When You Don’t Know What’s Next – You’re Expanding and Growing

Welcome to Heart of Entrepreneurship, a podcast where Dave Kashen, my longtime coach, and I talk about building businesses with heart and building ambitious companies from a place of love and creation and joy, as opposed to the common narrative, which is that you have to do it by eating glass and getting punched in the face and all the other memes about how hard it is. And that's not to say it's not hard, but just that we think you can do it from a different place. So we here, we talk about frameworks, learnings, coaching, all kinds of things regarding that topic. I got a good one today, I think, Dave.

All right.

Before we do it, I wanted to share— there's a guy here in Missouri named Brent Beshore. Do you know Brent? Have you heard of Brent?

Yes, I know he is.

He has like a cool private equity, really long-term approach. And he's a really— he's a guy with a lot of faith, which, you know, resonates with me. He posted this thing yesterday where he said he was praying and he got this message that at any given time, he— I think we all of us have 10 problems and 10,000 blessings. Mm-hmm. And of course we tend to focus on the 10 problems versus the 10,000 blessings. But the other thing that was interesting, he meant— I was texting him about it. He's like, we also have this mindset of like, oh, once I get rid of this problem, I'm good.

Yeah. Then, then I think I'll be content and peaceful.

And yeah, I just thought it was such a great framing of so much of the work we've done and these things of like, oh, I feel like I'm always just gonna have 10 problems, but I also have 10,000 blessings. And let me look at it that way. And let me not expect that just cuz I have a problem gone, then something, you know, then I'm, then I'll be free. Like, it's just, it's just the way it is. Anyway, I thought I'd share that with you cuz I, I found it.

I love that. And it, yeah, it just speaks to. It matters what we focus on, right? Do you focus on the 10 problems or the 10,000 blessings? And most people have this like narrow vision and all they see is the 10 problems. It occurs as if life is so filled with problems and difficulties. And then it's, it's even more comic because I think I've shared this quote before. Um, I heard from my friend's grandma. She said, I've, I've had so many problems in my life and none of them ever happened.

Right.

So not only 10,000 blessings, 10 problems, but even the 10 problems are more just ones we're imagining will happen than actual issues or challenges that we're facing.

Yeah. I love that. On that note, I wanted to talk today. I'm guessing this is a very common thing that comes up in coaching. I know it's come up in our coaching sessions. And it's, it's like one of those things that I think founders maybe talk about in really close circles, almost never talk about with their employees or broadly, and I'm sure talk with their coach about, which is they get on a phone call and they're like, hey Dave, I'm stuck.

Mm-hmm.

I don't know where to go either. I don't know where to take the company. I don't know how to deal with this problem we're facing. I don't know. I, I don't know how to deal with this person in the company that, that's, you know, I'm stuck. I feel really stuck. Yeah. Yeah.

Those, those conversations usually excite me because like, ah, this client has reached their edge, right? Like their growing edge. And so, you know, if they were within their comfort zone, they wouldn't feel stuck because they'd be like, I know how to do this. And so they've hit their edge of what they currently know how to do or um, a feel, you know, which feelings they're comfortable feeling, right? And so one, already that's just like, that's a powerful reframe even right there. Yeah, yeah, even right there you go from, oh God, I'm stuck, to like, yes, I'm stuck, you know, like, all right, I hit, you know, it's like I hit a wall, right? Yeah, I feel stuck because I hit a— it's not obviously not an actual wall, but like I, I hit some, you know, boundary to my current kind of understanding of reality or sense of what's possible or just knowledge base, you know, ah, there's so much to explore on this topic. I love it.

Uh, it's funny you say that, by the way, the first thing that came into my mind just to share it is, you know, Ricky, my son, and he is, you know, his intelligence is genius level.

Yeah.

And he's got the, like what they call the genius trap, which is because so many things come so easy to him, when something doesn't come easy to him, he gets really frustrated really fast.

Yeah.

And it's a lot of stuff like, I mean, a specific example right now, he's 10, is like we're trying to teach him how to to manage his hair. His hair goes to his knees, he's never cut it. It's hard to manage, it was hard to manage, it's still hard to manage as an adult for me, right? Um, and it's, you know, it's like fine motor skills. You have to twist your hair in a bun and tie, and it's like really hard for him and he gets very frustrated by it. And the reason, I don't know, it came to my mind because it's funny when you, when we also try to coach him that way, like, yeah, you're on the edge of your, like, you don't know how to do this and that's okay. And it's funny just to hear that back as an adult and go, yeah, that's actually a great way to to put it. Like when I'm feeling stuck, I'm just on the edge of my learning. Like I'm Ricky and I don't know how to do something.

And yeah. And, and, um, one of the most common patterns that I think founders and people like call feeling stuck is I don't know how to do something and I think I should know how to do it.

Right.

