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Money Stories · Episode 42

Nathan Barry: Redefining Wealth Through the Success of Others

For creators and founders whose self-worth is tied to their output.

Mike Brown with Nathan Barry, CEO of Kit · Jan 9, 2026 · 67 min

About this episode

Nathan Barry built ConvertKit, now Kit, into a nine figure company helping creators earn a living online. He tells Mike how a childhood moment of scarcity sparked a lifelong study of wealth, and why he treats making money as a skill.

He describes coming back from burnout and how his definition of wealth moved from security to freedom to helping others succeed.

Key takeaways

Full transcript

Automatic transcript, lightly corrected for names, with profanity masked. Some passages may contain transcription errors.

I was sitting at the top of the stairs, I the stairs, I was probably three or four 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 I 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 three 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. 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 a thousand little skills as well. I mean what an incredible skill to learn as an entrepreneur. You can compress time 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. When it comes to building wealth, how to spend money, what makes a rich like, I'm really excited for this conversation. 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 enough. Everyone wants to interview me about audience growth or, or things like that. It's like, I love those topics and they're in service of building wealth, but like, let's just go straight to the corner and let's talk about money it. I love it. On that note, let's start from the, and what are some of your earliest memories around money and how did those drive you to become successful?

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 three, four 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 not having have that was a pretty common thing of like being on the fringe of 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 imagine 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 the time in your life that you saw something happen and said that will never be me, right? And that points to fuel, which something that you talk about a lot in the inverse and

we can get to this much later in my life is what's time that you saw something happened and you said, oh, that could be me. 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 that there is an abundance around so that my future wife and I never fight about money. 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 Freed of making money as a skill. You know, he's 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 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, hey, it's like everything else that goes into this making money is made up of like a thousand little skills as well. We're talking discipline, sales, 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

and 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 a some very important skills of not only direct sales, but earlier than that, like a few are getting over a fear of rejection. And then when I started realize is like, oh, wait a second, I can all of these things that I'm doing, I, I'm stacking these a skills and that is going to lead the success, which just gave me even more drive to be like, wait, this is

in my control because everyone always said, you know, 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, they have an element of truth to them, if there is no truth in them, they wouldn't get but there's just an element of truth and they're things that people say because the 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. When you realize that all of 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. 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, it's 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 so you're surrounded by a world of that and generally, the more people are trying to pull you back 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 built over time. I had a very unique upbringing and it's something that shaped me to this day even and just like being 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. You know, my mom loves endurance sports. She became a certified personal trainer. So she, you know, like 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 4th of six kids. My parents couldn't give all of us like a lot of individual attention in school. So even in homeschooled. So they set an expectation early on the school is your responsibility. We're here to help you. We'll provide the curriculum and all of this, but like. It's not our fault if you get your school done and that's on you and that ended up being an incredible 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, was your school done No, you can't, you know, or even on the upside. I think that 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,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 sliding right now and I had the hardest time. I'm trying to do math and I want to be outside and my mom just said to me, you know, schools not a fixed number of hours it's a set amount of work. When you finish your work, you can go studying and it's up to you if this takes two hours of this takes six hours and you've never seen a more focused 11 year old like because I'm like, this

is the biggest unlock ever of like, wait a second, there's no speed limit like I set the, 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 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 a very unique upbringing that of me very well. Incredible skill to learn as an entrepreneur because most of us have to unwinded years of programming of this, you know, factory style education system, right?

And you got this gift early on of, and this is a funny saying kind of the opposite, but if you wait till the last minute and 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 in much bigger things with more impact than can you sledding this morning or not. My older siblings were really good at including me with their friend groups, so they were two years older and five years older than me and I just hung out with them and their friends and they did a great job of not treating me differently. I'm sure they were times they're like, you know, bringing a little brother along, but they were just great.

They were great about it. And so I just felt like, oh, this is me and my siblings siblings and my friends and it didn't I didn't realize that they were all like two to four 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 college and realize, oh, this doesn't matter so much is going to become very, very apparent. Oh, it matters a lot. And so I went to my mom and said, okay, I'm going to start high school

when we drive, you know, do an eight 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 have an older sibling sitting next to me. So every time I got stuck, I'd about, hey, how do you do this? Like this. And so I ended up, graduating high school a month before it turned 16 and then going to college and only ending up being basically a year, like six 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.

You know, and then also there is no speed limit. You set the pace. I don't want to be stereotypical here, but 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 of 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 it took a college algebra class and, you know, high school and in that class and she like told me to say these people would be like, how old are you?

