Startup Therapy Podcast

Episode #148


Ryan Rutan: Welcome back another episode of the startup therapy podcast. This is Ryan Rutan joined as always by my friend and the founder and Ceo of startups dot com, Wil schroder will,

Wil Schroter: it's

Ryan Rutan: not exactly a secret. You've been pretty vocal about this in a lot of places that you haven't always had the most healthy relationship with your startups, uh past, present and maybe future, we'll find out. Uh you know, let's, let's go back in time, take a trip down memory lane. When did that relationship start? How did it start? And like when did it start to go south?

Wil Schroter: You know, it actually started like practically at birth, you know, but certainly in my childhood, I had a tough childhood, which is certainly a part of it, but a lot of it came from I had this huge insecurity that I didn't have security, right? That I need to do something to get beyond this station to create a world where I could be self sustaining and do my own thing. I would not have to be reliant on other people who, you know, historically, for me weren't reliable. Yeah, well that started things and that became the impetus for what would be a very unhealthy relationship with work. And it started this Sprint, the Sprint looks something like this. I have to keep running as fast as I can so that I can avoid this big shadow, you know, this, this, this gray cloud that's that that was over me. And if I keep running and if I run away from that fear about that insecurity, then I'm good. But if I stop, I stop for one moment and don't work harder. I don't keep pressing away from that fear, I'm screwed right, The whole world's gonna come crashing down. Uh this this awful thing is going to get me and all my insecurities are gonna, you know, come to the surface and my whole life is going to be rude. That's how I started my career. I don't think I'm the only

Ryan Rutan: one. Is that what they call hitting the ground running?

Wil Schroter: Yeah, I think some people go into their careers and I'd be curious to think about here, how you did it. Some people go into their careers with the idea of building more, getting more accomplishing more. I went into my career by just out of sheer terror. I just wanted to get away from this dark cloud and I was willing to run as hard as I needed to for as long as I needed to to keep that going. But the epilogue and we'll we'll talk through this is that the cloud never went away, no matter what I accomplished, no matter how far I ran it never went away. So my unhealthy relationship with work never went away. If you rewind same trip down memory line later, where does your start? And how does it develop? Alright, so before we get into this next topic, I just want to let you know what we talk about here is like 1% of the conversation, you know really, this conversation is going on all day long online at groups dot startups dot com where Ryan and I pretty much talk endlessly with founders about every one of these topics. So if by the end of this discussion, you like the topic and you want to dig into it a little bit more with Ryan and I just had two groups dot startups dot com and we'll pick it up from there.

Ryan Rutan: It's also pretty early. Mine was a bit different in that I felt like I was going to have to keep up with something, right? I wasn't running away from something I was running towards something that I was not sure in any way, shape or form, how I could live up to. You know, I had, my father was a larger than life character for me. And, and still in many ways is, um, and it was always this question of like, how will I ever do that, right? And, and there were some things that happened early on, that that kind of set that cadence. I saw how much my dad worked and, and as a, as a, as a surgeon, he was always on, right? I mean, the phone would ring all hours and this was back when it was just a phone in your house. So when it rang everybody heard it, so we knew right, the phone would ring all hours of the night and he was always on. So there was this sense that he had this, this kind of unhealthy relationship. I didn't see it that way. I just thought that's what you do, you're just always available, right? There's always gonna be something that can, you know, pop out of the darkness and you have to respond to it. And, and I turned that into kind of a superhero quality in my dad's case. And so there was always this sense that I would need to live up to that same kind of standard. Um the other thing and this was one that came up kind of later in career as I, as I had kids and I started to realize that there was something that was, that was that he executed that I was again not sure how I would do this for as much as the guy worked and he worked like crazy and like I said, he was always on, he always found time to be there for our events, things that we were doing, right. He would, he'd pop out for an hour and show up somewhere and, and we'd be there and then he'd go right back to working. Uh and so again, like there was this, this cadence that he had set around working all the time doing all this stuff, but also managing to be present and then I'm going like, wow, how the hell do I create that part, Like I got the like I can work really hard part, I can chase but then how do I find an environment where I can also shift gears and be where I need to be, or be where I want to be or be where somebody else wants me to be. Um and so for me it was always this sort of chasing this idealized state of work where you know, I was working hard and accomplishing the things I wanted to, but I was also present um and just setting standards for myself that one probably weren't even close to true, right? Like these were the the romanticized version of how all this worked in my brain. Um and and so that was a big driver for me, it was always sort of like how am I going to live up to these expectations? That by the way, you know to his credit were never foisted upon me always supportive, but never telling me to do it again. Somehow that made it even worse, it was like if he had just defined an expectation would have been far easier than me inventing them in my head. You and I talked about this all the time, but these 11 sided conversations that we have in our heads tend not to work in our favor. So for me, the unhealthy relationships started early by trying to build towards some glamorized, romanticized version of what work and accomplishments actually meant and making them way outside for what I was capable of at any given time.

