What does it really take to build a multi million dollar software company from the ground up. On the show today, I am taking you behind the scenes with Nathan Barry, the founder and CEO of the wildly successful email marketing platform convert Kit. When convert Kit was just eighteen months old and failing miserably, Nathan was actually told to shut it all down. But instead of quitting, Nathan took a counterintuitive approach that allowed him to turn the struggling startup into a business that now serves over fifty thousand creators worldwide and is valued at over two hundred million dollars. I have been a fan and a follower of Nathan's four ages, and in this chat we cover all sorts of tactics that Nathan uses in his work, from his annual life review ritual through to how writing one thousand words a day for six hundred consecutive days transformed his work completely. My name is doctor Amantha Imbert. I'm an organizational psychologist and founder of behavior change consultancy Inventium, and this is how I work The show about how to help you get so much more out of the hours in your day. Nathan Barry was of the most fascinating person to research as I was preparing for this interview, and one of the most interesting rituals I came across of Nathan's was his annual life review. So while many companies do an annual review of their business and publish it, Nathan actually does one of his life. So I was keen to hear more about what this process looks like.

What does it really take to build a multi million dollar software company from the ground up. On the show today, I am taking you behind the scenes with Nathan Barry, the founder and CEO of the wildly successful email marketing platform convert Kit. When convert Kit was just eighteen months old and failing miserably, Nathan was actually told to shut it all down. But instead of quitting, Nathan took a counterintuitive approach that allowed him to turn the struggling startup into a business that now serves over fifty thousand creators worldwide and is valued at over two hundred million dollars. I have been a fan and a follower of Nathan's four ages, and in this chat we cover all sorts of tactics that Nathan uses in his work, from his annual life review ritual through to how writing one thousand words a day for six hundred consecutive days transformed his work completely. My name is doctor Amantha Imbert. I'm an organizational psychologist and founder of behavior change consultancy Inventium, and this is how I work The show about how to help you get so much more out of the hours in your day. Nathan Barry was of the most fascinating person to research as I was preparing for this interview, and one of the most interesting rituals I came across of Nathan's was his annual life review. So while many companies do an annual review of their business and publish it, Nathan actually does one of his life. So I was keen to hear more about what this process looks like.

I learned this from a creator named Chris Gillibo back in twenty eleven. The first thing is I write them for myself, and that's important because if you're trying to think about writing it for someone else, you know, then you get into like is this bragging? So customer number one is me, and probably customers one through ten are me. Somewhere in there are my kids as a customer. That would just be really interesting. There's all these different businesses like story Worth than others that are here's a bunch of questions to ask your parents so that you can capture their life and story end video, and we'll make this amazing artifact out of it. And I think that would just be the best. I need to deal it with my parents, and I haven't yet. I thought like, why don't I just do that gradually along the way. So the main customer is me, The next customer would be my kids thirty years from now. Why not if I'm going to do the work, why not put it out there for the world and let people follow along. So that's the high level idea.

I learned this from a creator named Chris Gillibo back in twenty eleven. The first thing is I write them for myself, and that's important because if you're trying to think about writing it for someone else, you know, then you get into like is this bragging? So customer number one is me, and probably customers one through ten are me. Somewhere in there are my kids as a customer. That would just be really interesting. There's all these different businesses like story Worth than others that are here's a bunch of questions to ask your parents so that you can capture their life and story end video, and we'll make this amazing artifact out of it. And I think that would just be the best. I need to deal it with my parents, and I haven't yet. I thought like, why don't I just do that gradually along the way. So the main customer is me, The next customer would be my kids thirty years from now. Why not if I'm going to do the work, why not put it out there for the world and let people follow along. So that's the high level idea.

Can you talk me through the different themes or categories when you're sitting down to do your annual life review that you look at.

Can you talk me through the different themes or categories when you're sitting down to do your annual life review that you look at.

The first thing is that I always try to put a title on it of some kind, which usually comes to me at the end. So I have, like twenty twenty two, a year of growth and managing stress right, really trying to navigate. But I walked through the businesses convertates the main one. But then I'll talk through the other businesses and opportunities that I have. I own ten percent of a California ghost town. I have Airbnbs, I own a local newsletter called from Boise. So I like to provide updates on some of those things that I usually don't talk about. It's just a fun checking point. If you go back to the early ones, so like twenty twelve to maybe twenty fifteen, there was much more of a split of like here's the books that made money that was selling and things across the audience, and then that just eventually all merged to like it's ninety nine percent convertate, So that dominates a good part of it. Another category, travel is a big one. I just like to reflect back even on how many trips that I took. Another big category is our farm. We moved to this property seven years ago and then expanded it three or four years ago. It's such a big project and we don't make nearly as much progress on it as we want. That it's really helpful to then be able to look back and see, like, oh, that was the year that we put in the playground for the kids. So that's a big category. And then I always set goals and I usually hit less than half of them, but it still helps me to set the goals, and I'll check in on fitness goals as well. It's written for me, but i'd let people read along.

