Is Spirituality the Missing Key for Founders?
1 Jul 2025 · 47 min
Dave Kashen talks with Andrew and Jesse about meditation for founders. He argues it reduces reactivity and builds resilience, and walks through practical approaches: breath work, apps like Waking Up, even five minutes daily. The conversation covers Conscious Leadership concepts and how gratitude practices like handwritten thank-yous shift how you show up.
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Jesse's got a topic for us. Kick us off, Jesse.
Yeah. So, I wrote an email last week and it was kind of my first email I've written to the list about spirituality. And even in the email, I probably didn't let on as much as Dave and Andrew— Dave obviously knows, Andrew to some extent. And the email was still a little, "Oh, what is it?" and "What does it mean to be spiritual?" and all these things. I don't think I told this to Dave, but we got a massive outpouring around it. And some of the cool things, Dave— and I acknowledge Dave for supporting me in this way— but a lot of people said, it's funny you're just talking about this now because when I see you on video or interact with you, I can feel it. And I was like, oh, that felt really nice. And it felt whatever, true. But, you know, one of the things people always ask about when we start talking about spirituality, like you can talk about Above the Line, Below the Line, and Conscious Leadership and all these things, but everybody kind of goes, where do I start? What do I do? What could I actually do that would show me results?
Wait, they don't start by saying, why do I need to be spiritual? Or why are you talking to me about spirituality? Let me get my business in order and I'll get spiritual. Or let me—
well, what are the benefits? And how could I actually do something about this? Because it's a pretty hard to grasp thing, right? And, and one of the tools that I think is an obvious tool, it's been a tool forever, but I think I want to spend today talking about and ask Dave a bunch of questions about it is meditation. And, you know, did you guys ever see Billions? Did you ever see the show Billions?
Yeah.
Yes. Do you remember the scenes where this is a show for those who haven't seen it, it's like this hedge fund guy, uh, it's supposed to be like Steve Cohen effectively. Some, this hedge fund guy who's insider trading and then this crazy district attorney and they're basically battling with each other and there's these funny scenes where Both of them throw on their timers and both of them meditate. And so, like, meditation is like a big— I mean, it's a well-known topic, but I actually think when I talk to people—
I thought you were going to mention Wendy Rhodes.
Oh yeah. You know, that's my dream, that Dave will become Wendy Rhodes for me. Anyway, but I think the question, you know, people still kind of go, what's the point of it? Or I'm not supposed to have thoughts. I don't know, Andrew, where you are in your meditation journey, but I—
I'm lapsed at meditation because there's so much else to do, and so I don't do it. I've been watching YouTubers lately who did these life transformations who meditate, and I'm starting to want to come back into it, but it takes a lot of time. But Jesse, let me ask you this: when you say spirituality, are you talking about the ability to focus and to meditate? Are you talking about a connection to God, or is there a difference between the two?
That's a good question. Dave, what do you think?
Yeah, I was thinking about the same, uh, same sort of topic, like how loaded that term can be for people, especially because it's often linked with religion, and people have varying degrees of relationships with religion— their own religion, religion as a concept. Um, right, what's—
let's see, I can tell you what I said in the email, Dave. I don't know if you read it, but I think the— for me, the link, Andrew, where they're so important, right, is everybody has the experience of chatter in their brain.
Yeah.
Of this little voice that's talking, right? And most of us, for most of our lives, believe that that voice is us. Right? We just think, oh no, that I think this or this. I'm mad, I'm sad, I'm happy. I'm going to go do this. I'm going to go do that. And one of my favorite, I was telling this to my sister-in-law over the weekend because I was like trying to explain this concept to her. And I go, have you ever had the thought you wanted to kill somebody? Or have you ever had the thought you want to like punch your kid in the face? And most people first go, no, no. And I'm like, no, be honest. And everyone, I think everyone has had a thought of like, man, I want to kill that person. Or I want to like really I'm like, why didn't you do it? If you're your thoughts, why didn't you do it? And they go, oh, I don't know. I go, well, because you're not your thoughts. Those are like, you know, there's this other part of you that's talking, talking, talking all the time. And then there's the other part that's actually listening, right? And I think spirituality, my version of it, is like, it just means there's something bigger beyond you, this little voice that's connects all of us in some way. There's spirit or there's some, something, right? There's something beyond all of that. And I think where meditation plays into it is meditation is, is one of the tools that allows you to actually start to create some, some space between the thoughts in your brain and the sort of, you know, the, the listener and the speaker, if you will. So that's kind of, I don't know, I said versions of that in the email.