Wil Schroter: So the opposite of opportunity, its consequence, yep, when you think about the consequence of not achieving or doing the things that that your father would have implied. What does that consequence look like to you?

Ryan Rutan: Well, that's what's funny is that I wasn't looking at it that way, right? I wasn't thinking about it. You know, I had the consequences were that that meant I had failed, right? But we talked about this a lot too. Let's define failure. Let's talk about what actually happens if you fail. Do I end up destitute and then starve to death in an alleyway? Probably not. Maybe, probably not, but that was sort of how it felt. And there wasn't any spectrum for me, it was sort of achieve this and be successful or don't achieve exactly that and be a failure right? There, There was no like there was no soft middle, it was either I win or I lose and it was binary for me and that was part of what set up the, you know, the really unhealthy conditions for how I treated work and how I measured what success looks like and all those things which I have a much better relationship with it now, I've gotten a little wiser as I've gotten older, maybe I've just gotten tired of running so hard. Uh but something happened where you know, there was at least a mental shift, not that I've got the perfect relationship with work at this point, but it's it's certainly better um in terms of how I think about it at this stage,

Wil Schroter: you know, it's interesting, you know, mentioned consequence for me, consequence went out the door a long time ago, a long time ago, right? I was early in my career, I made a little bit of cash and it wasn't that I made so much money that I'd never have to work again, or I was so rich that I, you know, I just would never think about money again. It wasn't that, but I had made enough where I could buy a house, a car, furniture, you know the stuff that that you try to go out and achieve, and I had some security in the bank, yep, but nothing changed and that's what kind of threw me. I thought for sure if I had achieved those milestones because it was so clear, here's the thing when you don't have that stuff getting, it seems like such an obvious fix because you don't have it. So it's so binary. But all of a sudden I was in the space where I had it and I didn't feel any better whatsoever, and I'll say this if I could choose between not having any of it feeling shitty and having it and feeling, I think the habit, but I'd rather be feeling

Ryan Rutan: shitty in the house, I own on the couch, I own having just returned in the car,

Wil Schroter: that's what I'm saying. I remember seeing uh, you know, yet another billionaire say money doesn't matter, it doesn't buy you anything. I was like, dude, that's because you have right handed over

Ryan Rutan: unencumbered yourself friend. And uh, and then tell me how you feel.

Wil Schroter: But what was interesting was uh, the guilt didn't go away. I thought for sure that because I had achieved this basic level of security, that the guilt would go away. And I can say I'm not going to run from that shadow anymore. And it turned out the shadow just morphed instead of it being about basic survival. It all of a sudden became well if you've achieved this, that's your baseline. Now, if you don't achieve at least this going forward and more, you're a total loser. You know, who told me that? Absolutely no one. No one ever said that to me. I've got this uh story of my daughter this past weekend. She did her first gymnastics competition and it was awesome. And before she went on to do her routines, I said to her, I said, when you see mom and dad in the stands, don't look at us and think I have to perform wonderfully for us because we don't care. And when I say that we hope you do great, but what we're looking for is whether you're smiling, whether you're happy, whether you're enjoying it because if you're not, doesn't matter. So she has a competition, she won some medals and as far as she was concerned, she was simone biles and she won the entire look, which

Ryan Rutan: was awesome. But

Wil Schroter: here's the interesting point. Next morning we get up and summer my daughter and I, we get up at like five in the morning, so we're sitting there, you know, enjoying our morning the next day and I asked her, I said, uh you've got these medals, how do you feel? You've got seven more competitions coming, How do you feel? And she said, it just means I need to do better and myself there it is, there it is. I didn't tell her that I didn't even imply it. I said the polar opposite and yet Here's this 10 year old sweet, innocent girl that's created this pressure. This is how it starts. That shouldn't or doesn't exist, but it's real, it keeps you up quite literally at night, keeps me up at night.

