Ryan Rutan: Welcome back to another episode of the Startup Therapy podcast. This is Ryan Routan joined as always by my friend, the founder and CEO of Startups.com, Will Schroeder. Will, as founders, we are often chasing something, many things often, and innumerable and unquantifiable. Is it the case that as founders, both personally and professionally, That we just don't know when to say enough is enough.
Wil Schroter: Yeah, like, Ryan is so weird, like I've dealt with this personally, but I also, you know, talked to a lot of founders. We all get the concept of let's get more, right? Bigger company, bigger bank account, like everyone gets more. What you rarely hear is I have enough, or more specifically, this is when I'll have enough. This is when anything beyond that becomes a liability. And I think that's, yeah, I'm really excited about unpacking this today because I really want to talk about how our ambition, our quest for more. Turns into a liability that destroys us. And and while that ambition is initially good and it does wonderful transformative things for us, it also has a dark side, when we let it just continue to fester, that also takes us down, it becomes our our greatest strength and our greatest weakness. 100%, man. So Ryan, when you think about ambition becoming a liability, like what comes, like how do you manifest that in your head or or in your own life?
Ryan Rutan: At some
Wil Schroter: point,
Ryan Rutan: like it's, it's the law of diminishing return. And look, I think we got to go all the way back to the beginning on this like, so why does this start, right? We started in scarcity mode, every Startup starts in scarcity. I don't care if you're funded or not. There's something you're scarce on or you got money, you might just be scarce in understanding of how we're going to use that money, right? There's always some level of scarcity. We start in scarcity mode and we just never found the off switch. We continue to grow personally, professionally. And we're rewarded for that. People milestone our growth, whether we want them to or not in some cases, other people are looking and going, oh, you did this, congratulations, good job, right? Whether that's passing grades or, you know, getting promotions or building your company, hitting revenue, whatever it is, we're we're celebrated for that. So it sets this thing into motion. And we, we have this really early conditioning around this bootstrap scarcity, which starts to drive this endless accumulation mindset where it's just like more for more, more for more, more because well more must be better, right? Right? Yeah, and more start to come at that cost. So as you said, right, turns from leverage into liability at the point where what we end up needing to trade for those incremental gains far outweighs what they're worth.
Wil Schroter: Yeah, and it, it's interesting because like, do you remember like growing up, there's this concept of eat everything on your plate, right? I, I, I,
Ryan Rutan: I still haven't lost that concept, and I'll tell you, it has, it's, it is, it has turned into a liability at this point. My wife and I just laughed about this last night. The cost of dishes here in Madrid, it's not cheap, right? When you eat out, you pay for it, and it's delightful food. So you have this, this dual fold problem for me. One, we have access to amazing world class food. An amazing world class prices, and so I feel like we shouldn't leave a scrap of it on the table. And so I'm now carrying it around my waist.
Wil Schroter: Yeah, I say welcome to obesity. In that same concept applies. We have this idea early on because we're young, we're growing, we're hungry and food was scarce, that we should have all of it. We should consume all and the idea is a clean plate is rewarded because you. consumed as much as you can consume.
Ryan Rutan: The irony there, sorry, I just gotta go back like, so do you remember what one of the rewards for cleaning the plate was?
Wil Schroter: Dessert?
Ryan Rutan: Yes, you clean your place. So if you do more than you need to, we'll give you even more than you more than you need to more unhealthy, right? So yeah, so this is this is pretty deeply psychologically set for me, yeah.
