Motorboat Leadership vs. Sailboat Leadership

I need a software update for myself. If I don't become a billionaire in my life, it'll have been a waste. You see a little kid who's playing Monopoly and is taking it so seriously, they start crying. You silly kid, what are you doing? This is just a game. We didn't wanna start a new business this year. I was really pumped to start a, a bunch of businesses in the beginning, and then it slowly started being like, ah, it just doesn't feel right anymore.

Jesse, are you pumped? I feel like we've been doing these podcasts and you're not getting the energy. I want the Jesse energy so fired up, like, that Jesse can't wait for Andrew to come to St. Louis tonight. Not the, Oh, what happened?

I'll be pumped when you're in St. Louis, as long as you're—

No, you gotta be pumped always.

No, dude.

Do you have a topic that you're especially pumped about?

I don't know if I'm pumped about it, but I, but there's a really big thing happening in my life right now that I feel like it'd be really interesting to start to unpack and, and think about with you. Ooh.

Personal or professional?

It's kind of everything. You know, I, you know, you know, I've been on this spiritual journey. Well, I started on what I describe as like a personal growth journey 7, 8 years ago. That's kind of evolved into a spiritual journey. And, you know, the most recently this year, I started to, you know, we didn't start a new business. We didn't want to start a new business this year. Like I was really pumped to start a bunch of businesses in the beginning, and then it slowly started being like, ah, it just doesn't feel right anymore. And as you know, I came back from Japan, and I've been like, you know, I'm trying to like limit. I'm trying to pull back a little bit and just get a little bit of time and space. And you know, a lot of that's Dave. Dave and I were talking a month ago, maybe a few weeks ago, but he kind of gave this analogy of. Shifting from the motorboat captain to the sailboat captain, right? And if you think about that metaphor for a second, it's like most founders, and I'm definitely this way, and this stuff gets pretty deep. Like my worthiness is like, oh dude, if like, if you need me to go sell, I can like get a bunch of meetings. And like there was a time at Ampush where anytime I felt nervous, I would just send like 10 emails out to try to build pipeline. Or like hire it, or like you just you motorboat. You're just like boop boop boop boop boop boop boop boop. I'm gonna get this done. I'm gonna get this done. Da da da da da da da da. Like like and you know given both I think where my energy is personally, the business transitioning to a sailboat captain, right? And like what is a sailboat captain? It's not they don't do nothing, right? They have to do something, but it's like they wait and then they you know they see the winds are going this way and they they shift the sails a certain way and they they're paying attention to what's going on around them and. Um, what I can tell you is like, it feels right to me, that metaphor, and it feels like that is the transition that I'm wanting to make. Um, my being, my essence wants to make that transition. But then, you know, we've talked about, uh, IFS and no bad parts, or, you know, CLG. But then I, then parts of me get really scared.

Oh.

And I'm like, well, this is like, it's uncomfortable. Like, I don't know how to do it this way, or what if it doesn't work?

Or, um, it's, you know, do you ever feel like, what if they're too stupid to do it without me?

Uh, not too stupid, but that's, that was not the word I would use.

Incapable of doing it without me.

Yeah, even that. I, it's not necessarily a negative on someone else so much as it is like, oh, this would be so much better if I was involved. Which like the world, you know, you know this from, from my involvement in, in BG or like everybody's like, oh, Jesse's involvement, that helps. He joins a call and like, It uplevels like he pushes on it. And so there is a thing like I was talking to this coach therapist that I work with locally yesterday and she's like, do you, do you get a benefit from it? Like when I first told her no, and I think that's true, I don't, I don't feel like I need to be needed in that way, although I'm sure there's maybe some part of me that does. But it's much more of like the chances of success go up if I'm, if I'm involved. But what we're seeing in the businesses, I think, and you know this too, is like that's not always the case. And it's also just become unsustainable. Like the first half year, my calendar, the first half of the year was unsustainable. And we did this thing, as you know, that like I did company per day. I think I told you this, but I would get to Wednesdays and I have my date nights on Wednesdays and I would tell Dee like, I should take the next 4 days off because I feel like I've worked 5 days already in 3 days' time because every business was like, oh, this is my day. I mean, you guys do it, right? You slam me with everything that day, but you're not alone. OXA do it and Growth Assistant. And I was talking to this, a lot of this also kicked off before Japan. I was talking to a couple of friends who run holdco type things. And I was asking one of my friends who's done really well with it, how often do you talk to employees or customers of the businesses? And he looked at me like I was crazy. And he's like, what do you mean? Never. Like, unless the CEO asks me to, I don't— like, the CEO gets the, gets the red, the green card to go, hey, I need you to talk to this customer. I need you to talk to the CEO. Otherwise, the, like, the setup is not set up. He's never talked. He's like, I talked to the CEOs. That's it. And so, I mean, his, he's definitely a sailboat captain. Like, you can tell the way he thinks about things. And because he's also buying the businesses, which is a little different than what we did here.