The first thing is that I always try to put a title on it of some kind, which usually comes to me at the end. So I have, like twenty twenty two, a year of growth and managing stress right, really trying to navigate. But I walked through the businesses convertates the main one. But then I'll talk through the other businesses and opportunities that I have. I own ten percent of a California ghost town. I have Airbnbs, I own a local newsletter called from Boise. So I like to provide updates on some of those things that I usually don't talk about. It's just a fun checking point. If you go back to the early ones, so like twenty twelve to maybe twenty fifteen, there was much more of a split of like here's the books that made money that was selling and things across the audience, and then that just eventually all merged to like it's ninety nine percent convertate, So that dominates a good part of it. Another category, travel is a big one. I just like to reflect back even on how many trips that I took. Another big category is our farm. We moved to this property seven years ago and then expanded it three or four years ago. It's such a big project and we don't make nearly as much progress on it as we want. That it's really helpful to then be able to look back and see, like, oh, that was the year that we put in the playground for the kids. So that's a big category. And then I always set goals and I usually hit less than half of them, but it still helps me to set the goals, and I'll check in on fitness goals as well. It's written for me, but i'd let people read along.

So, Nathan, if you were going to coach me in starting to do this process for myself, what advice would you give me?

So, Nathan, if you were going to coach me in starting to do this process for myself, what advice would you give me?

Years one through three aren't that interesting? What's interesting about it is when you do it for maybe years four through ten. And so the first thing I would say, what's a process that you could make sure to do consistently every year for the rest of your life, because then it's really interesting. What does help me. It's putting a lot of things on my calendar because that's how I remember. There's all kinds of things where I'm like, oh yeah, I forgot about that. So photos and calendar would be the biggest things. Take plenty of photos in a way that you can review them and pull out the highlights, because those two things are basically what reminded me of the details in the year. If you have health or fitness goals, make sure you're always tracked in the same app. Don't chase the new tools, because what you want is to be able to say like, oh, as I've been on this fitness journey, let me just screenshot the data of the last five years, instead of saying like, oh yeah, I used my Fitness Pal and I was over here with the bit and I jumped to you know, all of these different.

Years one through three aren't that interesting? What's interesting about it is when you do it for maybe years four through ten. And so the first thing I would say, what's a process that you could make sure to do consistently every year for the rest of your life, because then it's really interesting. What does help me. It's putting a lot of things on my calendar because that's how I remember. There's all kinds of things where I'm like, oh yeah, I forgot about that. So photos and calendar would be the biggest things. Take plenty of photos in a way that you can review them and pull out the highlights, because those two things are basically what reminded me of the details in the year. If you have health or fitness goals, make sure you're always tracked in the same app. Don't chase the new tools, because what you want is to be able to say like, oh, as I've been on this fitness journey, let me just screenshot the data of the last five years, instead of saying like, oh yeah, I used my Fitness Pal and I was over here with the bit and I jumped to you know, all of these different.

Things in I think it would have been twenty twenty three. Set the goal to be a lot less stressed. I'm curious when you set a goal like that, how on earth do you plan to achieve that.

Things in I think it would have been twenty twenty three. Set the goal to be a lot less stressed. I'm curious when you set a goal like that, how on earth do you plan to achieve that.

Yeah, I mean, that's a hard one, but I think it's more of a guideline than a goal, or it's an intention. My wife is two younger brothers, and she and I were dating and got married when they were probably fourteen and sixteen, and so I was always entertained by the way they did things, the stories they told and all of that. And they told me once that when you're faced with two options in life, choose the one that will result in a better story. Where's the chance to be a better story? And so I think of being less stressed, or say an intention to be less stressed, as something like that. It's not like that's the guiding principle that defines the whole year, but it's like, when you're met with two options in life, well, what's the method to solve that that's going to result in less stressed. I've had these book ideas that I've wanted to write for years, and I've chipped away at and one of them that I felt like I should write first, which is a book about building an audience. I've worked off and on for five years and it just has not come together. The book has not clicked, and the be less stressed. Version of that was to hire a friend of mine who I think is one of the best in the world at book packaging, positioning, marketing, all of that, and just say I'm still going to write the book, but come alongside me and help me figure out what this book is. And instead of me grinding away in my own beating my head against the wall for more years trying to do it, I did like six three hour calls with him, so there's a lot of time, but we really work through exactly what the book should be. And we didn't write a We wrote like a five thousand word outline of this book working through it, and he knows my work really well. It's Tim Grawl if anyone wants to follow along storygrid dot com. But he's one of those people that's remarkable at it. If you look at the top one hundred pop songs, you look at like the producers of the writers, and you see this one person is behind like twenty five of them. They understand what it takes to make a great song. Tim understands what it takes to make a great book. I have this goal to finally write and finish this book this year. What's the less stress version of it. Oh, let me bring a professional alongside me to really help and guide me through this process. Same goal, different result.

Yeah, I mean, that's a hard one, but I think it's more of a guideline than a goal, or it's an intention. My wife is two younger brothers, and she and I were dating and got married when they were probably fourteen and sixteen, and so I was always entertained by the way they did things, the stories they told and all of that. And they told me once that when you're faced with two options in life, choose the one that will result in a better story. Where's the chance to be a better story? And so I think of being less stressed, or say an intention to be less stressed, as something like that. It's not like that's the guiding principle that defines the whole year, but it's like, when you're met with two options in life, well, what's the method to solve that that's going to result in less stressed. I've had these book ideas that I've wanted to write for years, and I've chipped away at and one of them that I felt like I should write first, which is a book about building an audience. I've worked off and on for five years and it just has not come together. The book has not clicked, and the be less stressed. Version of that was to hire a friend of mine who I think is one of the best in the world at book packaging, positioning, marketing, all of that, and just say I'm still going to write the book, but come alongside me and help me figure out what this book is. And instead of me grinding away in my own beating my head against the wall for more years trying to do it, I did like six three hour calls with him, so there's a lot of time, but we really work through exactly what the book should be. And we didn't write a We wrote like a five thousand word outline of this book working through it, and he knows my work really well. It's Tim Grawl if anyone wants to follow along storygrid dot com. But he's one of those people that's remarkable at it. If you look at the top one hundred pop songs, you look at like the producers of the writers, and you see this one person is behind like twenty five of them. They understand what it takes to make a great song. Tim understands what it takes to make a great book. I have this goal to finally write and finish this book this year. What's the less stress version of it. Oh, let me bring a professional alongside me to really help and guide me through this process. Same goal, different result.