Which may be the same thing with Ricky, like, well, I can do all these other things. Why can't I do this? And, you know, in some ways it's just a microcosm of any, anytime you think reality should be different than it is, you feel this friction. But I think there's a particularly interesting example where it's like, and you might reflect, you know, where this happened for you. I'll do the same. It's like, you know, for most, for Founders, a lot of the things they're doing, it's the first time they're ever doing it. So at some level, it's like absurd that they think they should already know all the answers, but they do. Um, you know, many have, you know, gotten a lot of accolades and achievement by knowing the right answers. And so when they encounter a situation where they don't know the right answer, at least the voice in their head says, you should know how to do this. And that's, I think, part of what creates that feeling of stuckness, this like tension between I don't know and I should know. So, you know, often my first move is, well, can you just be with, I don't know.

Yeah.

Right. And you know, there's great metaphors, like, you know, if your cup is already full, there's no room for new knowledge, right? New learning.

So yeah, I can imagine we posted this story yesterday. Andrew loves this story where, and you know, the story too, where I saw Rick after he bought a billion-dollar business, publicly traded company, and he goes, We have no clue what we're doing, Jesse. And I thought he was being faux humble at first, and then I realized—

is Rick Elias.

Rick Elias. Yeah. The founder of Red Ventures. And then I realized, no, he was, he was doing that very specifically. He was trying to create room for himself. He was talking to himself.

Yeah.

Because when he, when he stated that position, he's like, oh, and I, one, one unlock I always, for me, I love, I don't know, because I find it really liberating. Yeah, because I like to figure stuff out. I enjoy the process. I think most founders enjoy like the process of unpacking something or running, you know, pulling on a string. And the second it's reframed, you go, oh yeah, I don't know. Okay. But, but now to me, it galvanizes action when you say, I don't know.

Ironically, right? The thing, the thought like, I should know how to do this, right? Actually gets in the way of action. You just kind of get stuck around. I should know, but I don't know. Versus God, I don't know, it invites a state of curiosity and wonder from which ideas emerge, you know, to try and experiment. I've used some of those.

So one pattern here, I guess, is just to start to capture them is the first one you said, which is expecting yourself to know when you don't know and then getting frustrated and that creates stuckness. So one way to free yourself from that specific pattern is to just get like, enjoy the liberation of, I don't know.

Yes. Including, you know, as we alluded to earlier, the, the reframe of, oh, oh, I hit my growing edge.

Oh yeah. Yeah. This is exciting. This is good. This is a good thing. I'm growing.

If I feel stuck, it's like, oh, maybe I've hit some edge of my development and that means I'm going to expand beyond my previous limitations. So, um, you know, just seeing stuck as a problem is like this self-fulfilling it's like, oh, it's bad that I'm stuck. Now you're stuck around being stuck and, you know, right, right, right, right. So that's a big piece of it. And usually there's fear. So that's worth mentioning as well. You know, we're alluding to curiosity and wonder of like, oh, I don't, you know, I don't know. I mean, it's funny, often when I do trainings, I actually request, you know, and invite people to be in beginner's mind. You know, a lot of people have heard this term, you know, could you be in beginner's mind? And most founders and CEOs think, you know, again, I should know all the answers. It's the opposite of beginner's mind. It's like, I should already know all this, et cetera.

So, yeah, fear is the second, I think a second major stuck pattern. Like for myself right now, we've been talking about like, we've been starting businesses at GatewayX, as you know, and now like, oh, should we buy businesses? And like, I think on the whiteboard when I'm like whiteboarding, I'm like, oh, this sounds fun. Yeah, like I know how to do this. And then like the real commitment around it, we've been getting into it and I'm like, and I find myself, oh, like, I don't want to talk to that. I don't know if I want to do that. Like, and I think the other thing about it for me and then probably for a lot of people is sometimes it doesn't— it's not obvious that you're stuck. Like for me right now, it's like, oh, I got my— got a lot of other things with these other companies going on. So my calendar's filled there. I'm like doing the AI stuff and it's like, I'm clearly not like I— you and I were talking about this last week. It was like, okay, I need to put a thesis together. But I've talked to like all my buddies who do M&A and do PE and they're like, well, dude, the way you do that is you write a page, which I've done about AI and services, and then you go and talk to like 20, 30 companies and then you refine it. And that second part, I'm like, yeah, I don't like my calendar just seems busy. Like I haven't been able to make the time for it. And it's— I think you and I last week were like, oh wait, it's actually some fear. Maybe some fear you don't know how to do it or from fear that you just— it's a different risk profile of the things you've done. And I think that fear definitely gets people stuck, gets me stuck for sure.

Yeah. I just thought as you were talking, it's funny, a lot of founders show up with, um, time management as their kind of presenting issue. I want help managing my time. I need a better system. I need to understand my priorities. And really what's happening is exactly what you just said. They, they end up spending time on the things that are comfortable, easy, they know how to do. They get, you know, they could check the boxes and avoid doing the things that they actually have fear around. And that's often the real issue. So same thing with stuckness. It's like when there's a feeling of stuckness, one, there's probably some fear around whatever it is they're trying to do. And two, they're probably not actually feeling that fear or welcoming it. So part of stuckness is the, there's some feeling arising. And they're resisting feeling it. And that actually creates the experience of stuckness. 'Cause it's funny. It's like, are, you know, are they really stuck? I mean, that's also just like a, an inquiry worth, uh, you know, endeavoring in when you feel stuck. It's like, am I actually stuck? I think sometimes about like a river, you know, like a river will flow mightily and then there'll be a part where, you know, the banks widen and then it'll just go real slow and then it speeds up again and So sometimes it's just like, oh, we think we should always be moving quickly towards something and we don't honor like the ebbs and flow.

