Startup Therapy Podcast

Episode #64


Ryan Rutan: Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan joined as ever by Wil schroder startups dot com founder and Ceo will, are you okay with where you're at right now, man,

Wil Schroter: I'm not okay with where I'm at, It's a huge problem. Why can't I be

Ryan Rutan: okay? I know. What is that, what is it with us, founders, like, we just constantly have to be chasing something or we're not happy, we're like that proverbial dog in the ball, got to have something to chase, we're just not not in the mood to be happy,

Wil Schroter: you know, it kind of pisces me off if I'm being honest, because this whole time I've been working so hard for so long to get to that next milestone, right? You know, kind of get to that, uh, that next finish line and every time I get to that finish line, there's another finish line in another finish line and, and here's why it pisces me off. Like I, I love the race to an extent what I don't love is, I've never felt like when I crossed the finish line, no matter how amazing it was, like when I sold a company or do they all like the milestone things and I'm talking business course that you can do it, never really felt final, like it never felt like this level up that I always thought it would be and so I did what every founder does, just reset the goalposts and did it all over again to the exactly the same effect and at some point, at some point I and recently, you know, I just think about the last couple of years, I'm getting tired of resetting the post and here's why not that I don't love the goals, I love the goals and I love the pursuit. I'm starting to ask myself, when did I ever stop to actually appreciate crossing the finish line? And if the answer is never, by the way, it's never uh what the hell was I doing? What's the point?

Ryan Rutan: Yeah, it's tough. And it's, it's funny for me, I always notice that when I hear somebody else going through this, it's so easy for me to unpack that and see the flaw in the logic and you know, it's like, come on, man, slow down, you just did something great, take a minute to appreciate

Wil Schroter: it.

Ryan Rutan: And in the next breath I'm like, okay, but I gotta go cause I gotta go chase my next thing down. He gets the amount of hypocrisy involved in that is almost unlimited

Wil Schroter: for me. It's twofold, right? And again, and, and I don't want to project me onto other people, but I will say that I've seen this in countless other founders. So I'm, I know that I'm not alone for sure, but here's where I get stuck. Ah the whole point of risking everything and taking the amount of effort in and, and risk and all these things that it takes to do what we do as founders seems really pointless if we don't have a mechanism on the other side of it to enjoy it for what we just invested in. Yeah, right in I personally, and we can kind of get into this as we think through this and unpack this a bit, but I think there's another side of me that is equally terrified of being okay with that last goal, as if I, if I get off the hamster wheel somehow, that's going to be worse off, like my whole world is gonna implode if I don't keep chasing the next thing and and it's a dangerous place to be.

Ryan Rutan: Yeah, you know, well, it's, it's interesting if you've ever run on a treadmill, um and then you jump off the treadmill and you still have that sense of, like forward momentum, that's how we feel when we stop, right? Like we hit a milestone when we stop running, we stopped chasing. There's this kind of, it's not a it's not a good sensation, right? You still feel like I should be in motion, but I'm not, and it's disorienting and I think that right? Something very similar applies um when we hit a milestone as a founder within the startup and then suddenly we, you know, we can stop. Um but that sensation is just so strange for most of us,

Wil Schroter: I'd like to kind of decouple this as two separate kind of concerns. One is this whole notion of resting on your laurels and, and I I actually, and again, maybe this is part of the problem, but I actually do believe in that concept, like you shouldn't rest on your laurels. Like you probably should go back and kind of, you know, re up. But on the other hand, I'm kind of of the opinion that if you've never really found a way to enjoy any of your accomplishments, what's the point of the next one? Like if you already know that it's going to, it's going to be, you know, nonsensical. Then again, these are minor goals and were minor efforts to get to them. It's it's spending your whole life to win a super bowl, but having no way to enjoy the fact that you, you want. Like, I'm just waking up the next day saying I have to, you know, win the next super bowl and that's all that matters. And it's like, well at which point does it matter if you could never kind of stop and say uh, where I'm at is what matters. And what's next is great, but it doesn't trump where I'm at. I don't know how to contend with that.

