Million Dollar Coach: What It Takes To Be A Great Leader

This is far more important than any pricing strategy we can map out on a board or any tactic.

Absolutely.

Behind the scenes at some of the most successful startups you've heard of, there's often a coach in the room, someone helping the founder think clearly when things feel messy. That person for me is my coach, Dan Putt. So something that you've helped me a lot and probably helped hundreds of other leaders with is this reframe of from conflict being a bad thing to conflict being a good thing. So can you talk about that?

Yeah.

He's one of the founders of Reboot, and he's spent years working with leaders and executives who are trying to grow without losing themselves in the process.

We often will throw around these terms like be successful or be effective that don't really mean anything, right? Like I hear all the time, I just want to be successful. What does that even mean? You don't sit in your car, pull up Google Maps and say like somewhere.

Dan also shares a number of specific tools you can use even if you're not working with a coach.

I don't get into my email inbox until after I have journaled. For a long time, I did The Artist's Way. Are you familiar with No, I'm not. It's—

Wow. They've definitely helped me navigate conflict, make hard decisions, and do it with confidence. And I think they're going to help you get clarity as well.

There's a right way, there's a wrong way, there's a way that works. And what I find to be the most important and most powerful for leaders is— I like that.

Dan, welcome to the show.

Thanks for having me.

So we have worked together for 7+ years in various capacities as you've coached me in building Kit, like tripling revenue, more, more than tripling revenue over that period of time. And there's another episode where we'll dive into my story and that journey and everything else. But what I want to do is take advantage of the seat that you have of talking to all of these incredible leaders across a huge range of companies, like from dozens to thousands of employees. And you really get to spend all this time with the founders and see those common trends, the places that they get stuck, and a lot of the common tools that you're able to give them. And I thought it'd be great if we could dive into some of those today.

Okay. I'm not usually the one being asked questions, but—

You like to ask the questions.

I like to ask the questions.

Yes. That's the first thing is that the most likely thing is that at some point you'll turn it around and start asking me questions. I will. Yes. That's a good place to start. Because that comes down to your approach to coaching. So maybe we'll get into that in a sec. Actually, let's go there now. Your approach to coaching. There's a lot of different forms of coaching, very broad thing. How do you think about it? What do you think is most effective for you?

Yeah, there, uh, this has been an answer that I've developed over the years of, I think at this point, I don't know, thousands of conversations with people looking for a coach. And I wouldn't profess to say that we have meaning my company Reboot or me, we have the right one, but we have what feels like it works for us. And so I think about coaching as living on a spectrum. You know, on one end of the spectrum, what could be called coaching may look like, or I might call more like advising or mentoring. It's much more directed. It's where somebody is giving you a clear point of view, maybe even a framework, and saying, hey Nathan, this is what you do here, or this is how you do X, Y, and Z. Really useful, really helpful, really important. So that's one end. The other end of the spectrum may look more like therapy, which is really looking within, trying to understand you, your story, what drives you, what are the assumptions you hold, what are your mental models, et cetera. And so where, where I live and where, where my company Reboot lives is sort of like closer to the therapy side, not because we're therapists, because we're not, but because where we have found we can get the most impact and help our clients make the most change is first to understand how they operate. What are their mental models? What are their blockers? What are their assumptions? What's their why? And to really understand that then actually helps us understand, well, what are some appropriate frameworks that may actually help them take action? But even more importantly, it's driving them to an outcome that they own. That's from a deep understanding of who they are and what matters to them.

Rather than—

Rather than—

Here's a tool that will get me through. This situation that's right in front of me.

And again, there's a time and a place for that, and that stuff is quite helpful, and there's a whole world of content out there around that that I believe in. It's not my style, but that's, it's important. I think honestly, if you're a founder or a leader, you should probably have something across the whole spectrum. I think it's useful.

And that's actually the way that I've thought about it is I have people that I go to for like, okay, I have a tactical problem in front of me. I'm just looking, I'm trying to decide between 3 options and I want your expertise and reflect back some clarity and let's make a decision. I go to my board of advisors for that, go to friends, that sort of thing. Then usually what you and I are talking about is much more, much bigger things where it might start in a simpler problem, right? Which should we decide A or B? But then digging layers deeper and saying, okay, why? Why is this even the question that we're asking? Why are we here? What are we ultimately solving for? And going more existential and all that. There are times where I'm like, Dan, just tell me what you think. And thankfully what I appreciate is when I say like, no, I want you to just tell me what you think in this, you're like, okay, fine. And there are times where I can get you to do that. But most of the time you'll tell me something and then like, ask an even better question that, that goes much deeper.

Yeah, I— especially with, you know, when I've had a chance to really get to know the client and we've spent a lot of time together, um, I, I can have an understanding when there's a greater opportunity for you to lean in and really grow as a person. And, um, there's a saying we all throw around at Reboot, which is using work to do your work. What that means is ultimately using the work to better understand yourself.

Right.

What drives you. So when we're working through a problem and I see an opportunity for you to actually work on something, maybe a pattern or a mental model that you've been stuck on, that's where I'll go and focus. That's where I'll typically answer your question with a question.

Yeah.

But sometimes you just need some help. You just need a reflection. You just need some clarity. And usually when I give you those answers, it's not just from my opinion. It's more of an understanding of you and what drives you. Sometimes I'll give you my opinion, but usually I'm not doing that.

I usually have to ask for it very directly.

That's right. Yes, yes, you do.

Yes.

And sometimes it's appropriate just to give the answer or sometimes it's helpful just to be a reflection.

Yeah. If we were to run through, I don't know, maybe through the course of the episode we could do 4 or 5 of some of the biggest sticking points that you see leaders go through. And those might be, we can use stories of what I've encountered, you know, or more broadly, you know, we'll use some anonymous client examples or things like that. But what, like, what's one of the big sticking points that you see as a theme across all of these founders who are trying to scale a business?

Well, I think one that you and I've talked about for you is this, this hesitation to take your seat, which is to say, claim your authority as the founder and CEO in your case, to be clear and decisive, you know, and those are, those are related. They're not the same, but it's really to recognize your authority as a leader of the business.

Right.

I see so much hesitation around that because they don't want to upset people or they're not comfortable with what the answer is. Like, what is the right answer? And being decisive is hard if I'm not certain. But yeah, I would say that that is a big one where folks— who am I? They'll hold back and say, who am I to make this call? Or who am I to know what the right thing to do is?