Or sometimes you're in just a chill period.

Yeah. Or yeah. Or like we want clarity, you know, and I often use this metaphor. 'Cause sometimes stuckness shows up as like, I'm just not clear. Right. Like if I was clear, then I would, I wouldn't be stuck. I would know what to do, but it's unclear. And they often use this metaphor. I happen to have one in my hand of like, imagine like a water bottle filled with like, um, water and sand. Right. And so it's very murky. It's not very clear. And then what a lot of people do is they then like agitate, like, ah, I'm not clear.

I wish I was clear.

I need to be clear. And of course that makes the sand, you know, makes it even more murky. Whereas the, you know, the solution often is like, just set it down., right? And let it get still and calm. So being with the, okay, it's not clear right now. And even like inside yourself, like if you can kind of slow down, get a little bit more still, like sometimes clarity will emerge, but trying to force clarity and be, I need to be clear. And I fall into this trap as a coach too. Sometimes I'm like, oh God, this client wants to be clear. I gotta help him be clear. You know, instead of just like, oh, you're not clear. Like, What's that like and what's in the way and just like exploring it. So there's something there really, you know, there's a linkage there around like clarity and stuckness. Um, so just to—

and so for when you, when someone isn't clear, your clients and stuff, obviously you can help them explore it. Is it, is it always just like kind of meditate? Like, is it just sit down or what are the other things you would tell someone to do to allow for that stillness to, to take hold?

Yeah. So still, well, so there's stillness, which is meditate. Yeah. You can meditate and slow down. You could like bring a question into meditation. Um, even just letting go of the thought something should be different than it is, or specifically I should already know, you know, all that is—

some people exercise, I think, or like nature walk.

I like nature walk. Oh, I was out on a run or a walk and I had this, you know, epiphany, or I was in the shower and I had this Epiphany. So yeah, ironically, when we're like trying to figure it out, often we're, that's more of like the agitation that gets in the way of clarity versus, um, do something that shifts your state when you're not even thinking about it. And sometimes, uh, clarity will emerge. Like insight is caused by like two weak signals connecting. And so if there's noise in your mind, your, your brain can't like hear the weak signals enough to connect them. So that's a whole like category is like get, get still, get quiet, you know, shift state. But there's a, there's this other category to think about too, which is, 'cause often the thing people, well, what people think they're not clear about is what's the right answer. Now it's really hard to be clear on the right answer because the right answer is almost always unknowable, right? Life is not a math. Puzzle, you know, 3 times 7, like that has the right answer, but pretty much everything we do, it's unknowable what the right answer is. Even after we do it, whether it was the right answer, right? All we can do is experiment and learn. So I think what is more true is they're not clear about what they really want. We've talked about this. Like I spent a lot of time trying to support clients to go from what's the right answer to what do I really want? 'Cause I believe that your authentic wants and impulses are the right answer for you. Right?

Yeah. Let, let's, I think there's so much to unpack here and this has been a journey for me too, as you know, like the, let's start with the unknowableness of things. Okay. Because I think for me as a business person, for most of my, well, at least half of my business career until I met you, I was like, no, like we're gonna, we're gonna, what's the market size of this opportunity and what's the market size of that opportunity and likelihood of success and, you know, and math and then we're going to choose one and it's going to be the right answer. And yeah, you came along and you were like, dude, you just can't know. And I'm like, no, what do you mean? Of course you can. And I think now I've, I've come around to the perspective, your perspective around this or like this idea. But like, can you talk about it? Because I think most people, most founders, like literally being right is like one of the— I mean, one of Amazon's values is like good leaders are right a lot. Have you— I don't know if you've seen that one.

Interesting.

And I know what they mean by it, which is like, you gotta make a call and the call has to come true. But let's talk, let's unpack this, 'cause I think this is an interesting one for a lot of people.