Let me say a few things. One, let me underscore that listener speaker 'Cause I start almost every coaching engagement with this. I ask clients, I forgot if we talked about this in a previous episode, I ask clients, "How do you know when you're thinking?" And they notice that voice in their head and I typically say, "Well, in order to have the experience of hearing a voice talking, there must be a talker and a listener, right? If there was no listener, we couldn't experience that." which for a lot of people is like, "Oh, that's an," you know, it's like an unexamined part of their experience of being human. And then, yeah, like I'll often say, if you were walking down the street at night and some like drunk homeless guy is like, "You suck," it's obvious you could ignore that voice. But because the voice appears to emanate from inside your head and sounds like you, it's not always as obvious, but it is just as true that you could choose to ignore it. And I think that's a really important thing to say about meditation. A lot of people think the goal is to quiet the voice in the head, and it is nice when the voice quiets, and it does sometimes in meditation, and it often doesn't quiet in meditation or not in meditation. That's not a problem if you can see through it, right? If you can ignore it, it's just like, oh, this is just occurring, this voice is chatting chattering on in my mind, and then you go about your business. I sometimes use this metaphor, not to pick on homeless people, but, um, you know, about like, you're like in a, uh, you know, you're in your favorite cafe sipping your tea, and this, you know, crazy homeless guy sits down next to you and starts muttering to himself like, ah, you're a piece of shit, you're, you're terrible, you're— God, what— you know, you wouldn't then think he's talking to you and engage and believe what he's saying. And I think that's another useful metaphor. It's like, well, just because the voice appears to be kind of inside us and sounds like us, uh, it's not necessarily even really talking to, to us. Um, or it's useful to think that it's not, almost like it's talking to itself. And then the other thing I just said, spirituality— I had a teacher once who defined The divine as the unknown. I just, I love the simplicity of that. It's like, can we just acknowledge we don't know everything about this experience of life? And so in some way, spirituality for me is the exploration of what's not yet known. And we, you know, so much of us, we want to feel certain, and so we're constantly just like trying to, um, know everything and explore what we already know and sound smart. And so it's like, can we explore and be curious about what is unknown?
And, and that, by the way, you know, I, I think during our lifetime science and spirituality are going to merge.
Yeah, and they are to some extent already, especially they already are.
I mean, you think science is such a funny concept, right? They go, prove it to me. And it's like, well, again, 1,500 years or 500 years ago they thought thought the Earth was the center of the universe. That was what science thought because no one had proved otherwise yet. So what's to say that these things we think today are not going to just be proved otherwise? And I think back to meditation, I think, Andrew, for you, let's say you don't want to be spiritual. That's one of the cool things about meditation is it works. You can believe in nothing. You don't have to believe in shit to sit down and quiet your mind and just— you're not quiet your mind, but sit down and just observe your thoughts. And create space and slow things down. And everyone who does it earnestly for a period of time notices the benefits of it. And now science is studying it and going, "Look at the gray matter difference." And Buddhist monks, they're doing all these things to prove the science aspects of it. But even if you don't believe in it, and I think for people listening, for entrepreneurs, you can just do it because it's like one— I read this Business Insider article of all places a long time ago and it really clicked for me around meditation, which was There's— it's not stopping thoughts. As Dave said, there's two things you're doing, or there's two things, two or three things that happen when you have a thought. Typically you either do something, you take an action. Oh, I gotta send that email. Oh, I gotta, whatever. You feel something, right? Oh man, why do you say that to me? Like I'm mad about it. Or you, um, I forgot the third one, but you, it usually that you do something like there's an action or reaction that happens to your thoughts. That's normal.
Maybe you argue with it. Is that the third one?
Oh yeah, judge it. Thank you. You judge it. No, no, no, that's wrong. You're like in your head judging it, right? Those are the 3 things we typically do with thoughts. And meditation is literally just the practice of having the thought and just not reacting to it. And everybody would agree you could be less reactive and more responsive. And I think, and for me personally, as someone, you know, I started to meditation, like jumped out to me and beneficially wise when I like things would happen that used to happen that would really throw me off my game. And just by staying like that, like just not reacting for one, one more second or five more seconds, it didn't feel like a big deal all of a sudden. And a lot of that was just like literally the physic, like the gym, getting my brain to go, thought is going to happen. Thought, thought, thought. And like, oh, that one goes there. That one goes.
So this is kind of like counting backwards from 10. If you get angry at someone, no, there's more of a benefit. What's the big benefit of doing that? You're nodding like, yes, that's part of it. But is there more, Dave? What's that? Basically, I really need a massive benefit for me to care and do it. Like, the only reason that I'm doing push-ups right now is because if my chest is big, I feel like my wife is gonna like run her fingers on it, and I'm also gonna see it in my t-shirts, and suddenly I can wear t-shirts and feel good and not have to wear this shirt with the collar all the time that makes me look good. And so I need a massive benefit. I see Dave is looking up to see, can I find a massive benefit? Pleading with God.
