How I Built a 50M/Year Company: Frameworks & Reflections

This is the framework. This is the physics of money and audience. And once you understand it, your entire future is in your control. Usually I'm the one asking the questions on the show, but today we're flipping things around. For the last 6 years, Dan Putt has been my coach. He's seen the highs and lows, the lack of confidence, and the hard decisions that come with building a company.

So what has changed for you? What has allowed you to be more confident?

One thing that really helped me was realizing the impact I was having on other people. A phrase you would use is take your seat as a leader. We were just not functioning as a leadership team at this company. I said, this is what we should do and here's why. And I like stepped in. Everyone settled and everyone was like, okay, that's clear.

And that's literally taking your seat.

Yeah.

Let's bring the 13-year-old in. Like, what would he think?

13-year-old me would walk into the studio, but he'd be more impressed with The other 4 studios that are open, like the tools for everybody else to create whatever they dream up.

I think one of the things I have seen not change is the why you're doing this.

I felt like I had discovered the cheat code to all of this because people say like there is no cheat code, but then you discover it.

That's amazing. It's an unstoppable force.

Dan, welcome to the show.

Thanks for having me.

So we've been working together for 7 years, 6 years.

7 years?

6 years as a coach. We met 7 years ago.

Oh, that's right. That's right. Yes.

And we just hit a fun milestone at Kit of $50 million in ARR. We're a little past that now. And I thought it'd be fun to have you on the show and reflect back on just that journey. And so, you know, in a minute I'll hand it over to you and let you interview me for the show. But I was looking at some of the numbers. We were texting about this actually a few weeks ago. And when we first met was through an event that you hosted at Reboot where, what was that, like 15, 20 founders altogether in Colorado? 3 or 4 days. How would you describe that event? What is it?

We called it a boot camp, and it was less of the physical demanding and more of the emotional introspective demanding experience. But it's just a chance for founders, leaders to come together, talk about the challenges, better understand the best aspects of them showing up to their company and their leadership and the worst aspects. And then really, who am I and who am I becoming as a leader?

Yeah, it was very powerful for me. And so I felt like I got a ton out of it, not just friends and relationships, but also like it was a step function in personal development for me. But I was looking back and when I went to that, Kit was at $12 million in ARR. And then a year and a half later, we started formally working together, you know, in a coaching relationship and we were at $18 million in ARR then. And then fast forward 7 years or 6, I guess 6 years, and now we have blown through $50 million and accelerating from here. So in the spirit of doing a milestone episode and kind of talking back on that journey, I feel like I'm a pretty different person. And you've had a front row seat to all of that. So I'm curious, what are the things, as I hand it to you, what are the things that you would talk about that you think listeners might find interesting or be like, oh, if you knew what went on behind the scenes? You get to ask all the questions.

I get to ask all the questions. I feel like such a privilege here. You have changed a lot. I'm wondering if you— and I'm responding to your question with a question, which is what I do. It's my default mode. But I wonder if we could sort of imagine the Nathan of 2019. How old were you at that point?

29.

29.

I was born in 1990. So basically whatever year it is.

Okay. So if we had the 29-year-old Nathan walk in the room, I mean, first of all, what would you know about him? Would you notice about him? What was he struggling with at the time? Can you remember that?

He wasn't nearly as confident. And not to come across now of like, oh, I'm completely confident or like arrogant or anything into that. It's just like, I think there's a lot of second guessing. And especially around leadership and team, probably a lot of trying to figure things out, not particularly emotionally aware. That's been a— the whole EQ side of it has been really a lot to learn. And then probably optimizing for a lot of the wrong things. And an example of that would be in trying to get other people leading through consensus. That was a big thing for me. And thinking that if I was like, well, what do you think we should do? And let's, okay. And we all agree. Okay, great. Thinking that that was a big positive thing when actually it, and we can get into that more, made everyone so uncertain and lack confidence and it just caused chaos in the leadership team and the organization and all of that. And then I think probably the last part is I was still very much leading really trying to take care of everyone else so that I wouldn't have to ask people for something. I could always make sure that I was giving more in the relationship than I was getting back. I would not be a burden on someone else. I can be very confident that, you know, I've done more for you than you've done for me. And that way, you know, I can know that I, yeah, wasn't a burden on you in any way. And doing that like all across the company, basically all across all my relationships. So there's a laundry list of things.

I want to go through all of those. I mean, if we were to go through those pieces, the ways in which you have seen the ways you've grown, so the 29-year-old Nathan was less confident, consensus-driven leader, certainly focused on taking care of everyone else first, right? Is how you—

I mean, that's my way of putting it, not yours, but where in the past I would feel like, one, I'm not even certain that this is the right move, so let's talk about it for 3 months. And then two, even once I'm certain, then okay, that means that I have to have all of this figured out. And so then let's make a plan for another 2 months before we finally do that. And I think what I would project during all of that time is like uncertainty. To everyone around. And so people would either say, where do I stand? What are we doing strategically? We're not making clear decisions. Do I need to step up and convince Nathan that this is the way to go? All of those things. And so those are some big changes.

