Ryan Rutan: Welcome back to the episode of the Startup Therapy podcast. This is Ryan Ran joined as always by my friend, the founder and CEO of Startups.com, Will Schroeder. So everybody listening, like, imagine waking up tomorrow and realizing that every big goal you'd ever set, personal, financial, your startup, whatever, was already checked off, right? Like victory lap, or is it an identity crisis. Well, I feel like you are either have hit that wall or you're like, you're really close to it. So today I wanna dissect what happens. Like when the scoreboard reads game over, but like you're still itching to play. I mean like imagine for us if we're we're too for a living, we help other people define their goals and and and redefine their goals and keep adding more goals to. I mean, a startup is just a collection of goalposts that we keep trying to kick through and then move to the next one. So like, how the hell do we reconcile this?
Wil Schroter: I tell you what, like I have run out of goals. Now I say. That like I'm probably, you know this, I'm probably busier than I've ever been in my life, right? Like every waking hour is accounted for. So what I'm saying I'm out of goals that that I'm probably not quite representing, but something interesting happened to me in the last year, I would say, in the last year, and it's been wildly like cathartic, reflective, anxiety driving, etc.
Ryan Rutan: Isn't it funny how like, the lack of having something to be anxious about can drive anxiety all by itself.
Wil Schroter: Oh yeah, well, you know this as well. I found plenty of new things to get anxious about. However, however, here, here's what's changed. I want to say at a high level. That I've run out of goals. And, and here's what I mean by that, because it's a weird thing to say, and I am, I am so goal oriented, right, every single day, the first thing that I do when I start my day is I make a checklist of stuff that I want to do for the day. I do it 7 days a week, uh, so I do it on Saturday, Sunday, the first thing I do is I get up and I make a list of all the things I want to check off. Even when I go on vacation. I make a checklist of all the things I want to do while on vacation, like, like read book, do whatever, and I think it's just because I, you know, I like checking stuff off, right? Like, so I, I, I love, love goals, but so I wake up one day and I'm 50 years old, and I'm like, what are my? Next 10 year goal. So you know, like it's great like milestone, you know, part of your life, and I sit down and I try to have this like brainstorm personal whiteboard moment, and I come up with zero. For a guy who makes goals for a living, that's really sad. It's sort of me thinking down this process. How about you?
Ryan Rutan: I don't think I'm quite there yet. I don't think I'm quite there. I don't think I, I haven't done all of the things I wanna do. We're getting ready to execute a new, a new adventure 2 Fridays from actually, by the time you're listening to this, everyone, 4 days from you listening to this, I will be, I will be boarding an airplane on the 4th of July, Independence Day, wasn't intentional, and we're heading off to uh to Madrid. Uh, so there's still some stuff to be done there. Now that's a very personal kind of goal, that's not a business related goal. But here's one that has been giving me a little bit of peace lately. And it's that, while I'm getting closer and closer to having like the really big high level goals that I want completed, but I happen to have these three other little people that live in my house, who now started having some of their own goals, and we're getting to some like really interesting stages, right? Like, my daughter's asking me now about college visits and like what's career look like? And I'm like, right, what's it not look like and so I think that, and look, I know I'm not gonna be as involved in their goals, like they won't want. to be, I won't want to be. But like, there's gonna be some sense of like, how can I enable that? How do I participate? How do I take part in that? Or how do I even just sort of enjoy watching them go through the same struggles that I went through to hit mine? I think that's kind of where I'm at because to your point, like, we've done a lot already. We've gotten some of the things, right? I've had a lot of the experiences. I've had a ton of experiences. I've I've lived all over the world, done a lot of stuff, and, and I've been really happy with it. So like, well, I, I'm kind of in the same boat. Like, I always feel like I need a goal, and yet when I look around at like, OK, what's the one big ass thing that I haven't, I haven't thrown a dart at and hit yet, there isn't one, right? I can do bigger versions of some of the stuff I've already done. I could have more of some of the stuff I've already done, but there are very few things left in life other than learning how to make all of the Othello pieces flip over just by passing my hand over like the commercial promised in 1984. That I haven't done. No,
Wil Schroter: I get it. So it's OK. Let's talk about what were these goals supposed to accomplish, OK? So I wanna zoom out. I wanna zoom out and I wanna say all of us early in our careers early in our lives, some of the folks listening are earlier in their careers. We set up these goals. We have these, these big milestones that we want to accomplish. A lot of times we start a startup to accomplish some of those goals. I, I gotta say early in my life, my goals were super simple. Like my goals were like so basic, Ryan. Like this is, I'm like 1718 years old. I was. Broken hungry. And my goal was this, don't be broken hungry. Don't be broken
Ryan Rutan: hungry. Yeah, reverse my current circumstances.