Yeah. Does that get into the imposter syndrome? Side of it?

Yeah, yeah, exactly. That's right. Imposter syndrome is a very big one. There's this, this, um, I guess they're similar, but they're not exactly the same. But there's this struggle around, uh, like believing that someone else out there has all the answers, knows all the right things to do. I used to joke about it with a client who called it the Greek god CEO. It's like he's out there, he would know exactly what to do if he were in my seat. And the fact that he exists and I don't know the answers makes me feel terrible.

Right.

And there's almost this suffering that I see clients go through is like, I know that I'm doing it wrong. I know that somebody else would be doing it right and I'm doing it wrong, which by the way, takes you away from your ability to actually solve the problem in front of you. Right. And I would say that's actually a very common thing I see, particularly with founders, although I see it with leaders in general, but making meaning of the problems in front of me. So what I mean by that is like, there's a problem in front of me and I look at it and say, this is proof that I'm terrible, or this is proof that I suck.

Someone who is more experienced, someone who didn't suck in the ways that I do wouldn't have this problem.

Would know exactly what to do with this. And the funny thing is that actually takes us further away from our problem-solving capabilities. And in most cases, a founder Or someone in a leadership position is there because they're good at solving problems and they enjoy solving problems. But when it becomes proof of their value as a human being, it feels so heavy and scary that they want to hide from it or run from it or suffer facing it. And so just helping them see that, that comes back to the mental models, helping them understand that, um, I am making my, I'm defining my sense of worth because this problem exists. When the truth is that if you don't have problems as a founder, then you're out of business. There's no business without problems. So if we can stop defining ourselves based on the fact that there are problems and recognizing, as one of my clients said to me once, the problems are the privilege of being a founder. And he actually had a coffee mug. I don't know if I could curse on air.

Go for it.

He had a coffee mug that said, stress is caused by giving a fuck. Like the stress around solving these problems reminds me that I care. And so if I can just separate the meaning I'm making of myself and recognize even the privilege of like, oh, here's another thing to solve. And I'm here because I like solving problems. Then I actually come back online and I can solve the problem.

I think a framing that you've given me at some point or that we've talked through is like the have to versus get to. And going through, I have to do this and I have to do that. And then realizing that you get to, like, so many of the problems that are in front of you are a result of the success and the privilege and everything else, right? Like, you would not have this struggle to recruit a key executive and trying to figure out how do I convince them to join the company and all of this. If you were, you know, at $100,000 in annual revenue, right? But because you're at $10 million in annual revenue, right, like you have, you know, you're like, okay, how do I design a comp plan that retains these people? And it's a hard problem, but you get to solve it as a result.

Yep.

I think another one is really— well, actually, let's stay on that, on, on that for a second. Are there other questions or tools that you use related to imposter syndrome or people really struggling with what the problems in front of them say about their identity?

I think is, you know, in all of my work, it is leaning into some curiosity. And so one thing I might check in with somebody there is asking them what assumptions they might be holding about this particular problem. And that includes what are the assumptions I'm holding about me and my ability to solve it? Because so there's so many things that are running on autopilot for us. So I'm trying to think of a good example, but I'm not coming up with one off the top of my head.

Yeah, but that's fine. One thing that I noticed you doing a lot, and this is probably defining, like a defining trait of both your life and how you coach, is you've, or I've heard you say it as listening to understand instead of listening to respond.

Yes.

I've listened to respond. Like that is my default mode of like, okay, I know where you're going, here's what I'm going to say. Perfect. And then we'll have a free-flowing conversation. But the thing that I see you doing continually is this, like, listening to understand. And that's why I think the question— you know, asking a question is your most default response. You gave me 70% of what I need to understand and let me fill in the gaps. But how do you think about that?

How do I think about listening to respond versus listening to understand? Well, there's layers to that question. I mean, there's specifics to me and where, you know, some of the assumptions I held would be from my upbringing and my experience was like to not be seen was safer. So it's better for me to reflect, to turn it back to you. So there's, that's a pattern. And this is what I see all the time with founders. Like there's a pattern I developed that has become a strength, but when it's the default, when it's what I do with my entire life, it becomes a weakness. Actually, I see that all the time with, particularly with founders, is we learn some rules around how to engage with others, whether it's really good at solving problems or really good at asking questions. It becomes a real strength of ours in how we relate to others. But then when we do it all the time, it becomes a weakness. And so the opportunity, and I'm veering off of your question, but the opportunity is to first to come to fully understand it. Where did it come from? What drove that? Which then allows me to choose when I'm employing that tool versus not. This has evolved too in my work as a coach. And for a long time, I would get fixated on the ideas being offered. And what I have learned over time is actually paying more attention to the feelings that are evoked. And sometimes that's even just an intuitive sense, like images that come to mind as you're speaking. And then what I find is the best questions come from that place versus if I follow the thread of your words and I just stay with like the ideas, then we never actually get to the deeper opportunity, the deeper ideas, the deeper solutions. So when I'm listening to someone talk, I'm trying to pay attention to what I'm feeling as they're speaking. I know this is maybe a little bit inside baseball coaching-wise, but It helps me bring forth more curiosity into the whole experience, not just the ideas, the words.

When something that I experience being coached in that style is that you will notice even the little bit of a, like, emotional change or something else. And often I ask a question, like, I'll say something, and then you often sit with that for a second and then go, What did that feel like?

Yeah.

What are you feeling there? I'm like, nothing. Okay. You know?

Yeah.

And there's like, because I'm like, what? I didn't, I didn't notice anything, you know? And, but usually there is something there. Yeah.

And it honestly, it's still hard for me to do that in my coaching because I want to fixate on the words and let's call it the intellectual level. But the emotional level tends to be where there's the real wisdom, both about what matters, what's at stake. It also tends to unlock new ideas and frankly, open up the creativity, right? In profound ways. And I have to constantly remind myself of that, honestly, because it feels safer and easier to like, let's just talk about those ideas. Let's just get lost in those versus what's underneath that. What are we feeling here?

So this is— someone might be listening right now and be like, wait a second, this is completely different than what I expected business or executive coaching to be like.

Right.

You know what you're expecting? A conversation like, oh, we have this competitor who's just made this strategic move. What should we do? And that's not the area where you're playing in. You'll probably get to that point, but you have a phrase or a way of describing that I've heard of inside out leadership development? Like, what does that mean?

