The Parts You Reject Are Blocking Your Potential

Hey guys, this is Heart of Entrepreneurship with Dave Kashen, my BFF and longtime coach, and Andrew Warner, who's my partner at Bootstrap Giants. This is a podcast where we are exploring how you can be an entrepreneur, how you can build ambitious businesses from your heart and with love, as opposed to with fear and a whole host of other things. So every week we talk about a different topic. Uh, it's pretty freeform, but we're, you know, Dave, Dave is a, an awesome, amazing coach who's coached Instagram's founders, Coinbase founders, a whole host of others. But you get to just listen to him talk for free. So welcome to this awesome podcast. Uh, today we're gonna talk about shadows. So maybe Andrew, you can jump in. We can answer our shadows or talk, get us, get us feeling, and then we can talk about what these shadows are and frameworks. But then I think we wanna also talk about how they affect founders, how they affect building a business. All those things.

I always like a personal example. Does one of you have a personal example of a shadow that you had that you didn't get to expose to the sun?

Yeah, I, I can, I can start. I'll actually give an easy one, which is my wife. You know, she's the most giving. She's a Type 2 in the Enneagram. She's always helping people. And anytime she sees somebody kind of like solving for themselves over the group or over others being selfish, it like really bothers her. And there's a part of her, the idea of a shadow is there's a part of her who is selfish, but she doesn't, she basically says, no, I'm not, I'm not that way. And so that kind of gets her riled up when she's around it. I think for me, I mean, Dave knows this from a lot of coaching. I think the last 2 or 3 years, uh, Andrew, I don't know if we've talked about this, but I'd say one of my biggest shadows is the victim. I've been unpacking that for at least 2 years, maybe 3 years now where I think growing up, like if there was a problem, it was either, you know, spin positively, which is kind of the hero, right? Hey, we're gonna figure this out. No big deal. Let's get to work. Or it was kind of meet it with frustration and anger and kind of, you know, bull your way through it. And I would never, I don't know if you ever heard me, have you ever heard me complain, Andrew?

I heard it once in a story, literally.

Like, that's the, I feel like Jesse never complains. And that's actually, there's a pretty big shadow of like this, weak, victimy person that I'm like, oh no, I'm not that. That's not me at all.

Isn't this okay then, Dave? Like, why would you want him to start being a victim and exposing that?

Um, because, because he is. And I don't mean he is a victim, but I mean that, uh, like, we all have all the parts. And that, I mean, that's been one of the biggest realizations. Like, all humans have all the parts. And so if we deny parts of ourselves, we actually, um, we don't feel whole. Right. And we actually, we tend to compensate for it. So I'll give you another example for, you know, for me, um, you know, shorthand for it would be like, I am not an asshole, right? Like I am a kind, loving, nurturing, supportive guy. I'm not a jerk. I'm not, you know, um, and so on. If I'd see somebody like you know, be super assertive or yell at somebody or be really aggressive, I'd be like, oh, what? Oh, that— what a Neanderthal, right? What a, you know, what a jerk. Um, and it took me a while to, to get like, oh no, I have that part of me too. I've just learned that that's not okay. That's not a good way to be. In order to, you know, as a kid, probably I had to be like complacent and nice to, you know, to get my needs met. And so I've really played with this and it's like, okay, can I first just acknowledge, like, I have that part of me too that's like, gets upset or assertive or just wants it the way I want it, you know, and wants to like bulldoze sometimes. And when I could start to acknowledge it and then like actually appreciate that part of myself and then let it out, I actually became a better coach, you know, because I'm now able to like challenge my clients and be like, hold on, like, That's not true what you just said, or like, you know, that's bullshit. Or, and you know, it was like I was denying a part of myself, so I was less whole and less, um, behaviorally flexible. Like that's a big thing I focus on with clients. You know, it's a little wonky term, but like behavioral flexibility, right? If you can only act in certain ways, then you can only create certain outcomes. Right. But if you can act anyway, right, then you can create a wider variety of outcomes.

So what's the benefit that Jesse would get if he expressed his victim?

Well, let me take the— I wanna back up a little 'cause I know Andrew and I know how he thinks. And Andrew, one thing we have to recalibrate for you and for everyone listening to this is what's the goal of all of this? Hmm. Right. And, and I think that's sometimes I feel like sometimes we lose you, Andrew, and probably a lot of people in the audience around what's the goal. And I have lots of founder friends and I myself was this way for a very long time, which was like, What do you mean? I want to make the most money and be the most successful I possibly can be. That's it. That's my goal. So what the fuck is all this stuff? It's just silly. Why, why, why are we doing all of this? Why are we talking about shadows? And, and I think I would actually do this with you, Andrew. Andrew, is that how you feel sometimes when we're talking?

I do feel like, no, I, yeah, maybe actually now that you mentioned it.

When you get all the money, when you get all the money and success that you want, what do you think you're going to get then?

I guess what I'm looking for is clarity on today by understanding what matters and where the points are and spending just time on that groove. And everything should either be in service to that or what's the point of it?

But hold on, bear with me for one second here, Andrew.

Yeah.

When you get what you want, success, money, whatever it is, like you're famous, what do you think you're gonna get then inside?

