Founders Don't Retire

Welcome back to the episode of the Startup Therapy podcast. This is Ryan Rutan, joined as always by Will Schroeder, my friend, the founder and CEO of Startups.com. Will, as founders, do we really retire, or do we just stop one company long enough to start lying to ourselves about not starting the next one? Where the fantasy is that after this exit we'll finally sit on a beach and relax forever, but what we usually wanted wasn't retirement, right? We wanted relief.

So Will, why do founders keep mistaking- I need a break for I'm done building. The fundamentals of being a founder is that you're a builder. You want- Yeah to build stuff. Like that's, that's how you got here. That's problem solvers, right? Right, yeah. It's like saying an, a artist saying, "I wanna retire from art." Uh-huh. No, you're still an artist. Like you still create. Yes.

Yep. You wanna retire from the bullshit that comes with the job, right? Yeah. But that doesn't mean you don't like the work, right? 'Cause that, that's very different.

Now, I'll give you a different example. Like, uh, growing up, my, my dad was a carpenter, and we'd go on the job site together, and I'll never forget sitting there on one of the job sites toward the end of the day, and I'm like, "Dad, isn't this awesome?" Like, I was like, you know, 14, 15. And I was, "Dad, isn't this awesome? Like, we built something that's never existed before," and I'm, like, creating this whole narrative about it. And my dad looks at me, right?

And he's like, "No, it's not." He's like- No … "I'm 40 years old. My back is shot-" Yeah … "my knees are shot." He's like, "We'll do anything but this," which of course is the first thing I did as soon as I had an opportunity. But, like, what he was saying is, like, "This job is painful," right? Mm-hmm. "I don't want to do it." Yeah. And he's right. That is a painful job. You would want to stop doing it as soon as humanly possible. What makes our pain different?

'Cause I would argue a founder's, uh, y- I m- we don't end up with bad backs and bad knees most of the time. We, we can, because we get into all kinds of other nonsense. But- Mm-hmm … like, what makes our pain different, right? Like, why is it that we're addicted to the pain? I would say that the pain isn't any different, it's the why we were doing it that's different. Ah. See, my dad didn't give a shit about being a carpenter, right? Yeah. Like, all he cared about was- Means to an end.

Yeah, yeah. I, I can swing a hammer, I jump in my van, somebody pays me, right? Like, that's pretty much it, right? But that's not why we do what we do, which is why we do it for free for so long. Yeah. Right? You know, we do it with, with a expected future payment that rarely comes. Yep. But we do do that.

You hear never of carpenter that's like, "Man, I spent, like, you know, four, five years working on this house, and you know, I didn't think I'd ever get paid for it, and lo and behold, I didn't," right? "But I loved it so much." Yeah. "I just care about building so mu-" You literally never hear that. We are, we have a calling.

Like, we fundamentally, you know, as, as founders, have a calling to want to go build, and it is antithetical to what we're born to do, like, what our DNA is, to say, "I want to stop doing it," right? Yeah. And so when we think about retirement, which is quite literally the cessation of doing, you know, what we're used to doing, we think about it like, "Oh my God, when I get to retire, things are gonna be great." And I'm like, not really.

No. Not- Not unless the world has also run out of problems, right? Because as you said- Yeah … man, a, a normal person retires to stop working.

Yeah. I know what retirement looks like for me. I can already see it, because it happens in these little brief moments now. I didn't have to fully retire. Today I went downtown. I had to go to the dentist, and then I met my wife for lunch. Uh-huh. And but as I was sitting at the dentist before, uh, she had gone… We both had appointments. This is like, this is what you do now as, as couples of our age. We go to the dentist together.

So I'm sitting there, and I've got a few minutes to just, my brain just goes where it wants to go. And I'm thinking, I'm watching my wife pour a glass of water, and I'm thinking, "Man, water's gonna be one of those resources we really have to be careful of in the future." The next thing that happens is I get an alert on my phone from Perplexity, and I go, and this is a big part of it, right? AI is sucking up a ton of water to cool data centers. Uh-huh. Where does my brain go next?

"Hmm, I wonder if the thermal exchange between data centers and water treatment could be combined. Could we start putting water treatment facilities around data centers- Right … and not just make the process more efficient, but g-," right? Th- this is what happens to a founder. I was left- That's how we're built … I was left with four minutes. Four minutes. This is how we're built. This is how… And, and, and that's the point of this, right? So- That's retirement.

