In this segment of the Money Stories interview, Nathan Barry expands on the metaphor of the "flywheel" to explain how virtuous cycles drive both personal health and financial wealth. He describes how a flywheel works—small, consistent inputs that eventually generate self‑reinforcing momentum—and how to spot when it stalls, using examples ranging from his workout routine to the growth of his company Kit. Barry shares personal anecdotes, such as breaking his ankle and the rapid compounding of his net worth, to illustrate the need for rapid, decisive action when a flywheel threatens to become a vicious cycle. He differentiates between paper wealth and liquid wealth, outlines his low‑cost‑of‑living strategy, and reveals a rule to spend 10 % of any windfall on a memorable experience. The conversation also touches on his passion for aviation, the limits of money in achieving impact, and practical advice for entrepreneurs on recognizing, building, and maintaining flywheels in business and life.
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I was sitting at the top of the stairs. I was probably 3, 4 years old, and I was listening to my parents fight about not having enough money. That scarcity actually causes real problems. People say money doesn't buy happiness. They're not acknowledging that the lack of money really causes a lot of strife. That's never going to be me. Nathan Barry is the CEO of Kit, where he has a front row seat to what's working in the most successful creator businesses. He's helped tens of thousands of creators earn a living online and is a strong believer in teaching everything you know, which he does weekly through his newsletter and podcast. Previously a designer, author, and blogger, he enjoys sports, woodworking, and spending time with his 3 boys. All of my self-worth was tied into what I could accomplish. It's real pain. I ended up going to counseling to deal with, like, suicidal tendencies for a year and a half after that.
How did those drive you to become successful?
I came across this idea of making money as a skill. Making money is just about luck. I was in the right place at the right time. All of these sayings that have an element of truth to them, but they're not true. They don't want to take on the full responsibility. Making money is made up of like 1,000 little skills as well.
I mean, what an incredible skill to learn as an entrepreneur. You can compress time, right? And output is not correlated to the number of hours. How did that feel?
I felt like I had unlocked the cheat code to everything. We're talking.
So what does wealth mean to you now? Welcome to Money Stories, where we have conversations with founders about money, meaning, and what makes a truly rich life today. I am joined by my dear friend Nathan Barry, founder of Kit, uh, email service provider for creators, uh, on a rocket ship ride to 9-figure ARR, and, uh, a really thoughtful guy when it comes to, um, building wealth, how to spend money, what, what makes a rich life. I'm really excited for this conversation. I, I think you have such a great philosophy. Welcome to the show, Nathan.
Thanks for having me on. This is my favorite topic ever. And so I don't get to talk about it enough. Everyone wants to interview me about audience growth or things like that. And it's like, I love those topics and they're in service of building wealth, but like, let's just go straight to the core and let's talk about money.
I love it. Well, on that note, let's start from the beginning. And what are some of your earliest memories around money and how did those drive you to become successful?
Okay. They're not super happy memories, which I think having done this show for a little while, you're not surprised by.
Yeah, this is, this is, this is not tremendously shocking.
Yeah, exactly. Wait, there's an entrepreneur that has a scarcity mindset around money and that drove success and it started at an early age? No. Anyway, so yes, that is, that is my experience. Earliest memory around money is I was sitting at the top of the stairs in our house and I was probably 3, 4 years old, and I could sit just like the fourth stair down from the top where I'm just out of view from anyone downstairs, but you can still hear really well. And I was listening to my parents fight about not having enough money. And that was a pretty common thing of like being on the fringe, the wall. Like, I was never in the middle of anything, but just watching, listening, noticing that, oh, there's not enough. And that's what comes from all of us, or that's— that scarcity actually causes real problems. Something that actually irritates me is when people say money doesn't buy happiness and just leave it at that, as like, oh, you know, money doesn't buy happiness. And I just think there's so much more to the story because they're not acknowledging that the lack of money really causes a lot of strife. And, you know, and it's not imagined, like, it's real pain. Yeah.
And so watching your, your parents fight, what did that leave you with?
Well, I think that some of the most important questions that you can ask is, what's a time in your life that you saw something happen and said, that will never be me, right? That points to fuel, which is something that you talk about a lot. In the inverse, and we can get to this much later in my life, is what's the time that you saw something happen and you said, oh, that could be me? And so I watched this happen, not when I was 2 or 3, but maybe when I was, um, 11, 12, and seeing the same stories play out in the same circumstances play out. And I was like, oh man, I don't know how, but that's never going to be me. I'm going to figure out how to get good at making money, how to make sure that I always have enough, uh, that there is an abundance around so that my future wife and I never fight about money.
And, and how does that drive you to become successful? How does your journey start to unfold from there?
Yeah, so I was always looking for ways to make money. Took me a while to understand like the physics of making money and all of these things. Somewhere high school, early college, I came across this idea first from Jason Fried of making money as a skill. You need to say, he talks about how you wouldn't expect to sit down at the piano with no experience and like play a concerto in the same way that you shouldn't expect to start a business and then just be like, oh yeah, and it magically worked. Like in the same way that piano is made up of reading music and music theory and the finger positions and every, like everything else that goes into this, making money is made up of like 1,000 little skills as well. We're talking discipline, sales, if we're doing business online, writing copy, processing credit cards, you know, filing for an LLC with the Secretary of State. Like these are all things that are very difficult skills when you do them for the first time and later on they become second nature. And so when I heard that mapped out from Jason, I realized like, oh, this is something that I can get really good at. And so some of those early examples of me trying to earn money, I realized, oh, I was building a skill then. I didn't know what to call it, but I didn't— I realized that when I was doing woodworking projects and then selling them door to door in our neighborhood, that was building some very important skills of not only direct sales, but earlier than that, like a fear, like getting over a fear of rejection. And then when I started realizing, it's like, oh, wait a second, I can— all of these things that I'm doing, I'm stacking these skills, and that is going to lead to success, which just gave me even more drive to be like, wait, this is in my control. Because everyone always said, you heard like, oh, phrases like, you know, making money is just about luck, I was in the right place at the right time, all of these things, or it takes money to make money. All of these sayings that have an element of truth to them. If there was no truth in them, they wouldn't get repeated. But they're not true. There's just an element of truth. And they're things that people say because they don't want to take on the full responsibility of what it means to master money, master wealth. And so they say things like, oh, it's about luck, or it takes money to make money, because it's some level of an excuse. And when you realize that all these things are, are a factor but not the whole story, then you have to take full accountability of it and you have to take a different approach. Um, and it's really hard to do when you're surrounded by a world that is constantly telling you like, oh, one, you shouldn't pursue this, it's wrong. You know, money is the root of all evil or whatever. Phrases get thrown out there.