This is, this is weird, but I don't even think about what I'm gonna get at the end. I just think about that it's going to give me clarity today.

So you want clarity today?

Yeah.

Is that right? Or you want clarity? You want, I mean, most people when you, most people when you do this little track, they go, well, I want lots of money.

Cool.

What, what's that gonna give you? Oh, that's gonna give me freedom and control. Well, what's that gonna give you? Oh, it's gonna give me peace and I'm gonna be whole and I'm gonna be full. And I think if it is the same end goal, people think that their, their how for it is like money and success. And I think what Dave Kashen is offering and I've sort of come around to is that there, first of all, I've met enough rich people to know that like money and that stuff doesn't give you any semblance of that. And that instead that the way to get to freedom and the way to get to this sort of peace is actually by, by fully owning who you are and being who you are. And that's where shadow then all of a sudden becomes so important because by, for me, even in the last 2 and a half years, acknowledging this part of me, man, I've, I've, my whole insides have changed because I'm not constantly resisting this part part of me that feels bad for itself or sad or, um, and it's like let me become a more full person, which I think is the goal of why everybody wants lots of money and all these other things anyway.

That is a good reset. And you're right that I do keep coming back to why do I want any of these negative feelings because they're going to make me feel bad. And, and Dave and I have talked about even feeling like shame. Why would I want to pay attention to any shame that I have? Just brush it off, much less welcome it. Yeah, exactly. And why should I, if I feel victim, welcome it instead of saying, brush that wuss off and move on to whatever I really want to think about?

All right. I have so many thoughts. Um, okay. I love what Jesse said about, uh, it takes energy to keep these parts at bay. I think that's a really important point because a lot of founders out there are feeling drained and they think they're drained because of the hustle and all the activities they're doing., but you could actually do all those activities from a place of flow, right? In, when you're in flow, you do lots of stuff, but you don't feel drained. So at one level, I like the notion of flow because it feels like the intersection between, um, that feeling of fulfillment and wholeness and peace and being highly effective. And the tricky part in these conversations is like most people think it's a trade-off, like either I can go do this woo woo, like kumbaya stuff and become this like peaceful, happy couch potato. Or I can hustle and grind and, you know, like scare my team and scare myself and like, you know, play that game. And like, I, I want my clients to have everything that they want, including the, you know, their companies being successful and making lots of money. And I, I know at this point it's a trap if you think that the success and the money are gonna give you the sense of wholeness and fulfillment, et cetera. So the reverse is, you know, just makes so much more sense to me if you, if you create the experience or, um, realize, I might even say, cuz it's, it's, it's more like a letting go of, you know, if you realize how you are already whole and you can already experience peace and fulfillment, then you are, you can actually be way more effective and way more in flow as you create whatever you're trying to create. So to me, it's like the ultimate win-win. Like you get to be peaceful, happy, joyful, in flow, and it's not like a guarantee of success, but it's more, it's easier to create the results that you authentically want. And, and the authentic piece is important because if, you know, if you're really just doing the, your startup from a place of like, trying to prove something or live someone else's life, yeah, it might lead you to, to be less successful or even quit. But to me, that's a win because that's you following your authentic path. But if your authentic path is like, I really want to build this thing, I think you're actually going to be more effective and more successful. So it's both end.

Uh, Andrew, one other thing I'll just add is peace. Let's, let's agree that the goal is peace. Now you could think that money will get you there or whatever, but I think Empirically, that's so untrue. And nobody at this point, I think you people think it, they feel it in their body, but they don't necessarily believe it in their head even at this point, cuz it's so obvious that some of the richest people are some of the least happy people. Um, but another word I like is integration. Like by integrating all of your parts into your whole, you become more peaceful and you become more—

you feel more whole. Literally feel like the word fulfilled is such an interesting word. People throw it around a lot. Like, oh, I want, I want to feel fulfilled. And they think that means fulfilled, like, like I've achieved some outcome, but it's just like feeling full. That's literally the feeling you want. Well, that's wholeness, right? Like you feel full when you allow and like you said, Jesse, integrate all the parts. Um, and even like, I don't know why my mind's going there, but some spiritual teachers like Ram Dass, something of, you know, for many, many years, he was on a chase to feel high. Right. And a lot of us are on that chase, whether it's through business or through drugs or through spirituality, or it's like, I want to feel that high, that like awakening experience that like, you know, or adrenaline experience. And at some point in his journey, he tells a story. He was like hanging out with Alan Watts. He's one of my favorite, like, uh, Buddhist philosophers. And Alan's like, dude, you're like addicted to getting high. You know, like, what's up with you? And he finally realized that the path was really more about wholeness, about getting whole instead of getting high. So I think that's a, I think it's an important distinction. And one other thing I just want to throw out, I've, there's this cliché I say to clients a lot, which is if you can't be happy now, you won't be happy then, but you can be happy now. And so many people play that like deferred life game. Like, once I have this, then I'll be happy, then I'll be safe, then I'll feel fulfilled. It's just bullshit. It doesn't work. All right.

So how do we find these, these shadow aspects of ourselves?

