The True Cost of Growth: Nathan Barry's Honest Conversation

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So I ended up going from being, I think, one of the most like, productive, prolific people around to really struggling to function, both from the pain, from the brain fog of, you know, like serious prescription painkillers. And I thought that in a couple weeks I'd get through that. And what it ended up doing is like six months later, I still did not do much.

This is Reclaim in Advance, a social impact project where we host vulnerable conversations with modern day high performers exploring the lowest points of their personal or professional life, how they recovered, and their life on the other side of hardship. My hope is that you'll realize you aren't the only one who goes through tough times and there is a way out. Through these conversations, you'll gain inspiration from the grit and honesty of our guests and you'll learn practical tools and science backed frameworks that empower you to take on new challenges, regardless of how difficult they may seem at first. So if you're ready to join in, let's get started. Nathan Barry is the founder and CEO of Kit. The platform now serves over 600,000 creators, including Tim Ferriss, Pat Flynn and myself. But that kind of growth does not come without a cost, which you'll hear.

More about in this interview.

Let's jump into the convers.

Nathan. This is the earliest I've ever recorded a podcast.

I texted you, I was like, hey, I know it's 6:45 in the morning, but you want to record at 7:15?

Yeah, and I'm excited about this. I probably sound like I'm slurring to an extent, but. But no, like the opportunity to chat with you is just amazing. So obviously I can pass it up. So how about you describe where we're at right now? Can you do me a favor and just like to set the scene?

Yeah. So you mean where we are physically or where we are in time with the company?

Both. But if you do that, introduce yourself first.

So I'm Nathan. I'm the founder and CEO of Kit, which is a software company where we build email marketing products for creators formally or I don't, I don't know where we're at in this transition, you know, so it's formerly Convertkit or still Convertkit, soon to be Kit. It's like, basically yesterday we announced that we're going to be rebranding and we'll actually launch that in September. So it's fun, it's a great time. Then we're also now recording in the very first Kit Studios here in Boise. And this is a new concept that we're doing where it's five podcast studios, both a mix of recording like this, and then, you know, solo recording rooms if you want to do a course or, you know, remote recording. You recorded here a couple days ago with Gary Vee. And so, yeah, it's basically just another way that we can help creators, like, have an easier time going from an idea in their head to finished content. And so this is just available to all ConvertKit or all kit customers, Totally for free.

Yeah, yeah. And I'm taking advantage of it, clearly, so I appreciate it. But let's talk about what it took to get you to this moment in building convertkit now Kit. Can we just backtrack that?

Yeah, I mean, that's a big question. We've been at it for 11 years. And so, I mean, it started super slow in 2013. Well, it started fast. You know, you launch, you have all this excitement. And then my goal was to build the company to 5,000amonth in revenue within six months. And I blogged the entire thing in public every week. I was like, here's how I chose the name, here's how, you know, hired the first developer, all of that. We ended up getting to about 2,000amonth, six months in. And so it didn't have the, you know, the full start that I wanted, but, like, really, that was pretty good. And then it really just plateaued there. And for about a year and a half, we just were stuck there, couldn't keep growing. And I was doing other ventures. I wrote books and, you know, and had done the whole creator thing as well. And then a friend of mine really encouraged me to Double down on ConvertKit. So in early 2015, I decided to double down on it. And we ended up focusing on direct sales, like choosing, instead of going very broad and like choosing the niche of bloggers and creators and then scaling it up. And so after, you know, two years to 2000amonth in revenue, year three, we went from 2000 to 100,000amonth, and then year four was 100,000 to 500,000, and it's just been up from there. So today we're doing about 42 million a year in revenue, 56,000 customers, and a team of 80 people distributed all around the world.

Yeah, so I'm in town for the craft and commerce event. I was gonna say Craft and Commerce conference.

Yeah.

That's a lot of Cs.

That is a lot of Cs. So much to deal with that alliteration.

Yeah, the Craft and Commerce conference for creat.

Oh, yeah, we can.

It's too early for that shit. So I'm gonna say craft and commerce events, but this is an event for creators and it ruins every other conference for me just because of how amazing it is. And I'm not saying that just to be polite. Like, it's. It's amazing. But for people that attend, what is one thing you'd want them to say about it when they get home?

I think the people that they connected with, I think that's the biggest thing. We invest a lot in the content, right? You were one of our keynotes last year.

And why was I not invited back this year? Because we got to rotate through great creators.