Where do I begin?
Yeah, where do you begin? What do I get?
Let me share something that, just so I don't forget to say it, which is first, just notice that your inner voice doesn't tend to say things like, "You're so amazing, Andrew." "Oh, you look so perfect today." "Oh, you just nailed that thing that you just did." Wow, is that just me? Proud of you.
No, no, Jesse, does your voice say that in your head? I feel like your voice says that.
No. Well, I think Dave said this to me one time, which is like the ego, the ego is trained. So there are, I think there are people whose inner voices are much more critical because maybe their parents were critical of their life experience. There's some who are more maybe medium. There's probably some who are positive, but you can shift that inner voice with practice. That's not necessarily—
and then the inner voice will be like, yeah, you're amazing. Go ahead.
A little. Yeah. I think, I mean, I've shifted mine a lot over time.
Okay.
That's what, that's why people say to do affirmations. And like Dave sent me his morning affirmation once and I do my own. I'm like, hey, and you can train it. It's still the voice. It's still not you. It's still this, you know, the person.
But at least now it's a supportive voice.
It can be a supportive voice. You're going to have one. Go ahead. But most people, Dave Kashen, today's point, most people's does not tend to be.
By default, most people's inner voice is critical. It's negative. It's like a massively distorted toward negativity. And so first of all, that's just like, why change your relationship with it? It's because it's not connected to reality. It's like you live in a reality that's let's call it like level 5, and the voice would have you think that reality is like minus 5. So just if you listen to your voice all the time, you're in this like really distorted dystopian version of reality that's not actually the reality you're in. So first benefit is to live in the actual reality you're in. And I often say like, I think we're neurobiologically wired for a world that existed like 1,000 years ago. Where lions, tigers, and bears were constantly trying to kill us. And so the voice is a mechanism of survival in a world that was like, again, 10 times more dangerous than the one we're in. So first benefit is to live in the reality you're actually in. And so you can relate to things as they actually are instead of way more scary and negative. And then ultimately, like, there's people who use it sort of functionally. You know, this is where the line kind of starts to blur between like, practical performance, you know, enhancements and self-improvement on the one hand and self-discovery on the other. So when, for most people, after a while it starts to be as much about self-discovery and this like rigorous investigation of who am I and what is true. And, you know, we started the journey in this call by saying, okay, you're not that voice in your head. It's like, oh, okay, if you've If you have thought that's you and suddenly you're learning, oh, that's not me, you know, logical next question is, well, okay, then who, who is me then, right? Who's the I? And then some people go, well, it's my body, right? But you were you when you were, you know, 2 years old and you had a really different body and the body regenerates every like 30 days. And so it's like, okay, maybe I'm not my body. What about my feelings? Well, your feelings change all the time. Okay. And by the way, I keep thinking of the book The Untethered Soul by Michael Singer. He does a really nice job of kind of taking you through this sort of journey of, "Wait, I'm not my body. I'm not my mind. I'm not my feelings.
Well, what am I?" That one is written for entrepreneurs and business people because he kind of logically breaks down the— it's hard to argue with a lot of the logic in the book. Book.
Yeah, Tethered Soul. He has this kind of gross, uh, uh, like image or imagined scene where like the doctors, uh, give you anesthesia and, and yeah, and then, um, anesthesia— sorry, Anastasia is my son's friend's name— anesthesia and basically like remove your body but like keep your, you know, there's machines keeping your brain alive and you have no idea Like, you don't think— you still think you're you even without the body, right? Um, and so, I mean, some way it's the deepest question we can ask, and I think that's the invitation, an invitation of meditation, is, okay, like, who am I really? And that, I think, is a profound question. Um, and even just asking it starts to take you into that beyond the known, the who you thought you were, to these places of either I don't know or these almost like non-conceptual sense of who you are that people, a lot of people will use words like love and God and spirit to encapsulate something that in some way can't really be put into words. It's just like this sense of who you are One way to just think about it is awareness, right? It's like I'm the awareness in which the thoughts and feelings are arising, you know, back to like the listener. And then sometimes you start to realize that that awareness in me or that like sense of self that's been here, like if you think of what hasn't, what's essential, what has not changed since you were born or at least since you were little, it's there like, there's like a sense of self like, I'm in here, right? That has been— that's probably the one thing that's been consistent. And that sense of self is actually the same in all of us. So that often starts to give people a sense of, oh, maybe we are all connected. We are all that same awareness, that same sense of self, you know. And some people, like, I sometimes think of, you know, God or awareness or consciousness looking out at the world through like 8 billion pairs of eyes And there's something about that that I notice I feel sort of uplifted and more connected and like my heart warms when I think about this sense that we're all in a way the same thing or interconnected at a certain level. So that's—
but Dave, Andrew just wants to make his chest bigger. His wife finds him sexy. Yeah. Yes. What would you tell Dave? What would you tell someone?