And you know, Ryan, it's, it's funny because as we g- continue to get not younger, this- Yes … conversation starts to become more and more popular, uh- Yeah both with ourselves, uh, with our peers. And I- Now, I might not think I'm getting closer to retirement, but my hairline might disagree, right? It's like, it's already, my hair started retiring five years ago. Yeah. It's just waiting for me to catch up. You, you… it's the canary in the coal mine.

I think about it like this. I think that there, there is a, a very misplaced dream about what retirement means specifically- Yeah, 100% … for founders, specifically for founders, right? And I thought today we could kind of unpack why that dream is so broken. And, and by broken, I simply mean that what we think retirement can or should be is a myth.

It's not that we can't- Yeah … do it, it's that what we think it'll- We don't … w- we'll be for, it backfires in a huge way- Yeah … every time, right? Like, every time. Yeah. And I think it starts- I think it starts with the dream. Ryan, w- when you think about the dream of retirement for a founder, we're generalizing, how do you envision

it? I don't anymore, because we've done this podcast, uh, on, on like what retire- the fact that you and I have both sort of play tested this, right? Like- Mm-hmm … we both went and did some of the things that we thought we'd wanna spend our time doing if we just had lots of time. Turns out I didn't wanna do any of those things full-time. Mm-hmm. Turned out that the way I was already doing them as my part-time hobbies was absolutely enough of those things. Yeah, yeah, yeah.

And so we figured out, like, oh, founders don't retire. We reload and then we re-tire, meaning a re dash, hyphen tire, right? Yeah. We tire ourselves again. So we, we get tired- Yeah, yep so we retire, and then we reload, and then we re-tire. Like, this is what we do. Because the, the exit doesn't kill the builder in us. Right. It just clears the calendar, and what do you do with an empty calendar, Will? Add more stuff. I fill mine as fast as I can. Yeah, yeah. Right?

I don't wanna stop building. B- bigger task list. But Ryan, I, I think that for almost any founder, there's this dream of retirement, in some cases a fear of retirement. Sure. That, that, that would be mine. And the dream is I can finally do the things that I wanna do without my startup being in the way or, or, or my founder job being in the way. Yeah. And my argument is, I don't think that's actually what you mean.

No. What, what they mean is, I want a version of my future that doesn't involve the pain that comes with being a founder. Yes.

The general, like the prototypical retirement, right, is that we all go to the beach, right? Yeah, right, right. Let's just use that for a second 'cause it's, it's a funny- Yeah … it is a funny metaphor here. So the beach sounds amazing when you're drowning, right? When you are just overwhelmed by your business, when you're drowning, the beach- Oh, I feel like- … is the best place … you're in the, in the ocean on the beach. I was like, I guess. Yeah, yeah.

You're, you're coming from the ocean to the beach, right? Yeah, okay. It sounds amazing, and it is. The beach is the most amazing thing when you're actually drowning. But after you've rolled up on shore for a bit, you've hacked out the water, and you've, you got a little bit of sunburn, it gets really boring once you can breathe again, and that's the problem, right? Yeah. Like, it's the overwhelm we're trying to escape, not the actual work.

It's the way the work is happening that we're- Yeah … trying to get away from. And so, yes, I think every founder should have a dream for what a sustainable and healthy and happy version of running their company looks like. To me, that's probably the closest we get to retirement. But I think that, that dream, if misplaced, if misunderstood, is a- Yes huge problem.

I think if we're thinking, "I have to retire," ergo stop doing what I'm doing, sell my company, whatever, in order to like kinda get this sense of relief that people usually get with retirement, I think that's a dangerous proxy. I think it's a dangerous proxy, number one, because it implies that you're gonna stop doing What you were meant to do. Yeah. Now, now let me, let, let me zoom out a little bit, 'cause I, I wanna make sure that this doesn't get misunderstood.

If you're working 60 hours a week and banging your head against the wall, and you're worried about payroll and everything else like that, no sane person would say you should do that forever. This is not what we're saying. Correct. Right? What we're saying is the thing inside you, of all of us, that wants to build should never be contained. Should never- Correct … be contained.

