Startup Therapy Podcast

Episode #97

Ryan Rutan: Welcome back to another episode of the startup therapy podcast, this is Ryan Rutan joined by my partner and friend Ceo and founder of startups dot com Wil schroder Well, you know, we hear that money can't buy happiness and it's one of those things where in startup land, you know, we start businesses for lots of reasons, right? But money is always at least some component of it, because at a bare minimum we sort of needed to survive, right us the business, the people that we pay to help us build the business, you know, there may be some grander vision there, but at the end of the day, the things need to make money and we've sort of tied this idea that, you know, each and every one of our own versions of happiness somehow has money tethered to it, which rather implies that like once we have money we're happy in your experience and mine, let's dig through like where that's been true and for how long and what the fallacies

Wil Schroter: there are. Well, I think it's a big thing to be so convinced of that money can buy happiness because think of how much time and effort and and we're deferring all these hopes and dreams and you know, relationships for this goal and what if that goal that money is going to buy this happiness was untrue, you know what if we were spending all of that time toward this and we got over the other side of it and we were like, wait a minute, that didn't do it at all, what I thought it was going to do. Exactly, and I never really spent the time to unpack what was essentially a myth and I've got a caveat this, right. And I think we've talked about this before in other episodes, it's always easy for someone to say money can't buy happiness because they usually have it

Ryan Rutan: right, It's typically, it's typically not said by somebody standing in the soup kitchen line. Right.

Wil Schroter: Exactly, right. And so I think what we should talk about today a bit is not just why money can't buy happiness, but I think we should also talk about why being in debt or being on the other side of it is actually just a different problem altogether than happiness, because I think at its core, what we're missing is the fact that not having money breeds endless misery, right? That's well proven, and I don't think anybody needs to be convinced of that, but I think there's this concept or this causation, I think if you said it before, whereby if I change that and I have money, well that must mean happiness comes because not having it makes me sad.

Ryan Rutan: Right, well let's talk about the difference between those two things and let's talk about them in terms of their longevity. Right? So when you think about debt and happiness from a timeframe perspective that doesn't necessarily stop, right, Happiness is a fleeting moment. Right, Right, Right. I won't quote George Carlin on this one, but he had some nice thoughts on what happiness is they were all fairly short lived things. Whereas conversely debt can go on and on and on and the emotional impact of that can go on and on and on interestingly, you know and I think this is more of a U. S. Problem because I've talked to more and more people from far flung places where debt is not the automatic choice. It's as though we've become so accustomed to having some level of debt and when I say some level of debt, the level of debt that we're willing to accept in the U. S. Is massive. Like when I tell people that yeah you know like typical you know people are buying you know $500,000 homes like Where did they get all that cash? And like they don't they don't have any of that money, they put down 5%, they're like wait what? They put down $25,000 and now they have you know $475,000 in debt. I was like no it's actually more than that because there's closing costs, all this other stuff, they're just like that's insane and how long is that going to take them to pay off? Oh you know 30 years. Although there are some companies now doing 40 year mortgages and they're just like their mind blown, they're like. that feels like forever and I think that is kind of the point. Right?

Wil Schroter: It is. And listen, I think at its core, like we were saying earlier, the fact that so much of us have so much pointed towards getting out of this, I think part of what we need to understand is what problem were actually solving and conversely what problem were actually not solving, right? So let's talk about the death side first, right? You know, not having money because the way I describe it to folks, not having money is like having a huge giant honking bruise where you're constantly feeling and every time you move you feel it, it's always on your mind, it's always preventing you from doing something right? It's annoying as hell and all you think of, if I can just get rid of this bruise then I'll be healthy.

Ryan Rutan: You just described going to the gym for

Wil Schroter: me, but every single day, right? But the truth is once that bruise goes away, you're not more healthy, you're just as healthy as you ever were to begin with, right?

