Startup Therapy Podcast

Episode #9


Ryan Rutan: Yeah. Mhm. What actually happens after we cash out of a startup? Do we really retire on a beach and spend the rest of our days thinking about how we'll never work again or does the opposite happen. Do we regret selling? Do we still feel the same life purpose or are we actually less happy today on the startup therapy podcast? We're going to explore the side of startups that few people ever talk about life after the exit. Hey, this is Ryan Rutan here with my partner Wil Schroder for another episode of the startup Therapy podcast. Look, we all know that there are some really, really nice things that happen when you sell a company freedom, money houses, cars, hobbies, private jets all come to mind. But that isn't the whole story. So will we both have multiple experiences with what life is like post exit. And we're both well aware that it's not always champagne and video games. There's a ton to unpack here. But let's start with something really big and kind of scary, which is what happens to the founders identity when they saw their company.

Wil Schroter: Yeah, I don't think people think about that part. We were thinking about everything leading up to that part. We're thinking about, my God, I've got all these crazy bills. I've got all of this responsibility. I've got all this stress. You know, I've been burning for so long. I just want to get on the other side of this. So we kind of scrambled to get past that horrible, crazy part of our life, but once we do that, we forget that there's some very personal cost that comes with making such a major decision. And Ryan, I know you've been through it. I mean, you've seen this firsthand what it's like to sell something and lose your identity over it.

Ryan Rutan: Yeah. All of a sudden you're in this existential vacuum and you know, it's happened to me with varying varying degrees. The first time I went through, I don't think that my identity was quite as wrapped up. I hadn't poured myself into it in quite the same way. And I also immediately adopted another identity. Immediately afterwards I had an adventure planned. I, I knew the exit was coming with with about six months advance. Um

Wil Schroter: there was a bit of a

Ryan Rutan: turnkey period and so upon exit, I was able to then roll into this new identity of traveling Ryan and I immediately took off did some world explorations and some other fun stuff 6, 7 years later when, when I had start another company and then sold that I didn't have anything happen immediately after I had already kind of done some of the stuff that you'd expect to do right after selling the first time I sold a company. And so this time it was just like holy sh it, I really don't have a plan. I don't know what I'm gonna do and my entire life and identity was wrapped up in what I had been doing for the previous four years. And so I was just completely at odds with my own existence at that point. And I'm sure your story is probably fairly similar.

Wil Schroter: Yeah, I mean, I actually keep hearing this story over and over in the last year And talking to founders of the three stories come to mind and one guy that sold his company and took about $1 million dollars off the table, Another guy that sold his company and took about $15 million dollars off the table. Another guy that sold his company and took about $300 million dollars off the table. And I'm I'm thinking about their three particular stories right now and how unprompted as we discuss these things, I like to spend a lot of time with founders kind of doing a back story to talk about how to go. You know, we're looking back, it's it's post sale. How did the whole experience go? And in each of their cases, they keep talking about how it was weird that the day they sold it, they show up the next day and like, nothing's the same anymore, right? Like there was supposed to be this massive kind of celebration when in fact, there was, you know, there's the headlines and everything else like that. But the other thing that happened is they walked into work the next day and a lot of them were still part of the business and it wasn't theirs anymore, right? You know, there's this very odd thing where every part of this, every risk, every outcome, every person that works, there was an extension of you, not to be egotistical about it, but if you just put everything you had into it and now it's not you anymore and it happens in one day, it's crazy to see,

Ryan Rutan: it's not yours and it is someone else's. It's the analogy is one of the analogies we've used before is that it's like selling your house to somebody and then living there with them, right? It's pretty weird because you just, you know, you you can separate yourself from certain aspects of it, right? You can sort of start to make peace with the idea that somebody is going to take this thing for, but like for the right there and now there's some very weird situations that arise decisions that you would normally make without thinking twice that are now somebody else is to make. And just like watching all that happen. And again, when, when your identity is tied up in that it's personal, right? This isn't just a, oh, let's see how this chess game plays out. This is you still haven't extracted yourself from the business at that point. And so you're really feeling these decisions in a personal way, not, not in just a practical abstract, this is just business kind of way.