A common money story.
A common money story, you know. So you're surrounded by a world of that, and then also this world where the more you succeed, generally the more people are trying to pull you back. Um, and so it's an incredibly difficult thing to overcome, but I think it's so important.
So was there a moment when you said, I'm all in, I'm taking full responsibility for my arc? When was that?
I don't think it was one moment. I think for me it it built over time. Um, I had a very unique upbringing, and it's something that shaped me to this day, even just like being, um, being homeschooled. So we grew up in the mountains outside of Boise. I'm the fourth of six kids, and my parents were very, very avid learners, so they're constantly reading. Um, you know, my mom loves endurance sports. She became a certified personal trainer. So she, you know, like, uh, my dad wanted to read and understand the Bible better, so he's like, let me learn like biblical Greek. You know, they're just like constantly learning and taking on new things and all of this. So on one hand, I had that environment. On the other, being the fourth of six kids, my parents couldn't give all of us like a lot of individual attention in school, so even being homeschooled. So they set an expectation early on of school is your responsibility. We're here to help you. We'll provide the curriculum and all this, but like, it's not our fault if whether or not you get your school done, that's on you. And that ended up being an incredible gift because they weren't in that like, you know, ride you till it's done. They're like, oh, well, the natural consequences. You wanted to watch the movie tonight? Like, well, is your school done? No, you can't, you know. Or even on the upside, I think that, um, in most school environments there is no benefit to being faster because the classroom moves at the pace of the slowest kid. And so I didn't have that experience at all. I remember being 11 or 12 and it's wintertime and it's snowing and it is the most perfect snow coming down. You know, the ones that the flakes are like the size of a quarter. You can like basically watch the snow accumulate. And I'm like, I just want to be outside sledding right now. And I had the hardest time. I was like, I'm trying to do math and I want to be outside. And my mom just said to me, you know, school's not a fixed number of hours, it's a set amount of work. When you finish your work You can go sledding and it's up to you if this takes 2 hours, if this takes 6 hours. And you've never seen a more focused 11-year-old, like, cause I'm like, this is the biggest unlock ever of like, wait a second, there's no speed limit. Like I set the pace. This is incredible. And so I, instead of like complaining and everything else that I would normally do that would burn hours of time, I was like, great, dialed in. Let's get this done. 90 minutes later. I'm enjoying the perfect snow. And that's how, uh, my parents really set the expectations. And so I've applied that all the way through. There's even a story of like how I applied it in high school. But, um, but yeah, a very unique upbringing that, that served me very well.
I mean, what an incredible skill to learn as an entrepreneur, because most of us have to unwind years of programming of, of this, you know, factory-style education system.
Right.
And you got this gift early on of, you know, and this is a funny saying, kind of in the opposite direction, but if you wait to the last minute, it only takes a minute. But you can compress time, right? And output is not correlated to the number of hours, which is what sets you up for success as an entrepreneur.
Yeah. And my parents actually even played that out in much bigger things with more impact than can you go sledding this morning or not? Um, my older siblings were really good at including me with their friend groups. So they were 2 years older and 5 years older than me, and I just, I hung out with them and their friends, and they did a great job of not treating me differently. I'm sure there were times they're like, you're bringing, you know, bringing a little brother along, but, but they were just, they were great about it. And so I just felt like, oh, this is me and my siblings and my friends, and it didn't I didn't realize that they were all like 2 to 4 years older than me until it was time everyone was getting ready for college. I was like, wait, I am about to start high school and they're all like juniors, you know, they're all thinking about where they're going to go to college. And I realized, oh, college is when I'm going to be left behind. And this is like, we're all homeschooled. It doesn't— the grade doesn't matter so much. It's going to become very, very apparent. Oh, it matters a lot. And so I went to my mom and said, okay, I'm gonna start high school soon. Is high school a set number of years or a set amount of work? And I was like, look, you have 3 older siblings, you know, 2 out of high school, one's in high school. Like, we've mapped out all the curriculum, uh, when you can graduate when the curriculum's done. And so I just said, amazing, you know, I'm really bored when we drive, you know, do an 8-hour road trip from Boise to Seattle every summer. To visit family. I'm also really bored when I do algebra. So like, why don't I just combine these two things? And I would do a month's worth of math lessons on the drive to Seattle. I had an older sibling sitting next to me, so every time I got stuck, I'd be like, hey, how, you know, how do you do this? And you're like, oh, like this. And so I ended up graduating high school, uh, a month before I turned 16, and then going to college and only ending up being basically a year, like 6 months to a year behind my friends who are much older than me. And it's all because my parents like truly lived out this idea of this is your responsibility, you know? And then also there is no speed limit. You set the pace.
I don't want to be stereotypical here, but, uh, I can imagine showing up as a 16-year-old kid on a college campus is, is quite shocking. To a kid that grew up homeschooled. How was that experience?
Well, so I had a friend who's a couple years older who she also went to college really early. I think she was 16 when she started going to college, and she told me, don't ever tell people how old you are. And I was like, okay, how do you avoid that? Because I was actually 15 when I took my first— I think I took a college algebra class, then, you know, while I was still in high school. And in that class, she like told me exactly what to say, because people would be like, how old are you? And they're looking at you like, you look 15, or maybe 14, I don't know, um, but you're in a college class. So instead of answering, how old am I, I would say, guess. And, uh, they'd be like, okay, he looks 15, this is college, so he's got to be 18, but 17? And you say, good guess. 'Cause like, it was legitimately, it was wrong. It was a good guess, but it was wrong. And they'd be like, oh, okay, good guess, he's 17. They'd be like, hey, this kid, he's here early, he's 17, and he's, you know, and you're like, I don't need to correct them. So there were definitely some things where like, some older friends like gave me some cues on how to navigate it or that sort of thing. But otherwise, I think going to college in, like my hometown, knowing enough people. It was a really good bridge into adulthood rather than like you now live in a dorm on the other side of the country and you're like thrown in the deep end.
Okay, so let's, let's fast forward. You graduate college, I assume early, and now—
Well, I dropped out after 2 years.
Okay, so, so what happens there?