Ryan Rutan: Yeah. And you're not necessarily happy about the fact that it's not there every day, right? I suppose it depends on where it was appearing, but yeah, it's you know, if we're going to tie this back to happiness, it doesn't mean that all of a sudden now I feel great because it's gone right now, I just feel normal

Wil Schroter: again. Well, so to stick with that when I was starting off my career kind of, you know, through childhood and stuff, I didn't have any money. I was super, super broke and all of our problems were always mapped back to money. And I think the other aspect of this that's worth noting is that money is such an obvious thing, it's such a binary thing that you either do or you don't have to solve some sort of life problem, right? So you take a couple and they're super stressed out and arguing all the time because they don't have enough money to pay bills. It's super stressful. But what that tends to kind of mask is maybe even if they did have the money to pay bills, they'd still be arguing,

Ryan Rutan: oh, I can point to a few that I would be willing to put very, very good odds to the takers on that bet,

Wil Schroter: that would still be the issue. And again, the same goes not just from relationships, but those relationships exist within startups as well. Think of two co founders who were kind of leveraged to the max on cash and they're arguing over all kinds of stuff constantly with this idea that once we got past that and once the startups making some money, you know, we won't have those arguments anymore. Part of that is true. You won't have the arguments over that

Ryan Rutan: over money, right? Yeah. Anything that was directly related to, but in the same way that we talk about, you know, we have a lot of early stage folks come to us saying like they want to raise funds and we're like, hey sparky, you might want to dry the ink on the cocktail napkin with the idea on it before we move into the fundraising phase. But hold that thought for a second because they assume that just taking on that money is going to solve all their problems and it's just not, it's going to solve the ones that are specifically related to. I need cash to pay someone for something that I understand is going to help my business right now, which is actually very few things, right? It's mostly the unknowns that caused these issues. It's not the lack of cash now having more money makes some of those problems easier for sure. Don't get me wrong. But it's not like it's the magic cure.

Wil Schroter: Not having it again has very specific challenges and outcomes that everybody is more than aware of, right? That's not hard to figure out. And so I think where we get stuck though is we're so incredibly distracted by money all of the time or the lack thereof, right? Because most life problems have a dollar figure attached to them, right? More specifically, the life problems that you can't afford. Not only have a dollar figure attached to them, they have a timeline attached to them. For example, if I'm super hungry right now and the problem is hunger. I can feel my tummy, but I can't go to the store and buy food, right, Well then money is my problem, right? But if I can't afford to go to the store and buy food, I'm so hungry, right hasn't changed the fact that I'm hungry. And the only thing that changes the fact that I can solve the problem now, the differences for folks that are on the wrong side of this equation, which is most of the world, that's why I think this is such a salient topic. The idea is that, look, every problem that's sitting in front of me again has a dollar figure attached to it. You know, there's a mortgage, I can't afford their startup costs, I can't afford you name it, there's all the health problems, you name it. And so if I had the cash, then those problems will go away and therefore all the things that make me unhappy conversely will go away and I'll be able to do ship that does make me happy, right? And and this is where it starts to get into a slippery slope. Money doesn't allow us to buy happiness and we'll get into that, but it does allow us to make pain go away, which isn't the same thing back to my bruise analogy, you know what I mean?

Ryan Rutan: Yeah, well, when I first started back to jiu jitsu soccer and yoga all in a two week period, which was not a bright move and immediately flared up my knee, I had to wait six weeks for that pain to go away before I could start doing the things I want to do. So pain can get in the way of achieving the things that you want to. But we have to be really careful about drawing lines of correlation versus causation. I know you and I both have personal stories and we have stories of founder friends who assumed that once the money event happened, that all of a sudden the problems would go away and therefore happiness would appear. It's that second part. That's not necessarily true. You now have the ability maybe the time, maybe the resources to go and do those things that you believe will make you happy. We spent an episode on this world, but that's often not validated at all. These are things that people assume they're gonna like, they're like, I am gonna take up sailing once I saw my company, that's gonna make me super happy. Cool. When was the last time you sailed?

Wil Schroter: Never you might want to

Ryan Rutan: try it out before you set your entire life's compass to achieving something that you believe will make you happy that you've never actually tried

Wil Schroter: before. I also have to say this not having money. And again, I've kind of lived on both extremes of this continuum. Not having money prevents you from ever doing those things right? So, you know, maybe that is what you want to be doing with your time or at least you believe you want to be. But if you're constantly reminded and by way of that prevented from ever doing it, you never really get to a point where you're like, well, let me actually try it now. Imagine this. Imagine everyone could have one year where money wasn't an issue and they had the opportunity to just explore all of their interests, right? And all the things they said they were going to do with money for an entire year.