And I think that's where we think of retirement as this idea of putting to pasture what it is about us, and I don't think putting that creativity, that productivity, that brain that wonders how you're, h- how you're gonna cool off data centers, should ever be put to rest. If anything- Yeah … I think it should be cultivated for as long as it possibly can. Stay in motion. I mean, it's… That was one of my, my grandmother, who's now 101 years old, that was her advice.

Like, find something that, that you can do, that makes you happy, that you can keep doing for as long as possible, and just never stop doing that thing, and that's the secret to a long and happy life. And like, gonna have to kind of trust her on this one, 'cause she's, she's, she's got the math to prove it, right?

Just for fun, I pulled up our retirement plans, and it turns out each and every one of them, b- uh, uh, of our retirement plans, Will, has a 90-day vesting cliff before the next idea shows up. That's pretty tri- Actually, let's stick with that for a second, because for a lot of founders, they get a version of retirement on an exit. Yeah. And it goes the same way every single time. Yep. Every time they're, they're like, "Oh my God, I'm

so excited. I, you know, I can finally relax," and, and that is true. Yeah. You had a ton of crazy shit going on five minutes ago. You don't have that stuff going on right now. Yep. And you have cessation of that pain. Awesome. Yes. You deserve it, and I'm so glad you have it. But then what? The first month is margaritas, the second month is domain names. Yeah. We know where it goes. We know where it goes.

And it's like y- you get into this thing where, again, founders who have the exit have the opportunity to see what it's like to not put their trade in, in play. And I think you find out real, real quickly it sucks. Yeah. It sucks having this incredible skill and not be able to use it.

Let me tell you where I've seen this most painfully and most consistently. With athletes, right? Nothing sucks more than an athlete who can't be on the field again. Mm-hmm. Right? An athlete, like, like you and I have some friends in common, some, uh, coming out of the- Yep NBA, et cetera. Yep. And their issue is they stood in a stadium, right, of 20, 30, 50,000 screaming fans, right? Yeah. They hit the three, the place went nuts, okay? Hit a lot of threes. Right, yeah, exactly.

We're talking about the same person. Yeah, we are. Uh, a- and, and then they turn 34, right? Yeah. Imagine. I, I, no, that's my point. Ray Allen's 34, right? The reason I'm bringing up athletes is twofold. Yeah. One, because their cliff is so early in life, which you s- Yep … the back half of, of that is, is very difficult. And it's such a specific calling, right? And it's- Correct. Yeah. And you can't replicate it, right?

I mean, like- Correct … you can Tom Brady it into your s- senior years, but even- Yeah then you can only take it so far, right? I say this because- Unless you're Jack Nicklaus. Apparently that guy can play golf forever. Or Hulk Hogan. Or Hulk Hogan, who can- Yeah. Uh, yeah, yeah. Who came back 6,000 times. But, but I, I guess what I'm saying is for these folks they don't have the ability to go back to doing what they were doing, right?

You know, they go on to become ESPN commentator or something like that- Yep … which is like a fraction of what they were doing before. But for founders, we can Warren Buffett that shit. We can do it forever. We can go. We can go forever. Right? I just talked to a founder, a friend of mine who's now 64, and he's like, he had put on his LinkedIn retired. And I reached out and I said, "Stealth mode?" And his response was, "Fuck, you caught me." It's like, you're like, "Ah, you're not retired.

Like, what are you talking about?" Yep. Uh, so but this is the way it goes. It is. And, and so when we talk about, when we talk to, to founders who said, "H- hey, I'm gonna retire," we always say the same thing. "Let me know when you're done." Let me know when you're done. Yeah. Right? Yeah. Because you'll always be done. Let me know when you untire. Yeah. Yeah. And so, like, it's like this for me.

Every single time I go on a vacation, an actual vacation, and Ryan, as you know, I suck at vacations, so much so that my family now leaves me behind. They're just like, "You're so bad at this, we don't even want you to go anymore." We don't even… Yeah. They're awesome, but they just know that the entire time my head is elsewhere. It shouldn't be. Yeah. But it is. Yeah. And so here's what happens. Every single time I try to s- set up a vacation, I have the same game plan. This is kinda funny.