It is funny though. There are people who are like, hey, was the talk not good last year? And you're like, there's so many people that we want to put on stage. So we invest a lot in the content and, you know, we get into how we do that and everything. But really it's just an excuse for getting a whole bunch of great creators in the room. Because for me, the most impactful thing in my career was meeting certain people early on. Caleb Wojcick, Barrett Brooks, James Clear, right? People who really early in my career we ended up meeting at a conference and building a relationship, forming a mastermind group and just investing in each other for years. And so that's the biggest thing like that I want people to come meet amazing creators who are thinking about, well, if we go to the name craft and commerce, some people are saying like, oh, I'm all. I'm entirely focused on the art and the craft of what I'm doing, and I'm not a sellout. And then there's other people in the world who are like, look, I'm just here to make money, right? The direct response marketing world, the, you know, the people who give a bad name to Internet marketing, right? And they just see their audience as like an ATM that they withdraw cash from. And so you end up with these two extremes and you think you have to be in one world or another. And so the name craft and commerce is just about the intersection of those two things. How do you have great art and hone your craft and really, really care about that and focus on making money, making it sustainable and building a valuable business.

Yeah. And one thing I can appreciate about the Vibe is, yes, there are some very successful creators, right. They're making a bajillion bucks a year. But there's also this, like, I would say, like middle class creators who are saying, hey, I make $60,000 a year.

Yeah.

But I'm doing it on my own time, my own schedule. I don't feel drained every day. And I think that's what really excites me about the creator economy. Like, you don't have to be a blogger with a bajillion views a month. You can say, hey, look, I used to work at this company. I hated it. Now I have my own company and I have full autonomy over my life. Right. And I'm not trying to be the next, you know, Gary Vee or, you know, Nathan Barry, anything like that. But you know what, I feel great. And I think you do a good job of celebrating that in regards to the content you're delivering, the people that you have here. So, like, all walks of life and all level of creators feel like they have a place here. So I think that's, it's amazing.

That's the goal. There's this creator that I met yesterday. Her name's Deedee. I'm not sure how old she is, but she's a grandparent. And her content is about helping grandparents. New grandparents know how to show up in this, like, relationship with their kids and their grandkids. Because there's so many complicated dynamics in that. Right. Of like, you know, maybe like, for us with, with our kids, we're very focused on healthy eating and like these good habits. And then if the grandparents come in and spoil everything because they're thinking like, no, no, no, you've got, you've got it all dialed in at home. So I'll be the fun grandparent who's just like, you know, ice cream and cake all the time, but there's all kinds of potential for conflict and, and this is just one of like hundreds of examples. And so she is so far from the flashy creator who's trying to teach you how to make the next million dollars on the Internet, but she's providing real value and like in, in this specific niche. It's like, wow, that is amazing to have that content. And she's just, and she's earning a full time living as a creator, you know, serving that audience. And so I just love that there's, you know, a huge range of people here.

Yeah, I met her yesterday actually, and I was so impressed. I'm like, you're like, got to be like the coolest grandma on the block. Like, oh, I have my online courses and all this stuff. And. And it's true. I mean, I think, you know, as a parent, you think, okay, I got to read all the books as a grandparent. So I came on a coast and she addressed. One thing I noticed with, with Kit is like, not to get too, too deep into the pricing, but, like, before was like, it was free for the first 1,000 people on your email list, and now you've said, hey, it's free for the first 10,000. And I'm curious why you opened it up. I mean, I'm happy about it. All the listeners, hey, check it out. But what made you, like, give that much access away for free?

Yeah, I was noticing a couple of trends. So first, people just growing much larger audiences than before and growing them much faster. And then especially as you look at creators who are growing on social media, like, if someone has Instagram dialed in, you can. I've seen people grow very, very quickly. And. And then they are hesitant to get into email because they're like, I don't actually know how I'm gonna monetize yet. And so if I'm so good at growing Instagram and then so good at growing my email list, like, this could be a problem before. You know, I might end up growing an email list that's very expensive to manage before I actually know how to make any money as a creator. And so we're trying to give them way more tools to make money, but also, we just want to open it up and have all of this headroom so that worry is gone, right? Because I see people, like, self sabotage for the most odd things because they're like, oh, I don't want to, like, hit this next subscriber tier or something like that.

Yeah.

