The Entrepreneur's Inner Journey

Welcome back to the Conscious Entrepreneur Podcast. If this episode sounds like a conversation between two old friends, that's because it is. Today, I'm excited to bring you a really fun discussion with someone I've followed and respected for a long time, Dave Kashen. Dave started a number of successful companies like WellSphere and WorkLife, before becoming one of the most sought-after leadership coaches in Silicon Valley. What makes our conversation special is Dave's unique approach to what he calls the inner game of entrepreneurship, a concept that goes beyond business strategies and touches on the very core of what it means to lead with presence, authenticity, and heart. As Dave says, when you know who you really are, You lead with love, presence, and integrity. You create powerfully and experience a sense of peace, play, meaning, and fulfillment while building a wildly impactful business in the process. I think it's safe to say that we all want to lead from this space. So let's jump into the inner game of entrepreneurship with Dave Kashen. Hey Dave, great to see you. Thanks so much for joining us on The Conscious Entrepreneur.

Thanks for having me, Alex.

You've got this great background as an entrepreneur and someone who's been very thoughtful about their journey, now working as a coach and really changing the conversation around entrepreneurship. And I just want to kick off today with a general question about a topic you have brought up a lot to me and you write about a lot, which is the notion of entrepreneurship being an inner game. And this is not going to be something that's new to listeners of The Conscious Entrepreneur or to the folks who came to the Conscious Entrepreneur Summit. But I want to get your perspective on what do you mean by the inner game of entrepreneurship and why is it crucial for entrepreneurs to think this way?

So let me start. I'll start really high level and then kind of zoom in specific to entrepreneurship. One of the things I realized some years ago was there's two primary games that people tend to play in life. One is, can I get life to match my mind's idea of how life should be? The other is, can I just be with life as it is and relax my mind's idea of how life should be? Most people are playing the first game, right? Can I get life to match my mind's idea of how life should be? And it's a really challenging game. Even when you win, the joy, peace, contentment doesn't last very long. And because life is dynamic and our mind tends to be a bit more rigid, it's really hard to get them to match. So I realized at some point that the richer, more workable game, a game you could actually win, is the other game where I can more and more relax my mind's idea or let go or disconnect from my mind's mind's idea of how things should be so I can just be present with life as it is. And the beautiful thing, I think, about playing life that way is you win twice. So, first, you win because you get to experience the peace and contentment and joy and freedom that comes with being present and not wishing things were different, which is ironically, if you ask people why enough times, including entrepreneurs, well, why do you do you want to raise a big round? And why do you want to impact all those people? And why do you want to sell for $1 billion? Oh, then I'll have this money and then I'll have this. Well, why do you want that? Well, then I'll feel peaceful and content and joyful. Well, that's already always available now simply by removing what's in the way of you experiencing presence. So, I'm a fan of like, I want to go right to the root, direct path.. And so, you win that way because you get to experience the joy, the aliveness, the lightness of being, of being peaceful. And it turns out it's way easier to create the results that you want from that place, right? The less attached you are to the outcome, the easier it is to create. Like many people know this from dating or areas like that, or like if you're too clingy and too attached, it's actually repellent. I think that happens with life as well. With fundraising, with recruiting, with, you know, all the aspects of creating. Again, because the state that you're in when you're attached to the outcome is a very clingy, you know, constricted state. So, you're not as resourceful. So, that's the kind of paradox is the more you're relaxed and present and have your full resourcefulness by letting go of the attachment to the outcome, the easier it is to then create the outcome. So, I love helping entrepreneurs shift into focusing on that game because then they get to both have a better experience, more joyful, less stressful, more enlivening, more playful, and more likely to succeed.

And in the non-abstract, what was going on in your life when the light switch went, when the light bulb went off for you?

Yeah. I'll give you a little quick kind of context background. My parents were divorced when I was 5, and my dad, who I now know is totally doing his best, was not the most emotionally expressive man. And after my parents were divorced, you know, just felt the disconnect and made up a story that I was unworthy in some way, unworthy of his love, unworthy of love, just, you know, you know, the general sense of unworthiness that many people experience. And so I spent probably 25 years of my life trying to prove I was worthy, right? And in some way, it was that— it was that game, right? That game of, can I get myself to match this image my mind has of what is required to be worthy? So that looked, you know, I went to Wharton, studied finance, worked at Goldman Sachs, People laugh sometimes when I tell them, they're like, you were an investment banker? Like, that's, you know, farthest thing from the sort of deep emotional, you know, sometimes spiritual work.

And yes, but it's a great way to get accolades. You go to a good school and people say, hey Dave, what a great job.

You're so smart.

Then you go work for a good company. They pat you on the back. They say, wow, look at Dave.