Well, I was at college to learn how to make money. And at the same time, I dated a girl in high school who, like, the amazing things came outta that relationship. One in particular, she taught me web design. She showed me how to write HTML and CSS, like just the very basics, host those websites on GeoCities. And I was like, this is amazing. So I got books from the library. I like learned how to build websites, pirated copies of Photoshop to be able to design. And So by the time I was 17, I was now basically 2 full years into my college experience. I landed my first $10,000 web design gig. I'd worked my way up from the $200 projects to the $500 projects to the, you know, going all the way up from there and ended up getting to the point there's got a $10,000 gig. I called up my mom and said, look, I'm here to learn how to make money. I'm making money. Like, I think it's time for me to bounce and go do this other thing. So I dropped out of college at 17 before most people have the chance to drop outta high school.
Amazing. And now it's off to the races.
Yeah.
Were there tough times, uh, as you like, or, or did you start making money really early?
Uh, I started making money early. You know, I, I did this web design business with a couple of other friends. Including kind of an acquaintance who I learned some stuff from him, but it was like, ooh, you're more, you know, in the, in the arc between like business development and scam artist, you're like, you're somewhere on this spectrum, you know? So I learned, there's moments of learning what not to do. You know, there, there is a wide, wide range of things in there, but ultimately it was just, you know, if you think about making money as a skill, again, these basics of like, how do you close clients? How do you do contracts? you know, all of these things and, and just kept kind of stacking these up and compounding the skills. And probably the hardest time in there was the end of 2008. I had had a great year and like it really culminated in, um, an epic Q4 of like these web design jobs and all of that. And I was like, okay, this is really, really going well. You know, I'm closing deals with, uh, all the local businesses. And then I went on a trip, um, with some friends in our church to South Africa and spent 5 weeks in South Africa, like worked at an orphanage, like got to experience all these, go to all these amazing places and, uh, do some really cool service work and came back and all the, like, I had signed some of the contracts and others were proposals out And every single one of them said like, yeah, we're not spending money until our clients spend money. 'Cause like January 2009, everyone was like, oh, this is not, not good. And so that, that was a, a tough time. Uh, I ended up taking a job at the one client that was like, we've got work for you. And in fact, we'll take you on full time. And so I, I spent 3 years, uh, as a designer at that software startup.
What was it like going from working for yourself at a very young age now as a, you know, as someone who's employed, gainfully employed at a regular job?
Yeah, I, I learned a lot. They were still pretty entrepreneurial. The company was like 15 people when I joined. It was interesting watching them grow to 90 people, burn an incredible amount of venture capital. Like, I guess I think they raised over, over the course of that time, like $32 million. Which in 2009 to 2011 in Boise, Idaho was like just an absurd amount of money. I remember hearing at one point that the burn was $1 million a month and I was just like, what is even happening? So yeah, front row seat to a lot of, uh, epic projects like an iPhone app in the App Store the day, uh, the iPad was released, you know, being able to work on stuff like that. All the way through to like, there's a lot of bad decisions that I would not replicate. So I learned a lot in that. One of the biggest downsides was I actually lost my ability to work quickly. If we have a theme of there is no speed limit, you set the pace, uh, if you were to bring in a like, you're the average of the 5 people you surround yourself with, oh man, that like company environment where people aren't very driven, You lose your edge pretty quickly. And I remember a moment standing around the pool table where everyone was talking about how we didn't get paid enough. I was like, yeah, that's right. I haven't had a raise this whole time I've been here. Then I was like, wait a second, we're at the pool table right now. None of us are even working. We're all on salary. Like, what is this? And so when the company went through layoffs and downsized and all of that, um, and I still had my job. I realized that I'd lost my edge as far as coding quickly and all of that. And so, uh, there was an office that had opened up because the team had, you know, the team was now smaller than the office. So I moved out of like the bullpen where my computer like faced the whole room and moved to an office where, uh, my computer did not face the whole room. And I decided that in 2 hours a day, I was going to just be as focused as possible and be the best employee ever, like 2 to 3 hours a day. Then I was gonna use the other like 4 to 5, 4 to 6 hours a day to learn how to program iPhone apps and get really good at that, which was like tangentially related to my job, but not my job. Um, 'cause I was like, look, I have to get my edge back. I have to get, you know, be able to focus. I gotta be able to have drive and move quickly again.
Um, I mean, so it sounds like this, this skillset that was, uh, and, and value proposition instilled by your parents of speed plus skill acquisition is really serving you well at this point.
Oh yeah. Yeah. It served, served me very, very well.
And, uh, what was the turning point there? When did you leave that company?
I left in 2011. Um, I could see the company was like gonna fully shut down and, um, I went back to freelance. Uh, so this time designing iPhone apps, I'd built a little bit of reputation from there. Uh, my wife and I had gotten married 2, 3 years earlier and, uh, our first son was born. I actually quit my job a week before he was born. Um, which worked out really well. Like in hindsight, probably a stupid move, but I don't know, it worked out great. Um, and, uh, or at least a risky move. Um, yeah. And I, I just spent the next year doing freelance design and that went well.
Um, did you have any money saved up at this point or what was your financial situation like at that point?
Yeah, so the job I was making $63,000 a year. And I left my job in September 2011, and in maybe January, February of 2011, I had released an iPhone app myself that I learned on the side, built up, and got to the point where I was making $2,000— call it $1,500 to $3,000 a month off of that. And I just stockpiled all of that money. And so when I left my job, um, I had about $18,000 to $20,000. Saved up and I had some level of my baseline, like rent and more. I think rent was like $750 a month at the time or something like that, you know, for the little, little duplex. And so I was like, actually, I know I can cover the $60,000 a year in freelance. Then I've got this bit of product revenue that's another $20,000, $30,000 a year or something like that. Like I'm actually pretty set, like hammer that baseline. And so it, it went really well.
Yeah. So somebody on the outside could have said, this is, this is a huge risk, but you actually knew that it wasn't.
Yeah. Because both the, the combination of the money in the bank and, uh, the cash flow from products and like, wait, I have, I have multiple streams of income. I've got my active income from freelancing. I've got my semi-passive income from product revenue. Like, yeah, this is this is gonna go well.
Did you feel rich at that point?