And you're like, you look 15 or maybe 14. I don't know, but you're in a college class. So instead of answering, how old am I, I would say, yes. And they'd be like, okay, looks 15. There's college, so it's got to be 18. But 17 and you say good, yes. Cause like And they'd be like, okay, good guy. He's, he's 17. They'd, like, hey, this kid, he's here early. He's 17 and he's, you know, and, you. 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. 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, you graduate college, I assume early and now. Well, I dropped out after two years. Okay. So, Well, I was at college to learn in how to make money. And at the same time, I dated a girl in high school who like the amazing things came out of that relationship. One in particular, she taught me web design. She showed me how to write HTML and CSS like just the host those websites and Geo cities and I was like, this is amazing. So I got books from the library. I learned how to build websites, pirated copies of Photoshop

to be able to design. And so by the time, the time, I was 17. I was now basically two full. Years into my college experience I landed my first, $10,000 web design gig. And ended up getting to the point there's got a $10,000 gig and I called 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 to this other thing. So I I dropped out of a college at 17 before most people have have the chance to drop out of high school amazing.

Early, you know, 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, 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 is a wide wide range of things in there, but ultimately it was just, you know, thinking 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 seals. And probably the hardest time in there was the end of 2008.

All the local businesses and then I went on a trip with some friends in our church to South Africa and spent five weeks in South Africa like work to orphanage like got to experience all these go to all these amazing places and 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 because like January 2009, everyone was like, oh, this is not not good. And so that that was a tough time. 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 spent three years as a that software startup. What was it like going from working for yourself at a very young age now as a as someone who's employed gamefully 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 get I think they raised over over the course of that time like 32 million which in 2009 and 2011 in Boise, Idaho was like just an absurd amount of money. I remember hearing at one point that the burn was a million dollars a month and I was just like, what is even happening?

So yeah, from receipt to a lot of epic projects like an iPhone app in the app store the day the iPad it was released, you. 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. If you to bring in a like you're the average of the five 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.

Yeah, that's right. I haven't had a raise 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 I'm like, what is this? And so when the company went through layoffs and downsides and all of that 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 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, the bullpen where my computer like faced the whole room and moved to an office where my computer did not face the whole room and I decided that in two hours a day, I was going to just be as focused as possible

and be the best employee ever like two, three hours a day. Then I was going to use the other like four to five, four to six hours a day to learn how to program iPhone apps. You really get that that, which was like 10 gently related to my job, but not my job because I was like, look, I have to get my edge back. I have to get, you know, be able to focus. I got to be able to have drive and move quickly again. So it that sounds like this, this skill set that was in value proposition instilled by your parents of speed plus skill acquisition is really serving you well at this point. Oh, yeah. Yeah, it's serving me very, very well. And what was the turning point there?

When did you leave that company? I left in 2011. Shut down and I went back to freelance. So this time designing iPhone apps, I built a little bit of reputation from there. My wife and I got married two, three years earlier and our first son was born. I actually quit my job a week before he was born, which worked out really well. Like in hindsight, probably a stupid move, but I don't know. It worked out great. And, or at least a risky move. Yeah. And I just spent the next year doing freelance design and that went well.

Did you have any money saved up at this point or what was 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 the odd point was making to call it $1500 to $3,000 a month off of that and I just stockpiled all of that money. And so when I left my job, I had about $18,000 to $20,000 saved up and I had some level of my base lot like rent and more, I think rent was like 750 bucks 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, 30,000 a year or something like that. Like I'm actually preset like having that baseline. And so it went really well. Yeah. So the outside could have said, this is a huge risk, but you actually knew that it wasn't. Because both the combination of the money in the bank and the cash flow from products and like, wait, I 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 going to go well. Did you feel rich at that point?

Yeah, I felt 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 I applied to work at really the two main remote companies at that time you're automatic who made WordPress.com or makes WordPress.com. And then 37 signals makes base camp. And I put together these very elaborate like custom websites for like, you know, basically this like 37 signals will you hire me type thing. It was very. Design just for them. And then did one for automatic. Got an interview at automatic. Never got an interview at 37 signals.

So it didn't get either of those jobs. Though a fast forward a tiny bit. And the very first person to buy it. September 2012 exactly a year after I left my job was a designer at 37 signals.

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 want to Tim Ferriss was the one who's more theoretical. And Chris Gillibow was like very practical. Like this is what's right in front of me. And he was talking about like, look here's how he's got to make 80 grand a year, 100 grand a year. Writing and selling products online.

I didn't know that I could do that. But my idea was I wanted to get along 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 want to make money from it. So I had a goal of like, if I could make 10 grand. Over the lifetime of this book. How did that feel? I felt like I had unlocked the cheat code to.