Look, he made it, you know, by societal standards, he's a success. And in some way, I was super lucky. So I did— I went to Goldman. I worked at one of the top-performing hedge funds. And that was like the job I thought I was always supposed to want. So I feel super lucky in a way that I arrived relatively early in life at the top of this mountain I thought I was supposed to climb, and then looked around and was like, where is the sense of fulfillment and peace that I thought I would feel once I did all these impressive things and accomplished all this? And so that was kind of an early wake-up call, like, hmm, maybe, maybe this isn't— I'm climbing the wrong mountain, or, you know, playing the wrong game. Um, though at the time I was— I was— my hypothesis was that what was missing was more contribution, right? Instead of kind of, you know, reallocating capital and, and, you know, generating wealth for very wealthy people and institutions, maybe what was missing was, um, creating something new in the world that would serve people And so, that's— so, I went to Stanford for business school, started my first startup with a classmate. And, also, we built that over 4 years. Company was acquired. And, you know, it was a really challenging 4 years. I did not have a coach. I was not winning my inner game. I was suffering, struggling, stressed, feeling unworthy, feeling like an imposter. Working like crazy, frenetic. I was like a tale of what not to do as an entrepreneur, like ignore the inner game, sacrificed all my rituals and routines on the altar of— it wasn't even success. It was like, I can't fail. I've never failed at anything. I've told everyone I know that I'm doing this thing, right? Because you have to be pretty public when you're doing a startup, I think, to be successful because you're drawing all the resources.

And so, what company was that?

That was called WellSphere. It was an online health and wellness company, ironically, because we weren't that healthy and well while we were building it. And, we sold that to HealthCentral, which was kind of like Sequoia Interactive Corp's online health sort of platform. So, as soon as we sold it, I felt like a shell of my former self. So, my hypothesis, because this again was sort of outer game, I was like, "Oh, if I do this thing, then I'll be fulfilled." but it was still me, right? No matter where you go, there you are. And so, for the first time in my life after we were acquired, I felt like, okay, at least, you know, check the box, I did the thing, you know, I didn't fail. So, now I can have a little space, mental space. I hired a coach for myself for the first time. So, this was 2009. And he encouraged me to go to a personal transformation, kind of weekend seminar where I learned what I shared with you earlier. Oh, you know, what happened was my parents divorced, the thing around my dad, the story I made up was I was unworthy. I made up the story. I could let it go. And, if I let go of that story, that created the possibility of living an authentic life. And, that was a real breakthrough for me. And, I recognized that what I really love is supporting human beings to thrive and be their best selves and transcend their limiting beliefs. Wake up to the truth of who they are. And maybe I didn't have those words at the time, but I sort of played like psychologist to my mom growing up. I love my psych classes, but I had to do all the econ and statistics and finance and all that stuff because in some way, I think I viewed psychology, therapy, coaching, oh, those are less than, right? Those aren't the prestigious careers like finance and investing and even being an entrepreneur. So, I really had to let go of needing to prove myself to give myself the freedom to do what felt like my authentic calling. And I enrolled in a coach's training program. And from the first weekend, I was like, oh my God, these are my people. This is what I'm here to do. And that was 15 years ago and sort of never looked back.

I love the framing about the two, the inner and the outer. And we all get sucked into the outer. And by the way, 90-plus percent of entrepreneurs, that's all we focus on is the outer stuff. Right? I want to raise money, hire people, get sales, get revenue, do this, do that, because then something great is going to happen in my life. And this is what you're talking about is the if-then thinking. So, like, Sri Kumar Rao, who you know, who's been on the podcast, he would say this is if-then thinking. And this is us making up a mental model of what we want our life to look like, as you're saying, and then basically saying, what conditions do I need to stuff in here in order to get what I think I want versus what do I actually want? And I just want to share and reflect back, and then we'll move on. But I just want to share and reflect back. Like, for me, it's been understanding what are the motivations? Can I be happy and content and peaceful with wherever I am right now? And the other thing that was really interesting for me is, and I phrased it like this at the Conscious Entrepreneur Summit in June when we all got together in Boulder. I said, one of the things that I wish I had known before becoming an entrepreneur is that the inner game is an infinite game. Right? So, you know, the difference between the finite games and infinite games. Infinite game, you just play for the joy of playing. It doesn't have a winner. It doesn't have a time box, doesn't have anything like that. And for me, the more that I do this and the more that I learn and the more concepts I'm introduced to and the more cool people I get to talk to on the podcast, I'm like, wow, there's so much more to this. It's like, hey, there's something beyond that and beyond that and beyond that. And frankly, I love that part of the inner exploration.