How would you say your relationship to uncertainty has evolved?

I don't know who it's a quote by, but people talking about one-way doors versus two-way doors.

I think that's Bezos. Or at least he has popularized it.

Yeah. And so I think about that a lot. I think that's something that comes up with like, well, is this a reversible decision? And often they are, right? You know, we're like, oh, if this doesn't work out or if this doesn't work out, you know, we can go back and try something else and we will have lost some amount of time and money, but, you know, not reputation or relationships or some of these things that matter more. And then the other side would be when you're like, okay, this is more of a one-way door. And, and that what would make it that is either like you're really trying to capitalize on a moment in time or there's something that if it doesn't work out, there's a big reputation hit or a big relationship hit. Um, you know, if you're changing something with personnel, like you can't, that person no longer works at the company. You're like, oh, but you were actually good. Like you want to come back. Probably 9 times out of 10, it's like, no. Um, probably putting it in that framework. And then also I think I really looked a lot before as to whether or not there was a right answer. What is the right answer? Not that I'm a pure relativist now or something, but I just don't think— I think there's a lot of right answers to most problems. How do you think about that?

Well, my colleague, mentor, Jerry, I think he stole this from his therapist, but he would always say that there's a right way, there's a wrong way, there's a way that works. Just figure out the way that works. I think kind of to the framework of the one-way door versus two-way door, I think what I'm hearing in the way you describe it, which I agree with, is recognizing that the stakes aren't always life or death. And sometimes I see founders and leaders get stuck on this. All the decisions feel like life or death decisions, and therefore I'm stuck in this analysis paralysis, whereas I can recognize actually the stakes are low here. The higher risk thing is delaying. You're dragging your feet on it. And I will often quote this, and somebody's going to probably prove me wrong on this, but this Harvard Business, I think it was a Harvard Business study of essentially the effectiveness of decision-making from CEOs. And they found roughly that a third of the time decisions were negative, a third of the time they were neutral, a third of the time they were positive. So the way I think about it is like, okay, two-thirds of the time you're going to make a neutral or a positive decision. So speed is more important than right.

Okay.

Yeah. But, you know, I think what I have seen in you is a recognition that you can recover from wrong mistakes. You can survive them, which I think a lot of folks don't understand or get. And that can come from also being like, I need to be the leader that has the answers and is strong and steady. And knowing that you don't have to be that. It's okay if you make bad decisions, if you can correct them. And actually, mistakes are places to learn. So I've seen that in you too. But I hear though that you didn't put it this way, but the way that I heard it was, and it just feels different to make decisions than it used to. Feels like it may have been a lot more scary, a lot higher stakes, a lot riskier, whereas now it's less so.

I think it's the difference between making the right decision and the best decision. And best decision is not framed within all of the information known to mankind and all of the time available, it's like the best decision for this moment. And so actually having, like being willing to accept making the wrong decision. And so that goes to the Harvard study of like, look, if you're going to be wrong or neutral, take your time.

I may be wrong about that being a real study too, by the way.

Someone go ask their AI to look it up and we'll see. But realizing like my job is to collect the information and make a decision from there. And a clear decision is so much better than hanging out in uncertainty. This is something that I learned from one of our product leaders who was at the company for a few years. She had sold a startup to Walmart. And so then she stayed on as a, like a senior director or VP at Walmart in their Walmart Labs division. And the leader that she worked for was really good, was not consensus-driven at all. And so you think like, oh, they're not listening, they're not, maybe that shows up as a dictator. I would've thought that. But what this leader did is they'd gather everyone around and say, here's the decision that we have to make. What do you think? What do you think? Go around and be like, okay, thank you. All right, Dan, you win this time. We're going with your plan. "Here's why." And they could go and reflect back to every person. So first they would do, they would reflect back what each person said and to the point where everyone's like, "Oh, you understand my argument and my case as well as I do, sometimes even better." And then they'd make a clear decision. And so realizing that my job was not to make the best decision or the— it was not to make the right decision, because I can't truly know what's the right decision.

Yep.

My job is to go and collect the inputs, make sure that I truly understand that, to make sure that each person is heard. So I didn't just be like, that was a dumb, like, dumb idea. Next, right? Or whatever. Um, if I can articulate that, you know, 90% as well as the original person can, like, that's great. And then to make a clear decision and everyone will accept that and move on. And they might not think that it's the right decision, but they can see the whole process unfold and they can say, I was heard. I said what I should have. I was clearly heard. And now I can execute on it. Another Bezos would be disagree and commit. And that was so freeing because then the difference between my job is to make the right decision And from my job is to listen to the inputs, reflect them back, and make the best decision that I can in this moment.

I love that. I mean, I will, I probably have said this to you. I always tell leaders that your job is for people to feel heard, but you don't have to listen to them. So you can, you want them to know that you hear what they're saying, but you don't have to do what they say.

Yeah. And that was a huge hangup for me. Right. Because the way, the way that I felt to make someone feel like I was listening to them and that I heard them was to do what they wanted me to do.

Yeah.

And it's not the case at all. Like you have to separate those things.