Nothing sexier than presence. That's what I'll tell you.
That's a good one.
I don't know about that. Like when you talk to me about, I remember saying to you, look, I used to be really drawn by money. I used to be really drawn by sex. What else is out there? And you're like, truth. And I'm like, Dave, that doesn't feel like it's enough. These are not as exciting. I'd much rather have more money than more truth. I'd rather be wrong and have more.
But hold on. Let's, I got a couple, I got a couple of threads for you this Andrew. One thread is why do you want more money?
Okay. Really good question. I will tell you a couple of reasons. Number one, I will say the surface reason is it's more, it's a way of knowing that what I'm doing is right. That matters not just to me.
And why does that matter? What would that be?
We've all decided that this is a thing that's going to matter, number one. And number two, I need a goal of something. And so for some reason, my mind decided that—
Why do you need a goal? What? So when you hit that goal, what's going to happen to you? What's, What's going to take place in your—
It's not about hitting the goal. It's about giving me a reason to keep going.
And why do you need a reason to keep going?
I like living in excitement and there's something really exciting about trying to get to a place.
And why do you want to be excited? What are you trying to get out of that?
There is, I don't know. I get, that's my drug of choice. The excitement.
You feel alive perhaps?
Yes.
Do you feel present? Do you feel there?
He's totally taking time out of my podcast.
I've done this question with everybody and Oftentimes, you took it in a slightly different direction, but a lot of people are like, "Oh, I want money because I have freedom." Well, why do you want freedom? "Well, because I want peace because then I can—" And it's like, well, there are people who are peaceful and free who don't have a lot. It's just a way we've— society broadly, especially the entrepreneurial crew, have told the narrative that this is how they get there. And in some ways, this is a cheat code. And I'm living proof of that for sure, I think, relative to where at one point I thought I needed versus what I did to actually experience the joy, the peace, the aliveness.
Let me take that even a step further, which is aliveness, freedom, peace, and fulfillment, sense of wholeness, which is often what people are chasing, like they're trying to fill some gap or hole. They're always already here now. To me, that's one of the beautiful promises of quote unquote spirituality is recognizing, "Oh, I'm already whole. I'm already fulfilled. I don't actually need anything else. It's already always here." And when, from my experience, when you get still and you start noticing all the thoughts and beliefs that are in the way of recognizing that, then you have the opportunity to see through those thoughts and beliefs, which are just made up your mind just made up. And you can recognize not as a concept, but literally start to feel the most alive you've ever felt, the most joyful, the sense of wholeness that you've been chasing your whole life. It's like the, there's some tale of like a beggar, his whole life is begging, sitting on this chest. And then finally at the end of his life, he's like, This whole life I've been just sitting on this chest, I never looked inside. And he gets up, you know, opens it up, and there's like bars of gold inside. Like, I like that metaphor. Um, there's one other thought coming to mind which relates to it, which I forget if I've mentioned before, this notion of like the Via Negativa, which I really like this idea that— because a lot of people from their ego will be like, okay, it's not about chasing money I just heard from Dave and Jesse, and maybe Andrew's kind of starting to see it, like it's not really about chasing money, it's about chasing spirituality. That's the better thing to chase and attain. And that also is just another ego game. The via negativa is the idea that there's actually nothing to attain. This is back to the like, it's always already here. There's just some things that are in the way, right? One of my favorite quotes is a Rumi quote, like, "Your task is not to seek for love, but to identify all the barriers you've built against it and embrace them." Right? So it's about identifying what is in the way of recognizing who you really are, of kind of realizing who you really are, which is—
Dave, why should I do all this work to realize who I am and to find my current happiness instead of applying all this work to make money, which will give me both things? Yeah, because it won't!
It won't. It's a lie. Yeah, I think a couple thoughts. One is it definitely won't, right? Because how many— I mean, we all know a lot of rich people, the three of us, billionaires and other. And Andrew, of all your rich friends, how many of them seem happy, calm, alive, energized? Content. And how many of them content? How many of them seem neurotic, insecure? Confused, lost, like just a percentage.