Yeah. Well, one, I can see that perspective. I, for some reason I was thinking about investing and like, yeah, if you make accurate predictions, you will make more money than if you make inaccurate predictions. If you're in business and you predict the way, you know, something will go. And you're right, you're more likely to have things go the way you want. Now, um, that might be a local maximum because it's possible there was some other step function that you could have created if you had been less focused on being right and more in a state of curiosity and wonder. Um, let me share this, this story that just because it's so, it feels very relevant and it was so recent. I was talking to a client, I think it was yesterday, and we were talking specifically about, and I think this is related about like, we could call it want, you know, wants versus shoulds, you know, and like forcing something versus following your wants, which is kind of the theme here. Then we can get back more into like The Unknowable, but I think this relates to it. And he was saying how at one point his company was kind of on the brink, you know, of failure. And of course, like most founders, you know, that stirred up a whole bunch of shame and fear. And he just hustled and, you know, grinded and like found a way to get money. They were going to run out of money. He found a way to get money and keep this thing going. So now a couple of years later, he's in this, you know, he's still in the company. It's still probably not the best. Yeah, obviously I won't name names or anything. Yeah, it's probably, it's still probably not the best market, the best, you know, business, but he's, he's kept it going. So by most founder standards, it's like, great. You know, we give him the trophy because he persisted. And he was reflecting, you know, cause we were talking about that, like following your authentic wants versus like forcing something to happen because of external pressure, not wanting to look bad, be embarrassed, feel shame, internal or external, but like something that's kind of putting you off from integrity, from your authentic wants. And he's like, you know, I bet if I had just let this thing fail, it was like 3, 4 years ago, I probably would have been ahead of the game in AI. You know, I see all these people, you know, less experienced, less, you know, maybe less savvy than me raising, you know, a $10 billion valuation. And, you know, so it's a little, this is like the unknown, the part of the unknown, right? And maybe, maybe like the local maximum that we're pointing to is, you know, your mind gets attached to like, I've got to make this work or else I'll fail. Or in this, you know, it was a common founder experience. And in that example, like, did we know that, you know, OpenAI was gonna have this huge breakthrough with the reinforcement learning. Yeah, of course not. And, um, if you have—

there's an uncertainty of the future that—

of course.

Why do we get stuck? Like the— so, so why do so many founders then believe they can make the— get the right answer?

Um, I think it makes us feel a sense of certainty. Which makes us feel safe. I mean, we could, we could expand that to just why do humans— like, it's, it's kind of absurd how certain we feel, right? Like, like, who knew COVID was going to come? Who knew, right, right, you know, Russia was going to invade Ukraine? You know, Trump was going to do all the things he's had— like, like, there's so much happening that we absolutely could not have predicted, but somehow we feel safer when we believe we can predict what's going to happen. Like if you think about, I don't know, like beyond a couple days or weeks, like in any slightly longer term horizon, you know, if you go back a year or 2, 3, 5 years ago, like what you thought would be like what your life, what you thought your life would be like, what would be happening. Most people, if they're, if they spend the time to actually reflect on it, it's totally not what they predicted.

Right.

Because we have no idea really. But I think part of it, we have this core need for certainty that just, we have a need for uncertainty too. So it's a funny dance.

So what's the, but what about the opposite? Like why, why then, why, like to use a stock example, like why even worry about which stocks to pick then? What's the, you know, Why even try to be right then if, if you, if you, if you can't be, if it's not possible?

Um, well, we, you gotta do something with your time. Might as well play, you know, there's some games that we choose to play. I mean, well, if your goal—

I thought you were gonna say something along the lines when, when I asked you that question in my head, what you were gonna say back was Being right is great and it's good to try to do it. It's just that when we get attached to wanting to be right, which is, which is where the, all the suffering comes in and, and like the—

that's true too.

Like in other words, like one of the ways we get stuck is we're like, we have to get the answer right. And then similar to the, I don't know thing, you're like, well, it's impossible to actually know what's gonna happen.

Yeah.

And, but we, we get attached to like, oh, I'm gonna do all these calculations to make sure I get the perfect answer. And that has nothing to do with whether the answer's gonna be right or not so much, but kind of what you were saying earlier of like, it just makes us feel better because we're so attached to being right or that we think we're, you know, we think we need to be right.

It was coming up for me. If I had to choose between, um, more certainty, better prediction of what's gonna happen, and more resilience and capacity to be with uncertainty and change. I'm voting for option 2, right? Because I think life is very dynamic. I mean, especially now we're in a period of like rapid, you know, change. I think it's possible, like life 5 years from now will be unrecognizable to our former, you know, our current selves. So, so that's one. Place, I want to just have us think about that distinction of like trying to be right and get more right and be better at being right and be more certain versus expanding your capacity to be with uncertainty. I think that's a more important skill for leaders because, you know, if you can trust your sort of future self to handle whatever actually occurs, then you don't need to predict as much of, you know, as much because you'll take—

it's somewhat of a defense mechanism.

It's so much of— yeah, it's like if you could trust your future self to handle your future problems, you wouldn't need to do as much planning and prediction. You could be more in flow. Now, that said, in investing, in business, is it useful to recognize patterns and predict as best you can what's going to happen? Of course, right? You'll be more successful You know, the, even when you do, you know, there's exogenous things that occur, like, like that success is never permanent. So like, okay, I got, you know, I got the, even like the best investors, like they got it right and they got it right and then they got it right. And then all of a sudden COVID hit and oh my God, their entire, you know, 10 years of portfolio or long-term cap. No, no. What was that? What was that? Uh, the Nobel Prize genius economist who had like crazy returns and then the thing collapsed.

LTCM.

Yeah.

Long-term capital management.

It was long-term capital management.

Yeah. Yeah.

Like really, those are some of the most brilliant predictors, you know, of the future ever in humanity. And they were right. And they were right. And they were right until there was something they missed. And then they were wrong.