Wil Schroter: Yeah, yeah. My methodology of what that meant just meant show up at work today, get paid $5 an hour, and eat with that $5 an hour, and I was perfectly fine with that. I, I want to isolate that moment for a second because I think people think entrepreneurs always have big visions of what they wanted to become in the world and like they just, you know, what works so hard to make it happen. Survival. Yeah, not so much. There are many points in in many people's lives where their expectations, and this is a big part, where their expectations are wildly tempered, right? So our goals are often a reflection of our our our expectations, right? Ryan, I'm guessing you don't have a goal to play professional soccer, nor do I have a goal to play professional football. Like they're tempered by what we think our realities are. Now.
Ryan Rutan: Both of both of my knees agree with this decision by.
Wil Schroter: What's wild about what we do for a living though within startups is we know we have the ability to do exponential things, right? Like, we could create the next Shopify or Spotify, right? Like that actually is possible, not likely statistically, but it is possible. Set these goals. Everybody listening right now that building a startup has a goal that's his big honking goal. However, what if you what if you could fast forward to that goal right now and be at that goal? I was sure of you. That life would be dramatically different. This is where it gets wonky, right? This is where
Ryan Rutan: it gets wonky. I mean, we did, we did a full episode on this like kind of like play testing your dreams. Remember we talked about like, well like just if you want, you think you want to retire at 50, play test it for 3 or 4 weeks at 40 and and see if it's really what you want, right? Like we talked about like I wanted to go fishing, moved to Florida. Like I could fish every day. I can't, I can fish 2 days a week maximum. Bought myself a kayak. I was like, I'll bet the next step is a boat. Nope, I loved my kayak. Need more than that. It was perfect, right? So it's like, as you start down these paths sometimes, you realize that like the goal that you set at the beginning, gets recalibrated as you start to achieve the stuff that happens along the way. One of two things happens. You realize I actually don't need that thing, or you realize the effort to get to that next thing is significantly higher than what it took me to get here, and therefore the the ROI on it's not gonna be what I thought. I won't go after it.
Wil Schroter: I've always said for a long time that the value of anything is the fact that you don't have it. Don't have it, yeah, right. Uh, and, and I say that because whenever I didn't have something, I placed so much value on it. And let me give you kind of different dynamics that could play into this. If you're in a really bad relationship, personal relationship with your spouse, then your mind, that relationship being fixed or replacing with another one that, you know, isn't terrible, is gonna make you so much happier and you're gonna be so much a different person. If you don't have money, you have all these, you know, past due bills and woes. Etc. When you have money, you'll be fine. The list goes on and on and on. It creates a trap for us, and this is the part that it took me 30 years to figure out. It creates a trap where we can conveniently believe that if we have something we don't have, that we will be fundamentally different on the other side. What we never get our heads around is, if I have an asshole before money, I'll likely still be an asshole after money. Or you know. Or whatever your thing is, if you were the person that always got in fights in your relationship, when you find your next relationship, you're probably still the person that always gets in fights. You're just now getting in fights with someone else.
Ryan Rutan: Someone else, yep, yep. Well, I haven't had nearly as many fights with this person because we haven't been together for nearly as long.
Wil Schroter: Exactly right. And so I want to start by by talking about how we kind of sensationalize the other side of these goals without having a real good understanding of whether or not getting to. That goal is really gonna change anything. Because in my experience, having gone after a gazillion goals, I would say I'm making this up 10% of the time the goal is worth it, which is shocking, which is.
Ryan Rutan: So I would draw a distinction just I'm curious your thoughts, like the, they're worth it versus what you expected, right? If 10% of the time the goals were worth it, would you say 10% of the time it was exactly what you expected? Like, I got this thing, now I feel this much better about life. That's exactly how I expected it to go.