Wil Schroter: So what's interesting about it is because we have the more is always better mentality, no one ever tells us when it's time to shift. Or that it's ever time to shift, right? In fact, you're almost like kind of punished or penalized, especially as a founder, for the idea that you wouldn't just inherently want more. Where I think that's interesting is when we get into this, like you were saying, we're broke, right? I personally, professionally, and startups broke by nature that's how we all start. And so all more is good at that point, more revenue, more people, more capital, more, you know, you name it, more is good in our personal lives, especially when we're very young, more is good, having a car is good, having house is good, having, you know, family or, you know, whatever it is, whatever your path is, and what we don't hear about along the way. Is someone saying, so when are you gonna stop? You're like, no, I'm eating as much as I can. Like I clean every plate, eat every dessert, and like, you know, actually that's gonna end pretty poorly for you. Do you understand why? And here's the crazy thing. No, no, people genuinely don't understand why having more could ever be a problem. Now, to be fair, it's because a lot of them. You know, never get to eat enough. If you're 45 years old and just making up an age, and you're like, dude, I'm so broke right now, more ain't my problem, OK? That I feel for you, right? So just to be clear, most of the world doesn't have a more problem,
Ryan Rutan: you know, though, like, yes and no, obviously if you're if you're underfed, if you're under sheltered, if you're under anything, yes, clearly. But I think that part of the challenge becomes when we have a need more mentality, right? Even in in like when we start to adopt that without any sense for what enough looks like, right? Cause I think that even if you don't yet have enough, if you're already developing that I will always need more mentality. You're on the crash course, right? You may not be, you may not be at a point where you're in danger of hitting that wall, but it approaches a lot faster than most of us think, man. I mean, like, we've talked about this other podcast where what you actually need in life, and what is actually like a a life changing outcome or a life changing amount of money or a life changing number of things, relatively low and relatively achievable, and yet what happens the minute we check all the boxes for those needs, we erase. Those check marks, draw bigger boxes and fill them with bigger checks, right? Like have car need bigger car, right? Right. Have a, have, have all the airline travel I could ever want, needed my own plane, right? Nobody needs their own plane. That's
Wil Schroter: silly. It reminds me of, uh, remember we, we, we talked some episodes past and I referenced that that Joseph Heller quote, uh, he's the author of Catch 22. He and Kur on got are at some like big billionaires' penthouse or something like that. Vonga says to him, Hey, Joe, uh, how do you feel like this guy's got more artwork on his walls than than your, um, your catch 22 novel ever made. He's like, Well, I have something he'll never have. And he goes, What's that? Enough.
Ryan Rutan: Yeah, right, beautiful, absolutely beautiful.
Wil Schroter: I love those quotes because I don't think any of that part of that story is true. It does not matter.
Ryan Rutan: Just delightful though a perfect quote whether it happened or not.
Wil Schroter: I, it doesn't change anything. But I think what's interesting about that. is when we're talking about, you know, do I have enough, OK? This isn't, do I have enough private jets and mansions. I'm not talking about that, right? I'm saying your, your point where you are satiated, where you feel I'm well fed enough, I cannot eat more off this plate and be good. is sooner than most people think and the fact that they feel like I won't get there until I'm, I'm vomiting my, my meal, right, is ridiculous. Here's what I mean by that. Early in life, you've got this concept of a utility, meaning like how much benefit is there to having more. And when I learned this in my uh econ 101 class at, uh, college, and when I learned the term utility, I remember this to this day. It said, Joe loves pizza, and he said the first slice of pizza that Joe eats has the most utility he'll ever get. It's the same slice of pizza, but his happiness, his, you know, enjoyment out of it is at its apex. The second slice of pizza becomes less, and the 3rd, 4th, 5th, and 6th or whatever becomes significantly less. He's still eating pizza. But the value he gets, the utility drops exponentially. Now, that always stuck with me like I in in a weird way, I'm always maximizing for utility. I think it's the nature of what we do as founders and startups, right? You know, like how do I spend every dollar you know? But let me, let me apply this concept of utility or this diminishing value of more to how we actually live it. I remember a few episodes ago, Ryan, you and I were talking about every founder that gets their 1st 3 series BMW, typically white, right? And we said, wherever you were before the 3 series BMW. Until you got that series BMW is probably the greatest delta of utility you'll ever experience in a car before and
Ryan Rutan: after that moment was amazing. Yeah,
Wil Schroter: correct, right, that that was a 0 to 100 moment, right? Now, once you had that utility wears off and the novelty wears off, and you say, well, how do I do more than this? Yeah, yeah, and you look at the next car and the next card again, I'm just sticking with cars as, you know, a metaphor here, you know, it could be whatever that next thing is in your life. And you work really hard and you get, it could be the 7 series BMW. I'm a car guy, so I'm moving up in tears here. It could be that Bentley, it could be the Bugatti, you know, wherever, wherever you go on the chain, right? And what you realize when you get that next car, it's better in some ways, but it's not 0 to 100 anymore. It's like 0 to 20, right? 0 to 10, sometimes 0 to 0, right? And the moment the novelty wears off, you're like, well, shit. I had to work so much harder, or even if, if we don't use hard work as the metric, I had to contribute value so much more, whether it's money, time, you know, whatever, so much more in order to get to that level, and it wasn't that much better. That blows me away. What do you think about that?
Ryan Rutan: 100%, man, like I can actually draw that direct comparison because in the last 8 years, I've owned a number of cars, but I've owned two very, very different cars. And I got very different level of enjoyment from both of them. One of them was an SL 550, which is a very expensive Mercedes. The other one was a 1998 Land Rover Discovery, which wasn't a cheap car when it was made, but it certainly was by the time I bought it. You know which one I had a lot more fun driving around in? My $4000 clunker of a Guatemalan, you know, off-road vehicle that I just like love the thing. I had so much fun with that car. And there was no stress behind it. There was no nothing like it didn't, it literally didn't matter if that thing had fallen in two pieces in the middle of the road, I would have pushed them off to the side for everyone else's safety and walked home and not thought about it again.