Can you say their name?

You didn't reveal anything. It's some guy. It's a guy who's bought a bunch of software companies. Um, but anyway, it's, it's, it's a, it's been a pretty interesting, very present kind of, again, journal in public sort of thing of like, what does it mean to be a sailboat captain versus motorboat? What's the scariest part for me? Um, and I think, by the way, I think it's relevant because every, every leader has a version of this. You, there's a version of you where you sometimes need to, all of us need to sometimes show up as a sailboat captain, sometimes show up as a motorboat captain, and knowing when to do which one is really important. And in my role, I'm probably more sailboaty just 'cause of where I sit inside of all the things. But you're, but you're not all, when you, you know, you motorboat all the time, that's not always good either. There's times where you have to like shift the wind in the sails, make a call, cut something, pull a, pull a rope, pull a string, and I think it's just a really interesting topic to kind of unpack.

You know, I'll say this, that tell you how I feel about it. You are very much like active and involved and you're a big texter, which means like you're always available. And then suddenly you're saying, I want to be removed from Slack and I don't want to know as much and I don't want to be as included. And I'm like, does he not like us anymore? Is this like the end of our friendship? Is this the end of the relationship? Is this, you know, And that's a weird feeling to, to feel. And I didn't know that you were going through that. And then the other thing is you had set us up with this expectation that you are always on, like to the point where even Nak, COO of GatewayX, when I would say, I, I don't know that I should bring Jesse into this, he goes, no, you should. This was last year. You should. He's your partner. You've gotta bring him in. And now I'm seeing the opposite and I'm wondering like, is it, Is it us? Is there something else? What's going on?

No, I think, I think the reality of it is like, I think the like, the co-founder of a business makes sense that you're really involved, right? Like, and the whole idea behind it was I can get help, get it involved and get it off the ground faster, better, smarter, cheaper. And that's been true for every business. I think now that all the businesses are at a certain maturity level, it started to feel like I was a fractional president of every bit, or, you know, for whatever you want to call it, like some senior person who didn't necessarily have reports, but it was like fractionally involved in each business. And I mean, dude, coming back from Japan, my Slack was a joke. Like the amount of channels I was in and like at every level, like there's our CEO, GX CEOs, it's not nobody that's talking. And then there's like detailed reporting. Then I'm in like a couple random growth assistant client-specific channels. Then I'm like, and I was just like looking at it. I'm like, oh, no wonder I've been like, no wonder my head has felt so busy.

Yeah.

And I just don't think it's, I think there was a time like in life when I felt really excited to be on those things. And I don't, I just don't think I'm that excited. Like, I think the call you and I had on Monday where you were freaking out about something and I was able to show up with love and coach you.

Yes.

I was like, that's what I wanna spend my time on. Like giving Vernon feedback on some specific tactical things. It's just not really what, like, I really just don't wanna spend that much time on that stuff. Not that I won't do it, but like, it definitely starts, it's starting to feel much more like zone of excellence to me than zone of genius. Um, and I'd say the same thing is true for all the businesses. Like, uh, you know, being, with the exception of maybe selling, which I still enjoy, especially if there's like big dollars on the line, I think There isn't, you know, like I like doing our sales thing. I'll take a client call with GA or Ox if there's a big opportunity there, if it makes sense to do that. But even then, I don't want to be super involved after that. But then other than that, it's like I want to talk to the CEOs. I also like— this doesn't happen much in BG, but in the other 2 businesses, there's a lot of mommy-daddy stuff that pops up that I think is like disruptive for the people and it's annoying for the CEOs.

What do you mean? Where like each side has a different opinion and now—

Oh, just like, oh, in Growth Assistant, someone's like, wait, Jesse and Adrian, like, who do I listen to? Or do I have 2? Like the, the last 2 sales leaders at, at GA have both kind of said like, I felt like I had 2 bosses and like, I don't really want people feeling that way.

