Startup Therapy Podcast

Episode #112


Ryan Rutan: Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan joined as always by my friend and partner, the Ceo and founder of startups dot com Wil schroder. Well today let's dig into something that everybody experiences at some point to some degree or another timing may vary. Mileage may vary, but we all sort of know there are sacrifices that we make to build these startups. But today I want to talk about the regrets that come as the cost of those sacrifices go back in time for me man, when is the first time that you remember really regretting some of the trade offs that you had to make to make this path in life work.

Wil Schroter: Yeah, I think it was the first five seconds after I started a startup.

Ryan Rutan: I mean

Wil Schroter: the funny thing is I don't remember at the time feeling it happening right at the time it was just all these kind of, you know, micro sacrifices. And I remember specifically like if I had to go back, like if I had that like Polaroid moment of when it all started. Like, you know, when this movie began, I'm at Ohio State, I'm like a sophomore. Maybe I just started my first company Blue Diesel and I'm walking across the oval, which is a quad for most universities and I know I'm rollerblading. No, no, I'm not walking. I take that back, let's give this, it's due in time.

Ryan Rutan: Everybody take a minute to visualize. Were you carrying a briefcase or Yes,

Wil Schroter: actually it's time for business. And uh, so, so listen, so I'm rollerblading across campus and I remember going across the oval and I look over and a bunch of my friends are playing volleyball and I remember thinking at that moment, like I want to do nothing more then go play volleyball right now and I didn't and I continued to skate along, right? And I thought to myself, well I can't do it today because I've got a ton of stuff to do. You know, I'm head deep in the startup thing. I don't even know what a startup is at the time, but I know it takes a lot of time and I know I need to skate to it right now. And so I give it up and not a day goes by in some form that I don't remember that moment, Here's why that sticks out because now every time throughout my day that I do some little micro sacrifice, I remember that day because I know I'm not getting it back right, There's no version where I'm going to be 19 again. And all my friends are gonna be sitting on the quad and we'll just be playing volleyball because we have no other cares in the world that will never happen again. And I can't get it back. And that's just one small piece, right? But like that was the beginning. If you want to talk about, you know, when does this begin? You know, when did this snowball start? The mountain down the mountain. That was it.

Ryan Rutan: That was so, but I want to be more specific with my questions because I have similar experiences, but I want to see if they're, if they're different in terms of, that's the point at which the sacrifice has started, right? That's when the sacrifices started. But for me the regret didn't kick in until later because

Wil Schroter: the activities

Ryan Rutan: that I was passing up, I was still playing soccer at the time, right? So I was getting in a little like that, that was having some fun. It was the other things that was passing up on, it was like, let's go get shitfaced drunk and wake up at three o'clock tomorrow afternoon and skip a couple of classes, Those things just didn't appeal to me anyways. And I was always like, no man, I got this other thing I want to go do, right? There's this new thing called flash and action script and like I want to go play with it, right. I was that much of a dork. That, that's what I wanted to do. And so at the time now it still was a sacrifice, right? Because parties hanging out doing things with friends or just going to study together, whatever it was. I skipped a lot of that stuff in order to go and do these things. The thing was in my case I wasn't, maybe, maybe it was the speed at which you moved by on those roller blades. I don't know, but for me it didn't catch up to me until years later when it was like a group of people got together post college and had like get together a party, a cookout at somebody's house and I wasn't invited and it was all people I knew and I realized well why would I have been invited? I disappeared from their lives years ago in order to build the startup instead. I opted out of those things. And it was at that point for me that it was like, man, had I done those things, I would have different options in life right now in terms of being invited these things, getting to go do some other things that would be fun now that maybe I've got a little more time for, maybe I don't, but maybe I would do them anyways. But I think there was a big difference for me in when the sacrifice was made and when the debt came due it, was it the same for you or did you start feeling it right off the bat?

Wil Schroter: Well, you know, at the time because I was so young, I didn't understand what the debt was, so to speak.

Ryan Rutan: I

Wil Schroter: just assumed, okay, I'm not, I'm not playing volleyball today. I'll play volleyball later when I become rich. I'll be able to play volleyball all the time. Right. And so in my mind,

Ryan Rutan: volleyball court, in my living room.

