Ryan Rutan: Welcome back to another 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. Will we get to this point where we cash in life's chips, and then we wonder, did we buy the right prize, right? Now, we've done this story before. I'm gonna ask you to retell a story. I want you to go back to the moment in time. You and Sarah in Beverly Hills, looking at Bel Air, about to buy a really expensive house, just walk us through again, cause we're gonna play around with this in a different context today around will the payoffs be worth it. We've talked about are the sacrifices worth it, but will the sacrifice be worth the payout today as we're gonna talk about. So I want you to take us back to that moment where you're wrestling with the thought that like, I did all this stuff to get to this moment so that I could make this decision, and then luckily your your your wife stepped in. Yeah.
Wil Schroter: Usually all my life, my my best of moments, uh, finished with, and then luckily my wife stepped in. Oh, you know, it's funny, yesterday I was at dinner with one of our founder members from Startups.com, uh, that I met through Startups.com, which is really cool, and we're at dinner and he hands me a t-shirt, and uh it's a t-shirt he had made for me, and it says, well, this seems like a terrible idea. What time? That's the tagline to my life. Jesus, uh, yes, that's fantastic. Yeah, it was, it was a really cool gift and it's so appropriate for this. So we're going back a few years now, and right now I don't think that that was 6 years ago, like,
Ryan Rutan: yeah, I was thinking about this too because that until you said that, that felt like very recent history, but that was. 6 years ago.
Wil Schroter: So, OK, we're we're going back 6 years. My family and I had just moved a few years prior to that to Los Angeles. We ended up finding a house in Beverly Hills and everyone was like, oh, that's so fufu, you know, bougie guys going to Beverly Hills. It was like our last choice, it just happened to be where we find a house. But anyway, so we lived there for a few years, we quickly outgrew the house cause it was tiny, and, you know, my son Will had just been born and we needed more room. So we go looking for another house. Uh, my daughter had started school in Beverly Hills. She, she loved it, and we wanted to stay in that school district. So we ended up finding a house that was like 10 minutes away, which if you don't know your LA geography, uh, Beverly Hills and Bel Air are just two tiny towns more or less adjacent to each other. That's where we find a house. And I say this and it's not like big time it being Bel Air, literally do that just happens to be where we found a house. Um, I wasn't trying to be the Fresh Prince of Bel-Air,
Ryan Rutan: so anyway, I mean,
Wil Schroter: maybe, yeah, I mean it wouldn't be the worst outcome. We get to the finish line with this house, we go through, you know, the negotiations and everything, and it's it's a big purchase. Right when we're on the goal line. Sarah and I had uh been on a a a quick vacation, like a weekend vacation, and uh we're sitting at dinner on vacation in Mexico. Sarah's like kind of sitting there going, you know, this is probably a bad idea. Because as you know, she's the conservative one, she's everything for her is this is a bad idea, and everything for me is this seems like a terrible idea, what time, what time, yeah,
Ryan Rutan: I agree it's a bad idea, but we're gonna do yeah,
Wil Schroter: exactly, yeah, that, that's literally my job description. Here's what I told her. I said, if we balk on this, this is actually a big problem for me. And I said, you've got to understand, like I've been working my entire life sacrificing and risking nonstop. I can't begin to tell you how many sacrifices I made to get here, and she's been through many of them, so she's aware. Like for the 1st 6 years of. My career, I didn't see my family or celebrate a holiday. Like I never came home for Christmas. I remember I went to other people's house for Christmas because my family was too far away to make the travel and I had to be able to come back in time. And so those are pretty significant sacrifices that you don't get back. You and I, you and I talked about it, we're like, I don't remember college. I know I was there, but I just worked through college.
Ryan Rutan: I remember, I remember being in classrooms. I remember being in big office buildings and and and selling, uh, you know, enterprise level client stuff. I don't remember, like, you know, I learned to play beer pong when I was like. 30 in Cyprus.
Wil Schroter: Like I, I've never been arrested development. I've never hung out on the quad, so to speak, like college just happened to be an address that I had while I was working, OK? I, I'm sure it's nonstop sacrifice and then so many things that come with it with building your own company and the sacrifice. the things that every single person listening to this inherently understands, OK? So when you make all those sacrifices, we make them with the expectation that there will be a payout. Every time I feel like it's a little promise that you make to yourself, when you make that sacrifice, that it's OK, because I'll pay it back later. It's OK because I'll get more later, but we don't actually know if that's
Ryan Rutan: true. We don't, we treat, we treat sacrifice like it's a savings account, right? But we never check the balance or the terms like so. When do I get to withdraw it? Never, never, right? It doesn't work that way. I think that, yeah, well there's no interest, said this before on the podcast, I must say it again, there is no interest earned on happiness deferred or life deferred. It doesn't come back tenfold later just because you gave it up now. Sometimes it does, right? You might get a big pat at the end, you might. But it's not like a guarantee. There's there's no just automatic compounding.