Um, so then here's the thing that pops up for me. You, is, is it that you're Not accepting who you are today, this year, the last 2 years. And so you last year took on a lot, then this year you still took on more than you wanted to, even when you said, I'm not gonna be in every business every day, I'm gonna give each business 1 day. And now is it that you, that you, you are in a different place and you haven't come to accept it?

Yeah, I think I'm evolving. I mean, I, I think I'm, I think 2 or 3 years ago I was so, I had not done anything new for 10 years. And I was like pumped with like, I wanna start, start this, start this, start that. And now I'm like, you know, part of it, I, it's so funny how naive we are. 'Cause I had forgotten how, what it takes to run a business. You gotta make hard decisions. You gotta kill things. You gotta like focus on certain things. You gotta keep doing the same activity over and over and over again. And, and running a, starting a business is way easier than running a business. Right.

The opposite. Yeah.

I don't know. Well, anyway, but, but as we've gotten to a certain scale with all this stuff that's going on and there's, there's employees in every biz, it's not like there's not any gaps in the businesses. I think for a long time the GatewayX team was filling in gaps everywhere and it just doesn't, I don't feel like there's any gaps in the businesses anymore. Um, but I think I'm also evolving. Like, I think that's the whole thing is like having gone through the spiritual thing, it's like, I don't—

Why do you keep calling spiritual? And I must be crazy for not getting it because when people are responding to the email newsletter where you call this stuff spiritual, they connect with you. And when I think of spiritual, I either think of religion, which is structured, or higher power. When you're talking about spiritual, it feels more like your own internal spirit is trying to come out, like your spirit animal.

It's all one thing. Everything you just— all 3 things you just described are the same thing.

Jesse, I would love for you— I, I don't have a good answer 'cause you're gonna hate this. I would love for you to— and I definitely don't want you to drink. I would love for you to have something the equivalent of scotch with me where you just say, This is my whole worldview on what religion is and spirituality, because you come at it from this have to find out what you are about underneath this fake stuff and ego. There's a thing, and it's not religion, it's something else. And I don't know what that is, but it's, it's worth identifying. And I don't know, honestly, I don't think we need scotch.

I mean, I mean, what, what can I explain to you?

Like, I don't smoke weed, so I can't get into that. I guess we just need to do this. There's something underneath that we are get— that I am seeing, that people are connecting with the messages.

Well, we've written about this, right? Like—

I guess what I'm looking for is more—

Who are you?

Higher—

Who are you?

What? Who are you? Who are you? So for you, it's the spiritual part of this is finding who you are, honoring it.

No, no, no, that's my question. What are you?

Oh, what am I? I'm, I'm gonna give you the most anal answer there is. And the most anal answer is I'm an entrepreneur. I am a dad. I'm an intense, high-energy runner.

Those are, those first 2 things are things you do. They're like roles you play.

So what is like a who am I that would allow me to come up with the kind of clarity that you have, which is—

No, no, don't worry about me. Just who are you? Are you, well, let me ask you a question. Are you your body?

Oh, I see what you mean. If I had to say it, I would say I am my brain.

You're your brain, but, but your brain is going to exist the day you die, right?

Then I would say I would die the day that I die. I get that's where, that's where my—

Who's gonna die?

The brain that is Andrew.

But the brain will still be there. Where will Andrew be?

Isn't Andrew completely gone once the brain is gone?

Well, but the— but my point to you is you're not your brain, right? Because your brain is a series, a sense of cells. It's a bunch of cells and tissue in, in your current, in your physical head. The day you die, it'll still be there. That tissue will all still be there. So that can't be you, right?

Then what am I if I'm not that? I, I just don't see any, I guess some people would say, like my wife would say, we come back, we're reincarnated, we have this other path and all that. And—

Well, there's something in you. There's something in you, right? That isn't your brain. It's, it's not your thoughts. You're not your thoughts. Do you think you're your thoughts?

No, actually, I've come to realize I'm not. I'm, I'm some of them. I'm not all of them. Or maybe some of them are expressing who I am and—

Well, some of them you, you may choose to, to agree with.

Okay.

Like, one way I love to ask this question to people is like, have you ever had the thought you wanted to like kill somebody or pummel someone's face?

I haven't, but there's something like that that's not coming to me now. But yes, it's like this weird thing, right?

Did you do it?

No.

Well, if you were your thoughts, you would've done it, right?