Wil Schroter: Well, you, you also maximize your time. I'll give you another example. When I go on vacations, and as you know, I hardly ever take vacations, I'm just not, uh, so when I go on vacation, we usually try to go to a really nice place and because we hardly ever do it. And when I get to the bar, I order the same drink every time, uh, vodka gimlet.
Ryan Rutan: I know I know exactly what it is, yeah, yeah,
Wil Schroter: yeah, you do. You know me well. And so it's the same pour of Titos anywhere in the world, right? You know, sometimes less, sometimes more, but it's the same drink. There's nothing special about it, right? I'm not like a bourbon guy or anything like that, right?
Ryan Rutan: Nor nor is it a complicated or complex drink. Like you don't even need anybody to not mess it up.
Wil Schroter: Yeah, nice together. Yeah, exactly right. Anyway, so I'll I'll, I'll go to one of these resorts and I'll go to the bar and they'll, they'll pour me my my drink, which would normally be like in, in, in what I'd say like market prices like an $8 drink, and $8 just being even like a slightly higher end price point. And they're like, sir, that's $37. And I'm like, and I'm so offended. I'm not, I'm not that a hole who like like makes a big stink about it. I just, uh, privately like just complain to myself, but I feel like a chump. Yeah, I feel like a chump because I don't feel like I'm getting value. Well,
Ryan Rutan: you get the most utility out of the first one. It's the second one that should really bother you, Will.
Wil Schroter: The problem is there's 5 left. You know, this idea that once I have enough of something, right? I don't necessarily realize that as I try to get more of it, it actually doesn't work. Again, it's got the diminishing value, right? But if if we apply this to um our startups, it's so powerful. And I hear so few founders talking about this. We're to say, hey, founder, at what point does your business not need to grow anymore? Like that's heresy, right? Like, like how dare you talk my business doesn't. At what point does the happiness of your team outweigh the revenue of your company? How come shut up, right? You're fired.
Ryan Rutan: Get a new team. Yeah,
Wil Schroter: exactly. But what we're really asking those questions is, have you thought about like, when enough is actually enough? Have you thought in your mind, hey, once I get to this threshold, the 3 series BMW just to get it as a metaphor, I'm good. Ryan, I don't think most people have even remotely considered that. And it blows my mind considering how hard we work for it. It is,
Ryan Rutan: you know, it there there's so much packed into that decision though now that I'm thinking about it. For example, one of the one of the the little devil's advocacies here, right? Yeah, I don't necessarily need anymore, but we haven't achieved all the impact that we want to in the world. You know, based on what the problem that you're solving for us, right? So there's all these other reasons, right? Or like, yeah, I'm paid pretty well now, but there's still a lot of people on my team that I'd I'd love to be able to pay more, or right, there's all of these other things they get baked into that decision. So for you, how do you start to separate some of that out? How do you filter those things and how do you kind of stack rank and order them and say like, look, I'm gonna to base the decision on Enough for me, or enough for my customers, or enough for my team, enough for my investors, enough for everybody. Like, how do you unwind that calculus cause it is not uncomplex.
Wil Schroter: Well, think about it. What do those things need to achieve? What's the end game, right? So, I always think as as far as size of company, having built companies of all different sizes, I've learned that as a company grows and gets bigger and bigger, I become less happy. Because a whole bunch of things start to happen that affect me personally that I do not like. You now get politics, politics, right? Uh, you, you get things like, uh, you know, I mentioned the first company, uh, that I started Blue Diesel, we merged with an agency and then very grew very quickly, and overnight we had like a $10 million a month payroll. That brought me no joy. Right, I mean, it's just like it was so stressful and it it was so unnerving because it's unfixable that I didn't like it, right? Uh, needless to say, we have nowhere near a $10 million a month payroll at startups.com, and I sleep so well with that information, right? Like I, I feel like if something goes wrong for us, we can all get in a room and fix it, right? So for me, enough is just enough people, just enough revenue, etc. so that whenever a problem comes up, we can fix it and the order or the configuration. Of the company Is as stress free as possible. Let me expand on this just while I'm thinking about it. Let's build products that stress us out less. Yeah, yeah, we just had this discussion last week. We just sunset a product that that made us tons of money for millions of dollars for years. We didn't like it. And so we're like, you know what, it, it stresses out, it stresses our team out, let's just not do it anymore. We will make less money in the short term, maybe in the long term, by making that decision, but we will be more happy. Enough is enough. I wouldn't say we, we have enough revenue, we still need a little bit more, but we're not that far off, right? And there is a point where the reason we didn't go out and raise like millions of dollars of VA is because we didn't need what that capital could provide, really powerful, you know what I mean?