Wil Schroter: And this one isn't this this episode isn't so much I think about the sacrifice as it is for the payout. Let's assume the sacrifice was significant. The question in this episode is, is there a payout that could match the sacrifice? Sure, and I think there's an assumption that there is. So here's what happened to me in this case. So, uh, we're sitting there, and my whole thing was like, look, if I don't cash these chips in now. This was the moment, like there was clearly this was the moment where it was gonna be the biggest purchase of our lives. It was, you know, this, this beautiful house in in Bel Air, like it was, it was exactly what you dream of being able to do if you make those sacrifices, if you take those risks, right? So this was clearly the moment to me.
Ryan Rutan: It was something extraordinary that put the extraordinary sacrifice into some level of balance. To the extent that we can quantify either.
Wil Schroter: As soon as you said that, Ryan, I just thought of something else. It made me think about it. I gotta say up until that point, and not that I never thought about it. Oh, you know what is, I never quantified the sacrifice before. The
Ryan Rutan: quantification, that's the, that's the challenge, right?
Wil Schroter: If I started just brainstorming and I were to say, here are all the major things that I missed that I will never get back my twenties, etc. if I was gonna make that sacrifice, if I was gonna make that investment. This is the time to to to pay it out. So then the question was, was it worth it? And what uh Sarah ends up saying she's like, it's not. She's like, this is a huge rip off, right? You know, relative to what we're paying and what we're getting, it's ridiculous. And I was like, yeah, but if, if I don't cash my chips in, like, this is a huge problem for me. And she says to me, says, you know what, the whole point of that wasn't that you have to cash your chips in now, it's that you had chips to cash in it all. Yeah. So you don't have to cash them in now, find another way to cash them in. And based on that argument, we both agreed right there. Fuck it, we're out and we moved back to Columbus a week later. So I mean like as quickly as we tried to get into that decision, we looked at it and we said, you know what, different direction and we build and we moved back to
Ryan Rutan: Ohio. Yeah, and you know what, 6 years later, I have never heard you say not a single time. A single thing about, oh, you know what, I miss our ability to do this, or I miss when I, whatever, right? Like I miss running past all 12 of Channing Tatum's abs, uh, on my morning jog, right, or whatever the hell it was. I I haven't heard you say it not a once.
Wil Schroter: I don't, well, I'm sure my wife does, but I feel very differently about his abs.
Ryan Rutan: I heard he's down to a 10 pack now though,
Wil Schroter: yeah, exactly, exactly, but what was interesting for me is I was forced to confront. Whether or not this sacrifice that we all take on aligned with the payout. And I think what's interesting is, is that for many of us, the sacrifice comes natural, but we don't really always know how this payout's going to work, right? Right, when you look back and you look, uh, actually, you know, let me ask you this. Recently, you just moved to Madrid, you guys just went to Valencia as a family. Was there a moment where you're like, this is extraordinary, right? Like it does, yeah, holy cow, I'm here. Yeah, and then we're we're here on the sacrifice to get there. Yes,
Ryan Rutan: and you reflect on the sacrifice and you go, this was worth it. This feels in balance. I think there's there's something extremely important in all of that, which is that like I didn't buy Valencia, I just experienced it, right? because I think to some degree we do end up like aligning because we don't, we don't define extraordinary well. Like we had an extraordinary time in Valencia. It was amazing. A couple days at the beach, couple days at the museums, like really, really just had a great time. Uh, with the family, but we don't clearly define extraordinary in in a lot of cases, and then the default just becomes more and more is never enough, and I think we get to this point where it's like, you know, big purchase equals big purpose, right? So this is, I have to do this in a in a one-off. I have to balance the scales. The scales of sacrifice are completely tipped to the floor. I've got, I gotta do something to balance this out. I think that what I'm finding over time is that Instead of looking for that singular payout, I'm treating it more like a line of equity, or I can just constantly make daily withdrawals and just draw down and just enjoy and do the things. And I get it though, like when you were sitting there at that dinner in Mexico, thinking about the Bel Air house. You weren't defending a decision around the house, you were defending the meaning of 30 years of work.
Wil Schroter: Let's build on that, cause again, in this episode we're talking about the payout. What if up until that point, I had just assumed that was the payout? You know, maybe, maybe my vision of it wasn't quite that crystal clear that it was exactly the street in Bel Air, you know, kind of thing, but that was a very visceral like feeling to be walking into this beautiful house in Bel Air and be able to say I can afford this. Like I came from a place where there's no way I I I couldn't have afforded to rent out the driveway, and, and get to a point where I'm like, OK, it's a lot of money, but but but I could make this happen. But then part of me was like, OK, I made all those sacrifices so I could be able to say that. But was this really what I had in mind? Was this specifically it? And it turned out, and again this this is we'll get to this later, it wasn't it, and that that terrified me more. Because for a while I was like, well, what just happened?
Ryan Rutan: I think part part of the what we we end up going through is that we look for these things that will be obvious signals that that there was a return, right? That again, people have seen the sacrifices or maybe not, but we've done the sacrifices and so we want the world to know that it was worth it, and so we did something. And so I think oftentimes. Some of the decisions I've come close to making, or like things that would have been a good signal to everybody else, instead of what I wanted, right? That it was really geared towards, it's like, this will be a good signal that I did well, right? This big purchase will will signal that yes, I did it to everybody else, but then I looked at it and went like, But do I actually care about that? Do I actually want that? And in your case, like, thank God you didn't buy that house, right?