Okay. So then who am— who, what, what, what is, how does this get to the practical of But who am I?

This is the, this is the gold of the question, because when you start to peel that onion, that question, you start to go, who am I?

So how do you answer that? Who am I?

Well, I, I think that there is something inside of me. Call it spirit, call it consciousness, call it life. Some people just call it life energy. That exists in my, in me. It also exists in you. It also exists in a tree. It also exists in a bug. And that energy, like, that is, that is, I am that. That is like, there's an energy there that's aliveness, that's conscious, that's aware, um, that doesn't exist in like a rock, or maybe it does in a rock, but maybe it doesn't exist in like this bottle, right? Um, And there is something distinct about something that is alive, especially a human being, because human beings are aware of our alive, like the fact that we, we exist. And there's an argument of whether or not animals or trees and stuff are, but, um, but there's something inside of, of me that is none of the, it's not what I look like, it's not the physical, it's not even my gender. It's just something else. And that, and that thing is. The same thing that's inside of you, that's inside your wife.

Just when I was with you, suddenly you say it's the same thing as inside my— all right.

Well, is it? Hold on. Do we both breathe air to stay alive?

Yes. Oh, I see what you're saying. Okay. It's not that we're the same creature or the same thing. It's just I have a thing. You have a thing. So now what?

Hold on, hold on, hold on, hold on, hold on, hold on. If you define us, if you define what I am as awareness or consciousness, you also possess awareness or consciousness, right?

Okay.

We both possess the same thing.

I do.

Or we are made of the same thing.

Okay.

That's like when somebody says everything is one, that oneness, that awareness, that consciousness, it's the same awareness and consciousness. That's where, like, it's the same thing. It is the same thing. It's not that we, it's not that like, there's no, like, there actually is not any real disconnect between, there's this like illusion of separateness, right? That you're separate from me and I'm separate from you. But underneath your face and my face and my name and your name and my thoughts and your thoughts, there's just this like alive energy. There's this awareness. That's You know, that is in Sikhism and a lot of Eastern faiths, like that is God. There's no God. There's no like God in the clouds who's judging people and whatever. There's just this energy force that's around us, this alive aliveness energy. It's the love, like energy of creation, the energy of love. And it's, it's around us and with us. And, and that's, that's what it is.

This was so much easier when I was living in New York and it was all about like how much money you have defines where you are, what you're building matters, and everyone else, I don't know, falls in line number-wise. It's a lot harder to try to grasp this, but I'm, I'm getting a little bit of this. Here's what I'm thinking.

The challenge of it is that, is that when you, when you die, you don't take any of that stuff with you.

Yeah, but when I finish playing Monopoly, I don't get to take the little Monopoly dollars with me, but I still enjoy it in the moment even though I know it's fake dollars.

Oh, that's, that's great if you enjoy it in the moment, but that's not what most people do in the moment. Including yourself, you suffer, you agonize over, oh my God, this business line's not gonna work. Oh, this is horrible. You miss the moment of your, of your kid laughing 'cause you're worried about 20 grand in revenue. And, and so it's not, it's not the monopoly thing is true if you truly could show up as life is a game. And it's, it's a, if I get in, you know, oh, it's a fun game, I'm gonna play it and then I'm gonna be done with it and that's fine. I'm gonna enjoy it. Most people don't.

Yeah.

We get, we, we think we're on the board walking on Monopoly and we like, you know, you see someone who is playing a game. They use this analogy in spiritual talks all the time. You see a little kid who's playing Monopoly and is taking it so seriously. They start crying because, because you bought the property in their third thing and you're like, you silly kid, what are you doing? This is just a game. And that's what, you know, someone who's really spiritual says. It's like, hey, New York person, all you care about is money or whatever. You're gonna leave the world empty-handed.

Yeah.

There's no question about that. Okay.

So I'm scratching at the surface of this understanding. How does it now come back to you finding your way in business and understanding that last year you wanted to be super involved, then 2025 comes around and you say, you know what, I think I'd like to have one day. And now you're evolving towards a sailing metaphor, How does, how does that understanding of who you are lead you to make decisions like this?

Yeah, I think one of the, one of the most powerful shifts for me, and I, I'm by no means 100% of this and great, you know, it's still a work in progress. I'm a 7 Enneagram, which is, you know, the, they have, the Enneagram is sorted into head types, heart types, and gut types.

Mm-hmm.