Well, going back to your generic example there, like, this is our competitor, what should be our move? What's the strategy behind that? That asking that question and expecting me to answer it implies that there's a right answer that exists out here that I can answer for you. And I don't believe that to be true. As my mentor, Jerry, says, there's a right way, there's a wrong way, there's a way that works. And what I find to be the most important and most powerful for leaders is to find the way that works for them, which is unique to who they are, what they care about, what their why is, what their mission is, what they're moving towards. You need to ground yourself in all of that information. And a lot of times the client is sitting there and they're not even thinking about that stuff or they're not connecting to that stuff. They're just so scared about making the wrong choice that may put them out of business or whatever it may be. So grounding them in really who they are, what they're for, something I often reference, then helps us access the wisdom on what is the right path for them, what's the way that works for them. And I've seen over the long haul that that tends to lead to better outcomes for founders and for leaders is finding my way, not the way.

Yeah, because I mean, this is something that transparently I've dealt with a lot, right? Like the email marketing space has been incredibly competitive. Well before I joined it with Mailchimp and Constant Contact and everyone else. They've been slugging it out for multiple decades and that's a very big space. So how do you navigate within that? And then the creator space the last 4 years or so has become very, very competitive between Substack and Flodesk and BeHive and us and others. And so it's very tempting to see it all as moves on the chessboard. If They do this, we do that, here's how it all works. And that really emphasizes the tactics. You know, there is a correct move. If we run with the chess example, in a particular combat, if you do a certain opening, there is a correct set of moves to respond to it. There might be 3 different sets of correct ones, but like mathematically, here's why this one is better than that one. And et cetera. And life in business doesn't operate that way because, I mean, for so many reasons. One, because people are involved. And then I think two, because the time horizon is just completely different. Yeah. So something that you've really coached me on is responding in the way that is right for us, which usually is not responding at all. And it's just following our own path. Doing our own thing. And I have watched probably at least 5 major competitors who over time, at some point I believed were the single biggest, most direct competitor to Kit exit the market or become irrelevant either through an acquisition or not getting another funding round or whatever else. And so with that ability to look back and see the trail of these, and say like, no, where are you going? What are you doing? It really gives that confidence to say, oh yeah, if I were to jump to what this person is doing and respond to that and then come over here to that, right? The whiplash for yourself, for the team, your customers, like it's very extreme.

Mm-hmm.

And so I think for me, that's such a clear example of instead of focusing on what is the tactic, what is the best decision in this moment? It's like, okay, what is most authentic to who you are, why you're doing things and the type of company that you want to build.

Right. There, there is a whole library of tactics you could employ at any given point in time. The question is, what is the right one for you? Not for just for who you are, but who you're becoming and what you're here to do. Uh, and you know, I, I see lots of people get stuck on that and coming back to the feeling, part of the reason why we do that is we're uncomfortable with than not knowing. And I just want to take action to not feel the discomfort of, you know, competitors or the uncertainty. But if we can first acknowledge, I mean, it's, yeah, to feel the feeling and then come back to, okay, what am I here to do? Why are we doing this? What is my approach? I see a very similar thing with individual leadership styles. You know, I used to, I used to, I've been doing this for a long time. I used to have people coming in and saying like, I want to be like Jeff Bezos. And then eventually it was Elon Musk.

Right.

I don't know who the example is now, honestly, but I used to get that specific question. Like, I want to be more like Elon Musk. How do I do that? And if you think about the question, like, first of all, what are some of the assumptions that somebody who asked that question might hold about themselves?

Uh, well, I mean, first it's not even about themselves, but if they were more like that, they would achieve more of their goals.

Right. Exactly. Yeah. And you can hear the anxiousness in the uncertainty. I don't know what the right answer is. Elon is successful. He knows the right answers.

Right.

How do I be like him? What I would always tell people is, but if I got you an exact checklist down to the minute on what he does and you did that, how would it feel? The answer was always terrible.

Right.

And then how would the company do? Like, well, I don't know. I don't think it'd do very well. Like, right. Elon is Elon. Elon's doing his thing. God bless him, you know, and it's worked for him.

Right.

But you're not Elon, and that's good and bad. I mean, you are who you are. So how do we find the way for you? That might include things, by the way, that's on Elon's list, but it may include other things that are specific to you and how you grew up and what matters to you. And the more grounded you are in that, the more clear, you know, the moments of uncertainty become. But even more importantly, I think it's, it's, uh, this is a marathon. It's not a sprint and trying to be Elon day in and day out is exhausting.

Yeah.

But so why not use this as a chance to fully become Nathan Barry?

Something that you do a lot is journaling.

I do.

You're a huge advocate for that. I was going to ask you how, like one of the key tools and how to understand how, you know, how to fully become yourself. And I think that journaling would be a pretty key part of that. Right.

Yeah, I, I'm biased here, but I'm a huge fan of journaling. I'm a huge fan of journaling and, you know, people kind of know that it's helpful and you don't have to do it every day like I do. That's, that's how my approach, but I think even just doing it around big problems, let me just lay out what's top of mind. For a long time, I did The Artist's Way journaling exercise. Are you familiar with that?

No, I'm not.

It's a book by Julia Cameron. It came out a long time ago, but she talks about starting your day with 3 single-spaced pages, handwritten.

Oh, wow. Okay. That's a big commitment.

And you have to do all of it. It would, by the way, it works out to about 750 words.

Okay.

There was a website I used for a long time called 750words.com. And I prefer to type it over writing, but that would be, that's breaking the rules, I think.

Yeah.

But what happens is you sit down with that. If you really follow that process, the first 500 words is just like, you can dump all the thoughts you have. But then when you get to the last 250, it tends to bring up the subconscious, the stuff that's really operating behind the scenes and the stuff that probably has more impact on you than you would want to admit. And actually then getting it on paper helps you get more clarity. But in general, what I find is, um, it sounds a little bit self-indulgent, but having that time to journal for me in the morning is like sitting down and having a cup of coffee and like really checking in. How am I doing? What's going on? What's top of mind? And that allows me to be more present and more clear. So, but I'm a big fan of doing that for leaders, whether it's just for specific problems or if it's for introspection or both. I didn't send it to you, but I used to send an article around from HBR that says you want to be a better leader, journal. And just having that place to process your thoughts tends to help you be more clear. More confident.