Yeah, it reminds me of that Tim Ferriss question, what would this look like if it were easy?

Yeah, it reminds me of that Tim Ferriss question, what would this look like if it were easy?

It's a great one. Now.

It's a great one. Now.

I like that as an approach to lowering stress. And really it comes down to the decisions that you make. It's a segue into a big decision that you made two years in to convert Kit. So one of the videos that I watched in preparation for this interview, you telling the story of what happened a couple of years into creating convert Kit and your mental health reached what sounded like an all time low. It was an incredibly moving video, and thank you for sharing that. How did you make that decision to essentially continue on with convert kit and not kill it at that point in time.

I like that as an approach to lowering stress. And really it comes down to the decisions that you make. It's a segue into a big decision that you made two years in to convert Kit. So one of the videos that I watched in preparation for this interview, you telling the story of what happened a couple of years into creating convert Kit and your mental health reached what sounded like an all time low. It was an incredibly moving video, and thank you for sharing that. How did you make that decision to essentially continue on with convert kit and not kill it at that point in time.

We have this idea that projects, you're going to start them and they might take longer than you think, but progress will always be linear and then eventually exponential and it will just keep moving. Worst case, things will be flat. We don't really think about what Seth Godin will talk about as the depth of when things decrease you know, and you hit this both emotional low, but then also probably the business low. I was eighteen months into work on convercut when a friend of mine named heat and Shaw told me, Nathan, I think you should shut down convercate and I remember thinking like, that's not a nice thing to say to someone. So it was like surprised, maybe a little offended. Especially if you live in a world where people just say nice things, then that's a little bit shocking. I hope that you, as a practice try to find a friend group that doesn't just say nice things like that's the biggest gift. But going from there, what he said is you should check in counbirk it And I was like, okay, why. He's like, look, you've been successful selling books and courses. You'll be successful plenty of other things you do. Could birk it is eighteen months in, it's shrinking at this time, like you should shut it down and move on to something else. He'd let me sit with that for a second and then he goes, or you could take it seriously and give it the time, money and attention it deserves and build it into something real. And that's ot with me for a while. I wish I'd done the thing of like immediately made a decision, But often when we hear good advice, we've sit on it for too long. And so it ended up being about six months later. So two years in that revenue had declined. We're at thirteen hundred a month in revenue. It was no longer longer covering like even the server hosting basic expenses. I'm losing money to operate this business. And I was trying to think, how am I to make this decision? In my case, I still really wanted to build a software company. I definitely absolutely want this. So then the next question I asked is have you given this every possible chance to succeed? Because if you've truly given it your best and it hasn't worked, then you can let it go. You can lay it to rest, knowing that everything within your power was done. In my case, I hadn't, right I asked that question, and I was like, no, I have worked on it part time. I haven't put that much money into it, Like I have more savings that I could pour into this. And I realized that if I shut convert it down in that moment, I would be that person at a party three years from now and you'd be like, oh, what happened to convert it? And like, yeah, you know, I had to shut it down. But I think if I had stuck with it, like I for sure could have made that happen. You know, like we've all encountered that person who is like, oh, just this had been different, you know, it would have been a huge win. And I don't like that person. I don't want to be that person. And so I felt this disconnect between what I said I wanted and with the effort and work I was willing to put in. And so I actually set a goal within six months to get to ten thousand a month in revenue or I would shut it down. It was really that framework helped me decide. And then obviously nine years later after that moment, I'm pretty happy with the double down decision because now it's a giant company that powers fifty thousand plus creators like entire business.