Wil Schroter: Yeah, it's a bit of if you if you stick around, it's a bit of an out of body experience, right? Because you're showing up and like you said, and everyone's saying, oh, hey, you know, it's great that we sold the company, but everyone else is saying, well, what's your role in all this? Well, I'm still the Ceo or I'm still, you know, the VP or wherever I am in the organization and they realized in a minute that you're not the guy anymore, you're a guy, but you're not the guy. And if you've been living your entire career at this company as the guy and every decision is directly impacted by you to you. Not having that is this bizarre kind of netherworld where it is, people generally don't like to live for very long.

Ryan Rutan: That's right. Yeah. You want to get out of that phase as quickly as you can see somebody in a conversation once asked me if it felt a bit like being a lame duck president. And my answer was no, I understood why they were thinking that because there are some parallels there. But the reason that I said no was that the president identity isn't completely tied up with the country, right? It's part of it, right? And then they take on that persona for a couple of years, but they didn't build the country, right? Maybe George Washington felt this way when, when he was when he was a lame duck, although I'm sure he was never a lame duck, right? And so that was where it broke for me. And I said, look like it's, there's a big difference when you're, you've been the driving force behind something since its inception and, and now it's no longer yours. And so yeah,

Wil Schroter: and so we don't talk about that in general, right? Founders don't talk about post exit, I lost my identity, everything was tied up into this company and now I feel disconnected. But you see it implicitly watch the trajectory of a founder post sale. Right? How many founders post sales stick with that company forever. Now? It does happen, but it's so incredibly rare and why is that? Well, there's a lot of reasons. Usually it's because there's no more financial upside. You've already sold all your upside, but the other pieces, you just don't feel whole again. And the problem for founders is as they're considering a sale, even if they're not going through the sale process, If they're thinking about selling, they don't really come to terms with what it would mean to wake up tomorrow and nothing's about you anymore. Now, part of you could say, well, hey, that's okay. You know, again, I'm not that egotistical, I'm not that selfish. I wouldn't mind things not being about me, people can get off my back for a while, but try it, try waking up the next day and having nothing b about you write all of the emails that you were getting were you thought were annoying. People wanted to schedule meetings with you or vendors wanted to take you to dinner and try to schmooze you for their business? All of a sudden no one gives a shit about you

Ryan Rutan: anymore. Before we move on, I want to unpack something more about this, this notion of the startups, identity and the founders identity being being so enmeshed that they're inseparable because I think that we could make a case. I've already mentally made a case. I want to put it out there. That this self is the business. The business is the self Is perhaps a misidentification or maybe um al identification ride with me here for a minute. I agree that it's 100% true that if we define ourselves by what we have and then we sell it. There were also sort of selling who we are, right? We end up long on net worth and short on self worth.

Wil Schroter: And I'm not just splitting hairs here.

Ryan Rutan: I've got a counterproposal. I'd love to see us change the narrative a bit, change our perspective a bit and remind ourselves that our self worth as founders, even if we want to allow that business to temporarily reflect it isn't that the business was the thing of value. The thing of value was within us to begin with, it enabled us to build the damn thing in the first place, right? None of that goes away in the transaction. Not in reality. And so instead of hanging the our identity on the hook of what we have, why don't we instead base it on how undeniably fucking awesome we are to have gotten

Wil Schroter: there in the first place, right? It's it's it's hard though because we know that we got it there either explicitly or implicitly, but all of a sudden we we turned that ability into a thing right into a trophy, into this amazing living, breathing organism. And now that thing that we spend all of our time building feels gone. Right. And so I think that messes with us a bit right? I agree with what you're saying that that you have to you have to say that I'm really the thing and the company was just an outgrowth of that. But boy, that's hard to actually feel it is.

