Ryan Rutan: Welcome back to the episode of the Startup Therapy podcast. This is Ryan Routan from Startups.com, joined as always by my friend, the founder and CEO of Startups.com, Will Schroeder. Will, today's gonna be one of those episodes where I, I think we have more questions than answers. This is going to be the listener's chance to see inside our brains and watch the thought processes flow. The thing we want to talk about today is that in In startup land, we are taught that being content is sort of equal to being stuck, right? Contentment equals lack of progress. We're, we're not moving forward. But what if it's not, right? What if that's wrong? What if contentment is actually the goal as a startup founder?
Wil Schroter: It's been driving me insane, which is like the concept of being in uh content is driving me insane, and I think. A few days ago, I get a uh a DM from a friend of ours, a guy named Dan Martell, who's some of our audiences, uh, Dan messaged me in very much Dan form, and I love Dan, so this is this all positive, uh, and he says, Hey, Will, you coach, you know, you got a million people on your platform, but you don't have a business coach. Why is that? No, of course, Dan sells business coaching, right? So you can see where this one's go, yeah, loaded question, right, but I appreciate the tactic, right. And it got me thinking though. I'm like, do I need a coach? And then I thought about, OK, well, well, why don't I want a coach, right? Now, to be fair, Ryan, you and I both owned virtual, which was, we had hundreds of virtual assistants and neither of us ever had a virtual assistant, right? You know, so like, uh, you know, I'm not totally hypocritical here just to business coaches. Anyway, I started thinking about it. And I'm like, OK, if I had a coach, what would that coach do? Well, the first thing the coach does, by definition, is find shit you're not doing well, like, unpack all of your problems, right? Well, you could have been doing this better or this better or this better, and I'm like, honestly, I'm kind of good. I'm happy, right? Like all you could do is make me unhappy, right? Because like, there's no problem I'm trying to solve right now, OK? And then I thought to myself, shit. Why isn't there a problem I'm trying to solve?
Ryan Rutan: Right? What's wrong with me? That's the frame of the broader dilemma here, right? Is that as startup founders, we're constantly expected to chase solutions. It's why we exist, right? We had a problem with status quo and apparently that's supposed to be a permanent condition. I think that's what we're here to beat up, right? Does that actually need to be a permanent condition?
Wil Schroter: Ryan, you know I've talked about this, you know, over the past year, you know, I passed the ripe old age of 50, which is a very seminal age for everyone. Right, but you know, in my career, that's over 30 years doing this, right? So it's a fairly long time. It's a fairly long time to do anything, but more so, um, it was a good time of reflection, right? You know, so I was on vacation with my family and my wife and I were talking about, you know, kind of this this milestone of life. And I said to her, I said, you know, this could be the first year where I just stopped getting more, and I don't just mean material. I just mean like in, in life, right? And kind of enjoy what I have. And as I said it, two things happened. Number one, I was like that could actually make me a lot more happy. And then the devil on the other shoulder was like, you wimp like how dare you
Ryan Rutan: up at 50, huh? OK, yeah, yeah, the second half of our life in obscurity and yeah,
Wil Schroter: yeah, you might as well dig your own own grave, old man, right? But that's real. That's real. And I thought to myself, going back to, you know, to, to Dan's DM, how do I respond to Dan? Because really he he he was just really busting my balls, but like I thought it to myself like, well, he's not wrong, like it does help to have somebody coaching you along. That's literally what Ryan, you and I do for a living, we know there's benefit. But there was another part of me like, maybe that's not the problem I'm trying to solve right now. Maybe the problem I'm trying to solve is I just want to be content with what I got.
Ryan Rutan: Yeah, I think it it goes back to then like this crazy founder calculus that we're always doing, which is, is that the right problem to solve right now? Sure, that's a problem. I could go solve that. But at the expense of what other problems, and I don't seem to have any right now, but does that mean I should be looking for them? Should I go surface one? Should I hire a coach to find one, right? And I think that it's, you know, we, we did an episode a couple, couple months back where we talked about returning to the Y. and I think that's a really powerful piece of this entire discussion, which is that like, If you're achieving the biggest parts of that why, and you're living that out and and those things are happening, then you probably don't have to go looking for another problem. Doesn't mean you won't, doesn't mean you can't. But maybe at that point you look at that and you go like, look, we've built most of what we need and want to build. Will we keep adding stuff to it? Yes. Is that a problem? Not necessarily. It's just things to solve for, but little. Things iterations at this point. We know the help we provide is a meaningful impact to the startup ecosystem that we are changing founders' lives on a daily basis. That feels great. And here enters the discomfort. It's like, should this feel great? Like what, how greater could it feel?
Wil Schroter: That's what I'm just becomes,
Ryan Rutan: it's a muscle we've flexed for so long, flex that we have that is so inbuilt to. Thinking patterns, it's, it's the core of the model, right? The core of every single one of my mental models is what's the problem here? What's the shortcut gap to solution, right? Yep. Oh God, is it hard to turn that off?