Like, did 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 where we. We 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. 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 time freedom and I felt very, very rich. And how were you at this point? What an incredible unlock for a 22 year old kid.

I mean, it sounds like you cracked the code pretty early on, right? How did that lead into Kit and the rocket? Yeah. So I had, there's maybe two arcs. Well, first we'll start with the rocket ship ride. And then we can get into the, when the rocket crashed. 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, I'm excited about this idea. And that would last like maybe a weekend, maybe a week if I was like, he believed in it. And so from Chris Gillibault, 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 a thousand words a day, a thousand words a day is just two pages. So like, if you, if this is really important to you, like set it out right a thousand words as a software designer, I was like, well, first let me build an iPhone app to track the habit of writing a thousand words a day. And then let me do it. So I ended up like building up this 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 a thousand words a day. And the app popped up the next day and was like, you're gonna write a thousand words. I was like, no, the book is published. I'm done. Well, I can write in a blog post about how the book launch did and what I learned.

So I did that, that got some contraction. The app as it does popped up the next day and you know, said, you write a thousand words a day. I was like, what are you even right about? But I don't want to break an 81 day streak of writing a thousand 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 25,000 grand in the first day and $50,000 in the first month. Then was obsessed with with email marketing because that drove everything. And so then 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. Everything I was learning about marketing and

nouve , self-publishing and, publishing and so. I wrote, and selfom- I was three books and started a and started a SaaS company. All well building an audience. And I ended a building of the point the it the, why I got to 600 days in a row. of writing a thousand words a day and like transformed every aspect of my career. And how are we working at this point? Were you like all in hustle bro or did you have some semblance of lifestyle balance at this point? Yeah. I felt like I had lifestyle balance. 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 six, seven, sometimes occasionally eight hours. You know, and so like I would do the wake up right for two 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 right. Like this is not for you. But no, it wasn't an 80 hours a week grind in that way. But how so 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 feeling from the three books you've launched and that you've typed in and it gives you like a car or the machine. Or like infinite money or, or whatever. And I felt like I had discovered one of those. In, you audience and leverage and all that. So I was thrilled about, about that.

that one didn't work okay well let me let me figure that out and the last one there's money related 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 at your conferences and we all got each other there but my friends in Boise it was actually the most extreme when we were hanging with my wife's friends husband's and and because they were all $15, $20 an hour of jobs they were working on it so I just wouldn't talk about money with them at, at all because I I'm making 250 grand a year right and I like and so we

just get awkward now the thing the mistake that I made that on one hand those two worlds were almost always separate until they weren weren't and someone would be like I don't even have the book alone right 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 had this one do and I was like 32 you you know we're here like basically, we quoted someone's annual salary made in a day and that made some things awkward how do you deal with that isolation at that point make more friends on the internet

I I mean I started traveling more spending more time with the people who were doing stuff like this 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 on슷 and then trying to like bring up money the circumstances where it's like oh we don't actually know each other we don't we don't obviously you've been tremendously successful and and kit 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 like insanely productive talk talk about like, like, virtuous cycles and vicious cycles the virtuous cycle that I have from 2012 let's see, maybe the summer of 2012 to the summer of 2014 or spring 2014 was just 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 justn't just be totally sucked, in this world and so my wife

second son coming in he was born in May of 2014 and so I thought okay I'm gonna work hard the first three months of the year and I'm gonna try to make a new contractor on the remodel and then we had, our son was born and so I once he I basically said I'm a scale back and all the big new projects projects all of that and just keeps 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

you just like, cold or whatever else but now no one's

you know we're prescribing you two things antivirals take I really need those and they're like yeah we know we already called it in like okay kid we just figured we I could convince you we'll let you and so I ended the reason I didn't want the pain killers is

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 don't I don't want that like I need to perform and what ended up happening is I realized I need the pain killers just to survive and I got the point like I got 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 myself worth was tied into what I accomplished so when you ask like how to feel it felt amazing when I'm on the high of like accomplishing things that I never knew were possible of leverage and all this stuff in an amazing way like I felt

amazing but then when that was all gone and that that right there and then the virtuous cycle shifted in the razor edge to the vicious cycle and pointed spiral really fast and so even like three months later as I was trying to get off, pain killers and work, you know the and then I was getting to the point where I would sit down and try to write and the more I failed at doing the task in front of me the worst I felt myself which you know you talk about what type of fuel to use like that I didn't have there is no if you will left and that ended up starting a I mean it was

