serves wealthier kids and you can charge a higher amount of money for that. You can still be part of an integral part of the community and have that long-term relationship building with campers and with staff year after year, but you are fundamentally able to earn enough money whether or not you’re really spending a lot of time at the camp so that for the rest of the year in the non-camp season, which is a long season, you can go off and do whatever you want, but you know that you will come back to this purposeful place each year that where you are cared about, you are valued, you are needed, and you are not just the consultant who runs a great weekend course and then people kind of forget about you afterwards. How did I do Jack?
Jack Schott (23:30)
You did great, right on. Three months of the year in tents, June to September, June to early September intensity at camp. And then nine months of, there’s computer work to be done. There’s content to be created. There’s excitement to build, but there’s not, wake up at 10 tomorrow, wake up at seven, you know. Blake sends you a text and says, hey, let’s go bike through where’s your next bike trip like and and and able to say yes and…
Blake Boles (24:03)
Insert fascinating place here.
Jack Schott (24:11)
live a different style in three hours of work, be able to keep up with the emails you’re supposed to keep up with and jump on the different call and whatever. And it’s not perfect. Listen, there’s going be amount of time where I have to earn the trust of the community where I’m going to have to be more intensely focused on work than I want to be in a couple of years. But the, you know, the examples, I didn’t like the examples that I was seeing of fire, of a financially independent retire early, where it’s like you, you just grind at a tech startup or a meta or whatever. You make a couple hundred thousand dollars for a few years and then you retire and you don’t work again. I like working. I like the, the act of creating things that matter to people. And I’m not saying that that folks at FIRE aren’t ever going to come back to doing that, that didn’t excite me. So what I want to do is intensely build the connection to camp, this community and care. are, you know, these are going to be families that are going to be connected to me for the rest of my life. You know, they’re going to care about this camp. They’re going to, you know, you still talk about the camp that you went to as a kid or I’m sorry, that you worked at, that you worked at and, and, and, know, cause it matters. And
Blake Boles (25:30)
Mm-hmm, mm-hmm, buzz, yeah.
Jack Schott (25:36)
So to deeply invest in that community, in the short term sprint and in the long term, you know, connection over time, it’s awesome. I get to, I get to, to build a business that lets me live the lifestyle that I want to, that I want to have and intentionally, you know, do that. And will I mess up and probably occasionally end up working too hard because I get stressed out? Yeah. But I, that’s me.
Blake Boles (26:03)
Let me dig in here a bit, Jack, since we know each other and I know that you can take it. I’m not yet convinced that you have a vision for what you’ll do with your free time and your money in those nine months. You know, you got to do a little bit of admin work, continue being present in the lives of these families. That’s all true. And as you know, other guests that I’ve interviewed have mostly these like kind of outdoor, physically intense passions, know, climbing, hiking, biking, sailing.
Jack Schott (26:07)
Yeah, push on me.
Blake Boles (26:31)
that they are really focused on. Maybe they’re more into like the race and competition side, or they just want to go spend a lot of time in nature by themselves or with a loved one or with some friends. I haven’t yet heard how you want to spend the time and money that you’re going to create with these camps. I’m ready.
Jack Schott (26:50)
Well, I want to do two things. Like, I want to do two things. Like, I want to do two things. One, I, well, three things. One is not a thing. It’s just a version to a thing. I don’t want to be told what to do. I being told what to do. That’s been a theme of probably everyone on this podcast in some way or another is not wanting to necessarily be told what to do.
Blake Boles (27:07)
Clear.