There's so many threads opening in my mind as I hear you talking. One is I've heard myself say to a few clients, if you can't be happy now, you won't be happy then. But you can be happy now, right? To your point, like someday maybe versus like the— at the deepest level, I think it's always already here, right? Like the peace, the joy, the fulfillment, it's just clouded by layers of, you know, constructs, ideas, beliefs, thoughts that get in the way of us noticing that. So in a way, if, you know, I hope people hear that as a relief. It's not like yet another thing you have to attain and gain and strive for and get to. It's actually much simpler than that. It's already here. You just have to remove what's in the way.

And so for an entrepreneur who's listening to this, or they've come across your work, or they've come across Conscious Entrepreneur, and they're sitting there saying, you know, there's something about this that resonates. I don't know where to start, but I feel energized by these words. I feel energized by these ideas. What are the tools or techniques? What's the first base to get to, if you will, on this journey? Because it can seem like a lot, right? And sometimes we're out there throwing around these big words and it's like, oh man, I'm never going to get there. I'm not going to go do— you know, people might say, I'm not going to go do a 10-day silent vipassana meditation. I'm not going to go do a week-long such and such thing, right? Like, what are the ways that we can get started and start to feel differently?

Yeah, so let me share a few. One of the first things I do, I say to clients— well, I ask clients, um, how do you know when you're thinking? And they usually fumble a little bit because it's an unexplored topic for most people. And eventually they get to a realization that essentially you hear a voice in your head talking. And say, okay, well, what's so interesting about that phenomenon is in order to hear a voice in your head talking, there must be a talker and a listener. So just that distinction, you know, most people spend most of their lives identified as the talker. And when you start to identify as the listener instead, you gain a lot of freedom and choice, right? Because some things, some thoughts the mind generates are useful. Most are negative and not. And, you know, if you were walking down some street at night and some drunk college kid says, "You're the worst," or something like that, it's so obvious you could just ignore that voice. But when the voice appears to emanate from inside your own mind and sounds a lot like you, or worse, you're identified as it, it's not as clear that you can just ignore it. So that's usually step one is just, can you just get a little bit of light between you and that voice? A little bit of this, you know, disconnect so you don't think that's you and you spend your whole day engaged with it, listening. I sometimes use the metaphor of like fishermen. Imagine you're this happy little fish swimming along in the present and your mind is this like talented fisherman and it knows just what bait to use, right? Oh, you screwed that up. Oh, what if this happens? And so your job as the fish is like, can you just swim around the bait? Or if you notice you got hooked, can you just unhook back? So that's like often just step one. You don't need to necessarily even meditate. Like, in fact, I know lots of people who meditate for 15, 20, 40, 60 minutes in the morning, but then they go to work and they're just triggered just like always. So like, I think there's an interesting distinction we could make about like the morning meditation versus living meditation. You know, I'm a big fan of kind of turning your startup into like your dojo for presence, right? Make it this living meditation of just noticing, oh, what are my thoughts? Like the heart pumps blood, the mind pumps thoughts. That's how I think about it. What thoughts are my mind pumping? So, that's step 1 is just detachment from thoughts. You're not your thoughts. You're the one noticing them. And then, there's a specific flavor of it. If I had to get like 80/20, if you really look, most of the time, most people are focused on the future they don't want. Especially entrepreneurs, which is kind of crazy if you think about like this human imagination is maybe the most exquisite, you know, creation that the universe has ever, you know, generated, evolved to. And then we use this tool of the imagination to imagine the future we don't want to have happen. Right. And not consciously. I mean, most people You know, yes, it could be useful to go spend an hour or two doing scenario planning, but that's not what most people are doing. Most people's minds are just drifting. So that's the other, just like 80/20, like, can you just catch your mind focusing on the future you don't want and instead shift to the future you do want? And, you know, you, you use the term motivation earlier, and, you know, I, I wrote, um, a post on Medium called Founders, it doesn't have to be this hard. And the point that I made is that most founders motivate themselves from tension that is created by either lack or fear, right? So we kind of sense like tension is a powerful motivator. Tension by its nature seeks to be resolved. So we either say to ourselves, this isn't okay, like I'm not where I should be. Or we're not where we should be, right? I'm not where I should be. I should be smarter. I should be further along. I should be more confident, right? I should be in a better fitness routine. I should, you know, or my startup's not where it should be. We should have already raised capital, right? This irony is like entrepreneurs are dreamers, so we're great at like dreaming up some future, but then we collapse the desired future into the present and wish we were already there and just create suffering for ourselves. And drain our energy.