Ryan Rutan: I feel like this was an 80s movie. I think there's a training video for this.

Wil Schroter: Oh yeah, this is somehow has either Anthony Michael Hall or, and so I guess when folks would go through that exercise, here's what would happen, they would go do all the stuff they've ever want to do their vacation. And by the way, this is of course a metaphor for like when somebody sells a company and kind of, you know, has cash coming in overnight, they go do all of that stuff. And invariably every single time they only come back to all the same stuff. All the same issues, all the same ship that they had prior to money. Just without the money problems. Right? So that couple that was arguing, they're still arguing after money problems. They're just arguing over other stuff because money, when you don't have it debt, let's say distracts you. But money doesn't fix you. And I think that's the part because nobody gets tested until after they have it. They never really understand why that's the case.

Ryan Rutan: So I want to back up on something there, which is that you said that you know, nobody has this opportunity. If you don't have money, don't have the opportunity to test these things. I'm going to disagree just a little bit there because you do have the opportunity to try things. You don't have the opportunity to buy your own sailboat and sail it for a year, right? You don't have that opportunity, but you do have the opportunity to get on one, right, go try it, go do some of these things. And I think, you know, we've done an entire episode on this to talking about happiness deferred and just saying like, I'm just gonna wait to try and do all of these little things that I believe will make me happy until the other day where you know, it's all more possible, right? And I think this is, it's an interesting founder characteristic right? In the same way that it's like, hey, I could go join a company that's building something similar to X. Y. Z. No, I'm gonna go build it myself because I have my own way that I want to do this. We're kind of all or nothing. People sometimes to our own detriment, which is like, well I'm not gonna go right on somebody else's stupid sailboat. I'm gonna get my own and I'm not gonna try it until that point, right? I'm just using the sailboat as a metaphor here. But I do see this a lot, particularly just the life deferment and it makes me really truly sad to watch people who I know have enough time to go and do things and they're just not, I have a founder friend who seems to be constantly jumping from one thing to another. He has one stable business and he spends a lot of time Trying to start 2nd, 3rd, 4th 5th businesses while simultaneously complaining that he doesn't have enough time with his kids or that he doesn't have time to work out or do these other things and going, man, like how are you not able to see this when a lot of people around you pointing this out, like you're chasing this exit, you're trying to get something more scalable than the stable business that you have, which very well could provide you a good lifestyle, could eliminate debt, could do a lot of things, but instead he's plowing that into trying to grow something bigger better more. And there's a whole lot to unpack in that scenario. But it still speaks to that same need that you're talking about, which is like that we've got to get to this end. And then that's the thing that unlocks all of the doors, right? It eliminates the pain, but it also turns on the happiness and it's just,

Wil Schroter: it's just not true. It isn't and having been through this myself when I've kind of gone through this evolution where I've gone from, you know, again, growing up very poor, not be able to afford food type poor and getting to the point where I just assumed that being on the other side of that was going to solve a lot of problems and it did, it solved a ton of problems, it solved that food problem we dealt with, it solved a lot of the dumb kind of problems you can just write a check for, you can make go away,

Ryan Rutan: right? It's as simple as it needed to be paid for. Now it's paid end of story, there's

Wil Schroter: nothing else to it. But you said something about sailing. The thought was really interesting that you can go rent that experience and I think this is another fallacy and kind of people and how they look at it. There were a handful of things that I did when I started to make some money that I always dreamed about doing, right. Like one of the things I dreamt about was having a nice car. I think it's a pretty common dream, right? And I was so pumped when I bought my first awesome car, right? It was a Lamborghini, it's an amazing car, right? And I felt like somebody had handed me the keys to a roller coaster right now. It's like so over the moon and considering how responsible I was, that's probably the right now.

