How Writing Online Will Make You A Millionaire - Nathan Barry (Founder of Convertkit)
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This week's episode is with Nathan Barry, who's the founder and CEO of ConvertKit,

a software company valued at over $100 million. And Nathan's story is absolutely fantastic. He started off working a normal job, realized he didn't particularly enjoy his normal job, taught himself to do design and code type stuff, and started building apps for the iPhone app store. And then later on, he transitioned away from that to build his software business. I had these three posters on my wall in like my first real home office. And there were three mantras of create every day, teach everything you know, and work in public. And that was like my equivalent of...

of show your work. I guess the way to put it is it is simple, but not easy. And so if you get clear with yourself that like, okay, I'm setting out to do something that is in fact very difficult and I have to design my day around making sure that this can happen. This has to become my number one priority in my business. Then at that point, you can actually make it happen.

Nathan, welcome to the podcast. Thank you for having me. Thank you so much for coming. This is going to be so much fun. I'm excited. So I'd love to start off with your backstory. How did you come to care about making money? Yeah. Okay. So I grew up in a family where there wasn't a lot of money. My dad worked in a ministry and everyone, you know, supported by donations. And so...

I actually grew up in a house or like was born in a house up in the mountains outside of Boise. And, and, uh, you know, it was like a tiny house before tiny houses were cool. Um, now I have a tiny house in my office and it's much cooler than the one that I grew up in. But, um, yeah, so I watched like the struggle of money or the lack of money be like kind of a defining factor of childhood. You know, like there was always enough food, but you know, not much more than that. And so, um,

Growing up, I watched my parents fight about money. I watched the stress that that caused and then ultimately divorce. And somewhere along there, I realized like, oh, you can actually make money. I think it was probably, oh, maybe late high school, early college when I first started reading like Jason Freed and DHH from Basecamp. And Jason talked about how making money is a skill and you can get better at it over time. And that stood out to me.

Because the point that he was making is you wouldn't expect to sit down at the piano and be able to play like some amazing song without practice. And the same way you wouldn't expect or you shouldn't expect to be able to sit down and, you know, start a company and do fantastic. And so really it's the combination of not one skill but like a thousand little skills just in the same way that music is, right? You know, there's music theory and timing and everything else. And business is, you know, confidence and sales and marketing and pricing and, you know, all the audience building.

And so when I understood that, that making money was a skill that you could get better at with practice, then I was like, okay, I'm going to be, you know, like someone else could be the child prodigy in music. Like that is what I'm going to be as good as I can at making money. So even hearing you say that, that making money is a skill, I noticed myself having a bit of a moment of surprise. I'm like, oh yeah, I guess it is. Because I guess...

It's obvious that playing the piano is a skill, but it's not that, it's weirdly not that obvious that making money is a skill. Well, I think you can't see it, right? I can't sit down. I'm like, Oli, let me just watch you make money.

You know, and it's very indirect. I can watch you play the piano and I could watch you, you know, do scales or build up, you know, these individual things and put it together into a song and all of that. But the skills of making money are a little bit more abstract. And we tend to assign them to things like, oh, she's good at sales because she has that natural charisma, right? Or, you know, he's just gifted with being a good copywriter, right?

But these are all skills that are learned. And sometimes people are better at them than others, right? If you grew up in a family that music was all around you, then you might take more naturally or you might have more of a natural ability towards some of those things in the same way that someone might have more of a natural ability towards sales or marketing or some of these things. But all of them have to be learned. Think about the first time you tried to sell something on the internet, right? Yeah.

How do you do that? When I tried to do it, I'm like, ClickBank, eJunkie, how do you even get money from a person to me? And now there's a lot more tools for it and it's easier, but it's still something that you have to learn. Creating a landing page for the first time, that is a skill. If you look at the first landing pages that a lot of content creators make, they're terrible because they don't understand that the headline should capture attention.

But once you know that, you never unlearn it. And so now, years later, if you've been doing this, you're like, I don't know, I made a landing page in a half hour. And of course it captured attention. Of course it checked all these boxes in the same way that using music as the analogy, right? Your timing is good because you have learned that. And so I think that's the thing that we miss. And it's hard as a beginner where you're like,

It just, it feels so unknown and there's so many skills and then someone who's been doing it a long time just sits down and it seems so natural because they have rehearsed for, in many cases, a decade or several decades. Yeah, that's such a good point. I think, so I made my first landing page when I was like 13 years old advertising my web design services. We'll put it up on screen if we can find, if I can find that screenshot because I still have it. It's just so funny. Yeah.

It was like, you know, want a website for your business or your life? Call this number. And I put my home number on it. It was like, they made up some names like UIA Web Solutions, like some shitty agency. But then sort of 15 years later, when we're whipping up landing pages for our products that are doing sort of millions in revenue, and the team is just like looking at me and being like, whoa, how did you just do that? And I'm like, oh, I mean, it's just like, you know, whether it's Webflow or WordPress or Kajal, it's all the same kind of stuff. You just put it together. It's just like, oh, you know, this is obviously the headline and

There's this whole thing that goes into it, but seeing it as a skill is something I've not really considered. Yeah, and it's really the combination of a lot of different skills. If you learn web design, at some point in there you probably learned about user experience and did some user research, and you understand the flow of eye tracking and eye movement over a page. It tends to go in a Z format where people, at least in English-speaking countries,

uh countries tend to read left to right and then they'll angle down and so if you want a call to action you're going to typically put it like if i want you to to do something that's going to be in the lower right and you know that at one point that was something that i learned and

That was probably 15 years ago. And now it's just very intuitive. And so when I come across a page and someone's like, oh, this isn't converting well, it's like, okay, well, let's flip the left and right columns. Let's change this headline. There's so many design things as well. Design is one of these skills that...

I feel very like blessed to have learned early on because it just applies to everything. And someone's like, oh, this page isn't converting. I'm like, well, yeah, it's because everything has the same visual weight, right? Let's make your headline a little bit bigger. That sub headline, let's make it a bit smaller. You know, you don't have to use black text for everything, right? Let's go to like a 70, 80% gray, you know, and you just add this level of quality and polish to it that becomes very natural when you do it.

And it spreads out through everything. And I see that so often with content creators where they put out this amazing content, especially written content, right? They say words matter. Words are the most important thing. And they are. But how you package them changes how they're perceived. And that's what's going to drive if someone actually really engages with it. So the number of e-books that I come across where the content is so good and

And the actual packaging and design of it is so bad. And I'm like, you're missing out on probably half of your audience because they're just like, oh, you know, the packaging isn't very good. And yes, I am judging a book by its cover or whatever else. And I'm moving on because if you didn't put that level of care into one aspect of it, the content's probably not that great either. And so in my team, we still use your authority ebook that you made like 10 years ago as like

This is what a PDF should look like. Because we often package up things as worksheets and workbooks and stuff for YouTuber Academy and things. I'm just sending them authority.pdf to be like, yeah, this is a good PDF. Don't just make it a simple Microsoft Apple page and print. That was actually... Apple used to have a product around making e-books specifically. And...

I'm trying to remember what it was because that wasn't done in Pages or something else. It was done in this other product that they've since discontinued because it was like for the whole iBook format and all of that. And I found that that was the best design tool that wasn't like Adobe InDesign or something, you know, like a full thing. But that's funny that you keep doing that. This is good. Okay, so just sticking on this idea of making money is a skill, just for one moment. A lot of people...

So it sounds like the way that we're talking about it right now, it's almost a given that we're talking about having your own business and learning all the skills to making money within your own business, which I think is also a niche way of thinking about making money because for like 99.99% of the population, making money is the thing that's tied to your job. I wonder, what are your thoughts on having a job versus having a business? And I guess in your early days, what took you down in that having a business route rather than the getting a job route?

Well, so if you think about the ability to increase your earnings in a job, you're fairly limited, right? The default is you're going to get some cost of living increase, right? Three to 5% a year, maybe. Now it won't outpace inflation, but, you know, or you're going to have to jump roles and level up, right? And we've seen a lot of people, and I had that in my own career where the first job that I had was making 60,000 a year.

as a designer, the first professional job. I worked at Wendy's doing food service, you know, did plenty of web design and all that as well. But in any job, for the most part, your earnings are going to be very closely tied to your time. And you can't really separate those. And so I wanted to get to the point not where I was making 50,000, 100,000, 200,000 a year, I want to get to the point where I was making millions a year. And there just aren't that many jobs where you're at that level.

There actually are, but not in the same, not in the worlds that I grew up in. Yeah. Right. I didn't grow up in the worlds of private equity and, you know, I dropped out of school. Like I didn't finish high school, dropped out of college. And, and so it wasn't like, oh, you know, let's go to Stanford and do private equity or, or, you know, some finance thing or anything like that. And so I was looking for ways that I could earn, you know, far more. And so, yeah,

I think that's where I've taken it on the earning side. Inputs and outputs can be completely disconnected when it comes to it. So why not just think, you know what, I've got a 60K job as a designer. I'm living in Boise, Idaho, which is fairly low cost of living is my understanding. It used to be. I can live a chill life. I go to work, do my 9-to-5, come home, I chill like crazy.

Why not be content with that lot in life? I mean, that's a good question. I think I've always been a creator. Like I've always made things. And so, yeah, I'm constantly learning and constantly making. And like, I think I just get really, really bored. And I actually, I spent two and a half years working as a software designer at this startup. And I had done freelance web design for a couple of years. And then in 2000,

the beginning of 2009. So at least in the U S the economy was down like crazy and all of my clients like stopped hiring except for this one company. And they, you know, they were like, Hey, we have even more work actually do you want to just come on full time? And so I joined them and we're there for two and a half years. And during that time I watched them raise a ton of venture capital. Uh, I think I was employee 15 and maybe peaked at 70 or 80 employees. And then they did a few rounds of layoffs and you know, I eventually left. Um,

But that was something I remember going through that process and finding that I was losing a lot of the skills that I valued about myself. Right. You,

I think it's really interesting if you were to write down, like, what do you value about yourself? And there's probably some things, you know, uh, like how you are as a friend and other things that are like really good. But then there's others that are, that you value about yourself that are, um, maybe a little more dangerous, uh, in the sense that they're, they're tied to things that you control us. So one thing that I value, uh,

about myself and really valued a lot then is how productive I was, how fast I was. When I worked food service at Wendy's, it was all about speed, right? How can you maintain this bar of quality and go very, very fast? Because when we work the drive-thru, there's this big timer over the window. And it's basically the amount of time from when a car starts their order to when they're driving away with their food, right? And we're trying to go, we want under 60 seconds. Okay.

And so we would like call up at the stores and be like, okay, for the lunch rush, you know, we're going to get 58 seconds. What are you going to get? Okay, we're going to get, I don't know, 57. You know, you're like trying to compete with them. It's just a friendly thing. But we got very, very fast and efficient. And when I did web design, when I went from working per hour to working per project, then I realized that for the first time, the speed and efficiency benefits me.

When you work at Wendy's, it's like, wow, you're so fast. Let's have a raise from $6 an hour to $6.50 an hour. You're like, I think I worked really hard and that's not benefiting me. And hourly work, maybe as a web designer, it's $50 an hour or something. But when I went to, oh, let me charge $2,000 for a project, then I was like, wait, the faster I am at this, my hourly rate increases substantially. And so then I was like, how do I template things? How do I stay super focused in all of this?

And then when I went and joined this company, I realized that I was losing those skills because no one else in that environment cared that much about working quickly. Especially as the company started to struggle, you know, there was that first round of layoffs. People would spend time like standing around the pool table complaining about how they didn't get paid enough. And I was like, none of us are even working right now, you know?

And so what I actually did is I realized that I, in my design coding abilities, I realized that I had lost the skill of speed. Right. And I didn't hone and refine it over the previous two years. And I, I had lost that. I would sit down to work on a side project at night and I realized like I wasn't very good at focus. I couldn't, you know, something that used to take me two hours to code out was now taking me three, four, five hours.

And so what I actually decided to do is I wanted to decide I was not going to lose that part of my identity. Yeah. Right. Like that would be a valuable skill. I'm like, no, I'm not losing that. And so I ended up switching, switching my desk from one that was like in the middle of a big room, like someone else had left. And so there was one way off in the corner and I got that. And I decided that I was going to be the best employee on that team.

And I was going to do it in three hours a day. And I was going to spend all the rest of my time learning to design and code iOS apps, other things. And so instead of moving at the slow pace of everyone else and just turning into someone that I didn't want to be,

I was like, okay, I still need this job. But I'm going to knock out all of my work, make sure I'm ahead of schedule and everything. And then I'm going to be in a place where you can't see my monitor. And I'm going to be studying how to build iOS apps. And I'm going to be coding on my own side projects.

And I rebuilt that speed and that ability to work quickly. And so then three to six months later when I left that company, I had a stable of iOS apps that were making money and I had new skills that I built up. But yeah, that's the thing of like, I'm never someone that's content to go at the same pace as everyone else. What do you think was it about you that sort of...

made you different from the other people on your team who were content to chill for eight hours a day and complain about how much they were being paid? I just love the juxtaposition between those two things. I'm like, it'd be one thing if we were the absolute best team, but we weren't. I've always wanted to get the most out of my time and move as quickly as possible. So I was homeschooled and I grew up with my parents really teaching me that I set the pace.

So I remember two different things. The first is I was probably 11 or 12 years old and we lived up in the mountains. And so I remember just the most beautiful snow coming down in the winter. And I loved sledding. And I'm just, I've got, you know, algebra that I'm supposed to work on. And I'm looking outside and like the snow looks so good and I just can't focus on it. And I think I complained to my mom about it. And she goes, you know,

You just have a set amount of work to get done. It doesn't have to take an hour or five hours or whatever. Like you don't have to sit here and do school till 3 p.m. You just need to be here and do school until it's done. And

Like that is the most focused 11 year old you've probably ever seen where I was like, okay, great. Let's get it all done. All of that, you know, my little brothers and I'm like, no, I don't have time for this. Like I gotta, I gotta get my school done so I can go sledding. And I think like an hour or two later I was out there sledding because I realized that like if you cut out all the complaining when you're setting math and all that, like it goes remarkably faster. So that was the first thing where realizing like, okay, uh,

it's not a fixed amount of time. And the second thing is growing up, I spent the most time with my two older siblings. And so because I like tagged along with them and their friends, all of our friends were older than me. And so that wasn't really a problem through like kind of junior high, high school ages. But really once I was just starting high school, they were all thinking about going off to college. And that's when I realized like, oh, this age gap is going to become very noticeable.

because I'm sure they're only two, three years older than me, but then like, I'm going to be finishing out high school and they're going to be going to be gone at college. And so I went back to my mom and I said, you know, is high school a fixed amount of work or a fixed amount of time? And so it's basically the same question that I asked her or that she had brought up about, you know, math homework on a snowy day, but applied to a bigger chunk of time. And I

She had homeschooled my older siblings who had already finished high school. And so she said, no, I have the exact curriculum that you're going to go through. You can graduate high school whenever you complete this curriculum. And so I remember thinking that we would do these drives from Boise to Seattle, which is about eight or nine hours, to go visit family every summer. And that was before iPads and all of that. And so I remember thinking, I'm really bored on this drive.