And a head type means like my brain thinks through things. That's how I process what's going on. And back to this, this point of like, we're not our thoughts. One of the biggest shifts for me has been to like trust my energy, even to like know my energy, know my intuition, and then trust it versus the thoughts that go in my head. And for most of my life I've been like, okay, this is This is the right thing. Which job should I take? Well, let me do the expected value. Let me do the analysis and let me choose that option. This rigor we've talked about. And I think there's very few decisions, you know, the big decisions have to be made based on energy and intuition. So for me, I think following what's getting me excited, what's energizing me has been a really important sign and it has evolved. It's not like I was doing, I was totally wrong where I was a year ago or 3 years ago. It's like there's different things guide— it's almost like there's something guiding me. And I would, I would argue there's always been something guiding me. Um, I just didn't necessarily know it or was aware of it, but it's, but I'm becoming more aware of it and more willing to go, oh, hey, this doesn't feel right. I'm not gonna force myself to do this thing that doesn't feel like the thing I do. Just 'cause we said GatewayX is gonna keep starting new businesses, if it doesn't feel, if I don't feel excited about it, if my energy's not like, I'm gonna tap into that intuition and listen to it.

Yeah. So when we reconnected and started talking about, at this point it might be close to 2 years, the thing that was driving you was being the person who got to launch all these ideas that you wish you could have done back at Ampush, that now you finally get to do it. If it's not that that's driving you, what is it?

No, but I don't think, I don't think that's what was driving me. I think you may have heard that and that made more sense to you. So you said, oh, that must be what's driving him. Like what, what's driving me was like our call on Monday. It's like my ability to show up and, and help other people learn and grow and be the best versions of themselves. And, you know, this, this idea of being, you know, the CEO CEO, sort of like the coach's coach's coach, um, and helping other people learn and grow and having that impact and having the trickle down of that impact on others. The, the what of the content of the businesses has never been all that important to me. It took me a long time to actually accept that.

But would you then be, would you be energized running a business that just did okay if you got to be a coach's coach of the CEO? That doesn't seem like a Jesse, Jesse place to be.

I, I just don't, part of what happens is they, there's, You know, to be a coach's coach, like to be a good business person, you have to be rigorous. Like there's no way I can teach. I couldn't teach you how to be business, do business and do it in a way that was mediocre because I'd be doing you a disservice. Like standards are part of service, right? Like teaching someone how to be a badass come like so there's almost no version of it where I think that would happen because if I'm being honest about serving somebody and teaching them stuff that I know, then it's like. Right. It's, it's a, it's a little bit of this context versus content, uh, idea. But it's all, again, this, this sailboat concept of like the mo— the motorboat sailboat thing is, it's part of it. It's like, can you have a conver— one conversation with someone that adjusts them and orients them versus 10 different little things you do that, that drive a person forward? And I think that's—

Okay. So then 2 things are coming to mind. The first is, How did you get to this realization? And then the second is, what does it mean to lead a company as a sailor versus a, what is it, a pilot of a motorboat? So how did you come to this realization?

I mean, I, I think, I think starting to tap into my energy and just looking at my calendar, like the, as I've progressed in my spiritual journey, one of the things you start getting more aware of, you're, you're kind of like, it's almost like thinking of you have this core Right? And then you're cutting away layers. And as you cut away layers, like, let's think of a layer as sort of like attachment to money. Right? For a long time, one time I said this to Dave, I said, if I don't become a billionaire in my life, it'll have been a waste. And I believe that. I fully believe when I said it, I fully believed it. And I was so attached to like, okay, my worthiness is attached to money. If I don't make a certain amount, then it's gonna mean that, that I was like, I wasn't worthwhile. And at one point he got me to, you know, through coaching and stuff, like basically see like that can't be true for so many reasons. Like, I don't believe that story. That was just a story I told myself. But it was, there was still, there's still some attachment to money of like, well, I need a certain amount or, you know, and, but there was like, okay, more is better is not true necessarily. Um, and you're kind of like removing a layer.

Yeah.

of the truth. And then you could remove an even further layer around it. And as you start to get more clear, you go, oh, that, that layer is gone of mine. And, and so now the, like, ember that's inside is burning a little brighter and I can feel it more. And I'm like, oh, that's interesting. And so, you know, this, this year in particular, like, for the first time in my life, I was like, the busy calendar, which I've, I've held for 15 years, like, I'm late to things all the time, like, all the stuff of a busy calendar, I was like, This is not exciting for me any— like, I'm not enjoying it. Um, and that didn't used to be the case.