And then the other thing is, our mission is that we exist to help creators earn a living. Right. And so it's as we achieve scale, then it's like, all right, we can unlock these other things and say, let's just reinvest that and give it back. And most creators that I talk to, they're like, I earn. Especially creators that, you know, who come to events like craft and commerce. They earn so much money from their email list. Yeah, the. The ROI is insane. And they're really h. Like, they're, you know, preaching like, hey, build a direct connection with your audience over email. So everyone I talk to is just like, great, I love that you Know, you're taking a portion of this and just reinvesting it into like the beginners coming up. And so I think what I wanted to do is make it so that whatever platform you're on or thinking of starting an email, it's like we, we can just remove all the roadblocks and make starting on kit an absolute no brainer. And so it's like, you know, a 10x we had the, you know, if you think of like 10x versus 2x kind of thinking, we're like, hey, let's double our subscriber limit. And we were like, okay, 2000. How would that be competitive in the market? Does that actually change your relationship with it? And it's like, well, if you're worried about hitting 1,000 too quickly, you're probably worried about hitting 2,000, so let's just go all the way to 10,000.

Yeah.

And then also like yesterday we released a bunch more features that are, you know, for the paid plans. Like we launched polls and that's a feature for the paid plans. So people will start to upgrade based on other things than subscriber limit.

You said you're like a mission driven company and it's easy to say that, right? I'm on a mission, 20 make money. Right. You know, like I'm not saying you, but like people say that, but your culture, it's very clear that it's mission driven. Because first of all, I know a lot of your employees are creators as well, right? So they're person, they're the, the personified version of who your audience wants to be. But also I realized like nobody leaves and if they leave, they come back. Like every time I talk to someone like, oh, I used to work at Convert Kid and they're at the conference and I'm like, sometimes when you leave a company, you do it with your middle finger in the air. You know, you're just like, peace. I'm never, I don't want to see the logo again. Yet for some reason, people just keep on coming back or just staying. So what is it about your culture that makes people want to stay? Or at least like they just still have an affinity for it once they do leave.

Yeah, that's interesting. That's a, it's a big question. And I think it's probably the amount that we care and take like care for and take care of people. And there are plenty of reasons that people leave both their own or we've definitely worked on building much more of a performance culture. And so we'll have those conversations with people and say, hey, thank you so much for your contributions so far. But we need someone as we go for a step function in this role, we need someone else in it, and we'll work on a smooth transition out, or that sort of thing. But I think it's just investing in people and building those relationships. Something that I try to do after someone leaves. I don't do it all the time, and I want to get better at it, but the habit that I'm trying to form is always sending. You know, like, last day, someone posts in Slack and says, like, hey, if you want to stay in touch, here's my email address. Here's my phone number. And I always wonder, like, who actually does that?

Right, right.

Because even if you're close with someone because of a work relationship, it's pretty natural for that to just fall off when you don't have. I mean, think of how many people you're friends with. You're like, oh, I haven't talked to her for a year. I haven't talked to him for two years. You know, and so I just always try to send an email or a text in the. Like in the two to three weeks after somebody leaves to just keep that relationship going. And I think it. I think it makes a big difference. And then also another thing that's easy to do is when someone leaves, you notice all the things that they weren't doing well. Right. Because now you got to come in and pick that up. And if I were to leave, someone would come in and start doing my job, and they're like, this is a disaster. Who was that? You know, because they get to see all the balls that I was dropping and everything else. And so I think it's really important to realize that we're all in that position. And so to just never, like, badmouth someone or anything like that. Or, like, you know, I don't know, now that Joe's gone, we gotta clean up this whole mess or anything like that. It's like, no, all of our work is a total mess. And so, you know, if you have that, if everyone sees you invest in relationships, even when that person isn't doing anything for you anymore, then it just sets that tone. And so we've continually had, you know, all of these team members who have gone on to do really great things, and they keep coming back to the conference every year. You know, we record podcasts together, we hang out, you know, and it's just. It's very meaningful to me.

Yeah, you said that's one habit that you're looking to get better at, which I think, you know, we all should. And I'm wondering if there are other habits that you want to develop, and I'll share one of mine. So I have four kids. They're 8, 6, 4, and 2 years old. So that's why I'm also tired. But. But one av we're getting into is just training them to be more optimistic, because, as you know, kids whine and complain a lot, and as you know, that's not pleasant. So what we're doing now is every day, their goal is to observe and report on three good things they've seen every day. Okay, so it could be like a classmate being kind to another classmate. It could be, you know, someone. A door from them, whatever it is, and then they report back, hey, here's the three good things I saw every day. Because that is how you train optimism. I got that from my buddy named. His name is Dr. Michael Gervais, because it teaches you to look for and expect good things to happen as opposed to focusing on the negative. So that's one habit we're getting into and then sharing these good things when we get home at the dinner table instead of complaining about, like, what kind of food they have or whatever.