Well, I mean, lack and fear are such dominant thoughts and emotions for entrepreneurs because— and part of it, by the way, is literally how it's framed to us. So the lack is we're under-resourced from the beginning. We're going up against Goliaths in our industry, or we're changing a paradigm or whatever it is that we're doing. So there's already this sense of like, hey, we're punching above our weight. And then the fear is what if it doesn't work out? What if I don't this? What if I don't that? All these stories that we equate. And for me, the way that I've overcome— so first of all, disclaimer, I've not overcome these. The way that I deal with these when they arise sometimes is I say, especially the fear one, is if I can zoom out a little bit and recognize that whatever I'm doing is just what I'm doing today or this week or this month or this year. It's not my life. It's not Alex Raymond. It's not my entire existence. It's just simply something that I'm doing today. Then I can see through a longer time horizon and think, okay, it might work, it might not work, it might this, it might that, but I no longer see it as so existential. That's at least how I deal with that particular one.

Yeah. Part of what you're pointing to is when you get perspective, you don't, you don't make it mean anything about you, or at least don't make it mean as much about you, right?

Try to. I try to. Yeah, I try to.

Yes, you try to let go of sourcing your worthiness from the company. Um, you know, I'll say this to you in case it helps you and it helps listeners. I often say to clients, or have clients, like, imagine a child being born right, coming into the world. Is that child worthy?

Yes, of course, right?

We know that. Yeah, everyone's gonna say yes. What, what the heck have they accomplished? They just like poop and cry, right? So how could they be worthy? They haven't accomplished anything. And I find that is sometimes a useful way, you know, and it's like, well, were you once a little baby? Of course, right? We all were. We're Were you worthy when you were born? Of course you were, always were, always have been, always will be. It's just the mind and the mental construct of self that has these questions of worthiness. Like, I think, you know, we're human beings, not human doings. Human beings are inherently worthy. And again, it's more of a releasing than a gaining. If I can let go of the story that I'm unworthy or that my worthiness depends on my success or my startup's success, I gain a lot of freedom. And then again, paradoxically, it's easier to succeed.

Let's jump into what I know is another really meaningful tool for you, which is Conscious Leadership. Now, it might be helpful actually to give our listeners a bit of a background on this because we have not done a deep dive on Conscious Leadership on this podcast. I need to go find Diana or Jim and get them on the podcast, but they have not yet been here. But tell us about the framework because I know you studied it a lot. Tell us about the framework, the tools, the commitments themselves, and how you tend to approach this.

Yeah. First, just deep bow of gratitude to Diana and Jim for what they created and their mentorship. So, so much of what I say is just parroting or things that I learned from them, through them, through my work with them. So, just want to give them their due appreciation and credit. And so, they wrote a book along with Kelly Warner Klump called The 15 Commitments of Conscious Leadership. So, that's kind of the manual, the overview. So, I typically explain it. Oh, and just background-wise, I don't know if people are familiar with the— I'm not just the HairClub president, I'm also a client. So, I spent 5 years as a student a participant in a forum, a monthly forum led by Diana. So that, you know, I was exposed to it before that, but that 5-year journey on the receiving end of coaching and the framework was so profound for me in my life that, you know, through that journey, you know, prior to that, it was one of the many tools in my toolkit and of course still is, but it became much more central as I just saw firsthand how powerful and effective it was. So let me explain. And then I joined the Conscious Leadership Group for a long time. And, you know, I'm no longer officially part of the group, but I, you know, beloved friends and mentors. So let me explain the concept by giving two distinctions. The first is actually I'm going to back up just for one sec because I think it's useful to distinguish the word distinction. So if I open up the engine of my car, I open up the hood of my car and see the engine. I just see a big blob of engine. I have no power over it. If a trained mechanic opens up the hood of a car, they see all these distinctions, therefore they have power. So I think these are some of the most important distinctions to being a powerful human. So, so distinction one is context versus content. So if your life is a movie, what's on the screen is the content. What's on the— what's the lens through which you're experiencing it is the context.

Right?

So, what's on the screen is the content. The lens through which you're experiencing it is the context. And, that alone is a pretty important— this essentially speaks to the inner game versus outer game concept, right? Context is decisive. Context determines how you see reality, what you perceive, how you're experiencing it, what resources are available. So, most people just try to play the outer game and change the conditions and the content of their lives. We're just infatuated with content. Context is transformational. So if we double-click on context, we'll draw a further distinction between two states of beings that humans tend to operate from most of the time. So imagine a horizontal line as a way to just demarcate these two states of being. So we can now refer to them as above the line and below the line. So when we're below the line, we're in a state of threat. You know, people describe it as victim consciousness, right? We see life as happening to us. We feel constricted, right? We're kind of bracing against what's happening because we perceive it as threatening. We get defensive, we get righteous. We want to blame sometimes ourselves, sometimes the world, you know, sometimes other people for our experience, right? It's like there's something wrong here. Who's to blame, right? And I'm right about it. And I, you know, we get essentially identified as our ego and back to like we source our worthiness from our achievements, from being right. So, what I love about that distinction, and I'll explain Above the Line by contrast, is what I have found is that most of the issues that human beings have, that leaders have, and that entrepreneurs have are really just symptoms of being below the line. Because when we're below the line, all of our default conditioned automatic survival patterns kick in. And it's almost like we're not operating as our full, whole adult selves. We're operating in some part of ourselves or some less mature part. And that's why I think a lot, you know, again, back to like going to the root, the root cause of things. That's why I love going to state, because if you can shift your state, all of the symptoms kind of shift at once. So above the line, by contrast, is a state of presence. So you can just be here now in a non-triggered, non-reactive state. And I sometimes use the metaphor of driving. Well, let me finish. So, when we're above the line, we're present, we're open and curious, right? Instead of wanting to be right. The shift from below the line to above the line generally involves taking responsibility for that which you previously have not, right? So, because if you think of above the line as creator consciousness and below the line as victim consciousness, when you step into creatorship, when you see yourself as the creator of what's occurring, you actually feel empowered and you can come into presence. When you see it as you're a victim and you're in threat, well, now you're disempowered and you're reactive.