Ryan Rutan: Yeah, it's nice to be able to make those decisions, right? And I think that that is a big part of it, and it again it goes back to that saying like, what is that little bit more going to cost us? Or in this case, what is that little bit less gonna cost us? Does it actually cost us enough to make it not worth making a decision that's productive for the team, productive for the people that work here, productive for for everybody, comes out with a good result. So, I think that is the right way of looking at it. There there was something else that occurred to me as you were, as you were going through that in terms of like, when, where and how we get to those decisions. And that in some cases, I think it's not just a matter of do we want more, but if we ask ourselves, can we achieve more, but by doing it in a different way. And I think so often we just assume that in order to to grow bigger, we just have to throw more of whatever it was that we've always done. Yeah the same problem. So we want to grow bigger, we have to add more headcount. We want, you know, more, more profit, we have to add more products, we want, right? And so I think that instead if we can start to look at that and say, by continuously adding the resources that we always have, they come with some liability of their own. Right, and so that's part of what this gets introduced. So if we can create more without adding the liability, so can you find ways of doing it? Once you get to enough, I think you really have to ask yourself a hard question. Is this possible without changing the linear relationship between Benefit and liability, because if it's not, then it just has to be recognized as not being worthwhile.
Wil Schroter: I'll give you an example of where I see this as a milestone and a lot of founders uh that listen to this podcast, you know, some of you, I'm I'm talking about you a few times a year, I'll get a friend of mine, a founder, uh, that'll call me up and say, just completed my exit. I mean, for all the obvious reasons, I can never get enough of those calls, OK? Um, if you're listening to this. Podcast and you have had an exit. And Ryan, do you remember like a couple months ago, a gentleman reached out and by the way, uh, sir, if you remember that we're talking about you and he said, hey, I've listened to podcast for a long time, built this business, doing 50 million ARR, etc. you know, having just, you know, it's, it's incredible, etc. and I'm like, I can never get enough of those emails, right? You know, just talking about those success stories and the outcome. In the past couple months, I've had a few different of my friends reach out to me and said, you know, Will, I I I've had an accident. I've come to some money. If you're one of them now or in the future, and you call me, please make sure I'm the first person you call, because you need to hear what I'm about to tell you. Cause everybody else is gonna high five you, I'm gonna warn you. Here's what I'm gonna tell you, it's the same thing I tell everybody, don't fuck it up. Here's what I say. You've already won, OK? You've won. Now all you can do is lose. You, you have to change your mentality.
Ryan Rutan: It's not time to double down, right? Exactly. It's not the answer.
Wil Schroter: Most founders like, if it's 10, it's 20, if it's 20, it's 200. I'm going all the way and I'm like, are you, that's the worst answer possible,
Ryan Rutan: right? You, you can go all the way. Unfortunately that that often ends up going all the way to 0 rather than all the
Wil Schroter: point. This is exactly the kind of the crux of this. What you stand to gain next is tiny at best, and what you stand to lose is everything. You can gain 1% and lose 99%. You have to understand. When enough is enough, and you're playing a defensive game versus an offensive game.
Ryan Rutan: That's it, man, right there. Hostin, the risk profile flips, right? Right. All of a sudden downside completely outweighs upside, and I think we just don't get that. We've been in I must win to achieve upside. The minute you do that, right, continuing to push. It's just the the risk profile is reversed. All of a sudden the, the, the cards have all been flipped, and I think we just don't recognize that, certainly not soon enough in most cases. You know,
Wil Schroter: 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. Well, best example I can think of, Lance Armstrong. Here's a guy who won fucking everything. Lance, you won everything, you won at life, dude, right? You beat life, you won, you were the best around da da da na na na na, right? And like he's got that, um, and, and he. I couldn't even say that without finishing anyway, but he won. He was like Johnny Tur of friends, right? Uh, like he, he was the guy. And remember he had live strong, he had, um, I mean, dude was printing money, right? He was just like, he was the goat. And then he gets caught doping, right? Because he has, he has to stay on top. He has to, to be the best. And, and I want to say this from two different ways. On the one hand, I get it. Like, the reason you were the best is because you, you, you wanna be the best, but The moment you jabbed yourself for the first time, that's the moment where you jumped the shark, right? That's the moment where enough should have been enough and what you're about to do will buy you nothing and cost you everything. It's Tom Brady in another season of freaking the NFL, right? Tom. We got like 7 Super Bowl rings, right? If you get an 8th, no one will even remember, right? Like, no one will know the difference. And the next guy that, that knocks you on your ass and you don't get back up from, right, you lose everything.