Wil Schroter: It's funny. Last night, my daughter and I are having a conversation. We're having like deep conversation, you know, she's about turning 13, she's getting emotions for the first time. She doesn't know what to do with them because she, she's so like smart, intellectual. She like intellectualizes it. She's like. Dad, I woke up and I felt sad, but nothing sad is happening. What is that?
Ryan Rutan: Welcome to hormones. They'll ruin the next 30 to 40 years of your life.
Wil Schroter: And I remember I, I said to her at the beginning of the conversation, I was like, uh, sweetheart, I'm gonna tell you a bunch of things and give you advice and and give you whatever. And I was like, but before I do that, this is me kind of like hamstring myself. I know you may not be asking me to solve anything. But it's my natural condition. So if it sounds like I'm not listening and I'm trying to solve, stop me because I have a tendency to do that. And so we had a long conversation, like an hour at the end of it, she was like, Dad, you should do this for a living. I was like, sweetheart, I, I do do this for a living. Exactly what I do. I have a show called Startup Therapy, there's a reason, right? And uh it was an amazing conversation actually. Best conversations we've ever had. But what was interesting about that is to what you said, like, my natural instinct is to solve. Got solve, gotta fix, gotta change, right? And I don't have another gear. I don't have another tool in my dual
Ryan Rutan: bell. No, I think, I think we all start off with, with some degree of that. And then by virtue of being in the startup space, by being founders, by being repeat founders, it just becomes galvanized. It is the way of the startup world, right? We are chasing problems. We have to chase problems. It's how we achieve what we achieve, up to a point. And even when we don't have any, we, we, we continue to chase. But it does like at some point, man, it, it begs the question, like, is this just anxiety disguised as ambition? Is that what we're doing here, right? And, and to, to. outcome to what end and who will benefit from this endless anxiety disguise this ambition, right? And maybe people do, right? Maybe this is part of why we do get these outsized returns and we do because we are willing to sacrifice well beyond the point of return for ourselves in order to achieve outcomes for others. Makes it sound nice and noble. I don't know that it makes it any smarter or any more worth doing, but, but it's a nice spin.
Wil Schroter: Let's unpack where all this comes from. Sure,
Ryan Rutan: right,
Wil Schroter: we may not be able to solve how to fix it, you know, maybe we do, but let's at least unpack where the sources come from, cause it, it's not incidental, right? Like this stuff has some true root causes that that I think we can definitely uproot. The first is, in my mind that the startup world is the antithesis of content. I mean, just the whole industry we're gravitated in or you and I have been. Neck deep in for as long as we've been professionals, just breeds discontent. That's like your entry card, right?
Ryan Rutan: It is the nature of it, right? Contentment means accepting like whatever the status quo is, right? We're just, we're content with how it is. Literally a startup sets out to accomplish something that hasn't been accomplished before, at least not in the way we set out to do it. It is the opposite of being content. We're saying I'm not content. I'm gonna go do something about it.
Wil Schroter: Uh, I talked to my father-inlaw. Who's about to retire as a, as an attorney. I always tell him about like, uh, my work and what I do in my industry, etc. And over Christmas, he and I were talking and I was saying, you know, if you had my job as a lawyer, law would cease to exist every 5 years and 5 years from now, you'd have to become a doctor, and then medical would cease to exist, and then 5 years from that, you'd have to become a carpenter. And I was like, in every 5 years you'd have to reinvent what your career is or how you make money. And he was like, that sounds like the most awful thing I can think of, and I'll say that's funny because being a lawyer is the most awful thing I can think of. Yeah,
Ryan Rutan: I was just getting ready to say, yeah, by contrast,
Wil Schroter: I think he's a great guy, but anyway, but uh we we all thought it was funny, right? Like how how our worldviews, right? His is I got a law degree, so I, I could be content, so that I could be, you know, certain. About income, about job, about future, etc. right? And I was like I became a founder because the idea of knowing what I'd be doing in 30 years was the most terrifying thing to me ever, right? Like I was attracted to chaos. Chaos, I don't know that this industry of chaos in this industry or or intent of being content. are compatible, but our industry is is is not OK with it.
Ryan Rutan: No, no, it's not. I mean, like, quite literally, ambition is like the oxygen of of the startup space. The irony is that every time we do get a moment to breathe and catch a little more, we run faster, and so it's also the very thing that suffocates us. It's not like quite sure how we make this work.
Wil Schroter: It's so funny you should say that cause last night I got the, like the first full night's sleep that I've gotten forever. I have no idea why, right? But the first thing when I woke up and it wasn't 4 in the morning and I looked at my watch and I was like, wow, I just got a lot of sleep. My first thought was, I'm gonna do great at work today.
Ryan Rutan: Yeah, I am, I'm fully I've got a, I've got a 99% battery. How am I gonna how am I gonna wear myself to the bone today because I've got a full tank, yeah.