Ryan Rutan: It's probably how everybody

Wil Schroter: else felt about it too right? Oh my gosh and so super pumped again. It was something that I never thought in a million years I'd ever get access to. So you know, there's this whole dreams fulfilled but what happened is after a few days of driving it, maybe a week of driving it, it just sort of sat in my garage and remember my friend came over and he's like, oh my God, are you driving this thing all the time? And I'm like, well you sort of can't write unless you have somewhere to be right actually can't drive it that much. And I said it's interesting because not having it was incredibly impactful. Like I just thought about it all the time, I dreamt about it but once I had it and I used it and kind of that thrill was gone. There was never a time where I got in it again or it ever felt nearly as impactful. Sure and it was really visceral lesson that I learned That the things that I thought would make me happier give me that joy unfortunately often didn't recur so not having that car was an amazing thing. Getting it was even more amazing driving. It was even more amazing, but owning it like week to week three, year 10, I forgot about it and think of how big of a delta that is between expectations and reality because our expectation Ryan is that I'm going to get that and man, I'll be driving it every day and every day I'll just be like throwing my hands in the air about how excited I am right because you don't get to test it. Now. Going back to your sailing example, the idea is I can rent a sailboat and I get out there and like you know what, this is amazing. If I have the cash to be able to do this, I would do this all the time wrong. You would do it once, twice, maybe three times and if you decide to become a sailor, maybe all that changes. But you're responding to two things you don't have and again, a lot of it has to do with the fact that you don't have it, number one, you don't have the cash to do it all the time. And number two, more importantly, you don't have the time to do it all the time. And maybe number three, even if you had both, you wouldn't want to do it all the time. That's

Ryan Rutan: the thing. You don't have the experience of doing it all the time, which just takes time, right? You can't validate that part of it right? But you can at least validate actually I get seasick right. I don't thank God because I love being on the water. But if you do get seasick and your dream unvaccinated was to go and make a bunch of money and then buy a sailing yacht, get on it and you find out that you spend the entire time on the thing vomiting over the edge, you're probably going to regret that, right? These are the types of things you want to validate, not, I'm just kidding, I'm using vomiting as a metaphor, but it's like you want to know this stuff before you pin your north star and the direction of your life and your company for at least 10 years, maybe more decades of your life spent on achieving this. You want to know as much about this as you can, right? And this is always funny to me how most entrepreneurs that I know are so curious about so many things, particularly around their businesses, right? They're digging into every little thing and then when you ask them about themselves, they're like, yeah, I haven't really thought about me much ever and they're just not curious about that side of it, right? And I think it's really hard to understand where your happiness lies. It's a bit easier to see where your pain and suffering comes from, right? Because it can be self imposed, but there's typically a third party component to it, right? It could be self imposed in that I bought a million dollar house when I could really only afford a $300,000 house. So that's self imposed, but the third party is the one who's going to incur the pain the bank is gonna come and make me pay for that or throw me out on my duff, right? So to me, you really have to spend some time, some introspection, some curiosity on yourself to understand where any of this goes. And I'm not saying don't go build the business if you can't figure this out, but like don't pin it all on some outcome that you really have no certainty about in either the likely to that outcome happening nor the actual happiness, the fleeting happiness that you're going to get, the satisfaction that will be on the other side of that.

Wil Schroter: I think a big part of that too is kind of separating. I want to get out of debt, right? Who doesn't? I want to get out of debt to make pain go away, right? Which is phenomenal, right? It's a great goal and I'm not knocking that one at all. It's worth everything you think it is. But the other side of it is, but I will become more happy and you know, the title of this was more about, you know, money buy happiness, not, well, money get me out of debt. That's pretty straightforward.