So when you think about, I don't want to come back to the thread of the 20, 29 or the 29-year-old version of you. But when you think about, um, so your job is to make the best decision, not the right decision. Right. How do you know when a decision is the best decision?

I think one of the first things is getting clear on the timeline to make the decision.

Okay.

Before, I used to think that if you let it extend for a long period of time, that was fine. And now, this would be a big shift for me over the last 6 years, I think that time is very, very expensive and not just the time of sitting down to do a task, But the time that you let things go by, you let uncertainty persist or you let the lack of a decision go on. And so there are some things where you're like, oh, I'm going to deliberately not decide this because it's not important. But for the most part, if you were to leave all these outstanding decisions, like they actually cost energy and they cost time. And so like we have a, just a simple Google Doc that we keep track of, like what are the decisions that we need to make? And they're just categorized into a now, next, later, right? Of like, we're deliberately not making these decisions now, so we can get rid of some of the overhead there in the later bucket. Next is like we're collecting information. And then now is, no, but really, you are costing uncertainty, overhead, whatever, for as long as you don't make this decision. That's a the next 24 hours or by the end of the week kind of bucket. And that helps a lot. So a clear view on time. I think the second thing is getting a sense of the information that you're trying to collect. Like who are the input providers? Whose voice matters? Because knowing that there's an infinite amount of information you could collect about any decision, where you're like, well, I haven't gone out and read the 5 books on this that I could, or that sort of thing. So just saying like, this is the information I'm going to collect. Actually, Brian Armstrong from Coinbase has a decision-making framework. It's like a blog post that he wrote on Medium years ago. That blog post has made me a lot of money because it helped make clear decisions where he's just like, define the problem, define the options. You know, like here are the 3 actual things that we're considering. Define who the input providers are. Let me pull someone, the right person from brand and from engineering and customer success because it touches all three of theirs. And then define the time bound and finally define a clear decision maker. And if you, I would say we've used that process and there's a little bit in it of people read through it, define the options, do a blind vote, then discuss it in a preset order. And then do a second vote. And the decision maker takes all of that and then makes a decision. Usually we require that decision to come either in the meeting or within 24 hours. Whereas going with defining those inputs, you're saying, I'm not going to collect all the information, I'm going to collect it from these exact people. And then the next is the definition of the options. Something that I do all the time, is just list out all the possible options, even the ones that I would never do. You know, and you're like, but that is an option that a rational person might choose to do it. You know, we're gonna raise a whole bunch of money. There's reasons I'm not gonna do that, but that is an option to achieve the goals. So I'll list it out. And then I can step back and be like, all right, all 7 of them are listed. Here's the 3 that I'm actually considering. And then I'm not like stuck on my 3 thinking, ah, is there a 4th? And then the clarity of who the decision maker is, uh, something that Brian Armstrong talks about is trying to push it down to the person closest to the problem. And that's also really freeing because I used to have this idea that, oh, the senior-most person needs to make the decision. There might be times, um, you know, that I'm like, I'm going to be the decision maker on this because of It's a one-way door, you know, and even if it doesn't work out, like, I don't want to put that pressure on the person who ultimately made a decision that didn't work. But in all of those things, you can end up with a very clear process and solve for speed, and you've heard everybody, and it's just completely different. And the only thing that I feel like I don't— in that, that I don't do well right now is identify when a decision is like you and I talking and going, "Yeah, sure, let's do this. Okay, cool." And we move on. That's like one end. And then the other is, "Okay, this is so important that it needs a formal process." And you can end up wasting a bunch of time in the middle where you actually spent a week or 3 swirling with more and more people and uncertainty and all of that. And when you should have just said, what we call it is saying, I am calling a DMF, meaning the decision-making framework. Anyone has the right in the company to say, I love that. I call this, you know, everyone's like, okay. And we immediately move into the formal process. Um, and so sometimes we wait too long to do that.

Uh, but you have a process. What's interesting in hearing you talk about what makes a, makes a decision the best You didn't say anything about the outcome.

No, you can't know the outcome. Right.

It's not—

Which past me would obsess over the outcome.

Right.

And how do you know? And how can you be certain?

Yes.

And so if you— that's kind of the, I guess, the paradox of it is that you have to let go of any attempt to grasp for certainty.

It's coming back to your relationship to uncertainty. But also putting a process in place and recognizing a process is manageable and repeatable. I mean, it's the Howard Marks line of, you can't tell the quality of a decision based on the outcome. Tell the quality of decision based on the process. And what I hear is you have developed a process. The process that you have today is very different from what 29-year-old Nathan Barry would've ever— Oh yeah.

Night and day.

But I guess one of the things that's really critical in all of that So there's the downstream, which is the process and the cultural pieces, the DMF. But then upstream of that is actually your confidence. And you started this whole thread around, well, I'm just much more confident.

Yeah.

But if you were to have 29-year-old Nathan walk in here and say, hey, be more confident.

He wouldn't do anything.

So what has changed for you? What has allowed you to be more confident? What has enabled that for you?