So what, what am I not enjoying? What doesn't feel right? Let's remove those layers and see what comes up.

Well, I'm like, oh, I want spaciousness. I want more time to think. I wanna be able to— like, I'm more likely to show up with love and with you if you're upset about something, or anybody. If I'm like, if I've got time to be present, if I'm coming off some other call and then there's a complaint, then I'm like, well, whatever, here, do this, do this, do this, right? And you've known me now for a period of time where you can probably even sense a behavior change when like last quarter I was just like a little bit more below the line all the time. Like I was a little bit more on edge relative to what I might have been 6 months ago or 8 months ago. And so starting to just realize like, man, the calendar just does— it's not serving me anymore. And there's— it's very nuanced where you almost in some ways you want to be grateful for that approach that you took for a period because it got me to where I was. And then also be able to like let it go and say, it doesn't feel like it's serving me anymore. I'm gonna allow it to go. And, and so you recognize that it's no longer of service. It didn't mean, again, it wasn't of service for 10 years, right? Um, we could have a great car that we drive for a really long time, or like, I think about my time in New York and San Francisco as like great periods. And then it was like, okay, I'm like, I don't, I'm ready to release them now.

Yeah.

And like this is the next period, and I'm going to move to this new city called St. Louis. And so I think these ways of being are very similar. And this one for me right now is like yeah, I could feel that. And then I was like yeah, Dave's like yeah, you want to be a sailboat captain? Like and we started talking about what you would prioritize if you were a sailboat captain. Yeah, what would you? Well, let's let's like let's think about it, right? Like activity is not the if you're motorboat, like activity is the thing. You're like da da da da da da da da. If you're a sailboat, you're like, you're thinking more. You might be looking out on the horizon more. You may be looking at your navigation guide more because you need to think about the winds and the whatever. I'm not, I don't know how to sail. And then every now and again, when it makes sense, you go and make an adjustment. And then you are patient and then you chill. And like someone who keeps adjusting the sails is probably not a very good sailor. I don't know. I'm not a sailor, but like presumably they, they shift them in the way the winds are going and then they allow them to take you where it needs to go. Um, and, and so you're—

Yeah. So in this metaphor, it's more like make a change, let it go, and then unless it's really off course, you let it go and then you bring it back to the next, uh, you, you adjust again versus constantly being at the wheel, constantly trying to—

Yeah. Like we were talking about, like, again, if you're— busyness is not the, the priority. You're not, you're not adding more to your calendar. That's not a sense of how you're valuable. When you're a sailboat captain.

Is that the way that you felt, that if your calendar was full, then you were valuable?

Unconsciously, for sure. Unconsciously, for sure. I, I, I noticed it because when I'd have 30-minute or hour-long windows, I'd be like, hey, what am I doing right now? Like, I, I need to be doing something. Why am I not doing something? And I could feel that. Um, but you know, other, like the quality of the impact. If you're, if you're the sailboat captain, the quality of the adjustment is much more important than the volume or like, Like being able to have one call with you for 20 minutes that unblocks you in some way is way more valuable than 10 little things that I do for BG, right? And then I go, well, what do I need in order to do that? Well, I can't, I can't, I need spaciousness, right? So it's like you prioritize presence, you do less is more, you'd have the high quality impacts. You might be, no, you might know more information, but you're not necessarily taking more meetings. Like there's a whole set of things that it's a very different way of being.

Yeah.

And then I can say I wanna do it, but I also feel scared because it's not actually my normal, um, it's not my normal way of, of playing in business.

No, I tried something like that on Thursday. I was going to, before you left for Japan, you said, Andrew, what about a break? And I said, yeah, I guess our audience needs a break. You go, no, no, I mean you, are you gonna take a break? Are you gonna? So I put on the calendar a break, which was last Thursday, and then I decided I would work anyway. But I said, it's still a break where everyone else thinks that I'm off, so they're not booking. I'll work on my own. I don't know that I was as— I know I wasn't as productive as if I had everything scheduled out and if I knew exactly what I was doing. And that made me wonder if I need that pressure of someone else is showing up, someone else requesting something and working with me. I don't know. What do you think? I'm looking at your calendar for next week. It's still pretty full. So maybe you have some of that too.

Well, I don't think I've made the adjustments yet.

I mean, that's part of the Do you worry about that, that you need the pressure to really perform, to show up?