like 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 how do you just writing it 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 the emotions? Swirling like like can you just give us a sense? Yeah, I'm just partially sometimes like it 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 deal with like suicidal tendencies for a year and a half after that and like really work like my brother's in the house for like 12 years

just kind of gradually checking in somewhere in there I realized I started to make make the connection of the self-worth because at first you just like I don't function anymore what's happening like you can do better what you know you're just being yourself up so they've heard you say it's like entrepreneurs are is actually really I didn't come across this until years later but there's a reddit post titled no zero days and it's this an anonymous person on Reddit who just now writes up this post he's responding, someone who is depressed

who came function and all of that he writes up this great post and he's basically like 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, you know, that you like take the bar is no longer up here, it's not right 1000 words a day did you make make that sort of thing the other thing is I ended up finding a spark in building kit I had

a few friends really encouraged me to like either shut down that doesn't start go go all in and then my wife when I had the spark like maybe I could do this she was all about it and she was like yeah why don't you 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 this business and she goes okay let's say you do and it doesn't work out what's the worst thing that can happen and before I could answer she said we can sell the house that we bought and remodeled we can move it with my parents like we cut our expenses way down and that would be fine and I was like what you

the worst thing would happen is this would fail and I'd get a job you know but you're you're okay with like you know effectively financial ruin in pursuit of this goal and so I thought that was amazing 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 probably 4 years later was that she was like this is the first thing that I've seen you have a spark and been going towards in a long time and so like if this is like a little like this has even a chance of getting you out of this vicious cycle then like I'm all in 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 me 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 not one in the same you matter you belong and there's no like you matter because it's just like you matter that's the full sentence and you don't have to seek that validation and value in other things so how do you start to shift that how do you start to let go of finding value and external success I think that breaking that cycle

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 absolutely 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, but 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 more of that and it shifted in 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 ensuring that journey and I love that people other people are falling along but I think as I was building kit kit and making the tools for other people I had these sparks like people getting like running a launch on kit or achieving this goal with the tool that we the tool that we made or actually around that time people were using the book authority that I've written to like have their own launches which this is another thing about products that are fascinating and published this book on 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 drops 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

product that had sold 100,000 dollars based on following the play book you outland and authority and just started to be so much fuel around like wait it's an and I thought it was amazing that I the impact on my life but it's 10 times more fun to have the impact on I think I'm like planting the seed and then it coming back at the time that I needed it yeah I mean I often say that the day we become truly wealthy is the day we realize it's not about us and it sounds like that was a really pivotal realization in the in the growth of kit

but also your own personal journey yeah and it shifted I mean we ended up setting the mission of the company and we exist to help creators are living and that's just what we do that's how we measure success that is the drive of everything that we do and 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 like from other people Jimmy Carr is this one where he talks about how you know I'm rich when having more money money wouldn't change what I do day to day 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 locations and time is in there what are the two other categories that you would say minor freedom of mind and then freedom of soul freedom of mind 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 connected connected to a no greater purpose outside of myself yeah I love all of those I think it'll ultimately comes down to freedom but but I think the times that I felt the the wealthiest is when I'm having that impact on other people 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 where like kit has been I've loved everything

the product for the you built with kit like, what can I do it 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, so I can't attribute it it's the best debts like the most important debts cannot be paid back they can only be paid forward and those are my favorite where like like that's wealth to me is when you have impacted someone in a way that they can 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 and wealth building piggybacking off that what would you share around the topic of, of wealth building

well so I always think about making money is a skill and that being such an like it's a simple sense in a completely 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 and you do 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 on line and so okay we'll spend the next six months trying to master copywriting I can guarantee that

we'll play forward in in some incredible ways right audience building you know or might be like I'm very good at doing things manually but I understand automation and so you can say okay what project could I take what project could I take on that would help me learn those those skills in a practical way and get me closer and you can actually slim chance of success to a very

another defining concept of your life is flywheels how does skill stacking translate into flywheels yeah so 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 six to ten percent a year and that's how so much wealth is made so long as your loop closer in this flywheel is

re- investment 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 at all achieve this outcome I think of as this mini flywheel where I might hate working at it first but then the more I do it the more I learn how to do it the more I learn 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 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 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 last year I was playing volleyball one of my and I went up for a block and then personally on the other side I came 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 I had my health flywheel spinning quite well and I realized like I'm going to spend six weeks in a boot I like like I like this could be the end and like that whole flywheel could reverse and be a vicious cycle and so identifying that right now of like this is a big setback not catastrophic like I didn't break my leg or you know we're not nine months we're six to eight weeks out 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 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 it was like I gotta stay on top of this and so that's my approach to flywheels everywhere as I'm observing them seeing where they are running really well making note of that and then when I notice them start to slip, I take immediate drastic action. Yeah I mean so it sounds like preserving momentum at all costs. And as I think about the concept of a flywheel really it's a 3D representation of the compound interest. Yeah. It accelerates the more you invest and then continues to accelerate. And it starts out brutally slow to the point is unrecognizable right you think about compound interest