And I'm really bored when I do math. So why don't I just combine these two? And I would do like a month's worth of math lessons on a drive over to Seattle. And I had my older brother sitting next to me. And whenever I got stuck, he could help me. And we'd go through that. And so from when I was 13 to when I was 15, I finished all of the high school curriculum. And then I graduated just a little before turning 16. And then I was off going to college and all of that.

So really the idea of you set the pace. Derek Sivers talks about this in his book, Anything You Want, how he went through Berklee School of Music very, very quickly because of this one professor that was like, let me teach you a semester's worth of music theory in like two days. And Derek talks about how like the class goes at the pace of the slowest student. And sometimes that's you and sometimes that's someone else and it changes based on every topic. But like averages out, it's going to be quite slow.

And so I've just always been obsessed with this idea of you set the pace, right? Do you want this to take multiple years? Sometimes it should, and sometimes it's the best for you. Or do you want to get it done very quickly? And yeah, that's been probably a defining factor in my life. That's so good. I was just taking it. I feel like I had so many kind of brainwaves as you were saying that. I think this idea of fixed work versus fixed time is really important. Because if you're, for example, working at Wendy's,

That's fixed time. Like, you know, the work is always going to be there. It's not like if you work faster, you can then put your feet up, I suspect. But actually in most areas, if I think of every job that anyone that I know has, or if you're a student in school or university, it feels like fixed time, but it's actually fixed work. Like when I was working as a doctor, it was fixed time. I was there from eight till six.

But it was actually fixed work in that if I could see the patients quickly enough and to get everything done and get them seen, all of that stuff is done. Now I have some, I've got some spare time now. And where a lot of my friends in that context were using that spare time or just sort of going at a leisurely pace because they know they have to be there until 6 p.m. anyway, because why not? It's a bit more chill.

In their spare time, they were like scrolling TikTok or whatever the thing was. Whereas in my spare time, I had a side hustle. And so I was like, great, I've got an extra 20 minutes that I can like, you know, grind and

plan out a new YouTube video or something like that. Similarly, when I was at university, going through medical school, I was like, okay, I need to get this essay done as quickly as possible so that I can tinker away on the business I was building on the side, or I'm designing a landing page or making a site in WordPress and stuff like that. And it sounds like that was your approach when you had the day job as well. Like, let me get this shit done as quickly as possible so that I can then use the rest of the five hours in the day while I'm being paid to be here to actually learn and improve my own skills and build my own stuff on the side. Yeah.

Yeah. And I, I think that's so important, but most people don't have that side thing. And many of them are completely content with that. Right. Um, I have a brother who has a great career in finance, super happy with what he's doing and all that. And, and just has, you know, I'm over here like constantly starting all of these things and all of that. He doesn't care about that. I think we were both equally happy in life. Uh, and we just have very different, uh, different approaches. Um,

And, but it's just, it's core to who I am that I'm going to figure out, okay, what can I learn? What can I implement? And I always try to find the overlap, right? Like when the iPad came out in 2010 for the startup I was working for, you know, we were designing iOS apps. And so then instead of like doing the minimum to, okay, I designed the app at the time we were designing in Photoshop, that was enough, you know, I handed it off.

That was all that was expected of me. But then I was saying, hey, why don't I learn how to use Interface Builder and Xcode to be able to implement the UI? And let me take that further and learn how to program. So it wasn't like I was at my job then doing something 100% different on the side. I was saying, okay, how can I do what's expected of me but take it much further in a way that's going to benefit me long term? I learned programming skills there, right?

that were related to my job but not required that I went on to use for years. And I sold, you know, $50,000, $75,000 worth of iOS apps that I, you know, that were an amazing side hustle thanks to the skills that I took further. Yeah, I think that's a really good point, Aram. I think, like, if...

I'm always mindful when I do these episodes, speaking to other entrepreneurs and stuff, it can seem as if it's like, oh, starting a business is the only way to be happy. But it's really not. If someone listening to this or watching this is genuinely happy with their day job, fantastic. The goal is happiness, contentment, and meaning. The goal is not have a $100 million business. And if you get happiness, contentment, and meaning from the day job, which you really enjoy...

And then you go home and do stuff on the side and like have hobbies and have work life balance. And that is absolutely fantastic. That is what we're all trying to strive towards in some way or another. But equally, I speak to a lot of my, a lot of people I know who have the day job and they're not content. They're like, oh, I'm feeling my skills are being stifled. I'm feeling like I'm losing a bit of myself. I used to have all these interests when I was a kid and then they got squashed out of me by the education system, et cetera, et cetera. Yeah. I'm capable of more. Yeah. Yeah.

And those people feel like, if only I could have an extra 3K, 5K a month of passive income or something like that, oh my God, that would be so liberating. It would buy my freedom. Whereas there are some people on my team, as much as I encourage people to have side hustles, Alison, our head of customer success, is like, I don't want a side hustle. I just want to chill. I enjoy my job. I enjoy my team. I get home from work and then I hang out with my friends and I go see musicals in London. And I'm like, great. She's like one of the happiest people I know.

But I think it's that thing around like if you're complaining about your situation, then starting a business might actually be a reasonable option if you do feel like your job is not helping you reach your potential. When I think you brought up something of, you know, even the $1,000 to $3,000 a month from a side hustle, you're going to get two huge things from that. First, all of that money is on top of what you already made. And so you don't have the same level of expenses that that money has to pay. And so it's actually like substantially different.

you know, as far as the impact that it could make on your savings or your vacation budget or whatever it is that you value. And then the other thing is the skills that you learn. Like in most companies, if say you're at least 10 to 20 people in the company, and then it's especially true as you get into a 500 or a thousand person company or beyond, right? There's someone else who knows how to do

everything like tangential to your job. And so you're like, I do my thing and you know, in my, in my case, right? I do the design and Photoshop and I can hand it all off. There are talented people who will build a full app from that. And so you just don't have the same level of growth and development because you don't have to write. Your job is to do your thing in your lane. And the people who say like, no, I want to know more about everything that my work touches and become obsessed with how much can I learn? Right.

When you realize that your brain is not this, as new information comes in, something else has to go out. You're going to do the digital nomad thing. You're going to be like, okay, I have these two suitcases or something. And someone's going to be like, here's this. And you're like,

What am I going to get rid of, you know, to be able to make room for this new thing? That is not how your brain works. You're going to be able to continue to take on new information. So something that I'm learning how to be a pilot right now. And so I'm partway through flight lessons. And something that a friend pointed out is like, once you're a pilot, you're a pilot for life. Like your license is for life. Now you need to like stay current and all of those things and do flight reviews. Right.

But I think of it the same way with any of these skills. Like once you're a designer, you're a designer for life. Once you know, like the principles of great video and production and all that, like you have that for life. And so I'm 33 and I'm thinking about like, okay, what are these new skills that I have forever? And so when someone presents me with the opportunity to learn a new skill, then I'm like, Oh, thank you. Like, like this is amazing. What a gift because I'm going to have that hopefully for the next 60 years. And, uh,

Yeah, I think it's just a different mindset than a lot of people have where you're just like trying to fill the time or finish the day. Man, that's so good. Today's episode is very kindly brought to you by Huel. Now, I've personally been using Huel regularly since 2017 when I discovered it in my fifth year of medical school. And if you've not heard of Huel, they're a business that creates convenient, affordable meals in a variety of different forms, but all of them are nutritionally complete.

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taking an opportunity would have allowed me to build new skills. So for example, one thing that we've been toying with the idea for a while, and maybe we'll talk about this when we talk about billion dollar creators, is can we build our own productivity app? We've got enormous distribution. Even if we have feature parity with an existing productivity app, we can make our own to-do list and drive tons of traffic to it, and it would be great and stuff. Then I'm thinking, oh, but that would require...

That would either require me to hire a CTO or to try and learn the skills to become a CTO and figure out how to hire developers or figure out how to work with an agency and then our costs go up, etc. And I know I would learn a lot in that process of trying to build a consumer productivity app. And I know it would be pretty hard. But there seems to be in my mind this trade-off of like, oh,

it's too much effort. Like it's, it would teach me a lot of new things, but it just feels kind of hard. Like, does that vibe at all? Yeah. Well, I think it's,

The way that I think about setting goals is around what am I going to learn from this goal? Right. So we have a goal at ConvertKit growing to a hundred million a year in revenue. Yeah. We sit at 40 million a year right now. And so, you know, in my head, there's like the little, I don't, do they do this in the UK? Like fundraising things, they'll have like a thermometer that they like color it, you know? So I'm like, okay, we're 40% to, to goal. And yeah,

I don't set the goal because I'm going to hit self-actualization when revenue tips over that additional digit. What I think of is, what are the skills that I have to learn to build something to that level? And so we talk about how one of the best paths for you to build a business worth $100 million or more is a consumer productivity app.

And we could set that out and that's fantastic. But if we break down and go, okay, that's the goal. Who do you have to become in order to achieve that goal? What skills do you have to learn? And if we write those out and it's things that you talked about, right? You have to get very good at understanding user behavior, how to work with developers, how to hire, how to scale a team, like all of these other things. And so you list out all those skills and if you're like, yeah, no, no,

Those skills aren't interesting to me. That person, right? If we look at future Ali who has to have those skills and be in that, if that life doesn't sound interesting to you, then great. Move on to a different goal. I think too often we either set a goal without realizing what's going to be required to achieve it, who we have to become to achieve it.

Or we go the other way and say, oh, this is what I'm trying to do. I want to get better at this one skill without a goal in mind. And so I think the overlap of those two things, clearly understanding what's the goal and why, and then who do I have to become to achieve it, is what results in something that you're really, really proud of and willing to work on for long enough. Because if you're like, hey, I have this idea for an app. I'm going to throw it together. It should be live in three months, and it should have

100,000 users by the end of the year and, you know, like all of this stuff. Guess what? It's going to not work out that way. Like it's going to be

10 times harder than you thought, take 10 times longer. And if you're just looking for the neat way to use your audience for distribution, then you're going to give up when it gets hard. But if you're like, oh no, this is the goal, this is the mission, and I'm very clear on who I have to become in order to achieve that, then you'll stick with it when things get really hard. There's a journaling prompt I've started thinking about recently, which is, because you know people say that

One way to figure out what you want is ask yourself, what would you do if you knew you couldn't fail? And I made a list of that and Productivity App was on the list. But then I asked myself, what would I do even if I knew that I would fail? And Productivity App was not on that list. But there were a couple of other things of like, even if I knew that this would fail, I would still like to do the thing. I love the idea of building a sort of

hour one to two hour long one man stage show which is like a combination of like life advice meets magic because i'm into magic and like hypnosis yeah that kind of stuff that would be cool and it will learn a lot even if it fails right you'd be very proud of that yeah end product even if a failure is like like 100 people came to watch it exactly yeah and like writing a book it's like i even if not many people buy the book as long as i've written a book i'm proud of i'll be i'll be happy with that whereas for the productivity app

I'm kind of like, I wouldn't do this unless I knew it was going to be successful. And if I knew it wasn't going to be successful, it doesn't seem fun anymore. Yeah. And so in that case, one, I love that clarity because it points to what you're going to take away. Right. Most people are saying this is worth doing if I achieve the goal or if I achieve 80% of the goal. Yeah.

And what you're saying is this is worth doing even if I achieve 0% of the goal and I actually like the true goal is the experience and what I learned. And I think that's how you can find what's most aligned to what you do. The one thing I would say is often people don't know. I mean, it's corny, right? But you don't know what you don't know. And so like for me in building the company,

I've spent a lot of time getting good at design and code and marketing and all of that. And I'm trying to get good at building teams and setting goals that keep people aligned. And right. It's an entirely different skill to run a company at, you know, a hundred people and, um, you know, whatever, 50, a hundred million revenue and beyond from there, uh, then it is, you know, for me to be selling eBooks like I was before. And so, um,

The shift that has been most helpful for me is to fall in love with the process of building and scaling a company rather than to fall in love with the theoretical destination and whatever that might buy me. And so then when I'm going through something that's really, really hard, then I'm like, oh, no, the growth from this transition is what I signed up for and what I said that I want. And so this is the thing that will make the difference. And then the last thing that keeps me

from getting too discouraged in that is I like to write out my problems that I've encountered and so just sort of have a timeline of them. And then to look and say, how would like current me deal with my past problems? Right. So for example, the early stages of COVID right in March, 2020,

You have no idea what's going on. Teams are worried. We were already a remote team. And so we didn't have that like shut down the office dynamic. But we had both a crazy amount of growth from people being like, I guess I'll start an online business. And also a huge amount of cancellations from people saying like, well, no one's traveling. So let me shut down my travel blog. So I'm not paying for all of this. This was a very, very hectic time. And it was really stressful. But now that I've been through that and I feel like I'm three years more developed as a leader, I'm like, okay, I think I can manage that just fine.

Right. And there's plenty of other things that I remember being very, very stressed out about. And now I'm like, oh, that like, that's almost cute how simple of a problem that was. And so that helps me stay grounded when I'm thinking about the things that I'm encountering right now that are so, so stressful. And I'm like, in two years from now, how am I going to look back on this problem? And my goal is that I look back on it and say like, yeah, for, for past me, that was a very challenging problem. But currently it would be like, okay, that makes sense. We're on to like,

bigger harder problems that we can handle with the same level of stress and so i love using that growth that's one one of the things in journaling is just like what are the hardest problems and so you'd be like march 2020 you know how to lead the team and navigate through coven right um june 2020 it would be like all of the um social justice protests and um black lives matter and what to do through that right and you kind of just level up all these things that

that you navigate even a simple right if you have the you build that that consumer productivity app okay what happens when it gets pulled from the app store for the first time because of some random thing right you know I've been now had that happen on four different apps at different times right and so you're like oh this is how you do it this is you know how you navigate it and so but in the moment that would be the most stressful thing that you've probably ever dealt with

And so I love looking at that growth and seeing the past progress in the same way that you're going to the gym and you're like, okay, you know, I was doing this, I don't know, deadlift or something. And this was insurmountable. And now like, that's what you do for a warmup set. Yeah. So you're, you're in the day job, you're making your 60 K, you're completing the work in record time. And alongside you're learning how to build iOS apps. What happens next in the journey?

Yeah, I, the first iOS app that I built to sell was, I called it One Voice. And my sister-in-law was working with kids with special needs, like who had nonverbal autism. And so she

They could think through everything they wanted to say, but really struggled to verbalize it. And so there's these devices that were like ruggedized touchscreen PCs that had terrible battery life and cost an absurd amount of money and all of that. But they would use an app on it that had synthesized speech. So they'd select tiles and then it would build a sentence and then it would speak for you.