And maybe one other thing for you, Andrew, that will be helpful is like, we all can think of someone in our lives. Maybe it's a cousin, maybe it's someone else who's like super insecure. Right? They feel like nobody likes them, or they have some part of them that's so— and it's so much in control that they can't even— they can't even have a conversation with you without giving you a guilt trip of some kind, or they can't even have a conversation without being super nervous because they have something that's really limiting them in some way. And when you say it that way, you go, yeah, of course there's a part of them. If they could— if they could face that and integrate it, they'd be probably more calm and more chill. And I think when it's very extreme, it becomes very obvious, oh man, that person needs to work on themselves. Like, But all of us have that, right? And so my victim, sure, Jesse can present in certain ways and it's not obvious necessarily, but like examples for me is like, I don't take as big of risks as I think I could. We've talked about this, Dave and I. So you wanna have a real money example of it? Like, I think I'm a pretty talented, smart, well-networked guy, Andrew, and here I am still bootstrapping businesses 'cause I'm afraid of failing. 'Cause that victim is so afraid, it's like that it never wants to be seen. 'Cause if, if, if I fail at a business, then it'll have to be seen. All of a sudden.

Meaning everyone else will see that you failed, but you can't see it.

Forget about everyone else. I'll have to face it and go, oh no, there is a part of me that's, that's like a, you know, fails. And so like, no, instead let's start businesses that, you know, you're gonna be successful at that are gonna, and so that's like a big, Dave and I talk about that a lot, but that's a really good example for how not seeing my shadow. And I've been working on like, no, I'm, I'm okay with this, this like crybaby victim guy in me and I want him to be more okay because then I can do whatever I want. 'Cause, 'cause I'm not, I'm not at, I'm not a victim to my victim, right? Yeah.

And I, I might even use the word helpless. Like victim has a lot loaded in it and I, and it's useful and like, just say helpless. Like, I don't want to feel helpless. I don't want to fail and lose people's money and feel that helplessness of like, I went for it and I failed. And so to avoid that, I'll just do things that are more like narrowly within my control, less risky. That's a great example.

So it has real consequences for, for hard business stuff when you don't see it and don't appreciate it and don't integrate it into who you are. Because what was the question? Dave and I were doing a session the other day. I think I texted you, but I was like, who would I be if I wasn't afraid to cry? Or who, who would I be if I wasn't afraid to fail? Or something. It was something along those lines.

Who would I be?

Because I don't, the idea of losing other people's money does, does bother me. Bother me for some reason.

What would that mean? You have to face, you know, being some way that you've decided is bad to be, a loser, a failure, or something like that. I mean, honestly, I'll just, let's just take that one. That was a huge one for me. Um, like it was like a third rail, this idea of being a loser. So like, if, you know, I, you know, if I, I probably also took, have taken less risk. Than I could have in many ways. And like, I'm really good at getting people to like me and saying the thing. Yeah, it's a little bit back to that, like being the nice guy. So I probably hold back in client sessions and things like that, or even more like in my own business, like, you know, retreats or programs I could try. Like the idea of being a loser, ugh, you know, it's like, Oh, I feel like disgusted. Like, by the way, it kind of alludes to your question earlier, Andrew. So one way to know what your shadow is, like, what's the thing that you most don't want people to say about you?

Mm-hmm.

Like, if you imagine people in a room talking about you, maybe you're not there, and they said, oh, Andrew, that guy's a total narcissist, or he's a, he's a liar, a cheater, a fraud, uh, you know, a hack.

Uh, guys, I gotta tell you, I started out not wanting this, like, what the hell? Now we're going into this wussy stuff that is going to make me weaker, to then going, show me how I can find my shadow so that I can figure out what's like holding me back and what aspect. Oh, all right. I'm a little, I'm definitely too embarrassed to even think about this with you two looking at me, but you're right that that is a good, that's a good one. What do I not want other people to say about myself? Where do I not want to end up? What do I not want? What do I not want 12-year-old me to say about myself today and in the future? That's, I think, what's gonna bring it out of me too. Ooh.

Yeah.

And for me, like, if, if I heard someone's, oh, Dave Kashen, that guy's a loser. Uh, you know, it's like hard to be with. Yeah. But I really sat with it and I was like, okay, how am I a loser? I was like, oh yeah, I've, I lose all the time. I lose money. I make bad bets. I lose clients that I, I maybe want to work with. I don't always go for, you know, there might be like a CEO of some cool company. I'm like, I'd love to work with that girl or that guy, that woman or that man. And, um, you know, but I don't necessarily go for it because I don't want the rejection. So like, there's so many ways that I am a loser. And, you know, part of the issue too is because our minds, especially when we're scared, tend to get so polarized because then if, if I think I'm a loser and I think that's the whole truth. Yeah, that's pretty hard to be with, but I'm also a winner. Right. So it's, it's like getting to the place where you can see both are partially true. Cause I've, you know, I've won in so many ways. I have a wonderful life and a successful career and family and all. So both, you know, both are true, but when I need just one to be true and not the other, like I'll twist myself in knots trying to make sure that I'm not seen as a loser, that I don't lose. And that really limited me. I mean, I can see many ways that limited me. Um, so I think that's one of the most useful things about recognizing the shadow. It gives you freedom. It's like, if, right, like imagine there was nothing anyone could say about you that would bother you to your face, behind your back. Like think about how empowering that is.