I'm gonna overwhelm myself with things to do, right? Uh-huh. Right, right there you can already tell it's going the wrong direction, right? I'm gonna overwhelm myself with tasks of things I have to do that don't involve my job- Yeah … in order to, like, force myself to be having fun, I guess. It has to feel like there's some other meaningful outcome from what you're doing, otherwise you can't just go and do nothing. Yeah. If I'm not checking a box, I'm really uncomfortable, right?

Yeah. So I have to have read a book, or I have to have listened to a podcast, or I have to have, like, done something, right? Yeah. I always have checklists going into my vacations. Yeah. My checklists never get checked off. Whatever I said I was going to do, I never ever, ever, ever do it, because after I get to maybe the second item, it's the same routine every time. I'm like, the more interesting thing was the thing that I, that I left behind. Yeah. It was… Yeah. Right?

And so the last time, uh, we got a place that we stay at in Florida, and the last time I was there, by the second day- I had come up with some reason that I had to figure something out. My in-laws, you know, had, had like their condo in, uh, uh, in Florida, and we leave stuff there. Like, the kids leave, like, toys and stuff they- Sure wanna use. Yep. My wife leaves changes of clothes and everything. Do you know what I leave there? One thing, a 34-inch external monitor.

That's the only- Yeah, yeah … thing that, that, that I leave there. Right? I have the exact same setup at my in-laws in Florida with a gas pump arm. Like, I've got the whole, like… You know, you've seen me do this. Yep. I have a second podcast set up down there. Like- Yep … I've got, I have my studio stuffed in the top of a closet down there for when we go. And this is by no means a recommendation or endorsement to do any of this.

If you can go on a vacation, enjoy a vacation, by all means, enjoy a vacation, right? So, and, and this isn't me saying, "Yay, me. Look how good a…" It's me coming to the realization after a while that the thing I love, the thing I absolutely love, is creating. I love to create. Like, to me- Yeah … a vacation would be me creating nonstop, right? Yeah. So the idea of not doing that, of saying, "No, you're gonna sit by the beach and stare at the ocean and sip a margarita," is- Yeah torture, right?

Like, that is- Send me to the beach … worst possible outcome. I have- I'm, I'm out in the water. I'm like, "What kind of animals can I catch? What can I dig up at the bottom? How big of a sandcastle can we make?" Like, something has to be happening. Tell me, man. You brought up something funny, which is it's like, you know, you need the checklist. You gotta feel like you're doing something. I have realized that I've even started, 'cause like you want there to be a meaningful outcome. Mm-hmm.

Over the last couple weeks, sometimes I stack these things, right? So, like, because certain things are meaningful for different reasons, right? So, like, I've, I've been, I've been doing a lot of running in the mornings lately, and that's great, and that has an outcome. Yeah. But that wasn't enough for me. So what have I started doing? I have my, uh, Fireflies app that I turn on. I've got my headphones on, and while I'm running I- ideating blog posts. I'm thinking about marketing funnels.

I'm, I'm talking. I'm basically brainstorming while I'm running. And to make it even more pathological, now I've started conducting founder calls, and I'm doing, like, one-on-ones with people while I'm running. So I'm giving advice while, like, panting- Right? … into their ears the entire time as well. It's fantastic, right? Wow. I would like that so much. Because why not check two boxes if I can? It's pathological.

Here's what I would say, though. It's because there's no substitute for what we do, right? Yeah. And w- when I say that, I mean the world of creation. There is no substitute for creating. For creators, there is no substitute. For everyone else, like, my wife couldn't give a shit less about a- any of this, right? Like- Yep … she's like, "I'm gonna- I'm going by the pool. You know, give me a margarita," right? Like, she's, like, totally good. Yeah. Can take both. Right. Exactly, right?

But for me, and I think, you know, for founders in general, we have this gear that, th- this calling, you know, that I don't feel like we appreciate, right? I think for a lot of folks, they don't realize that, like, again, what we do was never really about the job. The, the job was- Yeah … work, et cetera, but it was about mission, right? Yeah. It was about mission. Startups, th- they're not a job. They're a mission. It's a problem we've set out to solve. Right.

My dad working on the job site was not on a mission. He was on a mission to go home. No. Yeah, yeah. He was like, "I gotta, I gotta get, stop doing this," right? How quickly can we finish this, get paid the same amount, and watch the Braves play or whatever it is, right? 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 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. There is nothing more exciting, more fulfilling than when- Yeah we are on mission, right?