What are, like in The Artist's Way or in these journals, what prompts do you have? Is it just what's on your mind or you roll through different prompts?

I don't do prompts. Okay. Not to say you shouldn't, but I don't. I just write. I literally like, what is top of mind? What am I experiencing? What do I feel? Sometimes I'll do things like we, you know, look at time. What would I think a year from now or 2 years from now? But for the most part, it's just an open exploration of writing.

Yeah. Okay. Very tactical question.

Yeah.

Since I know that you have 3 kids like I do, and you mentioned time. Now you were talking time in the terms of years or decades. I just mean time in terms of getting that space. Yeah. Before kids, getting up early and doing that was easy. Now you wake up early and you're like, "Oh, this is perfect." And then You know, a 5-year-old wakes up and you're like, okay, now I guess we're doing breakfast and we're doing everything else. Like what's worked for you to create that consistent space?

It's always in the morning. Yeah. I mean, it's a great question. Back when my kids were younger and I knew I had to be very available for their breakfast routines or whatever, I would get up before, make sure I had time before. Now I've actually built it into my day. So I know it's part of your workday. It's part of my workday. Yes. It's a critical, critical component to my work. And it's just like good hygiene or so. It's just a thing I do before I check the inbox. And that's an important part for me. I don't get into my email inbox until after I have journaled because I want my thoughts to be clear to me before other people's ideas come in.

Someone else's.

Yes.

Yeah.

Yeah. So actually, I've just put it in my— it's just in my calendar. So if you were to see my calendar, it's before whatever, 9:00 AM.

I need to be better at that. So questions that you've used with me that I think help getting unstuck are things like, maybe through that journaling, finding something that comes up, a habit or trait, and then asking, is this still serving me? Or another version, when you're trying to get clear, is like, okay, what do you actually want? What do I want? That's something that's been wildly helpful is now I think I do it even before you ask the question.

You do. Appreciate that.

I'm just like, if I could have anything I want, something about that phrasing gets me to a good place, then it'd be this. And I just then either verbalize it or write it out in journaling in a very clear way. And then you're usually asking some follow-up of like, Wow. Okay, great. And so then what would that mean? You know, or— but how do you think about those two questions? Like, this is serving you, and how to ask—

oh, is this serving you?

And, and any way of getting clear on what you want, what would you like, and the what will having that do for me.

Those are the questions that come directly from a coaching frame called outcome frame. It's an NLP, um, There's 4 or 5 more questions to it. I remember them, but I won't go through them all here. But generally, the purpose with those 2 questions— oftentimes we want things without being really clear on what it is we actually want. So we might say, like I hear all the time, I just want to be successful. What does that even mean? And how will you know you've had it? And what will that do for you? So asking, what would you like? And what will having that do for you in continually kind of circling around that helps people get really clear. And so they're not chasing some vague notion of it. The way that one of my teachers gave it to me was, you don't sit in your car, pull up Google Maps and say like somewhere. Or what most people do when they think about their life is they'll say what they don't want. So you don't say, don't go to Boise.

Right.

And it doesn't work like that. The more clear you are about where you're going, And then the more clear you are on like what it is and why it matters to you, the more clear you're going to be on how to get there. So, so, so yeah, peeling back those layers is really helpful. And we often will throw around these terms like be successful or be effective that don't really mean anything until we actually get crystal clear on it. And then the question around serving me, how is it still serving me or how might it be serving me?

Yep.

We can often make parts of ourselves bad. Like, you know, the part of me, they'll call it the inner critic in me, the one that even as I speak to you now saying, oh, that was dumb. You shouldn't put it that way.

Could have phrased that better.

Could have phrased that better.

Done it. Yeah.

And Kara's over there thinking, what is he saying? What's he doing? Like that part of me, it's easy to say stop it or be quiet or I want to ignore that. But that actually doesn't, it actually amplifies the experience of it, if you will. It actually like gets me further into the critical space versus to say, I'm appreciative that that part of me is there. How has it served me? Well, it served me by driving me to be better consistently. And there's something about appreciating that and understanding that that actually helps us move forward versus it taking a hold of us more fully. So it's like, I just appreciate that that part of me wants me to be better and I got it. I can figure this out. We have editing tools. We'll be okay.

Right.

Yeah.

Okay. So I want to go down, this might be a deeper turn, but I'm thinking back to the Reboot Bootcamp. It's the first time that we met. I went on a walk. You call them dialogue walks. I call them listening walks because you're actually not allowed to have dialogue.

That's right. Yes.

I went on a walk with now a good friend of mine, Nick Gray.

Oh, cool. I didn't realize that.

That was the pairing. Yeah. Now I've hung out with Nick many times since then. But this question, this is at Brad Feld's house actually. And so he has this big property.

No longer his house.

Okay. Big walking path around it and everything like that. Do you remember the question that everyone was sent out with? You've probably done a bunch of different ones. I think this time it was about someone else who— a trait in other people that drives you crazy.

Oh, yeah.

Yeah. And then the exercise is to go and— is it for 15 minutes?

Oh, yeah. 15 minutes each way. Yeah.

And so you go out with this other person, walk shoulder to shoulder, and just answer that question. And the first time you go through it, the only instructions are answer that question. And if you run out of things to say, start over and do it again.

It's like the morning pages. Keep writing. Yeah.

And so going through that, first it was like to just talk without— the other person's not allowed to say anything other than my job is to set a timer for 15 minutes. And you're like, how much is left? And you're like, 14 minutes. You're like, okay, you know, that's all it is. And so to go out and, now that I'm talking about this, I'm realizing this is like, I guess as you're saying, this is just verbal journaling.

Exactly.

Yeah. But so you go out and answer this question and talk about it usually takes about 2 and a half minutes to find the answer to the question. And then you're like, okay, well, I guess I, start over, like start at the beginning and go again. And then that second time, and maybe a third time, but usually the second time you get to like a much deeper layer. And so for me in that, I was able to really work through the traits in other people that I dislike. And I think it was even going to specific people. And what I came up with is people who squander opportunity. And just like there's so much in the world and if you just take that and you're like, yeah, I'd rather sit at home and play video games or you're not willing to take action or do these things. And it, you know, realize like that drives me crazy. And then I'll shortcut some of the story, but really peeling back these layers, realizing that, oh, it drives me crazy because they're a burden on other people and people that I care about. And I never want to be that, you know, and so like take action, do all these things. But the distinction of the how is this serving you, like on one hand I've realized I was holding on to all this emotion and anger and all this stuff towards people that I like felt like were squandering the opportunity that they had and were being a burden. And I never wanted to do that. But then I realized, oh, I don't have to hold on to that anymore. And you real— like for me it was realizing the amount of I guess, pain and conflict and stuff like that, that it caused, of being angry at people who were bringing some, but this, how does it serve me? Also realizing this thing that I don't need anymore is what got me here.