Ryan Rutan: Money will get you out of debt. That is proven fact,

Wil Schroter: but let's just dig into the happiness part a little bit because I want to unpack a little bit more about the kind of the nuance of what people think it is versus what it actually is as it relates to their cash. One of the things that we talked about a moment ago was novelty, how a lot of the things that we want money to do unfortunately have a very short fuse as far as how interesting they are. In other words, let's say that you wanted to go on a vacation to a place you've never been before and you first arrive and you're at a resort, it's a beautiful resort. And the moment you get to that resort, the staff is showing you around and you're just mind blown. You've got this vision of the sea, you've got this great hotel room, you've got all this great stuff and you're just over the moon a couple of days ago by your around the resort, you're having dinner there, everything's going amazingly. But by about day 468, you name whatever your threshold is, you're like, okay, I've seen this ocean enough times, right? Like I'm actually yearning to go back to where I just came from and it has nothing to do with where you just came from. My wife and I just went on a vacation to florida actually and the weather was amazing and back in Ohio, the weather was horrible and when we got home, the weather was absolutely horrible, right? And it was raining, it was cold, it was disgusting and we're so glad to be home, which illustrates the fact that there is novelty in most of these things that we describe happiness to be and the challenge with that is that no matter how many times we keep trying to buy it, it just slips through our fingers over and over and we don't get that. We don't understand how hard it is to maintain that novelty feeling, which is why in the end, no matter how much stuff we can buy to try to kind of up our novelty happiness again, it's consumerism at its finest. We keep winding up to a place where we start all over again.

Ryan Rutan: Yeah, the bar just moves higher and higher and higher with each purchase.

Wil Schroter: It does and so yeah, you've got to keep, you know, one upping to try to kind of feel that same endorphin rush if you will. But beyond that it just keeps masking the fact that however happy or content or well adjusted you were at the beginning of that purchase, you're the same idiot at the end of that purchase, right? You just have less money at that point.

Ryan Rutan: Maybe a slightly bigger idiot

Wil Schroter: and like my wife and I talked about this a lot because we've lived in different places and we had a couple opportunities where we've tried to like live in our dream home if you will or a dream location, et cetera. And so we'd move and we'd have all this fanfare about doing it right and I would get there and at first just like the vacation, it was awesome. Right? But it's all these new attractions and everything was amazing. But then after a few months, maybe a year, we're back to doing the same stuff we were always doing, we're sitting home watching netflix right, in an overpriced house, in a part of the country we probably shouldn't have been in. And we started to realize that no matter how much we kept trying to like buy that happiness back, we'd always rubber band to where we started. Sure

Ryan Rutan: at the end of the day, you're still the same people, you're going to enjoy the same things Now, if there are things that you just simply haven't been exposed to, maybe you do discover something new. But you know, I think the further you get in life, the less likelihood that is that you're just going to discover this brand new shiny thing that's like, oh, this was the key to my eternal happiness. I wish that existed.

Wil Schroter: What you're implying there too is, you know, the money isn't necessarily buying the happiness that's buying your freedom from pain. And yeah, nothing wrong with that. But if you really dig into it and I don't think enough founders do this, but if you really dig into it and start to say, okay, how many things could I use this money for that would actually not just make me elated for a moment, but could sustain happiness give you some examples. I love playing sports. I love playing hockey specifically and when I'm playing it is awesome. Tomorrow I'm going to play for maybe an hour and a half with my friends and I'm gonna be so excited about it. However, to play this out, you're gonna stay cool, you get to do it for eight hours tomorrow and not my body couldn't possibly, I would

Ryan Rutan: say I can't wait to talk to you on thursday.

Wil Schroter: Yeah, that would be the last time I played, but okay, well I wouldn't want to play for eight hours, maybe play for four awesome and you can play the next day and the next day and the next day after maybe a week. And I don't even know if it goes that long. I'm like, dude, I'm kind of tired of playing hockey. Point being, it makes me super happy when I play, but it only makes me super happy because I only do it infrequently same as vacation, right? And I think that's where this whole conversation or thought process breaks down. A lot of people don't realize that what makes it special is the fact that you can't always do it, that it has some in frequency.