When we are challenged, when we are creating, when our, our minds are exploding, even though it has so many negative consequences along the way, economically, emotionally, physically, you know, you, you name it. Yep. Right? They're all there. And all those costs are real.

But let's go back to you running. I would equate it to a triathlete. What a triathlete has to do for like an Ironman, to prepare for an Ironman, is grueling at best- Mm … and punishing at every level. But the idea is they're on a mission, and that mission is to complete this objective, right? Yep. And when they do, the feeling you get from crossing that finish line- Yeah right? Pure euphoria. There's nothing else like it.

I think what happens is, this is the folly, I think what happens is we believe that we can get that same outcome, that same feeling, without training, without running the triathlon. Yeah. Right? Yeah. They're like, "Oh, well, I don't wanna do all the running, but I want the part where I cross the finish line." Yeah, the finish line looks cool. Yeah. How do I… Can I just start near that? Just one of those instead. Let me start there. And I think that's what we misunderstand.

Like, all of this hardship, and, and there's lot… Of course you want less of it, okay? Uh, again- Yeah … there's no argument there. But the idea that, that you wanna make it all go away, you wanna take the hardship away, also means you're gonna take the upside away. Yeah. And the upside ain't small. And I don't mean financially. Yeah. I mean m- maybe, maybe if things go well. The excitement- Yeah … of running the race, of crossing the finish line, man, there is no substitute for that. Yeah.

I think we start to dream about retirement when what we really need is just, it's recovery, right? Yeah. To me- Oh, 100% recovery. Yeah. No doubt … this, this desire to never work again is the incorrect framing, right? It's a signal that the current way of working has become unsustainable. Yeah. Of course it is. Right? And so relief- This is a hard job, man … from stress feels like freedom. Yeah. And it is, but it lacks fulfillment, and I think that's really the problem.

That's what draws us back in. So this fantasy of retirement, generally speaking, forms at the lowest energy point, which also makes it a really bad life design blueprint. Like, you don't wanna be sitting down and doing that, right? Retirement for founders is just like, it's burnout wearing a Hawaiian shirt on a beach with a Mai Tai. Like, what they, they don't mean that they, they wanna retire. They mean that they want the pain to stop, right? You said this before, Mitch.

The, the, the pain- Yeah … needs to stop. The, the dream isn't no work. The dream's probably something like no panic, no pain, no fear. Right. The relief isn't your calling. It's not a switch. It's not like, "Oh, now I've earned relief. It's now my new calling." No, that's the pressure valve. Yep. Right? And we definitely don't want to design our entire future, uh, from our, our most exhausted self. 'Cause well, how often have we seen this, this play out, right?

Like, founder sells, disappears for a few months, kind of plays golf, sleeps, finally breathes, whatever. Yeah, recovers. Right. Around month three they start saying stuff like, "I'm not starting a company, but I've been thinking about this market," right? Yep. It's a… And to me, look, that's not retirement failing. That's your nervous system coming back online and you finally being back in the, like, I can build.

Yeah. And so rather than have to think that you have to completely extricate yourself from the first business and kill it or sell it or whatever, that you can do that. Like, I, I think the, the idea is that we have to recalibrate how we're running what we're doing now and make it sustainable, right? Right. So I, I think we really have to separate recovery plan from retirement plan here.

I agree, and, and I think that w- we can't deny that what we do is a calling, right? Like- Oh, it- … we do what we do because we're- Some people are and some people are not, right? Like it's- Yeah … it's pretty clear. We do what we do 'cause we're fucking good at it, and the idea of saying let's find a way to take that away from ourselves is pure folly.

I just- Yeah … I, I, I don't believe there's a world where the person who is, is absolutely stellar at building- has said, "I was so good at that, that was my calling, but now I golf and that is so much better." Yeah. And, and look, and maybe you love golf so much- That's a substantive- … that that's true. I hate golf, so a- again, this, it's probably not a fair analogy. However, however- I like driving the cart. Does that count? Yeah. I like drinking on the cart. It's fun.

I don't care if it's going anywhere. You drink, I'll drive. How about that? Yeah. Perfect. The way I look at it is for folks that were built to do this, I say this all the time- Yeah … if you were the kind of person that was built to be able to retire young, then the last thing you're built for is retiring young. No. Right? Climb a ladder and jump off it. Yeah. Like, that's, that's how you do that.