Ryan Rutan: Neither do I. The other thing that's really interesting about that is that because we are typically the ones setting the goal post to, right? So there's not even like any type of a comparative, there isn't a benchmark that we can look at and say, okay, I cross the line. I wonder if that feeds into it. The fact that it's like, well, you know, I set that goal. One of the build company wanted to sell company did that. But you know, that was, that was, that was my thing. And so I is there some sense that because it's not defined by anybody else, we can constantly redefine that so therefore we feel like we have to, I don't know. But yeah, you're, you're absolutely right that this is one of those behaviors that we immediately re engage in, right? And this isn't just like, oh well I did it twice now that we've seen this 3456789 times with some founders and you know, to your, to your point around if it didn't make me happy the first time, why am I chasing? And maybe happiness wasn't what you were chasing to begin with. Um, but certainly you would hope that it would enter the equation at some point, right?

Wil Schroter: Well let me ride, let me build on this because you know, I'll give you some personal context here. And then again, I think some of the folks that are listening, uh, can can associate with some of this and can kind of, you know, dial it into their own world. But here's what threw me off uh, when I was a kid, I grew up, dirt poor, like crazy, dirt poor. And at that point I just figured if I was anything but dirt poor life would be shangri la, like that's all I cared about, right, I just want to be able to, to live in a house and have access to food was literally like my biggest dream and, and at some point that happened, you know, thankfully and at that point I was like, well, okay, now what I really need to do is I need to, you know, take what I just learned to kind of feed myself and take it to the next level. You know, I'm building a company and this company needs to be X big and this is like, I kinda want to pause here for a second, this is where it starts the moment I said, the company needs to be this big where I need to make this much or I need to, you know, whatever my, my usually arbitrary goal was, I started setting myself up for failure, not because goals aren't good goals are great, goals are super important, but because I never had any point where I said, if I get to that goal, then here's how I'm going to fundamentally modify how I think about goals, right? All I said to myself was cool, I finished this goal, I'm gonna swap it out with another goal and I'm gonna swap it out with another goal and I'm gonna swap it out with another goal and none of them will actually matter, never ends, you know, as I started to, to kind of grow in my career, you know, I built an agency and we grew to hundreds of millions of dollars and we sold it and then the first thing on my mind and I see this a lot with, with founders that exited was I have to do it again now to be clear, absolutely no one has ever said you have to do it again, right? You made that up, any, any comparison or delusion that we created to think that that was thrust upon us is bananas, it's insane, right? And yet we kind of all do it right? I certainly did it. And so I said, I have to build something else and you know, as you know, I went out and built eight more companies and that still wasn't enough. It really frustrated me because at some point, uh you know, I'm chasing validation at some point, I'm long beyond like trying to feed myself and so if all of this is self imposed, right? If I'm basically putting myself on that treadmill and telling myself I have to keep kind of hitting the arrow up faster button, what the hell am I doing?

Ryan Rutan: There's no endgame, there's none right? And it won't

Wil Schroter: stop, There is no one game, but why do we all keep doing it? Like over and over every, every person that I meet again, there are some people that have come out of the woodwork pop up on twitter that will be like, hey, you know, I've got it all figured out or I do things differently. I'm super zen in life, which is awesome. I envy you at so many levels. What frustrates me is why can't I'd be okay with where I'm at? You know, you know, why is that so broken?

Ryan Rutan: Where, where do you feel it the most? So if you, if you were to look back at, let's say let's say post blue diesel, right? So in those moments where you found yourself, you know, nearing that point where you know, the, the, the exit was complete, the turnout was done. Um you can see that freedom coming, you know, where was your focus? That was like, what, what were you feeling in those moments, was it? I've got to go find something to do. Was it like manic energy or was there already a list of things that you wanted to chase down? Like what, what was the core driver there? Can you go back in time and find it?

