Is Money the Secret to Entrepreneurial Fulfillment?

Welcome to Heart of Entrepreneurship, where me, Jesse Pujji, and Dave Kashen talk about building businesses from a place of heart, from a place of love, from expansiveness, and we challenge the notion that success requires suffering. Yeah. All right, let's do it. All right, I'm gonna start with a story that involves me and you, um, So I think it was 2019 and we were, we were coaching. I actually, I asked you a question. I said, if you were to try to like have the most impact on someone's life as a coach in the shortest period of time, what would you do? And your answer was like, every person holds 1 to 3 really core beliefs. So I would like, I would like quickly try to drill down by asking them what they fear and why they fear and just keep saying, why do you fear that? Why do you fear that?

Which ultimately brings you down to to someone's core, core thing.

And then I would try to get them to be the opposite of that belief was just as true as the belief they held. Not to change it necessarily, but just to— once you see the opposite, you're like, oh, I guess mine can't be as true as I thought it was when the opposite was to be true.

I was so wise back then. That was a good answer.

And we did this exercise, and as we did it, we realized one of my core beliefs was money equals security or safety.

Mm.

And then we were in my office in San Francisco and you were like, Jesse, can you see that money— there's people who have less money than you who are more safe than you. And I'm like, yes, intellectually I can.

And you're like, well, you feel more safe.

Yeah. Who feel more safe? And I was like, yeah. But like, he's like, can you see that you could lose all your money that you have and you would feel just as safe? And I was like, no, I can't. There's no way I can do that. And then we negotiated and you got me to agree that like incrementally more money than I had made up until that point would not make me feel more safe. And I could, I could get on board with that. And I think generally I, that was actually pretty life-changing for me. I've told people that story because there were so many ways I made decisions, which just the simple, really underneath the bottom of my operating system, core to my code was more money will make me more safe. And it wasn't conscious at all. It was just this like, and that once that went away after that coaching, you know, we did that coaching, it was like, oh, I could like just think a little bit more clearly about what do I actually want if that's, if I've let go of that belief. Now I would tell you that I still don't, I still am probably not willing to do the other one.

You could lose it.

Um, but anyway, that, that's the story. So the topic of today, which I have not told Dave, as I'm, I like to do is I wanna talk about money.

I wasn't sure if you were going to money or limiting beliefs. Both are fun.

Yeah. I think money, you and I both have our own interesting relationships with it and attachments around it.

Yes.

I think for most entrepreneurs, there's some who don't, it really doesn't, but they're very few and far between. Most, and rightly so, it's like, "Yeah, I want to do well and I want to have freedom and all that stuff." I mean, there's even a quote I sent a friend of mine today who was He was going through one of the grind parts of entrepreneurship and I sent him the quote that entrepreneurship is choosing to live your life a few years like most won't so you can live the rest of your life like most can't. So, there's even this like, "If I do it, then I'll be—" So, I think this is relevant to most people listening. And so, I don't have any others. Well, I'm sure I'll have lots of questions. I like it.

But that's the first starting point. I'm forgetting his name now, but a guy we're wanting to bring on the podcast that had some tweet that was like, basically, like, keep your chip on your shoulder until you've made it. You know, make sure not to like let it go before that, which is kind of coming from that same place of like—

I mean, there's a, there's a saying, chips on shoulders put chips in pockets. Yes. So that's a direct sort of—

yeah, relates, right? If money is safety, well, I bet I need my pain, my insecurity in order to drive me to get the money to be safe. Uh, well, so much to say about money. Uh, yeah, acknowledge what a challenge it's been for me over the years. I think for me it's been more about, you know, if you think about the big three sort of, um, needs, or, uh, yeah, I guess needs that we often perceive as unmet are security, safety, uh, freedom and worthiness. Or we saw that— security, control, approval. I'm using those synonymously. So I think people map all money onto all three and vice versa. So mine, I think, was less about safety and more about freedom and worthiness, and with a heavy emphasis on worthiness.

Freedom— sorry, freedom is the parallel of control.

Yeah, it's like, okay, yeah, when people say I want control Basically, it's like, I want to be able to do anything that I want, which is freedom. I'm just putting those together. And approval.

Can you just sidebar for a quick second on the security control and approval thing? Because I don't know that we've ever fully—

Sure. I mean, I learned this from the Conscious Leadership Group that I think we've talked a lot about above and below the line. Are you in a state of presence or in a state of threat? Well, the core 3 sort of aspects that that tend to feel threatened for human beings are sense of safety, right? That's sort of obvious, right? You know, if there's danger, if there's— but it's even like safety slash security. And I think that's where it gets interesting because most of us don't really think that losing some money would mean I'm physically not safe, but my sense of security, like this sense of like, I'm okay, I'm gonna be okay, my family's gonna be okay, right?