Yep. Absolutely.

And so my drive to never squander an opportunity, all of that is what created the company and the relationships and all of these things. And so it's so interesting to play in that space of, What, like, does this serve you? Does it still serve you? Can you, like, just let go of it?

Yeah.

There's a story that stood out to me a lot, and maybe you can tell it. I don't know that I know the names or all of that, but I first heard about it from you and Jerry, is the Japanese soldier.

Oh, the little soldier. Yeah.

The little soldier.

Yeah.

You talk about that?

We, yeah, we've talked about that. Yeah. Yeah.

But can you tell?

Oh, sure.

Tell it on air.

Well, I believe that Bill Plotkin is the one who popularized this and he's written a number of books. They're great. Of course, I can't remember off the top of my head. He talks about the concept of the loyal soldier based on the notion of Japanese soldiers who were in caves, I think particularly around the Philippines after World War II, who had no communication with the mainland. And so from their point of view, they were loyal to the end.

They were told, "Fight until your commander tells you to come home." Exactly.

Yes. And so 5, 10, 20, eventually 30 years, I think 30 years, the last soldier was found in the '70s, still from his perspective fighting the war. And so the loyal soldier concept is a reflection of the soldiers within us who showed up to fight a war that's no longer here. And they continually are looking to fight the battle, even though the war is long over. And it gives us a framing to help understand that this part of us is just trying to do something really important. For you, it's to never be a burden. And we could, you know, we could get into why that's the case for you. But that soldier said, hey, the war we fight is to never be a burden. And by the way, that war never ends.

Right.

So I am constantly on the lookout for it. Now, what we talk about in the boot camp and we talk about with our clients is what you— you don't make them wrong. You don't criticize them. You don't— what are you doing, dude? It's 1974. The war ended 30 years ago, right? You celebrate them. You celebrate them for their loyalty, and you hold a parade. Is actually, I think, what the Japanese did.

They had a parade because I believe they tried to reintegrate these soldiers who'd been fighting for years beyond And at first it's like, what are you doing? You are hurting people. You are killing people. You're causing death and destruction for something that does not matter. And these soldiers, I mean, especially if you think in Japanese culture, like it being so honor-based and all of that. So then you're at extreme shame. And these people were never able to reintegrate into society. And then taking an entirely different approach, Which the Japanese ultimately did of saying, let's honor all of your service. And only in doing that can you end the chapter and, uh, you know, release it and let go. So for like, I think for me was realizing that I carried so much anger and resentment towards people that I felt like were a burden on my mom. And then, and like, that felt so important to protect her and fight for her and all of that. And then realizing like, oh, that may have been true in the past, but now she has like a master's in nursing. She's earning six figures a year. Like, she can take care of herself and she's doing all these things to take care of people. And because that is the truest expression of who she is, like, she does not, she does not need me to fight for her or any of that. And so then you, to be able to realize like, oh, Like, this trait is no longer needed, but instead of feeling shame about it, I can celebrate, oh, but this trait of never being a burden on other people, like, gave me every bit of drive and desire, like, created all these incredible things. So now let's close that chapter, let's honor it, let's celebrate it, and now let's go from create and continue from an entirely new fuel.

Yeah, it's the honoring that allows you to move forward. The thing that I can't help but not ask about is when I hear you talk about not wanting to be a burden, what is that stated in the positive? Just help me.

Not wanting to be a burden. The inverse of that? Is it something you're thinking of?

I'm just thinking like I am I am self-sufficient.

Self-sufficient.

Something to that effect. So that we can see that that has been really powerful for you. Right. It's like, I will create more. Not only will I not be a burden, I will create more value than I need and thus take care of—

I will create abundance.

I will create abundance so I can take care of people, including my mom. So there's that piece. But what I find Behind loyal soldiers who are fighting the war is the very thing we're trying not to do is the very thing we want. So there's a part of you that still wants to be taken care of.

Oh yeah, 100%.

Which is then to say not be a burden, but that's the sort of the negative way of putting it. So by celebrating the soldier, telling it the war is over. So if we go, I'm going all over the place, but if we go back in time. A lot of the patterns I see with clients, the things that are driving us, the things that you talk about, like, how is it serving you? Or how is it serving you? The loyal soldiers, those emerged at a time when that thing felt life or death. So for a child to feel like his mom was overwhelmed or had too much to take on to the point where she couldn't handle anymore, i.e., don't be a burden. It was life or death for him to step up and be responsible and to not be a burden. Hence the soldier is born. And then as you grow up in life, he's constantly looking for wars where being a burden is a risk and steps up and fights the battle. It's a survival instinct is really what it is. And it feels like that. Like, I can imagine when you feel like a burden, there's a physiological response, right? So when you honor the soldier and you end the war, you allow him or you, to integrate with you and recognize that you can actually be a burden or depend on other people. And I would say this has been part of your leadership journey. You can depend on other people without being a burden. And once you integrate him and celebrate him, you can now choose to depend on other people versus always defaulting to never being a burden.

Right.

So the way that I describe it with clients is we move from it being a need to a want. I want to depend on people when the time is appropriate. This is an adult decision versus I need to not be a burden at all costs.

Because depending on other people is part of healthy relationships and leadership, right?

I mean, you can't scale a company to $50+ million in revenue if you are doing it all. I mean, maybe there's someone out there. I don't know.

But the reason I think this is so important is that there's a line that I've heard entrepreneurs throw around. And that is chips on shoulders put chips in pockets. And it's this— just the idea of like, what is your fuel? And so many people are using a fuel that like burns hot and burns, you know, burns very bright and very short.

Right.

And you're just like, I don't think that that's— it may have worked really well to get to this point, but it's not working now. And so to spend that time and dig in and answer like, oh, what fuel am I using and how can I switch that to something else?