I mean, you coach hedge fund people. Like, what do you, what do you, what do you tell the hedge fund people who have, because I assume it goes both ways for them. They think they're a genius and then all of a sudden they think they're an idiot based on the way the output put of their decision happens versus—

Yeah, first thing I try to support them with is it's not personal, right? Like where it gets troublesome is when you make it mean something about you. Oh my God, I'm a genius. Like you're saying, because look, I've compounded 28%, you know, for 5 years. Oh, I'm an idiot because I missed that, you know, the Fed was going to do this or that.

Yeah. Right.

Um, I really like the idea of separating your being from your doing. Mm-hmm. Like, that's a big core distinction to make, that like your being, who you are, is already whole, worthy, you know, like it's, it's this completely separate thing from then you go do some stuff, including make some investments, make some decisions. So of course. You're going to try to make the best decisions you can with the information you have and your own biases and patterns, et cetera. And sometimes you'll get it right and sometimes you won't. And the only thing you can really do with the past— well, you can do a lot of things with it. Only thing I think it makes sense to do with the past is learn from it. Right.

Right.

And this is the whole conscious leadership thing, 100% responsibility versus self-blame distinction. It's like responsibility is, oh, I wanted to continue to have great returns and we had our worst year ever. So I didn't create the thing that I said I wanted. And I'm, you can, if you can see me, I'm smiling because like without any self-blame, that's not a problem. It's just, it's just the facts.

Right.

And given those facts, given that I said I wanted this, but I achieved something different. The only thing that really makes sense is to get deeply curious about how you created that. Take as much responsibility as you can, not more than you can, like there are exogenous things, but around what was within your control and learn from it so that you can do better at, you know, achieving your goals in the future.

But for founders, this example of a founder kind of deciding between, let's say, 3 strategic directions or pivots or whatever for the business.

Yeah.

And then you'd say, you know, it's unknowable. Like you said, you could pick the mathematical answer could be this one and then something could change, whatever. Can you talk about this distinction of saying like, well, this is what's right versus what I want?

Yeah. I think that's it.

Yeah.

And I didn't fully flesh it out, so it's a good— so we talked about stillness as like, you know, one way to invite more clarity as well as patience. The other way is to, I'll use a metaphor, like build the muscle or rebuild the muscle of wanting. So again, if you think about kids, you think about your kids, they're pretty clear what they want, right? Dada, Papa, I want this, I want, I want, I want that, I want, right? Like they want like crazy. And then, you know, as parents, as well-meaning as we are, sometimes we're like, oh no, like You're being selfish. You don't want that. Like, no, you don't, right? Either like, we'll, we'll sort of teach them that they don't really know what they want or that wanting is selfish or in all sorts of subtle and not subtle ways. We inadvertently squash wanting and life does too. Right. You know, and so most founders, most clients I meet with have atrophied their wanting. Myself included, by the way. One assignment that I was given by a coach not too long ago was basically go have temper tantrum, like a 5-minute temper tantrum, like on my bed, like, no, but I want only these kind of clients and I want to grow this way. And just to like allow the wanting that got, you know, maybe the temper tantrum got squashed when I was a kid and that like depth of wanting as It's like to bring that back. And so I think it's like a really underappreciated, we could call it skill or muscle to build as a human, as a founder is the muscle of wanting, like really allowing yourself to tune into what is it that I really want? And again, you know, a lot of people will hear that as, oh, oh, this is a problem that I don't know what I want. And now, Again, now we're stuck again versus, oh, this is, you know, if I was like, oh, I want to bench 225 pounds.

Right.

I would be like, what's wrong with me that I can only bench 170? I would just add weight and add weight and add weight. And maybe a year from now I could bench 225. So similarly, like I'd see this as a journey of like cultivating the wanting muscle.

Well, and I think that there's a, the, it's such an interesting I, my experience with this for a long time, and I think with a lot of founders is like, again, like you're trying to take a test in college or something and you're trying to get the answer right.

Yes.

And meaning right for what the world thinks. And I remember talking to Rick Elias again about this, about strategy, and I was like, well, here's the market, here's how we have to attack it. And he's like, but it doesn't sound like you actually wanna do that. And I'm like, but who cares what I want? This is what's right for the business. Right. And he actually interestingly is, and this is like always reinforcing when we were working together in the beginning, he was like, He was like, dude, you can't build a business you don't want to— like the founder and the CEO and what they want to do. If you're not excited about it, if you don't want to run it, it doesn't, it doesn't matter how right it is. Like it has to be the thing you want. Strategy and the founder's desires are in like inextricably linked. And once that was like one of those things, once I saw it for myself, I just couldn't unsee it anywhere.

Yes.

And I meet a lot of founders. I mean, and because they're like, oh, they're trying to get right for the VC pitch or they're, What they don't realize, by the way, just to call it, the founder who, who knows what they want. Like, you think about Steve Jobs, for example, like he was not trying to make it right for the market. He's like, this is what I want. This is what I think is right. Like, this is what I believe.

Yeah.

And then the whole world follows him basically. And the VCs, if you talk to like Vinny, my brother, they, there's VCs, they just, they really wanna be led also. They want a founder who's like, this is what I want, this is what's gonna exist. And then everyone's like, great, we're on board. Like versus, A lot of them again, make the dynamic of what do they want to hear? I'm gonna like say the right answer that they want to hear. And then that, that literally turns into company strategy and like it becomes a, it becomes a way a business is run and it's such a huge sort of endemic you see in, in the, in the company building world.