Wil Schroter: Exactly. I was trading this for that. What I missed was those very moments. The moments I was trading weren't all replaceable. Right? And that's the part where at the time I had no concept for whatsoever. But I think that's what we'll talk about today. Alright. So before we get into this next topic, I just want to let you know what we talk about here is like 1% of the conversation, you know, really, this conversation is going on all day long online at groups dot startups dot com where Ryan and I pretty much talk endlessly with founders about every one of these topics. So if by the end of this discussion, you like the topic and you want to dig into it a little bit more with Ryan and I just had two groups startups dot com and we'll pick it up from there. I think today we can talk about how many of the things are we gonna risk as far as our time and moments that we actually can't get back that no matter how well we do in the future, the risk that that we're, that we're putting up won't return. There is no R. O. I on what we're risking right now because we believe we believe there is right. The lie we tell ourselves the mythology around startups is that we're going to give up a bunch of stuff now and that there's a return later and that is mostly true just to be clear what we're talking about today is the other part of the pie chart where it's not

Ryan Rutan: right. We've talked about this before and I've said that, you know, there's no interest earned on happiness deferred you don't get more happiness later because you give up happiness and moments now. But I think that to your point, this is this is a subtle but really important difference. Some of those experiences simply will not come back around and if you do recreate them, it's not the same thing, right? Like I'm not sure I'd want to go play shirtless volleyball on the quad right now. Right? Even though I can I could go do that. I've got the time I have the freedom nobody else wants to see me play shirtless volleyball in the quad.

Wil Schroter: I'm trying not to think about it right now.

Ryan Rutan: I know. All right, so the and I'm being glib here, but that's the reality. Some of these things that we give up, there isn't a way to meaningfully recreate them later. And those are the ones that really accumulate this debt around experience. And that's what creates the regret

Wil Schroter: right now. Actually, let's fast forward just a touch because I think some interesting things happened in a short period of time. Fast forward just a few years later. I'm in my early 20's say 20-23 and we had some really great things happen at the agency. The thing, you know, kind of took off, I became a millionaire in a short period of time, right within just a few years. Incidentally, right at the time that all of my friends were graduating college. Okay. So you had this really interesting kind of moment where hey Will's rich I guess. But we never saw the part where he, you know, had had forgotten his entire college, you know, memories, right. We just see what was apparently gone a lot. He never wanted to hang out with us and now he has a lot of money. We never saw the dead in between now. Here's how it looks like from the outside. And I think this is what starts to detract and throw off a lot of our fellow founders. I think from the outside you look at it as, hey, that's just a few years invested. No big deal in the return was there. And I think if you ran the calculus, that's probably true. You know, the amount of opportunity in my future far outweigh you know that what it cost me in my past. However, that's where the math starts to get a little bit in early Because we're just talking about my early 20s, forecast that out a bit, Make it all of my 20s, Make it my 30s, make it all the time with my Children. Right. Make it all the times where I'm healthy, all of those things right? And all of a sudden the calculus doesn't work so much that, that Ry isn't quite what we think it is. That's where I think we start to get really thrown off because we think no matter what we do the R. O. I. Is there but I don't think we really calculate what the true cost is and Ryan I think that's where I was thrown off.

Ryan Rutan: Yeah and I think it's easy to do right because again we assume that we can replace some of these things. We assume that we'll be able to make up for it after the fact. But let's use one of the examples that you gave right family or health either let's use both young family right and you're not going to get I don't care what the return on that investment was like let's say you 10 X. Your company in that period of your kids being 0 to 8 years old there's no amount of money that buys that back from you or erases the regret from having missed those years. It just doesn't happen right? That's gone. It's not coming back and there will be lifelong regrets on your part and there will be lifelong regrets and baggage on the part of your Children and the rest of your family. Hell is being the same thing right? Work like crazy make a bunch of money and have all the assets that you ever wanted die anyways. It happens it happens it's inevitable happens to all of us. The timing in which all of these things happens is also important as we continue to give up and give up and invest and invest and invest, looking for that bigger and bigger and bigger roi the time and the ability both from from just a pure time standpoint and having enough physical health, stamina, emotion, mental well being remaining to actually enjoy or utilize, it diminishes right. They're both exponential curves. One goes this way, one goes that way, make sure you don't miss those curves, trying to build something a little bit bigger or even a lot bigger that you'll have no benefit from in the future. It's one of the biggest pities that we see in the startup spaces that people run themselves into the ground. They do build something great, They make sacrifices that do pay off. You can't question that there's no question around the mathematics of their sacrifice paying back. The question was the worth and the value of that additional return and I think that's where we get it sucked up.