Yeah, I, oh, I felt very, very rich. And the reason is because I had obtained location freedom, which is what I really wanted. So I really wanted to work at a remote company. I applied to work at really the, the two main remote companies at that time were Automattic, who made wordpress.com or makes wordpress.com, and then, uh, 37signals. Space Camp. And I put together these very elaborate, like, um, custom websites for, like, you know, basically this, like, 37signals will you hire me type thing. It was very elaborate design just for them. And they did one for Automattic. Uh, got an interview at Automattic, never, uh, got an interview at 37signals. So didn't get either of those jobs, though I then fast forward a tiny bit, um, the next year in 2012. So the goal for those jobs was to get a remote job so that I could travel, work remotely, all that. Didn't get those jobs, go out on my own, end up start starting to travel. So like by the time Oliver, our first kid, was a year old, he'd been to like 9 countries. Uh, we took him all around Europe, Costa Rica, Hawaii, road trip around the states, like we had a great time. Um, but then I ended up writing a book on how to design iPhone applications, and the very first person to buy it— so this is September 2012, exactly a year after I left my job— was a designer at 37signals. And I was like, wait, what? The company that I couldn't get a job at, the first person to buy the book. And I don't know if they needed the information or if they just wanted to support like an indie writer or whatever. Um, but it was just this wild thing of like them being the first ones to buy a copy of it.
What was the motivation for the book? Did you see this as the beginning of a larger platform? Like, was this fitting into a grand plan, or were you just throwing stuff against the wall at this point?
Yeah, so I followed people like Tim Ferriss and Chris Guillebeau. Um, Tim Ferriss was the one who was more theoretical, and Chris Guillebeau was like very practical, like, this what's right in front of me. And, um, and he was talking about like, look, here's how I got to the point where I was making $80 grand a year, $100 grand a year writing and selling products online. Um, I didn't know that I could do that, but my idea was I wanted to get a lot more clients for designing iPhone apps. And I thought that if I could do that, if I wrote the book on how to design iPhone apps, people would be more likely to hire me to design their apps. I did wanna make money from it, so I had a goal of like, okay, if I could make 10 grand over the lifetime of this book, that would be amazing. And I ended up launching it to an email list of 798 people, like a little pre-launch list that I'd built up and put together. And I made $12,000 in the first 24 hours, $19,000 at the end of the first week. And I never took on another design client.
How did that feel?
I felt like I had unlocked the cheat code to everything. Like, does everyone know this? Like, this is incredible that, you know, because now we're talking, we're talking skills, right? We've got audience, we have leverage, we're— we've, uh, built a product once and we've sold it, you know, hundreds of times without— like, there's no marginal cost of replication for this. Uh, I was just like, this is This is pure magic. And so leaving the job, I obtained location freedom. And then with this, I obtained complete time freedom and I felt very, very rich.
And how old were you at this point?
Uh, 22.
What an incredible unlock for a 22-year-old kid I mean, it sounds like you cracked the code, uh, pretty early on. And how did that lead into Kit and the, and the rocket ship ride?
Yeah, so I had— there's maybe two arcs. Well, first we'll start with the, the rocket ship ride, um, and then we can get into the, the, uh, when the rocket crashed. Um, when I decided I wanted to write a book, I had actually tried like multiple times before, but I was the fuel that I was using was just like motivation of like, oh, I'm excited about this idea. And that would last like maybe a weekend, maybe a week if I was like really believed in it. And so from Chris Guillebeau, he talked about how you can achieve all your writing goals and like do crazy things like write multiple books a year, all this stuff, blog posts, guest posts, everything. If you write 1,000 words a day, and 1,000 words a day is just 2 pages. So like if you, if this is really important to you, like set it out, write 1,000 words a day. I did kind of a random thing, like as a software designer, I was like, well, first let me build an iPhone app to track the habit of writing 1,000 words a day, right? And then let me do it. So I ended up like building up the streak and then kind of breaking it and building up again. But the point is, by the time I released my book, I had a streak of 80 days in a row of writing 1,000 words a day. And the app popped up the next day and was like, you're gonna write 1,000 words. I was like, no, the book is published. I'm done. Eh, well, I could write a blog post about how the book launch did and what I learned. So I did that. That got some good traction. The app, as it does, popped up the next day and, you know, said, are you gonna write 1,000 words today? I was like, I don't know what I even write about. Uh, but I don't wanna break an 81-day streak of writing 1,000 words a day. I guess I'll write another book. And so I wrote a book on designing web applications. So similar style, different, slightly different topic. 90 days later, published that, made $25 grand in the first day and $50,000 in the first month. Then was obsessed with email marketing, cuz that drove everything. And so then I, I ended up starting ConvertKit, which became Kit. And then I kept the writing streak going and I wrote and published another book called Authority about the whole, everything I was learning about marketing and self-publishing and everything like that. And so in this like one year period, I wrote and self-published 3 books and started a SaaS company, all while building an audience. And I ended up building up to the point where I, I got to 600 days in a row of writing 1,000 words a day and like transformed every aspect of my career.
And how hard were you working at this point? Were you like all-in hustle bro, or did you have some semblance of lifestyle balance at this point?
Yeah, um, I felt like I had lifestyle balance. Yeah, I had a young kid and yeah, I had time freedom. I sleep less than— my wife loves sleep. I'm like, sleep is great, you know, you get your 6, 7, sometimes occasionally 8 hours, you know? And so like I would do the wake up right for 2 hours before anyone else wakes up. But like, I view that as the, if you're working on something that you believe in, that level of drive is just like the, the admissions ticket. You know, if you're not willing to do that, like go get a job, don't get on the ride. Like this is not for you. But no, it wasn't an 80 hours a week, uh, grind in that way. But I also just loved it. Like, it's so much fun to create.
Yeah. And I wonder, you know, how was the kid who said, I'm never going to be that— how are you, how are you feeling from that lens at this point? You've launched these 3 books, you've launched a SaaS company, You're off to the races. You've achieved time and location freedom.