Wil Schroter: I would say in most cases, in most cases, the joy of accomplishing that goal was so insanely short-lived, comparative to the work it took to get there, that it was like, what the hell, man, and, and again, I think when people consider, you know, I wanna have these big goals, my startup has these big goals, I want, I wanna make my startup huge. Do you? Right? Like, do you actually know that that's gonna work out for you? It usually does not, right, miserable by the time you get there. Where I was most surprised in life, this is, you know, again, all mapping back to goals, was how often I would set goals that I'd work insanely hard to accomplish. I'd get, I'd get the trophy, the thing, whatever it is I was trying to get to. And the amount of value it drove to me was freakishly low. Yeah,
Ryan Rutan: it's your point. The value of something is, is the fact that you don't have it. We were talking to a group of guys a couple weeks ago, talking about like, you know, investments later in life stuff, like what is it, what do you want to amass, what do you want to have? And then, and then somebody posed a question like, well, as you're thinking through that, like, what are the most rapidly depreciating assets? And I jokingly immediately responded, I was like, mine, right? Basically meaning that like once I have it, right, like, and now that's not entirely true, right? If you're talking about purely monetary standpoint, sure own a piece of real estate, whatever, yeah, it has, it has continued value to some degree. But to your point, like the reason we set the goal in the first place, and we set out to accomplish it, the importance of that tends to diminish kind of the minute we, we hit it, and particularly founders as a group. I don't know if there's anybody that's maybe professional athletes or the people like that where it's like the minute I have a Super Bowl ring, the only thing that's gonna make me happy is. The second one, but founders, like the, the second we set a goal, we chase it maniacally, the second we accomplish it, we replace it with another, like
Wil Schroter: that. But the longevity of the benefit is way less than we think it is. Now, now let me give you some examples. So, someone will say, well, if you sold your company for $100 million and you took $20 million off the table, let that $20 million last you forever and longevity is forever, so your argument's bullshit. Not exactly. Yes, numeric. the money is in the bank. I get that. What you're missing when you say that is you think that you are going to be OK. And here's what everybody will say, and I, and I get this argument, except that it winds up being wrong. They say, well, look, I have a bunch of stuff I can't afford right now, right? I can't afford mortgage or to be to buy a house anymore. I can afford, you name it. And when I have money, when startup creates money and I have money, I can buy those things. So you're totally wrong. I don't. have my, I get that. What you're missing is once you've done that, you picture yourself in a headspace in an emotional space, uh, a feeling of, of being fulfilled that rarely ever comes true. And Ryan, you and I talked about this on other podcasts where founders sell their business and they think that all these things are gonna come with the sale of their business. It actually makes it worse, which is really interesting to me.
Ryan Rutan: I sold my business and my identity. I sold my, my business. And all my daily routines. I sold my business and all my friends and the people that I talk to every day, right? Like all of these things went out the door with it, and now you're sitting there with money in the bank and an absolute identity crisis and no idea what to do next, right?
Wil Schroter: And look, I mean, again, if you have the choice between being broke with an identity crisis and rich with an identity crisis, I recommend it easier or rich for sure. You don't give it away. However, what I'm trying to to to get at when we're talking about what our goals were supposed to. To accomplish is that we set these goals with a bit of a false premise. We set these goals with an idea that once I achieve goal, more things will change and more importantly, sustain than I ever thought they would. OK? So let's assume, you know, we can say, hey, OK, maybe that's true. But there's another side of it too, which is once you do accomplish this goal, whatever it is, you get a dopamine hit. Let me give you an example. Back in the 90s, uh, when I was young. So long ago, Jesus. Back in the 90s when I was young, I had this dream, like I think a lot of people did back then and probably whatever the equivalent is now, that one day I would be able to afford a white BMW 3 series. Why was it white? I don't know. It was the 90s it
Ryan Rutan: was the thing. That was that was
Wil Schroter: definitely a BMW 3 and In my mind, because I was driving the biggest piece of shit ever. It was called an Audi 5000, which in its heyday it was actually a beautiful car. I did not own it in its heyday. That thing was so beat up, Ryan, that the entire, uh, exhaust in the bottom was held to the, to the chassis by coat hangers. Yeah, yeah, right, which is the only solution for a short period of time he would melt off as time would go. It was so bad that when I drove it to the dealership to trade it in for a white BMW 3 series that it actually the car shut off. Like I'm just driving and the car just shut off while I'm. Driving it, yeah, not, not dangerous at all. And I coasted into the dealership and parked it, got out and handed them the keys. Like that's
Ryan Rutan: on one hand, you have to, I, I would love to have known what was going through the salesperson's head at that point, because on one hand, they're like, this guy definitely needs a car. And yet and yet, based on how he arrived, is he actually gonna be able to buy one?
Wil Schroter: You bet. And so, so I, I'll never forget this moment of pulling out of the dealership in a white 3 series BMW and Ryan, I was, I was over the moon. I thought I had one at life and everything was gonna be perfect thereafter, OK? And it was for well over 24 hours,
Ryan Rutan: right?
Wil Schroter: We all for 24 hours. I had one
Ryan Rutan: 5 years in the making, yeah, yeah, 48 hours in the enjoying
Wil Schroter: it and that was such a perfect kind of um microcosm of what I would start to learn about goals. Goals are really valuable until you get them, and then on the other side of it, you never quite picture what it's gonna be like. I was talking to a car guy, uh, another founder. Um, actually, we've referenced him before in the podcast, uh, David Hannameier Hansen from Ba. David's like crazy card guy, and I remember like back in the day he had like a $700,000 Pungani or whatever it was. I mean like he's, he's way, way in the he's a massive car collection, whatever. I was talking to him about this and he said, I think the 3. Sears BMW was his first, right, maybe it was a Porsche, the first big purchase, yeah, yeah, yeah. And I remember him saying to me in his Danish accent, he's, I'm not gonna try to replicate it. He's like, Well, buying that, I think, I think it was a Porsche. He's like buying that Porsche gave me 90% of the satisfaction that I would ever get from buying a car. He's like, I tried everything afterward, right? Like, like his car collection is sick. He's like, but it never, nothing ever even came close to the satisfaction of getting that first car. And basically, basically what he's saying, and I felt the same way, is that BMW gave me the 90% of the satisfaction I'd ever get from getting to that goal because I was going, you know, from nothing to something. And ever since then, myself, I've probably bought 20 exotic cars since then and nothing even gave me 10%, the value of the satisfaction
Ryan Rutan: because the. of dopamine becomes significantly smaller, the increment of cost to go up to those higher levels becomes significantly higher, right? You're paying more and more money to receive less and less joy, whatever outcome that you wanted.