Liberating.

Yeah. And I love this definition. I think we talked about last time of empowerment as like being your authentic self no matter what, right? Regardless of the consequences. And I think they're, they're, they're very related because the parts of ourself that, that are real, that are authentic, but that we deny and repress get in the way of us being fully authentic. Cuz we feel shame or like, oh, I can't be that way. Um, and one other thought around, oh, just, yeah, another example, like I had a client, his company was struggling and I was like, it sounds like the team really needs you to be like a cheerleader right now. You know, and like, rah, rah, you know, and this is like an engineering background, just, you know, stereotype a little bit, tend to be a little quieter, more reserved. And he's like, well, no, no, I'm, that's not me. That's not authentic. I'm like, bullshit. It's just not comfortable.

Right.

You've just told yourself I'm this way. I'm not that way. And really challenged him to like step out of his comfort zone and integrate that part. And cause we all have all the parts. And did, and it really made a difference. But that's a common thing. It's like, or like giving direct feedback. Sometimes, you know, people, founders will tell themselves, yeah, but I'm not assertive like that. You know, it's like, well, okay, but you're here to serve. And if what the situation calls for is this thing, then being able to access all those parts of yourself is key.

Okay. So, so Dave, what is the shadow? Like, what's, let's talk about the theory, the sun.

Sure. Yeah. Yeah. So if we, if we use the metaphor itself, right, the shadow is the, you know, the, the places where the sun doesn't shine, you know, or the sun doesn't get to. So if you think of the sun as like the light of the light of day, right? It's like the parts of ourselves that we don't allow to see the light of day is the shadow, right? So there are parts that are denied, repressed, negated, resisted, et cetera. So, I mean, a really simple way to think about it is I am this way. I'm not that way. Right? Oh, I'm kind and friendly. You know, I'm not mean. I'm not a liar. I'm not a cheater. I'm not all the things you think you're not are shadow. Um, and then, you know, you use this, uh, you referenced this earlier talking about your wife, Jessie, that like when she sees other people who are selfish, she gets pissed off. Because she doesn't allow herself to be selfish. That's a, that's, um, I guess I'm getting beyond definition more to how to identify it, but that comes with the, it's like projection, like the parts of ourselves that we don't fully accept and allow and love. When we see them in other people, we tend to get angry and triggered and judge it. So that's a place to look. Anything that you judge in yourself or in other people is a shadow. And there's just to be, just expound a little bit. There's, there's sort of two, two ways that usually comes up. One is we know we have it in ourselves and we judge it, right? So, um, I can, I know I can be arrogant. And when I see someone else being arrogant, I judge them because I also judge myself like, oh, you shouldn't be arrogant. That's bad. Um, or I don't allow myself to be this way. And so I judge it when others do. And Um, I had a, I had a client who, uh, was on executive team and one of the other people on the executive team, um, was basically like, if this happens, I'm going to quit. And this client was like, that's so messed up. Like, how could, you know, like that's so manipulative and so coercive. Uh, cuz, cuz, um, that client like, um, didn't allow herself to set clear boundaries. Right, and be like firm like that. So when someone else did, it really pissed her off. And we looked at that and she, and it ended up being like one of the best lessons for her. I was like, oh, I don't allow myself to set boundaries like that. And so I get pissed off when someone else does. I thought that was a really interesting example.

So what, so, so Dave, when you, we got Andrew, uh, in interested in this finally. Yes. It only took 20 minutes.

Yes.

But now what? Like, what does he, what does someone do with, with this concept?

Yeah. Um, so one thing you could do with it is turn the whole world into a mirror. Like what if every other human being is just a mirror for you? Right. So one way I think about it, if, if the journey is a journey to unconditional love, so unconditional love for self and others, which You could argue whether that's the journey, but that's one way I think about it. Well, then the world will just show you, other humans will show you the parts of yourself that you haven't yet loved. Um, and obviously the parts of them you haven't yet loved. And it's, as you're hearing, it's a direct mirror, right? So if you can love yourself unconditionally, you can love others unconditionally. If you can love others unconditionally, you can love yourself unconditionally. So you can play with it either way, and both are useful.

Um, And I think for, for the more, you know, again, hardcore founder.

Why do I need to love people unconditionally? Yeah.

Well, I, I think it's more just like, I, I do think people resonate with the state of flow and this'll like, anytime you're, the love has stopped because you're like, oh, I hate that guy, or I'm judging that guy, or I'm stressed about this, you're not flowing anymore. And love and flow are somewhat synonymous actually in the sense that, so you can be, if you're fully just flowing all the time, you'll literally be flowing all the time.. And, and that's a very effective way of being, not only a fun way of being, but it's also a very effective way of being.