Um, and so she was doing that. And when the iPad had come out, um, Hannah, my sister-in-law was like, this should just be an iPad app. Like, but it's such a niche, uh, product and the money is all made in insurance paying for it. And so like these were priced at $7,000 because that was exactly what Medicaid in the United States would reimburse for it. You know, and you're like, all right, I understand how this works. Um,

And so I ended up making this iPad app that was the same thing, right? And so you bought an iPad for whatever, $700 or $800 and you bought the app and it naturally had fantastic battery life and barely weighed anything and all that just because it was on better hardware. And so I ended up building that app and selling a lot of copies of it. And then I want to say the app probably made $40,000 or $50,000 over...

maybe three years. And that drove a lot of my side hustle. And you built that while you were still working at the day job? Sick, that's cool. The job paid for me to go to a developer camp that was at the PayPal offices in San Jose. And they did a hackathon. And so it was like, oh, you join a team and people had their different ideas and you join a team, code with them the whole weekend and meet people and learn a bunch of stuff.

And none of the ideas seemed that interesting. And I was there with a developer friend from work. And so I was like, does anything sound interesting to you to join? He was like, no, not really. And so then I was like, well, I have this idea for an app. Let's design, build it, and code away on it. And so that weekend, he helped me with the initial version, and I learned a lot. And then maybe the next few months,

you know, I'd build more. It actually was the way that I learned to code. I always like to make something specific. Like I'll do the, you know, 100 level, like let me just learn the basics. And then I'll get to the point where I have something specific that I want to make.

And I code in every direction until I get totally stuck. And then I would go to a friend. There's a few developer coworkers. And I would go over to their house on a Saturday morning and be like, okay, I'm now stuck in these three categories. And they'd be like, oh, okay, here's why. I'm trying to do something and they're like,

do you know about different types of numbers? I'm like, what? Okay. We've got floats and integers and you know, like there's like computer science one-on-one. Um, but it was fun to get, have someone help me get unstuck. And then I'd be off like coding more and Googling and stack overflow and everything else. And, um,

But yeah, I built that app. I built one that I called Commit, which was a habit tracking app. So like along the like don't break the chain idea. That ended up being really impactful. I built a flashcards app that did delayed repetition. And those are the three that like I actually sold and got traction with. To the point where when I quit my job,

to do freelance iOS design, I was making about $3,000 a month on the App Store from those three apps. Wow. How did it feel at the time to be just getting $3,000 a month from making money while you sleep, basically? Yeah, it's absolutely fantastic. And because it was integrated, right? Yeah.

The apps that I built helped me get more, like demonstrate expertise, which helped me get more clients, which helped me, you know, both pay for all my living expenses and learn new things that went into the apps that I built. And so it was this like, you know, virtuous cycle very early on where I was like, oh, this is all directly related. And I was just,

doing what I wanted. And that was also the first time that I was able to travel and not be tied to an office job. So that was a really good time. Nice. When was this? 2011. 2011. Okay, cool. Yeah, 2011 to 2012. Nice. Okay, so you've got the day job, you're learning skills on the side, building these iOS apps as a side hustle. You then quit the day job and you become a freelance iOS designer. Yeah.

What happened next? When did the e-book start to enter the frame? Yeah, so around the time I'd come across a guy named Chris Guillebeau from reading, I think he'd written a guest post on Tim Ferriss' blog. And it's one of those things, I feel like this doesn't quite happen as much anymore. Maybe it still does.

Where you come across someone's work and then you just like fall off. Yeah, you just, just everything. And this was me with your podcast and blog about like five years ago. I love it. Yeah. Where you just uncover everything. And so I, I started following everything Chris did and he had this, oh, I remember this

Like I read everything and it was like, Oh, he has a book coming out. Oh, he has a book tour that he's doing for this book. This is the book was called the art of nonconformity. And then I was like, wait, he has a book tour where he's going to be in Boise on Tuesday. And so then I went to the, the event and met him. And, um, but he talked a lot about building audience and self-publishing. Uh, he had two eBooks that I really liked that were for free. Um, and,

The first one was called a brief guide to world domination. Chris was always so good with naming things. You know, I just love the juxtaposition. It's sort of like Mark Manson's right. The subtle art of not giving a fuck, you know, you're like, Ooh, these don't, uh, the juxtaposition within that title works really well. And so Chris back in 2011 or something is doing a brief guide to world domination. Um,

And that was really fascinating. And then he did another one called 279 Days to Overnight Success that was about his blogging journey. And basically him going from starting his audience to earning a full-time living, which he defined as $60,000 a year. I think in the e-book, by the time he publishes it, he's gotten to like $65,000 a year.

And he put them into like these beautifully designed PDFs and distributed them. So a lot of what you're seeing, you know, in authority and all of that is inspired by things I learned from Chris and watched him model. And so he was following the self-publishing path, build an audience, self-publish an ebook. And so then I thought, okay, maybe I could do that. But I didn't think I could sell books on that level. And so I thought, what I actually want is more design clients.

And so I'm going to write a book and self publish it on designing iOS apps. Um, and then the goal, well, I had two goals from it. Uh, first get a whole steady string of clients, right? You want to hire the guy who wrote the book on, on design. Um, and then also if I can make $10,000 in revenue over like the lifetime of the book, that would be a success. I didn't want to do like the true or the full, like, Oh, this, um,

This book is just a business card. It doesn't have to make any money. Like I think that's a cop out, right? You should try, if you put time into making something, you should try to distribute it to as many people as possible and make some real money with it. So I ended up like building a landing page, writing tutorials, driving traffic from the tutorials to say like, Hey, I'm writing this book. Sign up to get the wait list. Built that email list on MailChimp. On launch day, I had 798 people on the wait list.

And I ended up selling $12,000 worth of the book in the first day. Wow. And so I got hooked on a couple things. One, I realized like, forget freelance design work. Like the goal was to get clients. I never took on another design client after that. Right. I just, I was all in on self-publishing. And then the second thing was,

is I became obsessed with the world of self-publishing. And like, okay, what can I do with this? And what can I do with marketing? And I was okay at marketing. I knew how to make a landing page. I knew how to do some of these things. But then I was like, what can I do? And really it was email marketing. I thought at the time that...

Instagram and Twitter and these other platforms, Facebook, would be driving most of the traffic, most of the conversions. But it was email that drove all of that. And actually in Boise, where I live, there's like this OG internet marketer crew that's there because ClickBank and Bodybuilding.com and a bunch of these companies were all founded in Boise. And so you get these people who have been around for a long time. I was talking to one friend, Ron Sperling,

about this. And I was like, email is selling more copies than every other channel combined. And he just looks at me and he's like, yeah, we've known that since 2003. Like, what do you want, a gold star? I'm discovering this thing that is blowing my mind. And he's just like, everybody knows that. I didn't. And so that dove into my love for self-publishing and marketing, and particularly email marketing.

And then actually the day after that, I had been using my habits app commit that I'd made to write a thousand words a day. And so it popped up and said like, are you going to write a thousand words today? And I was like, no, I finished the book. I published it. And I was like, but it had like 84 days in a row of a streak. Okay, I'll write a blog post about how the launch went. So I wrote that up, published it. That drove some more sales, got people paying attention from like, oh, you know, some random designer can make money selling a ebook. Maybe I could too.

And then the next day, the app did what it does and it popped up again and said, are you going to write a thousand words today? And I was like, well, I wrote the book. I wrote all the launch emails. I wrote a blog post summarizing how the launch went. Like what else would I write? And then I thought like, I mean, I know web design and specifically web software design really well. Cause that's what I did for years. It's like, okay, let me write a book about that. Let me follow a similar habit or similar pattern and,

And so then I wrote a book called Designing Web Applications. It didn't take that long to write because I wrote 1,000 words a day. And so 90 days later, I published it. The email list was up to a couple thousand people at that point. I ended up doing $26,000 in sales of that book in the first day. $50,000 in the first month. Something that I just realized, someone asked me this years ago and I didn't have an answer for it. But I just made a little connection of why I targeted one day sales.

Because it's like, okay, why does the first day of sales matter? Especially because I have this big spike. Because I would offer a 20% off discount if you bought the first day and then that would go away. And then there'd be sales tapering off. Chris Guillebeau, in one of his articles, talked about how he hit $100,000 in sales in a single day from a course launch. And I think that always stuck with me, of the one day thing. And I like...

designed my launches around a single day number, even though I think that probably the optimal launch would be over the course of a week, you know, or, but it's interesting. These little like examples that stick with you. Yeah. So I, yeah, always optimized for, for a single day number. But the point is that I got on this path of writing and launching eBooks and just felt like I had discovered something absolutely incredible.

A couple of questions on this. So I remember now one of the early blog posts I came across that you wrote, well, it wasn't early for you, it was early for me discovering your stuff, was when you'd written for like an absurd number of days in a row. Can you remember how many that was? The chain got up to 600 days in a row. You wrote a thousand words a day for 600 days in a row? Yeah. What the fuck? Well, first a thousand words is not that much. Yeah, it's not that much, but it feels like...

Feels like a lot. I mean, it comes out, it was like on one hand, so a thousand words a day is probably two and a half pages. Right. And I remember Tim Ferriss talking about this. Chris Gillibow talked about it. The way Chris Gillibow phrased it, he had this, like, it's really easy to, what did he say? It's really easy to write a book every year, write 50 blog posts and another 50 guest posts.

what else? Like a couple of long form writing projects, maybe some magazine articles. He's like, just lists out all the stuff. He's like, it's really easy to do that in a single year. And I was like, what? It takes years to write a book. It takes years to do all of this. And he's like, if you just write a thousand words a day.

And we talk about like habits compounding over time and, you know, these small things adding up. But 600,000 words is an insane amount of content. That's absolutely insane. And I mean, that one habit built my entire career, right? Because that's a whole lot of email newsletters. It turned into three self-published books because later I wrote Authority.

Actually, I had this time period from September 2012, I published the app design handbook. December 2012, I published designing web applications. And then April 2013. So in this seven-month period, I published Authority. And so I wrote three books in that period of time because I was just churning out content. Grew the email list. That one habit just was absolutely insane for me.

This episode is sponsored by Kajabi, and they've actually got something really valuable for all of our deep dive listeners. Now, if you haven't heard of Kajabi, it's basically a platform that helps creators diversify their revenue with courses and membership sites and communities and podcasts and coaching tools. So it's one of the best places for creators and entrepreneurs to build a sustainable business. We started using Kajabi earlier this year, and as soon as we started using it, we were like, oh my God, why haven't we been using this product for the last three years? It's got everything you'd possibly need for running an online course or hosting an online community or building an online coaching business.

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Now, back in May 2023, I did a keynote at a Kajabi in real life, Kajabi Heroes event in Austin, Texas. And in that keynote, I talked about the exact steps that I use to grow my business from zero to over two and a half million dollars per year from course revenue alone. Now, people paid for the pretty expensive tickets to watch this keynote at the Kajabi Hero live event. But as an exclusive deal for deep dive listeners, Kajabi have very kindly offered to provide the recording of that keynote completely for free to anyone who listens to this podcast.

So if you're interested in getting completely free access to that keynote, just head over to kajabi.com forward slash Ali. That's kajabi.com forward slash A-L-I. And that'll be linked in the show notes and the video description as well. You just enter your email address and then you will get the recording of that keynote completely for free, whether or not you ever become a Kajabi customer. So thank you so much to Kajabi for sponsoring this episode. What did it look like? Like, practically speaking... Okay, so...

I'll give you some context. Our mutual friend, Sean McCabe, had a course somewhere about writing in Ulysses, the writing app. And I watched that course many years ago and I was like, I want to write a thousand words a day. This was when I discovered your stuff. I did it for like three days and then I dropped off. And like two months ago, I rediscovered Ulysses on my iPad and I set the target. Like I put all of the folders into one folder so I could track that folder and I set a target of a thousand words a day.

And when I do write and I'm typing away, I find myself effortlessly hitting a thousand because it's actually not that many words. And when I write my newsletter, I'm like, oh shit, this was 2000 words. Better cut some of it down. And I'm curious, what did...

for you, what did this process of a thousand words a day look like? What, what app were you using? Where were you writing? How did you figure out what you were going to write about? Like where did the inspiration each day come from? How did that work? Well, it was weirdly like the requirement was that it had the app I wrote and had to have really good word tracking because that was the word count. Um, and so I used Scrivener because that was the app at the time that was the best at having like individual, uh,

pages almost, but then would be summarized. Well, um, it could be compiled total. And so Scrivener let you set a goal like, Hey, I want this book to be 35,000 words. And it would tell you both your daily progress and your total progress against that across all of the like pages down, down the side. So you could organize it and categorize the whole thing. Um, so I wrote in Scrivener, uh, would, if I, when I was writing a book, I would write an outline for it.

And then I would take that outline and make folders and empty pages for each title within it. And I would...

put an asterisk at the beginning of the title if I hadn't written anything meaningful for it. So I would kind of just skip around and be like, oh, click on this. I don't have anything to say about that today. Click on this. Oh, here's a few notes that I would add to it. And like, oh, there was that article. So I'm just kind of compiling things. And then I'd find one and I was like, oh, I have something to say on this. And I would click in and write a whole bunch as much as I could on that one topic and then keep going from there. And so that

It was kind of sporadic in that sense. Yeah. But, you know, it eventually built out a full book. And then I have another section for my marketing copy, right? Like another folder at the very end. Because I knew I had to write launch emails and landing pages and all that. And like, that absolutely counts. It's always my thousand words for the day. Everything counts. And there'd even be some days, like, I don't like editing. And so I would count. I was like, okay, this is an editing thing.

hour. And that to me was equivalent to a thousand words, you know? So I'm like, I'm going to force myself to edit and chop down and all of that. And I'm going to get credit for my day's worth of writing. Um, the other thing that I would do is try to make it easy just in Apple notes to like throw out ideas of like, Oh yeah, okay. This is what I should write about later. Um, and it's a classic writing, uh, technique, um,

But to end... Oh, who talked about this? Someone famous. End in the middle of the sentence. It was someone famous. Yeah. I've cited them in my book, but I can't remember who it was. Yeah. Was it like Hemingway or something? Probably. Yeah, something like that. Yeah. Twain, Hemingway, or Einstein, or Lincoln, or whoever it was. No, I'm just kidding. Gandhi. And so I would just do all of those classic things. And usually when I would sit down and have nothing to write about, like if you just force yourself to write for like...