Wil Schroter: Yeah, I know it. Um, I got lucky. Uh you know, again, it was in and I, I hate the word, luck for entrepreneurs, entrepreneurs are fortunate, not lucky. Powerball winners are lucky. Um, I, I looked at it as this was a fluke, which again happens a lot. Um, and it's funny because there's no way to fluke that business. We were in an agency business, you're selling people for time. There's no like special version where people pay you, but you don't actually deliver the product right? You have to deliver. It's one of the most complicated businesses there are, but regardless, you know, I just felt like, hey, you know, I had good fortune. It's a one off. The only way I can feel good about this good fortune is to replicate it and validate the fact that this wasn't a fluke, which was a broken assumption, but the bigger broken assumption was that I couldn't have just been so happy with what had just happened and a lot of people don't understand this. A lot of people like, well, yeah, you know, you, you went and you bought nice stuff and you know, you were, you were rich and I was like, I get it and it was totally appreciative and I felt, you know, so fortunate. However, what, what, what threw me off was okay. So everything just went exactly the way I wanted it to. Why don't I feel more awesome? Uh, and, and, and I talked to lots of other founders did exponentially better than I've ever done. They feel exactly the same way. And this isn't just about, why can't I feel good if things go well? It's really more about why can't I feel okay right now, what's always so broken in the right now that I can't wrap my arms around it.

Ryan Rutan: It's the big question and I'm not sure we're going to find it, man. I don't know. The answer is the answer is not easy for sure.

Wil Schroter: I'm okay if we don't find it, but, but I'd really like to talk about what causes this. I'd like to talk about kind of, um, why we keep coming back, you know, back to start, back to start, no matter how many times, uh, you know, we do something in the reason. I think this is particularly important for, for founders is because we are on a very goal driven plant right over and over goals after goals, after goals. But I think that we get into this dangerous routine where it no longer becomes about what the goals accomplished. It just becomes about more goals. Example, if we were to say at the formative stages of startups dot com, Uh, if we ever get to $1 million, you know, we'll be able to pay ourselves, etc, we've made it And then we get to $1 million dollars and we say, cool, yeah, we're good. Don't need $2 million. That is almost heretical in startup space. This idea that, you know, how could you be okay with where you are if the next goal isn't bigger, But Ryan, how often do you hear people say that?

Ryan Rutan: Never. Never. But, you know, it's interesting is most of the heresy calls would come from people who had yet to hit those milestones. I think that's what's interesting about this is that a lot of the pressure and a lot of the questions, a lot of that, you know, people seeking for you to validate what's already truly been validated and I want to talk about that in a second comes from people who haven't accomplished it yet, right? It's there. They're looking at you and going, well man, if you made it to a million, like why the hell would you stop now, right? And they're sitting there trying to figure out to 10,000 or 100,000 and they're like, well you made it to a million. Why would you, why would you squander that talent? Why would you, you know, there's so much more potential right words that drive me nuts on a constant basis. But um, I thought it was interesting because it's, it's something that's been echoed in a number of conversations I've had, um, one just a couple of weeks ago with somebody who's close to selling a business and, and he said, you know, finally I'll be able to prove that this is a good business. And I was like, man, you've been running this thing for like eight years paying yourself really well. I know he's paying above market salaries in, in a market that already pays well. I'm like, how is this not already validated as a good business for you, right? It was interesting that you said, right, the reason after after Blue Diesel, the reason you jump right back in was that could have been a fluke, I've got to go validate the fact that I'm a good founder. I'm a good entrepreneur. Um, she was already validated, right? You built and sold an agency and yet we're like, no, I got to validate my

Wil Schroter: validation. It's, it's not uncommon. That's that, that's the problem. There's a type of insanity

Ryan Rutan: somewhere in there, right

Wil Schroter: there is. And, and so I'll give you more close to home example, you know, more current for, for you. And I, um, you know, we've been running startups dot com now for about eight years and uh, you know, you and I are really proud of of what we've done. We've created a profitable business that employs a lot of people. Our culture is exactly what we wanted to be. Uh, we help hundreds of thousands of startups. I mean it checks so many boxes, you know, for what you'd want to accompany.

Ryan Rutan: I've got a huge smile on my face right now.