Yes, exactly. You know, that never happens in my house. I don't know. I don't know what you're experiencing, but it's a perfect.

Yeah, yeah. So it's like, it's the reps we have to get in to build this more optimistic worldview. So I'm warning on your end what habits you're developing personally or professionally to continue ascending.

Yeah, it's a good thing. I'm working a lot on the habit of saying no because there's a. In your career path early on, all of the success comes from saying yes. Like, every. You're like, I don't know if this would be a good opportunity, but, like, I'm gonna jump on a plane and go, like, I got just this little opportunity to meet this one person. And, you know, you don't know what will come from it. But, like, you say yes, and you go do it. And then that drives so many results. And, you know, people talk about, like, oh, you just got lucky. Well, saying yes a lot is how you increase your luck surface area, you know, and your opportunity to, you know, potential to get lucky now on from there, there's a certain point where focus becomes so much more important. And you have to say, you know, you now you go from chasing opportunities to now you have Too many opportunities coming to you and you have to curate and really focus on them. And so I've struggled to make that shift. I get new opportunities coming in and I just want to say like, yes. Oh, that's amazing. And I'm just, I'm so thrilled that people want to partner in these ways, do these things together. And so I think Jason Freed from Basecamp talks about how yes is a blunt force instrument. No is a very precise instrument, meaning that if you say no, you're saying no to exactly that one thing. You know, it's like a scalpel. It's very precise. If you say yes, you probably saying no to a whole bunch of other things, maybe other commitments or something else that you can no longer do because you're over committed and you don't even acknowledge those things. So you say yes to a bunch of things. You let everybody down, you execute poorly, whatever else happens. And so that's something that I'm working on, is trying to be like, okay, this is what we said we're gonna do. Yes, I have a hundred other good ideas, 100 other incoming requests, but no, this is what I'm focused on and we're going to stay true to that.

You were nice enough, or ConvertKit or Kit was nice enough to record my story through a documentary last year. Just sharing my ups and downs and how I navigated some situations. So. So thank you for that. I mean, it was an amazing experience. Your team came to my home in Brooklyn, recorded all this content with me and my family. And for a moment, Henry, Henry Thong, he was. He was actually watching my kids for me because I had to run an errand.

So I was like, Henry's the best.

This is like a full service crew here, which was great. And it feels great to have this anthology out there of my life or documentary of my life out there and talked about some things that were very, very sensitive and not. Not easy, but necessary. And you have a documentary through kid as well.

Yep.

Which I saw last year. And what I really appreciated about it is we see people like you and we hold you in such high regard. Like, oh my God, Nathan's like, you're doing all these amazing things, so on, so forth, so successful, so kind. And it almost makes it seem like you're not you. But people like that are unapproachable at times because it's like we can't relate. You know, you haven't struggled, but you, you clearly have. And, and I appreciate you telling that story. It's great to have your mom There too, like to witness that. So what I'm teeing up here is I would love for you to share, like, any part of that journey that you feel comfortable opening up with today.

Yeah. So first we did all these documentaries we've been doing that. The series is called I Am a Creator and we've done them on. So many great creators are just telling these stories of, of their life and, you know, it's hard to edit it down to a 20 minute, you know, documentary. But Henry and Issa on our team do such a good job. And Issa made this comment, she goes, you know, like, Nathan, at some point we need to tell your story. And I was like, yeah, no, let's focus this on the customers. And she just kept coming back and being persistent. And we really, the team put together more marketing language and stuff around convertkit now kit being made for creators by creators. And so she's like, nathan, you're a creator. We got to tell your story. And it was one of those things where inside of like, she was saying that and it's a, like, it's a fairly reasonable ask to be like, great, let's, you know, we did the document on a whole bunch of customers. Let's do one on you. And I, like, intellectually was, was sort of like, no, I don't want spotlight to be on me, but like, deep down, emotion. I was like, if I'm going to do this honestly in the same way that like, and tell the full story, then I have to tell the full story and I don't want to do that.

Right.

And so, like, she was persistent probably for three years to be like, you know, and she was nice about it and everything else, but just really pushing. That's.

You got a lot of practice saying no over those three years.

Yeah, exactly. Thanks, Issa. A lesson, you know, be persistent.

You'll eventually get what you want.