Well, this simple tool of the horizontal line, like you're describing, above the line or below the line, you know, in the book and in their work. And by the way, so we should say this is Jim Dethmer and Diana Chapman, and they're with the Conscious Leadership Group. We should just name that out. But what they do, they talk a lot about you can investigate at any point during the day, where am I? And you can say I'm either above or below. And then the other thing to add to that is we would naturally think that being below the line is somehow negative or something that I need to change or be ashamed of or what have you. And the point, which I think is so powerful, is that we don't have to provide any emotional context on that whatsoever. We can simply notice where we are. And it's almost as though by noticing, then we're able to say, so am I okay being below the line? Because maybe I'm just like, I want to have a fit, right? I'm just like, I'm below the line, I'm going to have a fit and I'm going to have a tantrum. So be it. But most often, It'll be, okay, I'm below the line. I'm feeling fearful or anxious or burned out or whatever the overwhelm, whatever all the many things may be. Okay. Do I have some type of facility to do something about this? And so, so that's one of the things that I really love about that. And I just wanted to clarify for everyone because we're looking for, you know, quick things that I can do. And even though this sounds so simple above the line, below the line, there's so much power to it.

I agree. One of my favorite quotes is by Carl Jung. He says, until you make the unconscious conscious, it will direct your life and you will call it fate. So to your point about noticing, you know, awareness gives you choice, right? When you're not aware— that's what I love about this model, that's what I love about introducing it to people. It's like most people are like fish in water you know, what the heck is water, right? So, if you're below the line but you don't know the distinction, you're just like, "Well, of course, I feel this way because of the traffic or because my startup had a setback or a churn," right? So, it just feels like our well-being is at the effect of our conditions and we're not aware that there's another possibility, another way of being. So, just having that distinction, again, back to the power of distinction, is powerful. And to your point, you know, they jokingly say it's all about like real estate— location, location, location. At any given moment, can you locate yourself above or below the line? So, you know, you asked about like starting points. The, the next thing I do after going through sort of, you know, looking at some thought patterns and helping to get, um, some space, you know, from your thoughts, is help clients discern for themselves, how do you know when you're below the line? And get clear about that, right? I can, I can usually feel in my body constriction. I want to be right about something. I get, I'm defensive, I'm reactive, I'm blaming. One simple way is just, is there anything about my experience of life that I'm wishing was different? Right? At the simplest, we might just say, You know you're below the line if you're resisting something or attached to something, right? It's almost like a Buddhist notion of clinging, right? Resistance and attraction and aversion, right, is the source of all suffering, the source of being below the line. So, and then, okay, if you now start to develop the capacity to distinguish in any given moment, where am I? The next step is building the muscle of awareness that, as you alluded to, Alex, to just ask the question. So, the Conscious Leadership Group recommends, I typically have my clients download some kind of notification, like intentional notification app. Like, there's one called MindJogger on iPhone, Randomly Remind Me on Android. And literally, I have it say 4, 5, 6 times a day, "Where am I?" Or "Above or below?" And then, so for the first couple of weeks, clients will just have this thing pop up on their phone. And they're literally building the mental habit of asking the question, where am I? Right? Again, content is so captivating. We just get drawn into the content. You know, I was talking to a client earlier and I said it's almost like wearing 3D glasses. So you can start to see this other dimension of reality called context. And as a leader, when you can start to see that, you are much more powerful because if you try to have a, you know, content conversation, a decision-making conversation from below the line, you're gonna end up in drama because you're actually gonna be just, it's gonna be like two, you know, egos arguing about who's right and wanting to be right instead of genuinely curious and open and finding the best solution.

So what else is there besides the line? We're doing the conscious leadership kind of primer here.

Yeah.

Great.