We have this idea that projects, you're going to start them and they might take longer than you think, but progress will always be linear and then eventually exponential and it will just keep moving. Worst case, things will be flat. We don't really think about what Seth Godin will talk about as the depth of when things decrease you know, and you hit this both emotional low, but then also probably the business low. I was eighteen months into work on convercut when a friend of mine named heat and Shaw told me, Nathan, I think you should shut down convercate and I remember thinking like, that's not a nice thing to say to someone. So it was like surprised, maybe a little offended. Especially if you live in a world where people just say nice things, then that's a little bit shocking. I hope that you, as a practice try to find a friend group that doesn't just say nice things like that's the biggest gift. But going from there, what he said is you should check in counbirk it And I was like, okay, why. He's like, look, you've been successful selling books and courses. You'll be successful plenty of other things you do. Could birk it is eighteen months in, it's shrinking at this time, like you should shut it down and move on to something else. He'd let me sit with that for a second and then he goes, or you could take it seriously and give it the time, money and attention it deserves and build it into something real. And that's ot with me for a while. I wish I'd done the thing of like immediately made a decision, But often when we hear good advice, we've sit on it for too long. And so it ended up being about six months later. So two years in that revenue had declined. We're at thirteen hundred a month in revenue. It was no longer longer covering like even the server hosting basic expenses. I'm losing money to operate this business. And I was trying to think, how am I to make this decision? In my case, I still really wanted to build a software company. I definitely absolutely want this. So then the next question I asked is have you given this every possible chance to succeed? Because if you've truly given it your best and it hasn't worked, then you can let it go. You can lay it to rest, knowing that everything within your power was done. In my case, I hadn't, right I asked that question, and I was like, no, I have worked on it part time. I haven't put that much money into it, Like I have more savings that I could pour into this. And I realized that if I shut convert it down in that moment, I would be that person at a party three years from now and you'd be like, oh, what happened to convert it? And like, yeah, you know, I had to shut it down. But I think if I had stuck with it, like I for sure could have made that happen. You know, like we've all encountered that person who is like, oh, just this had been different, you know, it would have been a huge win. And I don't like that person. I don't want to be that person. And so I felt this disconnect between what I said I wanted and with the effort and work I was willing to put in. And so I actually set a goal within six months to get to ten thousand a month in revenue or I would shut it down. It was really that framework helped me decide. And then obviously nine years later after that moment, I'm pretty happy with the double down decision because now it's a giant company that powers fifty thousand plus creators like entire business.

That's an amazing story. Something I have heard you say when I've listened to other interviews with you is talking about certain things being simple but not easy, and that really stuck with me. Can you tell me a little bit more about what that means?

That's an amazing story. Something I have heard you say when I've listened to other interviews with you is talking about certain things being simple but not easy, and that really stuck with me. Can you tell me a little bit more about what that means?

There's so many things in life that we want to know what's the secret. I was talking to this person that I met, and somehow it came up in conversations that they'd lost like fifty pounds and they looked quite fit, and I was trying to imagine them with fifty more pounds, and I was just like, how did you do it? Like expecting they'd you know, uncovered this whole secret. And there's like I gradually increased my movement over time, and I just made sure that I operated a caloriye, and that's it. Then, So you take something like weight loss, it's pretty well known. It is relatively simple and definitely not easy. Right, So we want to look at all of these things, whether it's building an audience for example, pretty much if you show up consistently and you were to choose one platform and say, okay, I'm going to build an audience on X, it's fairly simple. Post every day, network with other creators, and reply to comments and engage. Right, if you do that every single day for two years, like you're a student of the game, then I guarantee you're going to see success. It's fairly simple. And when I say it's simple, but not easy. What I'm referring to is stop looking for the hacks or the secrets or the tricks. You just have to make the hard decisions, easy decisions, hard life, hard decisions, easy life.

There's so many things in life that we want to know what's the secret. I was talking to this person that I met, and somehow it came up in conversations that they'd lost like fifty pounds and they looked quite fit, and I was trying to imagine them with fifty more pounds, and I was just like, how did you do it? Like expecting they'd you know, uncovered this whole secret. And there's like I gradually increased my movement over time, and I just made sure that I operated a caloriye, and that's it. Then, So you take something like weight loss, it's pretty well known. It is relatively simple and definitely not easy. Right, So we want to look at all of these things, whether it's building an audience for example, pretty much if you show up consistently and you were to choose one platform and say, okay, I'm going to build an audience on X, it's fairly simple. Post every day, network with other creators, and reply to comments and engage. Right, if you do that every single day for two years, like you're a student of the game, then I guarantee you're going to see success. It's fairly simple. And when I say it's simple, but not easy. What I'm referring to is stop looking for the hacks or the secrets or the tricks. You just have to make the hard decisions, easy decisions, hard life, hard decisions, easy life.

Now, you're one of the only entrepreneurs or CEOs that I've interviewed that has a writing habit, and for the most part, that's a daily writing habit. I'm curious as to what that currently looks like in your life.

Now, you're one of the only entrepreneurs or CEOs that I've interviewed that has a writing habit, and for the most part, that's a daily writing habit. I'm curious as to what that currently looks like in your life.

It's very scattered at the moment, and I actually have a bit of an identity crisis when it comes to my writing habit, and that's because I built a lot of my identity as a creator around this idea of writing a thousand words a day. I built this habit of writing a thousand words a day every day for six hundred days in a row, and I built my entire career as a content creator off of that thing. I wrote three books, odds of log posts, built an audience to ten thousand subscribers or more. Now, I ended up getting stressed out because of other things, getting shingles, and so at this point my writing habit is fairly sporadic. I still write fairly regularly, probably three times a week, but it's not the every single day habit that I wish it was, because I decided for this season I have a different priority.

It's very scattered at the moment, and I actually have a bit of an identity crisis when it comes to my writing habit, and that's because I built a lot of my identity as a creator around this idea of writing a thousand words a day. I built this habit of writing a thousand words a day every day for six hundred days in a row, and I built my entire career as a content creator off of that thing. I wrote three books, odds of log posts, built an audience to ten thousand subscribers or more. Now, I ended up getting stressed out because of other things, getting shingles, and so at this point my writing habit is fairly sporadic. I still write fairly regularly, probably three times a week, but it's not the every single day habit that I wish it was, because I decided for this season I have a different priority.