Ryan Rutan: It's interesting, right? So this happens in so many aspects of our lives, right? Where what, what once was the thing we strived for becomes our our baseline now and to some degree, you know, that's, I'm sure there's some biology to that there's certainly a lot of psychology to that and it's understandable to some degree right, particularly, You know, if you have a competitive streak, a competitive, you know bent to you, if I've already achieved that. Well now I want to achieve more, I've done that, I don't want to just keep doing the same, won't achieve more. So I, I get it. Uh, but there has to be limits to that. And I think that's part of where we start to go off the rails is that we, we just keep trying to achieve more and more and more. Um, and you know, the float keeps rising along with the tide and there's just the baseline, just keeps getting higher and higher and higher. Yeah, Nothing wrong with that. Until you get to that point where like physically, mentally, emotionally, you can't get to that next level. And then instead of being really happy with everything that you've achieved up until that point, all you recognize in that moment is that I failed to get to the next level. Not that I beat the previous 32, right? I just can't get the next one. Yeah. And and his founders, that's, it's such a painful thing to watch. And I think it was last episode, I referenced a, a founder that I had talked to who was really down on himself around the fact that they hadn't hit the big hit with the, within the VC, uh, type approach they were taking, right. They were looking at this massive scale, but what they had built was a profitable, stable business with happy, healthy employees except for him. Uh, and it was like, man, I can see this so clearly and yet he can't, because all he's thinking about was I reached for the next rung and I slipped not, I am really, really far from where I started. I have, I have come so far, I have climbed so high and yet all that matters is the delta between where I am and that next rung, which is a small percentage difference from where I am compared to where I started. Right? So it's, it's painful. Um, I want to circle back on something for a second if you don't mind the, because in the beginning you were talking about fear, right? You're, you're running away from this idea that you won't be secure, right? You're scared and you want to fix that. And I get that one. Then you introduced another concept and I want to see do they coincide or is this something that came later and that's around the the idea of of guilt. Right? So did the guilt come in after you had achieved what you needed? Um, and so you weren't scared anymore. But now you felt guilty if you weren't trying to achieve more. Was that the case or what? How do those two things play together

Wil Schroter: Right now? I think I mentioned, I've got two modes at this stage of my career and it hasn't changed, which again is the whole premise here either work all the time where I feel guilty. There's no in between there's no not working and feeling okay now I do take time off, I do. You know, do things that aren't work, I'm not working 100 hour weeks anymore, I'm just not, I also know it's not effective, I just can't uh but the problem is like, take today, for example, um if I were to say I'm gonna go take an hour to do you name it, let me go in the workshop and work on something to hell, even go to a doctor's appointment or something I have to do. I feel like I'm playing

Ryan Rutan: quality time.

Wil Schroter: Yeah, exactly, I feel like I I can only pay for it with guilt and I know hell we're doing a podcast on it. Dude, I know this is a stupid feeling. We were doing one of the founder group workshops last week and we're talking about just founder emotions and things like that, and someone had had written in the, in the chat, they said a little bit of guilt is a small price to pay for a better life, and I thought about that again, it makes total sense. I'm paying for a better life with a little bit of guilt, small price to pay and yet I can't do it, I'm so conditioned to be in this messed up kind of world and again, I'm well aware of it. Also worth noting, I'm at a point in my life At my now late 40s, as weird as that is for me to say, where I can't I can't let it go anymore, I can't kick the can anymore. Yeah, it's it's no longer okay, twenties thirties, 40 or early forties. I was like, I'll worry about that later right now. I'm like, huh? I'm about halfway through life. I better figure this sh it out

Ryan Rutan: now, because

Wil Schroter: I don't have like, I hope I live a long time. I hope you do too. But I don't have exponential amounts of time and more importantly, with the time that I do have. I don't want to live it like this. I don't want to be in default mode all the time. And I know no one else does either, but I found very, very, very few founders who've gotten past it. Hence why we're talking about. Was there still

Ryan Rutan: something about the argument? A little bit of guilt is a worthy trade for a better life. Did part of that still ring true for you? Or did that just sound like the want want want buzzer going off.

Wil Schroter: You know what? It feels like weakness? There's this Gordon Gekko version of me that just feels like lunch is for wimps, and the only way to succeed is by being this Spartan warrior that's willing to to fight through everything. And again, I'm telling you straight up and I don't just say this, It's a horrible mentality, it serves me in survival mode. It is my biggest enemy in the later stages of my career. Hence why we're talking about it again. And so I think at, at this point, Ryan, I can see exactly what's broken? I'm just having a really hard time fixing it.