I don't know because I tend to see people at their best and usually and I think you do know, I think you do know because you're a pretty good judge of people. I, all right, I'm thinking of one specifically right now who really is in a place where he's making, he sold his company and he's still making money at this current company and he has a lot of a lot of money and he's still now, if anything, it's actually caused a real issue because he doesn't know what to do. He doesn't feel happiness.
I, so I think 80% of the people I know who are worth 8 figures or more are not, would not describe themselves as content, free, alive, happy. I mean, Dave and I went to Penn. We know a million Wall Street people and they all do. I mean, they're better than your typical startup founder if you actually look at their net worth and all that stuff. And I don't know that, you know, maybe 1 in 10 of them is is in some version of that. And so, it just proves the point. And I think the other question, maybe one other simple way to approach it, Andrew, for you, you obviously know Conscious Leadership now, right? Yes. Do you buy into above the line and below the line? I do. So, just for people who don't know Conscious Leadership, above the line is you're open, you're curious, You want to learn, you're playful. That's one state of being. You're present. And there's another state. And you're— well, I was going to get there. Your other state of being is you're closed and you're scared and you feel threatened and you're just not open. And once— the beauty I think of conscious leadership, especially for business people, for me at least, I think a lot, it's like a gateway drug to all this stuff because Dave is talking deep spirituality, right? And even when I started working with him, he wasn't yet that as spiritual as he is now probably. And it was like, Okay, this is like a gateway drug. So would you like to be more open, more curious, less reactive, more, more likely to respond? Would you like to be more in play? Like all those things above the line and below the line is just a, is a thoughtful way of saying present versus not present or soul versus ego. And so if you think of it like that, like the benefits, Andrew, for someone just very practically is I think if you meditate more often, you will be above the line more often. Because again, when you close your eyes and you have a thought and you go, oh, I forgot to take out the trash. Yeah. And then you go, oh, I'm an idiot. Why do I always forget to take out the trash? And then you like go through this thing or you go, I take out the trash and then it just passes by. That's what happens when you're meditating. But then in real life, somebody says something to you or something happens and, and you typical thing for most humans is just to quickly go below the line. Oh, he said he doesn't like my shirt. Oh man. Why don't I dress well? Or fuck him. Like, That's typically what happens. But all of a sudden, when you meditate a lot, you just kind of go, "Oh, he said he doesn't like my shirt. Okay." Or, "I disagree with your idea.
I don't think that's a good idea. I don't think we should do XYZ." Even more common for founders and leaders in business, it's like, "Oh, no." We tend to take it personal. It's a threat. They're attacking me versus, "Oh, you disagree. Oh, tell me your thoughts." Genuine curiosity.
I tend to disconnect and then I think about it later.
But a lot of people withdraw. Dave, what did you say? That's a below the line move.
Oh really? To disconnect is a below the line move?
Withdraw. Yeah. Oh, I'm threatened. I'm going to withdraw. I'll fire and fly, right?
And then I'll come back and deal with it later. But you're saying that's also below the line.
Well, are you, are you in that moment, are you open, loving, learning, willing to, willing to learn? Commit, playful. Are you those things? Or are you close?
I'm willing to procrastinate it and let it happen.
And then I'll think about it later. You could disconnect from above the line if you're making a conscious choice. Oh, I'd like to kind of take some time. I think what you're describing is a flight reaction of like, oh, this is too intense. I don't want to be with this. No, you know what it is?
It's, it's not killing me. Let's just let it happen. And then I, I will sit with it for a bit and come back. I'm thinking about like a conversation we had, Jesse and me on Wednesday. And I was looking even, Jesse, at like how much talking you were doing and how much I was doing. And I realized the more you were doing, the more you can see actually in the Grain.com tool that I was doing less. And I think it's— I'm just like, all right, let him go and then come back and reanalyze. And maybe the better way to have done it would be to say, Jesse, I'm curious about why you have this point of view. It's different for me. Maybe there is a misunderstanding. Vernon just said that we're not hearing each other.
So maybe that's the funny thing about that conflict was it was a massive misunderstanding. Yeah. But, but no, I mean, I think you, today's point, you could, you, I, I think in that moment you were threatened cuz I was getting excited and heated and you were like, all right, I'm gonna pull back from this versus, um, hey Jesse, like I think something's misfiring. I would like to take a, a 5-minute beat. That's like, like what Dave's saying. Again, it's all about response versus react and response is something that you actually create, you choose versus react is just. I'm just going to do this without thinking.