I love that Rick said that to you. It resonates really deeply for me. 'Cause I mean, think about how much friction that creates if you're, you know, for the next several years, you're basically forcing yourself to do something you don't want to do because you think that's the right strategy.

Right.

And you know, people talk sometimes about like founder market fit and sometimes they really mean, oh, well they have experience in this market. But I think that's sort of what you're pointing to is like, is this a market? Is this a playbook strategy that you are truly excited about? Right. And the whole thing, because you can see how it, how self-fulfilling, like if you meet someone who's genuinely you know, some people are good at faking it, but like genuinely excited about what they're doing and passionate. Like one, that's just attractive. And you know, it's like this infectious energy that draws, you know, talent and capital. So it's like, it becomes sort of obvious that that would be self-fulfilling. And then, you know, how much of, of success of a founder is based on just their energy.

Yeah.

Right. It's like, Again, and again, if you're forcing yourself to do something that's not authentic for you, it's going to just drain your energy and drain your energy until you're burnt out. And then, you know, I've made this comment before that like startups don't actually fail. Like the real reason startups fail is because the founders run out of energy to do it.

Right.

I mean, I've, I've seen founders persist for years and years and years, you know, and like survival bias eventually make it. Because they just authentically, they just so wanted it that they, they could persist through that. And this is where I think we get, we get, it gets tricky because we extrapolate from that sometimes that like persistence is good, right? You should persist, you should endure, that's the good thing. And what we miss is no, no, the ones that persisted were the ones that actually loved the thing they were doing. And so it wasn't a hardship to persist. But we take the lesson that you should persist no matter what, when in fact sometimes the most courageous thing to do is to let go, like the example I used earlier, you know, founder, and, you know, be with the shame and the fear and the disappointment and the heartbreak of letting go and maybe walking away from the company or letting it fail.

It sounds like knowing what you want is so important to being unstuck. Yes. And people get stuck because they get stuck between, well, I, I, this is what I should do versus this. Should I do this?

Should I do that? Yeah.

Why don't people trust what they want in general?

Or why don't they know what they want?

No, why don't they trust it? I think a lot of people actually, I, I mean, to your point, there's tuning into what you want. There's actually building that muscle.

Yeah.

But then a lot of times I think there are people know what they want, they're like afraid to say it or, or they, yeah. Or they just don't trust it.

Or they think they don't deserve it. Maybe not consciously, but a lot of humans have this, you know, often from childhood belief, I don't deserve it, or it's only worthy if it's hard. That's actually a really common one. This is why a lot of people don't actually play in their zone of genius because they're like, well, that's just easy for me. Like that, you know, and we've learned and we have kind of this puritanical work ethic. You know, culture that like it's only worthy if it's hard. So then if it starts to feel easy or it's like, well, yeah, but I want that, but I, you know, I should do this. So I think that's part of it. There's this other thing I— tell me if this gets to your question, but I see happen a lot, which is there's a presumption of trade-off that is very, very, very common, especially when people have some kind of fear below the line, but sometimes not even just you know, if I, if someone's struggling with like, uh, what do I want? Often it's like, 'cause they're thinking in their mind, well, either I want to, um, have life feel like easy and like I wanna relax a bit, but I want my startup to be wildly successful. So like now I'm stuck between these two wants 'cause I want to kind of take a break and, you know, so that has me want to sell it, but I also want it to be wildly successful and fulfill his potential. And so the most common thing I invite them is, could you let go of that limiting belief that it has to be a trade-off? Because what I hear is you actually know what you want. You want to have ease and relaxation and you want your startup to be wildly successful. So it's really, they actually know what they want. They just don't believe it's possible. So they're kind of wrestling internally between this false trade-off of these two things that they want. That's one of my favorite questions.

But if Andrew was here, I mean, if Andrew were here, he'd be like, what are you talking about, Dave? What do you mean? You can't, I mean, I have the same issue.

I think we're talking about— you can't have it all is, is really—

well, like I, I want to like have my calendar open and whatever. And I also want to go build, you know, these companies and, and grow and maybe do some M&A and buy some businesses. And then like, and what are you talking about, Dave? Like, you know, you have, that's gonna like, that's not realistic. That's not realistic. That's a, how do you actually do? Yeah.

What's, Yeah, I believe you can have it all. I believe you can have everything you want. However, it is important to distinguish your actual want from like your strategies for getting what you want. Because when you go to the level of strategy, yeah, there are, there are some that real trade. If I said to you, I want to work, you know, 2 hours a week and I want to build a successful startup. Yeah, that's unlikely, I'd say. I mean, it's a fun challenge. I actually might, I'm intrigued by it, but let's just say it's pretty unlikely. So then I'd be okay, but what's behind wanting to work 2 hours a week? Oh, well, I want to feel a sense of lightness and freedom. Okay. So you want to feel lightness and freedom and what's behind wanting to, you know, build a successful startup? Well, I want to feel challenged and I want to, you know, see what I'm made of and I want Okay, so you want lightness and freedom and you want to feel challenged. And like, if you get behind the strategies and get to like underlying wants, um, from my experience, you can always find a way to have it all. And I mean, we could go deep with that exploration because I think our deepest wants are actually end up being for experiences that are already available to us without achieving anything, like peace and joy and freedom.