Wil Schroter: But there's another side, yes, 100%, but Ryan, there's another side of it. This is, this is what messed with me and has messed with me ever since, and it's probably what's been messing with me in the last year. I now know that what that, like what that next level is. Right, like, I think a year or two later I went out and I bought like a a Lamborghini, and I was like, oh my God, like it doesn't get better than this, and it was awesome for like 24 hours. And then I realized that the the amount of time, effort, cost, whatever you attach to increasing the goal, didn't have anywhere near the payoff, and here's here's what's interesting, which made me not want to do it. Right? It's kind of like Tom Brady saying, hey, I've got 8 Super Bowl rings, like after the first one, just none of them really brought me anything. I just kept doing it cause I thought that's what Tom Brady does. I don't really want to do this anymore cause it's it's killing my body, right? I, I don't need the money, right, blah blah blah. I think something interesting happens when you accomplish some of these goals, and you realize that the value of going back and setting more. Doesn't have a payoff. I think that messes with you.
Ryan Rutan: It does, it does. I mean, like, and it's an interesting and dangerous curve to be on, right? Because depending on when it happens, like, so what we're like, yeah, you know, actually hitting 100,000 in MRR for the business probably won't bring you that much more joy. Fuck it. I'm just not gonna, I'm not gonna move, and look, that might be absolutely fine. I think it depends on what you set out to accomplish, why, you know, do you have investors, do you have a big team that's all all expecting you to do these things? Did you make those promises? If you didn't, then I think it's OK to reconsider these things, but it is interesting because I think that like early on, I think there were some important milestones that kind of needed to be hit. You, you talked about a little bit. It was kind of like the ones that are, you know, safety or or survival more so than just I want a thing, and so I think that there are a number of those. that once you've accomplished them, there is probably a longer lasting effect than we give credit to. Like some of my early goals on accomplishing them did 3 things for me. OK. One, they gave me the immediate whatever it was, right? So like sold the first company, got cash, right. Cool. Got cash. Now the cash doesn't last forever. Dopamine hit of achieving that thing of, of, you know, building a business that doesn't last, whatever. What did last was a bit of a safety net that. Came from that, right, which allowed me to make different decisions going forward. That that did last to some degree. The only thing that lasted was the memory that I could do that, right? And that that was an asset that I definitely carried forward. It's like once you've accomplished something, you know, you're capable of it, it sets a new save point for you, and you can kind of continue to build up from there. So I think that's one that we, we lose. But I also didn't need to sell 5 companies to know that I could do that, right? 1 was enough.
Wil Schroter: Well, let's let's build on that a little bit because I think there's some important points in there. The first thing I want to point out is that there are, I see two different goal paths, if you will, for, for everyone. One is what I consider the pleasure and lavish path when people are like, oh, he buys a $100,000 BMW kind of thing, right? Like that's just, you know, pure pleasure. But the other path is around pain, the avoidance of pain, OK? Can't pay my bills, can't make, you know, do a doctor visit, you know, things like can't feed my family kind of it's, it's eat
Ryan Rutan: and eat caviar, right?
Wil Schroter: Uh, and so I think initially, most of us are just trying to avoid pain. And, and the truth is, for most of the world, pain is the baseline. There, there's a significant amount of pain and and relieving that pain vis a vis security is our number one goal, and that is an incredibly important goal, no question about it. However, for those folks, let's talk again, founders, that's our world, for those folks that achieve it, initially, they are so distracted by that pain that They just assume that when that pain goes away, that they will be happy and satisfied in all these things. Here's what's really interesting. That rarely happens. It rarely happens. The difference is they just don't, they just aren't focused on pain. Let me give you just a different take on that.
Ryan Rutan: We, we create new pain that we then feel like we have to go solve.