Ryan Rutan: It is. And I'm saying that like the typical narrative is the one that we've just discussed. I would just love to see and give founders permission to think of it in that way. Instead think of it as you know, you were the power behind this thing. Yes. With the help of a lot of the people and whatever, but you don't have, you didn't you didn't sell yourself the day you sold your company, even if it feels like that way try to take a step back, try to gain some perspective and of course that's really hard to do. And right before I interrupted you. I think you were getting ready to make the point that like part of this is that we just stopped being as important or relevant on the day to day, particularly if you're still within that same company, if you're now living in somebody else's house, I think that's, it's a huge challenge.

Wil Schroter: Yeah, and I mean, I always think about it like the actual day after the president is no longer the president, 24 hours ago, you could nuke a country, just a guy that pays taxes like everybody else right with, with a bit more secret service attached to you, right? Like exactly, it's this weird transformation and I think for folks that are used to having you really, you know, such a big role in such a big title, in such a big steak, in a single entity to have all that pulled away overnight doesn't feel as awesome as people think it might, right? Like they think, oh well you get all of the stress off your shoulders and you do, But it comes with all of the feeling of responsibility and feeling like when you were able to influence something that became such a big part of you and maybe the closest connection I could make was apparent with an empty nester, right? It's like the kid going off to college yesterday, you were involved in every bit of their well being and you've spent the past 18 years doing nothing, but making sure that they were okay and then they leave and all of a sudden you're like wow, like that was such a big part of my life that just disappeared,

Ryan Rutan: yep, now I'm just there to fund the meal plan and be prepared with bail money.

Wil Schroter: Exactly right. And I think that for the for the founders when we think about this this post sale Bliss again, we think about the money, we think about all the things that you know will buy with with our post sale Bliss. We think of the stress off our shoulders, we don't really come to terms or take an honest inventory of what we lost because we haven't lost it yet. The moment we do it becomes all consuming, it becomes painful

Ryan Rutan: agreed agreed. So let's talk a bit about all the things that do happen. So these like the some of the some of the things that we think are positive, right? One of these things is that kind of would like go out and spend some money, we buy some stuff running around like remember the you know the the sweepstakes when we were kids will where you could win the run through toys R us,

Wil Schroter: right? And you could just

Ryan Rutan: load the shopping cart right? Like just so that's what I picture right? Like I guess what everybody pictures like that the day after sale there's a founder running through whatever his grown up version or her grown up version of toys r us is just shoving stuff into carts going as fast and as crazy as they can. But I think we've we've both felt this too. Like you just kind of there's something just ran out of things to buy like it, there's a depression, there's a diminishing return on like just going and spending money because you now have it.

Wil Schroter: Yeah. And I would say the same thing I said in my own experiences and seeing the same experiences with others. The value of anything is the fact that you don't have it right the moment you do, it's the value equation changes dramatically, which is why you generally don't hear people say, well, when I was a kid, all I wanted was G I joes. Now I have G I joes, I'm golden for life. It doesn't work that way, right? Life doesn't work that way. And yet, no matter how many times we learned that lesson, we failed to do anything with that knowledge, no matter how many times we accomplish the things we set out to accomplish, we keep getting reset back to wanting more. Now, some people are super zen right, and figure it all out and can live a very bohemian lifestyle. They're often not the founders trying to grow and scale and sell companies.

Ryan Rutan: So that's it's an interesting point. And this was this was a distinction that I drew for myself a few months ago I sat down and I said, what's the difference between happiness and satisfaction and what it came down to for me was that happiness was the pursuit I was happiest when I was pursuing when I was chasing and I was in the dream and I was trying to get to the thing satisfaction was when I had actually gotten that thing. And for me, satisfaction is, is on a lower, it's a lower ranking outcome than happiness. Right? So I'd rather be happy than satisfied. And so that was really what it came down to think that like to your point, like I'm happy when I'm thinking about doing something, I'm happy when I'm planning the move to the new house and I'm planning on having the bigger yard and the bigger house and the bigger pool. And then I get it and I'm satisfied with it. But the reason that turns from happiness satisfaction sometimes, like it also adds some liability and I got a bigger long demo, it takes twice as long to clean the pool. So some of this stuff isn't nearly as fun after the fact as it is to just kind of to dream it up. Right. And so I think that's, that's also a fairly common outcome for folks,