It's a question that I get from every single client. And then I will usually get a follow-up if they're parents, which is, oh wait, I'm this way because of how my parents treated me or didn't treat me. Oh wait. Well, I don't want to do this to my kids, but I want them to have the chips on their shoulder at the same time.

Right.

It's like, I see that all the time. And, um, the truth is that the soldier is a powerful— it's a rocket fuel. Like, it can literally lift you out of poverty into wealth by building a profound company. It's— it is a drive, but I have not seen a single person where that energy didn't run out. And where they didn't hit a wall and realize like, I got nothing else. I can't go any further with what has gotten me here. What got me here will not get me where I want to go.

Yeah.

And, and the big opportunities, like I was just referencing earlier, is to move from needing to not be a burden in your case to wanting to depend on others and wanting to create something. It's, it's a different feeling. It maybe doesn't have the, the quite the jolt as a survival instinct has, but it's sustainable. Sort of like the difference between eating a nice healthy meal or eating a bunch of donuts, right? You might get a jolt from the donuts, but then eventually it's going to kind of hang over. You have a hangover with that. So it's this sustainable drive. And I've seen it with every founder I've ever worked with. They have to make that transition eventually. From needing to be something or prove something or carry something to wanting and then selectively using that tool in their toolkit.

I think for many creators it exists in this idea of I never want to have a team and into at some version, oh, I would like to have people that I could depend on who would help bring my ideas to life, you know, and, and all of those things, which then brings into this whole world of conflict. Like some often the reason If I talk to a creator and they're saying, hey, I want to scale to this level without any team members, and they're so excited about AI because they're like, oh, I could finally do it, right? Or, or whatever. But it's usually avoiding something, right? Maybe they were at a company where, or more likely in a family where conflict was, uh, scary, something that should be avoided.

Yeah.

All of that. And so then they're saying, um, How do I make sure that I'm never— like that never happens to me? Two questions that I love are, what was the time in your life that you saw something happen and you said, that will never be me? And then the other one is like, what's the time in your life where you saw something happen and said, that could be me? And like, people want to journal on specific things. Those are two good ones. But the, that will never be me brings you to, okay, well, if I just never have a team, Then I won't have conflict. Then I won't have, you know, all this, right? And so something that you've helped me a lot and probably helped hundreds of other leaders with is this reframe of from conflict being a bad thing to conflict being a good thing. So can you talk about that?

Well, I'm curious. I, I'm asking, answering the question, but so what is the good thing that you see conflict is now?

Uh, conflict is progress and growth. Conflict is care. Usually the lack of conflict is either there's nothing meaningful happening, there's no care, there's no closeness, and maybe nothing important, you know? And so as you play, like inverting back and forth, so the easiest thing is in avoiding conflict is just like, I just don't care. There's a line that Keanu Reeves said in an interview. He's like, look, I'm at a place in my life. I don't want to argue with anything about anyone. If you say 2 2 is 5, I'm like, cool, I'm happy for you. Which on one hand, that prox— like that distance and choosing your battles is like very healthy.

Sure.

Yeah. You know, instead of the like, someone is wrong on the internet and I must correct it. But then it's just like, if you don't care, then you're not going to build these relationships. You're not going to make real progress.

Right.

And so for me, conflict, you know, willingness to engage in conflict in a healthy, intentional way is probably one of the, like, truest expressions of care about a relationship and then care about a goal. Yeah.

I think that's very well said. Absolutely. I think it's important, kind of going to what you just said there, it's important to, when in conflict, ground you and the other person in what you're there for. And usually you find that you're aligned. Like we're both here because you want to come up with the best idea or build the best product or whatever it may be versus who's, I'm trying to prove I'm right versus you're trying to prove you're right. But so I'm willing to engage in the disagreement because I really care. I care about you and I care about this place. I think that's a good framing. I mean, I will always— I've been amazed at this even in my own journey, that just how helpful conflict is in creation, in clarity, in alignment. It creates alignment. It builds trust if done effectively, which I think a lot of times people think, well, I can't engage in conflict because I don't want to upset Nathan. But actually can build our trust by showing him that I'm willing to share my ideas and fully disclose where I am, even though I know it's in conflict with him and that we can actually work it out. And so much of it too is proving to ourselves that we can survive it and thrive in it.

So there's more I could say there, but I think one of the kind of our promise with him of the episode is individual tools and a tool that you and Jerry and Reboot I have given out related to it is, uh, you know, these questions about conflict and I'll just run through them, uh, because I've used them so many times, but it's, you know, as I've had so many leaders in the company myself and then I've assigned it to other people in the middle of conflict and said, go journal on these 4 questions and then let's try to help facilitate a conversation about it. But it's, um, what am I saying? That's not being heard. Easiest to start there. I've been saying all this stuff and Dan just does not hear. Right? Like, and then what's being said that I'm not hearing? Ooh, that one's a little harder. You know, I gotta actually like, hold on. There's some ownership that I finally, like, I gotta start to take.

That's the one I usually forget to say.

Yeah. And then like the next most, or like layering up in levels of importance, I think is, What's not being said that needs to be said? Because then you're at this point of, oh, we could conclude this conflict quickly. You said something, I responded to it, back and forth. We good? Okay, cool. We've concluded the conflict. We haven't resolved it. And so usually the resolution that you don't want to do because it's like a whole nother thing is like, okay, what's not being said that needs to be said? You know, it might be about a lack of trust. It might be about so many things. And the last one, which I think is the most challenging of all, is how am I complicit in creating the circumstances I say I don't want? And that one is just like a gut punch every time because you're like, I say I, you know, I want to create this environment in my company. I have these goals and all of this. And how am I continually like, how am I making these circumstances where again and again it's creating the thing that I don't want. And it's in a, you know, the very popular version of this would be like Jocko Willink's Extreme Ownership. You know, it's just an extreme ownership. Like, how is this all my fault? And I've assigned this. I can think of a specific time where I assigned it to two leaders in our company who were really struggling to work with each other. And like, it was likely that one of them was going to quit and couldn't figure out who was right, who was wrong, any of those things. I said, just go journal these questions and we'll talk about it. And they both came back and one of them had written out really thoughtful, like, what am I saying? It's not being heard yet. It had a few lines. What's being said that I'm not hearing? He had like actually quite a few more. And we got all the way down to how am I complicit? He had a lot. And then the other person had maybe a line or two for each one. And you could immediately tell one person cared very deeply about resolving this conflict. And the other person was like, I don't think this is worth my time. And that even that was incredibly telling.