But the thing is, I didn't want to tell the story because I knew that I'd have to authentically share so many of the struggles. And so my story as a creator, you know, there's always two tracks going on. Like, there's, you know, the surface of what everybody sees and then there's like, what's underlying it. And so on the surface, you know, I grew up in a family where money was pretty scarce. I decided that I wanted to get good at making money. I learned from Jason Freed from Basecamp that making money is a skill, really the collection of many skills that you can practice just like, you know, playing a musical instrument or Something else. And, you know, so I went, did web design, then software design, did the creator thing, built ConvertKit. It ended up being super successful and on from there. But the other side of it, you know, underneath that is I didn't realize how much watching conflict around money, like, really shaped me. So as a kid, I watched my parents fight about, really, the lack of money. And I really, like, grew up with this feeling of being a burden on other people. There was this interaction. My dad worked for, like, ran this Christian ministry, and it was like, to college kids on the Boise State campus, and they had. They did really a lot of good things in people's lives and facilitated so many great conversations and all of this stuff. But the parent company or the parent organization that I was part of had this idea that in order to be in ministry at this organization, you had to meet the standards of a pastor in, you know, in a church, basically, as far as, like, how your family behaves and all of that. And so one of the. The dynamics that came up is when we would, you know, misbehave as kids. It would. At least the way that I internalized would come back to, like, hey, if we don't run, like, if. If you don't behave as a kid, basically that means that, you know, for my dad, I'm not running a, like, Christian household, which means I'm not eligible to be in ministry, which means that, like, our livelihood is at stake. And, like, I really internalize that of, like, oh, I'm just feeling like I'm a burden on other people. And so, so much of my drive came from, I will never be a burden on someone else. Like, if I can make sure that I'm the best in the world at making money and taking care of everyone else, that I will never be a burden on them. And that way I can make sure that, like, I never feel that again. And, like, watching the conflict between my parents, watching them divorce over, you know, many things, but money being a big part of that. You know, I was thinking, like, watching all that happen, I was thinking, that will never be me. And so I. I, like, went through that journey to get as, you know, as good as possible at making money so that my wife and I would always have an abundance. And I. I had so much of a drive to get everything done. Like, my creative journey really kicked off when I started writing a thousand words a day. And I did that every day for 600 days in a row. And so in that time, I built a blog, an email list. I wrote three books. I made $500,000 selling digital products. I launched my entire career. And I really based all of that on my idea, my ability to execute and deliver. And then it was actually, I guess, the beginning of June 2014. So exactly 10 years ago, when we're.

Recording this.

Maybe off by three or four days.

Yeah. Yeah.

Okay, that's interesting.

Yeah, There we go.

I was gearing up to have the biggest year of my career. The first three or four months of the year, I was making $50,000 a month and just rolling with everything, working like crazy to do it. We had a two year old, and then our youngest was just, you know, now our middle child was just born and we were also. We had moved and we were remodeling a house and all this stuff was going on and I just had it. I was trying to do it all. And it was. It totally worked up until both kids got sick, like at the same time. And, you know, so we had a two year old and a two week old. And I was trying to juggle everything and use these habits and skills that had served me so well over the previous, you know, eight or 10 years to just take on everything. And then I noticed that I had this rash on my leg and I was like, that's weird. And first did we change laundry detergent? You know, I'm trying to figure out like, allergic reaction to something.

It's definitely not me. It must be external.

Yes, exactly. Always. And I texted my brother, who's a. He was a combat medic in the army and now he's a pa. And I was like, hey, like, I have this rash on my leg. What might it be? And you know, like, should I go in for it? I don't know. And he just goes, does it follow a dermatological distribution?

I'm like, what the hell is that? Even?

I don't know what that means. And you know, like an older brother, he goes, google it. And so I Google, and it basically means, does it follow the pattern of your nerves in your body?

Okay.

And I look and I'm like, 100%. You know, it's like here and here, but it doesn't cross center line. He's like, yeah, you have shingles, Go to the doctor. I'm like, shingles is what people get when they're like in their 70s. You know, I'm 24. Yeah. And so I go into the doctor and they, you know, they're like, yep, we've got shingles. You know, here's antivirals to take care of it. Here's like serious painkillers to deal with the pain from it. And I was like, love it. Take the antivirals. I don't need the painkillers. Like, it's, you know, discomfort kind of painful, but like, I'll be fine. Yeah, I'd broken my leg as a kid and I just hated what, like hydrocodone and all of that, like the way that it makes you feel and brain fog. And I was like, I got too much to do, got a family to take care of. And actually it's kind of funny. So they were like, okay, you sure you don't want the prescription for that? And I'm like, yeah, I'm sure. Right. So I go pick up my antiviral prescription. And then that was like 10 in the morning. At 2pm I called them back and I was in so much pain that I was like, I actually need that.