All right, so here's where it's the most heated, more even than work. I saw, Dave, you're gearing up to something, but let me say this. A friend of mine came over the other day. He told me he's going through a divorce, and I go, wow, this is bad. He goes, yeah, I asked my wife, is there anything we could do at this point to bring it back? And she said, no, that's it. We've gone beyond the point of no return. And he said, and when I asked him why, he said, every time we'd get into a conversation, things would trigger us. And we would just say— I would take it as the worst possible reaction, and then only later I go, that's not what she meant. And he said, I couldn't pull it back in that moment. And so what do you do in a moment where you're so heated before you even have a chance to think, you say something?
Well, I think what came to mind, it was the, the sacred pause between stimulus and response. And, you know, Jesse keeps alluding to react versus respond. It's all the same point. In some way, you can think of meditation as building that muscle of being able to be aware enough in the moment to pause and then choose your response rather than just react. And, you know, if we're especially in relationships, most of the time we're not actually responding— this is back to presence— to what the person is saying. We're reacting to some past experience we had probably 30, 40 years ago that this reminds us of. So we're like superimposing the past onto the present and then reacting to our mom or dad or, you know, teacher. Um, and so it's like we're just replaying out our trauma, you know, in the current relationship instead of noticing, oh, I'm about to react really disproportionately to this actual situation. Oh, this must be something from the past for me to go, you know, get curious about and heal. And that's a really different way, you know, in my experience, in my view, relationships at their best are both people using the way they trigger each other to recognize the unhealed traumas and patterns and heal them and grow through the relationship. But what most people do in relationship is they just play out the old trauma patterns with each other until it's just untenable anymore, which is kind of what you're—
yeah. And, and I think being— I mean, Andrew, I think there's a case in point of your question is, again, back to meditation, like the benefits of it is you, you are likely to be less reactive to everything, to your spouse, because you're just used to seeing thoughts go through your brain and not having to react. And part of it is one of the crazy things I was a big thinker and again, like once you know you can have a thought and not actually react to it in your brain, then it like, you can, you realize you can do it everywhere. Like with our kids, one of the funny things that like difference between Dee and I, I was like, they say a lot and I just like, like they just say some stuff. Like they talk back sometimes and it's like, you don't have to respond to that. And when you don't, it, the whole thing disappears. Right. That's how thoughts are too. Yeah.
And the point I hear you making Jesse is whether they're your thoughts or other people's thoughts, you can treat them the same.
You like, you Once you know that, it's very powerful because you just, you end up being less reactive to everything. And again, in the, in the just like super pragmatic version of why meditation, and you could read the science again, the brain, like Ray Dalio talks about it and Seinfeld talk. I mean, there's all the, there's plenty of evidence out there for those who want to be scientific and just very pragmatic. And of course the spiritual part of it, I think, as Dave Kashen said, is even more in my, my experience, even more invigorating and alive.
I had two other thoughts. One is around resilience, which is especially for founders, right? What's more important than resilience, right? It's just like constantly facing setbacks and challenges. From my experience, the more you're doing that, the more you're meditating, the more you're able to bounce back more quickly because you don't believe— you don't go down the downward spiral that most people do of like, oh God, this thing happened. Extrapolate that into the future. It's going to be terrible. I'm terrible, right? You just see it for what it is. Okay, this was a setback. What, you know, what's my desired future state? Like, you can just stay present and move toward the future you want instead of like, you know, spinning out of control. But there was Joe Hudson, another coach, interviewed Sam Altman about meditation, and Sam was saying, yeah, I just thought it was, you know, just kind of a waste of time, bunch of BS. And he was describing just how much it was like a superpower it gave him to be resilient, not get reactive in the same way, just see things more for what they are, be more playful about it. So— Dave, what would you—
to your coaches, you've coached all these famous founders. When they come to you and they go, "How do I start meditating? What do I do? Okay, fine, you've convinced me," because we spent a lot of time on that part, but How would you— what do you actually tell people to do? Yeah, so the simplest—
there's a couple really simple versions. The simplest thing to do is set a timer for 5 or 10 minutes and focus on your breath, and more specifically, either notice your belly expanding and contracting as you breathe, or notice the air coming in and out of your nostrils. And what will naturally happen is at some point you will stop focusing on that and your attention will get hooked by a thought. No problem. When you notice that that has occurred, bring your attention back to your breath, i.e., your belly or the air coming in and out of your nostrils. That's the most basic practice. And it's not— what people get confused by, because so many people are like, I'm bad at meditating. It's not that you're supposed to stay focused on your breath for 10 straight minutes. The practice is just the noticing, right? It's a mindfulness, just noticing, oh, you know, by having the intention to focus on your breath, you notice when your attention has drifted and then you just gently bring it back. I like the metaphor of like training a puppy. It's like, oh yeah, it went off. Okay, come on back, right? You don't go make yourself wrong. It's not, you're not doing it wrong. And if you literally, you know, have 9 and a half minutes of just, just focusing on different thoughts, but, you know, one time you notice that that's occurring and bring your attention back to the breath, that's useful, right? That's the practice. In some way, it's like if it was— if there was a muscle to build, it's the muscle of exerting conscious choice around where you put your attention.