Jack Schott (27:17)
I’m bratty about it. I don’t like to be told what to do unless I’m agreeing to be told what to do like You and I bike through bike through Spain. You tell me mostly what to do Every day. Hey, we’re gonna bike to this spot This is what’s gonna happen. Like I’m like, okay Blake. I’m in sign me up Let’s do what you want to do because I agreed, you know I gave consent at the beginning that basically I was going on Blake’s trip and we’d figure it out and so Mostly I don’t want to be told this to start there second. I think that I don’t know how to use the money is back to purpose driven is I see kids being told what to do most of the time. And so I want to create camps so that that that’s possible where kids aren’t necessarily told what to do and they can live in deep connection and da da. But also with the property and with the money that comes from that, it becomes much easier to start to help other entities that want to help kids not be told what to do. And this was one of the cornerstones of Stomping Ground. And I left Stomping Ground, to be clear, I would have stayed probably there for the rest of my life working. But I left because Laura, who started Stomping Ground with me, and I broke up. And she’s awesome, and she runs camp now. And I didn’t want to wake up every day and work with her because it just didn’t feel great. And so…
You know, I’m in some ways chasing this re chasing this dream so that I can rebuild the flywheel. That is how do you help kids have be told less what to do when they go to school or whatever? And anyway, the money, the sort of the money part is largely to be able to have more impact in those communities. And we can come back to that and we can do an off trail learning podcast about it if you want. On your old podcast. And then what do I want to do is I want to be able to build my own little summer camps for me and go on little summer camps for me. And they might be biking or they might be, you know, the ones the ones you’ve organized that I’ve been on are going to work at not back to school camp or going to meet up in Montana with a bunch of people excited about self-directed education or biking through through Spain. Or I was just in
I was just in Texas for a couple of weeks with some friends dreaming about summer camp and I rode the train across the US from Michigan to the West Coast and back. I want to be able to sort of deeply jump into these little experiences with people to build connection just like summer camp. And they may not. It may not involve climbing or it could. You want to go climbing? Let’s go. It’s the activity. Each activity is less sort of interesting to me than the people and community that organize around these activities.
Blake Boles (30:29)
Yeah. Yeah. Your, your version of, of climbing or long distance biking is serial entrepreneurship. Like you want to, to incubate other projects, collaborate with people, maybe help them get off the ground, uh, share your insight. This is what I’m hearing. And, and you want like a diversity of experiences. You want to be able to just be invited to do something and be able to say yes. Uh, 95 % of the time.
And this might look like a silly adventure like the the Camino and Chart costumes. It might look like, hey, I have this grand vision. I’m not sure how to enact it. You’ve done this before and you can show up and you can coach someone through it. But it does sound like you, yeah, unlike other people I’ve interviewed, you are more socially focused and more like, let’s build something. I want to help you build something. And every now and then let’s just like do something fun and crazy together.
That’s what you want to be able to do with your time and money.
Jack Schott (31:31)
Thanks Blake. We recorded this, right? I can send it to my mom, Pam Shot. Pam, did you hear that? Entrepreneurially minded, he said. Not just a vagabond.
Blake Boles (31:34)
Yes. Shout out to Pam. Good. Well, now that we’ve established all that, Jack, can you tell me how to make a lot of money in a short period of time?
Jack Schott (31:56)
I actually have an idea for this. I want to recreate. This is my hypothesis. If I was 22 years old and I wanted to be able to live a dirtbag rich lifestyle, more similar probably to other people on the podcast maybe than me in some ways, but whatever. You can pick whatever you want. I think that what I would do is recreate what I did right out of college, which is drive around the country and visit summer camps, but I would pick a different industry that I knew had money. So, American manufacturing is, is a perfectly reasonable one to pick. And it sounds boring, right? So, so we’re going to give up some, some level of, purpose in exchange for faster freedom. And.
I want to spend one year driving around the US, visiting specific businesses that I know have disposable income. And so what I would do is type into chat GPT, what are 15 examples of businesses that would fit this category? And then I’m going to start cold emailing a whole bunch of these businesses for one year.
And I’m first I’m going to build a really simple website that says like manufacturing coast to coast or something, whatever you can pick, pick whatever you want. And I’m going to try and visit and take some photos and write some blog posts and maybe build an Instagram presence around the, you know, what each business is doing. And I’m going to try and understand their problems and share the solutions that they’re coming up with. I don’t need to know anything about these businesses to start off. I’m just curious. And when you’re 22, people will let you come and talk to you because you’re curious. so then I’m just going to share about what’s the reality of American manufacturing. What’s the reality of lawn care businesses in small cities? What’s the, like these things that are like, you know, like couldn’t be less interesting to normal people, you know, but are really interesting to the people that run them.
Blake Boles (34:04)
Ooh, nice.
Jack Schott (34:12)
Whoever is running any business cares about the business. They wake up every day and think about it and you’re gonna my my what I what I think I might do is build a little personal brand around being the guy that is trying to understand these businesses and I’m only saying nice things and I’m sharing I’m talking about how cool they are and I’m making them look good and whatever along the way I’m probably learning how to take better photos. I’m learning how to take make videos. I’m learning whatever all kind of stuff so that a year from now, I am pretty smart about stuff. And by then I’m gonna have learned what the problems in those businesses are. They’re probably going to need things that are pretty easy for relatively young people to figure out. They’re gonna need a website or somebody to manage their social media or whatever. And then I’m gonna sell it back to them, sell it back to that world at a rate that seems totally outside of your mind for someone who’s 22. Like I’m going to be like, yeah, I’ll do that for $10,000. And, and they’re going to go great. Or they’re going to say no. And you’re going to go find another one to say, like I think in one year of showing up and doing something like this, could easily build a business that brings you in 60 or $100,000 a year in services that take a day a week to offer back to people.