Ryan Rutan: Sure, sure. And it's fine. We, this this is something that you and I well, outside this podcast, talk about frequently, which is how do we change things like this? Right? Once we're, once we're fully aware and, and we've talked it out, right? This isn't just something, this isn't a conversation that's just in your head anymore. You and I have talked about it. You and I have talked about this and and we've done all the things that seem like the things that you should do, right? Get it out of your head, talk to somebody else about it, get their feedback, get their

Wil Schroter: support, get their

Ryan Rutan: permission, get, you know, get their, you know, whatever it is that that you need, and we've done all of that, right? You came and said like, I have a hard time walking away for even an hour, um, without feeling like I'm letting you guys down or letting the company down, letting myself down. We're like, that's not the case, right? Like you guys appreciate that

Wil Schroter: everyone around me is saying like, go do something else,

Ryan Rutan: despite all the evidence, right? We still can't let go of these things. And I think

Wil Schroter: it's been hard coded for a long period of time.

Ryan Rutan: That's the thing. And so does that. It's interesting, right? So, and I don't have any answers for this, but does that mean it's just gonna take a long time for you to change the relationship? Or is this an ingrained pattern that you're just gonna have to somehow learn to live with and work around? Um what do you think at this point? Like, do you do you think that you're you're capable of changing this? And I mean capable in the sense of what are you up for this? Can you do this? You wimp

Wil Schroter: I do. And I'll put it this way, because I know at this point there's nothing else that I can do in life or achieve in life that's going to be more important than this. Making more money isn't gonna change anything. I've already tried that didn't work like, like the the problem is the same, it's in the same way people have all kinds of personal issues that they try to project onto something else. I'm not happy in my life. So it must be my job, right? I'm not happy in my life. So it must be my relationship. And so they start projecting this onto all these other things, thinking that once they fix that, well once I make enough money, these other things will figure themselves out, or once I find another partner, these things will figure themselves out what we failed to realize time and time again, is it won't you hear so few stories? And what people are saying essentially is this part of my life, job relationships, whatever is shitty and I want to get away from that, what they failed to recognize myself included, That moving to something else won't necessarily have a different outcome. Like if you hated your last job, you probably hate your next job. two

Ryan Rutan: people can't wrap their head around that. They can't, they can't Yeah, that's that's the thing, I mean, we we have this specific thing that's making us unhappy and yet we will then pin the fix of that on something completely unrelated rather than focus on the issue itself, right? And sadly it's it's a very, very common part of human nature. Um I get sad when I hear that statement. So like, I'm just, I'm going back, I can hear it echoing over and over in my mind. The a little bit of guilt is a worthwhile trade for this uh for, you know, a better lifestyle, a better life, right? Um one of the, one of the major problems I have with that is that there's there's no quantification of that, right? Like how much is a little guilt and over what period of time and to what, what detriment to your, your your overall well being. Um and then the other side of it is how much better does the lifestyle need to be before you'll say it's enough, right? To the point we were making earlier, the bar just keeps rising and so, you know, because of these fundamental flaws in the logic there, it's really hard to say that like yeah, a little bit of guilt is worth it. I don't know. Maybe not. I mean I would I'd rather you see, see you not be guilty at all rather than have to make that trade. But these are some sense still, I guess I'm kind of asking the same question again, I heard, you know, your emotional response to it, but practically do you feel like there's truth in that, do you feel like, Yeah, it's okay to suffer a little guilt to get what we want.

Wil Schroter: I think it's true, but I think that's actually not necessarily the whole problem and I'll give you a whole other side to this again. We talked about opportunity and consequences, opportunity or things we're hoping to get to and consequences or things we're hoping won't happen. Right. Let's talk about that so

Ryan Rutan: often ends up being the opposite as a founder, doesn't it? Right?