Wil Schroter: Those things have a very short lived payback period, right? If you've never owned a home the moment you own the home and you move it is awesome, right? Pure elation elation. And then every year thereafter it drops from an asset to a liability right now, not necessarily financially, although in some cases that's true,

Ryan Rutan: that also happens

Wil Schroter: right? The novelty, like anything else in life wears off and you're back to wanting more. The problem with that is when we hit cash out stage where you know, take a little bit of cash off the table and we by the handfuls of things that we always wanted. We tend to think of it in terms of, well when I get the Ferrari, when I get the big house, when I get the boat, that will pay dividends forever and what we don't think about is they pay huge dividends the day you get them, but within a year you're used to having them. So the R. O. I on that drops dramatically. And so we're thinking, okay, we're gonna take our startup, we're gonna sell it and then get all these things and those things are going to give us the same kind of happiness like you're talking about that, you know, the the same kind of payoff like our startup did on a regular basis and they don't, it's a very short lived victory if you will?

Ryan Rutan: Yeah, I totally agree. And then, and then you start to wonder like, well I got this handful of things, what if I had a bigger handful?

Wil Schroter: Exactly,

Ryan Rutan: right, What, what if I increased the grab that? It was, it was a faster car, what if it was a a fancier house, but it was a bigger boat. And then it comes down to these questions you start asking yourself like did we sell too soon. Was that really the right thing to do? Was it worth it? Did I get enough at the time that I cashed out? This feeds into something else that you and I have talked about a lot, which is then we start to feel this need to one up ourselves,

Wil Schroter: right, no matter what we did, it wasn't good enough, which is so funny, right? Like, yeah, what are the chances you were ever going to do that to begin with? And now all of a sudden within six months in this weird period of your life, it's all of a sudden not good enough. Yeah, right. The answer is 5%, right? 5% of

Ryan Rutan: startups that make it past year one. Uh, there's a 5% chance that they will see some sort of liquid exit liquid being very, very relatively like we'll pay your debts and then we'll take your business right all the way to you, you get a billion dollars and you can bugger off and go do whatever the hell you want

Wil Schroter: because we're entrepreneurs. I think we get this sense that if I sold something for one million, gotta sell the next for 10 million. If I sold it for 10 million, it's got to be 100 million. Like I'm surprised entrepreneurs. I just don't get this one again zen master entrepreneur that says, dude, I sold for $7 million. What does it matter what I do on the next

Ryan Rutan: day. It doesn't matter. No, it's, it's hysterical. We get, we get such like a growth and scale mentality that this applies to things that it absolutely shouldn't like our next exit. You're like, well I need to scale the next one. Like that's complete bullshit. You're going to be lucky, lucky to have the first one. If you get the second one at all, just be really happy, right? Don't worry about scaling it to something else.

Wil Schroter: Also, if you have the ability to get two exits of any capacity. Holy ship, what are the odds of that?

Ryan Rutan: Or somewhere near powerball level.

Wil Schroter: Exactly, right. And so the idea that, well if I sold for one million, the next one has to be for 10 million, like by what math or probability does that actually happen? And I say this because the most common occurrence that I see among founders that cash out is they go to shoot for the moon on the next one and the next one is always a bomb. It's always a bomb, right? And I think a lot of that has to do with, we have these fucked up expectations that since the last one was so big or so good or had an outcome that was positive, I'm entitled to the next one being bigger. And it's like, no, you're not. I mean in this by you, I mean all of us, right? If I build something today, and and we were fortunate enough to exit one. The probability that I'll ever do it again is so incredibly low too. There's no way for me to say it will be bigger or expect it will be bigger because I haven't built it yet. I have to go pretty far along to get there. Yeah,

Ryan Rutan: well, I think you get you get this skewed perspective too, and and and part of that is having been on the other side of this thing. Now, you have a different perspective, You also have a different ability to pay into the startup and so you may not approach it even the same way, right? So in addition to just like not really evaluating the idea in the same way you would, like, you're not forced to like really gut it out and think about like, is this exactly what I want to do? Like, is this the thing that I'm most passionate about, do I really care enough to keep doing this for as long as I now know it takes right? Because at this point you do have that data point. This takes a long damn time, but you don't have to go through. You don't have to go through as many of those machinations because you can fast forward some of these processes arguably right off a cliff because you've got some cash in hand now, things that you couldn't have afforded to do before you can now waste your money on because you got it to waste.