Blake Boles (35:50)
I love this, Jack. And this could be a whole kind of gap year curriculum like Jack, Jack shot’s crazy one year challenge for post grads. Not so crazy when you see how some of them ended up. And it really points to how you and I think similarly about self-directed learning. So now we’re gonna cross some wires here in the self-directed learning space and then the dirt bag rich space because there are crossovers. And what you’re essentially describing is
You know, I think it was Cal Newport, author, in one of his early books, So Good They Can’t Ignore You, who made this case for like not following your passion as a kind of university or just out of university age person. And instead, not doing something quite as cool and radical as what you’re suggesting, but focusing on how you can be the most useful to the world or like some little slice of the world.
And I love your example, not just of like manufacturing, but of like lawn care. Like that’s an example of a service, like HVAC, a service that is absolutely important and essential and it’s being done all the time. And it’s kind of invisible. And the people who do it are not usually lifted up or, or talked about or in the public eye.
And you’re right for a 22 year old or like a small group of friends to go around and be like, we’re just like checking out all the coolest and the highest rated and best reviewed lawn services across the East coast of the United States. We’re doing this for a year. That’s just so weird and interesting and kind of gloriously like idiosyncratic that of course you’re going to get a yes. And it almost doesn’t matter what the field is if you can get enough yeses to go deep into this. And like you said, you just, learn all these other skills along the way. My question for you, Jack is if you had pitched this to me when I was 22, I would have said like, that’s kind of interesting. I want to go do the stuff that I love and that I have this romantic idealistic attachment to be not nature and traveling and getting to work with cool kids and I and I want to be hanging around with other people my age and maybe like people I can fall in love with or become best friends with and and not like a bunch of lawn care dudes You work with people who are this age who are camp counselors or becoming managers of camps What’s the the way to get into their their hearts and minds to sell this kind of idea? Which is brilliant in many ways, but is also a very difficult sell for idealistic driven young people.
Jack Schott (38:48)
Yeah, I agree with you. I got lucky when I didn’t do this, right? I went and visited summer camps, which I liked. It was cool to go see summer camps because I was excited about summer camps, which maybe is actually a big is important here. Maybe you have to be excited about something like it would have been hard to convince me to go at the time, visit a bunch of lawn care businesses because I wouldn’t have been excited. So would I have been willing to sort of
Grind for a year like i’m saying I don’t know I think If I could map out this year And revert like so so let’s build the year, right? I want to go see if I am a person who sees a hundred kinds of a business in a year I am I’ve probably seen more of that that kind of business than everyone but the top 1 % of people in that business. So in a year, if I want to see 100, I’ve got to go see two a week or the way I would probably do it is I try and batch it as much as possible. So it’d be like, can I go see 25 in five weeks and then maybe not do any of it for three weeks? I just like working that way instead of like, as I get bored. And so if you do it, if you do it that way, so then let’s say there’s, I want to see 50.
I want to see a hundred of these things, so I want to go. That’s going to take me 10 weeks if I go see one a day. That means I’ve got 40 weeks throughout the year to go to the dance thing that I want to go to and go climb and see the national park and have the second Instagram that I’m running. So I look cool to all my friends that has nothing to do with the thing that’s going to make me money later. That is just like me traveling and all the like I get to look cool and and
And I’m not saying people only do things for Instagram, but I think a problem set that’s solving here is like, you’re like, yeah, Jack, that earns you status in a community of people who I don’t care if I have status in. What about the status I want to earn with the people that I do care if I have status in, which is the other people my age, because I’m trying to build friendships and whatever. And so I think if I map it out like that and say, I’m going to work two weeks at a time, then I’m going to take two weeks off to do…
Blake Boles (41:01)
Mm-hmm.
Jack Schott (41:12)
all this other stuff that I want to do, then I’m going to go, and by working, mean, visiting these, you know, going to visit every lawn care business in Nashville, you know, or 10 of the lawn care businesses in Nashville. And then, then I’m to take two weeks to, you know, just enjoy what, Eastern Tennessee and Western North Carolina have to offer through. And then the next month I’m going to whatever. So that’s one month. Every month I work, I visit things for half the time.