Wil Schroter: Right. Let's talk about the consequence or where that's driving and I'll give you I'll give you a great example for years and years and years. I thought that I needed to work myself to death, works like the office hero, right? The office hours hero where I had to be the first person in the office in the last person to leave, Why did I feel that way? Because I felt like if I didn't do that, the consequence would be everyone just screw off right and no one would work hard and everyone would abandon this thing and whatever and if they didn't see me working harder than everybody else, they would say, well dude, he's not working very hard so I don't have to work hard and I was like then the whole house of cards falls apart and so for the longest time uh I came into work first, I was like in at six a.m. And I would leave work last right 11 PM midnight sometimes and I'm not exaggerating when I say for probably 20 years I had never driven to or from work in daylight. It's just insane as that sounds that that was a yeah, that's why I'm so pale vampire. But what I'm really getting at is what was driving me like people would say, oh look at that ambition. He wanted to build something great. Not true. That's not why I was doing it. I was terrified. That's why I was doing it when that alarm went off at 5:30 AM. I wasn't like, oh I can't wait to start my day. I was like if I don't get in soon the whole thing is gonna come crumbling down. Was there ever an indication that that was true. Did anybody ever tell me that? Did it actually happen? No, that's the worst part about it, I made that up and I believed that if I didn't keep doing it, that the world would crumble now here's what's funny. It got tested. Ryan, it got tested because we don't have offices anymore. Yeah, I couldn't be office hours hero because I don't have a freaking office anymore.

Ryan Rutan: Would this be a bad time to tell you that like half the people on our payroll don't actually work for us anymore. Well and haven't for like 12 months with this. This is a long time to, to divulge that. We just didn't know when would be good bankrupt for two years and

Wil Schroter: no one's told

Ryan Rutan: you,

Wil Schroter: you know, by the way, I just want to mention if what we're talking about today sounds like the kind of discussion you wish you were having more often you actually can, you know, we're online all day everyday working through exactly these types of topics with founders, just like you. So any question you would have or maybe some problem you just want to work through. We're here and we love this stuff and we're easy to find, you know, head over to groups dot startups dot com and let's just start talking

Ryan Rutan: Yes, I agree with all of this. Um, you know, we, we do again, it's another one of these self imposed conditions that nobody is asking us to adhere to the other side is look, there is some sense that we do set the pace. So this isn't, this isn't like we can just do whatever we want. Like it's called leadership for a reason, right? We do have to set an example. Um, I think that where where I started to realize that there was a bit of a challenge here for me was when I was using myself as the only motivation, right? And I just assumed that there was this Not quite linear relationship between my output and everybody else's. So I was like, if I wanted the rest of the team to push 10% harder, I'd have to push 30% harder. You can imagine that that doesn't work for very long before I'm pushing 240% and I'm just dead. So, right, I I eventually realized like, this is like, you can't just do that, right? You cannot predicate the entire performance just based on, you know, over clocking yourself and and running that much faster. Uh and hoping that everybody else is going to keep up a bit and it's it's not healthy for you. It's not a healthy way to most everybody else motivate everybody else because at best they developed the same fear driven sense of responsibility or guilt driven sense of responsibility that you have and they start having the same toxic relationship with work. Worst case is they don't notice that you're doing that sh it at all and nothing happens except that you're the one who's working more, right? And and killing yourself. So it's it's such a dangerous, dangerous move. Um, but slowly, okay, let's let's talk about the current state. So now we we've gone remote office, we've seen that, you know, um you know, we don't have to be, you know, the the energizer bunny to keep everybody else working, you know, a normal and productive work week. Um How much did that actually change it for you? How much did that allow you to slow down and you start feeling less guilty by not working 60 70 hours a

Wil Schroter: week? No, that's the problem. You're seeing a theme here, consistent

Ryan Rutan: answer here.

Wil Schroter: What I learned. Um without intention was everyone was going to work as hard as they were going to work. I could maybe if I really really, really pressed my finger down, get folks who work 10% harder for a very short period of time. But then when I became afraid of, now it's about work. But what if people aren't working at all right? What if everybody's just hanging out on netflix? Uh and, you know, chiming in from time to time on their phone and then I thought about it, but you know what for all people know that's what I'm doing right now. So it occurred to me that I there's in this new world, if you will, there was no way for me to have that, you know, lead from the front charging first charge and hardest mentality because it just didn't really add up the way it used to. It was funny, but like,

Ryan Rutan: it doesn't, it's not visible. It's exactly the thing, right? There's, there's something about being the first person to the office and the last person out. It does, it demonstrates something right? Being the first slack message and the last slack message of the day does not have quite the same weight. Does it just not like, oh man, I did something today. I was in first and out last night. Nobody

Wil Schroter: because everybody is in first and outlast. I mean, so long as you're on slack, you're, you're in and out. I mean you can get a hot tub for all anybody knows. But my slack