Give me the drugs. Yeah.

And they were like, oh, we know. No, we actually already called in. Like, we submitted both prescriptions at the same time and we just knew, like, instead of convincing you of it, we just said like, okay, we'll just wait. And so I ended up going from being, I think, one of the most like, productive, prolific people around to really struggling to function, both from the pain, from the brain fog of, you know, like serious prescription painkillers. And I thought that in a couple weeks I'd get through that. And what it ended up doing is like six months later, I still did not do much, right. What I realized is I would sit down, you know, like after, I think, I think I was probably on painkillers for about a month and, you know, gradually tapered off. And then I would sit down to work and get something done. And I, like, couldn't get words on the page and I couldn't do these things. And the less productive I was, the more frustrated I got. And what I learned after a lot of therapy later is that I tied my self worth to my ability to create, to be productive. And so I ended up falling into a deep depression. And basically in my content, I talk about flywheels and virtuous cycles, right? But you have to realize vicious cycle, it's a nice edge between virtuous cycles and vicious cycles. And so I got into this vicious cycle where the less I could create and get things done, the more I struggled and the more it affected my ability to get things done and down and down from there. And I ended up going back to this place from childhood of just feeling like I'm a burden on Other people. And so it took. It was probably six months before I got to the breaking point, when a good friend of mine was like, hey, you. You need help. Like, you need to go to therapy. You need to talk through this. Because I basically spent six months, like, not really doing much of anything and just. Yeah. Being in a deep depression.

And, like, what was your wife doing during that time? Because, like, you know, she's seeing these things.

Yeah.

And I think sometimes, like, you know, with a partner, they're like. They'll give little hints, like, hey, maybe take a break or it's going to be okay.

Yeah.

And that doesn't help. And then, like, my dad used to say, like, the things that you worry about will become your reality if you don't address them. So during that period between, like, you know, when your friend confronted you and, you know, when you started the spiral, like, what was that like in your. You know, with your relationship with your wife? If you feel comfortable talking about. I'm just curious.

Yeah. She was just. I think she didn't know how to handle that. That shift. She was just really supportive. There's a lot of it that I think she probably didn't see, and I didn't know enough to, like, talk through.

It.

That would require a level of vulnerability. And, like, I was so subconsciously so dead set on taking care of everyone.

Mm.

And not being a burden on other people that, like, I couldn't. Basically suffered in silence.

Yeah.

You know, and so a lot of it, you know, would spend in my office, like, just getting more and more upset and, you know, and. And depressed. And so, yeah, she just watched this, like, gradual. Gradual spiral. And. Yeah, it was just. It was a long time. I ended up, like, working through that, but I. I felt like something fundamentally shifted in me, I think dealing with depression and suicidal tendencies and. Or, like, ideation and all of that. You know, it's interesting. My team gives me a little bit of a hard time because I cry really easily now. And, like, even though my keynote yesterday, like, there's just people. Like, you were. You were a little emotional on stage, weren't you? It's like. Yeah, but, like, I. Before, you know, 2014, 2015, I. I never cried, like, ever. And so, yeah, it was a big. A big shift. Yeah.

I'm just still amazed at how much our childhood impacts us as adults. And I was talking to Barrett Brooks about this yesterday. It puts even more pressure on me as a parent to, like, not mess up my kids. And you mentioned, you know, scarcity of resources. I remember One time when I was younger, we got a bill in the mail, and like, one of my. One of my siblings saw it, and they're like, we're poor. We got a bill. So we did all these things to try to save money because we thought we were poor. And including, like, reusing the same bath water and stuff like that. Like, it was just like, not a good look. Right? But. And eventually my dad was like, what are you guys doing? Like, you know, look where you live. Like, you're okay. Yeah, but. But it sticks with us. When you kept on saying, I didn't want to be a burden. And that's what I was asking about you and your wife, like, not even being open up to your wife about these things. You don't want to burden her, but she knows something's up. Then she's like, is it me? You know, what's going on? So, like, there's all this compensation that takes place, which is not beneficial because you don't get to the root issue. And I think you eventually opening up, obviously, then it helped resolve things. But what I'm curious about is, like, these days, when you're faced with some kind of adversity, have you now built the resilience to say, look, I've been through some. Like, I'm feeling this, you know, this, this tingle, you know, like this, this, you know, something's imbalanced, but you just know how to better address it. And I don't think this too much of a leading question, but how do you deal with adversity now based on your experience in the past?