Probably feeling a range of things. I mean, let me try to remember. On one hand, like I've achieved everything I've set out to, and I figured, you know, like I, uh, loved playing computer games as a kid and like Age of Empires and some of these other, other games. And there's these cheat codes that you type in and it gives you like a car with a machine gun on it, you know, and, or like infinite money or whatever. And I felt like I had discovered one of those cheat codes. In, you know, an audience and leverage and all of that. So I was thrilled about that. Um, the SaaS company did not take off, and so I was pretty bummed about that side of it, you know, like how I sort of had this like Midas touch a couple times in a row, like, oh, that worked, and then this worked, and then that one didn't work. Okay, well, let me, let me figure that out. And the last one that was money related is, um, I had a lot fewer friends that I could relate to because I was starting to form my new group of friends who were all online, who I would see twice a year at conferences, and we all got each other. But my friends in Boise, it was actually the most, um, extreme when we were— when I would hang out with my wife's friends' husbands. And because they were all $15, $20 an hour, um, jobs that they were working all that. So I just wouldn't talk about money with them at all, because now I'm making $250 grand a year, right? And like, and so it would just get awkward. Now the thing, the mistake that I made that on one hand served me incredibly well, on the other hand made for some awkward conversations, is I blogged publicly about all the numbers. And so those two worlds were almost always separate until they weren't. And someone would be like, oh, Nathan, how'd the book launch go? Right? Where, where I, and I'd be like, oh, it went really well. Happy about it. So did you, the last one you did $25 grand on in a day, how'd this one do? And I was like, $32,000. You know, where you're like, basically we quoted someone's annual salary made in a day and that made some things awkward. And, uh, it. On a local level, it was isolating.
Yeah. How do you deal with that isolation at that point?
Make more friends on the internet. That's— I mean, I, I started traveling more, spending more time with, uh, the people who are doing stuff like this, um, and ended up making some more friends locally who thought in a similar way. But yeah, so I ended up like basically going deeper with the friends that I always had that just didn't treat me differently based on that. And then trying to avoid bringing up money in the circumstances where it's like, oh, we don't actually know each other. We don't, we don't need to go there.
Obviously, you've been tremendously successful and Kit has, has now grown into a world-class company. And I know that there are some tough times behind the scenes. Can you share a little bit about some of the harder times?
Yeah, well, my insanely productive, um, talk about like virtuous cycles and vicious cycles. Uh, the virtuous cycle that I was running from 2012, let's see, maybe summer of 2012 to summer of 2014, uh, or spring of 2014 was just unstoppable. Like, we're compounding on a level, like, it was amazing. New products, the audience is growing, all of that. And I thought, okay, I want to do things offline as well. I don't want to just be totally sucked into this world. And so my wife and I had our second son, uh, coming in. He was born in May of 2014. And so I thought, okay, I'm gonna work really, really hard the first 3 months of the year. And I'm gonna try to make $50 grand a month each of those months. I pulled that off January, February, March, and then we had bought a house, we were remodeling it. I decided to be the general contractor on the remodel, um, and then we had, uh, our son was born. And so I, once he— I basically said I'm gonna scale back on all the big new projects, all that. I'm just gonna keep the writing goal going. Because now the streak is at 600 days in a row. And I— it went really well for the first 2 weeks, uh, after he was born. And then, you know, our, our 2-week-old got sick and our 2-year-old got sick, just like colds or whatever else. But like, now no one's sleeping. My wife is still recovering, and I tried to like step up and like take on everything because also like I didn't really need to be working I just needed my 90 minutes to write my 1,000 words, uh, and that was it. And it actually got to the point where, uh, one day I noticed this rash on my leg, and I remember asking Hillary, like, are you using the same laundry detergent? Like, has any— I don't know what, like, this allergic reaction or whatever. And I texted my brother, who's a physician's assistant, and I was like, I have this rash on my leg, do you know anything about it? He's like, Well, does it follow a dermatological distribution? I was like, Daniel, I have no idea what that means. He's like, Google it. Basically means, does it follow the pattern of your nerves? And I was like, yeah, it does. He's like, yeah, you have shingles. Go to the doctor. And I was like, I'm 20. I'm not even 24. I'm about to turn 24. Uh, how do I have shingles? So I go to the doctor and they're like, you know, describe your life, what's going on, and describe like remodeling a house, two kids, you know, all this stuff. And they're like, yeah, you're just absurdly stressed. And, uh, your body is like, had enough and, you know, gave you shingles. And I remember them saying, you know, we're prescribing you two things: antivirals to take care of the shingles and painkillers. And, um, and there were some pretty serious painkillers. And so I was like, take the antivirals, pass on the painkillers. And they're like, are you sure you're really gonna want them? I'm like, it's like an itchy, it's annoying, but like, it's fine. I'm like, okay, you know, we're not gonna force you to take drugs. And that was at like 10 in the morning. At like 2:30 in the afternoon, I was calling them back. I was like, actually, I, I really need those. And they're like, yeah, we know, we already called it in. Like, okay kid, we just figured we're not gonna convince you, we'll let you. Um, and so I ended up taking, you know, like the reason I didn't want the painkillers is because, uh, when I was a kid I broke my leg and so I knew what that you know, the hydrocodone, the— like, I knew what it felt like, the brain fog and all that. I was like, I don't, I don't want that. Like, I need to, I need to perform. And what ended up happening is I realized I needed the painkillers just to survive. And I got to the, the point, like, I got all of the brain fog, everything else, and I completely lost my ability to be productive. And what I realized— took me a long time to realize— but I realized that all of my self-worth was tied into what I could accomplish. So when you ask like, how'd it feel? It felt amazing when I'm on the high of like accomplishing things that I never knew were possible, leverage and all this stuff in an amazing way. Like, I felt amazing. But then when that was all gone and that, that virtuous cycle shifted the— in the razor edge to the vicious cycle, Then boy, did it spiral really, really fast. And so even like 3 months later, as I was trying to get off, uh, painkillers and working out, you know, then I was getting to the point where, um, I would sit down and try to write even something as simple. You know, I did this for 600 days in a row. I'd sit down and try to write and I couldn't think, I couldn't figure out what to write. And the more I failed at doing the task in front of me, the worse I felt about myself, which, you know, Uh, you talk about what type of fuel to use, like that I didn't have, there was no fuel left. Uh, and that ended up starting a, uh, I mean, it was like a, it was a multi-year battle with depression.
So it sounds like the thing, the very thing that made you successful, this writing habit, now became a prison of sorts, right? A way to beat yourself up for, for not being productive.
It wasn't just writing it, but I mean, it was everything. I just didn't. I would sit down at the computer and then find myself staring at the wall and realize that like an hour had gone by and I like just couldn't, couldn't get anything done.
And so going from this very young kid making a ton of money, high highs, into this spiral, like, like what is that like? What were, what were the emotions swirling? Like, like can you just give us a sense?