Wil Schroter: So much harder today, like that's, that's how I'm wired, right? I don't have another gear. I'm not like, oh, I'll just have a a more enjoyable day because I'm not like fighting through 5 hour energies to make it through the rest of the day. It doesn't even occur to me, right? But if, if we, if we zoom out of touch and we look at our world, OK, you know, the startup world, every Data point or or or every source that would congratulate, validate or reward us comes from some somewhere that says and don't stop, right? Like, so one obvious example is the investment community. Go out on your on your next fundraise and tell them I'd be content at $5 million in revenue and see how many checks you pick up. You will get exactly 0. We're rewarded for that ambition. Of course that industry comes with it. Every, um, major news article, right, is about someone who is wildly ambitious, not wildly content. In fact, it doesn't even matter if that person is absolutely depressed and miserable. If they have a story that celebrates their ambition, we're willing to overlook all of that. And the irony is usually they are depressed and miserable. Elon
Ryan Rutan: Musk working a 120 hour work week, sleeping on the factory floor, blah blah blah, right? Like, or the opposite, like we glorify this. I mean, like, we don't call it hustle idiots, we call it hustle culture, right? It's a culture, right? It's, it's right. There's a whole thing there, but then we do the opposite too, which is that we, we, we denigrate anybody who doesn't exhibit those characteristics like here's a great one, founders who sell their businesses for a life-changing amount of money. And then something else happens in the market or someone else looks in and goes, ah, they cashed out too early, they could have done, they could have done better. Uh-huh, maybe, right? Yeah, maybe we don't know that. But like there's all of these, there's all of this like perpetuated myth or or not even myth. I mean it because it does it manifests itself. The more we talk about this stuff, the more it becomes part of the narrative, it has become part of the reality of being a founder, definitely not a healthy part.
Wil Schroter: It's funny, uh, a friend of mine, uh, who's a founder, sold his business like exactly the right time in the market a few years ago, um, made a great amount of money, set himself up for life, um, he's at a stage in, you know, where retirement does make sense, etc. And every time I see him, I'm like, what are you gonna do next? What are you gonna do next, right? And he's like, bro, I'm good, right? Like I'm, I'm good. I'm not trying to give him a hard time. There are two reasons I'm doing that. The first reason I'm doing that is because I've seen a million founders exit. And they're all miserable, right? So I'm kind of like, you kind of need to suit back up or you're gonna go insane. Second reason is cause that's all I know. I'm like, what else would you do, right? What do you mean you're sitting at home reading? Are you kidding me?
Ryan Rutan: How many startup books are there, right?
Wil Schroter: And I think to myself, I'm like, what am I doing to this poor guy? Now, now it comes from like an honest place, like I, I, I only want the best for him, but I've been so conditioned by our industry that all that matters is what's next, that it kind of doesn't occur to me that maybe he's just good.
Ryan Rutan: Yeah, I mean, we're we're told to, to build bigger, run faster, do more, right? No one ever said. And also every once in a while stop to ask yourself why and do you need to, right? Never happened.
Wil Schroter: Reminds me of um uh like professional like football players. These guys are in a car accident every Sunday, right? Like it's, it's the yeah, it's the most brutal sport there is, right, as far as like absolute punishment to your, your body. Yeah, when it happens, when they're in that car accident, right? They have 100,000 people cheering them on live, right? They're, they're rewarded for that punishment.
Ryan Rutan: A lot of motivation to continue to take that punishment.
Wil Schroter: The quarterback for uh Miami Tua has had 6 concussions. His doctors have said to him, dude, do not walk back on that field ever, ever, right? What does he do? He gets back on the field. He's like, I mean, to be fair,
Ryan Rutan: maybe that's because he's concussed and can no longer make that decision. I don't know
Wil Schroter: this poor guy, but it reminds me of how you can be in an environment that rewards, rewards and celebrates your downfall. Yeah. Right? I mean, think of this poor guy and all I could think to myself was, dude, stop. Like there's, there's not a pass you're ever gonna throw that's worth never being able to speak again. And, and I think about that in terms of Ryan, the business that we're in, where we celebrate that, that, that pain, part of it is, oh my, you know, he worked so hard, etc. But there's another side of it is like, dude, at what cost? Was there ever an end?
Ryan Rutan: Yeah, and, and I think that's the 11 of the challenges is that we, we definitely do have this perception that upside is unlimited, right? And so there's always some ability to justify a little bit more, right? Like, to some degree, you can look at the football player and say, yeah, but does winning. Two Super Bowls, or 3 or just starting in your 100th game as opposed to quitting on your 99th, does that really change the outcome? How much more upside is there to that? It's not capped necessarily, well, it, it is to a degree, right? There, there is a, there is an amount that it's not gonna exceed. So I think part of the danger in our space is that there's this perception that the impact that we have, the money that we can make, the lives we change, all this stuff is nearly unlimited, and, and it's a huge allure and a draw, and Motivation to keep going. Let's, let's turn the corner on another aspect of this though, which is that's what pulls us forward, right? So we're being pushed a little bit by feedback. We're being pulled a little bit by the allure of what, what could be. And then there's the internal driver that we all seem to have, which is anxiety, right? The anxiety of contentness, right? So how does this push us forward, right? Where does this come from? How does it, how does it happen? Why do we listen? To it, why is it seemingly ever present regardless of how much we accomplish?