Wil Schroter: Well, yeah, no, it's, it's great. And then again, and this is, but this is, you know, where the turn is, is, um, theoretically were there, we set out to do what we wanted to do and it's not to say that we do not want to do anything else. I mean, we'd be bored otherwise. But um, it's almost like there's a part of me that says if we don't make this twice as big, we failed something now, here's what kills me. I don't know what we failed, right? If it's not twice as big, I don't know, who cares. I don't know why it keeps me up at night and I don't know why I'm supposed to spend the next 5 to 10 years of my life chasing that goal. Yeah, but I'm going to get me, but we were

Ryan Rutan: thinking about it, but we will,

Wil Schroter: but we will. Uh, and, and I, I, I keep getting to this existential place, not just with our business, but you know, talking to other founders and what what blows my mind is no matter what size those companies are, no matter what they've accomplished, they all feel like they're one year or one milestone away from where they were actually trying to get, like I've, I've yet to meet any founders. They're like, no, I'm exactly where I wanted to be again. I know they exist. And some of you are probably listening to this right now. I'm not pretending they don't exist. I'm saying as a guy who talks to founders pretty much all day long and probably more so than most people do. Um, it is not a common narrative that I'm seeing that I'd be interested to see if it's what you're hearing.

Ryan Rutan: Yeah, I know the balances on the other side of the fence. For sure, right? You do run into the occasional zen founder. Um, I would say something though interesting as I'm going back through my history of conversations on this topic, most of them, I would have, I would say, we're entrepreneurs, not necessarily startup founders and, and I'm not trying to mince words here, but the folks I know who are like, yep, it's big enough, it's good enough, they're running more of a, you know, like a lifestyle business, a nice a tm for them. You know, maybe it's a, it's a accounting consultancy. Uh, you know, maybe I talked to a guy who's owns a bunch of food franchises a few weeks ago and he's super happy with where they're, where they're at. Um, it's that kind of business, right? It's, it's not the kind that, that even really has that potential for exponential reality, and I wonder if to some degree, it's that exponential potential that we know that, you know, if you're working in a scalable startup, um, that somehow it's, it's our duty to scale simply because it can, um, if that's part of what drives us, right, just because it could be bigger, um, therefore it better be bigger. It must be right. I have to do this simply because it can. Um, and I think that's a really dangerous trap to fall into, but I would say that when I'm, you know, when I, when I think about the guys that I know the ladies, I know who are on that side of the fence, we're like, nope, you know, the business is kind of where it needs to be the most recent conversation was a real estate broker and she was quite pleased with the size of the brokerage and the way things were going. Um She had found a good life work life balance um and she was happy with it, right? But there also is an exponential reality to that business. She's not trying to become remax, she's not trying to become Berkshire Hathaway, right? She's cool with where she's at and and it's a, it's a good business, she's making great money, right? So she's, she's also not, you know, like, well, you know, I'm cool with where it is. Um but you know, I gotta clip some coupons now, she's doing fine, right? She's she's in a good place, so she's, she's earned some breathing room. Um but again, that if I was talking to somebody with a scalable, you know, let's say a software company or one of the two of us, we probably wouldn't have the same answer, even at the same level of performance, because we would assume there could be more for more performance, so therefore we should go chase it.

Wil Schroter: I I gotta tell you like, and this is just a moment in time for, for me as a founder and a, you know, a human, uh I'm at a point where I'd like my biggest goal over the next few years to have more to do with actually kind of like harvesting and enjoying what we've done than being constantly worried about what we haven't done and that here's, here's the twist on that and I'm terrified of that feeling.

Ryan Rutan: I'm

Wil Schroter: absolutely terrified of the idea that I might just want to kind of stop and enjoy what we've done. Um because I feel like everything, the wall's gonna are going to close in on us, the entire world's gonna implode.

Ryan Rutan: Oh man, I've watched you try to take a vacation, you're, you can't, like, I've watched you try to do this, it doesn't happen. Oh well let's, what was your most recent vacation man? Let's talk about that for two seconds. I think this will give a lot of insight into exactly how well you can hold still. You took, you took part of a week off recently, What did you do during that week?