One of the first things is a lack of confidence comes from uncertainty, usually. So long as it's an aware— there's plenty of people who aren't confident because they totally lack awareness or who are overly confident because they completely lack awareness. But if we're trying to get awareness in here, and then that brings us somewhere on the confidence spectrum. One thing that really helped me was realizing the impact I was having on other people. A line that you say fairly often is one way or another, you'll ask some version of, is this serving you? This habit, this trait.

I was wondering what I was going to say. Yeah, I do say that. That does sound like me. Yeah.

And it's different because it's not good or bad.

Mm-hmm. Yep.

It's just, is it serving you? You know where you're trying to go and is that going to help you get there or not? And so realizing that the number of times my lack of confidence meant that I was going to everyone else to be like, help me make this decision, or really actually, please feel strongly enough about the correct path that you can make this decision for me. And then if you wouldn't mind convincing everybody else around the table that that's the right decision, that would make life way easier for me. So like abdicating my role as a leader and feeling like the outcome was binary of I could do that path where I listened to everybody and we negotiated and debated and all of that until we got to certainty or consensus. Or the other way is I could be a dictator and I could say, this is what we're doing. I'm the founder, I'm the CEO, this is what we're doing. And not realizing that there's like completely different paths. And both of those will like destroy— you know what? I thought that one was safe and the other wasn't. Being a dictator is not safe because then you're an asshole. You're, you know, people don't want to work in that environment, all that. But consensus building felt safe because, I mean, consensus is even a positive word, you know? Like, of course we want consensus. Why wouldn't we? And not realizing that it was incredibly harmful to the organization because we didn't make decisions. We continually undermined our own confidence and realizing that all everyone around the table wanted was for me to truly listen and then to make a clear decision or 100% delegate the authority to them in that decision and say, Your job is to truly listen and make this decision because you're in the best seat to do it. So I think the confidence comes from, or the change in uncertainty comes from a lot of reps, you know, just doing this many, many times and having a process and realizing that the consensus-based culture was actively harming rather than serving.

But it's interesting because I think what you expose there are some of the assumptions that you brought into this company. And those aren't— that's not necessarily how the world works. Those are how Nathan saw the world work. It's like, I am safe when I have consensus. I'm unsafe when I challenge other people. And that goes into how you related to conflict in the company, not just decision-making, but in general. But you always framed it as this spectrum of consensus building or dictator. And when you and I would have those conversations about dictator, there's a part of you that really wanted to be dictator, but that was not safe because it meant losing the people that you cared about being with you. So I would say that what I see too is the present-day you realizes that those assumptions actually are not appropriate for how you want to lead. And they may or may not be true anymore. And it sounds like you're more in the camp of the Brené Brown, clear is kind, unclear is unkind. I assume it's actually kinder to be more direct with folks and to even be in conflict with them at times.

When there's redefinitions of it, right?

Yes.

Growing up for me, conflict is scary.

Right.

Now conflict is healthy. The lack of conflict would make me kind of raise an eyebrow and go, "Oh, that's interesting." Huge red flag when working with folks. "We never have conflict. What are you talking about?" And you're like, "Huh. So what's unsaid?" It's that whole thing. And so yeah, it's a complete reframe.

And I've seen that shift. But so what I hear, I want to follow more of the threads, but Part of what has shifted your confidence is frankly just experience and knowing that you can make mistakes, you can engage in conflict and still be okay.

One quick thing on the experience is I don't do this actively now. It's a habit that I should probably return to, but for a period of time when I was just trying to optimize for decisions and velocity of decisions is I would just keep a decision log.

Oh, right. Yeah.

And just write down What decisions did I make? And I think for a period I actually had a decision quota where I was trying to hit 5 decisions a week that I could actually write down. And because I'm just trying to build that muscle. It's like going, if we're going to train for a race or something like that, maybe you're not making the whole plan. It's like, you've got to just at least get out and run to start. And so just saying, look, I'm going to build the muscle of making decisions. And then on important ones, I would write out things like, if this goes well, here's how I'll know. If this goes poorly, here's how I'll know. Like that would be a hiring decision or something like that. But yeah, like the log was helpful in that. How do you think about your relationship to uncertainty as a founder and just something that you see across the board with so many people that you coach?

Generally, it's a fascinating, complex topic. And there are common themes and then they're individual. So certainly at the individual level, how people may or may not define themselves on being right or not being wrong, what that meant for their love or safety or affection growing up, those add individual layers to it. But then in general, I find that especially for founders, they end up founders because they want to make the uncertain certain. They want to pursue an opportunity. They want to take an unknown and make it a known. They want to create something from scratch. So they have a natural belief in their ability to do that. But also with that comes, I'll say, an oversized sense of responsibility for both positive and negatives. I have lots of client founders who have an oversized sense of responsibility for only the negatives and discard the positives. So, you know, I will often tease them about it, but I have lots of people who will, all these good things are pure luck and all these bad things are my fault.

That's all on me.

It's all on me.

It's all on me. Is that something that I show up with?

No, actually I don't. I would say you have a pretty healthy balance of them, of responsibility. You don't deflect responsibility.