Yeah.

So that was a bit of a monologue, but those like have just been some incredibly powerful tools. Both in my life and also in leading a company.

That's amazing. Well, those are the— Jerry, my, my colleague and co-founder, I think also with his therapist, Dr. Seraj, gives credit for those. It's interesting though that you put that fourth one in there, how am I complicit in creating the conditions I say I don't want, because that— I wouldn't normally lump those together.

Yeah.

Um, but I could see how it's helpful there. There's a, there's a framework sometimes we'll teach, um, called The Net, which kind of builds on this, but it's imagining like a tennis net or a pickleball net. And on this side of the net is, on one side is my intentions. So it's like, I know my intentions. And then related is, I know the impact of their words on me. And on the other side of the net are their intentions and the impact of my words on them. And we can only know the things on the other side of the net when we ask. But so much of the time, like the question of what am I hearing, then that's not being said. So much of the time we are assuming their intent. We're assuming what they mean by this or what they say by this. So that question is just another way I think of getting out of those and laying out all the assumptions and like, wait a second. When Nathan said, I don't like that idea. What I actually heard was, I think you're stupid.

Right.

Or like those types of things happen all the time. And by getting a little bit of distance from it, like I can actually see, oh, okay, that's an assumption I'm holding that's actually holding us back from engaging in a real conversation about the ideas. And by laying that out, I can actually engage with it directly, but it doesn't really matter the tool as much as like, if you're willing to engage in the conversation.

Yeah.

And in most cases, honestly, it's, you know, what am I not being said that needs to be, what am I not saying that needs to be said? Like in most cases, people aren't being clear and direct.

Mm-hmm.

Um, they're holding back too much, and just doing that alone will help stop some of the, the, the, the jam, I guess, if you will, the traffic jam.

Something that I run into a lot personally and have seen so many other creators and founders do is this like love for the magic bullet.

Mm-hmm.

And usually a new magic bullet. And so it's, there's a problem in front of us, maybe in Kit's case it's that We're not growing in the way that we want, and so instead we're, okay, let me try this brand new feature or idea or marketing campaign, and that is going to solve it. Is that something that you see across the board with a lot of founders? Like, is that a common theme?

Absolutely, yes, I do. Um, and we'll come back to you in a second because I think you have, uh, you've shown this from time to time. But, um, I would say that my observation is the discomfort of not knowing, of not knowing the answer, not knowing you'll be okay, can lead to this frenetic activity of basically avoiding the feeling by doing. It's like, um, I was just with some, some founders yesterday actually, who their core business has slowed down quite a bit. And instead of actually just really sitting down with that and say, okay, what's happening here? They have spun up about 15 different initiatives. So there's a lot. And their team is overwhelmed and stressed. Wait, we're doing this now? We're doing this now? Because the feeling of not knowing and the feeling of seeing the numbers come down, which brings up this existential, like, what's going to happen to us, is so intense. They want to avoid it at all costs. The opportunity is the case with all my clients know this is first to feel it. Like, what is the feeling? Oh, it's really scary that this thing I love. That represents my livelihood may not work out. Awesome. Just feel that for a second.

Mm-hmm.

Not to dwell on it, but to actually feel it so we can move forward. And I see that it's crazy how often that people are avoiding that, but just feeling that they can move forward. So first that, and then let's look at what you're doing. Is there really a problem that's gonna be solved with 15 new initiatives, or are we running away from the problem?

Right?

And what would it mean to sit with it and to face it? What does it bring up in you? Now, you've been there.

Yeah, quite a few times.

We, we talked a lot about this, and I forget the metaphor— was the skyscraper versus the strip mall?

Yeah, there's a bunch of different ones that I've used over time. But what I would do— I've had plenty of ventures or projects that have done well and taken off, and so I know that feeling of like Ooh, I don't know if it's quite lightning in a bottle, but something like that. I'm like, oh, that worked. And I have this core strength or ability in generating ideas. It's very easy to come up with ideas for me. And that's the case for many creative people. And so what I would do and what I see other people doing is saying, whatever problem is in front of me, I'm going to go around it. I'm going to solve that problem by doing this other thing. Now the thing that I can do, which anyone who watches this, uh, this show on YouTube is probably not surprised by with the board, is I can make the most elaborate plan of how all of this is going to work. You know, the string and the marker and the everything, you know, you're just like, and then it's all gonna come back together and see, then it'll be perfect and it'll get us out of this growth problem, team, whatever. And it's usually very, very complex and it almost never works. There's lots of things that I've had to go through some pretty painful moments to kill off or shut down, like accept that, oh, that's not going to work, even though I still believe in it, um, because I couldn't put the resources behind it. And so like, yeah, it's been one of the biggest struggles for me is to maybe be like, uh, Ryan Holiday's The Obstacle Is the Way of saying like, okay, but what is the core thing? And to go straight through that and go to that problem rather than avoiding the feeling, avoiding the problem, avoiding the hard work by chasing something exciting.

So if you were to give yourself advice on how to address or how to change that pattern, if it was— was that it, or is there—

I think it's— yeah, it— maybe to go a little more depth into each one, like actually feeling it, which that took a lot to get to the point One of the very simple things that I actually probably did for the very first time at that reboot bootcamp was just answer the question, where in your body do you feel it? Because it's like, what do I feel? I feel, um, stress. Okay, next. You know, and everyone there was like, and where do you feel that? Oh, I feel it in my chest. You know, it's like, and like just sitting with that.

Yeah.