So security, and especially future-preserved insecurity, I think, like, or like a lot when you're, oh my God, if this happens in the future, something bad Totally.

So, that's security and safety. Number 2 is control or freedom. So, silly example is like the Wi-Fi goes out and it's like, "Argh, I had a plan. Something I was trying to do. I wanted to control life a certain way and then it got thwarted." So, that's a threat to my sense of control. And there's all versions, there's lots and lots of um, setbacks and challenges that come up for humans, for founders, in their, their sense of their ability to control and make what they want to have happen happen. Um, and it correlates to freedom because it's sort of like, if I could control life and, and make anything I wanted happen, then I'd be totally free, is sort of the, the, the myth, I'll say. And then the third is, um, approval and worthiness. So approval tends to be a little more external-seeking, like, um, wanting validation, wanting external approval. Worthiness is sort of the internal version of it. They're highly related, like just a sense that I am worthy, I'm valuable as a human being.

And, and there was a period, by the way, where we were coaching— I want to say it was like '21 and '22— where Every time we coach, I don't know if you did this on purpose or not. I think you did. It was like, basically no matter what my issue was, we, we found how they fit into one of those 3 buckets. Yeah.

With, that's right. I'd say which 1, 2, or 3 of these feel threatened by this situation? And it's a useful self-reflection to see, oh yeah, this is threatening my sense of security or my sense of control or my sense of approval.

It's also, I would also just add that one of the benefits I found of it is like I think we, you know, I think, did you say that like people think they have like 100 different problems, but they kind of have like the same one problem or two or three problems. Yes. Dress themselves up differently. And it was that when we did it for a couple of years, it was like, oh wow. No matter what I thought the issue, I don't know what to do next with my life. Should I raise money or not raise money? Like they were all variations on one of those three. And then it just became more easy for me from a self-awareness to kind of go in the moment. I'm like, Wait, which one is it? Like, yeah, my wife, it's like, funny look. What, what, what is that? That's not— it's not my wife gave me a funny look. It's like, oh, I'm feeling she's not approving of, you know.

Yeah, it's a way to like quickly boil it down to its essence. Like, what is this really about for me? Okay, it's about my sense of security. It's about my sense of control. It's about my sense of approval. And, um, to your point about one issue, it's really all about safety and security. It's just that like, especially when we were living in tribes, right? Like, our ability— like, if, if our safety was threatened, well, we needed to be able to control, right? Like, and be— and dominate and be the powerful one so that we didn't get killed. And then again, because we're in tribes, approval meant safety, right? If the tribe didn't like you and they kicked you out, you were— you're dead. So they all ultimately stem out of safety and security.

Money makes sense. I think, I guess we may say, coming back to money for a second, that you said money hits all three. I think maybe said differently, we use money as an object to create a feeling of insecurity, lack of control, or lack of approval for ourselves. Money is a commonly used—

Yes, for your system to perceive threats, right? Um, yeah, I mean, it's interesting if you just kind of get really simple for a second. What is money, right? Like, we, we, you know, for a long time there was no money. There was nothing, you know. There was trade. And then at some point someone said, oh, what if we had like a third thing, like a currency, that instead of having to find the person who needs their, you know, molond and match them with the person who needs their haircut, which is a very hard permutation. What if we had this third thing that was like currency, and I could give it to you to mow my lawn, and then you could give it to someone else to cut your hair? Oh, that's a way more efficient system. I mean, we just made it up as a way to facilitate exchange. Um, and so this thing, we— in some way, because it's made up, it's, it's almost easier for us to just project all sorts of things onto it that it doesn't mean, right? We give it meaning that it doesn't have. Now, I don't want to like pretend that it doesn't matter and doesn't affect these things, because gosh, if you need, you know, a, um, major, you know, surgery and you have no insurance and no money, you might not be able to get it, and your life might be, um, at risk. You might die. Whereas someone else who has lots of money might live. So there are very real ways that money can be a source of security and safety, um, in some way freedom, because obviously you can— the, the set of things that you can do is greater when you have money, at least the set of things that cost money, right? Vacations and buying certain things, etc. Um, and then certainly we live in a society where people do tend to attribute worthiness to money. And so they do tend to approve of— I mean, sometimes they're jealous and disapprove, but tend to approve of people and ascribe more value. Oh, Elon Musk, oh my God, he's such a more valuable human than all the rest of us. Um, and so it, it's not like it's without connection to reality, but there's a way that we, um, make it mean something bigger than what it actually means. Most of the time, that's not really what we're experiencing is like, oh, I'm scared I don't have enough money to get a heart transplant if I need it, right? It's more this vague sense of like money equals security, and I can't feel— and I think this is important because these are all really feelings that it boils down to— I can't feel safe unless and until I have a certain amount of money. And by the way, it's, you know, we've talked about this idea of like, you know, hedonic treadmill, or we could maybe map— yeah, create another version like security treadmill.