And you get through that first 10 minutes, then it's totally fine. The other one is Seth Godin has a quote where basically about writing, you should write like you talk because no one, you know, you don't have talkers block, right? But you know, if you're just trying to talk to yourself and so using now transcription stuff is really good. And so like just talk on the topic. I'll do that when I'm in the car, I'll just start a voice memo and then be like, okay,

what do I have to say about audience building? You know, like whatever the topic is. And then I'm like, okay, and then what about this? And here's a story. And it's all like nonsense. But then you transcribe it and you go through and you're like, okay, that's a whole thing to write on. So it's this. And then that, you know, you rewrite it and you get the stories and the structure and all of that. But it's pretty straightforward. You just have to force yourself to do it. But the habit compounds in a ridiculous way. This is good shit. I'm feeling so inspired right now.

I feel like if I actually sat down and wrote a thousand words per day, that would be the single thing that would drive me most towards literally every single goal that I'm working on. Right. And even goals that I don't even know I have right now. Because they're all around sharing my thoughts, content creation, writing, making videos. Well, and getting clear on all of these...

All of these ideas write something we talked about these flagship essays that I like to work on. I have three, um, ladders of wealth creation, billion dollar creator, and then the creator flywheels. These are all on things that I generally know to be true or like, I'm like, yeah, this is how wealth is built, but I can't quite explain it. And so through writing, I get obsessive about how do you explain this? Why, why does this work in a certain way? You know,

And then it turns into this thing to get to where I understand the concepts well enough that I can truly teach it. And that's what I love with writing is finding all the things that you intuitively know to be true or observe in the world. And then someone's like, okay, why is that? And you're like, it just is, you know? And that really takes you into like writing forces you to unpack that. And then one of my mantras in life is teach everything you know.

Because that turns into, or we have this idea that only experts can teach. And the main principle behind my book, Authority, is that we don't, people don't teach because they're experts. We perceive them as experts because they teach, right? It's chicken and egg and we have it backwards. And so in that, if you step into a world where you're like, okay, I'm just going to teach what I learned today, then you build the habit and you write it down and someone's like, okay, I'm, you know,

following this web designer who is brand new but they're on a journey to get a job at you know web design agency and they're just every day they're sharing and teaching what they learned and they're doing it from a beginner's mindset and i think you learn way more from that person if you're following like two steps behind them then following the super advanced expert who forgot how like who cannot relate in any way to the problems that an absolute beginner is facing

I thought about that when learning to code in Ruby, which is what ConvertKit is written in. I really struggled to install Ruby, but all the tutorials were like, why would you, you know, they all assumed that that was done, right? And then I came across someone who was a beginner who had said like, okay, I just got this done.

Here are all the roadblocks I thought, not like the ideal path, but this is what I actually ran into and how I solved it. And I was learning from someone who was like two steps ahead of me and they actually gave me the answers and I followed them, their content for a long time. So anyway, writing, teaching, it all comes back to that. It's all the same stuff. Yeah. Teach everything you know.

The book Show Your Work by Austin Kleon was a big, that was the thing that made me start my first blog in like 2016. Yeah. Because I'd been toying with the idea of like, I really want to have a personal blog. But I was like, blocked by like, oh, I don't know anything. Why would anyone follow me, et cetera, et cetera. Show Your Work was just like, share what you're working on. Yeah. And at the time I'd, you know, I'd been four years into building this medical school admissions company and website design. And I was like, I mean, I have learned some stuff along the way about like,

how i started the business and all this stuff i was like great i'm gonna do blog posts about that and that was the precursor to the youtube channel that happened a year later so i'm all about teach everything you know i love it um yeah my i used to have three mantras on my wall and by the way i love looking at your books because you have show your work uh in the austin cleon section of your bookshelf um but i i had these three posters on my wall in like my first real home office uh

And there were the three mantras of create every day, teach everything you know, and work in public. And that was like my equivalent of show your work. And then the posters, I should bring them back. It's been years since I've done it. But up in the, like kind of small up in the corner, they say the secret to growing your audience is to, and then the big thing is work in public, create every day, teach everything you know. What do you mean by work in public?

Well, it's the same idea of showing your work, right? Like what is the thing that you learned today that you could share with other people? Or so many people say like, okay, I, well, I created my, I wrote my ebook, right? I published and launched it. And someone's like, oh, sweet. I bought the ebook from you. I bought, I'm learning app design from you. All of that. That's super useful.

But most people don't take the next step and write the blog post about like, here's how I did the launch. Here's how much money it made and everything else, which is actually like the least difficult part. You know, everything else doing the thing was way harder than explaining how you did the thing and how it went. And so working in public in that case was probably the blog post I published the day after I wrote the app design handbook that said like, okay, it made, you know, 12 grand. Here's the launch sequence. Here's what drove sales.

There was some overlap, right? Some people who were designers wanting to learn for the app, or some people who wanted to learn app design were the same people who wanted to read about how the launch went. There was definitely overlap. Not 100% overlap, but there was some.

But then it brought in other people who wanted to learn about self-publishing who were like, oh, this is possible. Oh, and then I know someone who wants app design, right? And so it was marketing in a sense, even though it wasn't like architected from the beginning to be great marketing. But I think that process all the way along of teach everything you know, work in public, those are the things that make a big difference. When I started ConvertKit,

I've really embodied that work in public idea when I said, hey, I'm going to build a software company. I'm going to do it only with $5,000 of my money. It's going to be funded by customers. And my goal is to get to $5,000 a month in recurring revenue within six months. And I called that the web app challenge. And I blogged every week about here's how I chose a name. Here's how I hired a developer. Here's the problem that I'm facing. Okay, pre-sales are ready to go. Who wants to buy? You know, like,

And I shared all of that. And I think it made a huge difference because people were like, oh, here's someone going on a journey that I want to follow. Right? Unfolding in real time. So not only did I get more attention, but I also got a lot of very, like, talented, experienced founders saying like, hey, if you ever need help with anything, like, give me a call. So, yeah.

Amy Hoy did a deep dive with me on copywriting for the landing page, which I then turned into a blog post, right? It's like, here's what I wrote. Here's how Amy and I did it all. I think I even included the recording of the Skype call that we had done. I'm like, here's how we came to the landing page and like all these concepts and everything. And I was just sharing what I learned every week and sharing that journey. And that

has been core to everything in ConvertKit. Like even today, we have a real-time dashboard that shares all the revenue metrics for ConvertKit that anyone can look at, right? That's working in public. One thing that I was thinking about as you were saying this, I'm like, writing is the key. If I could do this thousand words a day, that would, you know, I'm all about teaching everything I know and creating every day and working in public. All that stuff is amazing. Fully, fully vibe with that.

But whenever I sit down to write, so for example, we did our book launch and there's a lot that I have in my head that I'd love to share about like how things went and how we're tracking metrics and all this kind of stuff. But then I'm thinking it's,

It's so niche. It's like I could be making a video called 10 productivity tips instead, which would get like a zillion more views than like a blog post that's going deep on this thing that I've learned that I would love to share. But it's just like if I'm going to spend time on content creation, I should spend that time on content creation that benefits the YouTube channel, which is massively leveraged compared to a blog post. Any thoughts on this? Well, so.

I've heard Nick Huber talk about the way he thinks about things on Twitter at different stages of the funnel. So his business is, or he now has a whole bunch of businesses all around real estate and self-storage and all that. But what he was primarily thinking about is there's some tweets that are more general. He takes like an antagonistic approach to Twitter. He's trying to get some level of outrage or agreement or that sort of thing.

But so he'll have these top of funnel tweets that are about life and work and family and these other things that will really spread. And then further down, you know, the middle of the funnel, he's thinking about, okay, what can I share about business? You know, lessons learned that are broadly applicable, but it's people who care from here.

And then the bottom of the funnel, he'll share like these, I've learned a lot about like real estate tax depreciation and all of this stuff from these really in-depth detailed threads that get read by the right people, right? He's putting out content that, I mean, I've been running a business for a decade and I didn't know a bunch of these things. And so he's going through

down the funnel and writing these very niche things. And he's not worried about that attracting at the top of the funnel. And so he's, he's going through and saying, okay, what do I do at each stage of the funnel? And because the funnel ultimately for him at the time that he was saying this was like getting investors, limited partners for his real estate investing fund. Now he has a whole bunch of other businesses as well.

But getting people who know that he knows this stuff inside and out, they want to hire one of his companies to help with one of these services. Like that is insanely valuable, but it takes these people knowing that he exists. And so that's the approach that he takes. If something's, this should get millions of views, this should get tens of thousands of views. And then this niche content, if it gets a thousand views from the right people, that's insanely valuable. That's one way to think about it. The other way is,

I got to write a thousand words today. What is interesting to me to write down? Like what would be fun? If I'm been weirdly obsessive about like a book launch and how it all went, great, write about that. We're just trying to check the box that we did the writing. The writing doesn't have to be the highest quality or the most valuable because it's also a little bit arrogant to know that, or to think that you're going to create, what you create today is the best possible content that you could create.

We're not trying to create the best content. We're just trying to create consistently. And then we'll let like the future figure out what is actually worth paying attention to. And especially as things are going to be pieced together from 10 different sources and you never know what your team's going to be like, Oh, this thing, it's going to be super valuable. Or say book number two comes out, right? And you're like, shoot, what, what does make a good book launch? I don't know. I wish I'd written that down when I was right in the middle of it.

We run team retreats at ConvertKit and we've run 10 of them now, something like that, twice a year, every year. And the thing that drives me crazy is when I make a small mistake on a team retreat of something that I got right in a previous retreat. It could be a transition. It could be how we set up, um,

like for an all team meeting, some of those. So I have a giant SOP and playbook for what makes a great team retreat. That does two things for me. I don't repeat the same mistakes. And then two, when I bring someone else in and they're like, how do we run team retreats? I'm like, there you go. Right. So if you launch, if you write this book launch article, yeah, I'm going to read it and absolutely love it. And there's going to be, you know, business audience nerds on our level who are like, thank you for writing this. I learned so much. I, you know, I'm plucking this other thing and a bunch of people just won't care.

But then even think book number two, team member comes along and you're like, here's how we do book launches. And you're not sitting down and explaining it to them for an hour because you disconnected your knowledge from your time. And so I think it's hugely valuable to write. And when you write a thousand words a day, you're producing so much content that

Great, write the 10 productivity apps in your video script tomorrow. That's a great point. I love both of those approaches. What is interesting to me about this? I think, yeah, one thing I've been thinking about a lot is

I'm sure you have the problem as well, feeling overscheduled. Like there's always just random shit in my calendar where I'm like, the key thing that I actually care about is to be able to learn and synthesize and share and write and make videos because that's like my jam. And I'm finding myself doing all this other stuff that does not involve doing those things. And I realized recently, even just like flying somewhere to give a talk is taking time away from like

It's not really the core thing I care about. The core thing I care about is to be able to write stuff and put it out there on the internet. And so because my writing time is so squeezed, I'm now thinking ROI for every single thing that I write. And that takes me into this territory of like, well, I could write about topics A to Z that I'm interested in, but actually instead I'll write about topic Y that I don't really care about, but I know it's going to get the views because I only have 20 minutes today to do any sort of writing at all.

and the views of what drives the business and the business supports the team salary. And it just becomes this thing where I've created a prison for myself through overscheduling in the calendar for shit that I don't actually fundamentally care about. That stops me from doing the thing I actually care about and I would love to do. And then the commercial incentives are all like fucking all this up as well. Any thoughts? How do I...

Yeah, what was on my mind as you were saying that is some of my favorite things that I've written have been when I don't fully understand it or don't quite know how to articulate it yet. And I've pursued input from other people.

Right. Like the ladders wealth creation article, uh, has a lot of input from James clear on it because it was like, here's this thing that I'm trying to articulate. And we were at a friend's, uh, bachelor party for, for a weekend, you know, and it's a whole bunch of business friends. And so we're all like nerding out on the essays that we're writing and that kind of thing. Um, different vibe than maybe a traditional. Yeah. I was going to say, that sounds like a great bachelor party. Yeah. That is exactly the kind of bachelor party that I'm into. Um,

But we're talking about these things and he's just asking really good questions and filling in examples. And he's like, well, why is that? Why, like how else, how can we visually describe that? And that pursuit of an idea with someone else, I think is really interesting. So as you're talking to me like, oh, I'm going off to like deliver this talk and it's not furthering my like writing and ideas and learning goals. My first thought is, well, who else is going to be there?

Who would you love to not just catch up over coffee, but like say, hey, here's, you know, I'm nerding out on flywheels for creators. Like you want to grab coffee and talk about that for an hour, right? Because I'm trying to like this essay doesn't quite work. And that kind of thing is really, really interesting. So I would try to combine that. And then I think broadly the point that you're making of like, what is the ultimate engine that drives your business? And yeah.

how do you spend your time there? And you're saying like writing an idea generation is the ultimate thing. And so make sure that that is the core thing on your calendar.

Because ultimately, if you stop making YouTube videos, if you stop sharing ideas with your newsletter, the rest of the business stops. Everything else dies, yeah. Yeah. To be clear, it has so much momentum that it will... It'll take a while for it to die, but it'll still die. But it will. Absolutely. You should keep paying our ConvertKit monthly. Yeah, exactly. At some point you'll be like, wait, this isn't making as much money as it does. Every time we look at a software bill, I'm just like...

Oh, okay. Yeah. Like 40% of it is ConvertKit. Fair enough. We make way more money from ConvertKit than we spend. So yeah, it's totally fine. That's a good way of thinking about it. It just comes down to a thousand words a day. A thousand words a day would literally change my life. Yeah, it's crazy. A thousand words a day would change the life of anyone listening to this. If they've gone an hour and 18 minutes into this podcast, if you're actually listening to this, you actually write a thousand words per day. It's just...

You know, so even saying that, right, I did it for 600 days in a row. I actually ended up getting shingles after that. And so that's sometimes people ask, like, well, why aren't you at like 1200 days in a row now? It's like, well, I ended up getting really sick and took me like six months to recover and all that. But I guess the way to put it is it is simple, but not easy. And so, yes, writing a thousand words a day will absolutely change your life. And that is a very simple thing.

But it is not easy to do and you have to design your day and your week around that habit and that has to become one of the non-negotiables. And that's something that honestly I've struggled with, right? As I go back and forth between, you know, building a team and scaling and all of that. I know that all of my goals would be furthered by writing a thousand words a day. And I still write fairly sporadically right now. Like I haven't rebuilt that. And I think it's because we say things to ourselves like, oh, this should be easy. And

because we're conflating simple and easy. It is very simple and it is not at all easy. And so if you get clear with yourself that like, okay, I'm setting out to do something that is in fact very difficult and I have to design my day around and my week around making sure that this can happen. And this has to become my number one priority in my business. Then at that point,

you can actually make it happen. But if you're like, oh, this will be really easy, I'll just knock it out and then move on, then you'll get to the point where you can't build up any meaningful streak and you won't get the results from that. Any other tips? Any mistakes you made along the 600-day thing that, you know, I feel like I want to commit to that. Okay, I am going to commit to this. Okay. It's writing 1,000 words a day and I want to get ahead of any kind of, what are some obstacles I might run into? And also, are you doing this on weekends as well? Yeah, I did it seven days a week. Okay.