I visit businesses for half the time. I enjoy my life the way I like to enjoy my life the other half of the time. It becomes more compelling, I think, to think about it like that. It’s like, oh, and it’s an easier sell to your parents if you have parents who will worry about you being a dirt bag like my parents did do. I’m not sure. Pam, are you worried about me? And so I think, you know, if I can map it out and then say, the other thing is,
Blake Boles (42:01)
Shout out to you, Pam.
Jack Schott (42:09)
If there’s a, I would happily like, Blake, maybe you and I put together a fund. This is why I need to figure out how to make more money, put together a fund. Jack and Blake’s $100,000 a year fund. We’re going to give away $100,000 a year to groups that want to do this with, you know, some kind of reasonable interest. So instead of taking out a school loan, do this instead and we’ll bet on you and we’ll help you do cool stuff.
Blake Boles (42:36)
going all Peter Thiel on me.
Jack Schott (42:38)
And a little different, but I understand what you’re the Thiel Fellows have returned a lot of great things for the world and some terrible things for the world. So I just think that there’s an opportunity here for people to rethink what they want, if they want to. And I don’t care if they don’t want to, I don’t want them to. But if we don’t, what I like about Dirtbag Rich and is…
You’re painting a different picture for what’s possible for folks and and illuminating it so they can have a different decision I can now see a 40 how old you? 42 year old who lives life drastically differently than what my parents have said 42 year olds normally live their life like And you’re elevating that and then you’re sharing the stories of other people who are doing that and then the the for me the gap is if I want to go from i’m 22 to
Blake Boles (43:17)
42.
Jack Schott (43:35)
I’m living a life that is more like Blake’s life or more like Kaya’s life or more like these other people that you’ve interviewed. How do I go from here to there? And I think it’s you earn the ability to sell something at a higher price than you think is reasonable. So that and most of the time for me, that’s my time. And you could build a product or whatever. I don’t know how to do that, really. But I know how to sell my time for more money because I have a reputation inside the camp world.
Blake Boles (43:54)
Hmm. Mm-hmm.
Jack Schott (44:04)
I have a reputation with Sylvia who sends me to all these businesses. She has a reputation in those businesses That people trust and so how do you how do you build that one way? I think is to go visit places and earn the credibility by by showing up like that. Another way would be to You know get a degree or whatever. I just don’t think the degree gives you the same. I Just don’t think the degree gives you the same The degrees are fine. I’m not anti-degree, but it just doesn’t it doesn’t get you to the front of any lines
Blake Boles (44:32)
Yeah, yeah, yeah, you’re still one among many. Jack, you’ve thoroughly proven your thesis that you think more about money than the average person, even the average dirtbag rich person. And who in your life thinks more about money than you do?
Jack Schott (44:52)
Lots of people think more about money than I do. And I think what I am interested in being, what’s interesting to me is trying to put myself into communities where I am the least of what is normal for that community. So like going and spending time with camp owners who spend a lot of time.
thinking about money way more time thinking about every dollar that they spend than me. I catch up so much faster to being able to think about the camp finances than I would if I like read books or whatever going in and living, going biking with you through, through Spain. I’m the least biker-y of everyone that we’re, that we’re, we’re bike packing with by an order of magnitude. And I’m going to catch up a lot faster by being with
Blake Boles (45:34)
Hmm.
Jack Schott (45:52)
with all of you going to, so that to me, that’s what lets me catch up on this stuff. And you get a cheat code to just podcasts are just the same thing. You get to learn the, if you learn the language of how people speak and then you provide something else, then I get to play in their world without having to be an expert.
Blake Boles (46:18)
All right, I’m seeing another way that you, that this is your version of being a dirtbag. This is the thing that you’re addicted to. You’d like to insert yourself into communities and subcultures where you are the outlier. And that means you have the chance to learn the most out of anyone there. And you’re just like a big learning sponge, right?
Jack Schott (46:39)
Yeah, love it. It’s that sounds like I’m a parasite. It’s I do think that there’s a there’s a you got to show up and provide some value, you know, like not like, you know, to give anybody money necessarily. But like if you just show up and you’re just like stealing from the community that nobody wants you there. So you got to you know, how do how can I be useful to people in the community? How do I make people laugh or make nachos or you know, whatever or or help people brainstorm?