Right. Yeah. It's interesting. You, I mean, the approval control and security are things just to make sure, like, they're things that we tend to source from outside versus inside. Right. And then money in some ways is like the ultimate cheat and hack because it gives you all, you just said it, it gives you all three purportedly. Right.

Right.

And right.

Yeah. It's like the, It's like this very tricky illusion that's very hard to see through because it does feel like money can give you security and freedom and worthiness. So, it's like, wow, does it make sense how much we want it?

And almost, I mean, just to pause there, is there anything else that gives you all that has the reputation of giving you like, you could have an attractive spouse or you could have—

Dave Kashen. I think for some people, like a boyfriend, girlfriend, spouse, I think they project onto that safety, maybe, uh, maybe not control. Control in the sense of like, I imagine getting married one day and having a family, and so if I get— if I get the— my— if I find my person, then I'll have controlled, you know, my future the way I want.

Yeah, so maybe success kind, but like, it may be that it's one of the things that makes it unique is it's one of the few things that really— the story that the world tells is that those— that it gives you all three of the biggest human needs.

Well, what's interesting, that's just coming to my mind in this moment, is it's, it's also infinite, which— it's interesting, like, it's not real, so it's infinite. So there's a way in which it's a really easy thing for the ego to use as the, like, I need more of that, right? So if the ego believes in scarcity, it's really easy to be like, I don't have enough money because how much do I need? More, right? Like, I, I joke to my, um, wife often that, like, there's a formula for how many, um, pairs of skis and bikes you need, and the formula is n 1, where n is the number you have now. And that's kind of how we are. It's just, yeah, same for shoes. Um, and it's kind of how we are with money. It's like, you know, there's a lot of—

you know where my head's going right now? This is interesting. Like, we've— this is some Dave Kashen insider stuff. We've been talking a lot late recently because of Joe Hudson of how rather— like, when you have natural desires, whether they be love, success, or sexual, or whatever they are, he suggests that— and actually, I was like looking at the Sikh scriptures and they have a very similar orientation of like You have to follow them. That's part of your karma. Like your authentic wants, your authentic wants. We tend to have like, I've gone through this like, oh, I shouldn't want money and I tend to resist it. And then you get stuck in this place versus if you actually chase it, you will find over time that it's not— it's hollow. But the reason this came up around lust and I was like redoing all this ChatGPT stuff with scriptures, it's like what you're actually feeling is your desire for God or for the one or for the universe and the infinite state. Well, that's when you said infinite. My mind went, oh, maybe money also. It's the closest, like, I'm not, I don't want to like offend anyone, including myself, but like, it actually does share a lot of properties with God, with the universe. Infinite. It's the only other thing also that gives you all those three things, by the way. Interesting. If you have God in your life, you have like, you know, you don't, or they're the inside. It's almost maybe the perfect opposite of the inner versus the outer.

That's interesting.

Control and approval. I don't know. It's interesting.

Maybe that's why the, like, thou shalt not pray to false idols was like such a core principle, right? It's like the idol is, you know, we pray to the god of money.

I mean, it tends to be a lot of, especially, I mean, you and I know a ton of founders, including myself, like it tends to be one of the most sought after things. It's also the biggest empty disappointment when you, when it finally hits and like you were, you were going to the hedonic treadmill, but a lot of people end up going, well, I just must need more. Yeah, exactly.

Right, that's the most common. Okay, I thought if I had whatever, a million, I'd feel it. Okay, I must need 10. I thought if I had 10, okay, I must need 50. You know, and then that's— that is the treadmill. It's like a drug. It's like, oh, the amount I thought I needed no longer or doesn't actually fulfill the hole, and therefore I must just need more and more and more and more. And that's the trap. And I, I want to I like where you were going to around sourcing security control and approval from outside versus inside. I think it may be even more precise way to say it is letting go of the belief that there's any lack of security control and approval. Because if you get fully present and you really get curious, generally you can find that in this now moment there is no lack of security, no lack of control, no lack of approval. Yeah, right. There's nothing missing or lacking. And that's the whole ego game, is this sense of lack. And that these are the ways that it expresses it, right? Oh, I'm— I don't have— I don't have enough, or I'm not safe, right? You know, and it's, um, like, it's sort of a, you know, security is in some way the easiest one. If you— if you can't leave the present moment right? Like, if you couldn't leave your attention from the present moment, like, you are safe. Like, in this now moment, you're okay, you're alive. Even if in the next moment, you know, you're gonna get, I don't know, shot or run over, you know, whatever is going to happen, like, in this moment, you're totally fine. And then in the next moment, um, even if you died, like, in— then you'd be dead, right? So You find out what it's only getting slightly ahead of yourself or slightly behind your—