Wil Schroter: It's interesting to me because we all put in the sacrifice, right? Again, we all understand the sacrifice. What we never can quantify is what's the rate of pay for that sacrifice. Sure, sure, the rate of pay is directly proportionate to what you think your payout's going to be, OK? So in other words, if it's like I'm gonna sacrifice, you know, a crazy amount of time so I can buy a $10 million house in Bel Air, then there's some rate of pay of sacrifice that like that aligns there. But if you have no idea what that outcome is. You then also have no idea what your rate of pay is, and I'm not saying it has to be that proportionate, but I'm saying when you have no outcome, right, you, you like, or it's just too amorphous. Like you can't define the outcome. You're like, I just want things to be better. You're screwed, because then your rate of pay could be literally anything. And the, the example I use is like, imagine you've got your first job, right? And you know, whatever your crappy first job is, you're bagging groceries, your, you know, uh mowing lawns, you know, shoveling driveways, whatever. And after your first two weeks, your boss comes to you and says, thanks for everything, here's 28 cents. And you're like, what the hell? I just worked nonstop. I sweated like crazy for 2 weeks, and that was my rate of pay. That's essentially what happens. When you don't have a payout, that aligns with the sacrifice.
Ryan Rutan: So I was gonna say like I think that's the the challenge around having those big goals, and I think the other thing that ends up doing that is that we make the sacrifices across such a long period of time. Yeah, and most of them are absolutely meaningful. But they're very justifiable in a moment, yeah, because that does get paid out, right? That those are absolutely paid day by day by day by day by day. You don't write a big sacrifice check at the beginning and then earn the payout. You, you pay as you go consistently. And again, when you don't have, when you got that that big blurry goal out there, and like, let's let's dig into this for a second, cause like, what's the most common like vague or blurry goal that that you hear? Freedom, impact, time, like, what are you hearing from other founders?
Wil Schroter: Well, OK, you know, it's funny you say cause as you were talking I was like you were talking about what your payout was, you know, throughout this. And I was thinking, your payout, you're being a lot of people's mind included, was the freedom to go to Valencia, was the, the freedom, all of which you've earned, right? You know, which is the point of the sacrifice, the freedom to to do a job that you enjoy, you know, versus having to take a job that you hate. All of these things are incredible payouts. They don't all involve a giant house, right, or a private jet, but they're incredible payouts, a peace of mind, pride of work. I mean, there's there's a really long list of somewhat intangibles, but take them away, there's no value to it, right? In other words, it's it's so so important. For me, I always used to say the same thing. If you paid me 10 times more than I make right now, but you say the only caveat is you now have a boss. Not interested. There's literally nothing I could buy, not because I'm so wealthy, I'm not, but there's nothing you could buy for 10 times more for me, that would outweigh having to answer to someone. It's kind of just that simple. I value that freedom as a tremendous part of the sacrifice in the payout.
Ryan Rutan: Yeah, I think that once you understand how to use it, it's one of those when I hear that, and I do, I get it. I totally understand it, but I think that there's there's a challenge around some of those as well, because when the goal is oforphous, then Again, like you don't know what your rate of pay is, right? If, if you're saying like, I'll get paid, you don't know how much or freedom of what sort, right, and with what are the restrictions. So I think it's just, it's super important to just have some kind of a goal I mean or or or maybe not, right? And maybe maybe that is the other side it's like, because I think if you had picked, because we see that happen too, right? And we've we've done an entire episode on like play testing some of your dreams, right, which you did in LA, which I did in Florida, and we, we, we come to find out like. Retirement is definitely not what we're aiming for, right? That isn't a goal that we actually wanted, and so I think there is an interesting danger around like the clear definition of the goal can also lead to its own level of disappointment, because if you thought the only thing you had in mind was like, I need that house, and if I don't get that house, then, then it doesn't work, and then you get to that point and then you decide, actually I don't want any of that house. Did you feel like you were in a vacuum at that point for a minute?
Wil Schroter: Huge. OK, so let's let's talk about that. It fucked me up for a while, but. Because I didn't have, yeah, yeah, yeah, yeah, yeah, I, I didn't have a like, once you took that finish line or that trophy or, you know, however you wanna uh attack it off the table, I was like, I can't one up that. Right? In other words, if that's not what I'm looking for, then what the hell just happened? And I wasn't like, oh, that's cool, I'll just go on a cool vacation and, and that'll be, you know, it was all worth it. It was the first time where I had to really second guess whether this was all worth it. When you don't have shit, you can always say when I get said stuff that I don't have, that it will fix current problem, whatever your current problem is. I mean, it is, it is the bane. Of every, every marriage. It's, well, when we just fix this one thing, right, usually it's money, then marriage will be great, right? It almost never works,
Ryan Rutan: right? Had this conversation with the founder today, not about marriage, but just about like the the desire for an exit and saying like oh once I don't have the stress of this business, then life will be better. I'm like, remember that like you're creating a lot of this stress within the. Business. And so if you think you won't somehow find a way to create similar stress in your regular life when you no longer have the business, probably misleading yourself.