Well, again, I think if you're evaluating yourself as a motorboat driver, again, this goes back to like, what are you? It's like, if you're, if you're, yeah, you, if you, if, if motorboat is the, is the race type, and then yeah, of course you need someone to motivate you. But if, if you're, if you're sailing, like it's, it's all about what you're, what are you trying to accomplish? So it's not, I think you're still inside the motorboat trying to talk about, well, yeah, if I turn the gas off for a day, that's gonna slow me down, right? I need a person there to tell me that, that I need to drive the motorboat. Okay.

Has there been a time in your life when you did, when you did the sailboat approach? Has there been something that you took that way?

Really? I mean, there's, there's, there's not a ton of them. It's, you know, it's funny, of all the businesses, the one I've spent the least time on since we started GatewayX is Growth Assistant. It's also the biggest. And so it's like a funny example of like, um, motorboat, sailboat, like that one's like, I picked the right market, I found a great person, I gave guidance. Like I've been the least involved in that business. Um, Because originally, yeah. So, so that's a funny example, right? And it's been the one, it's like, oh, well you picked the right market, you picked a good business, you had a good person running it, and it actually took less of your time. And, and it's big. It's, it's as big, right? And if you, in some ways Bootstrap Giants not is the opposite. It's taken the most of my time even before you came along, 'cause I was doing content and writing this, like, and it's probably produced the least amount of profit.

Right.

Um, so I, I think there, there's definitely versions you can see of it where, where like, you know, the, you could see a version of it where you're like, wait, if you, if you make really good choices, right? I mean, you, we could see this in the world. Like they, Figma just went public and like Kleiner Perkins is gonna make billions of dollars off of it, right? Like they didn't do anything. They found the founders and wrote a check, right?

Versus the founders. Well, um, wow. It's interesting actually that there wasn't anything in your life that you were just kind of a sailboat. I looked it up, a sailboat skipper, I guess is what you would use or a helmsman helm. Um, so there wasn't, so you really are the driving force of a lot of things. Like a lot of husbands that I know are not the captains at home, their wives are. I think that's also a very Texas experience.

I think that's true for me, but, but I'm not, I'm not, I'm, I, I think I definitely, I still do the like more is more at home. I'm just not necessarily in charge.

What's more and more, what, what's more is more at home?

Like I want the kids in different activities and I want to go travel with them and I want to, You know?

Yeah. All right. I think I'm getting this new version of Jesse. How do you, how do you experiment with it?

I'm glad you are. I'm not sure I am.

No, I, I am. I honestly, I actually see it very clearly. I see, I see the friction and the challenges with it. I think the one that stands out the most to me is communicating to other people. How does someone whose user guide says, I have never once said don't include me on a message, you've sent me too many messages. go from that to suddenly telling people I don't want to hear and I don't want to be included and not, not have people feel what I felt, which is like there's something off in our relationship.

Yeah, I don't know. I gotta update my user guide, you know. It's almost— and literally that's how it feels internally. It's like I need a software update for myself, right, that, that's gonna reflect the current You know, the hardware, if you will, of my body. I'm like, I don't wanna, I don't know, I don't actually wanna see every message. I actually really want some synthesized information and I wanna figure out how I can be helpful and I can dive in when I need to be told, you know, hey, dive into this and be helpful, but not, not trying to like make sense out of every single Slack channel and every little message that's coming in.

You know, I feel like there, Like we, we in your life would all benefit from seeing what you're doing to grow and how things are changing so that we can see why you are suddenly saying no meetings or why suddenly you're saying don't call me on a Tuesday, your day is Wednesday. Not that you ever say don't ever, it's, but this, this evolution would be interesting. We've been doing the build business in public. It would be interesting to see the build, the build person in public too.

What would you wanna know?

There's a part of me that— so years ago, I hired the best interview producer I know, this guy Jeremy Carrickan, and he would look at every transcript of every interview that I did, like fast, and gimme incredible feedback. And what he noticed was that, Andrew, you keep looking for the Batman moment. And he says a lot of interviewers do, which is like, You're unsettled unless you know that this guy became Batman when his parents were shot. And it doesn't always work that way, but there is this need that I've noticed that people have of, this is the reason why I'm going on this journey. Otherwise it looks kind of like chaotic, like you're just going somewhere. So there's a part of me that wants the Batman moment of all these evolutions. Like one day I came in and there was too big of calendar. And then there's another part of me that wants to see The why and then the what, and then just be told, look, I'm in experimental mode to, to that. I know I'm clearly a person who has a process and is not a crazy chaotic person, but I need, I need to be in, in that mode. And here's what I tried today and here's what worked, you know?