Ryan Rutan: At the point you're asking like, can you make these in thumb size? You've probably gone too far, right? Like you're good, man, you're good.
Wil Schroter: I think for many of us, you know, we don't have to be Tom Brady, Lance Armstrong to hit this threshold. For many of us, we hit this threshold in, in, you know, let me put this together, when we hit $200,000 a year of income. Right? In other words, at $200,000 and it, it works very differently in different parts of the world. I think in some parts of the world, when people hear me say that, they're like, oh, you snobby first world Americans. In other parts of America, the folks in San Francisco are like, how the hell could you live on $200,000 right? I'd have 14 roommates, right? So, I understand, I'm, I'm, I'm normalizing. But anyway, in America, in most parts of America, let's say, you can buy most of the things you need. Now, it doesn't go as far as it used to, right? But, but you can get probably 80% to 85% of your utility in life, house, car, family, etc. and I'm not saying you're printing money. I'm not. What I'm saying is that next 10% is geometrically harder to get to. Yes. And the cost of it, if you apply risk, if you apply, when I say what it costs you, a lot of people just think, you know, money and time, it's more than money and time, it's health, it's relationships. There's things worth way more than money and time, that tend to be what you really pay in the price to try to get to that next level.
Ryan Rutan: Go back to your pizza analog, right? You get the most utility out of the first slice. So let's compare this now let's say, OK, you still want another slice. Well, the price of that slice just doubled. You're gonna get less utility, we're gonna pay more and just double the price of each slice. At what point do you stop eating pizza? Probably after about the 3rd slice, if you're paying any attention, and yet the the numbers are nowhere near that clear in in the game of life and startups, right? Your professional and personal uh returns are generally not quite that easy to see, nor is the diminishing return, but it's there if you go looking for it, and I think that's the, that's the part where we start to fail is that we don't even, we don't even look, we don't even try to set. A metric that is the final metric. We always set a metric knowing that once we achieve or get close to that, we're gonna move that bar. That is just baked into what we do.
Wil Schroter: That's the hardest part. And so, so let me give you my own version of kind of constantly moving the bar. When we sold Blue Diesel way back in the days, 25 years ago, when we sold that company, now mind you. I was like 27 years old, right? So like, like, relatively speaking, I had a whole lot of life left to live. It wasn't like it's time to hang up the Spurs. But in my mind, whatever that was, the next one had to be 2 to 3 exit, and I hear this all the time, right? Hey, you just had a life-changing exit. Yeah, well, now I'm gonna double down and do it again because here, here's, here's what I always hear. I don't want people to think I'm a one-hit wonder. Who cares? Who cares if you're a one-hit wonder.
Ryan Rutan: If all the people out there with zero hits are gonna judge you as being a one-hit wonder. Like, who gives a shit, right?
Wil Schroter: Oh yeah, he got lucky one time. OK.
Ryan Rutan: Ask Rick Astley if he cares, right? He doesn't, doesn't care at all.
Wil Schroter: Every time you get Rickrolled, he gets paid. So, with that said, I'm saying like for founders, they get into this thing and they're like, OK, uh, gotta have more, enough is never enough. I, I've gotta keep pushing my ambition. For me, I looked at it like this. If I didn't keep pushing more constantly all the time, I would lose everything. My ambition is 100% mapped to sheer terror. Like people think it's it's about greed. No, mine's all fear. I Operate completely on fear. The greed or anything I get to have that that comes out of a at the cost of fear is just found money. Yes, it's all driven by. I'm
Ryan Rutan: just doing this for the fear, folks. The money is a fringe benefit.
Wil Schroter: Yeah, exactly, exactly, and it's like I'm just, I'm so worried and I well have been, I should say, that if I, if I don't constantly run myself into the ground. That I'm gonna, I'm gonna lose it and I'm gonna, you know, become not ambitious.
Ryan Rutan: The irony there is that that can absolutely be what ends up causing people to, to, right? It's as if we're in the 9th inning and and we're up and it's the like, where is the we're like, let's ask for some extra innings. Why? All you can do at this point is blow the lead. Like you don't want extra innings now, you. Just want to defend what you've got because you've done it, right? But I think this is where we run into problem so because defining that metric is gonna be very, very individualized, right? What's the thought process look like? Like how can we help people to get closer to being able to say, here's how I actually pick that, here's how I will actually know, other than it feels right when it feels right. How do we help define that?