So the line is kind of the core distinction and You know, I always say to clients, I'll walk you through in a moment the 15 commitments of conscious leadership. But the thing I think is most important to remember is fundamentally it's about your state of being. Right. And it's like, it's like if you're in, you know, in the middle of a big city trying to see the stars, like it kind of doesn't matter what techniques you try until you've shifted to another location. You won't see them, right? So, like, I just want to make that point that, like, the 80/20 is what state am I actually in? And then what I think is so brilliant is they've then mapped out kind of the realm of leadership and really reality, you know, being human, to these 15 kind of dimensions and then shared for each of these dimensions. And I'll explain what I mean by that. How are we oriented when we're above the line as contrasted to how are we oriented when we're below the line? So I'll give you some examples. I'll go through at least the first, first bunch. So the first commitment, when we're above the line, I mentioned this earlier, we take responsibility. Right. And it's important. And when we're below the line, we blame. Right. So that's the first distinction. And it's both of all of these commitments you could think of. Both as like indicator dials, like I know I'm below the line because I'm blaming, but also shift moves. If I want to shift above the line, I let go of blaming and I take responsibility. One thing I just want to say about that, because people get a little trapped and tripped up, responsibility does not mean blaming yourself. Right?

That's the— Okay, tell us more about that.

Sure. So, when we're below the line, We start with the premise there's something wrong here. And then the natural question arises, who's to blame? When we're above the line, we let go of the notion that there's something wrong here. That's just a mental idea. That's again, choosing your mind's idea of how reality should be over reality. So from presence, we let go of the story that there's anything wrong here. So there's nobody to blame because there's nothing wrong. Now, we might not be in the reality we plan to be or expected to be or ultimately want to be. But again, you know, you can't get there until you're here. So, you know, first we just have to accept reality as it is, come into presence, right? That's what allows us to be present is acceptance. And then you look, you look to see how did I create or co-create or contribute to or allow this to occur? And that leads to learning, right? Like I always say, like really the only point of the past should be learning, right? If we're using the past to beat ourselves up, you know, what good does that do? And the more you take responsibility, you know, it's one of these funny things where like at first bite, it's kind of bitter. You're like, oh, that's, I've been blaming my mother-in-law all these years. I've been blaming, you know, it's like I've been blaming my CTO, my co-founder. I created this? But then as you take more bites, so to speak, you're like, oh wait, but if I created this, that means I actually have some power to create something different, right? Because if I'm blaming, then I'm just the victim of the other person. So it's really an act of self-empowerment. How am I the creator of? One of my favorite tools is, I'll have to give you two, they're kind of related. One is called write the recipe. So like, Alex, you had a dinner party, you baked this amazing key lime pie. And I'm like, oh man, that was so good. Can you give me the recipe? But instead of a key lime pie, it's like, uh, you know, I don't know, stressed out, burned out culture in your company, or missing earning, you know, missing your target, uh, revenue month after month, or, you know, fight with your co-founder, or, right, whatever the thing is that you're wishing wasn't so. If you can write the recipe for how you created it or co-created it, you start to see more clearly what you can do to uncreate it, right, or create something different. And if you're— I find if clients are willing to take responsibility, they always get value out of it. They always see something they didn't see before, and then they know what to do. Um, okay, so that's Commitment 1, is responsibility versus blame. Commitment 2 is curiosity above the line versus being right. That's that we get righteous, right? Commitment 3 is around, um, feeling your feelings versus repressing feelings. And this isn't always obvious to everyone why this Physiognomy of Presence. But the real reason we go below the line much of the time is because there's some feeling arising that we don't want to face or experience. Most people have labeled sadness, fear, and anger as bad and negative. And so, oh, there's sadness, don't want to feel that, stuff it down, go into my head, imagine stuff, right? Or, you know, fear, don't want to feel that, go into my head, imagine. We get caught in these cognitive-emotive loops. And so, one of the most powerful shift moves is learning to actually just welcome and feel and embrace all of your feelings.

Knowing that many feelings don't last that long. What are they, 90 seconds or something like that?