Wil Schroter: I've watched this over and over, particularly with founders, right, because we're so used to commanding our destinies. And so it throws us when we command our destinies, get what we want. And then don't have the results we expected this podcast. And so one of the interesting things I found is that when you are in pain, I'm now I'm gonna use physical actual pain, right? You've hurt something. You've had a chronic condition, I've had a chronic condition that is egregious amounts of pain. At the time, all you want to do is get rid of pain, but something happens where you do, right? You and I both gone through, you know, significant health struggles and and we've we've found a point where we got on the other side of it. Once you've removed pain, It doesn't necessarily make you happy, it just makes you relieved that you don't have pain. It's different, right? People think like, oh, I'm in a bad relationship with my spouse, and so if if we just break up or, you know, settle or whatever, then all of a sudden I'll be happy. No, you just won't have pain. It's not the same as you'll be happy.
Ryan Rutan: It's the difference between running from something and running towards something.
Wil Schroter: Correct. And so a lot of our goals are about relieving pain initially, and I would argue that like phenomenal goal. Once you've relieved pain, right? And now you're just looking at it strictly from the standpoint of, of how do I increase pleasure, happiness, you know, uh, whatever you call it, that's where it starts to get a little gnarly, because it's actually way harder to do than people think. A lot of people think if I have more money, I'll just be able to have more free time, be able to to go on more vacations, etc. It doesn't work like that. You know, something that's really funny about everything we talk about here is that none of it. is new. Everything you're dealing with right now has been done 1000 times before you, which means the answer already exists, you may just not know it, but that's OK. That's kind of what we're here to do. We talk about this stuff on the show, but we actually solve these problems all day long at groups.startups.com. So if any of this sounds familiar, stop guessing about what to do. Let us just give you the answers to the test and be done with it.
Ryan Rutan: No money, no problem. Man, we've all heard it. It's true to a large degree. You know, I think that there's there's something interesting here, which is as you're as you're talking through this, I started to think about it in just slightly different terms and came to a realization that at both ends of the spectrum, right, whether we're talking these like early goals or later goals, there's an existential component to both, at least in my case. Yeah, yeah. The the first goals were like, get to that safety baseline, right? Existential in the sense of like, how do I continue. How do I, how do I, how do I survive? And then the later goals became more around why am I here, right? Existential on a very different level, right? But what was crazy was like, I don't really remember there being a transition point between those like, ergo, I didn't understand. I'm now safe. I can now just focus on these kind of like more cerebral things. I can, I can be more focused on the the why. And I guess one of the big questions is like some point why are we still chasing, which I, we've we've answered in a lot of different ways. Today and we've talked about other podcasts, but I think that was an interesting realization for me is that they were both existential just at kind of different ends of that spectrum, and I'm not really sure how I'm going to reconcile this now. Can't land
Wil Schroter: this
Ryan Rutan: plane,
Wil Schroter: Will. Let me build on this a little bit. So one, we have again, we're trying to get rid of pain, right? In, in, in whatever forms that affects us. And let's say we do that, uh, we get, we get rid of pain. The absence of pain is not pleasure. It's just the absence of pain, right? And. I think that's a, that's a when you're in pain, like literally you and I have been quite physically, all you give a shit about, you're like, God pleasure, I don't care. I don't want to be in pain.
Ryan Rutan: Just get me back to it's a neutral. I'll be fine. I'll be great.
Wil Schroter: You bet. But for folks, you know, let's take this back to, you know, career startup, etc. for founders who were like, hey, if I become super successful, then I'll be happier. That is a giant myth. Now, you will have the absence of pain, but that is not the same as happiness. And that's what really messes with us, OK? But let me zoom out a little bit further. The idea is that once we hit whatever those milestones are, let's let's say we've already made it past the video game level that is getting out of pain, right? And now we're just trying to maximize for pleasure, enjoyment, happiness, fulfillment, etc. Those milestones, those goals, if you will, are really hard to come by, really hard to come by. And one of the tricky things about them is that you can quickly realize that more effort actually doesn't buy you anything. Let let me build on that. Hence, hence where I'm at right now in life, OK? Right now, buying another car, I already know is not gonna give me any more fulfillment, right? As you know, I drive a pickup truck and, and I tend to, what's in the shop, but yes, but like buying another car isn't gonna do that. More vacations isn't going to make me more happy, right? For me, building things like creating things makes me happy, but one of the things that's really messed with me, Ryan, over the past year or two, is for the first time in my life, it's like I know better that yes, I can put myself on some ridiculous goal, and it kind of sucks to know that I already know it's not gonna work.