Wil Schroter: In my relentless pursuit last night of trying to give my daughter try to listen without giving her advice, um, of course, I gave her advice and one of the things that I said to her, I was like, look, uh, because she's dealing with anxiety essentially for the first time. She doesn't understand it because, yeah, she's very logical and she's like, logically no part of my life should include anxiety, right? And yet here I am. I I I I I feel scared about something and I don't know what I'm like, oh sweetheart, it's hormones, but, but. But I said a bigger lesson here is, don't try to make anxiety go away. Anxiety is a constant. You cannot make it go away, and the fool's errand for all of us, is trying to think that if just X, Y, and Z happen, anxiety will go away. Yeah. All you can do is manage anxiety, right? Like, think of it as a as a constant. In something that what what you can get better at or the tools that you get to um work with anxiety.
Ryan Rutan: I was talking to my wife last week, and, and she brought up this, this very topic around the fact that anxiety is present in a lot of situations in life, and she was taking it well outside the founder space. We were anxious about something else that we're considering in life, and, and she said, you know, look, anxiety is part of it. She's like, you're, you're not going to avoid it. You can't hide from it. I was like, have a conversation with it. Thank it for showing up and reminding you that there's probably something. Worth looking at here and then ask it to go on its way. And I was like, that's so smart. And it's, it's absolutely right. And it's a lot harder than she made it sound. I tried twice and it turned out that anxiety was the one that told me to take a hike at the end of the conversation, not the other way around. But it was
Wil Schroter: good
Ryan Rutan: advice.
Wil Schroter: I think about it in terms of, um, you know, my, my anxiety about being content. OK. Here's why I'm so anxious about being content. It's not hard to figure out, not hard to unpack. When I was young, I had nothing. Now a lot of people have nothing, but you know. My story, I was like, yeah, substantially poor. And for me, the anxiety of like not being sure if I'm gonna eat was pretty substantial, right? And so that matters, right? So I'm like, OK, anxiety created fear, that's really what it was in me to to go out and and do what wound up being pretty extraordinary things, things I would have never been able to do if it were just out of want. And so I say that to say for years and years and years and years, anxiety was my superpower. Right, it got me up in the morning and it was like we're gonna run through walls day after day after day.
Ryan Rutan: As a as a shadow character in that play. That didn't appear in your case, but it kind of was, it's apparent where it would have fit in. Contentment would have been the antihero, right? If you had just been content or or said like, look, I accept my circumstance. I accept the conditions. I am poor, I will stay poor, I will act poor. I will just do all the things I will stay exactly where I am. You had reinforcement from a really young age that this was the path, right? And the opposite was probably dangerous.
Wil Schroter: And so I grew terrified that if I ever stopped being ambitious and being anxious and being all these things that kind of propelled me forward, that I would be pulled back into this thing that I was afraid of. Now, I can tell you straight up that none of that is true. It's just like patently false. I know, just like my daughter knows that that like her, her anxieties aren't Coming from a logical place, I know that I will be able to feed my family and feed myself, right? I know that is true, but the anxiety that I've built says otherwise. My
Ryan Rutan: anxiety that you've created, right? And so now you're gonna live in it,
Wil Schroter: right? It's weird to me because Ryan, you and I are in such a unique position where as part of our jobs, we get to live the lives of thousands of other founders, these. Really dynamic people that are super ambitious, super, you know, excited, etc. in a gazillion different situations all around the world with all different cultures, with all different aspirations, and we get to sit side by side as as we kind of coach these folks and, you know, provide advice and see how all of those alternate endings in life could have gone. And and I've been very fortunate to be able to do that. What I've taken from that though, from from all of those journeys, is that I've yet to meet the founder that figured it all out. It wasn't like I was like, oh, and then I meet met this Yoda-like founder that was just so content and gave me the playbook for exactly how this works. It's like that is the biggest falsehood, is that someone's figured it out, and you can just replicate that, absolutely untrue, right? Every self-help book out there kind of essentially promises that and it just doesn't work like that.
Ryan Rutan: Well, they keep writing them. So clearly they haven't. The last one didn't solve it. Maybe it'll be the next
Wil Schroter: the reason there's always need is because nobody can solve it. In my mind, when I looked at, when I looked at being content, and again, as I was kind of reflecting over the past year, I thought to myself, I kind of rewound on all of the years and all those moments where I had like a level up moment. I'll give you an example. You you you've had yours. Well, where I was like, well, someday I'll have a nicer car, and I got a nicer car. Someday I'll have a house, and then I got a house, right? You know, some I'll have a wife and I had a way, right? Like, I look at it in terms of, did any of those milestones make me stop being anxious? Did any of those milestones make me truly content? No, they did not. Every one of those milestones just shifted. The focal point of my lack of content to
Ryan Rutan: something else, to something else. Yeah, that's exactly it. I mean, even like, look at founders that we all know, and, and have seen accomplished lots of things, right? Sam Altman, for example, Guy has clearly accomplished plenty in in in his lifetime already, and he routinely speaks publicly and openly about the crippling anxiety. It comes from wondering what's next, asking, am I doing enough to make that next the thing that it should be. It doesn't seem to matter what we achieve. It's this default state that we've created, right? It's this muscle that we've learned to like to flex that says. I need something to solve for, or I feel less relevant, and that relevance makes me feel anxious or scared or whatever, right? If I don't stay at the forefront of solving something, what happens to me, right? Right, and it's, it's a huge thing to deal with.