Um, before we go to that, I think the, the, I guess the practical advice there, or the pragmatic framework for everybody would be something along the lines of, I heard two things, or I think maybe there's like, one is to your point, like if you did just wanna work 2 hours a week and build a billion dollar startup, just being really extreme for a second, I think actually talking about how you would do it. And, and it's something I've seen for myself as well as others when they get stuck in the like, well, I want to do this, but like, well, what would have to be true? Well, you'd probably have to find a great CEO to partner with, right? Or like you'd have to start to think about, and I think what would actually have to be true is a much more interesting way to actually have that, to like, if you want these things that feel conflicting, asking what would have to be true to make that real is a, is a really, for me, like here's a funny example for me specifically. Like I don't, I generally have, don't raise money. Like I do all this bootstrapping. Well, if I just gave up, I just said, well, no, hold on. I, I could probably have a much, I could have more staff, I could have more things if I had more money. And I just have to give up the, like, raise the money, Jesse. And then, and then you probably could have a relatively balanced life, but also go build something ambitious in a calm fashion. And so I think that's one, one way. The other flip I think that I heard you say was you can also just go into what are you actually wanting that's underneath those things? And, and it may turn out just to be a different set of whats to get you your whys, I guess, is the way I would say it.

Yeah. I also, let me just reemphasize the point that often when we feel stuck or when we're not, when we think we don't know what we want, it's because we have some limiting belief that we can't actually have these two, these two different things we want, that they feel opposing. And when you ask, how could I have it all? Or even just recognizing that. You actually know what you want, you just don't believe it's possible. It's useful to go, okay, yes, I want this and this. Because if you're in this like, oh, do I want this or this? You just switch the end. Well, okay, you've probably, you probably do know what you want. Um, there is this other thread, by the way, I just, I want to pull on for a moment, which is anger. Um, oh, a lot of, for me, I'll just speak for myself because this is really valuable for me. You know, I learned growing up that anger was not good. My, my, you know, my parents were, didn't get angry as far as I could see, didn't express anger. I had a stepdad who did, and it was a very brutish way. And so I was like, oh, that's a, that's bad. Um, but anger is the, is the energy of sort of boundaries. And anger shows up when what we want is not happening or, um, You know, and that could be like in a light way, like, oh, I don't, you know, oh, you guys all want Chinese. I don't really want that. I want, you know, I want Italian. Or it could show up as like boundary. This is not okay with me to be spoken to that way. And so for me, not accessing my anger and not allowing it was one of the primary ways I cut off my ability to attune to what I want or where my wants were not. Being met. So I think, I think that's just, I just want to name that because it is a part of how we end up feeling stuck is like, I disconnect from my wants because I don't want to feel my anger. And then I'm just sort of like not clear.

Right. That's a good one. So anger gives you wants. I, we only have a few more minutes. I want to talk about, I want to circle back to one and it's related to feelings. We talked about fear as a common reason to get stuck.

Yeah.

So Uh, why is it, you know, many times when I've been stuck and you've said, okay, we, and you and I figure out, okay, I'm feeling afraid of something. Your advice to me is like, feel your fear, Jesse. Let's imagine you make this decision and it fails or whatever you're afraid of. And you actually, could you even shake with fear or could you actually let yourself welcome fear? Why is that? And why does it work?

Yeah. And just, just to highlight the, the what of it is, is welcoming the fear. And then often what we're afraid of is some other emotion, like, oh, I'm afraid to then be disappointed if it doesn't work out or feel ashamed. So we might welcome the disappointment or the shame. I think, well, I think often what has us stuck is avoiding emotion. I mean, in some way it's a form of just resisting what is.

Mm-hmm.

And anytime we resist reality, we'll feel a sense of stuckness and friction because reality is flowing the way reality flows. And when we fight against it, just like fighting against the river, we feel that friction. Um, I think emotions are a particularly salient version of this. Because it's like, it's like the inner, you know, it's like there's energy that wants to move through our body. You know, in this case, in the form of fear. And when we don't allow it, it's like a, it's like a dam and like that energy is building up and we, I think we feel that very viscerally. So, you know, thinking, you know, most of the time when people say I'm stuck, and you said this earlier, what they're really saying is I've feel stuck, right? And so even if you just explore, well, how do you know you feel stuck? What, what, what even is that?

I don't know what to do next, or yeah, if I feel overwhelmed.