Wil Schroter: I worked 60 hours a week outside, burned about 4000 calories. I wouldn't go built an outdoor kitchen. Um yeah, I'm not a downtime guy, right? Like, like, like for me, downtime is taking my energy and doing something that's just different. Um, I can't sit on a beach. I get really anxious, you know, just, just staring at the sun. Um, I don't hate beaches, but in general, I hate being bored, but, but this isn't Boy Ryan, this isn't about so much being bored, this is about chasing um false idols, right? Like chasing that next goal, that I already know, it's not going to get me anywhere, like, like my life isn't gonna change whatsoever on this next goal, but by, but in knowing that, right, almost like uh, you're on a game show and you're looking at, you know, the three doors that you can choose from and you know, all of them are the wrong door, but you can't wait to choose one. It's like, I already know, you already know what's behind the curtain. Um, but but what, what, what, what challenges me is the part where I can't, I can't prevent myself from being comfortable getting off that hamster wheel, right? It's been so ingrained in me for so long that what I'm built to do is run through walls, um, that the idea of not doing it is just, again, heretical, right? I I can't, I can't fathom what that would mean. And this is the conundrum. I see lots of founders in, here's a great example, right? Every founder I know has got this idea that I'm going to go and um, you know, sell my company for a gazillion dollars and sit on a beach, whatever and then they go and do it time and time again and they hate it and we all run into the same thing, the kinds of people that were built to have those types of outcomes to build something from nothing and go through all of that aren't compatible with the kind of people that tend to like just sit on the beach all day. The two things kind of are diametrically opposed not for everyone, I'm generalizing, but for a lot of folks,

Ryan Rutan: Yeah, I think it's absolutely true. And I think that somebody asked me once whether I thought it was a chicken and egg type question whether I thought becoming a founder and and kind of getting into that lifestyle and you know, getting used to constantly having something to chase made people who then couldn't stop. Like was it was it becoming a founder that led to that behavior or was it some ingrained behavior? Some, you know the personality that human um and their background that led them to be a founder, right? Was it? You know, which which one was it? I'm not inclined to believe that it's, it's either or I think there are probably some people who are on either side of that equation, but it is a very common trait of whether that's learned through founder ship or you become a founder because you simply can't hold still. I don't know. Um but boy, it sure seems to be part of it. I want to back up for a second though because as I was talking about um you know this, this need to need to keep moving. This need to chase and you said, Yeah, yeah. But you know, it's, it's really, it's about the false idols. Um I don't disagree with that at all. But I also can't easily decouple the two because I think that's the one because I think that the idols come from somewhere, right? The idols weren't as we said before, their self imposed, right? So we created that. So where did that need come from? And I would argue to at least an extent that a lot of that is that inability to hold still. So you know, we're like the looney tunes cartoon where you got the, you know, bugs bunny sitting behind the dog with the hot dog, you know, on a string on the stick so that

Wil Schroter: the dog runs forward,

Ryan Rutan: but we're the ones holding the damn stick, right? So I can't completely separate those two things in my mind though, because you know, if this was some third party thing that was being foisted upon us and said, hey, you're a great founder. We now expect you to go be a great founder some more, then I'd be like, okay, yeah, that makes sense that these false idols are being put in front of us, but we've crafted those things by hand ourselves.

Wil Schroter: Well, okay, so, so think about it like this, right? Uh imagine we're balancing complacency with sanity, right? It reminds me of this, this kind of yeah. Right. Right, right. And so like it reminds me of this concept where you've got two ends of the spectrum, One end of the spectrum is fear and the other one is greed, my whole life has been based 99% on fear in 1% on greed now, I wish that were the case right? And and and I don't mean greed in a bad way. Um I mean greed as in a passion to go do something and an altruistic version of greed right? Um the Gordon Gekko version of crude um but but that's not the way it's gone um and so what happens is when when my desire by greed to want to go get to the next milestone or achieve something or you know have some sort of like you know financial incentive etcetera when that gets extinguished which by the way doesn't take much uh it's the fear it reminds me of there's this really terrible Stephen King movie like in the eighties or nineties called the Langoliers I think it was made for tv movie Langoliers with with these these creatures that ate up time and so you're constantly chasing forward in times that the langoliers wouldn't come from behind and beat you.