Right, like if it's that important to you. Yeah. The ideas flow seven days a week, why not? Yeah, exactly. The first thing I would say is when you run out of ideas, a lot of people worry that they're going to run out of ideas. And so they say like, oh, I might as well not start. Generally what I find is the more that you write, the more that you have to say. Because you find these threads and you unravel them. The next thing is, even with that, if you're still running out of ideas, think about things that...

think about the content that you're going to consume. That's going to help you find new ideas. So like if you get out of your usual podcasts and start to listen to other things, right. Or the business biographies or, and you have these prompts, right. You're like, okay, what would, uh, you know, if you're reading like John D Rockefeller's biography, you're like,

what would Rockefeller do if he ran ConvertKit? You know, you're like, oh, interesting. Well, he'd probably have all these backdoor deals and he's probably acquiring other companies. You know, like, oh, blah, blah, blah. Somehow he creates a monopoly and I don't know how it works, but you know, it's a fun exercise. Right, so you can have these prompts to dive into. But like, I listened to Ryan Holiday on Jocko Willink's podcast. I don't normally listen to Jocko's podcast, but I love Ryan's work and so I was like, great, I'll listen to this. And it was a really interesting take. But Ryan said this thing about, um,

He was talking about how Tim Ferriss in the early days of like audible, really getting traction started buying up the, the audio rights to a bunch of books. Cause you had this weird moment in time where audible was getting traction and publishers did not value audio rights. So like Josh Kaufman, who wrote the personal MBA sold the publishing rights to his book as you normally do. Uh,

the publisher didn't want the audio rights so then they sold it to somebody else and then it kind of bounced around and then they were going like he he was like i don't like this and so he asked can i buy them back and so for like ten thousand dollars or something he bought back the audio rights the personal mba uh

published it himself through audible audible had this crazy distribution thing where like the more copies you sold the higher percentage you got of every copy sold and it ended up it got to the point that at one point josh was making like 50 to 60 thousand dollars a month uh off of exclusively the audio version of the personal mba nice tim ferris understood this

and started going around buying the audio rights to any book where the audio rights weren't valued so um you have the obstacle is the way on your shelf uh tim ferris owns the audio rights so the obstacle is the way um and he did this for a whole bunch of books yeah and i feel like the seneca letters one of the stoic letters yeah that's the one yeah um yeah so he he's done it for really a lot because there's this moment in time where audio rights were

radically undervalued for um what they got and so it made me think like listening to that episode one i had been around like i knew tim and i knew ryan back then and so i remember talking to like i remember hearing that and seeing it all unfold um but what it made me think of is this phrase of like who's playing chess when other people are playing checkers

And now that's turned into a prompt for me of like, okay, where in my business am I playing checkers when I should be playing chess? And then what other stories can I share on my podcast or other things where someone is operating at that level? And

Like I wouldn't like that is now a consistent thing in my journal, that phrase. What would it look like to play chess here? You know, who's playing chess when others are playing checkers? And I only got that because I listened to a podcast outside of my normal, like my normal flow. So when you're running out of ideas, I guess two things on that. When you're running out of ideas of what to write about, switch up where you're consuming information.

And then the second thing is try to have these consistent prompts that you come back to that lead you to interesting places. And so two of mine are, what would this person do if like tackle this problem? And then another is, you know, what would it look like to play chess rather than checkers? And if you end up with a stable of like 15 or 20 of those, then you can go like problem or story and then prompt. And that will result in some interesting thoughts. Some of which hopefully will be worth publishing. Yeah.

So you write 1,000 words a day, but presumably you don't publish 1,000 words per day. What does the publishing segment look like? I mean, it's entirely up to you. I would just pick something and stick with it. I think publishing a newsletter once a week or an essay, sometimes newsletters are a little too low quality, and I'd rather people focus on flagship content. I struggle with that back and forth of staying consistent versus being really, really high quality.

I would just say pick a frequency and stick with it. And it has to be, you want it to be a point where you're not too frequent so that you can't hit your quality bar. Some people are like, I'm going to write every single day. And then I'm like, well, you're not Seth Godin. You don't have that.

like level of input of ideas and, and all of that. So I think once a week is a good consistent cadence, it forces you to stay on topic and explore. Um, but then you need something that you're really pursuing, right? Like, uh, some thread that you're trying to pull on and unwind or like a book that you're writing or, or like a meaningful project. Um,

otherwise it it offers a lot um so I've got about four different book ideas that I want to sort of pursue me too and I love the idea of I was speaking to Mo Gowdat about this who wrote Soul for Happy and he he has about six different book ideas and he says each day he does two thousand by the day he said I just pick whichever one takes my fancy and I just take her away at it do you do something similar where you like or would you recommend that or do you think it's helpful to have just one thing that you're working towards

I think no matter what you do, it's important to have a way to capture the ideas that are sparked. Because sometimes, like I have four different book ideas, I think, and they sort of overlap. Like, is it this book? Is it that book? And, you know, what order should they be published in? And so the biggest thing is get the ideas down on paper and then, you know, either edit it yourself or hire an editor. Someone else will come along and be like, oh, no, no, no. This story is actually the thing that we're going to use here. We're going to flip the whole thing around.

that's like the order of the ladder to wealth creation article is very different after James got his hands on it. It was like, no, no, no. Like read the whole thing, you know, but like, let's, let's represent it like this. So I would be in the camp of just right. If that's what works for you, unless you're so scattered that it's not working for you. And then like force yourself to, to stay consistent. Yeah.

But otherwise, like as you're writing one thing, make sure that like the documents and the structure for the other thing exists so that you can be like, oh, this does belong over here and you have a place to put it. And so it's not lost or wasted. Sick. This is so good. Okay, I'm going to commit to this. A thousand words per day. That's the thing. That is the one. You were asking for tips. One other thing is...

There are days that you can't, for whatever reason, or shouldn't write a thousand words, right? Where, you know, it's like, okay, I'm going to go, I don't know, like with my partner, I'm off to go do this thing. I'm going to be entirely focused on time with them or whatever. And so people are like, what do you do? It's like, oh, just write more on the bookends.

you know, build up and be like, Hey, uh, you know, for this holiday weekend, I'm not going to write. And so I guess for the preceding week, I need to write 1500 words a day to get ahead and, and plan ahead like that. And then also look at your calendar and say like, Oh, it's going to be really hard to hit, uh, to like, to write on these days because of whatever is happening. And so I'm going to make a plan for it right now. Ultimately, like,

you know i'm going to get up earlier that day i'm going to uh write in advance you know any of those things yeah and there were days that i like forgot to write and instead of being like oh i broke the chain and all of that and getting upset about it i would just write double the next day yeah so like the goal is 600 000 words in 600 days not you know literally a thousand words a day yeah okay that's nice yeah because it gives you the flexibility while also being able to

maintain the chain as it were it also helps you think of it like a job where it's not day by day it's like the the big picture you know if it was like hey i have to keep this factory moving all the time like with this level of output you know but we want to take this week vacation no problem just increase the output by 50 percent for the preceding week or two weeks yeah and you're good to go easy simple not easy simple not exactly yeah simple not easy um

What are your thoughts on a personal blog broadly? And I ask because, so I like your website. I like nathanbarry.com. It feels personal. It's good vibes.

I'm unsure what to do with mine. My website, aliabdal.com, it started off as a bit of a personal blog. It's now morphed into like, well, this is good legion for the business. And so we should get ghostwriters to write a shit ton of articles about how to grow on YouTube because then that links to our YouTube, of course. But then it sort of loses the charm of like a personal blog. And I like the personal blog from an artistic sense, even though it may not make sense, may make less sense from a commercial sense. Right. I wonder what it, yeah. Do you have any thoughts on this?

I don't have that exact problem because I have ConvertKit and NathanBerry.com fairly separate. Like ConvertKit is more of a publication. And it's clear that other people are writing the vast majority of that content. Now if you're trying to split it and it's like, okay, one thing would be like, oh, we'll spit out another site. It's like, well, but then I'm going to have to build domain authority for that new site. And you're like, don't do that. From an SEO perspective, I would think of it like maybe you have these flagship sites

that are really going deep on and going to rank very, very well for, you know, how to grow a YouTube channel. These high intent search terms that are going to be worth a lot of money to you. Yes. Right? This will turn into a $500 course purchase. This will turn into, you know, and someone's trying to do that. And I'd build those funnels really carefully. And then, like, I wouldn't do the ghostwritten, you know,

one-off random things to rank because i think google rewards the flagship articles much more yeah get tons of ghostwriting help on those right like make them amazing yeah it should be the brain dump of your ideas and then have a great editor like really go through it so this is something that you're really you know really proud of and can link to and keep updated for years yeah

But I would keep the personal stuff going. I think that's something that's missing from the internet right now is like the classic, this is what I'm thinking about. And I'm just following that. I wish I did it more. I do it a decent amount in my newsletter. But yeah, like what's something that I'm trying to do is like scale it back just like one notch on the level of polish so that not everything has to be a fantastic essay or something else. Like I want that more raw feeling and less marketed. Yeah.

But that's just because that's what I want to exist on the internet. Yeah, same. I really like discovering a personal blog. And it's so nice.

Yeah. One thing I like less about yours is the fact that your podcast blog post... I know, me too. It drives me crazy. And I'm just like, oh, I just want to read the Nathan Barry archives. I don't want a 078 interview with Sahil Blu. It's like, I would love for that to be separate. There's a bunch of those things. I'm like... And I have the same issue with mine. It's like latest articles. It's like they're all podcast episodes. I'm like, oh, it's not the vibe. Yeah. And it's like...

What I want, which of course I have people on the team so I could just pay to do it. Actually, it's kind of a weird thing. I have a lot of people on the ConvertKit team and I don't really have people on Team Nathan. And so you end up with this like, oh, the WordPress install is in the ConvertKit WP Engine server and so they make sure it's updated and all of that. But it's like, they have other things.

But yeah, I want the site to be like, these are the flagship essays. These are the recent random musings. I want it to be the kind of site that it's easy to get lost in, where you just go down the rabbit hole and binge it all. But yeah, I would definitely... What I want more people to write about is...

what they're most interested in. And then like the behind the scenes, the content, like I can get the 10 productivity app tips, a handful of different places. Yeah. But like, I want to read the like obsessive book launch things or like, here's how, like I loved Tiago Forte's content about how he built out his garage studio, you know? And it's not like in theory, this is how you should do it. It's like, this is what I actually did. Um,

and so i just love that like the the show your work kind of things um because i want to follow i want to follow the person more than i want to follow the advice yeah yeah i think one of the one of the issues and i think maybe this sort of the nikkuba funnel that you mentioned solves this but one of the issues is when

and I guess every media outlet has this issue where it is the BuzzFeed 10 productivity apps stuff that will get the clicks and get the views from a mainstream audience even though that's the stuff that's just like objectively less interesting and the more interesting stuff does not get those views but maybe and I like the way you phrased it sort of

views from, I guess, quote, the right people. If you're trying to attract an audience of, like if I want people like you to read my blog, someone like you is not going to read my article about 10 productivity hacks because like, why would you? But if I said, if it was an in-depth look at how my book launch went and like the numbers behind it and the screenshots and how we tracked things and fathom and then the graphs and shit, like you would read that. And you're the sort of person that I would like to be part of my newsletter because it's like, you're Nathan Barry. Yeah, it's like the people who are executing at a high level

will read niche stuff not whereas the there's just this sort of separation like the mainstream and it sounds weird to kind of say this because i don't want i don't want people listening to this to think that i'm ungrateful for the audience audience and stuff but it's just like someone like you or someone like tim ferris would read a very different blog post right compared to a random person in the audience who doesn't have their own business for example when the great thing is that you can segment audiences right and i think that people don't do that enough right

I've written a lot about how to earn a full-time living as a content creator. That's a topic I'm very passionate about. At some point, I feel like I've written enough about that. And there's enough written on the internet by the 0 to 60,000 or 0 to 100,000. The gap that I felt like was there in the market is like, okay, you've done that. If you understood audience building and leverage and marketing and everything else enough to get to 100,000 a year in revenue,

I bet with the right steps, you get to $500,000 a year. And what I wanted to write about is, okay, what happens now? You're not making $500,000 a year more than you ever thought possible, more than anyone else in your family, more than, you know, all of these things. What do you do? Because there's real problems that come with that. And I wanted to write about that topic, but I knew...

That's not what you write about to a 50,000 person, 30,000 person email list. And so what I did is I said, okay, I'm going to create my own paid newsletter. It's only paid so that there's a little bit of a barrier to get into it. I don't really care about the money from it, but I called it my secret money newsletter. And I said, it's a hundred bucks one time to get on the list.

Rather than committing to like writing every single week, I made an email course. And so I started it when I had like six emails written out and you'd get one every Friday. And then whenever I felt inspired, I'd add another one. It's now 17 emails long and people just get all the emails and they wait at the end until I added another one and then it'll be 18 and so on from there.

But it led me right to a different audience without the caveats. Because I just said like, look, if you're making less than $200,000 a year, this is not for you. If you thought for even a second about, is $100 worth buying this thing? This is not for you. And it's been so much fun because I segmented my audience and I'm talking about like, okay, what are your favorite things you've ever splurged on? Right? Like a VIP tour at Disneyland for like your family and friends.

One audience would be like that is absurd that you spent four thousand dollars, you know or whatever You're spending five hundred dollars an hour for someone to help you cut the lines at Disneyland But then some other person is going to be like this is amazing. Like how do I you know? How do I book that? What other tips do you have and? Even little things like there's people in my life Who have helped me reframe things around money in a really important way and I want to be able to pass that on like my friend mark

at one point was talking about investing. Like I assume that once you get to a certain level, then like investing, it's really complicated. You have to have like financial advisors and you have to, you know, you're like, you have all these new opportunities. And so it means all this stuff. And he's like, look, we were talking about it and he'd built up, I think his Vanguard investing account about $5 million from his creator business, just continually, you know, for a decade putting in

hundreds and hundreds of thousands of dollars a year just funneling all those profits in. And I was like, but don't you have to do more complicated things? He's like, no, the Vanguard account functions the same at a hundred grand and 500 grand and 5 million. Like it just works the same. Like it doesn't matter. It's like, well, isn't that a ton of money to keep in Vanguard? And he's like, no, think of the grand scale. Like they're like $5 million doesn't even register for that. You know, they probably have billions of dollars in single Vanguard accounts. Yeah.

And in another moment, when ConvertKit first got a million dollars in our checking account to operate the business and all that, we'd saved up to that point. And I asked them this software founder's Slack group, like, what do I do? What do I need to set up? This is all that. And this guy, Ian, who runs a really successful SaaS company, just said, like, Nathan, a million dollars is a very normal amount of money to have in a checking account for our business.