Wil Schroter: You know, Ryan is, you know, like every year in December, I take the month off and I usually go work more, but uh I was gonna say, yeah,
Ryan Rutan: I think you take the month off is probably not that you, you change to a more rigorous type of work.
Wil Schroter: Yeah, I go work a harder job and so it usually involves a lot of Sawdust and uh in sweat. When I'm doing that job, right, and I'm, I'm building stuff, and again, I'm, I'm not working this job, the startups.com job. Within a couple of days, I think I've told you this before, like at first I'm so excited to be able to do that cause it's my passion. I, you know, I love building things. But after a few days, I'm like, dude, this is really hard work, and I'm not against hard work, but I'm like, but if I had to do this for the rest of my life, this would not be fun, right? This would not be fun. And so usually by the time that month elapses, which is my version of a vacation. Um, I can't wait to get back to startups.com and I have so much more appreciation for my job. But, but, but I say that to say it helps me quantify the value of this job, the value of this sacrifice, because I, I, I get to step away from it for a while, and then, you know, kind of see it for the first time, and then kind of come back to it and like, oh damn, this was totally worth it.
Ryan Rutan: Right, which, I mean, just being able to step away from it is one of the the the payouts from the sacrifice, right? The the fact that you built a business you can step away from for a minute. But
Wil Schroter: I want to talk about fearing the goal a little bit, because I, I think that's fascinating to me because I, I've dealt with it quite a bit, and I certainly see it with other founders. Fearing the goal, that the way I would define it looks something like this. It either means you never really defined the goal, so and and maybe subconsciously you didn't really define what your endgame goals were because you were afraid of what they might be. Uh, either too small, too big, whatever, or the other side of it is you name something Bel Air house that when it came to fruition wound up being a bust. That's even more terrifying because you were so sure that was it and then you got there, it's just what you said about the founder with the exit. Every founder thinks the exits the answer. Right. Once I get exit, everything gets better. Everything will be different. And then they always become depressed after having done it because they lost their sense of purpose. They, you name it, the whole episodes dedicated to to the after effect. And I guess what I'm saying there is what's interesting to me about folks with with a lack of defined goals is they have no way to calibrate the sacrifice. For example, if your ultimate goal, Ryan, was to just go to Madrid, forget all the job benefits, right, or what we do and our freedom and stuff like that, just, just to get there. There would be a million paths that you could go on that wouldn't it wouldn't require any sacrifice. You could literally just get a job in Madrid and accomplish that goal, but your goals aren't that subtle. Right, or specific in this case. They're broader. You not just wanna be there, you wanna have the freedom, you wanna have um enough cash to be able to do things you wanna do, you know, you're not in a hovel. There's a lot more to it, and those things require uh sacrifice, right, and execution, all those things, and I think about that and I'm like. If you don't know exactly what those things are though, like all of those things that are important to you. Then you're many cases gonna over sacrifice. You, you, you're gonna like invest too much for shit you don't need this for something
Ryan Rutan: you don't need, yeah, or invest the wrong way, right? You're gonna, you're gonna push towards things that you didn't absolutely need and and forego others that you you would have enjoyed. Yeah, I feel like, you know, in, in the founder space that ambiguity is is ambitions comfort food, right? The the idea that we keep the goals amorphous. That we can just sort of like just keep going, keep it like we can just keep feeding the beast that we know how to feed, uh, without really having to answer these questions and face the fear of the payout, the what if, right? Like, right, cause with a fuzzy goal, we, we, we can't be disappointed. The challenge comes, right, to your point, like you didn't know exactly which house, but you sort of thought it was some version of this thing that you wanted to do. And so you, you couldn't be disappointed, but then when you get there and you realize now it does come time for this very specific moment, like leading up to it, it was just like, I'll just chase, I'll chase, I'll chase, right? Feed the ambition, feed the ambition, feed the ambition. When it comes time to eat that meal and you just go, I actually don't want this. We also can't be satisfied. So I think that's the the real danger around giving into the fear of some level of definition, is that right? We, we can't be disappointed by a fuzzy goal, but we also can't be satisfied by it.
Wil Schroter: Let's stick with that. That's why when we say founders selling their company, getting the exit, which everybody thinks is the goal, they get it and then they're pissed off about it. Uh, and again, just for folks that that they weren't familiar with this, this, the episodes we've done about this, that the high level version is we sell our company and we lose our purpose and we realized at that moment how much our purpose was was worthwhile to us and then it's too late. Our purpose being what we were building that company, our relationships with people, how we were getting up in the morning, we knew exactly what to do, etc. When you overnight strip all that away and you're like, but it doesn't matter cause now I don't have to worry because I have money and now you have no reason to go, you have no purpose in many cases, and people be like, oh well, I'll have purpose. I'll do charity. I'll do this. I'll, I'll work out a lot of like dude, try it. Let me be
Ryan Rutan: high quality. Yeah, yeah,
Wil Schroter: yeah, yeah, it's a problem, um, and you'll be talking to your therapist about it. My point is, it's one of those cases where when we defined that goal that I want exit, so I have money, so I have options, totally get that part, then what? What comes after that goal? No one thinks about what comes after that goal. It's because we're so we're working so hard just to get there, right? We don't plan that far ahead, but what happens is when we don't plan any further than that goal, we never play out that exercise. We never say, I want to get to an exit. OK, cool, and we talked to founders about this all the time. Awesome, uh, you know, if that's what you want, great. But let's talk about what's going to happen after that exit and make sure that those things are actually what you want. And then once we start chipping away at them, they're like, huh, and I really would have nothing to do, you could always say I'll start another company, which is what everybody does for this exact reason, or or you're like, well, you know, a big part of my social life maybe. Was wrapped up in in in running a company, um, either explicitly with like these are people that I hang out with and we go get drinks together, or implicitly like, I have a lot more to talk about with a lot more people cause we have the commonality of being founders or whatever. And I think what's interesting about that is when you play these goals out, right, when you really kind of play these goals out. They're not always exactly what people wanted, or they don't solve the problems. Rarely are they what people wanted. Isn't that weird? It is. 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: It sparked another thought though, which is, was there a point at which this happened to you or you realized that this was happening to you, that you were avoiding precision around the goal because you actually didn't want the answer.