Yeah. Maybe just for now we could substitute the word acceptance for love. Just, just 'cause it's a little more accessible for a lot of people. Like if there's something about reality that I'm not accepting, I block my flow, right? Like you just think, you know, like if, if you can use a river metaphor, right? 'Cause you know, water flows. If I, if I'm in the river of life and I'm just like, in floating down the river, I'm in flow. I'm in the flow. If I'm like, oh, the river shouldn't be floating this way, it should be slower, it should be faster, it should be going left, not right, it should be going right, not left, right? Which is the same thing we do of like, oh, Jesse should be kinder to me. Andrew should be more open-minded. Uh, you know, like anytime we're judging—

I wish this client wasn't churning. I wish the product had, you know, market fit. Like all those things are basically what's happening or flowing and then resisting it and stopping it.

Guys, isn't, isn't being an entrepreneur partially not accepting the reality that's around you and visualizing what you want, ignoring what you don't want, and then waiting and working until you get the world to where it is in your brain?

Uh, great question. So first thought that comes up, I, I, I broached this as a possible subject for a podcast today. I really like this notion that the team that sees reality the clearest wins. So I just, and when you just said ignoring the things you don't want, just like flagged in my brain of like, if you, if you're ignoring what's actually true, that is not a winning strategy. Right. And if you're denying or pretending, but even to your, excuse me, core of your question, if you're not accepting reality as it is, you're going to be disconnected from reality. You're not going to see reality as clearly as if you accept reality as it is.

But what if I, what if I see reality? What about the reality distortion field that we talk about? You see something. Hold on, hold on.

I think this is a really good, good question and a good point. Remember we did a whole episode on desired future state?

Yes.

And what you want in the future to exist versus what's here today.

Yeah.

And how, how to get to bridge that gap in a way that's, that's enjoyable and loving, right? And effective. You, you wanna be able to see reality clearly and then see your future clearly and be able to bridge that gap. So let's, I just thought of an, an example while you guys were talking. Let's say that we want to build a house, Andrew, on a piece of land.

Okay.

And the piece of land is just sitting there, but we have this big dream for a house. And you're saying entrepreneurs are builders. They're— they— and you're saying not accept reality. But I think that has become somewhat of a, like, it's a almost law or prerequisite that you have to be that way. And then that's like painful and you have to eat glass and get punched in the face and all these things. But if you were actually building a house, on a piece of land. What if you didn't survey the land at all and you tried to build the house? What if you didn't understand that, oh, the land goes down and then it drops by 5 feet here? The best entrepreneurs would fully understand the land, right? And then they would survey it really carefully, and then they would decide how to build the house that they envision on that specific land. So does that make sense, Andrew?

Yeah.

What, what you're describing of not accepting reality would be, just to use Jesse's metaphor, like God, why is there no house here yet?

Oh my God.

It's just land. I like, you'd be using all of your creative energy or a bunch of your creative energy on this, like wishing it was already different.

Right.

That's what not accepting reality is. It's like, oh my God, I can't believe this is still just a piece of land. I have this vision for a house. Why is this house not here yet? Why haven't they started constructing yet? Why don't we even have plans? Like we just spend all this energy wishing we were already in our desired future. And this distinction of time is really key here. Because when you talk about reality distortion field, right? A lot of people, oh, Steve Jobs, what he was, I think, very gifted at, and a lot of entrepreneurs are gifted at, is distorting people's sense of what is possible in the future. So when I say accept reality, what I mean by reality is what's actually already true. So that it's just a, a bit of a language, you know, distinction. Like you can, you can bend reality in the sense of you can bend the future. But when, when we're talking in here about accepting reality, what I mean, and I, and I think what Jesse means is accepting what's already true, the past and the present.

Because I think if you got so frustrated the house wasn't there, you may miss something important on the land that then screws your house up when you go to build it. And just one other funny on the Steve Jobs thing. I think Apple is amazing at accepting current reality, dude. They killed so many products. They would, something would get done and they'd go, you know what? No, this is like not good enough. Like we're gonna kill this thing. And I actually think Steve Jobs was probably very gifted at both DFS and, and current reality.

Mm-hmm.

He was also a big Buddhist, so maybe that had something to do with it.

I don't know. So what people call the reality distortion field, you're saying is just very clearly him knowing his desired future state. And getting everyone else bought into it. It's not him.

Well, it's like, hey, I don't think we can get this podcast to a million listeners, guys. And Andrew, you're like, no, Jesse, we can, and here's how we're gonna do it. And then you, you convince me that what I thought was possible in the future wasn't, wasn't po— it's not really reality distortion field. They should call it like what's possible distortion field.

Yeah.

Possibility distortion field is really, yeah, I like that. And that, by the way, that's a huge superpower of entrepreneurs. I know we're kind of drifting off of Shadow a little bit, but, um, but maybe not actually, because one of the things that gets in the way of founders declaring extraordinary possibilities is that fear of being a fraud, right? Or being a failure or being a liar, right? And I have founders that'll be like, but how can I tell my team we're going to get to a million? You know, podcast listeners when I don't really know if we can. Right. And it's like, oh God, you know, it's like that third rail is like, what if they see me as a fraud? And what it's like, yeah, but like, they know the game we're playing. You're not, are you really lying when you say that? Like, you're just, you know, you're creating the possibility. And so that's, I think that's an interesting place where they intersect. Like if, if you're too scared to be seen as a fraud or a liar, that might get in the way of a very healthy, normal entrepreneurial activity, which is to declare some desired future state as if it's going to happen. And it's not like people think you're guaranteeing them, right? Like when a founder comes and says, we're going to get to, you know, a billion dollars in, you know, when they pitch a VC, let's say we're going to become, we'd be a unicorn, a billion dollar valuation. The VC is not like, he has promised me that he's going to get to a billion dollar valuation and usually a liar if he doesn't, right? We know, they know what, we know what game we're playing here.. But if you've, if you, if you have this like the shadow of like, oh God, I can't be seen as a fraud or a liar, it might stop you from even that very normal, healthy, powerful leadership activity.

