When is Enough, Enough?

Welcome back to their episode of the Startup Therapy Podcast. This is Ryan Rutan, 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. We just don't know when to say enough is enough. Yeah. Like Ryan, it's so weird. Like I've dealt with this personally, but I also, you know, we 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. Yeah. This is when anything beyond that becomes a liability. Yep. 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, it becomes our, our greatest strength and our greatest weakness. A hundred percent, man. So, Ryan, when you think about ambition becoming a liability, like what comes, like, like how, how do you manifest that in your head or, or in your own life? At some point, like it's, it's the law of diminishing return.

And look, I think we gotta go all the way back to beginning on this. Like, so why does this start? Right? We started in scarcity mode. Every startup starts in scarcity mode. I don't care if you're funded or not, there's something you're scarce on. We're in life. You got money, you might just be scarce and understanding of how we're gonna 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.

And 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. More always better until those start to come at that cost.

So as you said, right, it 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.

Yeah, and it, it's interesting because like, do you remember like growing up there was this concept of eat everything on your plate, right? I, I clear your plate. I still haven't lost that concept. And I'll tell you. It has it's, it has, 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 foods, right?

So you have this, this dual fo fold problem for me. One, we have access to amazing world class food. At amazing world class prices. And so I feel like we shouldn't leave a scrap of it on the table. Right, right, right. And so I'm now carrying it around my waist. Yeah. I say, welcome to obesity.

And that same concept applies. Yep. We have this idea early on because we're young, we're growing, we're hungry. Right. 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. The irony there, sorry, I just gotta go back like so do you remember what one of the rewards for cleaning the plate was? Dessert. 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. No, it it more unhealthy, right? So yeah. So this is, this is pretty deep. It's very psychologically set for me. Yeah. 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. 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. Yeah. Where I think that's interesting is when we get into this, like you were saying, we're broke, right? Yep. Maybe personally, professionally, and startups broke by nature. That's how we all start, and so. All more is good at that point. Yes. More revenue, more people, more capital, more, you know, you name it.

More is good in our personal life, especially when we're, uh, very young. More is good. Having car is good. Having houses good, yes. Having, you know, family or, you know, whatever. It's whatever your path is and. What you don't hear about along the way is someone saying, so when are you gonna stop? Yeah. You're like, no, I'm eating as much as I can. Oh, like I clean every plate, eat every dessert. I'm like, you know, actually that's gonna end pretty poorly for you. Yes. 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 'em, you know, never get to eat enough. If you're 45 years old, I'm just making up an age and you're like, dude, I'm so broke right now, more ain't my problem. Okay. Right. That I feel for you. Right. So just to be clear, most of the world doesn't have a moral problem.

You know, though, like yes and no. Obviously if you're, if you're under fed, 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 and, and like when we start to adopt that without any sense for what enough looks like, right? Because 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 in other podcast where what you actually need in life. 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 another plate have car, another plate need bigger car. Right. Right.

Have a, have, have all the airline travel I could ever want, need my own plane. Right. Nobody needs their own plane. That's silly. It reminds me of, uh, remember we, we, we talked, uh, episodes past and I, I referenced that, that Joseph Heller quote, uh, he's the author of Catch 22. Yes. Uh, they're at some brilliant, he and Ker vga are at some like big billionaires, uh, penthouse or something like that. Yep. Uh, VGA says to him.

Hey Joe. Uh, how do you feel like this guy's got more an 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? Yeah. Right. It's beautiful. Absolutely beautiful. I love those quotes because I don't think any of that think part of that story's true. It does not matter. Just delightful though. It's a perfect quote, whether it happened or not. I Right.

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? Okay. 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. Yeah. 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 1 0 1 class at, uh, college Yep. 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 he'll ever get.

Yep. 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 the third, fourth, fifth, and sixth or whatever become, uh, significantly less. He's still eating pizza, but the value he gets the utility. Drops exponentially. Correct. Now it, and that always stuck with me. Like I, in, in a weird way, I am always maximizing for utility. I think it's the nature of what we do as founders, as startups.

Yeah. I think it's right. You know, as how do I spend every dollar you build into us? Yep. 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 first three series BMW typically in white. Right.

And we said wherever you were before the three series BMW, until you got that series, BMW is probably the greatest delta of utility you'll ever experience. Yep. In a car before and after that moment was amazing. Yeah. Correct. Right. That that was a zero to 100 moment. Right. Now, once you had that utility wears off and the novelty wears off Uhhuh and you say, well, how do I do more than this?

Yeah. Yeah. You look at the next car and the next car to get, I'm just sticking with cars as a, 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 seven series, BMW. I'm a car guy, so I'm, I'm moving up interiors here. It could be that Bentley, it could be the bug Gotti, 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.