So what role, then, does writing now play in your life?

So what role, then, does writing now play in your life?

Writing is the way I bring most of my ideas to the world, and I still have so many things that I want to say. I have these flagship essays that I've written on building wealth and flywheels and these other concepts that I think are really really important, and I have a bunch more of those that I want to bring to the world, but the process of writing them is more time consuming. I think what I've decided is that I need to sequence the activities that I'm doing. I do way too many things and I spread myself then and now. What I'm doing differently this time is I'm diving into team building. So I might not write all of my own material. I might have an idea give it to a researcher who I haven't hired yet but still into hire. So I still plan to spend a good amount of time writing myself, but I think about content creation at the scale that I'm at very much as a team sport rather than a solo writer. In the cabin in the woods type of thing.

Writing is the way I bring most of my ideas to the world, and I still have so many things that I want to say. I have these flagship essays that I've written on building wealth and flywheels and these other concepts that I think are really really important, and I have a bunch more of those that I want to bring to the world, but the process of writing them is more time consuming. I think what I've decided is that I need to sequence the activities that I'm doing. I do way too many things and I spread myself then and now. What I'm doing differently this time is I'm diving into team building. So I might not write all of my own material. I might have an idea give it to a researcher who I haven't hired yet but still into hire. So I still plan to spend a good amount of time writing myself, but I think about content creation at the scale that I'm at very much as a team sport rather than a solo writer. In the cabin in the woods type of thing.

I find that fascinating As a writer myself. I've just had my fourth book come out, and I feel like the large part of my self identity is attached to being a writer and creating the thing myself and doing the research myself. How did you make that leap to almost detach part of your self identity from that writing process and a low yourself to delegate, outsource, build a team around it.

I find that fascinating As a writer myself. I've just had my fourth book come out, and I feel like the large part of my self identity is attached to being a writer and creating the thing myself and doing the research myself. How did you make that leap to almost detach part of your self identity from that writing process and a low yourself to delegate, outsource, build a team around it.

It's been a very gradual process. I'm not at the point where I would hire someone else to write a book for me. I have nothing against that, actually, because I think that you get in situations where you have someone who has an amazing story or point of view on the world and is not an amazing writer, and they should absolutely bring someone along. One thing that's been helpful for me is realizing that there's only so many hours in the day and so much time that you have to apply. I'm willing to get a team, so stop depriving the world and your ideas and actually build the systems and bring the team in place to make it happen.

It's been a very gradual process. I'm not at the point where I would hire someone else to write a book for me. I have nothing against that, actually, because I think that you get in situations where you have someone who has an amazing story or point of view on the world and is not an amazing writer, and they should absolutely bring someone along. One thing that's been helpful for me is realizing that there's only so many hours in the day and so much time that you have to apply. I'm willing to get a team, so stop depriving the world and your ideas and actually build the systems and bring the team in place to make it happen.

Now. Something that I know you're very passionate about is flywheels. Can you for people that have not come across what on Earth we are talking about, describe what one is.

Now. Something that I know you're very passionate about is flywheels. Can you for people that have not come across what on Earth we are talking about, describe what one is.

Yeah, So a flywheel is a concept in physics really of taking manual effort and then transferring it into something that like either storing the energy or carrying it forward. So the first time that I encountered a fly wheel was in two thousand and eight and I was in Lisutu, which is the landlocked country inside of South Africa, and we were working at an orphanage and we had drilled a well and we were going to put a pump on top of the well. And Masera, the capital city where we were at, had electricity, but in the two weeks we were there, I think it went out like eight times. So we didn't really want to put an electric pump on this well, and so I was thinking like, okay, we're adding a hand pump, and Jason, one of the guys leading our trip, was like, no, no, no, we're gonna put a flywheel on it. So instead of the hand pump, which would be this long handle, you go and pump your water and this the handle gives you leverage. But there's a direct tie between the effort that you put in and the impact or the results that you get back and at the moment you stop pumping, you immediately stopped getting water. And so instead of that, the flywheel is this large metal wheel that sits up on top of the pump. It's hard to get going initially, but instead of this linear up and down movement, it carries that momentum forward and it builds momentum over time. It's soon need an input, but I could basically with one or two fingers just keep this thing spinning. And so that's a metaphor. Obviously, like we get to apply it to all these other areas of life and business, and like we talked about health and business, that's a flywheel. It is incredibly difficult to get going. If you're starting with really small changes. You're just saying, oh, I'm gonna eat a piece of fruit every day. You can build on from there. So it really came to three laws that define a flywheel, especially in the business case. The first is every step in a flywheel should flow smoothly from one into the next. The second law is that it should get easier with each rotation, and then the third laws it should deliver more with every rotation. So that's flywheels at a high level, but and we can go wherever you'd like from there.