Ryan Rutan: Those creatures are actually called Children in real life, they eat up time like you can't imagine

Wil Schroter: but like that was always like this this this concept in my mind that these things were like constant like that you know that that that my fear of the past, my fear of like what would happen if I don't keep running forward would come and kind of like take me over and in the early days I think it was a really healthy fear you know to the extent fear can be healthy. It was a great motivator, you know, I, I didn't want to go back to being poor so I was willing to do whatever it took, you know, however many hours I need to put in whatever it took in order to move forward. It wasn't agreed thing, It was a total fear thing. And then at some point, you know, I was okay, I had food in the refrigerator, had a roof over my head and I thought, okay, well now I'm going to be greedy and again greedy in a good way, greedy and like, hey, you know, let me go thirst for life and, and, and go after things. But you know what, uh, it never really manifested, you know, that, that the agreed never really became a thing. Uh it continued to be fear. And so when I'm balancing complacency with sanity, really, what I'm saying is I'm at a point where I know the sanity part that I can probably just be okay, but I'm terrified by this complacency idea, these langoliers coming after me, right? That, that if I'm complacent, the whole world is gonna like take over and eat me alive. That, that, that I'll be worth less worthless or validated less or, or any of these really kind of made up things. Um, and I think that psychology is fascinating because it makes it really hard for us just to stop, you know, just to take a moment and be like, dude, I'm okay,

Ryan Rutan: yeah, the fear pieces, it's such a tough one to wrangle because there's, there's such a flaw in, in a piece of the logic there and we're all guilty of it. And that's that there's a few things, right? So one is like the champion mentality, right? So I've achieved that. I did the thing I wanted to do, you know, whether it was just to build the company and develop stable revenue or you know, build it and sell it whatever it was, we've achieved that thing. Um, and then we get this champion's mentality that somehow now that was now I'm the champ, but now I have to defend that, right? And that's kind of what you were talking about before, after after Blue Diesel. Right? So the idea that my reputation isn't concrete in that sense, right? I've, I've achieved something now, but I could undo that or that could be undone. The irony here is that the very thing that we go and do next is the thing that's most likely to destabilize

Wil Schroter: this. We're just to go and start

Ryan Rutan: something else, right? Like, hey, I want to make sure I don't lose any of this golden amassed, let me go do the most risky thing I can think of, right? Like so, and yet this is the behavior that most founders engage in. Um, so there is, there is something deeply and I'll say it beautifully flawed about all of us, I think. But man,

Wil Schroter: alright, so let me say this, my concern is that I don't see enough of the founder narrative, you know, the founder narrative to me, like the the, you know, the the version that I see is when where two of us are sitting in a room where you're at a cocktail party and someone says, hey, you know, I'm actually good with where I'm at, you know, like I don't really care if we grow the business this year. I don't I don't really care if we had more people, I just I just want to be happy and I gotta tell you, I've, you know, been in this a long time, I've never seen someone say that. I mean, I would I would I would give them a giant, maybe not a covid hug, I don't know what you do, like fist bump, I don't know what it is, but I would give us some, you know, current embrace if someone would just break down and say that um in some sort of founder setting,

Ryan Rutan: I think in this case you're allowed to hug, I think I think you're allowed to break the rules at that point, social distances and the thing, if somebody

Wil Schroter: actually transcends to that level of foundered, um they get a hug. Okay, so, but but this is this is, you know, you know, where I'd like to just spend a little bit time if we would about um how a big challenge that we face as founders is being okay with where we're at, is setting a goal and say, Hey, I'm here, like my goal right now is to stay here is in heaven forbid, enjoy it actually. Yeah, yeah, yeah. You know, it's, it's, it's tom brady winning a super bowl going in there. Hey, tom what do you do next? Dude? Just won a super bowl. Like I'm gonna actually enjoy being the guy that won a super bowl, right? And like that's what I'm gonna do next. And I don't see enough of it. I'm not saying it doesn't exist again, billions of people. I mean they all have their own path, but I'd like to see more of it. I'd like to see more of it myself. You know, I'd like to see more of it with other founders. Um, and I think it would be a really healthy kind of zen movement amongst us to be able to say where I'm at is where I want to be right now, uh, and and not have to defend that. You know what I mean?