Why, why'd you ask that question, Andrew? How'd we get down this rathole?

I'll tell you how we got down this road because I keep thinking I shouldn't be paying attention to the part of my life today that I don't like, that I don't want. And that the best, the best people who, the best founders, the ones that I admire, don't acknowledge their their problems today. They just make you see what they want you to see in conversation and the way they carry themselves and what they build. But I think what I'm understanding you to say is it takes clarity of an honesty about what's here today, and then a lot of vision and imagination about what's going to be tomorrow. And it's okay to say tomorrow we will get there and maybe a little delude yourself or a little hype yourself up, but it's not okay to say, I don't have any envy today, or I don't have any of these other shadow Well, I think the other way we got here was we were talking about the concept of flow and this, this thing of the river flowing.

And anytime you're resisting what's here today, yeah, doesn't mean you're not changing it for the future though, to be clear. Doesn't mean you don't want it to be diff— you, you could say, hey, I like in the future, I want this to be different.

It's not resignation.

It's, yeah, you're not just ex— you're not going— sometimes I think people use the word acceptance and resignation synonymously, right? It's kind of like I was watching something about somebody who climbs mountains and stuff and they always say like, The second I let all my fear in and I let it through, then I can like, okay, now I'm going to walk the mountain because I felt all the fear versus like if I keep the fear going, it makes me, makes me like carry on and hold really tightly. And that's kind of a lot of us go through life holding on tightly constantly to all these things and the flow of the river. And one funny thing, I don't know if you know this, Dave, but the— in, in like literally the opening line of the Sikh scriptures, they ask the question, how can I get rid of the veil of ignorance? Like, how can I and the answer they give in the, it's like in the 10th line for anyone who's sick, it's basically like to flow with, to flow with what the universe is doing. Essentially, you can, you can translate it as God's will or whatever, but it's basically to flow with how the universe is unfolding.

Um, I want to add a few thoughts. One is around doubt. So, um, a lot of founders, maybe all, Uh, but at least most founders that I know that I've worked with, um, have doubt, self-doubt, and they think that others, other founders don't. Oh God, look at Sam Altman, look at Elon, look, you know, like, and so they think in order to be con— look at Jesse, in order to be confident, I need to not have self-doubt, which is another version of sha— it's like, oh, doubt's bad. I gotta push that away. Ironically, when you just welcome, like, oh yeah, I have, I have some self-doubt, right? You actually feel more confident. You don't make it a problem that you have self-doubt. You don't make that mean that there's something wrong or you're not effective or you're not capable. You're just human. So again, it's another version where if you integrate that shadow, but what's for most people shadow is like, you know, if I, if I like was a founder and I come and say, yeah, I have a lot of self-doubt. Right? Most founders don't, don't go public with that. Right? I have self-doubt as a coach. You know, I've been doing it for 15 years. I've gotten lots of accolades, whatever. Um, and I, I have, I have thoughts many times, you know, often I have thoughts of like, oh, you're not doing this as well as you could. That session didn't go well. If some other coach were doing it, it would have been better. Right? And I have, over time, it's taken me a while, but learned to just welcome that.

Oh, okay.

I have some doubt.

Like, and we, and this, I mean, Andrew, we teach this in the accelerator because it's something, you know, I have two funny examples of this. One was I like met with Rick Elias, a billionaire founder of Red Ventures, right after he bought Bankrate, which is a publicly traded multi-billion dollar company. And the first words out of his mouth were, we have no idea what we're doing, Jesse. First I thought he was kind of being like self-effacing, but then I realized he was almost reminding himself of that to, to just like know that it's like, and in some ways it's empowering. It's like, I don't know what I'm doing. We're gonna go figure it out. The other example, Andrew, I'd give you is we, when we first started working on Bootstrap Giants together, we went and closed a bunch of big name sponsors, Superhuman, Notion, Rippling. And your tendency was to like sell them the dream. And mine was like, my pitch was, here's who we are. I have no idea if this is gonna be effective for you guys or not, but I think it's worth us trying. What do you think? They all tried it. It didn't work for any of them, but I think they would all take our phone calls if we, if we called them back, right? I mean, I think they still talk to us.

I did like that approach a lot of just being open and saying, we don't know where my approach would be. The opposite would say, here's what we're going to do. And then you use that promise to fire me up to find a way to deliver. And then maybe 2 out of 10 times feel shitty about myself for not getting there.

And I think the other thing it does is it creates false— like, you know, it does create some false expectations. And it's just not real. It's not reality. And I like to sell that way too. I mean, when I'm sure of something, I'll say it, but I think authenticity and that stuff really goes a long way in those situations. And I think the idea of admitting doubt really makes people trust you more.