Yeah, that's a great— I would go further than many feelings. All feelings. All feelings. Yeah, I would say all authentic emotions. Let's distinguish that. Lasts for as much, you know, up to 90 seconds. Now, you know, if you're grieving, for example, a loss of a loved one, it may— there may be lots of waves. But it's actually— there's two things. There's a few things to talk about if you want to go down emotions. One is, you know, what you resist persists, right? So the reason most people experience moods and emotions that seem to last a long time is because we don't want to feel it initially. We stuff it down. Then we go into our heads and we kind of ruminate or distract ourselves and we feel it a little bit more than we might think about it. So we get in these cognitive-emotive loops that can last a long time, even years. But the, the root of it, like to pop the balloon, it's just, can you fully let yourself feel the feeling? And that's such a powerful experience. And the other thing I learned this from Joe Hudson, who's a wonderful coach. Is an emotion plus resistance is a fundamentally different experience than the emotion without resistance. But because most people label fear, anger, and sadness as negative and bad, they've never experienced them without resistance. And so they, they, their visceral experiences, those are painful emotions. They're not painful. It's actually the resistance that's painful. But it's like a self-fulfilling cycle because if you think they're painful and you resist them, you get to be right, which is so often the case with these phenomena, but you experience a lot of pain. So, that's something I really work with clients on is, can you just allow yourself to feel what you're feeling? Can you welcome it and notice one, just what it's actually like? Like often people find that if they really welcome fear, inside of it is excitement, right? There's this quote like, "Fear is excitement without the breath." You know, it's like Both are just a way to be with uncertainty. There's like an energy of uncertainty when we fill the vacuum with imagining what we don't want, we feel fear. When we fill the vacuum with imagining what we do want, we feel excitement. But they're very close emotional states.

So, this is a really good primer on conscious leadership. And I want to pivot a little bit because there's some other topics that I want to get into. Safe to say that this is a really powerful tool for entrepreneurs. And if you haven't read the book, The 15 Commitments of Conscious Leadership, highly recommend it. It's probably my number 2 most recommended and given away book out there. My number 1 most given away and recommended book is The Untethered Soul by Michael Singer. You get those 2, you do everything they say, and your life is going to be substantially different than it was before you read them. But I want to shift now, Dave, into another thing, which—

Can I add one? Yeah. I wrote something recently or did a video recently, the 3 books every entrepreneur must read. So we're very aligned. 15 Commandments of Conscious Leadership, The Untethered Soul, and The Power of Now, which I imagine you like as well. Okay, please go ahead. Yes.

I was just going to bring up another thing that comes up for entrepreneurs, which is this feeling. We all know the saying, it's lonely at the top.. Right. And everyone tells us, oh, you're starting a company. It's so lonely. You're the CEO. There's no one you can talk to. You internalize all this stress. Frankly, sometimes you just internalize the good too. You internalize the good and the bad. You don't have that ability to connect with others. Many entrepreneurs want to build deep, meaningful, authentic connections with other human beings, particularly the people that they work with, but they don't know how. They don't know how to do it. They don't know how to be in the balance of, well, yes, I'm the boss, and there's certain things that I'm doing versus, hey, these people are working for me, et cetera. So that's one element. And they also don't really know how much should I verbalize about what's going on for me and the stresses that I might be facing and stuff like that. And I'm curious, because I know you've worked with so many really well-known entrepreneurs and CEOs. When folks come to you with those sorts of questions about how to balance this and how to create real connection with the people they work with, what do you typically recommend?

One of my favorite quotes is from Chip Conley. He's running the Modern Elder—

Yeah. He's also been on the podcast. Yeah.

Oh, okay. I love Chip. He says, the most neglected fact in business is that we are all human. And so I think, one, there is a— I think a notion that we need to be inhuman, like we need to be invulnerable, right? And I'll draw a few distinctions I think will be helpful here. One is like conviction versus certainty. I think there's a really important distinction because I think what often can stop CEOs, founders, from being authentic is they feel like they have to be— they have to have certainty, they have to know all the answers, they can't admit when they don't, right? Um, they can't admit vulnerability, that they have any fear or emotions or anything like that. And I think— well, I think it isn't true. I think that like the more connected your team, the more trust there is, the more powerful you'll ultimately be. Like trust is a really powerful, I guess, factor of production, for lack of a better word, right? Like teams can move so much faster together when there's high trust because if you just assume good intent, you don't waste all this time and energy and drama You know, and what creates trust is vulnerability, right? I'm willing to share something with you that's scary for me to share and see that you hold, you honor that by not using it against me, right? That's actually, that's generally what, you know, what creates the kind of connection and trust. So I think it, um, you know, like everything, there's extremes. You can go too far in either direction. I think most CEOs go too far toward thinking they have to be invulnerable. I think this was one of Pat Lencioni's like 5— I forgot— 5 Temptations of a CEO, which is a decent book as well, was like that I have to be invulnerable and therefore I can't be real with my people. I do think it's important to have conviction. Like, I think like leaders create a compelling future for their teams to step into. So I don't want to step over that because I think to be a powerful leader, you're the holder of the vision, right? And the more conviction you have, again, many of these things are self-fulfilling. I believe the most successful entrepreneurs are the ones with the most conviction. But if you feel like you have to pretend certainty, I know we're going to get there. I know how we're going to get there when you don't have it. You know, people smell that, right? Of course, you can't have certainty about the future. It actually ends up being off-putting. Whereas if you're like, guys, I don't know all the answers. I believe in us. I believe we're going to get there. I see us getting there. Like, that's, I think, the most compelling way to be as a leader. And that invites vulnerability. I'm scared too. Of course, I get scared sometimes. And I know we have what it takes to get there. So, it's the both/and, right? I think the lie is that it's either/or. Like, either I can be a strong, leader or I can be vulnerable. I think the strongest leaders are vulnerable and have conviction and willing to stand for, like, we can get there, clear vision of the future.