Ryan Rutan: Absolutely. I have the, to show how deep This goes. I have had a conversation probably about a month ago now where a friend of mine who runs a fairly large company, $20 million 10 or 15 years I was giving him some praise and he's telling me something, oh, that's really nice. This guy reached out at the end of this, my friend goes, you know, I just hate patronizing shit like that.

Wil Schroter: Wait, what? Like

Ryan Rutan: how deep does this go within us that even when somebody else comes and tells us like, you're doing a good job and you build a great business, Like he took this as this guy patronizing. I'm like, how dare you, how dare you tell me I've done a good job, you bastard! You're trying to slow me down, you're trying to hurt me. It was unreal.

Wil Schroter: But here's another side of it and it's something, you know, as I, I rewind back and look at different stages of my life um what I wish somebody maybe give me a little bit more guidance on and again, this is part of the reason we do this podcast. I hope somebody else picks this up. I kind of wish at different stages in my life. I kind of said, look right now, yes, I have some more goals in mind, but right now I'm gonna basically harvest the value of the goals that I just accomplished right, for example, you're 27 years old and you say, you know what, by all means, like I'm setting some stuff up for what I'm gonna do in my thirties, but right now I'm gonna really gonna enjoy being 27 write it just for six months a year. I mean the time period doesn't matter the point is he do it at all. Um I'm 45 like this is actually probably a pretty good time to just enjoy the fact that I've got a happy amazing family. Uh You know that that business is good, my friends are good health is good for a second. Um You know like and just enjoy it but I'm probably not going to if not now when you're

Ryan Rutan: probably not going to but yeah I mean like if not now

Wil Schroter: when right

Ryan Rutan: like what what conditions would possibly change to make it better easier, more acceptable whatever right? And I think that's there's there's there's a lot to be learned from the practice of mindfulness here which is just to be okay with the president of the whole point right? To be present, be in the present and to be okay with it. Um It does not seem to be a core skill of the the the current day founder. Um You know farmers figured this out a long time ago man, they plant the same thing every year, then they harvest the bounty, then they enjoy it, then they rinse and repeat right, they're not trying to make it bigger and better and different every year. Like they just like they know what they need to plant, they know what they need to harvest and then they reap the rewards and they do it again. Um We don't seem to have that.

Wil Schroter: There's one other aspect of this, I just want to dig into it for a second which is you know how the disposition of leadership roles down throughout the rest of the organization, right? And so uh you know I've seen with other organizations where with leadership is just like it's a kill yourself mentality, just like you know run, run, run, we have to hit these goals, whatever it gets pushed down to everybody, and now the entire organization is totally miserable, right? Everyone's miserable. And the idea is that there's some amorphous mythical outcome that will get too, by the way, they never get to it, you know, maybe the I. P. O. Maybe they do something like that, it rarely ever happens. Um and yet everybody gets pulled through the wringer altogether, right? Um My my point to this is as founders, we have to be exponentially mindful of our you know kind of mentality and approach and how that gets, you know, rolled into the organization and everybody else's approach. If I feel constantly uncomfortable, I'm going to make everybody else constantly uncomfortable and I'm gonna start to think of like really what the exponential effect that has of everybody that I'm working with, you know what I