Oh yeah. But it's not zero to a hundred anymore. Nah, it's like zero to 20. Yeah. Right. The zero, 10, sometimes zero to zero. Yeah. Right? Yep. 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? A hundred percent, man. Like I can actually draw that direct comparison because in the last eight years I. I've owned a number of cars, but I've owned two very, very different cars. Mm-hmm. And I got very different level of enjoyment from both of them. One of them was an SL five 50, which is a very, it is a great car, 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 $4,000 clunker of a Guatemalan, you know, off-road vehicle that I just, I loved 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've pushed them off to the side for everyone else's safety and walked home and not thought about it again. Right. Well you, it just such, you also maximized no liability that, I'll give you another example. When I go on vacations and as you know, I hardly ever take vacations. I'm just not. It is correct. Uh, and so when I go on vacation, we usually try to go to a really nice place and 'cause we hardly ever do it.

When I get to the bar, I order the same drink every time. Uh, vodka gimlet. I know exactly. I know exactly what it is. Yeah, yeah, yeah. You do. You know me well. And so it's the same pour of Tito's anywhere in the world. Yep. Right. You know, sometimes less, sometimes more. But it's the same drink. There's nothing special about it. Right. No, I'm not like a bourbon guy or anything like that. Right, right. Nor nor is it a complicated or complex drink.

Like you don't even need anybody who an expert, you cannot mess up. You measure two, two things nice together. Yep. 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. Yep. An $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, yeah. Yeah. 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. You get the most utility outta the first one. It's the second one that should really bother you will. The problem is there's five 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. Yeah. If we were to say, Hey, founder. At what point does your business not need to grow anymore? Like that's heresy, right? 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, yeah. Shut up, right? You're fired. Get a new team. Yeah, exactly.

But what we're really asking in 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 three series BMW, just to get 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, 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 is, 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 that 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 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. Well, think about it. What do those things need to achieve?

What's the end game? 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? Yep. Uh, you, you get things like, uh, you know, I mentioned the first company, uh, that I had 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 just like, it was so stressful and it, it was so unnerving because it's unfixable that I didn't like it. Right. Yeah. Uh, needless to say, we have nowhere near a $10 million a month payroll@startups.com, and I sleep so well with that information. Yeah, yeah.

Right. Like I, I feel like if something goes wrong for us, we can all get in a room and fix it. Yep. Right. So for me, enough is just enough people, just enough revenue, et cetera, 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. Sure. 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 just didn't like it, and so we were like, you know what? It stresses out. 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 VC is because we didn't need what that capital could provide. Really powerful, you know what I mean? Yeah. It's nice to be able to make those decisions. Right. And I think that that is a, 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? Yeah. 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 win 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, right. 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. At the same problem. So we wanna grow bigger, we have to add more head count, 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. 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 right, then it just has to be recognized as not being worthwhile. I'll give you an example of where I see this as a milestone.

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, a friend of mine, a founder, uh, that'll call me out and say, just completed my exit. I mean, for all the obvious reasons, I can never get enough of those calls. Right.

Um, if you're listening to this podcast and you ha have had an exit, and Ryan, do you remember like a couple months ago, uh, gentleman reached out and, and by the way, uh, if sir, if, if you remember that we're talking about you Yes. And he said, Hey, I've listened to podcast for a long time, built this business doing 50 million a rrr, et cetera. You know, having just, you know, it's, it's incredible, et cetera. And I'm like, I can never get enough of those emails. Right.

You know, just talking about those success stories. The outcomes, talking about successes. Yeah. 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 exit. I've come to some money. If you're one of them, now we're 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 gonna high five you. I'm gonna warn you. Yeah, yeah.

Here's what I'm gonna tell you. It, it's the same thing I tell everybody. Don't fuck it up. Here's what I say. Yep. You've already won. Okay? Yes, you've won. Now all you can do is lose. That's it. You have to change your mentality. Right. It's not time to double down. Right, exactly. It's not the answer. 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. Right. You can go all the way.

Unfortunately, that that often ends up going all the way to zero rather than all the way to point anywhere else. Well, that's my point. This is exactly kinda 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. That's it, man, right there. Post win, the risk profile flips. Right.

All of a sudden downside completely outweighs upside, and I think we just don't get that. We've been in a, I must win to achieve upside. The minute you do that, right, continuing to push it, just the risk profiles reversed. All of a sudden the, the, the cards have all been flipped. I think we just don't recognize that it's certainly not soon enough in most cases. 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 a thousand times before you, which means the answer already exists. You may just not know it. But that's okay. 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 dayLong@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. 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. You beat life. You won, you were the best around Dun, right? Yeah. And like he's got that, um, and, and he, uh, I, I can't even say that without finishing anyway, but he won. He was like, Johnny Tour de friends, right? Yeah. Uh, like he, he was the guy.