Yeah, I mean, it's partially sometimes like a kind of out-of-body experience of like just, yeah, going through like numb. But then also, I mean, I, I ended up going to counseling to deal with like suicidal tendencies for a year and a half after that. And like really working through, um, like I, uh, my two older brothers are in the Army. Uh, and so when they came back from Iraq and Afghanistan, we would— it was one thing that we did together is we would take like shooting classes and all of this. So we'd do lots of stuff with guns. Uh, like at, at the time I was very proficient with firearms and all of that. I have not owned a— I guess technically I still own two firearms. Uh, they just haven't been in my house for like 12 years, right? Like they've been at my brother-in-law's house for a very long time cuz for— I would not trust myself. During that time with, uh, any method of, of, uh, easy suicide.
How do you pull yourself out of that?
Uh, one of my really good friends, uh, she's actually now my sister-in-law, um, ended up, uh, like really reaching out, making a recommendation for a counselor, like just kind of gradually checking in. Um, Somewhere in there I realized, I started to make the connection of the self-worth. Because at first you're just like, what's going on? Like, I don't function anymore, what's happening? Like, you can do better. Like, you know, you're just beating yourself up. So then I've heard you say is like, entrepreneurs are really good at beating themselves up. And like, yep, 10 out of 10 on that one. Um, and so once I started to notice the pattern celebrate even the tiniest wins. Um, I didn't come across this until years later, but there's a Reddit post, uh, titled, um, No Zero Days, and it's this anonymous person on Reddit who just writes up this post. He's responding to someone who is depressed, who can't even function and all of that. He writes up this great post and he's basically like, your only goal is to not have a zero day. Meaning you just need to do one thing that your future self would thank you for. And that might be, uh, you know, that you like take care of yourself in some way or do this tiny little thing. Like basically we're not— like the bar is no longer up here. It's not write 1,000 words a day, did you make $50 grand this month or whatever. It's like, did you just accomplish this little thing and like stack these tiny, tiny gains? Um, it's like, for me to be anything, move the business forward, uh, that sort of thing. The other thing is I ended up finding a spark in, um, uh, building Kit. I had a few friends really encourage me to like either shut down that business or go all in. And then my wife, when I had the spark, like, maybe I could do this, uh, she was all about it. She was like, yeah, why don't you, um, you know, why don't you really pursue this? Now there's two versions of that actually, that one that I only learned like a few years later. The story that I remembered and that I told was when I said like, okay, I need to— I think I need to double down on this business. And she goes, okay, let's say you do and it doesn't work out, what's the worst thing that could happen? And before I could answer, she said, we could sell the house that we bought and remodeled, we can move in a boat with my parents, like we cut our expenses way down and that would be fine. And I was like, what? No, the worst thing would happen is this would fail and I'd get a job, you know. But wait, you're okay with like, you know, effectively financial ruin in pursuit of this goal? And so I thought that was amazing and I was like, okay, great, like I have full support, let's go. And all of that was true. The layer on top of it that I didn't know and that I didn't learn probably till 4 years later, was that she was like, this is the first thing that I've seen you have a spark towards in a long time. And so like, if this is like a little— like, if this has even a chance of getting you out of this vicious cycle, then like, I'm all in. Let's, let's do it.
So did she know the depths of your pain at that, at that time?
I think so, yeah.
And Looking back at that period of your life, what would you go back and tell that version of yourself now?
You are not what you accomplish. Those two things, they're both true, they both exist, but they're, they're not one in the same. Um, you matter, you belong, and there's no like, you matter because— it's just like, you matter. That's the full sentence. Um, and then you don't have to seek that, uh, validation and, uh, value in other things.
So how do you start to shift that? How do you start to let go of finding value in external success?
I think that breaking that, that cycle, um, was one part of it. Part of it was just like even an intellectual understanding of like, oh wow, this is not, this is not serving me. Or like, this served me very well until it, until it was my absolute downfall. But the other thing is realizing that I love the teaching side of it, of what I was doing, of talking about going back to making money as a skill. And like, I've discovered all of these things that are amazing and I want to share them with other people. And why don't I do more of that? And it shifted from being about me to being about them, in the sense that I was always teaching and sharing along the way because I'm just like, I felt like I had discovered the most incredible things. Like, do you know about this? Do you know about this? You know, sharing that journey. And I love that people, other people were following along. But I think as I was building Kit Um, and making the tools for other people. I, I had these sparks of like people getting like running a launch on Kit or achieving this goal with the tool that we made. Or actually around that time, people were using the book Authority that I'd written to like have their own launches, which this is another thing about products that are fascinating. Like I had a, my, the peak of my success and all of this, and I'd published this book on, uh, self-publishing and how to build an audience and all of that. And people had bought it and loved it. But now I'm like in this troughs of despair. And as I'm coming up out of this is when people start publishing their books that they had done based on the playbooks that I had built out. And I started to realize like, I, I started to see the things that I intellectually knew this will work for other people. I started to have them coming back to the story of like, Nathan, I followed exactly what you said and I made $5,000 off of it and this is what it means for me. Or, you know, I remember Adam Wathan, who is this incredible, uh, designer and engineer who actually created the— now he's created the CSS framework Tailwind, which is used by every single AI product out there. Like, it is, it has taken over all, like, everything. But he was like, look, I, I made this product that had sold $100,000 based on following, you know, the playbook you outline in Authority. And you started to have these stories stacking up, and it started to be so much fuel around like, wait, it's an impact on other people. And I thought it was amazing when I had the impact on my life, but it's 10 times more fun to have the impact on other people. And I think I'm maybe only just now in this conversation realizing the timing of like planting the seed and then it coming back at the time that I needed it the most.
Yeah. I mean, I often say that the day we become truly wealthy is the day we realize it's not about us.
Yeah.
And it sounds like that was a really pivotal realization in, in the, in the growth of Kit, but also your own personal journey.
Yeah. And it, it shifted. I mean, we ended up setting the mission of the company of we exist to help creators earn a living. And that's just what we do. That's how we measure our success. That is the drive of everything that we do. And it's, yeah, it's been very powerful.
So what does wealth mean to you now?
I don't think I have a tight definition of it. There's other definitions that I like from other people. Uh, Jimmy Carr has this one where he talks about how, you know, I'm rich when having more money wouldn't change what I do day to day. Um, I go to these categories, and I've heard you talk about this as well, of, you know, we're talking about freedom in these different categories. So far we've touched on like money and, uh, location, and time is in there. What are the two other categories that You would say mine are freedom of mind and then freedom of soul. Freedom of mind, freedom of soul.