Wil Schroter: Absolutely. And let's face it, you're also sitting around the house bored out of your goddamn mind, like nobody thinks about that part. Nobody thinks about, okay, well if I cash out, What do I do the next day and everything is the same thing. Like I'm going to read a bunch of books, I'm going to take some vacations. I'm gonna do all the things more or less. I couldn't do, you know when I was working my ass off for the past 5 to 10 years, shave, shave like basic hygiene, right? Um, you know, we're all going to lose weight. You know, we're all gonna have ripped abs or you know, whatever our, our, our goals are and you're thinking to yourself, okay, cool. For how long, how long are we going to be taking vacations, reading books or whatever before we are just straight up board. Her mind's right.

Ryan Rutan: I was going bonkers. I think that was when I talked about, you know, the tale of two exits. The second one for me and it was far less glamorous, Right? This was a, this was a very like kind of run of the mill business wasn't for me, but you know, it was a cafe, right? This was not technology that wasn't highly scalable. It was a cafe and I built this thing, I spent four years in it operating it and then and then I sold it. And the difference between that and my technology company was that it demanded of my time in a way that nothing short of my three Children and marriage have since

Wil Schroter: of course

Ryan Rutan: it told me when I had to be there. Whereas like within the tech companies like you kind of you apply pressure when you want to, you've got you know of course you you have to do what the business needs. But there was much more self determinism in that business and there wasn't a cafe cafe like I gotta be there at five o'clock so that the machines are hot by the time people start showing up in want coffee. And so it controlled my schedule for a long time when that all of a sudden went away. I had such a frame of reference for how little time I had prior to that day. And there was no turnkey with that one. It was just one day I was there gotta check next day I was gone and I was bored within a week. I was I was questioning my existence. I had more sleepless nights post that exit than I did in any of the company I had built before or since. I spent more nights staring at the ceiling going, what am I gonna do, what am I gonna do? What am I gonna do? Not? I don't know how I'm gonna make payroll. It's like I don't have a payroll to make what, why do I exist? What happened? Right, So I was, I was super bored and super scared and I started going batshit nuts.

Wil Schroter: And I think everybody does. I think because what we don't think about is this job we just had a minute ago Consume 10-16 hours of our day for years. The moment we don't have that job, we still have 10-16 hours a day. That is a long time right to fill with empty hours.

Ryan Rutan: They weren't releasing video games fast enough to keep up with me. I'm like, I've got more time than you people can produce. I can only play through this so many times. I've seen all six of the alternate endings to this game needs something new.

Wil Schroter: And and here's the thing, It's the type of people that don't like to be bored for 10-16 hours a day. Right? 10,

Ryan Rutan: 10 to 10 to 16 minutes did you say?

Wil Schroter: Yeah. Right. Right, right. And there's a point at which you're thinking yourself, I have to find something not only to do to keep myself occupied to engage my mind. I need I need that thrill again. Right. I need to be pumped up and so inevitably what we try to do is we try to come up with another startup to fill the void of the last startup, which is so funny because we just hit the reset button and do the same damn thing all over again because at the end of the day, what we enjoyed most wasn't the startup, wasn't the exit, wasn't any of that bullshit. It was the challenge. And you can't take challenge off the plate of highly motivated people and expect a new car or a nice house to fit that bill. It doesn't, it's not even close. And so we all run for the next shiny thing.