Wil Schroter: They came in a different way. And this happened maybe right, maybe in the last year or so, I think maybe in the last year or so, for the first time in my life. I realized there's things I don't want, and I don't want that to sound like this privileged first world problem because that it's, it was really disappointing.
Ryan Rutan: I didn't need the 3rd Bentley.
Wil Schroter: Exactly, exactly, right. I had so much, you know, yeah, no, nothing like that. A big part of what drove my ambition was not having shit. A big part of that need was because I didn't have it, right? And I've, I, I've said this before. I said, you know, the value of anything is the fact that you don't have it. But once you do, it drops value, you know, uh, exponentially. And so I say that to say for the first time in my life, all those big honking goals that I had just started to be like, I actually don't want those things. I want the idea of one. I'll give you an example. I do not want a yacht, right? Now, most people are like, oh well, you know, how could you not want a yacht? Or like, you know, who cares, that's ridiculous. I don't give a shit. What I'm saying is like I actually don't enjoy boats whatsoever and I'm not like anti-boat, right? If you've got a boats 4 times as I recall, yeah, but I have no interest whatsoever in being yacht guy. I respect somebody else for being yacht guy. I don't want to be yacht guy, right? Now when I say that. That means I'm taking some big further goal that would otherwise require lots of extra sacrifice to get to off the table. For a decade, we had two homes, right? We had one in Ohio, one in California. I have no desire to have a second home. I don't even have a 1% desire to have a second home. I hated having two homes, right? It was a giant pain in the ass. But when I say that, I, I, I feel fortunate that that I had that experience, but I can also tell you I don't ever want to do that again. That takes a huge, you know, uh, thing off the table. Huge,
Ryan Rutan: and I think it comes from these places so often, right? Like in your case it came from from not having and then wanting to have, and then we forget that we can shift out of that gear at some point, right? When it's just like, didn't have and just like, so the answer to that is again it's it's have more. It's funny, I, I don't want a second home right now. What I do want is a big table somewhere. And it's not gonna fit in my Madrid apartment, right? It is not. There's no room in this place for a big table. What's a big table for the day? One of the things I do miss is a big outdoor table where I can gather a bunch of friends, I can cook some good food, and we can sit down and have a nice meal together, and so at some point. I want a big table again, but like, it's a pretty simple flipping goal, right? Like I don't need, I don't need to like, I don't need miles of land. I need like, you know, a, a couple 100 m and uh and a big table outside somewhere that I can get to within a reasonable amount of time and go and cook over fire or whatever it is I like to do out there. That I want. I do, I still want that, but like, yep, that's insanely achievable, right? That's not, I don't need an exit for that. I need, I need probably to plan for 3 weeks and figure that out.
Wil Schroter: Well, OK, so, but this is what I mean by that fear though, the fear of the goal. Once I started taking things off of my list, my fear started to go the other direction. I'm like, well, if I take my wants off the list, doesn't my ambition go with that? If you don't have a bunch of, you know, big ticket items or, you know, whatever your your your list is, I'm just, I'm naming random stuff, then all of a sudden aren't you ambitionless, or like, isn't the the best person, the old school Gordon Gekko that, you know, the only answer to more is more, and I'm like. I ran that path for a very long time, long enough to know that it is soulless at best and destructive at worst, right? Like every time I got thing, it became exponentially of less value than the next thing and the next thing, the next thing we've talked about this before. And I think I started to fear that part, right? I started to fear that like, what if I hit this threshold where there's just nothing else I want? Do I lose all my ambition? Does my superpower of of ambition directly correlate to having random shit that I don't need?
Ryan Rutan: As we get older and wiser, we start to realize we can have more of certain things that that don't come at the cost. of other types of things, but more houses comes at a cost. More impact to startup founders doesn't necessarily, and you and I are both highly motivated by that, right? We're still very ambitious in terms of wanting to solve problems for, for, for our people. And so I think that at some point you do start to just kind of shift what what some of those things look like and the the the payoff starts to look very different, right? And and the sacrifice start to balance out.