I'm just saying, like- Yeah … if you're the kind of person that had the capability and the drive and ambition to be able to retire at 37 years old, just, you know, as an example, then you're- Yeah … not the kind of person that was intended to be sitting on a golf course- Right or a country club for the rest of your life at 37 years old. Like, those two things are- Well- … run polar opposite.

Yes and no, but play that out for a second because I think there are people who have set that up as… Now I'm, I'm not gonna say that they're correct about what their dream is because they probably haven't played chess, they don't know. But I think there are people who are built to do that kind of thing, where it's like, because that was their motivation.

Maybe. Their motivation was- Yeah … go find path to money, work hard, do these things so I can retire, and I think there are people who aren't built that way. I'd say that's, that's a lot of corporate people are built that way. Yeah, oh, that I agree. Their motivation was that thing. Yep. I agree with that. That wasn't our motivation. That becomes our motivation later when we're like, "Holy shit, I'm tired. I'm just, I'm really tired." Is retirement less tiring? Is it? Why is it called retired?

Right? Like, I don't wanna be tired anymore. I wanna be something else. But I think we gotta be really careful, right? 'Cause again, like, leisure will remove some of the stress of the business, but it doesn't replace the meaning that it gave. So I think that's the difference. That's… Yeah. I think that's the difference, because for us, the business is the meaning, right? Yeah. It's the mission, it's the purpose, it's all that stuff. Whereas, so some other people, the work was a means to an end.

Yep. Like in your, in your father's case, you know, the, the houses weren't like, "Once I build, I wanna build 300 homes and know that I've put, you know, families under root." Like, that wasn't his thing. He was like, "I want-" Yeah. It's not a mission "swing hammer, get paid." Bed Be done Right. That's it Right. That's it. I think for creators, right? Now, again, l- let's talk about something slightly different. I wanna cautiously use this, this analogy.

Let's say you were a stock trader, right? Who, who are notorious for making a voluminous amount of money in a short period of time. I am a stock trader of the exact opposite sort. I'm good at the opposite, the opposite. Yeah. I can, I can lose money really fast. Right. So, and let's say once again, at 37 years old, you've made enough money, you never have to work again.

Yep. And I would argue you're coming from an industry that is so cutthroat and so- Yeah painful and so grueling that th- you had every reason to not wanna do it anymore. I don't know that there is such a thing as a calling within that. Well, okay, so, so here's what I would say. I wanna be careful 'cause, you know, we're making- Yeah … a lot of generalizations. That to me is less about mission and calling. Mm-hmm. And that's more about just means to an end.

I- in that case, the mission is that is the means. And I think there are times where that absolutely is the thing, but it's not for us. I think for what we do as founders and creators, I don't think we have that gear. I don't think it's just a means to an end. I think because of who we are and, and how we operate as builders, our mind constantly wants that challenge. Yeah. I don't think we are satisfied. I don't wanna use happiness 'cause that's an amorphous concept.

Yeah. I don't think we are satisfied unless we are latching onto that type of challenge, and there is no other challenge that most people can find- That even pale, anything pales in comparison to starting a startup, right? Yeah. Which is why everybody goes back to it. Definitely. Because we're like, damn, that was the only game worth playing. And it's funny too, because it's not even just the successful, right?

Like, how many third time failed founders do we know who are working on their fourth startup? Oh, yeah, 100%. Right? It doesn't- It's not just like, "Oh, that worked. Let me do it again." It's not even that, and I think that's what points out that it is a calling, and it is a mission-based thing. It's not just a means to an end. Because if you failed three times, clearly this doesn't seem to be the means to an end. Not that type of end, right? Not a retirement, certainly.

And so I think that's where we have to kind of figure out, like, where are we at in this whole thing, right? Of course. And of course, like, we get closer to retirement, like, we're not gonna miss the stress, but damn, you're gonna miss the voltage of being plugged into one of these things, right? Okay, so stick with that.

I've got a bunch of friends that have retired relatively young, right? Okay. 30s and 40s, okay? So they, they made just enough money that they just don't have to work anymore. Uh-huh. And some of them have gone maybe 10 years since then, and they haven't, you know, started another company. And th- these are lots and lots of people that I'm kind of parsing through my, my rol- my mental Rolodex in this. And here's what I would say.