Yeah, So a flywheel is a concept in physics really of taking manual effort and then transferring it into something that like either storing the energy or carrying it forward. So the first time that I encountered a fly wheel was in two thousand and eight and I was in Lisutu, which is the landlocked country inside of South Africa, and we were working at an orphanage and we had drilled a well and we were going to put a pump on top of the well. And Masera, the capital city where we were at, had electricity, but in the two weeks we were there, I think it went out like eight times. So we didn't really want to put an electric pump on this well, and so I was thinking like, okay, we're adding a hand pump, and Jason, one of the guys leading our trip, was like, no, no, no, we're gonna put a flywheel on it. So instead of the hand pump, which would be this long handle, you go and pump your water and this the handle gives you leverage. But there's a direct tie between the effort that you put in and the impact or the results that you get back and at the moment you stop pumping, you immediately stopped getting water. And so instead of that, the flywheel is this large metal wheel that sits up on top of the pump. It's hard to get going initially, but instead of this linear up and down movement, it carries that momentum forward and it builds momentum over time. It's soon need an input, but I could basically with one or two fingers just keep this thing spinning. And so that's a metaphor. Obviously, like we get to apply it to all these other areas of life and business, and like we talked about health and business, that's a flywheel. It is incredibly difficult to get going. If you're starting with really small changes. You're just saying, oh, I'm gonna eat a piece of fruit every day. You can build on from there. So it really came to three laws that define a flywheel, especially in the business case. The first is every step in a flywheel should flow smoothly from one into the next. The second law is that it should get easier with each rotation, and then the third laws it should deliver more with every rotation. So that's flywheels at a high level, but and we can go wherever you'd like from there.

We will be back with Nathan soon giving an example of how he uses the flywheel framework in his business to drive sales. If you're looking for more tips to improve the way you work and live, I write a weekly newsletter where I share practical and simple to apply tips to improve your life. You can sign up for that at Amantha dot substack dot com. That's Amantha dot substack dot com. I would love to get maybe an example from within convert Kit in the sales process, because I think everyone listening will have some kind of a sales process in their business, maybe they are directly involved in sales. How have you gone about applying the flywheel concept to driving sales at convert Kit.

We will be back with Nathan soon giving an example of how he uses the flywheel framework in his business to drive sales. If you're looking for more tips to improve the way you work and live, I write a weekly newsletter where I share practical and simple to apply tips to improve your life. You can sign up for that at Amantha dot substack dot com. That's Amantha dot substack dot com. I would love to get maybe an example from within convert Kit in the sales process, because I think everyone listening will have some kind of a sales process in their business, maybe they are directly involved in sales. How have you gone about applying the flywheel concept to driving sales at convert Kit.

Yeah, so this tas in nicely with the kind of the pivot point that we talked about in Invertkit, because it wasn't just that I went all in on a convert it and like magically we got results. I actually did things differently when I made that pivot, and one of the biggest things that I did is I started direct sales being a content marketer. I I was thinking, I'm going to grow through content, right, that is how this business is going to grow. Turns out, it's really really hard to sell software through content, especially software that it's not very good yet because it's new, and so the pivot to direct sales really let me grow the company and get traction early on, especially because what happens when selling through content is if you and I are having a conversation. We're sitting across from each other at a coffee shop and I'm saying, would you like to buy convert it? Become a customer if you are like look at me and then like push back your chair and without saying anything, just get up and leave. That would be socially unacceptable on so many levels. Right. If I say, hey, will you buy this thing? You were obligated by the rules of our society to give me a response. It might be like maybe I'll think about it or no, but you have to give me a response. And whatever response you give me, I can learn from that when you think about content marketing. That socially unacceptable interaction happens all the time. I can just hit the back button. I've completely rejected you. You get no feed back, and that's what happens on the web. So I love it when people will go into direct sales because it gets them all of the speedback. So my flywheel for convertant direct sales like it worked, and then now years later, I'm like, why did that work? I'm like, that was a flywheel and I didn't even realize it. So I started just identifying potential customers. I looked at who was successful in convert it and I was like, Okay, let me find people like them that got me, like lists of men's fashion bloggers in New York Paley Arrecipe blog, try to get as specific as possible. Then I'd reach out with a personal message and I would ask about what was frustrating so specificly, I'd see they're using Mailchimp and I'd say, hey, I was wondering whether what's your biggest frustration with using Mailchimp. The reason I ask is I'm working on building a tool called convertt and it's used by and I would drop my the only two relevant names that I had that was a customer or someone else, And I just love to get your feedback, right, So I'd start with that it had a pretty good reply rate, and people wud say, oh, I'm really frustrated with it's hard to tag and organize my audio, it's hard to set up automations that are relevant to my subscribers, things like that, which very conveniently. I built the product because I used Mailchip, but I was frustrated by these exact same things, and so I'd say like, oh, here's how we're solving. I'd love to get on a call and show that to you. And that worked really well, and at some point i'd ask for the sale and they would usually say no now, thankfully because we're on a call. They had to tell me why. And the reason they said why was usually it's too much work to migrate. We've been using this other tool for three years, five years, and we're deeply embedded, until finally, like, out of desperation, like it's not that much work, blah blah blah, I'll do it for you for free. And that's where our concierge migration was born. And I would pull up their mailchim account and their converorking account here another like copy and paste over their emails and then edit all their forms and switch those over. And what that did is that's how I landed the customer, and then I would get a testimonial and the recommendation, Hey, who else should I get on? Convert it that recommendation The people completed the loop right. It brings my flywheel background to the beginning, because then now I've identified new customers. And so if we go through our three laws for this direct sales flywheel first is every step moves smoothly. Wanted too. The next right migration goes testimonial, which leads to new customers or new referrals that I can then talk to. Next. It gets easier with every rotation because my prospecting got more dialed in my cold email, I knew what worked. My sales calls got a lot better, the product got better, and then it also drove more results with every rotation because I could reach more and more people. Word of mouth started to kick in a little bit, and so I just noticed that that flywheel was so hard to turn it first, but it got just a tiny bit easier with every rotation up until the point that we just had a huge amount of momentum in word of mouth.