Yeah.

And you do claim, and I would say that if we think about how you've evolved since 29-year-old Nathan, I think you do claim more of the positive. You celebrate it more. You take responsibility for it more. I think you're good about distributing that as well, but I think you have a healthy balance in terms of your sense of responsibility for the positive and negative. But I see like the discomfort with uncertainty. Folks try to get rid of the anxious feelings with logic and analysis and preparation. And it's like, how do I get rid of this uncomfortable feeling by getting all the information I can? And to a degree, that's important and helpful, but in other ways, it's actually not serving you. And I can go into that more, but—

Yeah. I think that's really interesting of, I mean, just going back to that question always of identifying the habits and the traits and how you show up and saying, is this serving you or not? I think something also that you've helped me with a lot is not trying to fix everything at once. We'll choose something that we kind of hone in on. Decision-making was the thing for a while. A phrase you would use is, take your seat as a leader, right? And so say like it is actually your role and responsibility. And so we'd spend 6 months or more, you know, where that is the central thread, um, rather than trying to dive into all these different things at the same time.

Well, uh, the take your seat as a leader, it's a critical component that I feel like I see almost every client struggle with to some degree. And there's a bunch of reasons why that's the case, but—

Maybe explain really quick what taking your seat as leader means.

It's to claim your right and authority as the CEO, if that's your role as your CEO in the company, to define what you're doing, to make a clear decision, to take action, to know that you can say, this is what we're doing, even if everyone else disagrees. It's really about claiming authority, I think, is how I would frame it.

Before we worked together, I would see as a negative thing of like, oh, you think that you're better than the rest of us and your opinion matters more and all of that. I can think of a specific moment where we were having a board meeting and executive meeting. It was virtual and our previous conversations had gone very, very poorly. And so we brought in you and Andy from Reboot to facilitate it. And there's lots of times that you let us, you're like, "All right, let's see where this goes." You'd ask kind of the right questions and then you'd step back, all of those things. And that take your seat as a leader was the thing that we were talking through and working through the most. And I remember being on a recap call maybe immediately afterwards, I don't know. And this is at a time where we were just not functioning as a leadership team of this company. And you can see it in the growth numbers that were around that time and everything else. I don't even remember what the decision was, but I said, this is what we should do and here's why. And I stepped in. And the thing that you were reflecting back to me afterwards was like, did you notice what happened? And it was in a Zoom room, so you could still feel the energy though. Everyone settled and everyone was like, okay, that's clear. And like me being able to see with like your reflection back that even the people who I would say like didn't get their way, I made a decision that was against what they thought was best. They ultimately got their way because the decision happened and it was clear and they said, okay, I can bring that to life. And just watching the entire room change was like a huge turning point for me.

[Speaker:NATHAN_BARRY] I remember that. I'm glad you brought that moment up because I was going to bring that up too. I remember that very clearly. I mean, it comes back to the Brené Brown quote, clear is kind and unclear is unkind. I mean, even if I disagree with what you've decided, the decisiveness and the clarity is helpful for me. Now I understand where things are. Now I understand what the rules are, what we're doing. But do you remember that? Do you remember how it felt when you made that decision? I mean, we don't remember the specifics, but I remember that moment. I wonder if you do.

I mean, it felt relieving. Calming. And I noticed some of it in that moment. In that moment, my fear was like, "Oh, that worked. Okay." And my fear was that then people said like, "Okay, well, I guess." Maybe they were dismissive of like, "All right, well, at least Nathan made a decision," or that sort of thing. In the conversation, your reflection back afterwards and the conversation with other people afterwards that they were there wasn't a negative, like, your way or the highway, but at least, you know, we have a path. It was very much a thank you for the clarity. And like genuinely, because I think in human relationships, that's what so many people want, right? Like in, not to equate running a company with raising kids, because they're very different in many ways. They're similar in other ways, you know, but kids are always asking, like, is this okay? Is this— where are the boundaries? What are their constraints? And most, many disasters in parenting come from when they are not— when those boundaries are nonexistent, unclear, or worst of all, shifting. And realizing like, oh, I just, I provided clarity and everyone can be like, all right, we'll get on board with that.

And that's literally taking your seat. That's what taking your seat is. And I remember that moment. I remember, and it was Zoom, like you said, but seeing all those faces, and you could feel the frenetic energy around, like, and you could almost hear people thinking, somebody make a decision. And then you made it, and then you felt the energy drop, like in a settled way. Just like setting a boundary with your kids, you know, even though they may not outwardly like the boundary, you can kind of feel them drop into the safety of the boundary. And I saw you do that. I mean, that was— but think about all the assumptions that you held prior. Think the rules you had around people and being in relationship with people prior to that moment.

Yeah. And I thought I'd be creating more conflict in, you know, and showing up as someone that I didn't want to be if I made a decision in that way. And it turns out the opposite was true.

Well, that kind of goes back to if we think back on the ways in which you're different than the 29-year-old Nathan. I mean, I remember having extensive conversations around that spectrum of consensus-driven versus dictator. It's like you kind of saw it as one of those two options. So what do you know about that? How has your understanding of that evolved?