And remember, he had lived strong. He had, um, yeah. I mean, dude was printing money, right? He was just like, he, 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. Yeah. Like the reason you were the best is 'cause you, you, you want to be the best, but the moment you jabbed yourself for the first time.

Yeah. That's the moment where you jumped the shark. Right? That's the moment. Yes. 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 FRI in the NFL. Right Tom? We got like seven Super Bowl rings. Right. If you get an eighth, no one will even remember. No. Right. Like no one will know the difference. Yep. And the next guy that, that knocks you on your ass and you don't get back up from Yeah. Right.

You lose everything. 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.

I think for many of us, you know, we don't have to be Tom Brady, Lance Armstrong to hit this threshold. Correct. For many of us. We hit this threshold and, and you know, lemme put, put, put this together when we hit $200,000 a year of income. In other words, at $200,000, 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.

Yeah. 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 understand, I, I'm, I'm normalizing a little bit anyway, in America, in most parts of America, let's say. You couldn't buy most of the things you need now. It doesn't go as far as it used to. Right, right. But, but you couldn't get probably 80% to 85% of your utility in life, house, car, family, et cetera. 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. 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. Yeah. That tend to be what you really pay in the price to try to get to that next level.

Go back to your pizza analog, right? You get the most utility outta the first slice. So let's compare this now, let's say, okay, you still want another slice? The price of that slice just doubled. You're gonna get less utility, you're gonna pay more and just double the price of each slice. At what point do you stop eating pizza? Probably after about the third 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. 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 day as 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 was time to hang up the Spurs, right? But in my mind, whatever that was, the next one had to be two to three 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.

'cause 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, right? The fact all the people out there with zero hits are gonna judge you as being a one hit wonder like. Who gives a shit, right? Didn't give a shit. Oh yeah, he got lucky one time. Okay. Cry about it on your yacht. Ask, ask Rick Asley if he cares, right? He doesn't. He doesn't care at all. Every time you get Rick ruled, he gets paid.

So with that said, I'm saying like for founders, they get into this thing and they're like, okay, 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 a hundred percent mapped to sheer terror. Yeah. Like PE people think it's, it's about greed. No, mine's all fear. I, I operate completely on fear.

The greed or anything I get to have that, that comes out out of a, at the cost of fear is just found money. Yes. It's all driven by fear. I'm just doing this for the fear folks. The money is a fringe benefit. 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.

The irony there is that that can absolutely be what ends up causing people to, to Exactly. It's as if we're in the ninth inning and, and we're up and it's the like way at the bottom. We're like, let's ask for some extra innings. Why? All you can do at this point is below 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 it from.

So, because defining that metric is gonna be very, very individualized, right? Mm-hmm. 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?

I went through this catharsis last year when I turned 50. Right. And it's just, it's kind of a seminal year. Sure. 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 is like, oh, you're a young pop. I'm like, dude, no I'm not. Right. Yeah. 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, I'm not playing that game. Not young. 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? Yes. 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.

Yep. 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 was 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. 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. Yeah. Right. Like I can get a fifth slice of pizza. I just don't, 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 fifth 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.

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 and used the house analog. I think at some point when you're just chasing more of the same thing, I think it also becomes problematic. Like at some point, correct. Probably worth branching out a little bit and kind of like, yep, redefine what does more actually look like. Like I do.

I just need more the same thing, like my son Jack loves trains, loves 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 'em out like one a week, one here, one there, one here, one there. When you get to the 12th, then 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, five 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 or the size of the garage the cars are in, at what point are we asking ourselves? Like particularly like is, 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. 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 bing with business, no longer added any more joy. It was my fifth slice of pizza, you know, or, or, or wherever you tap out, right? And I started to say, huh, that's interesting because up until now, those book buckets always felt so empty that, 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 nine companies. If I start a 10th sort of who gives a shit, that doesn't mean I had no ambition or that somebody day I won't do it. I just know now that whereas before it was a massive part of my, my goal, my path. Yeah. 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 and other, and some people are listening to this going, oh, you, you think so, idiot. Yeah, right. But you know, your family bucket, your health bucket, your relationship bucket, your spirituality bucket, you know your fitness bucket or 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. Will imagine if you spent as much time and attention and purpose and passion on your relationships as you did with your business. You were that intense about making your relationships and I was like, well, I think everybody would hate me, but I would've exited three of them. Four would've failed and I'd still be running one. Exactly. Exactly.