Ryan Rutan: bot doesn't care where I'm

Wil Schroter: at, right. But, and so look, what I realized was, was how fruitless the effort was and how little changed when I abandoned the effort altogether. In fact, I don't, I didn't get a chance to tell you this a few months back. I was politely asked to stop posting. Hey guys, how you doing at four and five in the morning every day because it was just straight up annoying. Yeah,

Ryan Rutan: I've totally lost perspective on all of that because the things come through at random times. I'm sure I end up slacking people late because I'm anywhere between one and two hours. Uh, you know, behind the vast majority of the team you included. Well, um, and so you know, like a 4:00 message for me was, it hasn't been that weird. Yeah, it did. Yeah, there were some coming through it like two and three in the morning. Those felt a little strange, but I then I couldn't tell like he's still awake or is he? Yeah, Yeah,

Wil Schroter: Yeah. Um what I learned from again being the hours hero was maybe there was a time and place for it, you know, maybe was there some point in either the stage of our company or the stage of my career where it kind of sort of maybe mattered. But here's the problem I could never know because there's never a way to to have a control to find out whether it was true. Covid hits Everyone, bills out of the office were 100% remote and we're pretty remote to begin with. And I just was forced to test that, that concept. And it turns out no one gave a ship as to whether or not I was in the office, if anything, they were annoyed by it. And I guess as part of my psychosis and all this, I started to realize that I couldn't be constantly in the office or constantly at it and justified to myself that I was doing it because it was keeping everybody else motivated actually just just got taken completely off the table. And that was a big moment for me to realize that where I prided myself on having that level of commitment all of a sudden overnight, it was like, the world just said, doesn't matter. And I was like, yeah, oh sh it, it became,

Ryan Rutan: which is funny because I mean, not to say that it didn't matter. I think it matters less now. What we don't know is exactly, but maybe it doesn't matter at all now. We don't know exactly how much it mattered before, but suffice it to say, probably not nearly as much as you had hoped. You know, if you look at our glass door, one of our top featured benefits is actually, uh, will's in San Francisco three weeks out of the month. Um, what

Wil Schroter: it was like I moved

Ryan Rutan: Yeah. So, you know, it's, it's one of those things where like, I think it's an, it's an outmoded trope, right? I think that, you know, this idea that, you know, were these badges of honor that, you know, used to, used to mean something maybe, or at least we're a little bit easier to excuses maybe meaning something. They were just all pretty clear on now are, are not what, what we'd hoped and we dedicate an episode of this actually, probably more than one. Um, at least the one where we talked about, you know, the 40 hour work week and measure ability of output versus just, you know, time and saddle, um, which is related to what we're talking about, right? Like, you know, being the first one in the last one out, um, brings with it a whole hell of a lot of assumptions and, and we've talked about a lot of these in the past, but one of the main assumptions is that all of those hours are equal, right? And that we are absolutely having the same level of output. So if if I'm there 12 hours a day, it means I have 50% higher output than people who are there just there eight hours a day. The reality is probably not true. There may be somebody in that office who is just a superstar at what they're doing, who gets what you do in 12 hours done in four, right? So who's the real winner? Um So yeah, it reinforces that point that we we have to be really, really careful how we measure these things and and in particular like in this case, what type of nonsense that leads us to embark on like spending decades um in in the dark, right? In your case, right? Only being outside of the office um at twilight or dawn? Um not good for you right

Wil Schroter: now. You know, being forced to contend with it. It's the only way it went away. I didn't have a choice. It just went away on its own. The whole world stopped. And so I was forced to contend with it, which kind of makes me wonder, do I need to break up with work. And I think it's important to say, I'm not saying do I need to stop doing my job. I love my job. This is my dream job for both of us. That's the whole reason we built this and I think this is where it throws people a bit because it does links is where it gets really tricky, right? Normally we say I'm guilty or I'm this or I'm that and so I need to stop doing work, I need to sell my company where I need to move on to something else or quit my job, whatever it is, I need to make that change. This is one of those cases where I actually can't get a better job, reason we built it so that I could do exactly this all day. So I know the control in this experiment is that there's nothing else I want to do. So it ain't my job, it's me. But I also know I need to break up my relationship with work, kind of how I relate to work and like how I think about it how emotionally it makes me feel and probably as we're talking through this all of the different assumptions that I've come to believe are true, that probably aren't you know, that that I need to feel guilty. That's clearly not true. But I'll tell you this man, I genuinely feel like if I stop feeling that way I will become this homeless loser, that I will I'll lose everything and and I'll be a shell of myself and I genuinely feel that way. I gotta say it's