Wil Schroter: I went through this catharsis last year when I turned 50, right? And it's just, it's kind of a seminal year. It's the first year where you're old, old, and, you know, some old guy listening to this is gonna be like, oh, you know, he's like 75, and he's like, oh, you're a young pup. I'm like, dude, no, I'm not, right? Like I'm like, yes, I'm younger than you are, and I hope that I live as long as you do. I genuinely do, but I'm not playing that game. Yeah, yeah, exactly, right, but it is a threshold moment. In life, where you start to ask yourself, I don't know how much longer I can or will work, right? If you have that luxury or if you have that ability, if you have any level of introspection at all, you look back on your life and you said you take inventory of all the things you did, all the things you've accomplished, all the misses, all the regrets, like everything, and you start to say, hey, I have enough data now where I can actually say, was this worth it? Yeah, right? Like I, I went out, I got the car or I bought the house, or I moved, you know, somewhere else, and, you know, I did those things that I thought would bring more happiness, and now I can do the calculus to to measure it, right? Analytics style, and say, where did the happiness come from? Yeah, you know, where's happiness? And what I learned, you know, in in that process was that there really wasn't anything I was gonna go out and like acquire that was gonna make me geometrically more happy. Right. In other words, like if, if I, if I went no further than where I am now, not from a lack of ambition, just for a point of utility, right? Like I can get a 5th slice of pizza. I just, it'll actually make me sick. And when people hear that, I want you to understand, it's not because I'm so fabulously wealthy that I just like, I, I don't know where to park my 5th yacht. It's cause I don't need a fucking yacht, right? Like I just like, I understand that's what a lot of people like dream of and want. It ain't on my list, and it would bring me no additional joy.
Ryan Rutan: Yeah, I think that's an important part of it too is, is not just to continue because like we've used the, we've used the car analog, use the house analog, like at some point when you're just chasing more of the same thing, I think it also becomes problematic. Like at some point, probably worth branching out a little bit and kind of like, yep, redefine what is more actually look like? Like I do I just need more of the same thing like my son Jack loves trains, trains, he loves high speed trains. He just loves the high speed train engines. I found him this little variety pack of these things. There were like 12 of them in there, and I thought, well, that'll satisfy him, and I was, I was dripping him out like one a week, 1 here, one there, 1 here, one there. When you get to the 12th, and he's just like, I would love some more of these things. I'm like, why do you need more trains? What could there possibly be from a variety standpoint, like how much more joy could you have by having 24 of these things as opposed to 12? And of course, he was, you know, 5 at the time, so I'm not expecting him to be able to intellectualize this. But how many trains are we all collecting as adults, right? Like, again, like when we talk about the size of the company or the the personal bank accounts or, you know, the number of cars in the garage, the size of the garage the cars are in, at what point are we asking ourselves like, particularly like cause I think you and I both know people like this, they've been chasing more of the same thing for a long time with almost like no variety. To me that's always really bizarre, like at some point, think about where else happiness might be derived from and maybe go get some more of that.
Wil Schroter: So stick with that. That was the discovery that I made. What I realized was that the place I the bucket I kept trying to fill, um, let's call it stuff, and let's call it Biggering with business, no longer added any more joy. It was my 5th slice of pizza, you know, or or wherever you tap out, right? And I started to say, huh. That's interesting because up until now that those buckets always felt so empty that that they needed all my time and attention, and now I can add more to it, but they're just gonna overflow. There's nothing else I'm really gonna do there that that's meaningful, right? Like I've started 9 companies. If I start a 10th, sort of who gives a shit? That doesn't mean I had no ambition that somebody they won't do it. I just know now that whereas before it was a massive part of my my goal, my path, my identity. Now it's just not. What I did was, and this was the most cathartic. I looked around and I said, I bet there's other buckets, you know, and some people are listed as going, oh, you think so, idiot, right? But you know, your family bucket, your health bucket, your relationship bucket, your spirituality bucket, you know, your fitness bucket your health, but, you name it, and you're like, how much time do I spend filling those and a friend of mine, a founder, told me this years ago, one of our listeners, so hopefully, uh they'll remember this, says to me. Well, imagine if you spent as much time and attention and purpose and passion on your relationships as you did with your business. Like you were that intense about making your relationships, and I was like, I think everybody would hate me, but
Ryan Rutan: I would have exited 3 of them, 4 would have failed and I'd still be running one.