Wil Schroter: We have to ask, is the payout worth it? And I think maybe the scariest thing is being confronted with that answer. I'll give you an example. Before I started uh my first company, I used to work for a big law firm um called Jones Day Rebison Poke. Mhm,
Ryan Rutan: know them well. Yeah,
Wil Schroter: and so, uh, or for
Ryan Rutan: the wrong reasons. Yeah.
Wil Schroter: So I, I, I worked there at the lowest position you could possibly have. I was the backup receptionist, OK? I'm 18 years old, just, just because I, I, I, I have to paint this portrait. This is like 1993-ish, you know, I got my dates right, and because I didn't own a car back then, I used to get in my like 3 piece suit. Nobody wore three piece suits even back then, right? It was the only thing I could find a good.
Ryan Rutan: Please tell me this involves rollerblades.
Wil Schroter: It rollerblades. Not only did it involve rollerblades, I was so late for business, right? It involved a a suit, rollerblades, a briefcase.
Ryan Rutan: You are that stock image that I am
Wil Schroter: the stock image, right?
Ryan Rutan: Oh my God.
Wil Schroter: And for those of you that aren't following, there's a famous meme in stock image uh of a of a businessman rollerblading, and it says, I'm late for business, and I actually was that guy, so I was, I was way ahead of the curve anyway. So I would rollerblade to this shitty job. It was far away, by the way, like I was on campus that was in downtown Columbus. Yeah, that's a, that's a it's a long night. That's a good role. That's a lot of rollerblading anyway, so I'd go to this job and uh every day I'm answering phones and I'm, I'm like, you know, kind of like chatting with the attorneys and stuff like that. And on my last day there, the managing partner comes out. I didn't even know he knew who I was. He's like such a sweet guy. And uh he's like, hey Will, again, I didn't know how he knew my name. He's like, uh, I heard it's your last day, also not sure how he knew that. He's like, would it be OK if I took you to lunch? And I'm like, wow, that's the coolest thing I ever heard. I mean, like, just such a cool move, that guy, you know, massive influence and what he was in, and he took the time to take the fucking backup receptionist out to to lunch, right? The fact that he's a backup receptionist. Yeah, I know, I know, I know. And so, so we're at lunch and we're talking about life and everything else like that, and I'm like 1819 years old. And I said to him, I said, hey, I have to ask you, like you were at the top of this food chain. Was it worth it? Which in retrospect was like a pretty deep question to ask this guy, right, who I don't even know, right? But you know me, like I just, I just go all the way at all these questions. And uh, he paused and he was like, not really, and I thought that was like this incredibly honest, right? And he says, here's here's what he said to me. He said, Well, when I go to Best Buy. I can now buy any TV I want. I thought that was such a specific thing to say. It is also 1992,
Ryan Rutan: clearly at some point he didn't have a TV he wanted.
Wil Schroter: I can buy any tube TV I want in the nicest VCR. But I remember he said that specifically. He said, but what it took to get that. You know, to be able to to make that wasn't worth it. And this is the guy that was the managing partner. Right, like, like he was the guy, like that's, and he wasn't more young,
Ryan Rutan: right? There wasn't a bigger goal. There wasn't a bigger payout that could have been had. He got the biggest payout,
Wil Schroter: and I remember thinking when he said that, and I was like, how is that. I was expecting a totally different answer, OK? I was expecting a hype video where he was like, well, son, now that you've asked, you know, in order to become blah, yeah, and like I thought it was, and he was so honest and so clear and so kind, and I was like, I, I'd never forgot that. I never forgot that. And over time, when I was looking at my goals and my sacrifices, I kept thinking I don't want to be that guy. Like I'm so terrified of being at the top of my, my food chain. In in having that answer, and I, I think part of that for him, different era, different generation, etc. you weren't allowed to ask if the payout was worth it. It was like, if you had the payout at all, right, this is again a different generation, then you didn't otherwise work in a factory, so go fuck yourself, that's your payout, right, right? Like you didn't get the luxury of evaluating in quite the same way. Like he wasn't saying, hey, it wasn't worth it and I'm gonna quit tomorrow. He was like, yeah, it wasn't worth it, and this is what I'm gonna do for the rest of my life. But this is what I've got now, which to me felt like a death sentence, and so, um, a well paying death sentence, but, but my point is. He did contemplate whether it was worth it. This guy did everything right, you know, top law schools, you know, obviously worked insane hours. I, I can't even quantify what his sacrifice must have been to get there.
Ryan Rutan: He probably can't either, right? Yeah, right. Trade-offs don't come with receipts. X years, why miss moments. Well actually no, now that I think about
Wil Schroter: Ryan, he might be the only person that actually can because he had a time card for all of that. He could probably report, exactly how many are, but, but I guess like it's so rare that we are forced to stop and evaluate and calculate whether this was worth it. And the fear in all of us, it just terrifies all of us. I know it does me, is that we get to that moment and give that answer.
Ryan Rutan: Yeah, cause man, winning, winning the wrong prize is just another version of losing, and and the idea that we've we've done all of this just to open that door and like that's not what I wanted. It is, it's terrifying.