Well, I think one big shift is I used to define everything on a binary spectrum like that. And I think the world wants to, whether it's politics, are you on the right or on the left? Or in companies, are you building for growth or for profit? Are you consensus-based or are you a dictator? And really almost nothing exists on a single axis. I wrote a blog post a while ago or newsletter called The Single Axis Fallacy. And so I think a big shift is that I try on multiple other axes in my graph. And so if it is consensus-based or dictator, you know, I'm like, okay, what if those were separate axes? What would that look like? And then it's like, okay, maybe it is one is all about how much do you listen and truly hear and understand? And then maybe the other one is all about the clarity of the decision. And so if you don't— or the decisiveness. If you don't listen and you make very crisp, clear decisions, then like, yeah, you are all the way in the dictator quadrant. Right? And if you listen deeply and refuse to make a decision, then like you're in the worst consensus-based. But we've taken this binary thing and turned it into quadrants and these two axes, and you can see, okay, where do I live in this area of decisions or this area of my life, and how do I want that to change over time?

I've seen you do that effectively too. You have such a care, and it's at the center of the business, such a care for people. But there was an assumption that I care for people by listening to what they say. Or I do what they want me to do versus hearing them, but then still acting on it. I mean, we've talked a little bit about how you have changed from the 29-year-old Nathan. I think one of the things I have seen not change is the why you're doing this.

I think it's been—

I think you've added to it. I think it's evolved a bit, but I think at the core it has stayed true and stayed the same. I'm wondering if you remember this. I mean, early in our work together, And this is part of how I like to work with clients is really understand why are you doing this? Not just because I'm curious, though I am, but also because I, what I've learned is that really being deeply connected to our why and thinking of the Nietzsche quote, um, he who has a why to live for can endure almost any how. I probably butchered it, but the point being really being deeply connected to the why serves as this foundation to address any how, any challenge. And Suddenly the existential challenges, the challenges of the moment become a thing that we can get through and move through and learn from and move closer to our why. So I remember early in our conversation really exploring the why. Do you remember that? Do you remember that conversation?

Yeah. I mean, it was something that came up a lot of not just what I wanted to do, but how I wanted to get there and everything else. And so for me, there were so many aspects, like at the surface level, The why was I wanted to earn a living so that I wouldn't be a burden on other people, so that I could take care of my family and all that in ways that I didn't see my parents being able to do. And I was avoiding the level of conflict that I saw come from a lack of money, a lack of resources and all of that. And then it evolved over time where I realized Probably in 2012, 2013, around the time that I started the company, I felt like I had discovered the cheat code to all of this where it was building an audience. At this point, we make tens of thousands of dollars on the internet from people that you've never met before. And I was like, do you all know this? This is incredible. The only other time I felt like that is when you I discovered, uh, like travel hacking and using credit cards to fly for free where you feel like, why isn't everyone doing it? You know, it's like this amazing thing that's available because people say like there is no cheat code, which on one hand I agree with, but then you discover these things that are just like very, very powerful. And so really so much of my writing and the work building the company around that time was about How do I show other people that this path is possible? And it's continued to evolve from there. You know, now it's in the, like, how do I build those tools? And that's why Kit has always had this blend of tools and training, and that's a lot of why this podcast exists and so much else. But like, yeah, where in that did you want to go? That's the overarching.

Why is that particular mission so compelling to you?

Oh, yeah. Yeah. So we got to this through many coaching sessions. And something that you do a lot of is you play with time, right? And so jump back, what would you say to you at this age? What's the difference between here and there? Jumping forward, the times that you've done this, it's given perspective, like on decision-making. Of I'm stressing about this decision so much. And then you'll jump forward in time and you'll be like, does this decision matter? And you're like, oh, in 3 years from now, are you going to be like, was that the right— and 9 times out of 10, it's like, no. Okay, so let me approach it with the right amount of weight. But one that you did was really talking to the 13 or 14-year-old version of me, really watching like feeling stuck and feeling like a burden on my family and all of that. And so the why for me was going back to that person and saying like, you can do it. And there's a clear path that you can follow. Like, not only am I confident in you to be able to do this, but there's a way, like when you understand these things about how the world works, it'll change everything. Think about the book that I'm writing right now, The Ladders of Wealth, is trying to answer that same thing for that 13-year-old version of me who just feels completely stuck. And it's like, I don't know how this works. I feel like, how do you make money? How do you keep the money? Is it the job that you have, the career? Do I need to become a doctor and go to school for 8 years and all of that? And what I'm trying to do is the equivalent of give someone a diagram for powered flight, like the shape of an airfoil for a wing. That's one of those things that before that was known, this is impossible. Once that is known, like a coworker of mine at a past company had this somewhat facetious single-page tiny print document that sat in his cubicle. And it was basically like if the world fell apart or if I went back 100 years in time, this is everything that you need to know. And it's like germ theory and how wings are designed, you know, all of these things that once they are known, it changes everything. And so I feel like a very, very strong— I feel a calling to lay out that path and make sure that those things are known. Because I see myself and so many other people just feeling like you can't get out of this and you just, you know, you will never be enough. You'll always be a burden on other people. You won't be able to be in control of your circumstances or it'll take decades. And I just want to be like, oh, like slide the paper across the table and say, this is This is the framework. This is the physics of money and audience and all of these things. And once you understand it, like, your entire future is in your control.