like there's some example. I don't know if you said it was like you're torturing someone. Like if you poke them with something, like in the moment you're feeling pain, you're feeling pain, then you stop feeling pain. And the thing that makes it so scary is like you're the anticipation moment for remembering what just happened. It's not the actual thing in that moment. So what, so if you had a client, and I'm sure you have lots of clients who walk in and they're like, I've made $100 million, Dave, and I still feel empty, scared, not enough.

Unfulfilled, not whole. Yeah. Yeah. What—

how do you coach that person? How would you coach them? How do you coach them?

Uh, hold on. I'm tuning. I'm imagining that scenario. Um, I'd probably take it one of two ways. Um, one is as an opportunity for them to see that the stories that their mind makes up are not true. Like, okay, like, what had you believe that you would feel fulfilled and whole once you made this money? And they'll generally see, well, I just, I had, I had the thought that that was it, and start to just unravel the mind, frankly. Like, like, one of the biggest, um, causes of suffering is that it's not that we— the issue is not that we have a mind or a voice in our head or whatever you want to call it, is that we believe it, right? Right? So, so that would be one path is like, what else does your mind say that you're believing, and what's the impact of that on you? And that ultimately leads to the core, core belief, which is whatever comes after the words 'I am.' Hmm. Is this like core identity level belief? Oh, I am this, I am that. I'm— and, um, you know, I've done some workshops where we really look at identity And the conclusion is anything after the words 'I am' is just made up, right? It's just a concept. And the, the deeper truth is simply 'I am,' right? And that's sort of conceptual too, but if you can feel the same in the Old Testament too, isn't it? Yes. Isn't that the name? I am that I am. Um, it's quite profound. And what I like about Like, I had heard that before and it just sounded kind of like spiritual or religious, like mumbo jumbo. But there's something— mumbo jumbo, yeah— there's something about the just looking at what you actually say. I am the— I am a husband, I'm a father, I'm an entrepreneur, I am, I am a millionaire, I'm a billionaire, right? It's like, it's not I have— let's just, since we're on the topic of money, it's gen— it's not— it's often not like I have a million dollars, it's I am a millionaire, right? Or I have a billion, I am a billionaire. It's like That's an identity level. That's who I am. I'm a billionaire. Like, yeah. And so that's interesting.

Some people like, I think, uh, Dustin Moskowitz has— he's like pretty— he writes a lot about how he's the steward of, like, he thinks of himself as the steward of the—

right. That's a very different experience. Yeah. It's like, oh, this, this is flowing through me. Well, you know, how do I want to steward it? So where that then leads is when you're I mean, this is deep, so I wouldn't probably go there in the first session, but just since my— we're talking about this basically, you're saying, what do you do with someone who already has all the money and is like, shit, I didn't find— I got to the top of the mountain, I thought peace, inner peace would be there, it's not, what do I do? Um, essentially it's a self-discovery process that leads to the realization that you are already whole. And like, the I Am, who you really are, you know, behind all the stories and concepts, is already whole and complete and worthy and free and safe.

And how does someone get there?

Like, um, I'm a big fan of what I have heard called the Via Negativa, which is, uh about removing what's in the way. Like, similarly, for a similar reason, one of my favorite quotes is the Rumi quote, like, our task is not to seek for love but to remove the— identify the barriers we've built against it. That, like, what's true is true, right? It's always true. It's just that we have a number of layers of beliefs and patterns that obscure us from experiencing the truth, including us, and especially the human mind, the ego mind, the voice in our head that we tend to identify with and as, and, and it itself creates like an identity, right? Yep.

Um, and so, so try to figure out the things that are blocking you from knowing your whole— yes, could be stories, mostly stories or beliefs.