Wil Schroter: You see this in many professions, it's certainly not unique to to being a founder, right? That require a a a tremendous amount of sacrifice. The lawyer is a great example, right? Like it's, it's hard to get that far in a firm like that and not kill yourself to do it at every possible level for an extraordinarily long time. Uh, doctors in the same way, you know, the gauntlet that they have to go through just to start practicing is bananas. But for founders, what's different for us is we don't know if we're gonna get paid at all. What they're saying is, lawyers, uh, doctors, etc. is I don't know if it'll be worth it, but I'm going to get paid. Ours is, I don't know if it's worth it, and I don't know if I'm gonna get paid and I don't have to, yeah, it's a double whammy.
Ryan Rutan: You sound unreasonable when you say it that way, Will. We sound unreasonable.
Wil Schroter: But let's talk about the other side of the coin. I wanna kind of wrap with this this concept. What if we did get it right? What if after all of this sacrifice, we have that moment, you know, you and Valencia, me building my house, where it's like, you know what? This is pretty dope, right? Like, this, uh, this worked out awfully well. That's what we're hoping for. I see it happen a lot less. I think I fell into mine. Do you feel like you're there now? Do you feel like you have that alignment where you're sacrificing in your payoff of
Ryan Rutan: I think so, at at the current state, it feels like that, but this is still a very new, new part of the adventure for us, and we're at a pretty dynamic spot in terms of like where the kids are at in life and all of that to kind of see how, how that plays out, cause this, this leads to some, some big unknowns for us, right, which is like we've now created these three little. Very internationalized people. So what happens like as we get into our past our mid age into our older age, like, are they just gone? Are they like, what have we done, right? Is this for difficulties they're like, will that payoff be be be worth it. But I think in terms of the balance we're looking for in life, the time freedom that we wanted, the ways to enjoy our days, spend our time, and Look for like daily meaningful returns on that. Mhm. I can't imagine anything that had a better alignment right now than than what we're doing. Um, and I think that's an important piece of this is like, how do we turn that, you know, when, when you do find that alignment, and I think you, you end up being a bit more, I wanna say reasonable, reasonable is the wrong word, but there's there's I'm missing, I'm missing the vocabulary for it, but this kind of alignment turns someday into today. Yeah, and I think, I think it's very important because, because if you were still like, you know what, like building this house isn't enough. I need to build a 3 times larger house. I need to wait longer. I need to sacrifice more so I can build it like then it just continues to stay someday, and I think that there's really something to this, which is that like, for me, peace isn't purchased, it's specified. Yeah, right, meaning that once I'm able to decide that like this is actually the thing. And it's and it's what I want, then, then this is that that's great, right? Like for you, your goal wasn't jets, it turned out to be a workshop. This is where I wanna say like, I didn't, when I, I, when I said reasonable, I don't mean that in terms of it's smaller. It's truer. It's more real to what like you actually want to do
Wil Schroter: more fidelity, right?
Ryan Rutan: It's it is it's with reason. With it's it's with reason, reasonable in that sense, right? Not not reasonable and like, oh well that's achievable, right? You know, if you can't buy the Ferrari, uh, you know, buy the the the Matchbox version, it's nearly the same thing. Be satisfied. It's it's not it at all. It was that when you got down to what was actually going to move your needle, it turned out it was that, and that alignment is super powerful.
Wil Schroter: It, I didn't see it coming. And so for folks listening, essentially what happened was, uh, we ended up moving back to Ohio. Uh we're initially going to uh remodel our house uh that we don't own for 20 years. And as I started getting like the costs and like whatever, and I said to my wife like, you know, for, for what it would cost to remodel this whole house, we could just build a new house and for the same amount of money, just have a new house. That was the last time that was true. And
Ryan Rutan: so yeah, I was gonna say I feel like there may have been some scope creep somewhere, yeah,
Wil Schroter: yeah, yeah, an epic amount of scope creep. So, but actually, but that all kind of ties into it. So let me just play this thought out. I ended up going through this process where we find some land and I start designing a house, you know, I learned 3D modeling, so I learned how to design a house, uh, which was the most dangerous part of this because it costs nothing to draw a bigger box. It's building a bigger box
Ryan Rutan: that that that it also takes some time to realize how big those boxes are in real life compared to what they felt like in the 3D model. isn't that funny,
Wil Schroter: like when I showed you the 3D model like 4 years ago, and I was like, hey Ryan, I really want to build this thing. And then when you walked through it. And you're like, damn, I'm in your 3D model.
Ryan Rutan: Like it was I'm in the 3D model. Like I literally like there was like, I, I knew which way to turn when we walked from the living room to head like towards the workshop. I was like, I know exactly where we're going. I've
Wil Schroter: done this. You've been through this first person shooter before. It
Ryan Rutan: was, I literally, I had an Xbox controller in my hand and I was, I was navigating your home with that, so it did feel weird to have to use my feet, but I'll get over it.
Wil Schroter: There's a um uh this is the most bizarre side, but uh maybe you'll appreciate this. In the game Fallout for for the gamers of you out there, right? One of the Fallout series takes you to a resort called Greenbrier, and I think it's the open world Fallout, if I'm not mistaken, right? But they, they, uh, Greenbrier is a resort in West Virginia.