Wil Schroter: Exactly, exactly. But, but it was, it was a good point. Hey, Will, you know, uh, there are these other buckets that you. Woefully underinvested, and what if the next level of happiness or or excitement or whatever that you're looking for, isn't in the bucket that you've been filling this whole time. That's the thing. So for me it was hobbies. I went out and I started to realize that there's some things that I enjoy, you know, carpentry is my thing, uh, building a house is my thing, that actually have nothing to do with building a startup, you know, there's some parallels, but but really nothing to do with it, but were buckets that were completely empty, that I finally got. That first piece of pizza feeling you're back to full
Ryan Rutan: utility. You're back to full utility, right? And I think that's where it's, it's this, you're gotta hedge your bets on more. Right? You gotta spread things around a little bit and and it's just so much benefit to it, right? I think you named off a bunch of them. For me it's been relationships, wellness, some craft and projects, a lot of sport and philanthropy have been the things that have kind of like all of a sudden I found like, wow, there's there's something really, really enjoyable here and I'm getting a lot of utility out of it, um, and they're bringing me joy in ways that that the other things that I was chasing hadn't for some time because I'd already filled those buckets.
Wil Schroter: Yeah, like another part of its novelty, like 100%. I said, when if I go and start a 10th startup, there's nothing novel about it. Yeah, something will will do maybe the team, etc. but I've been on the journey a million times. Also, you know, that's kind of what's cool about this business is I basically get to live all these other lives, vis all these other founders without having to do that. Yes. But my thought was like, man, what if I started investing in other journeys, other buckets, you know, so I learned to become a carpenter, I learned to become an architect, I learned to become a 3D modeler, I learned, you know, I learned all these other things. And I became, I just as much passion. Like Ryan, you remember when you and I first started and like everything we learned from how like a pro forma income statement works to how marketing works to like how HTML works, right? Like was so exciting because it was so new and novel 0 to 100 moment. I think part of what I lost on this path is I ran out of those moments because this bucket was full.
Ryan Rutan: The 5 millionth line of HTML code I wrote. It was not nearly as exciting, right? Not nearly as exciting. Did it like we can all recognize that we go, well, yeah, anytime you any anytime you do that much of something, it's gonna lose its but and yet we don't recognize that in some of the most important aspects of our lives. Some of where we spend most of our time, all of a sudden we're like, well, haven't rethought that in a while. Why?
Wil Schroter: Right. And and I don't want to believe people are all that one dimensional. I don't want to believe when I meet founder person. That she's sitting there going, well, all I can do is my startup. There's nothing else that would possibly bring me joy. And I'm like, maybe that actually, I mean, I, I can't speak for everybody. Maybe that's, maybe that's true, but it feels shortsighted. It feels like you really didn't try too hard to to to look at some of these other buckets. Again, maybe you did, maybe you did the full analysis, and this is all that matters to you and all the power to you.
Ryan Rutan: And if you're still getting utility and and something from it, then great. I think you just have to start to question it when it's like. This doesn't fill me in any way anymore. That's where it becomes problematic and part of that, especially in the founder space is this sense of responsibility to a mission, to a level of achievement that maybe nobody else is paying any attention to, but that we internally feel like we have to achieve, we have to get there, we have to do these things, traps us into that. Like I, I think to some degree, part of what we can do today will is just give people permission to go look at some other buckets. And do it before that buckets full. Your startup also doesn't have to have achieved everything it's ever going to achieve before you start filling other buckets. You don't have to wait.
Wil Schroter: I don't think it took me a very long time, it took me decades to realize that there were other buckets and and and I don't mean I, I was like so myopic. what I'm saying is like, I didn't understand that anything could be more rewarding, so to speak, than building company, because it
Ryan Rutan: was the biggest reward. I mean, in your case in particular, well, it was, it was freedom and safety for you that you probably never believed was possible. Once you felt that, it's a powerful drug, right? So there's some, to some degree there there is a level of addiction to what we do,
Wil Schroter: right? Yeah, and we have to question self-preservation, right?
Ryan Rutan: I'm definitely addicted to self-preservation, like we, we all should be.