For all of those folks, some of them are satisfied, which sounds wonderful. They're not charged the way they used to be. Right. Yeah. Satisfied, like, "Man, I'm glad I get up in the morning. I don't have anybody bugging me," you know, release the pain. "I don't have any VC that I gotta chase down. I don't have, like… You know, whatever. Like, my satisfaction comes from the lack of pain," right? Yep. Which I, I get, but there's no charge anymore.

Yeah. There's no, "I jump out of bed, and I run to go do this, 'cause I am so goddamn fired up," right? Yep. It looks more like this. "Man, it's great. Man, I get up in the morning. I get out of bed kind of whenever I want. I still get, you know, keep a reasonable schedule. Go work out in the morning, have lunch with my spouse." You were saying that's the thing, right? Like, you know, have lunch with my spouse. Piddle around a little bit, uh, contact a few buddies.

Sometimes I'll do g- golf or I'll do this or that, and I just kind of do whatever I want whenever I want. And again, that sounds wildly satisfying, but it sounds like zero charge. The charge was when you were so excited and on mission about what you were doing, it didn't occur to you what time it was. Yeah. It didn't occur to you how much time had elapsed or how much, like, pain you had endured because you were so fired up, right?

Yeah. Like- We, we get to the point where, like, the thing that nearly killed us yesterday before we went to bed is the thing we wake up excited to do the next morning, right? Correct. 100%, man. That's it. That's how we're built. Right, and so th- this idea of retiring and not doing that anymore, not having that purpose, that charge, to me is terrifying. Oh, it is.

I- in very simple terms, here's the transition that you have to make in order to go from one to the other. You go from creation- To consumption, right? You go from making things to- Yeah … just taking in what's there and absorbing- Yep … stuff, and it's, it's not the same thing, right? Uh, there's no real substitute for creation, and for me, consumption gets boring really fast. Like, just taking what other- Yeah … people have done.

Like, at some point I'm just like, "I wanna m- me do it myself," right? I started saying that when I was two years old, and I haven't stopped since. And I gotta say, like, when I think about where I enjoy, you know, where, where I enjoy my time. So you know, obviously, you know, throughout the coup- last couple years we've been talking about m- me building a house. Last December, I took December off to do nothing but build house. Now honestly, that gave me a lot of vibes of working with my dad.

My back hurt. Yep. My knees hurt. Yeah. Like, this is a lot of work. And I'm working 14 hours a day and burning, like, 4,000 calories a day, and I'm like, I am whipped, okay? Now, that was a marathon toward a very specific goal. Yes. However, however, I'd be lying if, if I were to tell you that there wasn't a part of me that would take that over a vacation. Hold on. I watched you several times take that over a vacation.

Yeah. Well, my family was on vacation- Like, like- … while I was doing that, so I literally took that … well, you actually made that trade. Yeah. Yeah. That's not, that's not theoretical. That, that happened. I did. I did. And again, my wife and kids are just awesome, so, like, they understand, like, when Dad's on mission, just let Dad be, let Dad cook- Yeah … right? Yeah. Let, uh, let Dad do his thing.

But, but the other side of it is not a single moment had gone by, other than wanting to spend time with my family, where I was like- Yeah I'd much rather be on a beach right now. Right? I mean, think about that. I'm taking my vacation time, time I should be recharging with and doing the opposite- Yeah … you know, kind of running myself harder, and I'm saying what I want to do is create. And to me, that's a vacation.

Now, now when I say that, I don't expect everybody to feel the same way, not even close. But what I wanna point out is I don't wanna be in a position where I'm not creating. Yeah. Right? Like, I'm not looking for a future where I'm like, "I'd really like to stop doing what I'm good at." Let me put it this way.

I'm 100% confident that if the greatest of all time and really any other player, you know, whether it was, you know, Michael Jordan, Tom Brady, whatever, could play to their 100 Warren Buffett style, they'd absolutely- Yeah be playing to the- to their 100. Tom Brady actually tried it. Yeah. Getting closer. But it's because that's what we're built to do, dude, right? Yeah. Like, why would we wanna stop doing it? Why would we wanna stop doing it? I don't get it.