Ryan Rutan: it's it's funny because I mean, you look at that slightly differently and it's it's not the guilt that does it, it's the motivation, right? If you stay motivated, right? None of that happens, right? And so how do we start to separate and isolate those layers that say like, look, I'm driven by guilt? Well, the important part of that sentence was I'm driven right? Right? What you're driven by, right? And and can you change that relationship? Right? There's sort of a really, really big assumption there that says, I can only be motivated by guilt. That's it, that's the one thing that drives me, nothing else is gonna get me there. So if I don't have guilt, I have nothing. Um kind of hard to believe, right? And maybe maybe it's true. I don't know, I've certainly seen you motivated by other things. I don't think that it's purely guilt that motivates you, maybe it's just the strongest feeling, right? And maybe it's the one that's, you know, at the forefront and the one that you're most I'm gonna say comfortable with and I don't mean that and like that it feels good but accept that that is part of this equation, you know, it, right, the devil, you know? Ah and so it'd be it'd be really interesting to figure out like how we start to explore some of that and say like, well, okay, if not for guilt, like what else can I substitute, right? Is there a stevia to the sugar of guilt? Like how can I, how can I still get that same sweet flavor without all this bullshit that comes with it. Um And I don't have an answer.

Wil Schroter: What's yours like? You know mine is clearly guilty but what's your driver? What's the fuel that that keeps you going?

Ryan Rutan: I think it's still, for me it's still like and and again like I've tried to become more reasonable, realistic and objective about some of this stuff hasn't entirely worked. But for me it's still more about trying to live up to some of these these, I'm gonna I'm gonna air quote your standards that I wanted to live up to write these standards that I absolutely created out of thin air based on a five year old's view of the world. Um

Wil Schroter: Sounds smart, doesn't it? It's an example that you can think of.

Ryan Rutan: Yeah. So so things like the and so this is one that I'm actually quite quite proud of that we have achieved. We you and I together this whole this whole thing that we're doing um is my ability to be present for my kids, right? So you know there there are Standards that you want to hit in a lot of different levels. You might say like I want a certain salary, right? Well does that salary come with traveling 300 days a year and never being around? And so is that negotiable right? Can you will, will you accept that to get that other thing right? That's where that guilt comes in to pay for the lifestyle. I don't want to be guilty about what I'm doing with my kids to pay for the better life, right? Is that objectively a better life at the end of the day? Probably not for the kids. Um And so, so that's one of them. That was a really, really important one for me was to be in a position where you know, I am not playing hooky, but like if there's something important that I need or want to be there for, it's not like that just can't happen. There's no way that can happen now. Sometimes I do make those tradeoffs, We've talked about this sure, It doesn't mean that we always pick what we want to do or what's best for us, but we're not, we're not in that position. Um but the vast majority of the time I feel fully liberated to be able to make that decision and say I'll be where I want to be in that moment knowing that I'll make it up some other way, right? But in some cases, people haven't built their lives in a way to allow for that. They haven't, they haven't made those decisions. They haven't chosen to build a life that accommodates that. And so that was one for me. So that was one where you know I the standard that I wanted to live up to was that in any moment where I felt like I wanted to be there for my kids or even more importantly, I feel like they want me to be there for them then I wanna be able to do that. Great example this morning my my 10 year old has been having a little bit of anxiety around heading to school, which is really bizarre because out of the three kids, she loves school. The other two are in open revolt most days around school,

Wil Schroter: Hannah

Ryan Rutan: on the other hand, wants to be there and yet when we get there it's like I feel nauseous, I feel this like that or I forgot something. I should, we should probably go home and get it for anything right. So she's just having these little struggles and so today she came into my office and I don't know that she's ever asked, she'll ask me sometimes are you going to take us to school today? But she specifically asked this morning, can you take us to school today, can you take me to school today dad? And you know, I didn't even think about it. I knew I didn't have any calls. I knew there were some things I wanted to get done, but it's like 7 30 in the morning and I thought, yeah, absolutely, I can't, I didn't have to think twice about it. I would just say yes, that is one of the standards that I want to be able to live up to, that I have achieved right. There are a whole bunch of others that I haven't right. Like I loved riding around in my dad's Porsche as a kid. I've yet to buy a Porsche for my kids to ride around in. Damn it. Like I think they need one. I feel

Wil Schroter: like, I feel

Ryan Rutan: like they're leaning into that

Wil Schroter: and you need to be talked into. Yeah.