Ryan Rutan: We do, we need, we need that resistance, we need that pressure, We need that challenge. We become addicted to it. There's a similar phenomenon and, and I'm not going to pretend that I've had to put my life on the line for any of my companies in the same way. But they talk about the same thing upon returning from a theater of war. You get so used to the stress and the adrenaline and and all of these other factors that just omnipresent you just, they're always there and then all of a sudden they're all gone and it completely warps your reality and you just don't know what to do. And so that's why you see folks are like, well yeah, I finished my four years and then then I re upped and I, by the way I requested to go back into a theater of war, which to somebody who's never been myself included completely doesn't understand, I have some proxy of understanding because I've done the same thing in a in a much safer way, right? Like my life hasn't been at risk in the same way that our troops put themselves at risk. But you have the same sense of like I need to go back in, I need to be there, it needs me as much as I need it. So I'm going to go

Wil Schroter: right. Exactly. And I think from, from an entrepreneur stand point, the moment we start to say, oh man, I need to come up with another startup idea quickly. I guarantee it's the dumbest

Ryan Rutan: idea you've ever come up like that's always a great recipe for like, let me just come up with something the next 15 minutes and run with it. It'll probably be good enough every single

Wil Schroter: time for disaster. I get an email from one of my buddies and they say, hey man, I've got to get together with you, we have to talk about this new thing I'm working on and I just look at the calendar from the last time they sold or exited. All I can think and I hope otherwise, but all I can think is this is gonna be the dumbest fucking idea I've ever heard, right? And I'm talking about for some of the most amazing dynamic founders. I'm also going to include myself, right? Like if I, if I look at my history of dumbest ideas, they came on the heels of my best ideas every single time

Ryan Rutan: it's the vacuum and that's the balance of the universe, right? You're like, this one was great, therefore this next one is going to be something you'll regret ever having talked out loud about.

Wil Schroter: I I think the reason is because you had years and sometimes your whole life to have all of the stars align in a certain way. That led you to the first opportunity that worked out, right? And you might have had some failures that also led up to that. But all of those things became the fabric and texture. That was what led to this great idea. Now you have none of that. You have all things that don't work in your favor, you have too much money ergo, you have so much friction or you have no friction rather to doing what you want to do, you have all the time in the world to sit around and think, But not always to experience, right? Like if I worked in a bank for 15 years and dealt with all the crazy bullshit that come, with came with working with the bank and from that came up with the inspiration for a banking style product, then that makes sense because I've been kind of going through the trenches this entire time. If I've spent six months screwing around the internet, reading feeds and binge watching netflix, and that's where I came up with the inspiration from my idea, it just isn't the same. And the problem is not only do we not have the same catharsis that got us there, we also have this artificial acceleration that says I have to get back on the horse, I have to be relevant again, I have to be not bored again, I have to have purpose again. So we're running to it for the wrong reasons and that tends to generate the wrong idea,

Ryan Rutan: you know, for sure. And if anybody out there listening is getting worried about the idea like you've got an exit coming or you've exit and you're like, but I only have good ideas, don't worry because after you sell lots of people who have really shitty ideas will also come and talk to you and give you their ideas. So if you feel like there's going to be any kind of a drought around bad things to spend your time on, they will show up at your door in droves.

Wil Schroter: You see this all the time, there's, there's nothing more painful than the entrepreneur that has too much time on their hands, right? Where they have some money. Yeah, Oh my God, just looking for something to get into. It also tends to be what makes people really shitty angel investors, right? Well, I've got

Ryan Rutan: a very specific point on that one and it's, it's, it's, it's post exit angel guilt, right? Which is to say that like I made some money by doing something really good. I spend a lot of time in this now, I've got people coming to me and I can see that they're passionate. I can see they really want to do this. I can put blinders on as to whether they have a clue or not. I want to help them. I want to help them because I want to help people, right? You want to help people. You want to send the elevator back down. And unfortunately sometimes we send the elevator back down loaded with cash to somebody that has no idea which florida get off on the way up. And it's just like that is so painful. And it comes from this like, I don't know if it's guilt. Exactly, or like a desire to help, but it's usually really misguided.

Wil Schroter: Yeah, it comes from the right place. But in all fairness, gifted angel investors tend to be gifted investors, they tend to be really good at the job of investing. The problem with investing is the only requirement in order to become an investor is to write a check. Right? So, so long as you're willing to write a check, you can consider yourself an angel investor doesn't mean you're any good at it, Right? And that's, and that's the same problem with all of the opportunities to a post exit founder. They have time and they have money, which can theoretically qualify you for all kinds of stuff. Your next startup idea. Getting involved with another startup writing angel investment checks, but it doesn't mean you're actually qualified. You just have nothing to do that's different. You're,

Ryan Rutan: you have the opportunity, not necessarily the capability.