The one, I mean, you told me this, I think, Dave, but I use this app called Waking Up, which is, again, it's the same thing. He just, it's a little more guided for those who really like, Andrew, I know you want structure and whatever. And it's like, he starts with a 35-day program. It starts really like 4 minutes, then 6 minutes. And, you know, he's talking a little bit, which is helpful and kind of helping you get into it. And then he just has a daily meditation, which I did for probably 3 years. And then I've started experimenting with new different modalities and different versions of it, because there are also different— there's lots of different modalities of it.
Yeah, Waking Up is Sam Harris's app. He's great. There's also Insight Timer. It's almost like the Netflix of meditation in, in the sense— well, I mean, it's free, so it's different, but in the sense it's, you know, thousands and thousands of different guided meditations to choose from. So you can experiment They also have just a, you know, a nice timer with a nice bell. But I will sometimes just, just try different, you know, guided meditations. Like, I think of it more as just experimenting and seeing what affects you and how. So I like trying some of their different meditations that I thought I just had almost, almost like full circle back to like spirituality and religion. One of the things I appreciate about what I'll call spirituality versus religion is this distinction of sort of like mythicism versus mysticism, right? In many religions, there's a number of myths or stories that, in my view, are sort of allegories or sometimes metaph— like, they're useful, they can be useful, But a lot of people relate to them as like, I must believe these stories that some human wrote down at some point. And I'm not, I'm not trying to— there are people who believe them. I'm not judging that. For me, it has felt a lot more powerful to directly experience something than to believe a story that, you know, somebody else wrote. And so that in some way, for me, spirituality is just like this practice of like really looking at my direct experience of what's, what's occurring. Um, it's almost like the opposite of mythicism. It's like, if I let go of believing all the things that I've been believing, what do I directly experience, right? And identity— our identity is itself a thought. So, if I even let go of that, of this thought that I'm this Dave Kashen guy with this history, and if I even let go of that thought, what do I directly experience? For me, that's been the path to what I call and people call spirituality. It's a sense of like, what's here when I let go of all the stories and all the thoughts? What's left over? And there is, I don't want to say something, but there, I experience an experience when I no longer am thinking and my mind does go quiet. And there's something that feels really profound about having that experience. And there's a depth of peace and aliveness and love that I feel that because I've sort of touched that through meditation, I have that touchstone and I can kind of bring it with me into my everyday more and more. So the more I meditate, the fine— I find the more I'm able to come from these states of presence and love when I'm interacting with people. And that to me is a real, uh, benefit to going to the meditation gym, as you say, Andrew.
Let's close it out with a couple of other things that Jesse, you included in the newsletter. It was meditation, but it was more than meditation to get to that spiritual place for you.
What else did I include?
The gratitude journal. And you actually— I like gratitude journals. A lot of people have them. I actually prefer what you do beyond the gratitude journal, where you will on Friday— today we happen to be recording on a Friday— you will send gratitude to people directly. And I've been doing that and it, and at first it felt really weird, but that's a way for me to super feel the gratitude. And then also it has it like a bounce back effect where the other person reacts and then it feels even better. I feel douchey at first, but then I feel great.
Yeah. Isn't it sad by the way? Like I also had that experience in the beginning of like, you feel kind of like weird or fake. And I think a lot of, and it's like, damn, why is that? Like that kind of sad that we, we live in a, you know, like that. Have you guys seen this meme that's going around TikTok of like call your buddy to say good night? Oh dude, it's so funny. Like, really? Big Boi called Xzibit. Like, rappers are calling each other and it's literally like they'll have their phone on and he's like, it's like, yo, Dave, man, I just want to tell you good night, dude. Sweet dreams. And the other guy on the other side is like, he's like, what? What the hell are you talking about? He's like, what the fuck? Are you drunk? Like, it's so funny. But it's— you guys got to look, go search it on TikTok or Reels. It's like a hilarious meme. I was like, I want to do it. My younger brother and I were like, let's do it to our older brother because he's similar, right? And but yeah, I think, you know, these things do require, like anything, intention. Like I try to do it on Friday afternoons. But Andrew, the funny thing is it generally leads to me just doing it more often without prompting myself to do it. And then, yeah, the gratitude journal. I mean, again, the way it's been explained to me, the science way is our brains are designed for survival. We're designed to scan for threat. Most people I know, including me for many, many years, would wake up and the first thing I would do would be like, oh, let me look at this dashboard. Let me look at my email. Like, what's wrong? What do I need to address? Because I'm— I want to stay alive. Like, and, and that's not true. If you wake up actually, oh, living in a nice house, sleeping next to a beautiful, wonderful wife, you have like— you're going to eat in the morning. Like, and so if you don't actually shift, if you don't take that time to intentionally show yourself what is good, you won't even be at neutral. And like, gratitude journal just gets you to neutral. It doesn't even get you— forget about feeling positive. It's just, it just the natural tendency of your survival brain, it, it just curbs it in the other direction.