Yeah, so this tas in nicely with the kind of the pivot point that we talked about in Invertkit, because it wasn't just that I went all in on a convert it and like magically we got results. I actually did things differently when I made that pivot, and one of the biggest things that I did is I started direct sales being a content marketer. I I was thinking, I'm going to grow through content, right, that is how this business is going to grow. Turns out, it's really really hard to sell software through content, especially software that it's not very good yet because it's new, and so the pivot to direct sales really let me grow the company and get traction early on, especially because what happens when selling through content is if you and I are having a conversation. We're sitting across from each other at a coffee shop and I'm saying, would you like to buy convert it? Become a customer if you are like look at me and then like push back your chair and without saying anything, just get up and leave. That would be socially unacceptable on so many levels. Right. If I say, hey, will you buy this thing? You were obligated by the rules of our society to give me a response. It might be like maybe I'll think about it or no, but you have to give me a response. And whatever response you give me, I can learn from that when you think about content marketing. That socially unacceptable interaction happens all the time. I can just hit the back button. I've completely rejected you. You get no feed back, and that's what happens on the web. So I love it when people will go into direct sales because it gets them all of the speedback. So my flywheel for convertant direct sales like it worked, and then now years later, I'm like, why did that work? I'm like, that was a flywheel and I didn't even realize it. So I started just identifying potential customers. I looked at who was successful in convert it and I was like, Okay, let me find people like them that got me, like lists of men's fashion bloggers in New York Paley Arrecipe blog, try to get as specific as possible. Then I'd reach out with a personal message and I would ask about what was frustrating so specificly, I'd see they're using Mailchimp and I'd say, hey, I was wondering whether what's your biggest frustration with using Mailchimp. The reason I ask is I'm working on building a tool called convertt and it's used by and I would drop my the only two relevant names that I had that was a customer or someone else, And I just love to get your feedback, right, So I'd start with that it had a pretty good reply rate, and people wud say, oh, I'm really frustrated with it's hard to tag and organize my audio, it's hard to set up automations that are relevant to my subscribers, things like that, which very conveniently. I built the product because I used Mailchip, but I was frustrated by these exact same things, and so I'd say like, oh, here's how we're solving. I'd love to get on a call and show that to you. And that worked really well, and at some point i'd ask for the sale and they would usually say no now, thankfully because we're on a call. They had to tell me why. And the reason they said why was usually it's too much work to migrate. We've been using this other tool for three years, five years, and we're deeply embedded, until finally, like, out of desperation, like it's not that much work, blah blah blah, I'll do it for you for free. And that's where our concierge migration was born. And I would pull up their mailchim account and their converorking account here another like copy and paste over their emails and then edit all their forms and switch those over. And what that did is that's how I landed the customer, and then I would get a testimonial and the recommendation, Hey, who else should I get on? Convert it that recommendation The people completed the loop right. It brings my flywheel background to the beginning, because then now I've identified new customers. And so if we go through our three laws for this direct sales flywheel first is every step moves smoothly. Wanted too. The next right migration goes testimonial, which leads to new customers or new referrals that I can then talk to. Next. It gets easier with every rotation because my prospecting got more dialed in my cold email, I knew what worked. My sales calls got a lot better, the product got better, and then it also drove more results with every rotation because I could reach more and more people. Word of mouth started to kick in a little bit, and so I just noticed that that flywheel was so hard to turn it first, but it got just a tiny bit easier with every rotation up until the point that we just had a huge amount of momentum in word of mouth.

That's such a great story, such a great example. I love that, Thank you, David. One other thing I wanted to ask about is that you recently took a sabbatical. And when I read that, I thought, I need to take a sabbatical. I've been running my business Inventium for seventeen years, and I think the longest I've taken off in recent times is I don't know it, maybe two or three weeks. I'm craving it, but the timing is not right now because I'm hiring a CEO. How did you know it was time to take a sabbatical.

That's such a great story, such a great example. I love that, Thank you, David. One other thing I wanted to ask about is that you recently took a sabbatical. And when I read that, I thought, I need to take a sabbatical. I've been running my business Inventium for seventeen years, and I think the longest I've taken off in recent times is I don't know it, maybe two or three weeks. I'm craving it, but the timing is not right now because I'm hiring a CEO. How did you know it was time to take a sabbatical.

How did you approach it. I probably would not have taken a sabbatical if it wasn't for my team. We have a benefit at Convertant that when you hit five years, you get a month long sabbatical in addition to the month of vacation time you have every year. So sometimes people will take, you know, six or eight weeks sabbatical and I would joke like, I've been working on Convercure for ten years, so I actually get two sabbaticals now. And a few people on my team were like, no, but you need to take a sabbatical, and I was like, no, no, no, there's too much going on and all of that, and they just kept saying like you were setting the example for the team that sabbaticals are this thing that they should aspire to and are earned, and it's like, if you believe this, live it out. I was like, all right, and so I finally did. I had for probably a six months leading up to it, I had a doc outlining what are the different types of sabbaticals I could take, Because you could do an epic adventure. I'm going to walk the community to Santiago, right, or go on this epic vacation for the full time or something like that, or like I always wanted to learn to five plans, and I ended up just doing a combination of a few things. Mostly what I chose was learning and the staycation, and so I enjoyed life around Boise. We went on a vacation, I spent a bunch of time working on my pilot's lecense. I worked on a couple of things. We had some really big convertate things going on. So I think I took three meetings in thirty days. It was very weird for me to walk out of a meeting, like I'm used to sharing the work or something like that, and I could walk out of the meeting then I guess I'm just gonna go. So it's good to be a lot less involved in the business. But yeah, I think that it'd be really good pride for me to do every two or three years instead of you been every five years.