Awesome. Yeah, totally agree. And by the way, every time I've done that, then that's how people respond, right? And you're like, oh, good. Okay, this works. And building trust and showing that I'm human You know, lo and behold, it gets reflected back to me and that winds up being something very, very positive.

And humans have emotions. Yeah. Like, it seems to be a general social kind of, you know, professional agreement that we're not allowed to have emotions or show emotions at work. And I think there is an absurdity to it. You know, again, you can go too far in either extreme. I often ask leaders, like, are you wanting to share that feeling for you or for them? Right? Because I think there is a certain responsibility as a leader to, like, take care of yourself and serve your people. Right? They're not— I don't— I personally don't think, you know, they're, you know, come to me, right? Come to peers. Like, there are ways to— I want everyone to have the radical support they need. But generally, I think leaders' primary function is to serve And so, there's times where like if you're just kind of trying to unburden yourself of the fear, that's really different than, you know, I want to be vulnerable, I want to connect with my people. I think me letting them know that I have some fear will help them give them permission to feel their fear. So, like every, you know, leadership is the art of discernment. So, you know, it's, there's not, there's never like a one way and one rule, but can you discern moment to moment like what best serves? What best serves our vision, what best serves people. And I find the more you're present, you know, above the line, the more clear you are about what best serves.

Now, share with us some of the stuff that you're working on. And I know that you've got a number of programs. I know that you live in a great place in Idaho, and you've got some plans for a bunch of CEOs and entrepreneurs coming together in January. But tell us more about all the stuff you got hopping.

Thank you for asking, Alex. So this year for me has really been about serving more, you know, serving more humans, serving more entrepreneurs. I've been for 15 years primarily coaching CEOs, founders one-on-one, and just have been feeling inspired and called to serve more people. So last fall I launched a, um, a course called The Inner Game of Entrepreneurship. That's like an online 3-month program I have cohorts going, you know, constantly. It's all on my website, davekashen.com/courses. Um, and so I have that going on an ongoing basis. I'm working on kind of building more video-based content for people who can't attend live. Um, you know, building a whole kind of membership model. Really, it's all like, I just want to serve more and more entrepreneurs because it's just, to me, it's such a noble, meaningful, and challenging pursuit. So one of the things I'm excited to do, I live in this beautiful place in Sun Valley, Idaho. I find it so energizing, revitalizing. Frankly, I've been a little bit jealous of like Allen Company when they, you know, they bring in all like the CEOs of all the Fortune 100 companies. And I'm like, what if there was a version of that for entrepreneurs? So I'm creating, for now I'm calling it the Sun Valley Founders Retreat. First one, you know, will be in January 2025, and I'll continue to, you know, create future ones, just to like, like fully immersive experience for a couple days where we, you know, deeply connect, do the exercises that I have found reliably and consistently make a difference for clients to really inner game work, right? Shift limiting beliefs, look at identity, look at patterns that are in the way, get fully present, and then start to, you know, give ourselves permission to dream and envision and then get clear about who do we need to be and what do we need to cultivate in order to, you know, create that future. And then, you know, I love to ski. A bunch of entrepreneurs that I know love to ski. So, as a way both to, like, continue the bonding, connecting, playing, but also to integrate learning, I find if you get in your body, you can actually integrate the shifts because a lot of them are really deep unconscious energetic shifts. So, we'll kind of play, we'll ski for— so, it's Thursday, Friday, and then Saturday, Sunday, spend the weekend skiing and dining together. And so, I'm just like when I think about and imagine a group of amazing heart-centered entrepreneurs coming together as I know you've done in this beautiful revitalizing place with physical activity and deep work, it's like, this is the dream event that I wish existed when I was doing a startup. So that was what prompted the creation of that.

Sounds like a winning combination. And for me, when I do these things, I've done Conscious Entrepreneur many times and other workshops and stuff, the number one thing that people take away is this feeling that I am not alone. And so coming to this thing and coming to Sun Valley and realizing, Wow, there's a lot of other people who are also on this journey, who also have these same feelings that I do or the same situations that I do, et cetera. Realize I'm not alone is a huge thing. Well, I'm really looking forward to the event in January. Congratulations on putting it together. Thanks so much for joining us here today for this really deep look at conscious leadership and all these other tools. And for sure, we're going to have to continue this conversation. In a follow-up episode. But Dave Kashen, thanks so much for joining us today.

Thank you so much, Alex. It was a joy to be here.