So there's the cognitive, like, I'm not sure. But if you, if you start to explore, um, what does that feel— what is the feeling of stuckness? Usually you'll identify it's actually like a feeling in your body. Because that's, I think, what people are really— when people show up, you know, with me and say, Dave, I feel stuck, whether they're aware of it or not, what they're really describing is I have some feeling in my body that has this stagnant kind of, you know, it feels stagnant. And what creates that is there's a feeling, you know, emotion is energy in motion, right? It's like there's this feeling, this energy that wants to move through our body. And we're literally fighting it. And so when we stop fighting it and let it flow, we feel unstuck, like we've released the dam. So I think it's a very literal, visceral experience of, of we actually are, it is stuckness in the sense that we are pushing against that energy, that feeling. And fear is the, probably the most common one I see founders not want to feel like we do so many things and, you know, spend so much time in our minds to try to avoid feeling the fear.

Um, but a lot of people, a lot of people would also like, they're afraid to let, they're like, it's a weird, I'm afraid to let go of the fear because the fear is actually the thing driving me. Why is that wrong?

Well, so I thought you were gonna say something else. There's two things there. One is sometimes I'm afraid to feel the fear because I think I'll just be swallowed up and consumed by it, or it's weak or something like that. And, you know, courage is not the absence of fear. It's feeling the fear and doing it anyway. Right. And there, so I just want to speak to that for a second because there's this misunderstanding, I think often that like, oh, those other founders, they're just, they're brave. They're just so, or really what we think in our minds is they're not scared like I am, but no, they're just as scared. They're just doing it anyway. So you feeling fear doesn't mean there's anything wrong with you. You feeling self-doubt, Nothing wrong with you. Embrace it, include it. Your question is, um, sometimes they don't want to like let the fear move through because they're scared that they think it's an asset, not a liability. I think it's an asset. And we've talked about this a bit, like fear-based motivation. Um, so yeah, if you spend your whole life motivating yourself from fear of failure or fear of not being good enough, it is pretty scary to let go of that because again, back to the unknown, you'll be in this unknown territory of, will I still be motivated? You know, and if not, what? Yeah.

Right.

Like, and it even gets to our identity, right? Many of us have identified as I'm a, I'm an achiever. I'm someone who's highly motivated more than most people in the world. That's why I'm an entrepreneur.

Yeah. Like you tell me I can't do it and that's what's going to make me do it sort of thing.

And if I told you, um, you were going to lose all your motivation, but even if that meant you'd experience inner peace, right?

Right.

If I told you the rest of your life, you're never going to be motivated to do anything, you'll be peaceful. Like probably that wouldn't actually feel so interesting question, but it would probably scare you. Gratefully, that's not a real trade-off. You know, from my experience, you don't lose all motivation. You still have creative impulses, but in short, The fear is that I won't be motivated and I won't achieve the thing that my mind thinks I need to achieve to feel the way I want to feel.

Yeah. The other way it shows up, just like if we can finish on this, but the, I've noticed even in the micro pattern, not the bigger one, let's, let's pull away from the bigger one for a second. Just like the, if I let go of the fear, I won't get the thing done well. And it's almost like a, I need this fear to stay with me, but I'm also stuck by it because I'm afraid of it. Or like, I, I don't want to move forward. And it's almost like the— if, if I feel the fear, like, it's like if I feel the fear, it's gonna come true. If I, you know, let's say I, I imagine the scenario where I make the wrong call and I make a bad loan. No, I can't even go there because I have to. And I think it's like once you realize that it's actually— I mean, you said this earlier, it's like you've stuck yourself in this way where you're not letting that, that thing through. Once you like imagine it all happening, you feel it all, then That's not real. That's just letting it actually fully have its place that it, that's there. And then you have the clarity to go execute effectively. Um, yeah, there's, there's a real belief sometimes people go, I can't think that because if I think that, then it's gonna happen. Or I have to think, I have to like swerve away from it in order to, to, to not let it happen.

Yeah. It's almost like a version of magical thinking.

Yeah.

You could do it on either way. Oh, if I, If I let myself feel that fear, then that bad thing is going to happen. And then sometimes people do this magical thinking around like manifesting. Oh, if I just visualize it, it's going to happen. And, um, I was thinking about like the Andy Grove Intel book, like only the paranoid survive, right? That's a real common, like if I don't think about everything that could go wrong, you know, then I'm going to miss something. That's the other aspect of this. Um, Yeah. What I would say is I would challenge, if you're listening, challenge you to run the experiment because, you know, in general, our fear-based stories tend to be wrong, right? If you think about how many times your mind has made up a story based on fear and then it hasn't, you know, talk about making good and bad predictions, right? Fear makes bad predictions, right? So, this is just a meta version of that. It's like, the story that fear tells me is if I feel the fear and let go of it, then I'll end up creating the thing I fear. From my experience, often the opposite is true. So I'd run the experiment. Like, that's the best way to get better at predicting is run experiments and see what actually happens.

All right. I think we ended last week on experiments too. We'll run that experiment and let us know, write into us or tell us somewhere on social that you ran it and tell us what happened. Yeah.

And just to be specifically like, welcome the fear instead of trying to solve it or, you know, navigate it.

Yeah. Like articulate and articulate and feel the fear around the scariest version of what you think could happen. And then see if it leads to that or if it leads to the opposite.

Beautiful.

Thank you, Dave Kashen.

All right. Thanks, Jesse.

See you, man. Bye.