Ryan Rutan: mean? For sure. Yeah, I mean even if you look at that from a slightly different angle and you say that even if it wasn't negative energy being passed down and dissatisfaction, it, maybe I'm trying to go back in time now and see if I've ever been susceptible to this, but it may be the case that because, you know, obviously as the founder, these decisions impact us differently, right? If we decide to slow down as a company, let's, let's take startups as an example. Um, you know, part of what we sell to people who want to come on board is this this vision that, you know, we are out there were chasing down our startup dreams and we're helping to build a better startup universe and we've got all these things we want to accomplish right now, you've got an entire team, let's say, let's say it's the opposite of being depressed or said they're hyper motivated, They want to go out and, and win battles and, and, and do great shit. And then all of a sudden the founders like, you know, maybe we just pump the brakes a little and be happy with where we're at, You know, this momentum built up behind you. It's like, it's like a train at this point. Yeah, yeah. So that now you feel again, because there are these times where we feel like we have to do this right? Because we told somebody we could once, right? And they don't remember that, but we said, yeah, we're gonna make this $100 million business. So therefore now we said it once and now we have to do it where we're frauds and charlatans or something else. Um, you know, you got a whole team motivated, you don't want to lose that momentum, You don't want to lose the motivation. And I think that momentum is one of those really, really dangerous concepts within the startup. We, in the beginning we have to work so hard to achieve it. Um, and then later in the business after we've achieved it and things are going well. Uh you know, I think we, you know, we become controlled by it to some degree and we feel pushed forward by that momentum. Um, and it's no longer a force that we're trying to create. It's, it's perhaps even when we're trying to resist, just so we can be okay with where we're at,

Wil Schroter: right, right. Uh in I guess that's, you know, the source of my frustration is that I think about how uh we're constantly pulled, particularly in startups. And it's not, isn't always in the rest of our lives, but certainly in startups were always pulled to this next destination. That is never now it's, it's wherever we're at now just doesn't matter. We're always pulled to this next destination because quote, that's what startups do, right? And startups are supposed to grow up into the right, that's the only way we work. And, and I think there's some value in some of those goals, I'm not trying to be anti growth. Um, but what I am saying is those goals need to be qualified and quantified. We can't just say up until the right is always better. Maybe up until the right isn't better, right? You know, or said differently, maybe that next goal we're trying to get to actually, we haven't played out whether or not we're better off for it. It's just bigger than what we have now, right? I I I think it's a dangerous mentality,

Ryan Rutan: 100% right. You know, we've talked about this in another podcast, we talked about growth for the sake of growth and how dangerous that mindset can be. Um and it's it's a piece of the same puzzle. We're talking about a reflection once of my own where I realized, you know, I didn't understand why necessarily, but I, I absolutely came to the realization that for me, the pursuit of something is when I'm happy,

Wil Schroter: the completion of

Ryan Rutan: it, I become satisfied. Like there's satisfaction in the completion, but there wasn't happiness in the completion and for me, I'm putting happiness higher on the pillar than than than satisfaction. Right? So, you know, and I think that's a big part of what motivates me back into to do the next thing and try to make it bigger, try to make it better because it's the pursuit where I'm I'm happiest, ironically, it's also where you're the least happy, right? It's that ebb flow, risen fall, um up and down of being a founder, but the happiest of the happy's were during the pursuit. Um, whereas

Wil Schroter: then agreed

Ryan Rutan: once it happens, it's just, it's done. I think there's also some sadness to that, right? Like I've achieved it now. It's over. Nobody likes that feeling.

Wil Schroter: I've always been a huge video gamer, right? Yeah. And my saddest moment in a video game is when I've realized I've already won, right? Regardless of whether I got to the end, like, like once I have the biggest gun or the biggest stats,

Ryan Rutan: your characters leveled up all the way your tech tree is done, You're like, now, what the hell do I do? Exactly,

Wil Schroter: Right, Right. And so, so it's, it's in the early stage when you're running around for one looking for one bullet and one gun or the knife. For some reason, every character at the beginning of the game always has the most useless weapon. But whatever. Um, you, you kind of get to a point where like, you're super excited to hit those, those milestones and that's awesome and I agree that, that, you know, when you get to that kind of Endgame, it's always kind of bittersweet, it's never what you thought it would be. You know, you start back up and do the next thing. The only difference is, you know, as you know, Ryan our lives aren't games and we have real costs, uh, to settling back up and doing it again. Um, often we're drawing energy from a lot of other places that are probably missing that energy from us that, you know, that that time that that that that energy that we can give, and I think if we're constantly trying to fill a bucket that doesn't need to be filled, um there's consequence there, and that actually genuinely concerns me.

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