And I was like, what? But don't you? And I realized like, oh, yeah, that's just how businesses operate. So there's these conversations around money that I wanted to be able to write out. And I wanted to do it in two ways. I wanted to do it where I can create something once and it continues to work for me forever. So I'm not on a content treadmill and where people are like, Nathan, where's this week's essay or something like that?

Uh, and then the second thing is I wanted to do it to a niche enough audience that they would care about and value the same things. And I wouldn't have any of the, like, here's Nathan bragging about something related to money. Right. And so I think that tool of like an email course or a private section of your blog or something else is really great for that because you can explore what you care about, niche it down to only the people who care about that. And those are also my favorite replies, right? Like, uh,

I'll write one on like my favorite splurges once you have money. And then I just say like, Hey, what are your favorite splurges? And people will reply and say, Oh, this one time I, we took another couple on this, uh, like, Oh, it was like a bikes and barges cruise throughout like a river cruise throughout Europe where you're like,

rode your bike all day from one city to another, like stopping. And then you like got back on the, you know, river cruise boat and stayed for the evening and like repeated over and over again. They're like, it was an amazing experience. And yeah, it cost, I don't know, $10,000 or some really meaningful amount of money, but they're like, but it was amazing. So I love reading all of those stories and getting the replies. And I feature the replies in future editions of the newsletter. So it makes this little community.

So that's the way that I handle it of like being able to write the niche topics that I care about.

and just segment it to a niche audience. That's really good. I'm going to sign up to the secret money. Yeah. Cause I, I heard some, I've heard or read somewhere, might've been one of your podcasts. Is this the same newsletter where you, where you reveal like personal income details and all that kind of stuff? Yeah. I have about once a year, I have like an update of this is my net worth and where I invest everything. Interesting. Yeah. Cause I want to write about this stuff. The other thing is I want to read back.

All my own previous stuff, right? I write a year in review blog post for the last, I think I'm 12 years in of writing, you know, you just nathanberry.com slash like 2012 dash review, 2022 dash review. You'll get there. And I'll even pull up stuff. Like I want to show someone a photo the other day. And I was like, I know the URL structure of my blog so I can get to that really quickly. But those are written for me.

Because I'm like, oh, what was I struggling with in 2013? What did I value in 2017? Where did I go? I'll go and look through all of that. Oh, there's the kids when they were really little. There's all these different things. And so, yeah, I'm just...

creating content for me and trying to have that archive, I just also put it out on the internet because I guess I'm weird like that. That's cool. That's very cool. Yeah, because I've been doing these videos for the last five years or so about how much money I make on YouTube each year and they're getting more and more absurd. And I'm kind of like, I don't know if I want to continue doing these

In a way, it does sort of paint a target on my back to some degree because people might think that business revenue is equivalent to personal money in the bank, which it's really not. You don't need to get kidnapped outside your flat or something. Yeah, that's the sort of thing. I don't want that to happen, especially if I get married and have kids and things. But I do like the idea of being public and transparent about stuff like this. There is a point that it becomes entirely unrelatable. Yeah.

Um, and so that, like, I, I wonder the same thing, um, like for ConvertKit, you know, we're public with our metrics, but our business has gotten a lot more complicated or sophisticated. And so now like our public dashboard only shows, you know, one revenue line and we have three and, you know, and, and then I'm thinking about like, okay, is this still serving the same, same journey? So yeah. Yeah. Sometimes they, yeah. It's, it's a balance. Um,

And I don't know. And especially because you're right, people don't understand money. They're like, okay, oh, you made $5 million off of this. That's absurd. So you probably took home like $4 million and you're like, no. No. I wish. That is not how it works at all. So yeah, there's definitely a point where you would stop. And one thing that I would say, because I've struggled with this,

just to make clear yeah is you don't owe this to anyone right there's a point where if you create content for a long period of time people will start to treat you like you owe them that you continue to create that content yeah true

And you don't like do it for as long as it serves you in that way. And you can change people and be like, Oh, why are you not releasing that video anymore? Like, you know, and you're just like, look, it wasn't interesting to me. It wasn't serving me or the business. And, you know, if you need that roadmap, look at the last six years of this video that I put out. I also wonder about, this is kind of a struggle for me on like how much lifestyle things to share.

Here's my fancy house. Yeah, here's my fancy house. Or if you charter a plane to go somewhere, right? Or, you know, who knows, private tour at Disneyland or like all these things, a fancy car. It's a weird thing where I don't, on one hand, don't feel like sharing any of that stuff. But on the other hand, if you do share it, like it drives like lots of attention.

Right. Like my friend Dan Martell just bought his own plane. Right. And he doesn't live that far from me. Like right. You know, it's like a 10 hour drive, you know, but like commercial flights, it's ridiculous to, to get there where he's up in Canada. And like Kelowna. Kelowna. Yeah. I've been trying to plan a trip there, but it's a fucking nightmare to get to. It's really, really difficult. I want to get him on the podcast and like his new vlog and all this stuff. Yeah. Yeah. It's so much good stuff. And so I imagine, I haven't talked to him about this, but I imagine when he bought the plane, he was like,

You know, there's a whole thing of like, oh, should I share this? You know, like that puts, that's a different level of wealth. But then on the other hand, in sharing it, he's getting a whole bunch more attention because there's someone scrolling through Instagram like, he owns a plane? Who is this guy? Right? And they dive in, they find his stuff and they end up like using his advice to grow their business and all of that. So that's something that I struggle with a bit is at what level to share that. Because on one hand, I...

like live a pretty simple, straightforward life on a farm in Boise. And then on the other, like there's things that I spend absurd amounts of money on and I'm, I absolutely love it. And so it's like, oh, you know, like do I need a marketing photo like that? You know?

not that i have a lamborghini but if you did that or like a ferrari or something right you could get a lot of marking mileage out of that yeah and i'm like i don't know so you got to figure out what what your brand is and and what you want to share yeah yeah at one point i was doing like you know i did a a tour of my apartment in cambridge which was cheap it was like 1500 pounds a month rent

Or the rent equivalent. And then I moved to London and I moved into a fancier one. And I was like, okay, let's do a clickbait title. And even though it was renting, we called it like my $2.5 million apartment tour. And there was something about that. I was just like, oh, God. And like, now this place is even more expensive than that, but I've not mentioned it. I haven't really talked about the price unless someone's explicitly asked me on the podcast. And I like...

The idea of being... I like the James Clear approach. Kind of. The James Clear approach is basically I want to be known for my ideas. I don't want to be known for my face or like my lifestyle or anything like that. Making fuck tons of money. But at the same time, I do like... I vibe with your thing about the whole transparency side and sharing and, you know, the fact that like...

Dan Martell talks about how he has a plane and be like, I'm way more likely to follow his stuff and I'd be interested because I'm like, oh shit, I'm not thinking of that as him bragging. I'm thinking of it, that's really cool. That's inspiring. But I know that there are lots of people out there. I speak to my grandma. I was chatting to her yesterday and she was like, Oli, please stop talking about how much money you make.

And I was like, oh, but it's inspiring to people. And so many people have said to me that like, because of that video, they started a YouTube channel. And she's like, yeah, but you know, everyone else out there is just sort of feeling, they're not feeling inspired. They're feeling like hurt because they haven't achieved that. And I'm just like, oh yeah, I don't know. I don't know. Yeah. And it's challenging, right? Because you don't know and you can't control how someone's going to react to your content and whether someone's going to say like, uh,

Like I feel envious of that or someone who goes, Oh, I could do that. Right. So years ago, actually before I published the app is a handbook. I was wanting to write and I had like kind of start and stop and, you know, work on this ebook. And then on the same day, these two guys, uh, Jared Drysdale and Sasha grief published eBooks, self-published eBooks to small audiences about design.

And it was pure chance. They launched both of these on a hacker news on the same day. Sasha had this, like, it was like a design case study where he walked you through how it went and he sold it for, I think $6. And then if you wanted to buy like the one with the Photoshop files with it, it was $12. So we had these two, two prices and Jared sold his book for $39.

And it was just that one price. And it was fascinating to see both of these happen on the same day. And it was like, you know, you're like looking at them ranked in Hacker News and you're like, that's, that's interesting. And then Jason Cohen, who's the founder of WP Engine, invited both of them to come on his blog and say like, write a guest post about

about your pricing model, how your launch went, and why your pricing model is better than the other person. That's fun. And so it was great fun. And so I read both of those. He published them one after the other. I read both of them and thought a couple things. One, you can make money self-publishing. Two, these guys are just like me. They're designers with small audiences, self-publishing a fairly niche product.

compared to like reading about Jason Freed, who's like, oh, look, we made 500 grand self-publishing. You should too. And so it really resonated with me. And I've heard a lot of other stories of people saying like, okay, like I'm paying into the story. And like, there's a black woman like me who accomplished that. There's this person who lives in my country who accomplished this thing. Right. And seeing that representation. And I think that's just really, really cool. Cause you can see it and go like,

that could be me. And so I really like the idea of sharing the stories ultimately and being like, this is the scale that it could get, right? Like you could build a business to $5 million a year, $10 million a year. And it's possible because that's the power of audiences. And that's why I love telling all this because otherwise people don't realize how far it can go.

But then it's a trade-off. You just don't know how people will respond. I haven't really heard of examples of people having truly negative outcomes, you know.

Yeah, the Tim Ferriss blog post is scary, but other than that. That's true. That's true. And that is, right, that is another level. That's a whole five levels up from where I am, for example. But if you think about it, I don't know how many copies of his books Tim has sold, but if we go to James Clear, for example, he sold 15 million copies of Atomic Habits. He has, I think, the largest single author newsletter on the internet. Yeah.

And that's pretty wild, you know? But he doesn't seem to have, like he seems to stay much more in the background. Yeah, but also like most people who have read Atomic Habits probably don't know what he looks like. So his like profit per unit fame is quite strong. Yeah, you know, so we host a conference every year called Craft and Commerce. And so we've had a lot of big names, you know, James has spoken at it and Seth Godin and...

One year we had Casey Neistat come out to speak. It was 2018, I think. 2019, somewhere in there. So he was pretty close to the peak of his vlog popularity and all that, putting out a ton of content. It was before he switched up his stuff and took a little bit of a break. And so he arrived at the airport in Boise, Idaho. And someone on our team went and picked him up and all that. And he was starting to get mobbed.

Like, and you know, just like waiting curbside in Boise, right? People like Casey, Casey, you know, like trying to get his attention and all of that. And, uh, you know, so watching like that level of recognition and getting recognized very randomly and, and, uh, that level of fame was one thing.

And then the next year, Mark Manson came out to speak. And the subtle art had sold an absurd number of copies, was top five New York Times list continually. And Mark attended the entire conference.

Like not only was he at the speaker's dinner, but he and his wife were like, they went to workshops. They just like, Mark's a very chill guy and they loved it. And then he got up and gave his closing keynote. And I think a bunch of people went,

I had lunch with that guy. That's Mark Manson. But it's the difference between YouTube where your face is on everything and you have that level of fame and the book where you're like, oh, I could think that's an amazing book and I have no idea what Mark looks like. Now, what I wonder is over the last year or so, at least as I've noticed it, Mark has a lot of stuff, a lot of content that he's putting out with his face on it. And so I'm always curious. I wonder what thoughts you have on it of like that...

Is Mark giving up something? Like he had the level of fame and name recognition that maybe so many people want without the face recognition. I don't know. Maybe he wants to get recognized on the street. Maybe there's another type of content that he wants to truly have his face. I do it. What do you think? Yeah.

Yeah. Um, so I, I had dinner with him in LA a couple of months ago. Um, and he was very kind enough to offer a blurb for my book, which was, which was very nice. Uh, super chill guy, very friendly. Um, it was interesting how, because, because I kind of said to him that like, he, he is where I, I aspire to be in terms of like the book stuff and that book still sold stupidly well, et cetera, et cetera. Um,

And he seems to be trying to be a YouTuber and succeeding fairly well at being a YouTuber. And he kind of said that like, you know, with all the traditional media stuff, Hollywood film and everything, that it reaches more people, it's more fun, and it makes more money to just make YouTube videos. I was like, okay, that's interesting. Yeah.

And he was kind of saying to me that like, don't peg your self-worth on like whether you hit the New York Times bestseller list or not, because you'll do it. Maybe, maybe not. Like you'll change your Instagram bio and your Twitter bio and life will move on and it'll just be a minor blip and you won't really care. But it's like the work is the thing.

Right. And so I was like, that was, it was quite reassuring. Yeah. But I don't know how he feels about being recognized in public and stuff. Yeah. Do you get recognized in public very often? Yeah. Like a few times a day if I'm roaming around London. Okay. I quite like it because that feels like a good level. It's educational content. So people are like nice about it. And like, it's only really nerds who follow my stuff. And so like, chances are I don't want to talk to them about something. Yeah.

but I wouldn't want it to be like in an entertainment kind of genre where there's like a line of a hundred people trying to get to you and you're like trying to be like, yeah. Um, I think it's all, yeah. Different, different genres as well. Like who's it? Um, MKBHD, Marcus Brantley was talking about how he would, you know, he was at this YouTuber event with like Lele Pons or someone like that. And he sort of,

And she walked out the airport and there was like a mob of like 100 people just waiting. He walked out of the same airport. No one recognized him.

and he's got like 15 million subscribers is like the world's biggest tech youtuber yeah but also the sorts of people that walk that watch his channel are not the sort of people that would like to line up outside someone's hotel room to figure out oh my god marquez is here so i think there's what outfit is he wearing today um ladders of wealth the ladders of wealth creation a step-by-step roadmap to what's it to building wealth um

Yeah, so I guess the first one is, yeah, there's these four different things. I wonder if we can just sort of talk through these in turn and just love for you to riff on these. Yeah, so in the ladders as well, they break down like four different ladders. You can climb as high as you want on any ladder, but they are, I guess some are ultimately taller than others. So to run through them quickly, time for money, your own services, business, productized services, and then ultimately selling products. And as we think about

skills. The skills that you have to learn are pretty different on each ladder. So time for money, you might think like, what skills do you have to learn for that? But you know, going back to the job at Wendy's, there's a lot of people who did not learn the time for money skills. Those are like being able to follow a process, doing what you're told, showing up to work on time, showing up to work sober, you know, like some of these, these things that

we might take for granted, but like for a lot of people, you have to actually learn that to be reliable and to be consistent. And so in that ladder, you're going to start with like an hourly job. You know, it could be landscaping, could be Wendy's, could be something else. And then later move up to a salaried job. And you're going to have a pretty...

Big range within that, right? There's plenty of salary jobs that would be on that ladder that could get to $200,000 a year, you know, maybe as high as a million dollars a year that that could be within that. The next ladder I think is where things start to get more complicated, right? That's like having your own services business at the basic level. You're talking about operating as a freelancer, right? And so that's where I'm just, you know, trading time for money. Both of these first two ladders are time for money.