Wil Schroter: And after a while after sitting around bored for long enough after kind of playing with different ideas, after making what almost are always shitty angel investments, you all of a sudden find yourself lost. Right? And and and and what I find more than anything is that cashed out founders all battled depression right now. I'm sure there's some that haven't, so, you know, I don't want to make a blanket blanket statement. But boy, I've had this conversation hundreds of times with folks of all ends of the spectrum as far as who's cashed out and their lives thereafter. And if I were to point to one common thread, it's will I'm fucking depressed man. And, and I, I

Ryan Rutan: remember remember I'm laughing not because it's a funny topic at all, but you said something hysterical to me once, which is that you were recalling a point in time where you had finished like your umpteenth day of binge watching netflix in a bathrobe that reeked of cheetos gimlets and body odor, right? Which I know isn't necessarily in the handbook around clinical depression, but I'd say it's a pretty good indicator.

Wil Schroter: Well, look, man, at some point, there's nothing to do, right? You want to get suited up for the big game and there's no game. And it's not just that, you know, it's part of, it's okay. You know, I want to get back in the game, etcetera, but there's a lot of stuff that folks don't think about when they have too much time on their hands. For example, all of my friends have to go to work. I don't, that sounds awesome until you actually want to do something. Yeah. Yeah. The only people that are, yeah, the only people that are living your life are drawing retirement. You know, I'm seriously and you all of a sudden get this weird identity crisis that you envy your friends that have something to go and do tomorrow.

Ryan Rutan: Yeah. You look at them, you know, you have purpose. Even if they don't love the purpose that they have, they still have one, right? It's like if you don't have a car and you see somebody else that has a car and you're like, well, it's a beater still goes forward backward left and right, which is better than what I've got right now. Like I just don't know where I'm going. I don't know what I'm doing

Wil Schroter: in the counter to that would be, well, look, man, if I'm gonna depressed, I'd love to have a ton of money. I won't disagree with that, right? Look if if if you're

Ryan Rutan: gonna be, it's a nice way to dry your tears, right? And pulls the cash great way to

Wil Schroter: dry tears. However, what I'm saying is that having the cash doesn't necessarily prevent the depression, right? And so I know there's founders that are probably gonna hear this, there's actually founders that are probably dealing with this right now. And I think it's important to point out you're not alone, right? If you're feeling anxious post exit, if you're feeling depressed, in some cases, if you're feeling lonely, I would argue that that's the 90% outcome now. That doesn't make it necessarily better for you. You're not alone. And I think because of that, we've got a hard time talking about it, right? Think about this, you cash out, you've got a little bit of cash in the bank and I'm not talking about billions cash out. Just even a modest cash out, right? Whatever that is to you. And a couple of months ago by just trying to get a little bit anxious, a little bit bored. A couple more months go by, you start to get a bit depressed, you start to worry a little bit about again, your identity, your reason for getting up in the morning, etcetera. Who do you talk to about that? Right? Which one of your buddies who's working 10-16 hours a day, drawing a check. That's nowhere near what you've cashed out on is going to feel sorry for your woes of having to play xbox All Day, right?

Ryan Rutan: Let's do a quick poll. Which one of my friends would love to hear a tone deaf argument about how hard it is to be me with so much money and and so much time and just so little to do with myself, right? Like nobody wants to be that friend,

Wil Schroter: which is where that compounds because now all of a sudden you feel guilty about your success, right? And again, this, this is where founders start to get a little depressed too because they're lonely. They literally have no peers anymore, right? There's nobody that can spend time with. They can't complain about a very real issue that they're dealing with. And now it's, it sounds like a gift. It's, it's sort of not now, you can always give the money away and solve that problem, but short of that, being able to say, hey, you're just raising your hand. Look man, I'm not complaining about money about life. I feel fortunate I'm just really lonely now. Right? It becomes a very real thing. And I think the stigma of feeling like you can't talk about it, you can't express it because all of it sounds like either entitlement and or you know, a self serving nature is bullshit. I will say this, what I've found is the most understanding folks in this space are their founders, right? There are other people, even if they haven't gone through it, even if they haven't sold, they can understand they can identify with what that loss of identity must look like.