And I want to share one other thought that keeps coming up around, um, like we've all heard the term unconditional love, right? We all, you know, it's like, oh, I want to be, I want to be loved unconditionally. I Can you love yourself unconditionally? You love your kids unconditionally. In, in some way, I relate to, uh, like spirituality as unconditional love, like spirit loves unconditionally. Or the way I really think about it is we are unconditional love at our essence. That's not like capital T true, but those words have meaning for me. So Or maybe you could even just say love is unconditional by its nature. Like, there really isn't conditional love. That's not— that's manipulation. That's something else. So if love is unconditional by its nature, and we— I think we are love at our essence, but even, even if you don't feel that or believe that, if we want to be loving, then the journey— which most people want to be loving— The journey is from living conditionally to living unconditionally, right? And our mind is very conditioned. Our mind says, "That's good, that's bad," you know? And so if we listen to our mind all the time, we're living conditionally, right? Bad, bad, bad, bad, bad. I can, you know, I can be happy when this happens, but not when this happens, right? Those are all the conditions. And so in some way, meditation allows us to release all those conditions that our mind puts on life for what has to be true to feel loving and peaceful and joyful. And I think that's, in some way, that's enlightenment, is like releasing all the conditions so I can accept and allow everything to be exactly as it is and live unconditionally.
Sometimes I want those conditions. Sometimes I feel like if I put the conditions, I will only be happy if, then I will work harder to do it. But then I also think about the newsletter issue that Jesse wrote where he basically said the same thing to you and you you told him, all right, then try doing nothing and see what happens. Stay at home, watch Netflix, see if that actually continues or if there's a different drive that doesn't need you to feel the pressure to get there.
Well, all right, it's just a self-referential trap. I just want to be clear. Okay, I need my pain, I need the conditions because if I don't believe that having all this money will make me happy, then I won't be driven to make all this money and therefore I won't be happy. Right. It's, it's like this self-referential loop we get stuck in. So. All right, go ahead. It's not— it doesn't mean you can't make lots of money if you're peaceful and happy and fulfilled. It's just you're doing it from a really different place where it's more fun.
And then maybe because it's more fun, then you want to do it more and then that builds on itself. Yeah.
I think one thing Dave Kashen said to me early on in this journey, we can close out with this, is is like, this is not a should. Like most people, again, smart people here is like, you should do it this way. And it's just like, no, like being fear-driven or the game you play with yourself, Andrew, where you set goals, that's great. It can be highly effective. Like it will make you money potentially, potentially even more. Like that was a big trade-off for me. It was like, Dave was like, will you be willing to see that if you just like were old Jesse, you would be more successful? And I'm like, yeah. And then still do you want to choose this other path? And just because I want to, because I want to live a certain way, But I don't think you have to choose this. I think you can be very effective from below the line, from using fear, from using dirty fuel. Lots of people are. Look at— you wanted to talk about Trump and Musk. Like, those guys are crushing it by certain standards. And then they, you know, they're petulant children on Twitter with each other. So, you know, there's just no— you don't have to force it one way or the other. I think these are all choices.
Yeah, I agree. And to me, like, the, the tragedy is when we place a lower order value above a higher order value, right? Like, I had a mentor once who said there's nothing wrong with, like, marrying for money, but if you're marrying for money over marrying for love, it's just sort of tragic because love is actually more valuable than money. And I think that's a useful way to think. It's not wrong or bad, but I invite people to reflect honestly of like, is that actually more valuable to me than this other thing that I'm trading off?
All right, let's end it there. We'll continue. I'll continue being— actually, you know what, it's not that I'm skeptical. I think it comes across that way, but I do want to bring up all the objections that are in my head that will then later surface up. And sometimes people will say, you brought up the same thing that I was thinking. So I'm glad to hear that. Let me know what you're all thinking about this. Thanks, Jesse. All right.
Thanks, Dave. All right. Bye guys.