Wil Schroter: You know, something that's really funny about everything we talk about here is that none of it is new. Everything you're dealing with right now Has been done 1000 times before you, which means the answer already exists, you may just not know it, but that's OK. That's kind of what we're here to do. We talk about this stuff on the show, but we actually solve these problems all day long at groups.startups.com. So if any of this sounds familiar, stop guessing about what to do. Let us just give you the answers to the test and be done with it. I Watch this in two different artists narratives, right? A couple days ago I was watching a documentary on Avicii, right? You know the MDJ, uh, you know, he unfortunately committed suicide years ago, right? And they had a fair amount of film, uh, from him, like his meteoric rise because then he came out out of nowhere really fast and became really popular. What his friends were saying, his family and himself at some level was all this made it was hard. Harder and harder for me to be happy, right? Like, as I got more famous as the expectations got bigger, it made it harder and harder for me to fulfill those expectations and he became insanely depressed. Separately, there was another not documentary, but uh the Lego Movie of Pharrell, and he says something where like, I don't know, I don't know the audience would have picked this up, but he basically said, I was so successful that I got to a point where I could never be that successful again.
Ryan Rutan: Right, at least from a like from a rate of change perspective, right? Like, I'll never be this because I'm already so big, I can't get so much bigger that it's noticeable for the second. Well,
Wil Schroter: he had like 5 hit songs at the same time with like 5 different artists, like the guy was an absolute prodigy, but he was like, and that will never happen again. Like at some point he realized it wasn't just gonna keep happening. Yeah, and that creates an insane amount of depression. When you realize that you, you can't beat your last game, really successful anybody, particularly what I found as athletes, you know, when they come out of their profession, and they look back and realize they'll they're, they can't recreate that level of success.
Ryan Rutan: I think there is something really scary about some level of certainty around the fact that you've peaked.
Wil Schroter: Correct. The kind of people that get to that level aren't the kind of people that are content not doing it again.
Ryan Rutan: The irony being they've accomplished something more than basically, I'll never be able to do that again. They could also caveat with that with and and no one else is ever likely to either. There's somehow there's there's no comfort in that. I'm struggling now to recall where I saw the research because I'd like to, I'd like to, to, to credit it, but basically said that overachievers are more likely to experience. imposter syndrome, even after reaching their goals and despite achieving more than most other people would, right? So I don't mean overachiever in the sense that like you were the try hard. I mean, people who actually have overachieved, right? But the research showed that they were even more likely to experience impostor syndrome having arrived there. Partially, I think that comes from that place that you just described, well, which is that The self-help books don't work, right? There is no prescribed path for doing this. And even most of the founders that we talked to, if you ask them, so what were the exact steps you took to achieve this thing? They can't tell you. It's like, well, right, it kind of happened, that's sort of happened. We reacted this way, that happened. There's a lot of just like pachinko ball type outcomes here where we're just bouncing off the pins that life. And I think part of that, that, that inability to go back and say like, I could easily reconstruct this. I know how to do this again, or I could tell someone else how to do it, is part of what leads to that impostor syndrome. And I think that's part of what leads to the anxiety around needing to do more, so I can show that it wasn't a fluke. I'm not an impostor. I'm so good at this. I can do that amazing thing. No one deserves done twice,
Wil Schroter: right, right, right
Ryan Rutan: off the treadmill,
Wil Schroter: OK. You're also, you don't have to. And so hopefully some of them are listening to this and, and they'll nod when I'm saying this. Whenever I see my friends do something extraordinary like that, right? They've had an extraordinary outcome. I always sit down with them. I, I, I make a, um, a point to sit down with them. And say, now remember, you've now done what 0.0000001% of people can do. The probability that you'll do it again is zero, and more importantly, you don't have to, because you already did it, right? You, you, you cross the finish line, don't think that like that crossing the finish line has to be done twice in order to validate you. It's one of the, the biggest challenges that ultra successful founders have is or even it doesn't have to be ultra successful, successful founders is that they, they believe they have to. Prove to the world, and by the way, no one gives a shit. They have to prove to the world that it's not a fluke, and that they're so good that they can do it again. Every now and again someone does, which I would argue is even more of a fluke. I see no data that says you're a good entrepreneur or bad entrepreneur because you did it twice.