The first thing it does is it makes it not scary. Cause you're like, oh, it doesn't actually hurt that much. I don't know if this happens to other people, but, um, something that'll happen is sometimes my foot will cramp up. If I were to curl over my toes, my foot will cramp up and I'm like, how do I stop that as soon as possible? Cause you're like, oh, that hurts. And if you just let it, not that it necessarily does you any good to just let it, but if you don't fix it right away, it actually doesn't hurt that much. And sort of this thing of like. Oh, I could actually tolerate this pain. And, you know, instead of fixing it in 2 seconds, I might fix it in 10 seconds. And, you know, but just sitting with that and realizing, oh, okay, if this company were to disappear, my family would still be taken care of. I would still have meaning in my life. I, you know, like any of these things. Um, so really sitting in that and feeling it, sitting with what it would mean. And then probably asking, what am I avoiding? Because often when I think about Kit, there's a lot of really boring work that's not my strength. And so it'd actually be avoiding like learning new skills and actually learning a level of resilience, which is, I think would be ironic because something I pride myself on is the ability to take something and stay with it for a very long time. And it's a trait that has served me very well, but often I might do that in the macro and not the micro. And so, and I see this with creators all the time where they're like, oh, I tried to grow this channel on LinkedIn or YouTube or whatever. And then 3 months later that didn't work out. So I'm jumping the next thing, right? The shiny object syndrome. And instead of just buckling down and doing the really hard work, I try to do this with my book.

Yeah.

Where I chased 10 different ways to try to write the book. And huge shocker, the one that worked was sit down and write it every single day, have some systems for accountability, hire a professional to give me advice and provide some of that accountability and give me a feedback loop. And just just push through it.

Most of the time, I mean, not all the time, but most of the time it's not even the problem or the work we're avoiding. It's the feeling that we have with the problem or the work, either whether what it defines or means about us or what are greater threats. Like, oh, if this happens, this happens, this happens. I mean, you can't tell me how many times I work with founders who was like, the copy's off on the website. Like, well, what's the fear behind that? Well, then our numbers drop off and then eventually gets to this falls apart. And I'm out on the street.

I lose my home.

I lose my home. And that, and that feels real. And so I'm going to do all this other stuff to avoid that feeling. And the much faster way to do it is to feel it. To your point earlier, I mean, I love the, the, the lesson you pulled from that reboot bootcamp, which is to feel it and to name it in the body, which actually is to force you to be curious and to feel it, not to dwell on it, but to actually be able to move through it. Another metaphor, because so many of the things that we avoid are fears or anxiety, a metaphor I'll often give clients, especially if they have kids, is— this comes from my own experience— but to see the, to recognize that anxiety in some ways is a bit like a temper tantruming toddler. So I will, I often think of my now 8-year-old at a Walgreens losing her mind over a Minnie Mouse phone that she wanted. And so what we tend to do with anxiety is either tell it to go away, I don't want to hear you, give into it, buy the phone, ignore it, walk away. None of those actually make it go away. And all of them actually tend to give it more energy. Certainly if I were to yell at her and then, "Stop it!" She gets louder. So what is the response? You get down on your knee, You acknowledge that she's having the experience. In a sense, this is the feeling it internally. And then the energy dissipates. And then we actually have the ability to make some choices. We have the ability to solve the problem. In this case, not buying the phone. But at least she's not losing her mind about it anymore. She's just crying and she's now available to come with me. Same thing if we just slow down and actually feel the feeling. Okay, I'm feeling a little nervous about this. I'm feeling really scared about this. Wait a second, this one thing makes me worry about the business. Okay, now we felt that. Now you actually have an ability to face it and to solve it, which is what you've done time and time again versus what you've done in the past, which is I'm going to almost build an entirely new business over here so I don't have to feel the existential challenges that come with this problem. But if we can go like, wow, that's scary. Okay, now how do I solve this? It's much faster, much simpler, frankly, much more productive. So, you know, I, I spend so much time in the feeling and placing in the body, not to get people to dwell on it, but to actually feel it. And that helps them move forward. So maybe that's one simple thing is like, what am I feeling? If I really were to feel what's here, what would I feel? Where did I feel it in my body? What might be, I'd be avoiding? And avoiding tends to be like walking away from the tantruming toddler as opposed to being with it, right? Which will allow you to move forward.

So yeah, I can, I can picture that Walgreens scene perfectly. And if you just were to like sit down on the floor next to them, like, it would totally change the situation.

Super hard to do, but yes.

Yeah, when everyone's looking at you and everything, there's people in line behind you and whatever else. But yeah, and then you just switch that fear to curiosity.

Exactly. That's exactly right.

Because it's— for anyone who leads a team, it's an entirely different place to lead from, and your team will feel every bit of it when you're making these decisions out of fear. Fear of missing growth numbers, losing a customer, losing team members, any of those things. I mean, you're more likely to make those things happen. Like, it is more likely to come true if you aren't willing to deal with the fear.

Absolutely. We used to have a saying on our Reboot hoodies that said, um, #GetCurious.

Mm-hmm. I have that hoodie.

Uh-huh. And, uh, we would say at the boot camps, when the going gets tough, turn to wonder.

Say more about that.

Well, it's kind of what you were just saying, is that when we are curious, it's actually hard to be lost in this deeply fearful place.

Mm-hmm.

Oh my gosh, this is scary. And like, well, actually, what's going on here? What can I learn from this moment? What's important here? What am I feeling? Like, whatever the questions may be, there's something about going into a curious space that gets us out of that maybe existential spiral.

The visual that came into my head of when going gets tough, turn to wonder, is like backpacking in the mountains. And you know, the pack is too heavy and the blisters are on your feet. Like it's all, and the, it's gotten steeper than you thought it would be. And you're mad at your friend for suggesting the hiking trip even to begin with. And you could, yeah, you could live in that spot or you could turn into like, oh, it's amazing how far we've come to look out over the valley beneath you, to look at the peaks above you and to just really celebrate. I think that's something that you've helped me do. So many times is to look around at, like, to just get that perspective and to ask better questions, to notice the feelings. And it makes a huge difference. Like, we just spent a little over an hour on a podcast episode because I believe that this is far more important than any pricing strategy we could map out on a board or any tactic or something like that. So I so deeply appreciate our relationship over the last 7+ years and you coming on the podcast and sharing all of this with everyone else who wants to go on this kind of journey.

It's a privilege not just to be on the podcast, though I appreciate that, but the real privilege is being in partnership and being in relationship with you. Really value our relationship. I appreciate that.

If people want to check out anything that you're doing, work with you as a coach, where should they go?

Reboot.io is probably the best place to find me and find more information.

Sounds good.

Yeah.

Perfect. Thanks for coming on.

Thanks for having me.

If you like this episode, we actually did another episode with Dan where he interviewed me. That one's a lot more of a personal look at my own growth as a founder over the last 6 years that we've worked together. So we get into what's changed, where I've struggled, and how Dan's coaching has helped me lead through it. So be sure to like the video and subscribe, and I'll see you next week.