Wil Schroter: I mean, so I mean if we think back, like how do we know which things are the once in a Lifetime moments, like how could I have possibly known that that particular day as I'm rollerblading across the quad, that that was the once in a Lifetime moment, right? You can't however, however, I do believe that you can zoom out of touch and you can say 100% of my life isn't unimportant right now right? Had I had more wisdom back then or had the foresight that I have now. I would have gone back and I would have said, okay, any one moment may not be the seminal moment, But some of them are said differently. 100% of those being cut out is a problem, right? So I'm gonna take x amount of time, maybe it's 20% of my pie chart and I'm going to feel good About investing that time. I need the rest of it. Look, I mean, I need as much of the other 80% as possible, right? But The 20% that I'm gonna put toward having a couple of those nights out having a couple of those volleyball games etc are specifically because while I want this success, I want I don't want it to come 100 at the cost of everything else. And I think it's easy to do that, right? I think it's easy to get so swept up in what we're trying to accomplish, that we just delete the rest of it and we just assume that we're getting it back. And I gotta say this building that a bit. Well, I would say the R. O. I of having, you know, put that investment and was was tremendous. It put my life and my career on a forever track that I would have otherwise never been able to get to in just like a regular 9-5 job. And so that was wonderful and I got to have all new experiences that I wouldn't have otherwise had also awesome. But imagine this, imagine if every time I got one of those new experiences, I was still using the same math that whatever I'm about to do now doesn't matter because I still have to work on startup career etcetera. What I'm saying is you can easily erase that other 20% even after you think you're successful right there isn't this ticker tape parade where like, well now you're successful and now you just somehow turn this stuff off. If anything, it's a learned behavior

Ryan Rutan: I would say it becomes habitual Yeah, exactly, exactly, Absolutely man. And I think that as we think about these habits and they formerly right, we start to get used to making these trade offs and we just assume that's what it takes and then we stop even thinking about it. I remember at some point it just, it was no longer like should I do this or should I do that? It was like, hey Ryan, we're going to and it was just, it all turned into noise. I didn't even hear what the hell the offer was. It was like, no, I got some shit I'm going to go do and I already know what that's going to be right. So the signal in my life was all related to the business and everything else was noise and at some points we've talked about this, You've got to be that hyper focus. You've got to be nose to the grandson. You have to be myopically centered on the outcome of that company. But when that just becomes a habit, right? And I think that anything that just becomes a habit that isn't obviously good for you like sleep or eating well, always has to be examined. And it took me a long time to the point where I started to think about that as a habitual behavior. It didn't feel like the habitual behavior. It felt like my job. So I wouldn't think of it as a habit. So here's where it becomes a problem. I'll give

Wil Schroter: you an example every morning. My son will, I was four years old Comes into my office where I'm working at like 7:30 AM. Let's say he's about to head out to school and he does the same thing every time he creeps over right? Like I don't notice him coming and then then he like springs himself and he's like dad, he's like, look over there and and it's it's so funny because in his mind like he's tricking me every single time, right? It's like, it's, it's always a new thing and I love to play along and I'm like, wait, wait, what is over there? I don't understand, right? And he's like tag, you're it, right. And then he sprints out of the room now, here's where the habit comes in, right? The habit comes in because for the split second before I jump out of my seat to chase him. I run the math, right? I run the math. How much do I have to do today? What am I working on right now? Is this so important that if I don't chase him, there's gonna be some consequence, etcetera. And I gotta say, and I hate to admit this, but it's true. A fair amount of time. I stay in my chair and I tell him, hey man, I got something I'm in the middle of, you know, I'll play with you later and I think everybody does that. I mean that's not unheard of, right? You know, not every parent drops everything every time their kid wants to play,

Ryan Rutan: just the good ones

Wil Schroter: will. Uh, but I'll say this every time I don't get out of my chair, I regret it. Right? Of course. What's