Freedom of mind being my own internal experience, free of anxiety, free of depression, you know, open to new ideas. And then freedom of soul is connectedness to a greater purpose outside of myself.
Yeah, I love all of those. I think it ultimately comes down to freedom. Um, but I think the times that I felt the wealthiest is when I'm having that impact on other people. Um, there have been a few times when someone has said, you know, this thing that you did was really impactful, how can I pay you back? You know, or like Kit has been— I've loved everything, the product you built with Kit, like what can I do for you? And I'm like, just take it and go do something meaningful with it. There's a line that I don't know who it's from, uh, so I can't attribute it. Just the best debts like the most important debts cannot be paid back. They can only be paid forward. And those are my favorite where you're like, like, that's wealth to me is when you have impacted someone in a way that they could never pay back, but they could absolutely pay forward.
I love that definition. And I know you spend a lot of time thinking about personal finance and wealth building. Piggybacking off of that, what would you share around the topic of wealth building?
Well, so I always think about making money as a skill and that being such an un— like, it's a simple sentence in a completely different mindset shift. So the thing that's made the biggest difference for me is getting clear on where I'm trying to go and then realizing or breaking down what skills I need to achieve in order to get there. So if you want to copy that period of my journey where we're, uh, selling digital products, you know, building an audience, all of that, well, we can break down the skills you need to have in order to do that. Maybe you understand sales, but you don't understand sales online. And so, okay, we'll spend the next 6 months trying to master copywriting. And I can guarantee that will play forward in, in some incredible ways, right? Audience building, you know, or it might be like, oh, I'm very good at doing things manually, but I don't understand automation. And so you can say, okay, what project could I take on? Who's first? What skills do I need to learn to close this gap to go where I'm trying to go? Second, what project could I take on that would help me learn those skills in a practical way and get me closer? And you can actually systematically break down. All of these things and get to the point where you're like, whoa, I have all of the skills that I need to achieve any of these outcomes. And it's not to say that once you have the skills, success is guaranteed, but you can go from a, a slim chance of success to a very, very high likelihood of success if you're willing, you know, if you break it down the skills and you learn them systematically. And that has been just a defining principle of my life. And it's really changed, reframed everything from it being about luck to skill and execution.
And another defining concept of your life is flywheels. How does skill stacking translate into flywheels?
Yeah, so, you know, we talked earlier about like virtuous cycles and vicious cycles, and a flywheel is just a virtuous cycle. And so it's anything in life that The more this thing happens, the more likely it is to continue happening. And so if we think about investing in those terms, if we are making money and reinvesting it to, or investing it to buy assets and companies that spit off dividends and cash and resources, and then we use that to buy more and companies like this is a flywheel that compounds very, very well. You know, at this like 6 to 10% a year, and that's how so much wealth is made. So long as your loop closer in this flywheel is reinvestment and not lifestyle inflation or spending more money, right? And so I look for flywheels everywhere. I'm basically saying, how can I take this thing and make it so that the more this happens, the more it will continue to happen. And so like working out, for example, I don't think of as if I work out, I'll achieve this outcome. I think of it as this mini flywheel where I might hate working out at first, but then the more I do it, the more I learn how to do it, the more I learn how to do it, the more I enjoy it, the more I enjoy it, the more I want to do it. And it becomes this self-reinforcing flywheel. And if you look for these flywheels are absolutely everywhere. And then the other key, since we've talked about the vicious cycles, is if you watch that closely, you can identify the signs of a flywheel stalling out. And then it becomes, oh, it's not just that I missed a workout or something else. It's like, oh, this could be the end of something really, really good. And I need to watch that carefully. And I need to get to this point where I am going to put in an extra amount of effort in order to make this happen. And that, that could be money related. That could be wealth related. Uh, um, you know, money, time, relationships would be a huge one, you know, between you and your spouse. You're like, oh, that was not a good— like, that was just a step backwards that just happened. Let me put in an outsized amount of effort to repair that so that we continue in this compounding cycle. Um, last year I was playing volleyball. One of my favorite things to do. And I went up for a block and the person on the other side came under the net. I came down on them as they like took out my leg and I broke my ankle. And this is at a point where I had my health flywheel spinning quite well. And I realized like, I'm going to spend 6 weeks in a boot. I like, this could be the end, you know, like that whole flywheel could reverse and be a vicious cycle. And so identifying that right now of like, ooh, this is a big setback. Not catastrophic. Like I didn't break my leg or, you know, we're not 9 months, we're 6 to 8 weeks, uh, you know, out of this and I gotta work my way back. But I realized like, okay, now the most important thing that I can do is to make sure that I don't turn this virtuous cycle into a vicious cycle. So I actually started going to the gym an extra day a week, even though I couldn't do half the exercises that I was doing because I was like, I gotta stay on top of this. And so that's my approach to flywheels everywhere is I'm observing them, seeing where they are running really well, making note of that. And then when I noticed them start to slip, I take immediate drastic action.
Yeah. I mean, so it sounds like preserving momentum at all costs. Yes. And, and as I think about the concept of a flywheel, really it's a It's a 3D representation of a compound interest curve.
Yes. Yes. Right.
It accelerates the more you invest and then continues to accelerate.
Um, and it starts out brutally slow to the point it is unrecognizable, right? You think about compound interest, you're like, I have $100. I threw it in the stock market. And you're like, wait, I have at the end of the year, I have $105. Like, this is dumb. Why am I even doing this? You know, the flywheel is the same way where it starts out so slowly that you're like, this sucks. Why don't I just go do it the manual scrappy hand pump way? But it's the compounding over time. Yeah.
And at some point that, that curve starts to turn hyperbolic where that, that flywheel in the 3D starts to spin faster and, and then the, the yield from additional input accelerates.
Right.
And so what, what's the biggest problem? Is it that people quit before they reach that, that upward part of the curve? Or, or how do you think about that?