like I have a hundred bucks that I threw it in the stock market and you're like wait I have at the end of the year I have a hundred and five dollars like this is dumb why aren am I even the flywhele the same, where it starts out so so slowly that you're like like this sucks why don't I just go do, 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 yield from additional input accelerates. Right. And so what's the biggest problem is that people quit before they reach that that upward part of the curve or how

how do you think about that? Yeah, I think the first thing is they don't understand the difference between. Something that is effort based versus flywheel based. And so first they came to recognize the flywheel. The second thing is it once they can recognize that 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 this instant results. The flywheel is much harder to turn once it got going. The circular motion kept kept going. So people don't recognize it. 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. 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 webinar like affiliate webinar flywheel running and I was like cool that. 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 that happened and that negative and we went down to zero. Now I'm like tracking Am I off like is this continuing. Who is responsible for making sure that this continues

and making sure that I'm not jumping on the next thing too quickly. Because I mean to give you an idea of the. I guess the compounding nature when you have these things working. So first like choosing a business model. You know I went from selling design services to digital products to compounding that with an audience and in making hundreds of thousands of dollars a year. And now kid is at the point where I mean it's 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'ss compounding. And that's just that's a flywheel that's been running for in three weeks.

It'll be 13 years since I started the company. And so I guess that last mistake is you just don't run it for long enough. Yeah I mean this is such an interesting concept because I think it would be easy to look at what you've built as sort of that overnight success. You know I feel like there's probably not a lot of people out there that realize that kid is a 13 year old company and it wasn't always this way. So with your net worth compounding at this rate how do you think about translating that into a rich life now? Yeah I think the, the first thing is that I very clearly differentiate between paper wealth and liquid wealth

which is a really important thing. It the interesting trade off because there's times where you're like look the liquid in it. 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, all of that. But also you don't take it for granted and 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 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 the business again and all that. We're right about $400,000 a year and that gets us our farm, our, our nanny you know, the property next door to us you know but we've done a bunch of things to try to, to offset those costs or run it as a business in some ways and so I've, I 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. 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 that might be on a trip to Disneyland, we pay for the VIP tour guide and it's like, wait, you just dropped five grand on a day at Disneyland. , like yep, and it was worth every single penny or on the

to spend to spend on ridiculous like really, you can't just but not ridiculous in and I think, I think what you're talking about here is relativity and you know, based on your net worth and income, that's a relatively two weeks in place for myself, basically to say, oh, I have to spend 10%. On what feels like a splurge that I can't justify, because I would spend way too much

much time., I'm trying to justify, like, well, you know, if you think about it, if we added up all the, you know, business or economy tickets and it's really, you know, and all that stuff is like, no, no, no, this category just has to be spent. And then honestly, one of my favorite, it's created some great memories, like my wife's uncle who taught us how to sail. He was able to come on a trip with us. He's now in his mid seventies, 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 the condition of wealth is 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 fun. Yeah, I do some things different. You know, like, yeah, the life that I live in in almost every category is funded 100 times over, but. 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 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. And so I would I would do a lot more and you aviation is just category where you can spend an infinite amount of money There's always a bigger. Yeah, exactly. And so sure, if I had more liquid net worth, then I would be goofing off with

fancier planes, or using them more as a business tool, but I don't feel like that's holding me back in any way from impact. And that's what I would measure the wealth on. Nathan, thanks so much for coming on, sharing your wisdom, has been really an eye-opening conversation. For me, and just really the journey you've been on. Thanks. Thanks for sharing and being vulnerable. Yeah, thanks for having me. 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 as a happy kit customer, sign in for the newsletter if you're not signed up, delivered be a kit.

Where else can people find you, check 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. I have a newsletter, I love to write about money and then, kit.com. Yeah, cool man. Well, thanks for being here. Appreciate you. Thank Thanks for listening to this episode of Money Stories. I hope this conversation sparks something for you. If you're, if you're craving more conversations like this, I want to invite you to check out Unbreakable Wealth. It's a private community and coaching experience for founders, entrepreneurs, and executives who are ready to explore money meaning and what makes a rich life. If you're ready to rewrite your money story and lead a life on your own terms, apply now the link below.

More from Money Stories: all episodes. Mike’s book Be Rich Now covers the same ground in depth.