How did you approach it. I probably would not have taken a sabbatical if it wasn't for my team. We have a benefit at Convertant that when you hit five years, you get a month long sabbatical in addition to the month of vacation time you have every year. So sometimes people will take, you know, six or eight weeks sabbatical and I would joke like, I've been working on Convercure for ten years, so I actually get two sabbaticals now. And a few people on my team were like, no, but you need to take a sabbatical, and I was like, no, no, no, there's too much going on and all of that, and they just kept saying like you were setting the example for the team that sabbaticals are this thing that they should aspire to and are earned, and it's like, if you believe this, live it out. I was like, all right, and so I finally did. I had for probably a six months leading up to it, I had a doc outlining what are the different types of sabbaticals I could take, Because you could do an epic adventure. I'm going to walk the community to Santiago, right, or go on this epic vacation for the full time or something like that, or like I always wanted to learn to five plans, and I ended up just doing a combination of a few things. Mostly what I chose was learning and the staycation, and so I enjoyed life around Boise. We went on a vacation, I spent a bunch of time working on my pilot's lecense. I worked on a couple of things. We had some really big convertate things going on. So I think I took three meetings in thirty days. It was very weird for me to walk out of a meeting, like I'm used to sharing the work or something like that, and I could walk out of the meeting then I guess I'm just gonna go. So it's good to be a lot less involved in the business. But yeah, I think that it'd be really good pride for me to do every two or three years instead of you been every five years.

That is that is very inspiring, differently inspiring me to book something in Why Diari Now? Nathan, I feel like you're so prolific. There's so many different places I could direct listeners to to discover more about you and obviously convert kid. Where are the best places for people to go?

That is that is very inspiring, differently inspiring me to book something in Why Diari Now? Nathan, I feel like you're so prolific. There's so many different places I could direct listeners to to discover more about you and obviously convert kid. Where are the best places for people to go?

Nathanberry dot com is where I try to keep everything up to date the new I write a weekly newsletter every Tuesday. I host a podcast called The Billion Dollar Creator. But then I think the biggest thing is if you're looking to know more of my story than the documentary that the team forced me to make that's on YouTube, that's probably the best summary of life over the last ten years.

Nathanberry dot com is where I try to keep everything up to date the new I write a weekly newsletter every Tuesday. I host a podcast called The Billion Dollar Creator. But then I think the biggest thing is if you're looking to know more of my story than the documentary that the team forced me to make that's on YouTube, that's probably the best summary of life over the last ten years.

Amazing, well, Nathan, I'm so grateful that you said yes to this random reach out from Australia. I'm such a big fan of what you do, so thank you so much for sharing your time with me today.

Amazing, well, Nathan, I'm so grateful that you said yes to this random reach out from Australia. I'm such a big fan of what you do, so thank you so much for sharing your time with me today.

Oh, of course, thank you so much for having me.

Oh, of course, thank you so much for having me.

I hope you liked this chat with Nathan Barry, and I must say, ever since discovering Nathan, I have become obsessed with flywheels and thinking about different ways to apply it to my work and also at my company, Inventium. If you know someone that my benefit from this chat, feel free to share it with them via whichever podcast app you are listening to this episode from Following this podcast and leaving reviews helps How I Work find new listeners, and your support is one of the things that makes this podcast possible. Thank you for sharing part of your day with me by listening to How I Work. If you're keen for more tips on how to work better, connect with me via LinkedIn or Instagram. I'm very easy to find. Just search for Amantha Imba. How I Work was recorded on the traditional land of the Warrangery people, part of the Cool And Nation. I am so grateful for being able to work and live on this beautiful land and I want to pay my respects to Elder's past, present and emerging. How I Work is produced by me Amantha Imba. The episode producer was Rowena Murray and thank you to Martin Imba who does the audio mix. For every episode and makes everything sound better than it would have otherwise.

I hope you liked this chat with Nathan Barry, and I must say, ever since discovering Nathan, I have become obsessed with flywheels and thinking about different ways to apply it to my work and also at my company, Inventium. If you know someone that my benefit from this chat, feel free to share it with them via whichever podcast app you are listening to this episode from Following this podcast and leaving reviews helps How I Work find new listeners, and your support is one of the things that makes this podcast possible. Thank you for sharing part of your day with me by listening to How I Work. If you're keen for more tips on how to work better, connect with me via LinkedIn or Instagram. I'm very easy to find. Just search for Amantha Imba. How I Work was recorded on the traditional land of the Warrangery people, part of the Cool And Nation. I am so grateful for being able to work and live on this beautiful land and I want to pay my respects to Elder's past, present and emerging. How I Work is produced by me Amantha Imba. The episode producer was Rowena Murray and thank you to Martin Imba who does the audio mix. For every episode and makes everything sound better than it would have otherwise.