Wil Schroter: One of the things I've learned though is that my ambition expects value. My ambition becomes painful at some point when I don't feel the value is being rewarded, OK? It's when I go to the bar and I order that drink and it's $37 I'm like, you know how hard I worked to be at this bar, and now I feel like a chump, uh, you know, because I'm not getting my value. Again, I quietly grumble by myself. I'm just not that guy that like creates a scene, but in my mind, I'm like, I, I get it. I understand why this is happening. But I'm mad, and the reason is I expect that if I work really hard for something, that I'm gonna get value out of out of that relationship. A good example is a spoiled child. You work so hard to raise this child and provide for them, and you sacrifice so much and then they're a holes and you look at that and you're angry, you know, for all these reasons, but part of that is your ambition in what you you put into this expected a return. Now whether or not that was an entitlement you shouldn't have had is is is subject to question. everybody's different. But that that's why you feel that way. Years ago, and Ryan, I think you remember this, my family and I, we, we had moved to Beverly Hills. We had a nice enough house. It wasn't very big, that that was an issue, but it was like particularly small. And uh, my son was born, so there's 4 of us, we just ran out of room, and we went to go look for another house. After a year and a half because finding real estate in LA is nearly impossible. We find this house in Bel Air. It's like 10 minutes away. We weren't trying to be in Bel Air. I was. Trying to be the fresh prince that just happened to be to be where the house was. Yeah, it's not a lot of inventory. We're ready to pull the trigger on this house. It's really expensive and my wife and I sit down. I'm like, hey, like, this is, this is what I've been working so hard for, like, this is, this is where I cash in my ticket. And my wife, who's my wife for a reason, is like, fuck this. She's like, there's no way we're spending this much money. In getting this little value, right now, and, and we moved back to Ohio the next week, right? So to give you an idea of how committing these work
Ryan Rutan: on on money for value there, yeah.
Wil Schroter: No, there was a point where we were just like, dude, this is so expensive. We're on a postage stamp of land, right? Like it's like, but the time we pull our car out of the garage, our headlight is still in the garage where our tail light is in the street, right? This is like a big house, right? It's, it's crazy expensive and And she was like, for what we're spending, what we could get literally anywhere else, right, has so much more value, would feel like that money went towards something. Here, every time we pull in the garage, it's gonna be a $37 cocktail. We're supposed to feel good about it, we feel like a chump every single time. And and know, and I told her I was like, you know what, you're right. I was like, my ambition expects some value. Yeah and and and when when that the calculus doesn't add up, you feel like a chump.
Ryan Rutan: That's when you have to start to backpedal a little bit and say like, OK, so what is my ambition actually pointing me towards, right? And, and, you know, I think ambitions still welcome, but we have to reprice it. Because ambition is not the enemy, mispriced ambition, right? where ambition just leads to that, you know, that, that inverted value curve. That's where it becomes problematic, right? The
Wil Schroter: I mean when you say mispriced, I think I like this concept, but I want to hear how you think about it. Yeah,
Ryan Rutan: so think about the cost of of ambition in terms of time, capital, stress, whatever, and then think about the the the return, joy, freedom, impact, right? And then think about the how that leads to the decision around where we will get the better kind of cost averaging or return on that investment, right? So if we reprice our ambition a bit and we start to say that like, look, my ambition directed here has a certain value. It's almost like it's it's the same thing, right? So if your ambition, if you're spending your ambition, you turned ambition into the dollars, you're spending your ambition in in Bel Air versus in Powell, Ohio. Those are very differently priced, right? Same effort, completely different value return. And so I think this is where we have to start to say like, what can I point my ambition towards? This is going back to the the previous segment, which is just look at some other buckets. And and start to say like I need to maximize my utility across buckets, not just in a singular bucket.
Wil Schroter: Yeah, and, and I think that for most folks, uh, we get the ambition part. That's how we're founders. It's kind of, you know, what we do, and we're good at that. Where we fail is we, we don't have a sense for will I cross the finish line? Will I win enough Super Bowls? Would I win enough, uh, you know, Tour de France, like, uh, medals, so to speak, right, in life. And so what we do is we just go blindly toward finish line after finish line after finish line with really no endgame in sight. And then at some point we need the 10 slice of. We don't even, we're not, we're sick at this point. Like we've ruined ourselves in so many ways, and all we know is how to eat more pizza, right? And this is just in every aspect of life. So I think for all of us, for founders, we need to know, you know, when to say when. We need to know what our ideal limit is when it's time to stop eating and go, go do something else, go focus on something else, find that other bucket that creates geometrically more value for every bite. Than what we had a moment ago, and I think when we find that other thing, All of a sudden our world lights up again. All of a sudden we're like, damn dude, this is how my ambition was supposed to pay me. It wasn't just dollars, it wasn't just us being on, you know, some the building the biggest startup ever. I was supposed to actually be happier, right? Your ambition as founders, you deserve more from your ambition, right? You worked for it, but if you're gonna actually enjoy it, if you're gonna get what you deserve, you have to know when to walk away from the table and say enough is enough. I'm just so damn happy with what I have.
Ryan Rutan: 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.