Figure out, feel a little off, but yeah, ultimately, yes, identify, try to understand. Yeah, understand, um, what's in the way Um, you know, there's some modalities like to look at, well, where did that come from? It can be useful to realize, oh, when I was 7, this thing happened and I made up a story that I was unworthy, and so of course I'm seeking worthiness, you know, or, um, which was my experience. And, um, so yeah, there are beliefs and basically defense patterns that get in the way. Like, I really like, um, Joe Hudson often uses the notion of like living undefended. I think there's a connection between, you know, it's like the ego, the, the personality, they're all just defense mechanisms. And as you remove those defense layers, what's left over is— I call it love. It's essence. It's, um, I am-ness. Yeah, I am. It's, you know, that's why there's the, the—

it's interesting, right? Like the, the when you and I have done versions of this, it was like help. It was helpful.

Can I interrupt for one second? Yeah. Um, because I'm just mindful of this could all just be like, oh great, those are some more concepts that for the mind, you know, like my, you know. And so what I just want to say, I think is really important, is it's not about even— it's not about understanding, it's about directly experiencing that sense, right? Um, like, I'll ask my clients sometimes, like, just for now, could you relax as the one that is beyond wanting approval, security, and control? Which I think comes from the Sedona Method. Yep. So, and if they can, they'll viscerally feel like, oh wow, there's some— there's something in my being that already feels safe and free and worthy. So, I no longer believe the lie that I have to attain anything in order to experience that.

Yeah, yeah, yeah, that makes a lot of sense. And I mean, back to the story at the top I told, like, intellectually I could understand that there were people who had less money than me who felt safer. And then it was like, let's try to feel that and agree to that. And I was like, oh, like, no, the idea— and, you know, it's like losing money, losing what I had would feel like a threat to my safety and security. And to your point, it's about feelings, right? It's about what it actually feels like in your body and the sensations. It's not actually about what your brain tells you necessarily. Or it's easy to get caught up in another mind trick of yourself versus to actually drop in and—

Right. I should believe this, you know, yeah. Versus actually feel that felt sense of, wow, I am safe. And, you know, I try my absolute best to support people to have these shifts. And sometimes, um, life is just more effective than, you know, probably most of the time, than me, you know, or then, right, like you can try to pre, you know, sort of an ounce of prevention, right? You can try to prevent, um, the experience of, let's say you know, extreme reaction to a loss of money, you can try, right, by unhooking the belief that money is security, by feeling your own sense of safety. I suspect very, very spiritual people could lose lots of money and, you know, wouldn't, you know, wouldn't bother them at all. For most of us humans, um, it might take losing a bunch of money, and that was my experience, and I've shared this. Yeah, you want to talk about it? Yeah, yeah, I mean It was, God, was it '21? I think it was '21. Um, I was kind of riding high. Uh, I think tech was still doing well despite COVID. Crypto was up. I had a bunch of, um, Solana that very gratefully received from, from coaching, uh, Anatoly. And, um, so I was like, oh, I'm, I, you know, hit my number. Like I'm sitting pretty. And within like And my buddy said, you know, I think it was end of '20 or end of '21. He's like, I feel like things are really frothy. Like, I'm going to sell everything. And I'm like, I don't know, maybe, and kind of ignored it. And then within weeks, I think it was weeks, maybe a few months, like dramatic crash in tech stocks and crypto. Many remember that. And so I think I lost like 70% of my paper worth. Like, like massive amount. And I, um, like, I was hard to breathe. I was, I was like ashamed. I think I was mostly ashamed. Like, I thought I was smart, you know? I thought it was smart. I've worked for an amazing hedge fund. I've made great investment. Like, like, I think it mostly hit my identity as a smart person almost more than the— I mean, it was both. Is that approval, control, or security? Approval, worthiness. Yeah. Um, although identity-level stuff can feel like security too, like, oh wait, who am I if I'm not smart? Um, and also it was controlled because it was like, I thought I was at this place in my life and like the next 10 years were going to look like this, or 50 years, but now I'm at this other clearly way worse place, and so now it's going to be harder and struggle and I can't believe how stupid I was and like, why didn't I sell? All that. But so there's all those thoughts. But like, I was, you know, like punched in the gut, like hard to breathe, hard to be present. I remember we were away up at, up at the lake, um, in this like cabin with friends, and I just couldn't even like interact with them. I was— must have been so annoying. I just kept talking about it. And, um, and then what I I'll tell you what I did. Like I went for—

and just hold on before, before we keep going. Like, and you've been like meditating and being a coach and trying to find your zen for a decade at that point.