Ryan Rutan: worse? Every

Wil Schroter: time I don't get out of my chair, he regrets it. Listen to what you just said. It's not just about me anymore right now. I'm creating regrets for other people as well. You know, by the way, I just want to mention if what we're talking about today sounds like the kind of discussion you wish you were having more often you actually can, you know, we're online all day everyday, working through exactly these types of topics with founders just like you. So any question you would have or maybe some problem you just want to work through. We're here and we love this stuff and we're easy to find. You know, head over to groups dot startups dot com and let's just start talking. And so now what I'm willing to pay isn't what he's willing to pay, right? And what habits does that start to build for him? Like, hey, my dad was okay not playing with you whenever I wanted to. So I guess, you know, I've got kids now and maybe I'm not gonna play with them all the time because that's what I learned. It's fucked up, right? And all these behaviors started The day I was rollerblading across the quad damn near 30 years ago.

Ryan Rutan: Roller blades are dangerous. It's obvious. Yeah, yeah, it does. That's the thing, right? And it's a massive amount of deprogramming that we don't even realize is required. We don't see it coming because this happens over time. Right? Again. This isn't, this isn't like, you know, simple mathematics, This is, this is calculus, This has changed over time. Those sacrifices that we're making may feel exactly the same. I'm still giving up or not giving up five minutes of my time, right? My friend calls. I could pick up the phone, I could talk to him for five minutes. That's still a five minute conversation, right? My kid comes into the office and wants to show me a drawing. It's a five minute segment of my time. The difference is 20 years ago, when my friend called and wanted that five minute conversation with me less impactful to her life than when I don't look at my six year old's drawing. Alright, So the impact to us stays the same in terms of how much of that time it steals from our startup company, how much it will impact my output for the day. But there's an exponential increase in the cost of that to everyone else. And to this compounding pile of regret that we're building. And that's the part that's hard to see. What we don't see is that our interest rate keeps rising year, over year, over year as the value of the activities that were dodging become that much more valuable cruising past that volleyball match probably didn't change your life a ton. I don't know unless the winkle vai were the setters in that match. That that could that could have been an important meeting. On the other hand, missing your child's first volleyball game. Pretty big deal. Right? So the value of these things that we're trading off, whether we see it or not because we just allocated to time, we just think about in terms of what does this cost me? What will I not get done because of this? We don't play it out all the way to say, what's this going to cost everybody else and what's this going to cost me in the long run when I've actually paid all the interest on it and I think that's where it gets super dangerous and we have to lean back and pay more attention to these trades that we're making.

Wil Schroter: Yeah. And, and, and like we said before, we have to recognize that when those moments come, that yeah, there will be another time when when will comes in and he wants to play tag, right? But that's not the point. The point is I have a finite number of those moments, right? There are a lot of things I can probably mortgage to get something else right, that I can gamble or bet on to get something else. We start to get a point in our lives where this isn't that right now, you take that because this is this is the fundamentals of every founder. You take that to all of our relationships, right? You take that to all of the time that we could have spent building our relationships. Like you were saying, taking a call from your friend or catching up with your friends from college all of that time that everyone else generally gets to spend. We don't, you know, to be fair, it's not that easy, we can't just say, oh well, fucky it, I'm going to actually spend time and you know, and, and allocate all that time and not give up any of it, it doesn't work that way. And if it's working on you, Yeah, I mean it's really really really difficult to say, well I'm not gonna do any of that and yet somehow magically I'm gonna have the time and focus to build my startup again. If you do, I applaud you, I'm not saying it can't be done, I'm just saying I've never seen it and I've been at this a pretty long time I think for a lot of folks especially getting into this, the problem is they haven't seen it yet, they've seen the part where they make the investment, they haven't seen the part yet where the investment comes at cost, they can't pay back. And I think that's the part where again now at the station in my life Ryan, I know in your life where we're starting to look at this and going well

Ryan Rutan: shit

Wil Schroter: or if we two xr startup, if it comes at the cost of our you know, not seeing our kid like there are certain things but now we know we can't pay back back then. I always thought that no matter what the sacrifice was, I'd be able to pay it back in the future and now I'm like if one wants to play tag let's go play tag because I actually don't I have something I could invest in that's gonna have a bigger R. O Y than that not making my kid out of calculus here, but I'm just saying like I actually have learned my lesson and Ryan and you spent amazing time with your kids and your family. I'm sure you've come to the same conclusion

Ryan Rutan: for sure. Like it's silly as it sounds like just Think about these things, right? Like think about what you can actually differ and what you can't, is there a version of playing tag with will when he's 30 and you're 70?