Yeah, I think there's a clear connection here between being authentic, being vulnerable, and embracing the shadow because We have these parts of ourselves, right? So pretending that we don't is by definition not authentic. And these are the parts that we tend to hide and, you know, organize our life to like not experience or not show. And the more that you can love and embrace and integrate those parts, you know, the more authentic you are.

Yeah. Dave, one, one question I have for you, you know, We've been doing this work together for 7 years now, I think. Um, and I didn't have, I had no expectation. I didn't understand any of it when we started. And for the first couple years, a lot of our time was spent on awareness building.

Mm-hmm.

Um, and I've seen a lot of different friends or people who've taken my advice, whether it's like they go do medicine journeys or they go whatever, who actually haven't built that first layer of self-awareness. Mm-hmm. And I've noticed that it like, I don't know, it can lead to some funny things. And so I'm curious, I guess, like a lot of people, when you talk about shadows, like I feel like the biggest issue most people have is they have no idea what their shadows are or even how to stop and tune into their shadows. And like, what's the prereq to shadows?

Uh, yeah, self— a few thoughts on what you just said, but self-inquiry, you know, curiosity. Curiosity is probably like You say how?

Yeah.

Yeah. Um, let me make one broader point and then come back to it. I think that there's, well, maybe two. Um, I think there's a distinction between self-discovery and self-improvement. That is a really important distinction that maybe we'll talk about more in the future, but, and I have become increasingly a believer and advocate for the power of self-discovery. And actually all the growth that that leads to, whereas self-improvement sort of ironically tends to impede growth or at least make it less efficient. Like we naturally want to grow or we naturally grow. And if we, if we get clear and clear about who we really are and what's in the way, we'll, we'll, we unlock that growth and we can talk more about that. But I mention it because like even with psychedelics, some people do it, or meditation, as a self-improvement technique. And it tends to sk— this may be the point you're making. It tends— first of all, just context matters. So if you're doing it from that place of like, there's something wrong with me, I need to fix it. I need to make it better. That will really shape the experience of whatever it is, meditation. Like if you're doing it to try to get somewhere. It already sort of undermines the experience. Um, so short answer is actually tap into your curiosity. Like most people, if they're willing to see it, they're probably pretty curious about their own patterns and who they really are and like what's true, like a rigorous curiosity about what's actually true. Might be the most powerful journey one could take. What's really true? Who am I really?

But when you, when you talk, let me push back a little. When you talk with some people about this, they're like, no, I'm, I'm good. Like, I, that's not a thing I have.

Mm-hmm.

And it's like, of course it's a thing you have, but you, you like don't see it yet. Um, and I've had that for myself. I mean, I've had things that I've said to you 5 years ago that I'm like, oh, that's not. And now, now it's like, oh, it turns out that really is. And like there's layers and So what's your question? I think the rigorous self-inquiry is, is good. And I'm trying to bring a little bit more sort of like, what do I do with all of this? So you've convinced me shadows could be valuable, but I don't know that I have any. I think I'm fine.

Oh yeah.

How do I start to—

just look at what triggers you and what pisses you off. Like most, that's fun.

So Andrew, what's something that pisses you off? Let's have some fun with this.

You asking me or Andrew?

Andrew, Andrew. Sorry.

Uh, a few things were coming up earlier as you were talking.

In this, in other people, for this purpose, in other people.

I, I don't have it in other people. I, I, I don't, I tend to, maybe it's the interviewer in me, maybe it's something in me, but I tend not to get pissed off by other people.

Like wives or kids, political figures.

Oh, uh, actually, all right. My wife, interesting that you said it. Any negativity. I don't like to hear that we've got problems that we have. We invited 3 families over for your dinner on Friday. I thought, great, 3 families will sit around the table. It'll be nice. These people must have a ton, 5 kids each. I think we have, we have way more people than can fit around a table. I'll figure it out. I do not like when she's talking about how difficult it's gonna be and how we're gonna figure out food and where we're gonna sit. I don't like hearing complaints and problems. Okay, so what does that mean in me? Look at how fired up I am about that.

Okay. So that's a shadow. Go ahead, Dave. You're the professional.

Well, I, one thing that's interesting is I, I've heard this theme throughout this conversation today, right? Like the entrepreneurs I most admire are the ones who ignore all the difficulties and challenges and just focus on the few. Like, true. Those might not be the most successful, extraordinary entrepreneurs. Those are the ones you most admire because they map your kind of model of what's good and bad. So I just, I thought that was interesting how consistent that pattern is in you of I don't like negativity. I don't like acknowledging things that are difficult or hard. Um, so yeah, well, one, I, I'm really curious, like, what does it cost you to have to be positive all the time?

You know, there is a, there, there's a very good chance that these people will come. I don't, I actually, I don't believe that the chance that they're going to come and there's not going to be enough food or a place for them to sit. Um, Maybe like last minute, more of a scramble, I guess. But that's not, that's not the bigger cost. There's something else that I'm not, that I'm not aware of that it's gonna cost me.

I mean, over— it sounds exhausting to me.