Yeah. I think we can deny that builder impulse for a little while, especially when we're tired. Yeah. Yeah, yeah. It becomes easier to do. When we're tired, I get that, right? The, the thing is, once that stress is gone, the calling comes back, right? That's what I was saying before. It's like once, once the nervous system resets, we go, "Now what?" Right? Yeah. Like, how do I unretire?

And I think the, the challenge I've seen for a lot of founders is that… A- and look, nothing wrong with an exit. Nothing wrong. They're great. Yeah. Yeah. But I've definitely seen founders who exited and then went on to try to find something else as purposeful as the business they were running, but they were tired running. Not tired of running. Yeah. Tired while running. That's different. Yeah, yeah, yeah. Yep. Very different.

And I think that in some of those cases, they actually would've been far better off just to maintain the business. They didn't need to sell it. They just needed to change their relationship with it in some subtle ways that could've made that easier to do. It just, we just get buried under exhaustion. Let's build on that.

I think retirement, the, what, how founders should think about retirement isn't, "I want to stop working." It's I want to control the outcomes, right? Yeah. I wanna control maybe I don't have any investors anymore, right? That seems to be, honestly- Yeah … be the most popular one, right? Anybody that's taken on investors, that their dream the next time is to not have to take on investors, right? Which is ironic- Yeah … 'cause their dream the first time was to, to get investors.

Yeah. What, what can I do to get an investor in the next time? What can I do to avoid that- Right … at all costs? Maybe it's working with fewer people or closer people or both, right? It's like, "Hey, you know, I, I worked with a ton of people. It was a lot of management and p- and politics and everything else like that. I'd love to work with a smaller team where it's very intimate and, you know, we do our thing." Maybe it's control of your day.

Like, "I liked what I did as a founder, but the job required 14 hours a day and, and I, I don't wanna do that." Well, guess what? Yeah. You don't have to work 14 hours a day. Right. Your point of retirement is to say- Yep … "I want to work four hours," or whatever your number is, right? The point of retirement should be a set of conditions that allows me to do what I love under my terms. Yes. Under my terms.

Yep. That should be the framing of retirement, and we should be very deliberate about it. It should be my dad saying, again, this, he wouldn't have said this, but my dad saying, "Well, I love to build stuff, but I wanna be able to do it on my own time without killing myself. You know, if I'm- Yeah … if I'm in pain or if I'm exhausted the next day, I wanna be able to not go to work," right? Yeah. That makes total sense. I had a- Yep … a contractor on my job last week.

He was 64 years old, and he said, uh, this is why my response will be funny. He said, uh, "I can come next week, but I can only come for six hours," right? Uh-huh. And I was like, "Why?" The gout, Will, the gout. Yeah, yeah, exactly. I was like, "How dare you?" I just, it was such a specific answer- Yeah that I was just curious- Yeah … why he said it. He's like, "Well, I'm retired." And I'm like, "But you're

still working, right?" He's like, "No." He's like, "I still work, but I work a retirement schedule, not my previous schedule." I love it. And I was like, "Hats off to you, brother," right? Yeah. Like, yes, that's the answer, right? Like- Yeah … I'm working on my own terms, right?

Like- That's it. Look, we can't fight the wiring, and I think it's, we find ourselves apologiz- apologizing for the wiring, that we're built this way. This is what we are. We don't have to apologize for the wiring. We don't have to fully change the wiring. Just start designing better circuits, right? Right. To your point, like, how can you make this just work in a way that works better for you? There's plenty of optimization to be had.

I don't think founders, any of us, should be thinking about how do I stop doing what I'm great at? Yeah. I think we should reframe it to say, how do I stop doing what I'm g- or how do I keep doing what I'm great at, but stop doing what I hate? Yeah. Retirement should be about reframing. So I, I don't want us to pretend like, like w- we don't wanna build anymore. I think that's bullshit. This is what we are put on Earth- Yeah … to do, right?

To like, we don't wanna- Yeah … retire from that, right? Retirement shouldn't be about w- what I'm, I'm not doing all those things. It should be about this is what I love to do. I wanna do it forever. Yeah. But I wanna do it forever on my own terms in a way that I love, that when I jump out of bed and I say, "I can't wait to do this," nothing wears me down. Overthinking your startup because you're going it alone? You don't have to, and honestly, you shouldn't.

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