Ryan Rutan: Yeah. Look, I think there's this sense that as we go from feed me to fulfill me, that it becomes significantly more difficult. Right, like we're climbing this, the pyramid of Maslow's hierarchy of needs and like we get to self-actualization, which is where you're at, and then all of a sudden we realize like, someone's kind of fucking flat, right? And um the view from here is basically the same as I think, you know, for me, as we're talking through this, I'm realizing that in some of my most successful goals, and I don't mean that in terms of the size of the outcome of anything else, I was as satisfied. By the chase of the goal, right? So the accomplishment was satisfactory, but I, I need to go back and kind of do some calculus on what was it that made me engaged throughout the process, right? So I wasn't simply doing it because of the endpoint, but like truly like the the the entire pathway was something that I wanted to be able to do. I go back to things like coaching Hannah's first soccer team. We won the league that year by leaps and bounds, but that's not the part that was like the coolest for me. Coolest part for me was like the individual little moments of like that kid that had never scored a goal that nobody ever thought was gonna score a goal, who never scored a goal, but we made her into a great goalie. Just kidding. No, she, she scored a goal, right, so it's like, what are these things along the way, right? Can we find fulfillment in and of course we've all heard this, right? You gotta, you have to enjoy the journey, not the destination. Sure,
Wil Schroter: you know that,
Ryan Rutan: yes,
Wil Schroter: rich people, rich people say dumb shit like that, that you need to enjoy the journey, not the destination, and Let me, let me expand on that. As an aside, I'm gonna tangent for a half second. I can't stand when rich people give rich people advice, um, right, like these platitudes, because I'm like, I always put an asterisk at the end of their quote that says, if you're rich,
Ryan Rutan: if you're rich, yeah, exactly, you can just hear it, right? Come out, comes out in the expression they make after they finish. It's the smug look says if you're rich. Yeah.
Wil Schroter: Yeah, and then it's like, hey, great advice from you. rich guy because that now applies to you, right? Like money isn't everything if you're rich, if you have it like you already have it, yeah, um, try not having it. I never felt that way, right? But, but my, but what I was gonna say is what's been interesting to me about, you know, kind of chase the journey, enjoy the journey, etc. it is true, but I would say this a bit different. The journey is very different if you already know you've won. So in other words, uh.
Ryan Rutan: In which direction? How do you mean for better or for worse there?
Wil Schroter: Oh, well, I mean, there's the question. I'll leave it like this, um, when someone says you should really enjoy the journey, dude, when I didn't know if I was gonna be able to eat at the end of the week, there's no part of me that was like,
Ryan Rutan: I'm not talking about the existential I'm not talking about the feed me side. I'm, I'm, I'm saying we're, we, you said we were past we were past the that
Wil Schroter: that's when you've already won. if you're optimized. for pleasure, right? If you're saying, uh, you know, I want to go from a $100,000 car to quarter million dollar car, then you can say dumb shit like enjoy the journey, right, because you've already won,
Ryan Rutan: right? You're already driving the white BMW right? the rides already fine.
Wil Schroter: Like I just, my frustration and I try to be mindful of this coming out of my mouth as well, is saying using platitudes like enjoy the journey with like almost like complete like. Disassociation from what people in the journey are actually
Ryan Rutan: their experience, they're like, enjoy the journey of not making payroll again this week, which part of that is fun, logging into gusto and seeing the negative battle like what, which part of it, right? Like who I'm gonna let go, letting them know, hey, look, yeah, I know you got fired today, but don't worry about the outcome of being fired. Enjoy the journey, by which I mean pack up your desk and. Yeah.
Wil Schroter: I think about it in terms of you mentioning soccer, right? I think there is a point where you realize that winning at soccer isn't going to really change your outcome, but playing soccer is going to be awesome. I've been trying to change that mentality that like it it's a luxury to have, if I'm being honest, to be able to say if we grow startups.com to 100x what it is now. Sell it for a gazillion dollars, it literally won't change my life. And that's not because I'm so incredibly rich. It's because I just don't actually need anything else, right? Like I just financially, like there's, there's nothing that I want that requires so much cash that I have to do something extraordinary to get it. Now that's not the same as saying that like my ambition is gone, just magically disappeared. It's saying that for the first time in my life, there's not a a a material object on the other side of it, which is weird for me.
Ryan Rutan: It is, I think part of it is just saying like, look, I don't have to have because There's nothing that I'm being ambitious towards. Doesn't mean that I'm not still driven in some way, but it doesn't necessarily have to be that same ambition. I think it's trying to swap fuel sources in the middle of a drive. And it's like, how do I say like, look, I don't have to be scared anymore. I don't have to run towards things, and there's nothing that I really want so bad, but for some reason, maybe this is the big question we need to ask ourselves, but for some reason, I still feel like I need to want something. I, I need to want to at least look useful. I wanna be in motion. I want to Be productive. I want those things, but those things untethered from a specific goal are hard to achieve. And so I think this is why we come back full circle and go, so I guess I need a goal.