I don't know. I'm carefree and I ignore it. Maybe like the last minute there's a scramble and then it feels exciting. Like, all right, we're gonna figure out how to get 20 people to sit around this one table. And then another 20 around the other.

Okay. I don't know.

But Andrew, is there a part of you that, that, that like complains or, or like doesn't, like is, feels negative about things at times?

Lately since we had the baby, I suddenly, I went from never complaining, everything's fine to going, oh man, I don't have time. I don't have space for myself. Why do I have to wait till Dave—

And what happens when you do that? Do you judge that? Um, you judge yourself for doing that?

I get kind of slump, like I slump instead of, instead of going, instead of bounding out to the couch and spending my half hour by myself, I'm like, this stinks. Why do I not have more time up until now? I'm so, and also I was so drained because I had to keep watching this and doing that.

Yeah. So this is interesting. I, there's something I was gonna say earlier that I'll say now, which is there's a bit of a paradox here where, um, when you have denied parts of yourself, they tend to leak out. And the more you love and accept the different parts, the more choice you have about how you behave. So that's a little bit of what I think I'm hearing here, Andrew, is like negativity, complaining, you know, the, the, the negative one, the one who complains, the one who, um, sees how it can be hard, you tend to repress that, but then it leaks out. And so even when you maybe want to be like positive and just like embrace, you know, time with your, your, you know, young child, um, that negativity has to come out somewhere. So it leaks out there where it's safer to feel it. Whereas if you fully just like, well, just see, so you, so as you acknowledge that part of yourself, can you appreciate the negative part of yourself, the one who looks for and acknowledges things that you don't want?

Honestly, not yet. And we're close to the end. So is there, is there an exercise where I could do that?

I was going to ask Dave. So, so with, with, with Andrew or anyone listening, it's like, okay, I found one. I thought about what pissed me off my wife. I've got something. What do I do with it now?

So I would both look at, um, it might be easier to start with, okay. What do I, um, what do I not like about this? Because that's where, that's what's already right there. What do I not like about, um, what is this part of you about the one who sees things as difficult? It's a little bit like victim, frankly, like Jesse's. So, so it's obvious what you don't like about it. Well, uh, I don't know if we have time.

Hmm.

Yeah, we have a little bit. What do you not like about this part of yourself?

I don't like it because it's not energizing. I always like things that give me energy, and feeling superior to my problems gives me energy.

And, um, just check and see what— how might it serve you?

To acknowledge that— to acknowledge what?

Um, how might this part serve you, the one that is sometimes like negative or complaining?

I don't even see a way that it could serve me. Maybe the only thing I can think of in having conversations with you is that there— it is possible that I am spending a lot of internal brain cycles on avoiding it and not enough on just recognizing it and letting it go. And that is something that I could see.

Hmm.

Yeah. I wonder how much of, well, I had two thoughts. I wonder how much of it draining you is your resistance to it versus the thing itself.

Maybe. I mean, you've really taught me to pay attention to that and to see that there is an energy leak or that I'm diverting my energy to something else instead of just accepting it and moving on.

I got an idea.

Accepting. Yeah.

Every day at the end of your day, Andrew, write down like 5 complaints or negative things and then just like look at them, tear them up, let 'em go and go the next day and let's see how your energy shifts.

That's a fun experiment. I like that.

I'll try that. 5 things that irritate me, that I don't know, negative complaints.

Let yourself complain, basically let this part out. Like really let yourself complain. Oh my God. Oh, this was so hard and this was, you know, like play play the victim.

This isn't gonna work. This, and then, and then, but I think like, it's like you're kind of letting it, you're kind of like saying it and then burn it or tear it apart and see what happens. Okay.

I'm game. I'll try that. I'll let you know how it goes. I might switch from writing to talking cuz I think I might do better. Yeah.

I don't even know if you need to burn it. I, I, to me it's like play, like exaggerate it, like really go all the way into it. Right. That's a, that's a great tool. Like, I'll come back to my example when this whole thing about being a jerk. Um, I did this exercise called the persona party where you, you go to a party, literal party as this persona that you typically deny. So I went as this like macho asshole. I think I even had like a, you know, cigarettes like rolled up in my sleeves. I guess I was like '50s macho asshole. Um, and I could just feel these like aspects of myself, this energy, this power. That I literally had never felt. It was like, it was like, I guess, being an actor or being in like an out-of-body experience. And I assumed people would respond a certain way, like they would be like put off by it, but it turned out it was, it was actually fairly attractive. You know, people were like drawn to my energy. And so I really liked this idea, just, you know, to your question, Jesse, like first there's like identify it, then, then, you know, see if you can find the benefit of it or accept it, um, or appreciate it. Um, even just, it might be as simple as acknowledge, like, we're just human. Like, we're human. We want to complain sometimes and be a victim sometimes. Right? Like making that part of yourself wrong just creates this inner conflict. But I think that's another fun thing you do is go like exaggerate it, go all the way into it, play with that part of yourself that usually deny and see what happens. Like that experiment.

All right.

All right. That's a good place to end it.

I'll give it a shot.

Thanks, Dave.

Thanks, Jesse.

All right.

See you on the next one. Bye, guys.