Yes. You've done— that's a great point. It's not like I was— yeah. So there's a, like, you could say like I should have been able to handle it with all the prep or whatever, you know, or at least I was, I had a lot of training and yet that the thing that actually, you know, actually experiencing that was very impactful, and, and I was definitely in a state of threat and reactive. Um, so I go— I went for a bike ride, and I remember just— I just stopped at this bridge, and I was— I was nauseous, really. What— I was like ashamed and, and scared, and, um, it showed up as nausea. And not— I don't want to gross anyone out, but, but, but basically, like, I just let whatever whatever feelings wanted to come, come. I didn't actually like throw up or anything, but I almost like, I felt like I was going to, and I didn't fight it. I just let that happen and really felt all that like shame and nausea. It was not pleasant, but I, I, at least the training, you know, taught me like, okay, don't fight the feelings, like, you know, allow it. And then on the drive home, I've told this story, um, my wife, God bless her, She's like, well, what do you love about yourself that has nothing to do with like your money and success? And I remember saying, just being like, well, I guess I'm just like a kind, fun-loving guy. And it was like a profound moment for me of like, oh, what if that's— what if that's enough? Yeah, I still— yeah, I kind of get chills even as I tell the story. I was like It was a real shift moment.

Yeah, your identity to actually take— actually recognize that part of you.

Yeah, that like, I, I'm worthy. I'm worthy without the money. And I don't know if I could have gotten there. Maybe I could have enough meditation and, you know, spiritual connecting to sort of essence beyond any lack, etc. I don't know. But my path was actually losing all that money. It really freed me up, freed up that attachment. And now I'm able to make and lose a bunch of money. And it's— yeah, I'd say like it's, it's been a steady growth over the last number of years in my ability to— I'll just use the example, like look at my Coinbase account., you know, go up and down by pretty significant, you know, relatively significant amounts for me, and it no— basically no longer affects me, which is pretty cool. Like, to me, that's growth. It's like if I'm moving from being a conditionally happy human to being an unconditionally happy or peaceful human, well, I've now largely removed a condition that previously was absolute, like, strong, firm condition for my well-being.

And when you reflect on that, like, what do you— how do you see that you created that experience for yourself the most? Like, what were the top 2 or 3 ways that you created that? That's easy.

By the way, before I answer, I don't want to— I don't want to overstate it either, because, like, you know, I recognize how privileged I am, we are, you know, living in the US, family, having the, you know, even after losing it, like, it's not like I went to zero and had to sell my house and sure live on the street. And I do know people who have been homeless and have lived in their cars, and they have actually told me something similar, like, I lived in my car, I was homeless, and I was like, ah, not ideal, but like, it was okay. And I'm not, I'm not trying to trivialize in any way homelessness, but the, the visceral liberating to realize you don't need all that stuff.

I mean, we, right, This is a small version, but we were at a religious retreat this past weekend with the kids and we stayed at La Quinta Inn. And, and it was like, you know, I was like, this is what a 3-star like property is. And they, they really didn't understand. I mean, they were like, there's no room. So, you know, and I was like, okay. But then part of it is we got through it and it was like, everyone was fine. Like, yeah.

You know, or camping. I feel like sometimes when I go camping, I'm like, this is basically free. Like I could, you know, you'd be okay. Yeah. Maybe a little cold in the winter. Um, okay. Your question was, how did you create that?

You, you went through this experience where you couldn't breathe and you like thought your life was, you know, you had this nausea. How did you create that for yourself?

Uh, well, like write the recipe here. Like you're, you're inviting me to take responsibility.

I'm just kidding. I, I, there, I have, I, there's a, there's a thought behind the question for founders, but I'm, yeah, I'm curious. Okay. Top 2 or 3.

I mean, clearly I had a belief that having a certain amount of money meant that I was worthy and successful and free, and that having less money, you know, meant that I wasn't. Um, I concentrated my wealth in a small set of highly volatile investments, right? I could have had it all in just the S&P index and like, yeah, it would have been a blip, which is interesting. That gets to a whole nother thread. But what else? Those are probably the biggest ones.

I made up a story that like at some level you started, you know, and the reason I brought it up, because I think founders do this a lot with their companies, is you, you know, the saying is you start spending the money before it's in the bank, like before you have it. And because you said this comment earlier that you were like thinking your life was on one trajectory and was on some level— because, oh yeah, I talk about this offline and I like, I have this position in FIGR that's theoretically worth— and in my brain it has not entered into any— like, yeah, it's almost the opposite problem. I'm like, I tell my financial advisor, I'm like, mark that at book. I don't like— I don't want to consider where it is because until it's here, like, it's not real to me.