Ryan Rutan: There's entire tomes on psychology written about this very thing, right? I always think about it is the happiness of pursuit, right? Not the pursuit of happiness, but the happiness of pursuit, which is to say that half of it is getting to that point, it's playing the hockey is fun for sure, right? But it's all the things that you had to do to be able to free up time on a Wednesday in the middle of the day to be able to go and play hockey, right? That's actually part of the happiness, right? It's the pursuit and achievement of being able to do it right? The doing in and of itself certainly drives some endorphins. But to your point, if you were able to do it every day, it starts to lose that component of it. The hockey itself should still be absolutely as fun. But the fact that it's just always available to you take something away and I would argue deposit that this is more likely in the case of a founder than kind of anybody else because again, we're pursuers were chasers were dreamers, we want to go and get the thing that we don't have yet. We want to build the thing that doesn't exist yet. Therefore once it does exist it does lose its luster. And that's true for anybody. But I would say that in the founder community

Wil Schroter: even more so for me when I was building my first company, you know, starting from nothing. So as it grew, I'm thinking to myself, there is just the shangri la other side of this journey where if I can get to that part of the journey all of the ship that I'm dealing with now, you know, just think of like getting customers HR issues you name it just the nature of building a company once we hit a certain size we'll be able to hire enough people to go address all those issues right? Well higher management management will be just these great people that solve all these issues for me. And so I thought when I got on the other side all the things that were bothering me would go away and so I got on the other side,

Ryan Rutan: it turns out one of the things that bothers us most as managers.

Wil Schroter: Oh yeah exactly. And so when I got on the other side I was so disappointed, I was proud that we got there. But I was disappointed that all my assumptions with getting there were mostly proven wrong. For example one of my assumptions was that I would feel incredibly validated right? You know starting from nothing is very invalidating if you feel like sh it and then as the thing starts to grow and take form and kind of become successful by whatever metric that you'll be validated and there is some of that I don't want to discount that altogether. It's just not quite as much as you think it would be right,

Ryan Rutan: particularly you're looking from third party right? If you're looking for third party validation it's tough because there's only a few people in the world who have been through what you've been through and none of them have been exactly through what you've been through. and so nobody really knows they look at it and you know it's funny and I think we have talked about this before but rather than getting validation from a lot of people, you get the opposite right, you get some jealousy or you get people trying to kind of pick apart what you did and make it sound like less than it is, which is exactly the opposite of validation and exactly the opposite of what you were hoping for and needed in that moment. So yeah, that's not really waiting on the

Wil Schroter: other side for you. Well you know I thought about it like this if there was a scale from 1 to 10 and then zero to negative 10 And how I was feeling at the beginning as far as call it happiness slash validation. And the journey with the first company was clearly negative 10. Everything everything sucked. I was totally broke right and had zero validation when things went the other way and the company took off I did hit a 10 invalidation. The difference is I hit it for like nine seconds right? And then it went down to like a two or whatever it kind of leveled off at, I just assumed if you were super broke and um validated and you're at negative 10 then once you hit that threshold you'd go to the other side and every day you'd be doing cart wheels to your own success, high five to me, high five to me and you get a few fleeting moments like that, but then they go away and then you're going, what the hell? Like this was supposed to be something that was so pent ultimate in my career and I've worked so hard to get here, but now I'm here and it just kind of came and went, what happened? Success you and I talked

Ryan Rutan: about this, we were gonna be friends

Wil Schroter: forever into the sunset, right? It just doesn't work that way and it does present to your point, some other challenges, you know, relationship challenges, whatever, but that's here nor there as it relates to this discussion, right? What we're really talking about is my journey kind of ended with being free from pain, right? Right? It was so clear what I needed to get done, it was so clear what that pain was. But really what I totally missed what I think a lot of founders here, you know, really have a hard time conceptualizing is that all we're working toward is to get rid of pain has nothing to do with happiness, right? Let's do with unhappiness but happiness, the things that bring us joy, the things that sustain us, the things that really or what we think is on the other side, actually have nothing to do with cash. That's

Ryan Rutan: a wrap for this episode of the startup therapy podcast. This is Ryan Rutan, on behalf of my partner Wil Schroder and all the startups dot com family thanking you for joining us and we hope you'll continue to join us. Be sure to subscribe, rate and comment on ITunes or wherever you love to listen to startup therapy. You can find all of our episodes at startups dot com slash podcast. If you're looking for more amazing resources to launch or grow your startup, be sure to head to startups dot com and check out startups unlimited. It's everything we have to offer from our online university to our amazing community of experts and founders and even all the tools we've built like biz plan, fungible and launch rock. It's everything a founder needs visit startups dot com slash begin that startups dot com slash b E G I N. You'll thank me

Wil Schroter: later.

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