Wil Schroter: So here, here's what I've been kind of discovering, if you will. Um, I've been discovering that for me for the first time in my life, attaching my effort to a trophy doesn't buy me anything. It's a weird thing to say, right? It's a weird thing to say. But for example, I do not want a private jet. Now, I say that to say private jets are wild. Expensive, right? Like, no matter how you do it, no matter how you cut it, they're wildly expensive. And for people who have, you know, great wealth or want to achieve great wealth, a private jet is like part and parcel to what they want. I've ridden on private jets. They terrify me. They're too small, and my wife won't get on one. Now I'm saying that to say it's not like we're riding private jets all the time and my wife has these decisions to make. She's been on a few and she's like never gonna do it again. Point is, it's one of the biggest like financial achievements yet, and I actually just don't want it. Yeah. So stick with that. I don't want a second house. We did a 2nd house for a decade. It sucked. Always felt like we had to be at the other house. It was awful. I, I'm grateful, wildly grateful that I had that experience, but now having had it, I also know I don't need it. And again, going back to the cars and everything else. I am shocked at this point in my life, actually truly shocked, Brian, how much I don't want. Now, I say this in a backdrop, you know, of building my dream home, which is, you know, a, a, a huge thing for me. But what was most interesting about, you know, building a home and, you know, as involved as I've been. Is it feels like the last thing I've ever wanted, and that that makes me a little bit sad.
Ryan Rutan: I was gonna say, yeah, that that that's probably gonna drive anxiety in and of itself, right? It's like the sense that you're getting closer to achieving that thing, right, which has taken well, decades on one hand, but just even since the, the point of starting, right? It's been a 5 year process. I remember the first time we were talking about this because you're looking at the land, you're starting to do the 3 year renderings, all that stuff. It's been a long time ago, half a decade ago, but now it's like as you're nearing the the, the completion of that milestone, right, the achievement of this one without a next quest feels a bit like idling and neutral, right? Like engine reven nowhere to roll, like we're not good at this.
Wil Schroter: Yeah, well that's a right, that's a great way to put it. Like I wasn't built for not achieving goals, and yet at the same time I'm in a place where I know that just creating more goals for the sake of creating more goals is kind of a bullshit exercise. So kind of what I'm saying is I'm Trying to learn to do the things that I enjoy, not because I get a trophy, but because I really enjoy doing them. I'll give you an example. Wait a minute,
Ryan Rutan: are you back to enjoying the journey, Will?
Wil Schroter: No, no, I'm not gonna enjoy the journey. No, I'm kidding. Like, for example, I play, you know, hockey with buddies, you've been, but
Ryan Rutan: that's actually a great point cause like at some point, like, playing another game of hockey isn't isn't a journey, cause it's not going anywhere. It's just another game and that's OK.
Wil Schroter: We had some uh guys that I was on the job site with we were building our house uh last week. And they were basically saying, um, aren't you really excited, you know, when this house is gonna be done, we're supposed to be done in a few months. And I said, well, one, it'll never actually be done because I'll be working on this thing forever. But number 2, I said the whole point of doing this was to build it, to actually physically learn how to build things, learn how to build cabinets, learn how to do architecture, learn how to do all these things myself and having a big honking like wildly overwhelming goal, which is the nature of what we do as founders, and knowing that I could like. on myself to build it with my bare hands, right? I mean, I think, and, and I don't want to be sexist here, but like as a dude, like provide shelter for family, like, like something you're near and dear to who, you know, my identity.
Ryan Rutan: I'll be there to make the fire the day you open the place. Well I'll handle that side of caveman style.
Wil Schroter: So no, but but my point is, I think what's been interesting about it is that the folks I was talking to last week were like, hey, if this house. We're already built, would it have been worth buying? And I said, absolutely not. I said, we're not building this because we need a house. We already have a house and and we love our house. We're building it because I wanted to create something from scratch that felt like a penultimate moment in my life, kind of like, like a, here's a great way to say it, as it felt like the result of 30 years of effort. It's a trophy, right? It it's it's it's a trophy and it's, it's got a very like cathartic. Milestone, know what it is, right. It's something that says, hey dude, mission accomplished, you're good. And I haven't had a mission accomplished, you're good in 31 years in my career.
Ryan Rutan: I now we're we're definitely gonna be a follow-up episode on this, uh, once, once you wake up and jammies in that house, and we have to go, OK, so did the dopamine last more than more than 48 hours, right? Or now that you've got it, it won't, right? We, we sort of know it won't. But
Wil Schroter: let's stick with that because then again in in. If folks are listening to that, you know, I'm, I'm trying to be open about my feelings and my thought process so you can kind of just see what's in my head. I already know that like, hey, you know, once you get the keys to the 3 series BMW and you drive it off the lot, the, the value, you know, uh, not just financially but emotionally plummets. It's not that. It's knowing that I'm not going to need a bigger house, right? Um, and if I do, I would love to find out what the use case for that one is.