But, but it was, it was a good point. Hey, will, you know, uh, there are these other buckets that you woefully under invested, 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 pizza. Pizza feeling about, yet you're back, back to full utility. You're back to full utility. Right. Exactly. And I think that's where it's, it's this, you're gotta hedge your bets on more.

You gotta spread things around a little bit and, and just so much benefit to it. Right? I think you named off a bunch of 'em. For me it's been relationships, wellness, some craft and projects. A lot of sport and philanthropy have been the things that have landed. 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 the, the other things that I was chasing hadn't for some time because I'd already filled those buckets. Like another part of it's novelty, like a hundred percent. Like I said, when if I go and start a 10th startup, there's nothing novel about it. Yeah. Something we'll, we'll do maybe the team, et cetera, but I've been on the journey a million times also.

You know, that's kinda what's cool about this business is I basically get to live all these other lives Vis, yeah. 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 had 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? Yes. Was so exciting. Yeah. 'cause it was so new novel. Zero to 100 moment. I think part of what I lost on this path is I ran out of those moments. Yeah. 'cause this bucket was full. The 5000000th line of HTML code I wrote. Was not nearly as exciting. Right? Not nearly as exciting.

Did it's, we can all recognize that we go 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 the, where we spend most of our time, all of a sudden we're like, well, haven't rethought that in a while. Why? Right. And, and I don't wanna believe people are all that one dimensional.

I don't wanna 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.

Yeah. And again, maybe you did, maybe you did the full analysis and this is all that matters to you and all the power to you. 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 I think part of that, especially in the founder space, is this sense of responsibility to a mission, to a level of achievement.

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 bucket's full.

Your startup also doesn't have to achieved everything that's ever going to achieve before you start filling other buckets. You don't have to wait. 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 Yes. Than building company because it 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. Right. So there's some, to some degree there, there is a level of addiction to what we do. Right. Yeah. And, and we have to question it and self preservation, right? Yeah. But I think, well, I'm definitely addicted to self preservation like we all should be. One of the things I've learned though, is that my ambition. Expects value.

Yeah. My ambition becomes painful at some point, of course, when I don't feel the value is being rewarded. Okay, yeah. Yeah. 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 work to be at this bar, and now I feel like a chump because I'm not getting my value again. I quietly grumble by myself. I'm just not that guy that like creates the 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. If I work really hard for something that I'm gonna get value out of, out of that relationship. Right. A good example is a spoiled child. Yeah. 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 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. Yeah. Everybody's different. That's why you feel that way. Years ago, and Ryan, I think you remember this, my family and I, we had moved to Beverly Hills. We had a nice enough house. It wasn't very big. Not that that was an issue, but it was like particularly small. And uh, my son was born, so there's four of us.

We just ran outta a room and we went to go look for another house after a year and a half. 'cause finding real estate in LA is nearly impossible. We find this house in Bel Arrow, it's like 10 minutes away. Yeah. We weren't trying to be in Bel Arrow wasn't trying to be the fresh prince. That just, just happened to be where the, where the house was. Yeah. Yeah. And not a lot of inventory. We're ready to pull the trigger on this house. It was 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 Yeah. In getting this little value. Yeah, yeah, yeah. Right now. And, and we moved back to Ohio the, the next week. Right, right. So to give you an idea how Committ talk about flipping, were talking strict on, on money for value there.

Yeah. No. There was a point where we were just like, dude, this is so expensive. Yeah. We're on a postage stamp of land. Right. Like, it's like by the time we pull our car out of the garage, our headlight is still in the garage where our taillight 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. Yeah. We feel like a chump. Yeah. Every single time. And, and No, and I told her, I was like, you know what? You're right. I was like, my ambition expects some value. Yeah. And, and it, and when that the calculus doesn't add up, you feel like a chump.

That's when you have to start to backpedal a little bit and say like, okay, so what is my ambition actually pointing me towards? Right, right. And, and you know, I think ambition's still welcome, but we have to reprice it. Because ambition's 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 add you mean when you say mispriced, I think I like this concept, but I wanna hear how you think about it. Yeah. 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? 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 you ambition, if you're spending your ambition, you're turned ambition into 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. Right?

Right. And so I think this is where we have to start to say like, what can I point my ambition towards? And 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. Yeah. And, and, and I think that for most folks, uh, we get the ambition part. That's how we're founders. That'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? Yeah. When I win, win enough, uh, you know, tour de France, like, uh, medals, so to speak, right? Like in life. And so what we do is we just go blindly. Toward finish line after finish line. After finish line. Yeah. Yeah. With really no end game in sight, right? No. And then at some point we get the 10 slice of pizza. We don't even, we're not even, we're sick at this point.

Yeah. Like we ruined ourselves in so many ways. Yeah. 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 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 work 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. 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 bootstrap founders and the advisors helping them win in the startups.com community.

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