So what is it that you most want the 13-year-old to know?

Well, that he's capable, safe, and there's a clear path.

Do you feel it right now?

Oh, yeah. Yeah. And, and then ultimately that regardless of what he feels about how he relates to other people or any of that, that he has value, like intrinsic value. And that you can create from that place, not from the place of like, how do I not be a burden on other people? And I think that's, you know, if you go to the Enneagram, right? So much of a 3 in the Enneagram is this like, like the deep longing is like to be loved and valued truly for who I am.

Yeah.

Right. With everything else stripped away. Which is ironic because the outward side of the 3, you know, you're like, how do I achieve the absolute most, be as valuable to as many people as possible? And then the thing that I want more than anything in the world is for none of that to matter and you to just love me.

I get it as another 3. Yes. I totally get it. Speaking of playing with time, I mean, let's bring the 13-year-old in. Like, what would he think of the Nathan who's here today?

Oh, he'd think it's ridiculous. Like, I mean, we're talking about this as like kind of a milestone episode. The 13-year-old would be like, oh, if you could make like $50,000 a year, that would be incredible. And I'm more like, no, go add a handful of zeros to that. Let's go tack 3 more zeros on the end and it's over 50 million now. I think that that's wild. 13-year-old me loved woodshop and tools and understood that tools were necessary for creation. And there's so many times that I'd be like, oh man, if I only had this thing. Like a friend of my dad's had a scroll saw, which is for cutting very fine, intricate things in woodworking. And he saw how much— he bought it for a certain project. He did that project and he saw, like, I came over and borrowed it like 3 times and, or used it at his house. And he saw how much I loved that and he gave it to me. And like, that enabled me to do so many different things. And so I knew the importance of tools. And so, oh man, I'm going to choke up on this. 13-year-old me would walk into the studio Not— he'd be impressed with my studio, the room we're recording in now.

I'm quite impressed with your studio. Yeah.

But he'd be more impressed with the other 4 studios that are open, like the tools for everybody else. And so it would be all about equipping people with the tools and the training to create whatever they dream up. And so I think, yeah, he'd be most impressed with the impact.

One of the things that I see consistently with clients, driven high achievers, is that they're constantly looking ahead. Yeah, we're $50 million, but I need to get to $60 million. I need to get to $100 million.

How'd you think that?

But the thing that we can do by inviting the 13-year-old in is it actually helps us see where we are right now. And to really feel the impact, feel the meaning, feel the achievement. And to celebrate the moment we're in versus where we're trying to go. But that's a constant challenge, constant challenge. And the irony is like not looking at where we are now, we constantly feel behind. Which puts us in this space of, I got to do more, I got to do more, I got to do more, I got to do more, which actually makes us more indecisive, makes us less confident. But the 13-year-old, I mean, I just, I really appreciate that moment. I don't even care about the cameras. Like, just as your friend and partner for a long time, I remember the 13-year-old and I know he's there on a lot of our conversations, but it was really great to hear, have him come in here and help you see that too.

Yeah.

Especially on a milestone episode, if you will.

Yeah. It's, something that I have to keep reminding myself to come back to and surrounding myself with people who will help me come back to that point of just like, why are we doing this? I have a lot of people in my life and work who I've been with for a very long time. So like Elizabeth, who has been my executive assistant for a very long time and now has moved into other roles inside of Kit. She is always— the conversation we just had a few weeks ago, was how do we recenter the team on the mission? She's like, "Hey, this presentation that you gave 3 years ago, there's now like 50 people in this company that have not seen that. It's time to give that again." And it's just, it's such an important thing. I guess we're talking about playing with time again, right? To cut through, did we grow faster than we expected? Not as fast. The conflict that we had, the individual decisions, And to just continually recenter on that, all of that on why do we do what we do? It was even something I realized, I don't think I do enough of this at Kit, even though I think we do a lot more of it than many other companies. But I was listening to David Senra on The Founders Podcast talk about James Dyson and making this vacuum cleaner that doesn't use a peg and it's totally different. And They're all made by huge companies and his is weird and sits on the edge. And he came back to storytelling where he got all of his, all the stores that carried his vacuum cleaner to put a tag on the vacuum cleaner that told his story and why he invented that and like what they were trying to do, what that means and everything. And because that was the differentiator. And I realized that Yes, I might talk about it on a podcast sometimes or in front of the team at a company retreat, but I don't have the tag hanging on every product to let people buy into the mission of why we're doing what we're doing. Because past me would think, "Oh, if I did that, that would be about me. That would be me saying, 'Oh, I'm the most important person. If you're going to come be a customer of ours, you should understand me and my story and you should buy because of me and all of that. Now what I've realized is what I'd be doing in telling that story of 13-year-old me is that I would either be giving them something that they could relate to and they could say, "I want to help other people do that. I want to be part of a company that thinks in that way. And I understand the importance of financial freedom and laying out this path, and I want to be a part of that in some way." Or they would see themselves in it. It would speak to the version of them, you know, the 13-year-old or whatever age that's inside of them right now. In either way, it would help take education and software and these surface-level things and you give it real meaning. And so then not only for myself and for our team, but also for our customers and everyone else who wants to be a part of this, they've realized we're doing something that really, really matters.