Ryan Rutan: I would completely agree with that. You know, it, it's funny. Like it, it begs another question, which is like, if you've worked this hard to get somewhere, in many cases our whole lives, like, to accomplish the things we've accomplished, why is it so hard to just stay there
Wil Schroter: then? Let's talk about, hey, I worked really hard in my life for a really long time to get the things that I have in life. Like, wasn't that the point? It's the whole point of getting here that I'm here, right? You know, my wife and I were talking about this at length, and I told her I said like, number one, I never expected to get to this point in life. And and and when I kind of quantify that quickly, I would say, I never expected to meet such an amazing woman being my wife. I never expected to have such cool kids. Like my kids are just good kids, right? I don't talk shit about them cause they're such brats, they're not. They're actually just great kids, right? I have a dream job where I get to work with people I care about like you, right? Which is Amazing. I absolutely don't want a different job. I, I, I have not even considered any other career path, like this is it, OK? I'm financially OK, I'm not the richest person in the world, but I'm OK. So I don't have, you know, those worries. And, and I get to do whatever the F I want to do all day long, right, which to me is the the greatest like outcome, right? That's the dream, right? So what am I missing? Dude, if I'm not content now, what the hell am I waiting for? And yet, I wake up every day being like, man, gotta get after it. Go after something for something. It's weird, it's weird. I, I, I, I gotta say,
Ryan Rutan: it's tough. I, I think that again, uh, so much of it goes back to the origin stories. I'm like, why we started these things and the required motivations, right? Like, again, it's kind of like asking a rocket to burn different fuel halfway through its journey, right? Like I got here on ambition or anxiety or one disguised as the other, right? I got here through dis. Contentment. And now you're asking me to pick a relatively arbitrary point and say, now I can be, I can be content. Now I feel like I've accomplished enough, right? Regardless of what the rest of the world is telling me, regardless of, of, of the, the internal driver that says this, regardless of what I think I could do. And so I think it just becomes really, really difficult to, to say and not have it change, right? Cause we've talked about this before too, like we set a goal. And then we get there and then it moves. So I I think the problem is that I, I don't know a single founder who's done this particularly well. I certainly haven't, which is to say like I'm gonna set one really specific life goal, and then once I achieve that. I'm gonna take a beat, like, I'm just that that will be it, and I can just stay there. I, part of it is like, I guess we don't really have a good enough crystal ball to know what that moment in time looks like. Yeah, but like, even just thinking about it from from just a pure startup standpoint or a pure company standpoint, if we, we contrast two companies, right? One. Think about like Patagonia versus Nike and how they've decided to grow. Like, you actually do see some of that, right? I'm not gonna say that Patagonia is content, but Patagonia didn't chase every single opportunity or new market, whereas Nike was like, we'll make shoes for Jordan one day, hey, what's he up to today, right? Like. Any anything that Adidas, I don't remember, but like they, they were a little bit more like we've figured out what we are and what we stand for, and we're OK to not necessarily grow like bananas because this is what matters more to us and kind of true to the mission, true to sustainability, all that stuff. And so, but we see it at the company level sometimes. Some of that may just be a plateau, right? We just sold everybody we can, so we're not gonna grow anymore. But the founders never seem to just be content with that.
Wil Schroter: Yeah, you know, and you asked me recently, you said, well, what's the difference between being content and complacent? Yeah, right? And and and I, I'm still not sure I know the answer if I'm being honest, um, and, and like, to me they sound synonymous, like in how I perceive them, but I know they're not. So here's what I'd love it to believe. I, I'd love to believe that for me being content means having infinite gratitude for everything that I have, and not wanting more because I don't have enough, not wanting more because I don't have enough, OK? That's what I think content means. Yeah, complacent means I've lost a spark. You know me well enough to know that like I'm a pretty busy dude, right? Like I do more in 24 hours than most people do
Ryan Rutan: don't believe that you sleep. But
Wil Schroter: right, right, right, it seems to be the the question. That that's not a flex, that's not a brag. What I'm saying is like, I'm just like mentally, I'm in a million places. However, here's the difference. I think I'd like to be in a million places and do a million things with zero consequence.
Ryan Rutan: That's the fear, right? The fear is that by not doing the thing, right? The fear is that the fear is that contentment is complacency masked, right? To me, being content is knowing when to say enough, right? Content is knowing when to say enough. Being complacent. Is there is something else that needs to be done, and I'm choosing not to do it. And I think that the, the, the wisdom that we all lack is the is the ability to tell those two things apart. Like, how do we know when enough is enough, because we can't see the future. We don't know what actually happens next. And so I think there's always, and maybe this is true, maybe there there's a truth to this, there is always a risk that what is contentment today can become tomorrow's complacency. That circumstances outside of our control change, the world moves, whatever happens, and what would have left us in a state of contentment has now left us at the risk of complacency by not taking some action. That's the constant, like, so maybe what we need is just like, hey, why don't we just check in on that yearly instead of every other minute like where it's this constant anxiety pattern, what else can I do? What else can I do? What else can I do? And instead just saying like, it's enough for today, it's enough for now, here's the next time it would make sense to re-evaluate them.