Ryan Rutan: I've been to the real Greenbrier. I have not been to the, the Fallout version, but now I'm super excited because There is a nuclear shelter. That's why there
Wil Schroter: is, right? And and so, uh, in the game they turned Greenbrier into like it doesn't matter, but the point is when I went to Greenbrier for the first time, I actually knew where everything was because I had played the game, right? It was bizarre. I mean it wasn't one for one, but it was pretty close anyway, huge tent, um, but you're welcome fallout hands. So we get to the point where like, you know, I'm I'm kind of like in designing this house or whatever, and something really interesting happens. I start to realize that this is what I wanted. It wasn't, here's what it is. I didn't want to buy a house. I wanted to create a house. I, I wanted to create something where every single thing had my fingerprint on it. I wanted to design every square inch of the house myself. I wanted to pick out every last thing from like the, the timber grated wood we're gonna use to the quality of hinge we're gonna use, right? Every single thing. And I also wanted to build it with my hands, right. And so about a year ago, give or take, I'm driving to the job site, it's freezing outside, right? It's we're in Ohio, it's like it it couldn't have been more than like 15 degrees outside. I'm in my pickup truck, I'm driving out to the job site, and I'm gonna go um run speaker cable long before you're ever supposed to run speaker cable, and I've got the biggest smile on my face. It's like 6:30 in the morning, it's cold and dark outside and I've got a huge smile on my face, and I just, I just noticed it while it was happening. And I was like, what is wrong with me? I'm like any rational person on a Saturday at 6:30 in the morning at the very least would be sleeping. But the last thing they would be doing is racing to a construction site to go put speaker cable up when there's not even a roof on the house yet. But I realized. This is what I've always wanted to do. So what you wanna do, right? Like that's it. I'll never forget I'm sitting in the cab in my truck by myself and I'm like freezing, and I'm thinking to myself, this is insane. But Bel-Air wasn't what I wanted,
Ryan Rutan: right? Bel Air was status and status is seductive, but it was the craft of doing it yourself that actually satisfied you. It's, it's such an amazing finding.
Wil Schroter: It's been this amazing journey for uh for me, and, you know, if for those of you that know me and have had to listen to me drone on about this thing for the last couple of years, thank you for your your service. But like, I honestly, I finally found some. that that was worthy of the sacrifice. This gave me some funding to do what I wanted. It gave me the the the freedom to do what I wanted. There was just everything finally paid off in a way that for the first time in my life, I actually felt like it was a full payout. Like I was, I was fully aligned with my sacrifice and Ryan, it was a huge sigh of relief.
Ryan Rutan: All of a sudden you realize like, That decision I didn't make, it wasn't actually the thing, right? It's the things that I'm doing now that that are the thing.
Wil Schroter: Can you imagine, Ryan, if someone like 32 years ago was like, hey Will, one day, if you sacrifice everything and give up all of your relationships, you'll be able to drive your
Ryan Rutan: construction contractor on your own construction site, right?
Wil Schroter: Like who never saw that coming. But man, like, you know, I'm an obsessive carpenter, so like I, I got to build everything I've ever wanted to build with like when I say no limits. It's not entirely true. There's always limits, but like reasonable limits. I get to do really extraordinary things, and I, I wouldn't, there's no way I would have been able to do this on, on another path. So it's very clear that this was like a singular outcome. But when I'm out there, like I was out there, you know, I told you this morning at 6 in the morning, I'm, I'm putting speakers in the ceilings that actually do exist now. And I'm like, I'm covered in drywall, you know, I'm covered in sawdust. I'm sweating like crazy because in this case it's like 90 degrees outside. And I'm like, I'm so happy. I'm so incredibly happy, cause I find something that that aligns with the sacrifice that that feels like damn, this is, this is what it was for.
Ryan Rutan: Now, it's, you know, when we we stop optimizing scale and we start optimizing for saver, yeah, something really special happens, man, like we don't need more, we need maybe fewer, but certainly like deeper and better experiences, and I think that like absolutely. Does come with experience and time, but it also, of course, you had to create the opportunity. It comes from sacrifice, sacrifice creates the conditions for it. And now you're you're out there, you're building again with meaning, which of course there's a very strong metaphor here between the house and another startup, so yeah, it doesn't go unnoticed. However,
Wil Schroter: it it aligned well though and so here's what I would say. I would say for founders out there that are kind of wrestling with this. And we're all wrestling with it at some level. There's there's no version where you can go through this startup thing and have no, you never wonder whether the sacrifice is gonna be worth it, or in many cases know exactly what the the end game is. And and if you think you do, awesome, often when you get there it's not what you thought it was and that's OK, part of the journey. But here's what I would say, if you're going to make this sacrifice, commit to something that you feel that you can see in in touch and taste and feel that if I can get this. It's going to be worth it, but the most important part of that is why, and what happens after that. Once I get that, then what happens? You know, when I wake up the next day and I bought the thing or I've done the thing, whatever, when I wake up the next day, what is demonstrably better? Because for all of us, if we can't define that next thing, if we can't figure out what the rate of pay is going to be for our sacrifice, then none. Of it is ever worth it, and that is the worst feeling by taking everything you care about and put it into essentially nothing. So take that focus, take that drive, take that sacrifice, and make sure when it's time to cash all those chips in, that you cash them out big and you're smiling like we are, cause you've got that perfect alignment.
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.