I appreciate it. I didn't mean to take you there. But I feel that, you know, and lost in all this. And I know normally there's, there's frameworks and all that, all the things we could teach, all the things you could teach. But the power in the why. It's an unstoppable force. It's a force that connects to people at a very deep level. And like you said, some people are going to see themselves in that and like, I have to be with this. I have to be part of this. But we avoid the feeling. The feeling is scary. We avoid the feeling. And the feeling is actually really where the energy is. Like, think about how you feel about your work, your team now, right now.

Oh yeah.

I can see it. I can feel it. Yeah.

And it's just the idea of like what you're doing matters. And for me to be able to translate that through every aspect of what we do. You know, the other thing, the other area where I feel really privileged to work in this business and especially this industry is that every person that we serve is impacting so many more at scale. Right? We, in our email marketing product, it's like, do you have 1,000 people on your list or 10,000 or 100,000 or whatever? And almost always all of those people are on that list because you as the creator are delivering some value to them. Speaking into their life, their business, their soul in some way that provides meaning. And so, you know, people talk about when is the right time to sell a company or keep going or whatever else. And I just feel insanely privileged to have ended up, whether through decisions or luck or the combination of all that, in an industry that was really about impact. And that could be the kind of impact that we're having or a customer like Nisha Vora, who has this incredible vegan food content and she's helping people live out their ideal lifestyle and showing them how to do it all the way through to all the authors that we know and love who are writing books that transform people's lives to the YouTubers, to the podcasters and everything else. And yeah, I think as we just, as we wrap up this, this, uh, little 50 million celebration episode, the things that stand out to me the most are always recenter on why and make sure to tell the story of the impact all the way through.

That's amazing. I agree. I guess I can't help but ask, what would the Nathan in 2035 What would you like him to see and say as you celebrate whatever that milestone may be?

10 years from now?

Yeah. We know it won't change, the why.

The why won't change. And it's evolved.

It's evolved, of course.

But it's really, as people have built much more valuable businesses in this space, it went from, we want to help you just earn a living to now, we want to help you have build a valuable business around this reach and impact.

And less of the what and more of the who. How might you be different, if at all? How is Nathan showing up differently in 10 years?

I think there's so many things that would be the same of—

That's okay too.

Continually looking at the journey that I want to go on, who I want to do it with, and who I have to become to achieve that, to achieve the ultimate goal. I think there's going to be something that will change, probably over 10 years is maybe the direct involvement. I think it's going to be— so much of what I've done early on was the impact that I can have, and there's still a lot of that. But I think something that I really want to be celebrating in 2035 is the impact through other people. And so I think it'll switch to I did this, we did this, that we're celebrating. And then others use that, those tools, those training and everything to go on and do these other things. But really, so like looking around at each of the individuals in the company or everyone else, and it's just 100% you did this. And like celebrating that, that part of it.

A leader is best too when the work is done, the people will say we did this ourselves.

Yeah.

Yes.

I think that's true.

Beautiful. Yeah.

Dan, when I asked you to be on the show, I probably should have known that I would cry. Uh, the last 8 years that we've— 7, 8 years that we've known each other, worked together have been very, very powerful for me. And so it's been a lot of fun to go through those lessons learned and recap the journey. But I think there's so much more of it that I didn't even expect, like the levels that we would, would go to. And so I'm very, very grateful for, uh, our friendship and relationship over this period of time and you coming on and helping me celebrate and then just share so many of these things that we've been able to. So I'll let you answer that. And then I want to know where, where people should go to check out anything about you, get in touch with you, any of those things.

I just want to say thank you and the privilege to not only be here, but to be partner, friend on the journey with you, to know the impact you're having every day with your team and your customers and to be a small part of supporting you is, it's my why. Yeah. So thank you. Thank you for the work that you do. And the, the, the work of looking within is scary and hard, but it's so critical if you're going to be a leader. Builder. So thank you for doing that. Um, Reboot, reboot.io, company I co-founded. Uh, I have a somewhat dormant website, danputt.com, um, and a dormant Twitter account or X account. But, uh, just Dan at Reboot is probably the easiest way to reach me if folks want to reach me.

That sounds good. Thank you so much for coming on.

Thank you. Thanks for having me.

If you like this episode, be sure to like the video and subscribe on YouTube. Because we actually have another episode with Dan Putt coming out in a few weeks where we get his unique approach to coaching. In it, he shares practical tools you can start using right now, even if you're not working with a coach. Leave a comment with your thoughts on this episode, and I'll see you next week.