Wil Schroter: The book I read, uh, not too long ago was called The Psychology of Money, um, and the author essentially unpacks, we all know how to make money, we all know what the mechanics are, and yet our emotions change whether or not that actually happens, right? You know, if you just leave your money in the market long enough, it's gonna earn this rate of return, but when the market tanks or the market takes off, you get emotional and you change course, right? So you go through all these different um anecdotes. And and they talk about the psychology of being content, right? And and how that's actually a very um strong and powerful urge that kind of throws you off. And and he he gives a a like a famous quote and and it's killing me because I can't remember the name of the author, but it's an author in in uh in in New York City, and he's at some like hedge fund manager's mega mansion. And the author, I wanna say it's the author of Catch 22, and someone says, um, that they're they're looking at like all this that this guy had. So the the guy says to Joseph, he's like, hey, this guy's made more money than than you'll ever make, you know, even though you've had this, you know, wildly bestselling book, and he's like, that's fine. He's like, I've got the one thing this guy doesn't have. He's like, what's that? He goes, enough. That always struck me as being so incredibly true, like it it it it wasn't just like, oh, you know, also I feel shitty about myself. It's like he's right. Like he's so right. I've always thought, especially at this point in my career, like, I wanna be OK having enough, and, and here's why I say that, and I hope that the folks that are maybe earlier in their careers tune into this. There's nothing wrong with with getting more stuff, and this isn't about being material. What stuff is to you could be relationships, whatever stuff you don't have, right? The the fallacy is believing that once you get that, you're good. Yeah, right? And when you don't have it, of course you believe it. One of the things I think it's really funny, when I see couples arguing, and they talk, they're arguing over money or they're arguing over this or that, right? I always think to myself, even if you had that, even if you had whatever thing you think is missing, that is causing these arguments, you genuinely believe that the arguments will go away. different argument, just different argument, right? The difference is, and this isn't just for couples arguing, it's easy for us to blame. Not having stuff for our problems because we don't have it. It's easy to say. But what happens is when you get that thing, what you think at the time is, well, I don't have it, I get it, problem goes away. I never have problems again, right? And that is such a beautiful, beautiful fantasy. It's just not true, right? Because like anything in life, once you get something, and chances are you already have the things that millions of other people don't. So if you're like, well, you know, if I, if I had a Porsche, you know, my, uh, whatever would be better, like, dude, 99% of the world doesn't have a Porsche, right? But and and and they're getting by somehow or said. Differently, you know, you're sitting there saying if I had a Porsche, but another person somewhere else is like, if I had lunch,
Ryan Rutan: I had lunch, but there's also somebody with a Porsche who's saying if I had the Ferrari, 100%.
Wil Schroter: That's my point. It kind of never ends. And I think that's the part that when people say, hey, I don't have, the part that they're missing is, and when I get it, I'll be good. I'll be content. I got to a point in my life recently, I would say, where I'm like, dude, it just doesn't matter anymore. There's just nothing that I'm going to be able to backfill, that's gonna make anxiety go away. There's nothing that I'm gonna back it's just like I got nothing, nowhere else support, not because like I said, I'm I'm infinitely wealthy. It's because I'm smart enough to know that I've been to this movie so many damn times, right? And it just doesn't change anything.
Ryan Rutan: I think if I could par it back to you, you, you're kind of saying that like. Ambition and contentment aren't opposites, right? But, but the, the trick is knowing how much is enough. Right, and like building towards that, but I think that because there's so much wrapped up and as you said, like, things, stuff, possessions, it could be experiences, it could be health, it could be whatever, like there's so many things that get caught up into that, that it does become really, really hard. To draw that line around like, how do we say because to the extent that like we can look at people and sort of say like it's judgmental, we can say like they're not doing enough, right? You can sort of say like, this person isn't contributing enough to society, this person isn't doing enough within the organization, but like we never tell anybody to stop trying to achieve more. Like it's just not part of what we do again, going back to that like upside. Unlimited piece, that there is no narrative that says, hey, you not, not just you can slow down, you should slow down, you must slow down, right? Like if we start to penalize our tax over ambition, it'd be interesting to see how much more contentment we would create by putting some kind of a cap on it because right now there's no ceiling, right? And so by virtue of I can grow as big as I can, I, I should, right? I should just keep getting bigger and bigger. I'm, I'm trying to think of like what a content and ambitious startup looks like. And if I know any examples, I mean, honestly, like we could be close to that, right? Like, I think we are very ambitious in terms of the the outcomes we want to create uh for startup founders, but we're also at a point where you and I both look at our daily lives and we're like, this is awesome. Like we love what we get to do. We get to do things like this podcast. We get to do, we get to spend time with other founders and, and so, like, again, like, how do you create that balance? What does it look like? Another company that comes to mind, one of our, you know, some of our favorite founders who reference on the show are is is Basecamp. I would argue that they are a good example, at least from the outside, of what internal ambition, but, but also contentment still looks like. They they still clearly want to create some outcomes. They're not anti-money, they're not anti-growth necessarily, but they were very clear around. Kind of capping what that growth needed to look or feel like in order to maintain a certain type of culture and and a certain type of balance. And so I'm wondering what other examples we have of companies that are like both ambitious and content.
Wil Schroter: When I talked to them about that, you know, when I talked to David Hannameier Hansen, who's the co-founder, he and I were at lunch a while back. Actually it just occurred to me. That was when he moved to Malibu. I wonder if his house is there anymore. I,
Ryan Rutan: while we're reporting this
Wil Schroter: is during the LA house fires.