You know too much. Okay, so yeah, I mean, one of the things you know about me is for a long time I had, I think, like $10K in checking plus and would somehow every month be at like, you know, negative $9,800. Like, I would run it as like, as like close to the line as possible, you know, which was like, I had the money in investments, but I would just spend. And I've, you know, my philosophy for better or for worse has been to buy the most expensive house the bank will let me. So, um, because you live in it every day and like, that's so, you know, it's fun to live in a nice house. Um, so yes, that— those are other ways. Well, let's go deeper for a second because I think there's something interesting in my psychology or belief that I still see a little bit. I, I think the golden algorithm is in here somewhere. I'll explain what that means in a second, but There's a way, like, I have— I'm so overallocated by any normal financial advisor's, you know, efficient portfolio, whatever, toward illiquid private investments. Like, you might even say I'm addicted to, like, angel and startup investing. So why is, you know, why is that? I think it's a little bit like a lottery ticket, kind of like the one in me who believes that only a really inordinate amount of money will give me freedom is like, well, I don't want to just have it grow. And even though I know compounding is a big thing, grow whatever, 10% a year. I want to just boom, have it a big, huge win. And I'll just share the goal. This again, credit Joe Hudson. The golden algorithm is the idea that whatever feeling you're, um, avoiding, you end up creating using the exact strategy you've employed to avoid it. So, so if I map that onto this situation for me, I think it's like I don't want to ever feel trapped. It's those freedom ultimately, like I want— I don't want to ever feel trapped. I want to feel totally free. Um, well, specifically avoid— I don't want to ever feel trapped. So I, every time I get you know, extra money, I pile it into some illiquid private investment that I think might free me someday from the money, you know, any kind of scarcity around money, and end up feeling trapped. Like, I have many months, despite how, you know, successful my coaching business is, and other— like, many months where I'm scrambling to like pay all the things that I need to pay. And like, clearly it's completely self-created because I've just already invested all the money in privates, and then my credit card, you know, comes due. I'm like, oh God, where am I going to get the money to pay my credit card? So I keep creating this feeling of like I don't have enough money in order to someday experience that I have enough money. So yeah, I'm, I'm doing that, I think. But I think it's gonna work soon, Jesse. I think it's gonna work soon. One day.

This last one we just did. Yeah, there you go. But I think for founder, I mean, I think that a very common sort of specifically around money failure pattern is, I think it's, it's like counting your chickens before they've hatched, you know, and recognizing, and I, I think it's a really Dave Kashen. I've seen a lot of founders get into situations where they go, including myself when like The company's worth X and this is right.

Oh, I'm worth X.

I'm gonna have this. Look at the houses on Zillow I'm looking at. And then the company's worth 30% less than what you thought, which is still an insane amount of money. And they walk away from a deal. I mean, there's these stories, especially with AI now hitting SaaS. It's like, right, the company's worth a lot and you walked away from it. And anyway, I, I think there's just, there's something there vis-à-vis it's where like money really specifically intersects with the founder journey. And you see a lot of very emotional decisions being made around money that are, that are, you know, pretending to be rational choices.

There's a few thoughts coming up around that. One is as a scorecard, right? We have this absurd sort of culture in Silicon Valley, especially with AI companies now that like, basically if you're not, if you have, if your company is not worth over a billion dollars, you haven't succeeded. Yeah, I mean, I, I'm like laughing even saying it because it's so absurd. And yet if you ask a bunch of founders, they would probably tell you, like, if they're really honest, they believe that. Um, which is, I mean, yeah, like what an absurd little marketing and branding from the VC industrial complex. Sure. Yes. Like what an absurd little microculture, right? Like if the other 8 billion humans in the world kind of got wind of that, they're like, What, like, how is that even, you know, most of the world lives on less than $2 a day. Like, how is that, you know, yours? So there's that, that whole, like, I think it's important that like valuation money, you know, how much money the company is worth is somehow the scorecard of whether you are successful or not, which then is your scorecard for whether you're worthy or not. Um, there's also, I, I think it's worth just going to a moment on this notion of freedom because it feels on the face of it like, isn't it obvious that more money gives you more freedom because it allows you to do more, buy more things and have more experiences that cost money, which of course is true. What's interesting about that is a few things. One, like, where does that end, right? Like, oh, I can get a G6, but only one, you know, private jet, or I have a Netflix subscription, but not my own jet. Oh, but I can't go on a rocket like, you know, to the moon like Bezos, you know. So there's a way in which it's just a trap if you think that like your ability to buy anything is the only way you'll be free. You'll never be free, right? You can't buy the Earth, you can't buy the universe, you know. It's like, it's— your mind could always use that to have you feel not free. Um, there was a book called The Soul of Money by Lynne Twist, and she made some comment like Isn't it more freeing to not need the things that money buy than to have enough money to buy everything you could possibly need? And again, what, what creates that is not making those external objects, even if— or experiences, um, mean something about your safety, freedom, and worthiness. And again, I think the most important point that, that we've made here is that, like, around freedom, is that freedom is a feeling. And you could feel free in prison and you could feel trapped in a mansion. Yep. It's a feeling. That's— and it's not— I'm not saying that conceptually. I'm saying that's what you actually want, even more than wanting all the vacations and all the houses. You're chasing a feeling.