Yeah, I think the first thing is they don't understand, uh, the difference between something that is effort-based versus flywheel-based. And so first they can't even recognize the flywheel. The second thing is it, once they can recognize it, they don't understand the amount of effort that it takes to get a flywheel going. Versus like a much more manual process. Because if you think about the physics of a flywheel, it's actually much harder to do. Like I have installed a flywheel on a well in South Africa and like the hand pump version would have gotten us instant results. The flywheel is much harder to turn, but once it got going, the circular motion kept, kept going. So people don't recognize it. Uh, they either aren't willing or get discouraged to put in the work. To make it happen. And then probably the third thing they do is they fail to recognize the ongoing effort. Like at some point it gets easy and they take it for granted. I did this with Kit at one point where we had the most beautiful, uh, webinar, like affiliate webinar flywheel running. And I was like, cool, that's working great. Now I'm going to go over here. And it like slowly slowed down and stopped and I didn't notice. I didn't have the accountability in place and, and all of that. And so I came back and I was like, what happened? Like, this is at a standstill. It's like, yeah, well, we kind of worked on these other things and this negative thing happened and that negative, and we went down to zero. Now I'm like tracking, you know, am I off, off track? Like, is this continuing? Who is responsible for making sure that this continues? Um, and making sure that I'm not jumping on the next thing, uh, too quickly. Because I mean, to give you an idea of the, I guess, the compounding nature of wealth, like when you have these things working. So first, like choosing a business model, you know, I, I went from selling design services to digital products to compounding that with an audience and on from there, uh, and making hundreds of thousands of dollars a year. And now Kit is at the point where I mean, it's growing my net worth by hundreds of thousands of dollars a day because of the value of the software company and how it's valued in the market and how it's compounding. And that's just, that's a flywheel that's been running for, uh, in 3 weeks it'll be 13 years, uh, since I started the company. And so I guess that last mistake is, is, uh, you just don't run it for long enough. Enough.
Yeah, I mean, this is a— is such an interesting concept, um, because I think, you know, it would be easy to look at what you've built as sort of that overnight success. You know, I, I, I feel like there's probably not a lot of people out there that realize that Kit is a 13-year-old company, right? You know, and, and it wasn't always this way. So with your net worth compounding at, at this rate, how do you think about translating that into a a rich life now?
Yeah, I think the, the first thing is I, I very clearly differentiate between paper wealth and, and liquid wealth, which is a really important thing. It's an interesting trade-off because there's times where you're like, look, the liquid wealth is this amount. Should I splurge a portion of this to create, um, an experience now? And it's— I, so I don't ignore the paper value. Because there's an element of, of realness to that. Like, it will spit off cash flow, like, um, all of that. But also, you don't take it for granted. It's just walking that line. I like to create a— I like to have a relatively low cost of living. And so even I was running the numbers, um, you know, we'll see if this is low or high to other people. But I ran the numbers on our life in Boise and it costs, outside of business income, like what's offset by business and all that, we're right about $400,000 a year. And that gets us our farm, uh, our, our nanny, you know, um, uh, a property next door to us, you know. But we've done a bunch of things to try to offset those costs or run it as a business in some ways and, um, So I've, I've really designed it in a way that I'm like, okay, I feel like I can splurge and do these big things, and also I'm still just not spending that much money relative to income and net worth. Um, and then I also have a rule that whenever I have like a big windfall come in or something else, I have to spend 10% of it on something that I think is really, really fun. And, um, that might be on a trip to Disneyland. We pay for the VIP tour guide and it's like, wait, you just dropped $5 grand on a day at Disneyland? It's like, yep. And it was worth every single penny. Or on the extreme, like we sold a little bit of Kitstock. Um, I sold 1.25% of the company 4 years ago, uh, for $2.5 million. And I was like, okay. What are we, you know, we chartered a private jet to, uh, uh, to the British Virgin Islands and went sailing for a week with, uh, with our friends. And I was like, you know, that was over $100 grand spent on one thing. And I was like, yeah, but that, you know, that was my way of forcing myself to spend some amount of money on an experience that otherwise I would say is ridiculous. Like, really, you can't just take the Delta flight, you know.
Yeah, but not ridiculous in context, right? And I think, I think what you're talking about here is, is relativity. And, you know, based on your net worth and income, that's a relatively small amount, right?
Yeah. And I, so I put some of these rules in place for myself basically to say, oh, I have to spend 10% on what feels like a splurge that I can't justify. Justify, because I would spend way too much time trying to justify. Like, well, you know, if you think about it, if we added up all the, you know, business or like economy tickets, and it's really, you know, and all that stuff is like, no, no, this category, um, just has to be spent. And then honestly, one of my favorite, uh, it's created some great memories. Like, my wife's uncle who taught us how to sail, uh, he was able to come on a trip with us. He's now in his mid-70s, you know, and so we're on this private jet and I'm sitting at the back of the plane and seeing like these conversations throughout the plane happening and just seeing people laugh and have fun and all this. And like, oh, I got to use money as a tool to create this experience. Um, watching my wife and her brother have this great conversation and, you know, all this stuff happened. I'm like, oh, this worth every penny.
So if your definition of wealth is enough money, if another dollar means you wouldn't do anything different, would you say you're there?
I wouldn't do anything different on the things that I think truly matter. On the things that are just a hell of a lot of fun, yeah, I'd do some things different. Um, you know, like, yeah, the, the life that I live in almost every category is funded 100 times over. But then you get into airplanes.
Yeah.
And that's the thing, you know, I, I own a small plane, I got my pilot's license, um, and I, I love flying it. You know, it's like that and sports are the things that get me into like this kind of like flow state. Um, and so I would, I would do a lot more of those. And you— aviation is just a category where spend an infinite amount of money.
There's always a bigger jet, as they say.
Yeah, exactly. And so, uh, sure, if I had more liquid net worth, then I would be goofing off with, uh, uh, fancier planes, um, or using them more as a, as a business tool. But I don't feel like that's holding me back in any way from impact, uh, and that's what I would measure the wealth on.
Nathan, thanks so much for coming on, sharing your wisdom. This has been, uh, uh, really an eye-opening conversation for me and, uh, and just really the journey you've been on. Thanks, thanks for sharing and, and being vulnerable.
Yeah, thanks for having me. I— it's my favorite topic ever. I think that when people take wealth seriously in all aspects, then they can have not only a big impact on their own life but everyone around them. So it's important work that you're doing.
Yeah, thanks, man. And, um, as a happy KITT customer, sign up for the newsletter if you're not signed up, delivered via KITT. Where else can people find you, check you out, what you're working on?
Yeah, I'm just Nathan Barry, and Barry's B-A-R-R-Y on all socials, NathanBarry.com. I have a newsletter. I love to write about money. And then KITT.com. Yeah.
Cool, man. Well, thanks for being here. Appreciate you.
Thank you.