Blake Boles (46:43)
Yeah
Jack Schott (47:06)
about where I have found myself to be quite valuable in youth serving alternative ed style places is I care about the work that people are doing and understand and really dig in. But also I think about money again, way more than most of the random folks that start these little schools that are hugely purposeful and purpose driven. And I really want to exist, schools or learning communities or whatever, but they almost always fail because they don’t build a business model that lets them, you know, live the life that they want to live once they have kids and whatever.
Blake Boles (47:51)
Yeah, that’s the story that you and I have seen played out over and over again, unfortunately.
You once told me that you work like a lion, not a cow. What does that mean?
Jack Schott (48:04)
I heard this quote that’s from sort of the tech bro philosopher of choice, Naval Ravikant, and he said, work like a lion, not like a cow. And I really liked that because the idea is lions sprint, catch an antelope or whatever lions eat, and then sleep for the rest of the day. And cows just munch all day long.
And I’m more, I’m already bored. want to work extremely hard and I’m happy to work extremely hard. Working at camp often is extremely hard. I’m happy to work really hard in this like weird way of working hard that is put on a business costume and have intense focus to help people work through their problems and then leave, which is much different than working super hard to build a cabin or whatever, which, you know, but I want to do all those things. I want to work really hard and then not have to work and figuring out the timeline is the part that I still am struggling with. What’s the right sprint for me and then the right do whatever feels good in the moment for me.
Blake Boles (49:20)
How to be the lion.
Jack Schott (49:21)
How to be the lion.
Blake Boles (49:24)
Jack, can you tell us a little bit about your own podcast and the writing you’ve been doing? You’ve been really increasing your, your public presence. not just like the title and where to find it, but like what, what’s been the mission behind what you’re putting out in the world lately.
Jack Schott (49:41)
Well, I believe that summer camp could be the gateway drug to much more self-determined living for young people. Largely summer camp is, sleepaway summer camp in particular tends to be some of the places where kids get to make the most choices if they go to conventional schools, if they do whatever. But most of these summer camps are not that choiceful. They’re mostly not that self-determined. They’re not that self-directed. And so my hypothesis is that if I can help summer camps start to be more, you know, focused on partnering with kids instead of powering over, if I can help summer camps start to give more kids choice and self-direction than
There’s 22 million kids a year that go to sleep boy camps or dig that go to summer camps in general in the US today. That’s like a quarter of the total kids in the in US I think is the math. That’s like a lot of kids and I don’t know how to change the school system. I don’t have a good business model at the moment for how to have a bunch of awesome self-directed schools or community centers or whatever. I don’t know how to do that.
But I do know that most camp people are directionally hoping for more of the same things that I believe are awesome for kids. And it’s a skill issue for them to figure out how to build communities and programs that are more self-determined. so my hope is I can continue to build trust and continue to offer opportunities for people to move in that direction. And so that’s the sort of purpose of all of my writing and talking to random people on podcasts like you or the people on my podcast.
Blake Boles (51:50)
like Seth Godin.
Jack Schott (51:52)
Like Seth Godin. Who? Big summer camp guy, Seth Godin.
Blake Boles (51:55)
Right. well, I really admire and respect the work that you’ve done in this field. And you’ve really been a bridge between what feels to me like the more traditional summer camp world and this world of self-directed, highly idealistic self-directed education. And you’re able to exist in both of them and to cross pollinate between them instead of letting them live in two separate silos. And I think that’s, it’s a really big value and to give language.
to the value of camp beyond time and nature or making friends or social emotional learning and say like, no, like this is how you learn to become an autonomous empowered individual who can harness your freedom and who can self organize. Like this is actually much deeper than you think camp might actually be. So you are that guy, Jack. ⁓
I would love for you to close by sharing a memory, any memory from all your time at camps. It could be the camp you’ve run or one that you’ve visited or consulted for, but something that stands out as like, this is the point of it all. Like this, this is why I’m doing what I’m doing. This just symbolizes everything that camp could and should be.
Jack Schott (53:15)
Raise the stakes, raise the stakes, keep them going and it’ll change the world. And if I say this perfectly, then kids will wake up tomorrow and have a chance to choose how to spend their, and they won’t sit unless they want to. And they won’t have to listen to teachers who are well-meaning, but are stuck in a system that they don’t enjoy. And Jack, if you can deliver this one minute speech, then.
Blake Boles (53:18)
Small ask, how about just a nice memory from your time at camp? something that represents purpose and meaning to you. Why are you doing all this?