And, and there's a one-to-one relationship there. And, and so, but in the services business, I have to know how to form a company, right? I have to fire the, uh, file the paperwork with the government. I have to know, okay, I got to work with an accountant. I can't just use like TurboTax or some other software, right? There's some more stuff for that. Um,

How to write contracts, all of those things. So the first rung in that ladder is really hourly work. Hey, I'll design your website for $50 an hour. I'll show up for this amount of time. I'll mow your lawn for $25 an hour, anything like that.

The next rung in the ladder is when you start to charge by the project. And this is where things get interesting because now you have this big disconnect or a possible disconnect and a leverage point and you've separated time for money. Instead of I will design your site for $50 an hour, it's I'll design your site for $2,000 no matter how many hours it takes. And now we've introduced leverage and you understand leverage

A lot of people are like, oh, leverage is good. And I have to remind them, leverage is neither good nor bad. It just is. And it just amplifies what already is going to happen. So if I am investing and I borrow money that gives me leverage to be able to invest more, that...

means that I'm going, you know, if the stock goes up, I'm going to make more money than I would have otherwise. And if the stock goes down, I'm going to lose more money than I would have otherwise. So in our web design example, maybe it takes me 10 hours and I end up making an equivalent of $200 an hour. Maybe it takes me 50 hours and I make far less than I should have, you know. So that's the first thing. And once you disconnect time for money, then you start to get leverage. And then the last rung on that ladder, on the services ladder,

is really like managing a team and that's a whole new set of skills and you can get even more leverage so at each of these two ladders you can make a lot of money and you need to learn one set of skills or i guess differences of skills and you can get increasing amounts of leverage and then really as you move across uh to other ladders then uh like product services i think it's really interesting i guess to run through them quickly the the

Product-based services are interesting because you're trying to take something that was totally flexible and you're saying, let me standardize it more and more so I can move more people through the process. It's easier for team members to provide this value. HeyFriends, for example, is a good example. If you explain really quick how you think about that. HeyFriends is an agency that we're building with a couple of partners. Basically, it's...

If people sign up and they pay large amounts of money, like I think starting at $14,000 a month, then the agency will do all of the work to make them banger YouTube videos that kind of look like mine, i.e. they're talking to a camera, talking head educational videos, where they're talking to a camera,

where all like, for example, Nathan, if you wanted to do YouTube through Hey Friends, all you would have to do is show up and talk to a camera for like a handful of videos. We would do the titles, the thumbnails, the ideation. We would say, Nathan, we've analyzed all your work. We figured out your style. We figured out your goals. These are the videos we want you to film. You would just record to a camera, send us the files, and then our team would do all of the work in turning them into sick videos with great editing and good vibes and deal with all the analytics and everything. And so that is a productized service in that way.

We have basically converted my process for making videos into a standardized playbook that team members can follow. We'll plug in your goals and your brand aesthetic and everything into that. And then we can then sell it out at a discount compared to what it would be to create that completely from scratch. Yeah. Yeah. So it's no longer perfectly bespoke, but...

In a lot of ways, it benefits from the fact that it's not because you're being able to take the wins that you have across clients and things you learn in the process and go from there. What's interesting about productized services is that you usually go from selling them one-to-one. I'm not taking you out to coffee and then saying, oh, here's all we can do. That is one skill set that you need to learn in a services business. But as you go productized, it's like,

oh, now I need to disconnect the sales. I need to be able to sell through a sales page. And so for that, I have to learn copywriting and design and maybe WordPress or ConvertKit landing pages or whatever else to build up, like to make that sale without my time. And then on the services aspect of it, we're trying to standardize as much as possible there so we have as much leverage. So in each case, we're like, it goes from very connected and then we're just gradually trying to disconnect. Okay.

okay, how the service is delivered, how it's sold, and we're getting further and further apart. Because in each case, that allows for more leverage. And then as you take that further, Hey Friends is a recurring offering. And that, oh, that's another point of leverage. Because wait a second, I sell this one time, and so long as I keep delivering value consistently, then they're going to stay on. I'm not having to make a new sale every single month. And so that's a huge thing. And then the final ladder is,

is really where you're going to pure products. And so that could be something as simple as an e-book like we've talked about. It could be like a WordPress plugin. Even like an Airbnb is a product that you've made, right? It's disconnected. And so like WordPress, Shopify, Airbnb, all of that are products inserted into an existing marketplace, right? Like I own several Airbnbs.

And I don't think about how do I market them? I think about how do I make my listing good? And then Airbnb takes care of all that deal flow. So that's an easier product to make than a product where you have to like create and package and sell and then continually market and have your own, um, you know, continual sales to scale that up. So that, that, you know, things get harder and harder on the ladder. And then ultimately I think that, um,

Software as a service is one of the most difficult things to do, but also one of the highest value. Because when it gets implemented into a company, it sticks around for a very, very long time. And then you see them get ridiculous multiples and all that. And then ultimately, I think the hardest thing to build and the highest possible leverage is a marketplace or a social network. And what's funny is a bunch of people start there. They're like, I have this idea for...

you know, a dog walking service and blah, blah, blah. You know, and you're like that, that's a two-sided marketplace. And so you have the skills that you should be operating like on ladder one, rung one. And you're saying like, let me dive all the way in and try to tackle the, like the absolute top of the last ladder. And that's why people really struggle because they,

They try to bite off way too much and they try to make a leap that requires learning, you know, 50 skills instead of iterating through one skill at a time. Yeah. When I first read this essay, I thought it mapped quite well into what I was doing with my life. So like I started off trading time for money when I was like 12 and doing like

private tutoring for like four pounds, five pounds an hour. Then I moved into selling services, which was like web design services, where I was charging by the hour. And then moved into charging by the project and didn't really make very much money from it. Then slowly started dabbling with the product thing. So my first proper business that was successful was sort of med school admissions business, where I was doing, selling in-person courses.

teaching people how to get into med school. And initially I was doing them all myself, but then we sort of turned it into like a process that like I could hire people to follow. And then I built a sort of software medical school question bank because I knew how to code and combine forces with my brother. And then that was a product with some level of recurring revenue. And then the YouTube channel came and the courses on the, on top of that. And so now it's like almost everything we do, we try and do in the products camp. Um,

And I don't like going back into productized service. It's like, hey, friends was nice because we didn't have to do anything for it. So to us, it was like basically a product. But the team is managing everything. And we do have a bit of a service-based offering for our YouTuber accelerator, which is a little bit service-y, but that's more like a product, but just like good customer service. And so now it's just like having gone through the three different ladders and onto ladder four, it's like that is where the true gains are to be had.

Yeah. Yeah, depending on the goal. Like, I actually was fairly against services as, like, an ideal business. But I think the more that I've gotten into that world and paid attention to it, there are some very, very, like, truly fantastic services businesses at both crazy scale and much smaller. Like, I always thought it hit some limit. But after seeing, like, behind the scenes of some of these services businesses that are doing, like, 10 to 20 million a year in profit...

Then you're like, oh, okay. So what's really interesting about that is a lot of products, you end up with a low average revenue per user. So if we take your productivity average,

consumer app. Yeah, if we went that... It'll be a low average revenue per user. Yeah, so you might be making $100 per year per user, something like that, right? That's very different than if we're charging $10,000 a month for an agency service, right? That's $100,000 per revenue, average revenue per user. And so it takes really a lot of individual app subscriptions to add up to, you know, even a handful of the agency subscriptions. And so...

it really depends on your goals, right? If you're trying to maximize enterprise value, basically the equity value of what you could sell this for, then you might really focus on the app side. But if you're trying to maximize cash flow, both short and long term, then the agency could be a much better model. And then especially realizing that they're not mutually exclusive.

This is something that Silo Bloom is very good at, right? Where he's saying, oh, I'm going to start this and this and this. And he asked the question, like, what would have to be true for me to be able to run multiple agencies without that being a huge drain on my time, right? Like for him, protecting his writing time is the most important thing in his business. And so he's like, great. I just can't run any of the agencies.

And he and I have an agency together called Paperboy, which is a newsletter growth agency. And we collectively, like he and I each spend maybe an hour or two a month on it because we hired a CEO. And so when we mapped it out from the beginning, it was like, okay, well, it has to be true for us to focus on our core thing, have a feed into it, and then still provide this really valuable service. And so it's all on how you design it. One thing that you've been writing and I guess thinking about a lot recently is

The Billion Dollar Creator, and I think that relates to the idea of sort of flywheels when it comes to creator stuff. I wonder, what is all this stuff? Yeah, so the idea behind The Billion Dollar Creator, which is another one of these essays that I wrote, is if you have attention, which creators are so good at getting attention, like you get to point it somewhere. And so what's the highest ROI place to point that attention?

A simple example, you know, most creators are saying, okay, let me sell an ebook. Let me sell a course, affiliate products. And we're blown away, right? That you can make $1,000, $10,000, $100,000, a million dollars off of an audience. And like, this is amazing and mind blowing. But as people who are always trying to push the limits and know what's possible, we're like, what, what else could we do? And what I wonder is, could you build a hundred million dollar business?

So an example that I love is this guy, Mark Sisson, who he created a blog called Mark's Daily Apple, maybe 2009, 2010 time period. And if you think about when the paleo diet started to really become popular, they were focused on recipes and content in that niche. And he built this blog to the point that I think it was making over a million dollars a year, which is just absolutely incredible.

And you might think like, okay, that's the pinnacle of what you can do with a blog. And what Mark ended up doing is he said, what else can I offer to this community? And so we thought like, wouldn't it be really nice if you could have a, um, like a mayonnaise or a ketchup or the things that match the paleo diet. And so he started his own company making that called primal kitchen.

And, you know, got his recipes, manufactured all of that and used his audience, you know, of a couple hundred thousand people on an email newsletter in this niche to like drive his first sales. And then as it went from there, he was trying to get distribution grocery stores. And I don't know the exact details, but I imagine what happened is things like, like getting in Whole Foods for the very first time. They're like, um, sure. We'll see if people buy this. We'll like give you one bit of placement in this one store in Austin. Right.

Well, what he does is you just go into your email tool. So like, okay, let's target everyone who lives within 50 miles of that store. And you're like, why don't you go buy this? You know, Hey, like great news. Primal kitchen products are now in this whole foods location. Go buy it in person. Right. And then the week later you talk to your whole foods rep and you're like, so, uh,

you know, how'd that little test do? You put it in like a couple of stores, how'd that go? And they're like, it went incredible. Like people had sold out instantly. Really? Oh, that's fascinating. I love that the product is resonating, you know? And it's like, well, no, you used your audience to kickstart that. So they can spread through it. They get more distribution, expand from there using the power of audience. The short version of the story is in two years, they sold Primal Kitchen to Kraft Foods for $150 million. My God.

And so when you think about, okay, if you have all of these people who are like close for big fans of a topic, you can direct that attention to affiliate products, courses, eBooks, that kind of thing. Or in the case of Mark says, and then he's like, no, I'm going to create a consumer product that a massive scale. And it's like, okay, a blog can be worth, you know, hundreds of millions of dollars.

And Emily Weiss created this blog called Into the Gloss about fashion, right? And so that was a topic that she cared about. And like, okay, a fashion blog, what could that be worth? Probably a decent amount. But it ended up being the thing that kickstarted her company Glossier. Oh, that's her company? Yeah. That's her company. That was in Common Garden, I saw it yesterday. Yeah, right? Yeah.

Can a blog build into something worth a billion dollars? Yes, if you think about things in the right way. And so you have to focus on products that have built a lot of value or can be sold to many, many people, often purchased in a recurring way. If we go to the celebrity world, like if you think Ryan Reynolds, he's someone who's like, I'd rather not get paid 500 grand or a million bucks for a TV commercial. I'd rather buy a company like Mint Mobile or Aviation Gin

And then use my marketing acumen and, you know, face to promote those and have all the equity value. And, you know, he sold aviation gin, I think for seven or 800 million, uh, mint mobile. He sold for 1.3 billion to T-Mobile. Right. And so he's not like, he's not doing basically a paid sponsorship to be on a TV commercial. He's like, Nope, I'm going to do it where I get captured the full equity value. And there's example after example, and people focus on them in the celebrity world.

But it's happening nonstop in the creator world in the same way. And that's a topic that I'm absolutely obsessed with. And I guess just to give one more example, that's what I'm doing with ConvertKit, right? I can take my podcast, my content, my network, all of that, and I could focus it on books and courses. And that's a great way to make $500,000 or a million dollars a year.

Or ultimately I can channel all of that into building ConvertKit as a software company that's now at $40 million a year in revenue and worth a few hundred million. And then my goal, that's the premise behind the Billion Dollar Creator, my goal is to build that into a company worth a billion dollars. And it's just the same thing. What's the best ROI place that can direct that attention? It's absolutely wild. Yeah.

The interview I did with Dan Priestley on this podcast came out a couple of days ago, so I was re-listening to that. He is sort of a serial entrepreneur here in the UK. And he's also very bullish on the... He was saying to me, Ali, look, you can screw around with courses all you like, but if you owned a business outside of your YouTube channel business and directed traffic to that, or even owned a minority equity stake in a business and directed traffic to that, and that business then exits,

In one transaction, you could make the same amount of money as you would make in a lifetime of selling courses. Correct. And I was like, oh, yeah, I know. I know that's right. But to me, that just seems like

you know if i if i look at someone like sahil it's he's he's got the background in private equity and like investment banking and all that and for him it probably seems easy to be like oh i guess i'll just build a business and hire an operator and stuff to me that's such a black box right where i'm like i don't know anyone who could do that but i as i'm saying that i mean like it wouldn't be that hard to find out because i literally spend a day just like going through people i know who follow me on twitter and be like hey i wanted to

I want to do this thing. I want to hop on a call, get some advice from the people that I know, put out a message to my newsletter and be like, hey, who wants to partner up in building one of these things? It would be very doable.

I don't know why I'm not doing it. It just feels scary, feels hard, feels like a black box. I don't really know. I'm very comfortable in the courses business. Well, there's a timing thing as well, right? It would be very easy for someone to listen to what we're doing here and maybe they have, say, 50,000 subscribers on YouTube, 100,000, right? Something that is a very meaningful milestone and a huge audience. Like I always, someone's like, oh, 100,000 isn't big. I'm like, look at like the largest football stadium. Like that's 100,000 people, you know? Yeah.

It'd be easy to look at that and go, okay, forget courses, forget all of these other things. I am going to go build the next primal kitchen. I'm going to go build the next mint mobile or whatever. And that would be jumping like three ladders, attempting to jump three ladders simultaneously in like a single leap. Yeah. And that is a pretty sure way to fail. Right. And so instead of what you're doing, you're iterating through all of these things, right? You have learned to build a team, right?