You're chasing a sensation.

You're chasing the feeling. Yeah. And, um, and so for founders, that's You know, like they probably particularly value freedom. That's why they're founders, right? They stepped out of something that felt more constraining, like a corporate, you know, job or environment or chose not to do it. So they probably are disproportionately— we slash they are disproportionately kind of tilted toward or value freedom. And so I do think because you made this point earlier of like, you know, work the way most people can't for, you know, won't for 3 years so that you live how they can't for That's ultimately, I think, mostly about that sense of freedom that they're chasing, that like, if I shackle myself— I use that word purposefully— to my company for 3 years, then I'll be free for the rest of my life.

Is that right? And, and I mean, I have a question, but the, the one— there's a very common experience where founders sell their companies, they get the said freedom. There was the founder of Loom who wrote that long post about how he's like, I sold my company, I made hundreds of millions, and I'm lost, and I have no idea what do. And so, that's a very common pattern you see where you get the freedom and then you're like, "What is this?

I don't know what to do." I could do anything. I'm totally free and I'm freaked out because I don't know what to do. And all I want is to have a structure, purpose, or some kind of constraint again so I can feel not lost.

So, when you identify this, I mean, this is right, it's a feeling of freedom and you're coaching someone on that. How would you coach them to, to build more awareness around that feeling?

Hmm. And by the way, we could do the same for security and worthiness. Um, I think one thing that's useful is to try to invoke the, the past. Like, think of a time when you really felt totally free. Mm-hmm. If there's none, you could, you could try to just imagine the— okay, imagine, great, you did it. You sold your company for $1 billion. You got the $600 million, probably not by that point, $300 million, you know, in your pocket. Like you can buy anything you want. You never have to work a day in your life. Your interest alone is, you know, $25 million a year. Like, imagine you have it. And like, what does it feel like to be you? And so it's almost like you, you, you like flip it back, like you use like a ninja move or a jiu-jitsu or something, like you use the belief to, to get them to, to feel what they think it will feel like, and then notice you can feel that right now just by picturing it, right? Right, like the feeling, like it's like, where do you think the feeling is going to— it's not like you inhale it, suddenly or like eat it, you know, like once you've made the money, like where did that feeling come from? It was already inside you. You just allowed it. And I think that's like a really subtle but profound notion. Like, where do you think the feeling is going to come from?

Like, yeah, like I could imagine you saying like, well, what, what conditions are true for you to experience that feeling? And I, you know, I imagine myself, I'm like, well, I'm like, I'm sitting in a nice hotel room or a nice comfortable bed. I, I'm not needed by anybody. I can do anything. I have the feeling I can do anything I want. And you start to actually go, oh, so like freedom for you is X, Y, and Z. Like, could you feel that tomorrow if you wanted to? And the answer of course is yes. For most, you know, most founders especially.

And it's like, okay, just get, get more right now. Yeah. Forget tomorrow. Yeah. And I've been fond of thinking of it like we have this want for a feeling. Let's just keep— stay with freedom because that's our example. What's been coming up for me lately around it is, okay, I want to feel freedom. What if that want is actually like the freedom part of you crying out for attention, right? It's like if I haven't felt free in a long time, one way to look at that is like I've been ignoring the aspect of myself that is free and feels free. And so the reason I'm— that want arises is because that aspect of myself wants— it's like, give me some attention, right? So I think that's a useful frame because it highlights the fact that it's not, it's not out there to attain. It's like the feeling you want already has that feeling in it. It's like the feeling calling out to be felt.

It's almost like you haven't let yourself be free enough and therefore you're now craving this thing called freedom.

Yeah. Or yeah, so I almost think of like a U-turn, like, hold on, follow that want back to its source. And what you find is it's freedom. It's a feeling of freedom that is wanting you to experience it. Um, almost like, like a gravitational pull or something.

Yeah. I love it. Well, we're, we're wrapping up here. How should we wrap this episode up?

Um, let's see. I would just invite you reader, listen, I guess not reader, you listener to, um, I guess reader if you're reading the transcript to ask yourself, what do you make money mean that it doesn't mean?

Mm. And that's a great place to start for asking this question. All right.

Thanks, Dave Kashen. Thank you. That was fun. All right. Bye.