Jack Schott (53:49)
Yeah, right on. Well, thank you, Blake. I, it’s funny, I planned to ask you a lot more questions, but you kept peppering them in. I didn’t get a chance to flip the script on you, which you know I’m likely to do any time we get together. So in 2015, Laura and I started Stomping Ground and we got together, like I said, 64 kids and 20 of our best friends, we asked to come volunteer to work with us.
And we were on a mission to try to treat kids the way that they want to be treated. part of that, it’s probably about half of our kids came from some kind of unschooling or self-directed background. About half of our kids were found us in a variety of other ways. And part of treating kids the way they want to be treated, as we said, like most kids, most people don’t want to be told they have to go to bed.
So we’re going to have no bedtimes. And our kids are six to 16, something like that. we had this in New Jersey, we were running camp. Kids have to be supervised all the time during a camp program. And so we had the system where after we finished sort of the organized activities for the day that were, you know, choiceful and whatever, that kids could choose to go to what we call the after party. Tough name for a time where maybe kids might go to bed, but 40 kids showed up to the after party, which was in this like old rec center and it had like big bright fluorescent lights and a basketball court and it was awesome building and by 10 o’clock we had probably 30 kids 11 o’clock 30 kids still there and They have to be supervised so our staff can’t go to bed We don’t have like, you know not back to school camp It’s just teenagers and the staff can you know don’t have to stay up all night necessarily except for the one person
And we had one person who was signed up to stay up all night because we thought maybe the kids would go to bed. One o’clock in the morning, still half the kids are up. Two o’clock in the morning, half the kids are up. There’s six year olds still playing basketball at two o’clock in the morning. And this one kid is like, you know, looks like he’s his eyes are going to start bleeding because he’s so tired. But he like has the FOMO like a lot of people do on the first night of college. They do in one more shot. But instead, you know, he’s seven years old and there was no drinking involved in the making of this story. And
Blake Boles (56:14)
Thank you for that disclaimer.
Jack Schott (56:16)
And so at two o’clock in the morning, I pull Laura aside and I say, Laura, I think we gotta like put these kids to bed, you know? And we start talking about it. And we’re like, or stressed, because we made this promise that there would be no bedtimes. That’s what we told the families. That’s what we told the kids. There’s gonna be no bedtimes, because we’re trying to treat you the way you want to be treated. And she was like, yeah, we should put them to bed. Put them to bed. And if you’ve ever been with someone that’s more responsible than you, if you just wait a minute, they’ll do the responsible thing. So I just waited a minute and Laura walked over and called all the kids in and she said, Hey everybody, I made a mistake. We made a mistake. Like we said there’d be no bedtimes, but it’s two o’clock in the morning and our staff needs to sleep. And so we got to go to bed and all the kids, except for one, we’re basically like, yeah, of course we need to go to sleep. It’s two o’clock in the morning. Like, are you crazy? Let’s go to bed.
Blake Boles (57:13)
Yeah
Jack Schott (57:14)
And the teens went back to their cabin and they sort of hung out and, you know, stayed up later or whatever. And everybody else just like went back, went to bed and woke up the next day. And of course we were tired because we woke up at seven and started rocking and rolling for the day. But that moment of when we put our cards on the table and say, we’re on your team. Like we’re all in this together to try to help you get.
more of what you’re wanting. And sometimes we mess up too has been sort of the guiding light for me on so many of these like decisions to working with kids. It’s like, yeah, there’s like a lot of books and like whatever, but like at the end of the day, if I can earn your trust and then earnestly try to be helping you, then I’m going to mess up. And I’ll just tell you, was like, Hey, I messed up and I thought we could do this and turns out we can’t. you know, camp for me is a place where that is more possible in community than I’ve been able to find in other places for building, for bringing kids together. And so, you know, I probably won’t run any camp where I have no bedtimes for six year olds, but the learning was, was huge on, you know, mistakes are going to happen. And as long as I admit them,
Blake Boles (58:20)
Hmm.
Jack Schott (58:40)
and the stakes are pretty low, like whether or not you get a full night’s sleep or not, then we’re gonna be awesome.
Blake Boles (58:48)
Jack, where can people who are desperate to follow you online after that story find you and continue to hear from you?
Jack Schott (58:59)
You can go to jackschott.com. All the things are there, emails and all the other things on the internet.
Blake Boles (59:07)
Jack, as always, it’s a pleasure getting to chat with you. Thanks for coming on the podcast.
Jack Schott (59:12)
You the best Blake. Thank you.