Wil Schroter: Right? I

Ryan Rutan: mean, I suppose there is, it just looks a lot different right?

Wil Schroter: At that time.

Ryan Rutan: That's it. Right? So, well you may be living with him at that point. We just don't know like if he puts one of the breaks on your wheelchair is going to be a lot harder to catch him. So it's yes, So I think that that's the thing that we fail to do and I think it's partially because we get so used to being so focused on the startup company and just assuming that the rest of life will happen around us, right? Everything else is peripheral. There's somebody else there to take care of that, somebody else will make sure that those things happen. And for a while that's largely true and we can go without those things. But as the stakes go up as families get involved as mortgages get involved, as aging parents get involved, there's so many other things that come in that are critically important to your life and the fabric of your well being that we have to reassess at least periodically. This doesn't need to be constant reassessment doesn't need to be real time analytics on your life, but at least once a year lean back and go, okay, what has changed about the situation now? What stages are my kids at? What's the state of my marriage? What's the state of my own health? What do I need to do differently this year? What do I need to be aware of? What our trade offs I've been making that I need to reconsider. I can't just keep doubling down on this bet in the hopes that I keep hitting because at some point that bet is going to miss and there will be severe consequences, lost relationships with friends, lost relationships with colleagues, lost relationship with spouse, lost relationship with kids, loss of health, loss of life. Alright. We both have recent examples where it's gone that far and those our trades that like you just shouldn't be willing to make, you don't have to at that point, you really have to call into question, what am I trying to accomplish and is trading all of this time and for going these experiences and breaking these relationships the right tool for that job. And I would hope that you would come back with the answer as no,

Wil Schroter: I think the part of the problem is that for us this never turns off. There isn't like a stopping point. I'll give you an example when I go on vacation, I don't just turn everything off. Like when I hear people, I'm just gonna turn off all my notifications and I'm just gonna like that must be nice, right? Like I'm not gonna do that because I want to make sure that the ship goes sideways. It's cool that you can do it now. Let me build on that a bit excited about that position, right? I'm not like, oh, this is probably the best go. I can't turn it off. Like mentally I can't, there's no version where the weekend starts or the evening starts, my vacation starts and I'm just like,

Ryan Rutan: these things are always there, right? Always there.

Wil Schroter: It doesn't matter. I'm turning off the device, I can't turn it off in my head. I've

Ryan Rutan: never been able to write.

Wil Schroter: So here's what that resulted. I'm telling you ahead of time. I don't have a single vacation that I've ever gone on where I've actually gone on a vacation, right? I go on vacation while I'm in the airport, I'm checking, you know, email or messages constantly. You know, while plane doing work basically, I don't have to, by the way, just want like the point of this is that I don't have to I don't have a vacation where I've just turned off because for 30 years I've programmed myself to say that I'm not allowed to go to that volleyball game, right, that my focus has to be on my startup and so that I actually don't have the tools to turn it on and again, turning off my notifications doesn't mean Jack sh it it's not going to change at all. What's going through my head?

Ryan Rutan: A lot of

Wil Schroter: people are thinking, boy, I hope I get to a point in life where I'm successful and I could never. That sounds awesome.