The hardest skill for me to learn. Skill. I don't. I don't know if that's even the right word, but just the ability to ask for help because, you know, if you. If you meet or talk to someone and they're so, you know, they're so helpful and caring and, you know, everything else, well, you don't realize that could be for so many reasons. And, like, I was that person. I took care of everyone, you know, like, oh, you're moving houses. I'm there with my truck. You know, like, all of that. And you could do that exact same behavior for very different reasons. And I didn't understand this, but I did it from the place of, if I give you more, then that way I can make sure that this subconscious internal scorecard means that I'm giving more, pouring more into you. That way I can be certain that I'm not a burden on you. And so it's. It's not healthy at All.

Yeah.

And then also when you get to the place of like, oh, you know, self worth is connected to output, you know, and you think like, oh, I matter because I take care of these people. I matter because of what I create, what I earn, all of that. When really, like, to be able to end that sentence earlier.

Yeah.

To just be like, I matter. Like, you know, well, I matter because you're like, oh, no, you actually went a little too far in that sense. The period goes sooner. It's just I matter, period. And that's just a totally different, different thing. It took me a long time to internalize that. And so basically that, that, that push to not be a burden on other people meant that, like, I could not ask for help. And so that was the biggest shift. Like, I remember a time being at a conference, this is probably, I don't know, maybe 2018 or something like that. And being at a conference where someone talked, like, told their story and it dealt with their brother's death through suicide. And so many of those things, I remember thinking before of like, you know, someone say, like, oh, that triggered me for a story, and I was like, how weak are you? Like, what? But being in, like, hearing that story, I was like, whoa. That was like. It brought up so many things for me that was very, very, very triggering. And being at this conference and like, going back to my hotel room and realizing, like, I'm not okay, you know, and just not knowing, you know, I'm in a different country. I am. I have friends there, but now it's like 11 o' clock at night and, you know, and I don't have friends that I'm that close with at that event. And I ended up, like, I think, I mean, it was midnight back at home, and I ended up calling my friend Ashley, who was the one who had, like, really pushed me to go to therapy and, and all of that. And like, just saying I'm, I'm not okay and I need to talk to somebody. And like, that was a big, big deal for me especially, you know, to. To like, even call a good friend at midnight and be like, hey, I, you know, feeling like this is. I'm putting a burden on you and all of that. But, like, that was a really, really important step for me is to be able to ask for help and to say, like, yeah, in this moment, like, I'm absolutely burdening you with, you know, what I'm going through. And then to be able to accept that help, like, was such a big pivot.

Something you said earlier is, you know the power of saying no. You have to say no more often. But you yourself know the value of the other people saying yes to you and helping you along the way. So I'm wondering, is that another reason why it was so challenging for you to say no before? Because you know what a yes can unlock in people's lives, and you feel like maybe you could be that person to unlock that opportunity for them as well?

I think that's probably true. Yeah. And there's so many people that have given without the expectation of anything in return, and, you know, the impact that they've had. And so there's this desire to, like, so many people who do amazing things for you. You're like, I want to pay it back somehow, and, you know, the much better way. Often people who do it from a place of abundance and everything else, they're like, I don't. I don't need it paid back. Pay it forward. That would be amazing. You know, and so, yeah, those ideas of people who have had a huge impact on me and my life. And so then, yeah, I feel that, like, desire to pay it forward. I was gonna say obligation. I do feel that obligation. But I think it's really important to at least understand the nuance there. You know, I used to do so many things out of obligation and that. Like, how do we keep that scorecard to make, you know, to make sure if I said I was going to do this, I'll follow through. I didn't want to cause any burden on you because I'm backing out of a commitment or whatever else. And so I think, you know, just become so much more aware of that. To be able to do things from a place of desire rather than obligation.

Desire rather than obligation. I like that. Well, you're about 15 minutes away from getting on stage again, so I. I do want to let you get out of here, but I'm going to ask you a very difficult question.

Yeah.

And you're a creator, so I think you can get through this one. But if you're. Someone wrote a book about your life, what would this chapter be called that you're embarking on right now? What would the title that chapter be?