Ryan Rutan: Will has been banned from driving in all 50 states, so he had to build a house big enough that he can drive around inside. So
Wil Schroter: that's kind of off the table. So differently too, like, you know, my kids will leave the house presumably like within the next 10 years, and I literally would have no, no need for a bigger house. My point is, I kind of know this is as much houses we'll ever need. And with that, there's a great calming feeling. to that, like a finality to it, right? Like, like feeling like you've, you've gotten to the end of an important journey, but also, here's what's interesting. I also don't have any expenses after this. In other words, I don't want a boat. I don't want a second house. I don't want a jet. I don't like, I, all the things that people buy with a bunch of money, I don't want any of that stuff like my. My big purchases right now have to do with attachments to my skid steer.
Ryan Rutan: I was getting ready to say like it's, it's another attachment for the uh for the bobcat, yeah,
Wil Schroter: yeah, yeah. And and I guess what I'm saying is, as, as, as folks are thinking through their careers, their progressions as founders, we rarely think about what is the end game look like? It's part of the the of a measure of success if you will, the lack of needing more things. Right now you could get real Buddhists and say we should never. Need them to begin with, but, but that's not my point. But
Ryan Rutan: yeah, no, I think it is. I think it is, and I think then it, it goes from being like we go from playing like really big games with really big trophies to micro games or infinite games, right? I think that's kind of where like, it's it's funny, like as I've been really unpacking the decision to move to Madrid, like for me, like we've got a lot of reasons for the kids, the family overall, like there's a lot of reasons we want to do this, as I've been looking at the ones where like you get to those points where you're like, you've justified a lots of other ways, but you're like, OK, but why am I Actually, really cause I, I've had to push hard to make this happen, right? And so why, why am I actually doing this? And I think part of that was that I feel like it will help me with some of those infinite games, because at some point I mean like this this is like why a lot of people turn to philanthropy at some point, right? They're like, well, I have all the stuff I need, so now I'm, I'm just going to become a uh a philanthropist. I almost said philanderer. That was not what I meant. I, I literally almost said philanderer. Uh, so, and, and what do I mean by like the infinite games? So it's it's things like Mentorship or creative crafts, legacy projects, like continuing to play to play soccer, like there is there's an end point for that, right? There there is definitely a point at which I can no longer continue that pursuit because my body just simply won't keep up with it. But until then, right, that's that's one of those things, but like, those don't necessarily have the same kind of outcome, right? Like a mentorship, for example, right? There there will always be someone new to mentor or the the the mentee will always have elevated goal like they'll be in the same situation like well it'll help them accomplish their goals. But like for you, for the house, you've said this before, it's like you're gonna spend, you know, it took you 50 years to build it, and you're gonna spend the next 50 like tinkering with it and and adding on to it and doing all this stuff around it, right? So I think to me that's kind of what it turns into, it becomes the infinite games where we specifically design them so that there is no endpoint, so we can just keep playing.
Wil Schroter: OK, so, so stick with that for a second. They just keep playing. I always use Tom Brady as an example because he just to me, he just seems like such like a pentultimate success story. Again, I don't know the. Yeah, he might be a giant ass, but the point is, there's a version in this where Tom Brady is like, you know what, I've, I've won Super Bowls. I, I get it. Yes, I'm capable of winning a Super Bowl, but you know, I just like passing the ball around in the backyard to my kid or with my friends, and I just enjoy the game of playing football. I don't need to win Super Bowls to do it. I just want to enjoy what it is. Ryan, it's how I feel about our jobs at startups.com. Startups.com becomes a 100 times bigger. I honestly don't don't know that it changes our lives whatsoever.
Ryan Rutan: To a large degree, I hope it wouldn't, right? I love what we do. I wanna keep, I wanna keep doing it, like, to the extent that if it became 100 times larger and it meant that we didn't get to do some of the things that we do now, I would not want that, in fact.
Wil Schroter: We're not going out of our way to keep it small either, right? The point is, we're at a point where we already get to do the things that we enjoy the most. Would that improve a few things in the future? Of course it would. But the idea being we're enjoying what we get to now, but this is, this is the equivalent of us as Tom Brady in the backyard just throwing the ball around. Because we actually enjoy it. If I were to think about an evolution of goals, right, my thought is this, ideally, everyone listening achieves all of their goals. I sincerely hope that happens. And when it does, and when you get to that point where you've achieved so many things in life that you've wanted to achieve, I hope you get to the point that I know I'm working on, working through right now and and right, you know, I'd like to believe you are too, that at some point you say my goal is to be able to do the things I love without consequence, without goal. something that prevents me from not doing it. We're not doing it for the wrong reasons, not doing it because I get a car at the end of it. Doing it because I just love being covered in sawdust, building something that never existed before, or spending time with someone that I love while I'm doing it, and being able to just create for the sake of creating. I think, yes, we might run out of goals, but we'll never run out of the passion that gets us to our goals, and I think that kind of passion is what we need to develop, if we're gonna be able to do this pretty much forever.
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.