Five years ago, I don't think you knew how to build and manage a team, right? And so you got to do it in a little bit lower stakes environment. You didn't take all of your savings from the YouTube channel and say like, we're going to pour this into an app. And we spent a million dollars building out this app and it totally flopped because I didn't know how to build and manage a team, right? And so a part of the Ladders of Wealth Creation article is to think about the skills that you need in order to do this and deliberately chunk away at them, right? And so-

That's the thing. I think it'd be totally fine to say like, oh, I am not ready for this. I want to get ready for it. So maybe the like building Hey Friends as an agency is one of the, is a key building block for you in those skills because you're like, wait, this would be the first time that I have a business that's making substantial cashflow and requires very little time for me.

That's something for Paperboy and my agency with Sahil and then Shane, our CEO, that was really weird to me. So I showed up to a call about the next steps. We'd launched it. We'd done a bunch of things. And I showed up to an update call. We talked through it. We helped Shane with some key decisions he was trying to make. And then I left. And what was really weird to me is that I did not have a single to-do item coming out of that call. Whereas with ConvertKit, I am deeply embedded in all these things. And I realized, oh, I'm

I've like put myself in this too much and it's holding things back. So a key learning for me is like, wait, I can have a successful business that I don't spend meaningful time on. And I'm still kind of sitting with that because that was just like a month ago. And you're like, wait, so going to a journaling prompt, right? How could ConvertKit be more successful if I spent less time on it?

And you're like, it could, like my time is wildly valuable. All of us have a huge impact everywhere I go, whatever we want to say about ourselves. But then I think about it, I'm like, okay, well I could empower my team more. I could make the vision more clear. I could step out of the weeds, you know, like there's so many things in that. Um, and so I think these are just skills that we build and develop over time. And so I think in your case, it might be totally fine to say like, oh, I am not ready for this level. Hmm.

Because there's either skills that I want to continue to build or a certain level of comfort. And then make a roadmap. What would have to be true for you to feel ready at that point? What small steps could you make? Is there a business that you could come in and say, hey, I'd love to buy 10% of your business for $100,000. And then I will also actively promote it and get a rev share from it. There might be something that you could push on that level and you could try it out.

and then end up with this portfolio business. So like, how could you ease in rather than take a big leap? - That's a really good point. Yeah, at the moment I think I'm thinking of it as all or nothing, but actually just as you were saying that I was thinking, instead of thinking of Hey Friends as a, oh, I don't need to do anything. That's a great learning opportunity. I could just actually take more of an interest in like, oh, okay, I wonder how this is actually working. Like what's going on here? Treat that as a bit of a learning thing.

Yeah. It's like talking to Hunter, who's the CEO of like that whole company. Like how does he build teams? How would he, you know, what, what traits are you seeing? If you were to look for another operator for an entirely different business, what could you learn from watching him? All of those things are really, really interesting. How do flywheels fit into this whole thing? Flywheels are probably like my biggest obsession right now. Yeah.

So do you think your audience knows what a flywheel is? Should we explain it? Let's define it. Yeah. Let's define it. Yeah. So I first encountered a flywheel in 2008. I was in Lesotho, which is a little country. Oh, no way. That's where I used to live. Really? Yeah. I lived there for like six years growing up. Okay. Where? In Masaru. Okay. So I was in Masaru. No way. That is very, very random. Yeah.

Most people were like, what? Where is that? And they're like, oh, that's that country inside South Africa. So we have family friends who lived around South Africa and listened to. And so we got to do a trip with them and go visit and did some work at this orphanage. And we put in, it like had a well drilled and then we were installing, you know, we need some kind of pump on top of it.

At the time in 2008, the like electricity wasn't super consistent. And so they didn't want to put an electric pump in there. They wanted a hand operated pump, which if you think about from a, you know, like at least near where I live, you'd go to a campground. There'd be like this hand pump that, you know, is a pretty works fine for camping for the weekend. You would not want like a hundred kids be relying on that for water. So instead we install a flywheel, which is this big metal wheel that sits on top.

And instead of having this like up and down linear action that a pump has, it has a rotating action. And so it moves, it turns continuously. And so once we got it all set up, um, like it was really hard to move at first. Like my friend Luke and I both like we're on each side of it on the handles, like turning it. It's very difficult to get going. And then what we did, like over time it starts to speed up and gain momentum and it gets easier.

And what that allowed us to do is like, then he steps away and he's no longer turning it. And I can turn it by myself and then I can turn it with one hand. And then, you know, by the end, I keep the momentum going with one finger because this continuous thing in the metal wheel, like the inertia of that carries forward. And so when you think about it from a business perspective, most things that we do are the hand pump version. There's a direct correlation to how much effort we put in and how much results that we get out, right? Every pump down, there's a spurt of water.

And flywheels are fascinating because they almost sound too good to be true. Like I've defined it as three laws for a flywheel. The first thing is that every action flows smoothly into the next, right? It's this, it finishes in a loop. The second is that it should get easier with every rotation.

right every time you turn it it gets easier and the third thing is every time every rotation it actually produces more and in an abstract business sense you're like this is too good to be true you're saying this gets easier with time and produces more that's insane but it actually works in real life physics right and i i know firsthand of how hard that was to turn at first and how little water i got and then by the end i'm just standing there spinning it one hand it's so easy

So I'm now absolutely obsessed with, uh, with flywheels of how can I apply this all throughout my business and how can I help creators apply this? So I want to go both on a very small scale and then on a very large scale. Let's take, for example, writing a newsletter every week. On one hand, it's not that hard. On the other hand, you're like, shoot, what do I even write about? And if you're working through a list of ideas or, or it's scattered, then you're like,

you're trying to figure it's Monday night. The newsletter goes out Tuesday morning. You're like, what should I even write about? I'm running out of ideas. If you have a flywheel around content ideas, then it can completely change the game. So let's say that if we map out this flywheel, new people are signing up for my newsletter. Yep.

And I send them a few welcome emails. And like in the third or fourth welcome email, I ask them a question and I say, hey, what is your biggest frustration with learning to scale your YouTube channel? Right, that's what we're teaching on this newsletter. Then hit reply and let me know. People hit reply and they say, oh, I'm really struggling with how to make thumbnails. I'm really struggling with like building up my content calendar, you know, whatever it is.

All of those replies you put into a label in Gmail or use Zapier to put into something else. And now when you're saying, okay, what should I write about this week? You just go into those replies and say, oh, John is struggling with thumbnails. Let me write an answer to his question and then make it a little more generic so it fits for everybody and not send it out to the newsletter.

And so the way this works in a flywheel is people come in. So basically the more people who come in, the more frustrations I collect, which gives me more ideas for content, which as I publish that content reaches more subscribers, which gives me more frustrations, which gives me more ideas, content on and on. So this is a continuous loop. It gets easier with time because we're getting more and more of these questions. And then it also produces more.

Because then later, each piece of content is going to reach even more people. So early content might have gotten five newsletter subscribers, and down the road, the content might get 500 new newsletter subscribers. So that's an idea of taking something core in your process and turning it into a flywheel that's now just running for you with some really basic automation. If you think about, on the other end, we talked about Sahil. He is really interesting to me because he's grown a newsletter platform

to 500,000 subscribers in three years, two and a half years, like very, very quickly. And actually I think he's only just over a year from a hundred thousand to 500,000. And it's all because of this flywheel that he's built out. And so the way that this flywheel works is he has new subscribers coming in from social. So, you know, Twitter, Instagram, and LinkedIn primarily as they come in, he is, um,

selling sponsorships in his newsletter. So actually ConvertKit has a whole advertising division. So we sell the sponsorships in his newsletter. He's got emails, like automated emails, welcoming people to his newsletter, sharing his work, all of that kind of thing. And then he's taking the money that he makes from his sponsorship and spending it on paid acquisition through another company that we bought called Sparkloop, which has this recommendations network.

And then that gets his, it grows his newsletter. So in the simplest form, the more subscribers he has, the more money he makes on sponsorships, which means he invests more money in paid growth to make his newsletter bigger, which means he's making more money on sponsorships, which means he has more money to invest and so on. And it's, it's pretty basic, but like an early rotation of this flywheel would get him, uh, maybe $10,000 in sponsorships for the month. And, um,

And then he reinvested that 10,000. And that might get him 5,000 new subscribers. But now he's making 50,000 to 70,000 a month in sponsorships. Bloody hell. And reinvesting that and growing even faster. So you just watch the snowball rolling down the hill getting bigger and bigger and bigger. Yeah.

And it's getting easier with time. It's producing more and more results. And he's well on track to hit a million subscribers in the next five, six months, which is crazy to think. He's now adding like 100,000 email subscribers a month. And it's all because he's got this aspect of his flywheel absolutely dialed in. And there's things with it of other creators he partners with and more and more that goes into it.

But basically trying to take all these one-off tasks that you do and turn them into a process that can either run automatically or, you know, be operated by your team or something that you can run in a pretty straightforward way. So I'm obsessed with flywheels. That's the point. That's good stuff. You're like, I see the diagrams, writing, newsletter, it's all. Yeah.

Yeah, I'm just thinking like everything is fundamentally downstream of writing. And all commercial activities are fundamentally downstream of the newsletter, I think. Yeah, and one thing that I've done is I love the design tool Figma. And so it has this infinite canvas.

And so I like to map out my flywheels in that. I'm like, okay, what about this? And I'll, I'll design the same thing in a bunch of different ways. And cause I like playing with hypotheticals of, um, like figuring out what's the one driver of this flywheel. What's the thing that makes the biggest impact. And then what if I had this other thing that was the biggest driver. And so you can really just play with like sketching this out. Or I have all these components that I use in Figma to like move it around and, and,

Just think about how could I tweak this flywheel? And it forces you to really simplify things about your business that otherwise you just wouldn't. So anyway, like the sketch that you started to make there, that's exactly the kind of thing that I'll make like dozens and dozens of flywheel sketches. Oh man, I've got to show you my FigJam. I do the same thing. Like on a Sunday, I'll go to a coffee shop for four hours and just literally draw boxes on FigJam. Yeah, just be like, how do I simplify our business to only three metrics? What are the three that are really, and this is like...

Yeah. And then it'll be really simple. It'll be like, okay, well, views equals newsletter subs equals revenue. I'm like, why was that complicated? Yeah.

Yeah, and so then you have to close that loop. If you want to make it a flywheel, is to go, how does more revenue drive more views? More revenue drives more profit. Profit gets reinvested into business. Right, and then you get specific, right? Okay, that profit, how exactly does it get reinvested? Okay, yeah, that's what I haven't done yet because I've just been like, oh, generally. But how it would do is if we can increase our output, that's one option. But a completely other option I've not even considered is the Sahil paid acquisition model. Yep. Where actually putting money in gets you more revenue.

more views and stuff putting ad spend behind our videos that we know will convert to things like yeah and and like in a very simple way if you looked at like mr beast spywheel he's just like great how much money did i make how much can i pour this into making a ridiculous video that's going to get more attention right and and that that uh compounded pretty quickly

And so then what I like to do is get to the point in the flywheel where it's obvious, like first figure out how to close the loop. Cause most people get to a linear process. Yeah. Right. So closing the loop is really, really important. And then force yourself to come up with four or five different ways to close the loop. Right. Um,

I had a very brief stint going to college and I was in art school and I didn't have a lot of good takeaways. But one thing that they would force you to do is when you're planning out your art in the early stages, do something called thumbnail. And they just said, take a piece of paper, like fold it up a bunch and then unfold it. So you have like, you know, 12 boxes or something of, of a small size and like sketch out,

a particular composition for your landscape, or I use it a ton in designing apps later on. I'm like, at the small size, what are 10 different ways that I could design this app interface? And so I'd apply the same concept to flywheels, where I'd say, okay, what if I...

What if money and reinvesting profits, what if I'm not allowed to use that as the loop closer or the engine of this flywheel? What else could I use? And that'll get me thinking through, like, okay, maybe it's relationships. Maybe the going on podcasts or something else, like partner webinars, maybe that turns into the thing. And so I like to put in these things, and the classics would be

What if I'm not allowed to reinvest any money in my business? What if I have to reinvest every dollar that I make in my business? What if you play with those constraints and you get to things that, you know, you might get all the way back to the exact same thing that you drew out in the first place, but you'll be way more confident in it. Or you might get to something entirely different.

Sick. All right. That's some homework for me. So A, I'm committing, officially committing to doing a thousand words a day. So I'll message you and let you know how that goes. That'll be so good. If you're like, I'm thinking a thousand words a day, that's email newsletter. It's like, I never struggle with like, you know, it's Sunday today. So I need to send my newsletter today and I don't have anything written. Right. We need to write something today. So that'll be a good start. But also things like Instagram captions and stuff. I always feel like I have thoughts, but like,

I can't share those thoughts because they're either in the newsletter or they're compiled into like a sort of full on YouTube video production type thing. But actually, if I just had the stuff written, I just have things I'd like to share and just chucking them as an Instagram caption or as a Twitter long form post or something. And then alongside also making progress on these like four different book ideas. And all of it would just happen by default if I actually wrote a thousand words a day. Mental. Yep. Mental. Simple, not easy. Simple, not easy. All right. We got this.

Nathan, thank you so much. For anyone who's listened to the last two and a half hours of this conversation, who vibe with your way of seeing the world, any final parting words of advice for anyone who's gotten this far in the pod? Oh, man, I think create every day is probably the biggest thing. Like if you embody that, and you keep learning continually, make something, put it out in the world, and try to learn from how it's, you know, everything that happened there.

that's the single biggest thing and then everything else is is strategy downstream from from those habits so don't over complicate it like we can figure out all of the crazy advanced flywheels on how exactly we're making the highest roi from a single unit of attention yeah later on but you got to make sure that you have the creation dialed in brilliant uh where can people learn more about you and your work if they would like to find out more yeah let's see uh

If you go to NathanBerry.com, that's all of my essays and all of that. I'm starting a new podcast called Billion Dollar Creator. So get to nerd out on all things like flywheels and equity and everything else.

And then, you know, he's not using ConvertKit yet. It's just at ConvertKit.com. We power all the biggest newsletters on the internet. Yeah, including ours, which is not very big, but well, actually, it's reasonable. It's reasonable, about 500,000 subs in total. That is a very large newsletter. Nice, I'm glad to hear it. And I realized that like, you're actually most famous for ConvertKit and we spent basically zero time talking about ConvertKit. So it'd be great to do a round two at some point and going charting the 10 year history of ConvertKit and the lessons you've learned along the way. That would be awesome for round two.

But yeah, thank you so much for joining. Yeah, thanks for having me.

All right, so that's it for this week's episode of Deep Dive. Thank you so much for watching or listening. All the links and resources that we mentioned in the podcast are gonna be linked down in the video description or in the show notes, depending on where you're watching or listening to this. If you're listening to this on a podcast platform, then do please leave us a review on the iTunes store. It really helps other people discover the podcast. Or if you're watching this in full HD or 4K on YouTube, then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode. That would be awesome. And if you enjoyed this episode, you might like to check out this episode here as well, which links in with some of the stuff that we talked about in the episode.

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