Dreams Realized. And what I mean by that is I've had a really. I don't know, my relationship with my own dreams and vision for my company and for my life has, like, I guess, has been tenuous in a lot of ways because I spent so much time. You know, if we go back to childhood, it's like watching so much conflict and all of this that, you know, I just like. My tendency is I just want to make sure that are you good? You know, everything okay? You know, and all that. And so that even plays out when I have a vision for the company and the creator community that when people are like, oh, I don't want to do that, or that's not a good idea, I'm like, okay, we can pivot to make that work. We can accommodate everyone. There's some common ground that we can find in everything. And I've spent a lot of time doing leadership through consensus, which is really not very effective. In case anyone's wondering, it may sound good, it's not. And so there's. I'm really big fans of the organization Reboot. Jerry Colonna founded it along with Dan Putt and others. And there's now, there's a book called Reboot, there's a podcast, and they do a lot of coaching. And so Dan, one of the co founders, has been my coach for the last four or five years. And in Reboot, they talk about this idea of taking your seat as a leader. And that's something that I've been really trying to do. So instead of leading through consensus and making sure we're all on the same page and finding the compromise and everything else instead, asking questions, understanding, and then making a clear decision. And that's what I've been trying to do so much of. Like, we're sitting in a podcast studio that the WI fi password. I was surprised by this. Like, Haley on my team, who. Who executed on this whole vision, came in and was like, oh, Hayley, what's the WI fi password? She goes, ConvertKit 2018. I was like, what, Hayley, I don't know if you know, but it's 2024 right now. And she goes, no, 2018 is when you first pitched the idea of building out these studios and community spaces for creators to the team. And we, like, I remember that moment exactly. And we have executed on that. And it was something where so many people were like, you can't do this. It doesn't make sense.

How are we.

We're going to pay someone to be here and physically manage a podcast studio? You know, you're going to launch a bunch more of these in a bunch more. You know, like, none of this makes sense for a software company. And really, in the last six months, in the last year, I've worked really hard to take my seat as a leader and say, I have a vision for this company. This is what we're doing. Here's where we're going and be totally okay with the fact that I don't need to change it to accommodate what someone else thinks. And so in. In my keynote, I talked through, there were three big things that I've always wanted to do. One is build an app store on top of ConvertKit so that anyone can extend it. There's actually four big things. The first is the App Store, and that's such a huge undertaking. My whole background is in software, and I know how hard that is to get right. And our team was just like, without twice as many people, without, like, it's not possible. And I just kept thinking, like, nope, this is my vision. I believe in it, and I would have done it years ago if I had taken my seat as a leader. The second thing is I wanted to make a product that's just wildly accessible. I don't care about making money from beginners and people just getting started. And so to do something like launch our new newsletter, free Plan, where it's just wide open, you know, 10,000 subscribers, just ridiculously so. The next thing is, I always wanted to do these, like, podcast studios and creator spaces. Like, I just wanted to say, you could walk in, sit down, hit a single button to hit record, and, like, we can have this great conversation and just make that available. And the last one is, I always wanted to rename the company. I felt like ConvertKit is a name that was really good for software to help you convert visitors into customers, you know, but, like, we built a product that's way bigger, and they had a vision that's much, much bigger. And, you know, that was something that I felt strongly about for years, attempted to do once, failed at. And, you know, I was like, I still want to do it again. People are like, you can't. That's ridiculous. On from there. And so when I was giving my. My keynote yesterday, I said, you know, I got emotional at certain times where, you know, it wasn't like I was telling some really difficult story. And my friends, Justin and then Barrett, who you were just alluding to, we were out here in the podcast studio yesterday. And Justin goes, you got a little emotional in the talk. What was going on there? And before I could answer, you know, Barrett goes, might it have something to do with the fact that the things that you've dreamed about for years are actually happening now? Like, those dreams are realized. Might that be it? And it's like, yep, that is exactly it. Of, like, these things that I've wanted to do for so long, I have, like, taken my seat as a leader and said, yeah, I'm absolutely going to do them. I have this vision for the creator economy. I'm going to bring it to life. And, you know, even if that means people won't be happy with it or there's going to be way more work or. Or something else, you know, it's just. It's been an entirely different way to show up and lead and it's just fantastic. So, yeah, that's the chapter of. Or the title of this chapter, Dreams Realized.

And what I appreciate is your dream isn't just about you. It's about a lot of other people like me, like, like our listeners and like everyone you're helping through Kit. And I appreciate you. I appreciate your time, appreciate your vulnerability, your empathy. Just everything about you is inspiring. So thanks for this. I know I have to run, but I appreciate it.

Yeah. Thank you.

Awesome.

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