Ryan Rutan: So that, you know, there's all kinds of things. But you know, I think that as I started, the other, the other thing was a lot of those melted away over time and I just started to realize how much less important some of those things actually were, uh, than, than others. Right? So another big one. And again, this is one that was kind of set by my father, we traveled a lot. I mean at one point we didn't have a home, we were, we were, you know, very upwardly mobile, The homeless, we traveled in a motor home for a year and a half. It was such an incredible experience. Um, to go through. And it's one of those things where like, how am I going to recreate that for my Children? I, I don't know yet. I don't have. Um, I don't have. So that was one of the interesting things. My dad loved his job. He absolutely did. He loves it in a different way than I love what I do I think. Um and he had a different ability to kind of turn that relationship on and off. So he just sold his practice at one point, we traveled for a year and a half. I can't do exactly that right, just disappear. You're gonna be like, hey, I'm just gonna pause, I'll be back. Um I'll just open a new one, right? You can't just do that right? It's not the same thing. It's not as easy to recreate what he had. And so I've had to be sober and mindful that there are significant differences between how I have achieved some of the same things that he did. Um and again, like it makes me sound like I've just got this checklist and scorecard of things my dad did, that I have to accomplish and that is true to to a degree. Um but I've also been mindful that there are experiences that I didn't have as a kid that I want to create for my Children to um and experiences that he didn't have for himself that, that I want to create. And that was where I really started to think about what was that relationship between my father and work that led to some of the things that ended up being quite negative um later in life for him, his health, his weight, his, his his stress, all of these things um that eventually compounded into some very, very serious health issues that have had now permanent consequences. And so I have been very adamant now in the last you know, probably decade of my life and even more so like kind of you know, mid forties now heading into the late forties, soon being much more aware of like what the value of that relationship is, my my relationship with me and my wellness, my health, my well being and how that inter relates and and reacts with work. And so I think that was something where I can look at my father and say he didn't set a great example, right? He that is definitely something now great example and that he provided the anti case right? Like don't do this. Um but this isn't something I'm following him into and I'm trying to be far more cognizant about how I shape my life and my work relationship um such that I can maintain my health because you know, like you said, you can make plenty of money, you can you can have all the things that you have, but if you know, you're not in a position where you actually enjoy them physically mentally emotionally, what good is

Wil Schroter: it? I agree. I think if people are listening to this and and they're starting to relate to what we're saying, I'm hoping they come out with a couple outcomes. The first is I'm hoping they realize that this is a real thing. It's not just you're not the only one dealing with it. We are all dealing with this, we're all dealing with an unhealthy relationship and some of these relationships that are better than others, but it's pretty common. I I don't have yet to meet a founder has got this one figured out on top of that if you're early in your career and like a lot of these episodes, I hope you're starting to take notes on this to say I don't want to do that. So if I see my early indications of these behaviors, I need to change them, I need to go down a different path. On the other hand, if you're later in your career, I hope you're listening to this saying, you know what, I'm kind of in the same boat as, as these guys. If I don't change some stuff soon, there's no version where this gets better. I can't outwork it, I can't out accomplish it, I can't do anything unless I fix it right now. And even though you and I know where things are broken, I think it's kind of like losing weight. It's not like you don't know how to, it's not like you can't figure it out, but holy cow doing it is really hard and my hope is that as folks are listening, as folks are responding. You know, we talked to people, you know, all over on this, that they start to take this super seriously, that they talk to other founders take it super seriously and they start to say to themselves, I'm at a time, it's got to be fixed now because ultimately it's all that matters alright. So that was fun. But let's actually keep this conversation going. You've heard what we think about this, but you know, Ryan and I would really like to hear what you think and we're online like all day long, pretty much talking about every startup topic you could think of from fundraising, the customer acquisition to just really how to get all of this crazy startup stuff out of your head. And there's tons of other founders just like you, they're weighing in on these topics so you'll get a chance to just hang out and meet some really smart founders were also super, super easy to find. You head over to groups dot startups dot com and let Ryan and I hear what's on your mind, let's get to know each other a little bit and let's just start having more of these conversations

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