I mean, well, I think it's, I'm experimenting constantly. I think that's probably one of my best and maybe worst things, but Best thing is like, I don't, inertia generally doesn't affect, like I did this calendar thing and I'll, we've done it 6 months and I'm like, oh, I'm changing the whole thing, guys. I didn't like it and here's why. And it wasn't working. Now we're gonna try it this way.

So that's, that's super fascinating. Like from a business point of view, you saw how much we took Daniel Bustamante's mess, uh, like breakdown of his workshop to sales process and we all looked at it and we analyzed the whole numbers. It's really interesting to see these types of things just put together. I'll even give you an example. When you got into fasting, intermittent fasting, the whole process of, I went into intermittent fasting to the degree that you wouldn't have. Here's what I did and here's what I learned and here's what the experience is. And who knows, on Monday I might switch to waffles because there's something else, but I'm going to tell you that this is what it was. That is fascinating. Do you know how many people from 833 were trying Element and how many people beyond were trying it because, hey, there's a fasting with an Element thing. That's fascinating. The, I'm going to try to, I have this experiment where I'm going to try to not show up every day and let the captains like, or do their thing. I'm going to be a sailboat captain, however you want to phrase it. That's fascinating. Anyway, I'm interested in that, that here's my latest experiment. Here's what I'm finding. I don't know if this will survive. Yeah. More of them.

Yeah, I don't, it's interesting because I'm not sure. I'm not sure exactly how this will play out. Um, I think the, yeah, again, I, I think I've gotten really good at noticing when I'm not excited or energized and then honoring it. I think most people are bad at both of those things. They don't even notice, like you, you have come to accept a certain amount of like, this is how it has to be, so I'm just gonna live with it. It's just supposed to be this way.

Yeah.

And there are, there's parts of me, by the way, that feel that way too. There's parts of me that think it's not, it's not allowed that I can only work, I could work 20, 30 hours a week and still make a lot of, you know, like it doesn't feel right. It feels wrong.

Um, I get that.

And, but, but I also am like, man, I like, I see it. I'm like, I'm not energized. I'm not excited about these things and I'm gonna make an adjustment and I'm gonna see what happens and see how it shifts. And Um, there's a lot of trust involved. I think that's a big part of it, right?

Meaning like trust yourself, having people trust you not to, not be flaking out, to not be reneging on like implied relationships.

No, no, none of that. That's, that's, you're still in motorboat mode. That there's a lot of trust that like me having time, let's like shifting the time and being Let's just say looking at numbers more, engaging on the plans more, playing the role more of coach than co-founder, let's say for you, that that's actually gonna serve you and the business better than the version of me that's really involved and really engaged. And because that second ver— the other version is a not trusting version. It's like, well, if I'm not around, then, then this will go in the wrong direction. It's like, it's like, it's kind of almost like a form of CEO micromanagement in some ways.

Yeah.

It's not micromanagement, but it's like, it's like double, it's like hovering, you know, hovering over.

Were you in sailboat mode when John Oberlander took over Ampush?

Yeah, actually that, that's a good example.

Yeah. Okay, good.

I mean, I don't know if I would call it sailboat mode so much as like abdication. Like I was, I was like on the island.

Uh, yeah, maybe, maybe you set him up for like success and so that you could then—

I don't know about that either. I think he did a, I think he did a fantastic job.

He did.

Inheriting something that was pretty shaky and leveling it up. Mm-hmm.

All right. So are you gonna write about this and start to tell people what you're, what you're going through and what you're thinking?

Yeah, I gotta think more about, I gotta think more about what are the difference between the two? What are the trade-offs? What's holding me back? What, what's, you know, what am I afraid of? All these things come down to like what you're afraid of at the end of the day.

I like hearing what you're afraid of. You've made me feel more comfortable with like understanding my fear. I think one of the first things that you do is you go through a list of questions and then you go, can you accept that you're afraid right now? And I go, fuck, freaking A, yes, I can. Can you accept that you're afraid? Anyway, I like all that. Thought I wasn't afraid of anything in business.

Huh.

All right.

All right. See you, Andrew.

Thanks, Jesse. This was great. See you.