Ryan Rutan: I can guarantee that his house is there, all that air filtration that he's installed is working overtime.
Wil Schroter: You know what's so funny about that? So I talked to him a couple days ago, right? And like, uh, nobody knows or cares about this, but David is like insane about air quality. Yes, and you know, I'm in the process of building a new house and I'm putting in this new system, and so I messaged him I'm like, hey man, can you help me out like back out a system for uh air quality, right? How dumb is that, right? This is what I love about him. The most detailed response ever within like 5 minutes. I have no idea how this guy operates, but he's like a machine from another level. Anyway, when he and I were talking years back about accomplishing stuff, like he and I had very similar paths, single mom, you know, coming up from nowhere, blah blah blah, and we're comparing notes about how what it felt like to get your first thing like you, uh, the BMW, and he was crazy about cars. I mean, his like, right? And he's like, honestly, once I got a Porsche and he wasn't being a Jerk about it. I hear Porsche like, oh, you know what a richer. Honestly is the most humble response I've ever seen. He's like, once I got a Porsche, I would never be able to buy another car and have it matter. He wasn't saying his Porsche is so great. He was saying there's some threshold at which point there's really not much you can upgrade to.
Ryan Rutan: Yeah. He saw and felt that law of diminishing returns. He could, he could see it.
Wil Schroter: Yeah, and then so he said, he said, and so I've gone back, this is uh David's worth, I've gone back and I started to realize there's so many things I cannot upgrade, right? And I think that's kind of been my feeling at this point. You mentioned about our business, you know, sometimes I'll be in a founder group or talking to a founder and they're like, you know, how are you gonna make your business 10X uh bigger? And I'm like, only if it becomes 10X better because it being bigger could be the worst thing that could ever happen to it, yes, right? And I, and I said, look, what matters to me. Is that we're helping founders. The number that we help, I guess it's better if it's more, but not at the expense of us building a terrible company, right? Or a company we don't want to work at. There was a version of our company that had 5000 employees, right? And it was a global company and we're public company, whatever, and I hated my life. I don't, I can't see why I would be happier about that,
Ryan Rutan: or even if you just do something like increase the gross number of startups that we help, but also in Increase the number that we hurt along the way, right? For example, like there's, there's all kinds of things you can't, you can't just look at these things in absolute. There's so much nuance to this stuff, uh, it becomes really important in this calculation. Or
Wil Schroter: I hate my job and everybody here is just a faceless number in a cafeteria,
Ryan Rutan: right?
Wil Schroter: That sounds awful, right? I'd rather have 5 people at the company and actually care about everybody and interact. And so one of the things I think that's been really interesting and this is where I've kind of hit this level of contentment, but also So this concern about it is, for the first time in my life, Ryan, I honestly don't believe that acquiring more shit is gonna make a lick of difference in my life. Yeah, yeah, I agree. In other words, like, I don't look at it saying, hey, if I get a nicer car, which the irony being the last vehicle I just purchased was a bobcat skid steer. So if you get get an idea of of how much I care about cars, there
Ryan Rutan: are no nicer vehicles.
Wil Schroter: A 10,000 pound tractor, right? Anyway, but, but. Like the idea of like buying Ferraris and Lamborghini, like doesn't doesn't appeal to me whatsoever, right? There was a time when it did, yeah. Oh, I don't care about any of that, right? I don't care about having flashy shit, right? Like I'm, I'm building a nice house, right? But that's for me, that's something I want to create, that's something I wanna build, and has nothing to do with like how I think it'll affect other people, right? But I'm done, that's it. I, I literally have no other wants. There's nothing else on my wish list. That's
Ryan Rutan: an important place to be in, I think. Let me use this to illustrate where this often goes wrong. Here's where this goes wrong. And now you spend the next 23 days, 23 weeks, 23 months thinking, what else could I get that might make me happier? This is what we end up doing, right? We end up saying there is nothing right now that I need or want, and that becomes the problem, right? The fact that there's nothing to be ambitious about becomes the problem. Right, so look, I, I still don't think we've come to any conclusions or answers here, but, but for me, there's something that's becoming more clear, and it's that the contentment isn't a problem, right? It's, it's, it's a choice. The the startup world definitely like celebrates our endless ambition and growth at all costs, but it doesn't mean that we have to choose to do that, right? as founders. We need to ask ourselves like, what, what do we want, right? Like, well, what do you want? What do I want? And not just what is it that the world expects of us, just what is it that the game that we've been playing has dictated a rule set? Because at the end of the day, like, and you've said this before, like the only startup worth building is the one that brings you the kind of success that you can actually enjoy. Otherwise, what the hell are you doing? Overthinking your startup because you're going it alone, you don't have to, and honestly, you shouldn't because instead, you can learn directly from peers who've been in your shoes. Connect with bootstrapped founders and the advisors helping them win in the startups.com community. Check out the Startups.com community at www.startups.com to see if it's for you. Could be just the thing you need. I hope to see you inside.