Ryan Rutan: Yes. Yes. If you don't break those habits, I think that was kind of what I was getting at in terms of re evaluating those points because there's a number of things that you can reevaluate their, let's let's look at your case in particular in your case, you've got two partners who can be that last line of events and who are paying attention to those things while you're gone. If something comes up and there's a pants on fire situation, we will message you, we will call the hotel, we'll fly there. If it's that bad, I don't mind visiting Mexico. The thing that I've been able to do, turning off notifications, filtering notifications was really important for me because this thing was going off constantly and it was forcing a bunch of trades in time that actually had no. So the things that we've been talking to up until this point had an roi these were making major trades that had compounding impacts on our future, both positive and negative. The thing is I realized that 80-90% of what came through as alerts the emails from strike the emails from charge if I, the notifications from slack for a bunch of channels that I monitor, but don't actively participate in. They were just time wasting and they were things that could happen whenever. Not right now, but I started trading right now constantly and we all know there's this huge power and focus and when that focus gets broken, it's a really, really bad thing, particularly were trying to do something like relax, go on vacation. So one of the things that I was able to do was set up just sort of a cascading system where I have a few people who are monitoring my inbox monitoring slack when I'm away. If something pants on fire comes up, I know about it and I know that it's going to come from one of three people and if it's not from one of them, it means it's not that important. Right? And I can just let it go. Do I still think about it. Is there still a little bit of anxiety in the back of my mind? Of course there is right. But it's half of what it used to be. Maybe it's 25% of what it used to be because I know that there are systems in place that will bring up anything that's super critical and I would urge founders to constantly re evaluate what are those things that you really, really need to be paying attention to. If I'm on vacation, I get an email about somebody who has a random payroll question, do I need to stop swimming with my kids to answer that? No, probably not. Right. So you've got to learn to prioritize a bit and you've got to reevaluate what are those sacrifices are going to be the difference between making this business into what we want it to be continuing its healthy growth and just things that we can spend our time on. Because there's always something more like I think you said it earlier, the startup never sleeps. It doesn't the start business that doesn't ever sleep. That does not mean the founder can't and in fact the founder needs to write, the founder has to self care, we have to rest, we have to find those moments to unplug. So I'm going to sign you up for a course on being better at vacations. I'm sure it exists somewhere

Wil Schroter: here is kind of a bit of a misnomer. Rise to everything. I just described this number is that it's the notifications or access to my laptop or my my phone. I could throw it in the ocean. It wouldn't change my vacation. The problem is, and again, but back to the things that we, that we risk by even developing this mentality. The problem for me when I'm sitting by the pool came on and I start up the whole time. Should I know

Ryan Rutan: for sure. Yeah. I mean insane. She hated behaviors are tough to deal with and particularly when at some point in our life, they were so important to success to progress that it's easy to get fooled into believing that that's what's necessary forever again. We'll go back to it. This is why you have to re evaluate and say, is that level of sacrifice still necessary at this point? And those check ins need to happen pretty regularly or you're going to miss them and you're going to develop that habit and you're going to get stuck in this analytical pattern of I can never stop thinking about my business or something really bad is going to happen. As founders, we are experts at manufacturing anxiety if there's a better, better population on the planet, I'd love to meet them, just like I feel a little bit better about myself, We're great at manufacturing anxiety and the reality is, there's a lot of things that can go wrong, were also masters at fixing ship, right? So at some point we have to recognize that yes, some things will go wrong in the same way, we can't protect our kids from every cut scrape bump, insult, broken glass, spilled milk, whatever, we can't protect our startups from it either, and we shouldn't try and I think that's a big part of where that anxiety cycle comes from is us saying if I'm not fully focused, some little bad thing will happen and that will be the end of the world and we talked about this in our failure episode two where failure isn't this black and white thing where one day it's shangri la and the next day we're in the depths of despair, it does happen. That can happen. That's typically not the way it goes, right. It's a series of unfortunate events which we can work to turn around at any given point. And I think it's about going back to prioritizing and being clear on again. What do I have to trade to make that happen? And if it's not something that's so critical in that moment, then stop making those trades right, go play tag with will go play some volleyball. Although I'd argue that's probably not our sport, but you know, whatever.

Wil Schroter: Alright, so that was fun, but let's actually keep this conversation going. You've heard what we think about this, but you know, Ryan and I would really like to hear what you think and we're online all day long, pretty much talking about every startup topic you could think of, from fundraising to customer acquisition to just really how to get all of this crazy startup stuff out of your head. And there's tons of other founders just like you, they're weighing in on these topics so you'll get a chance to just hang out and meet some really smart founders. We're also super, super easy to find. You head over to groups dot startups dot com and let Ryan and I hear what's on your mind, let's get to know each other a little bit and let's just start having more of these conversations.

Ryan Rutan: Mhm.

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