Ryan Rutan: They can imagine it at least, right? They may not be able to be empathetic, but they can at least sympathize with with where you are, how you got there. And I think that they because they can see it in themselves, that they can understand. Yeah, man, if all of this just went away, even if it was replaced with cash and and wealth and time, that that would be weird. Whereas I think somebody who's in a corporate environment or you know, a lifelong, you know, kind of job for somebody who's just always kind of taken direction from somebody else and and done done nothing to earn their paycheck. If somebody were to say like, yeah, I'm going to take away your your 9-5 and hand you cash and time. Um and theoretical freedom. They think they were getting the deal of the century and and and maybe they wouldn't have the same feeling on the back end. Um I'd argue that people who have won the lottery sort of proved that it does also happen to them. But uh people kind of go off the rails.

Wil Schroter: Yeah. And I think what happens is people get to the point where they're saying, man again, the startup is stressful or there's just other stuff I want to do, right? I've got hobbies that I want to do, I've got I want to spend more time with more people and and all of those things are wonderful, but they're not necessarily the same as having core purpose, right? And again, I don't want to compare your business startup core purpose to like your core purpose with your family. These are totally different, right? And you don't need to sell your business in order to get purpose with your family. But when you take away a person's passion, what they worked on their craft, the core of what they create and you pull that out entirely and replace it with money. It rarely feels like a fair switch and it's rarely something where when you drop in the money all of a sudden you're like, well, okay, I guess I don't need purpose anymore. Yes, The people don't put together.

Ryan Rutan: It's it's not a trade that

Wil Schroter: works right. I

Ryan Rutan: think if you look at the the hierarchy of needs, there isn't one that you can just sort of instantly replaced with cash and and it's sort of still works right in that, in that hierarchy of needs, you still need all of those things leading up to self actualization, um, to feel really, really, you know good with yourself in this void that that I think a lot of founders run into this this space between your depression and not having anybody to talk about. I see one very particular behavior which is that a lot of startup founders post exit become advisers. Right? It's not quite investors, right? They become advisers. And and I would say that is 100 we're not 100%. It it does serve a purpose, but I would say the initial impetus for doing so is very self serving, right? I may not get to go talk about exactly how I feel, but at least I can go talk about something that I understand with people who will relate to it and I can be helpful, I can be, I can have purpose and I can have meaning. And they start to a day sort of adopt these startup companies they're advising as a proxy for what they sold.

Wil Schroter: Yeah, absolutely. And also they want purpose. They want to be heard. It's it's back that thing where nobody gives a sh it about what I have to say anymore, right? Being an advisor lets you feel important again. You know, your experiences matter, your opinion matters. And I think that's very real and really no shame in it. I mean, it's it's real feeling. But I think that that what happens with a lot of folks is they have this vision for what they want the startup to be. Then they have a vision for what a sale looks like. Then they have a little bit of a vision for what the post sale looks like. But then post sale happens and they realized they had a shitty vision for post sale. Post sale for them. It was just the absence of all the ship that that's in their lives right now, I want the absence of stress, I want I want the feeling of being safe. So, you know, so I want the absence of that insecurity. I want the absence of being told what to do by customers every day. I want the absence of all these things

Ryan Rutan: compare that to the amount of detail that would go into a business plan. And you think your business plan sucked your post business plan really sucked your if you were to make that analogy like the the, the initial points in your business plan, things like I wanted to make money, right? I wanted to work good, right? Exactly. There's not enough detail in this plan and and that's where it starts to fall apart. And then, uh, and we've talked to us a lot, but then what ends up happening next is that there's a reversion in the behavior. And I think that, you know, things like advising or investing are a gateway drug to the final outcome, which is that, you know, we do the one thing that we know and we jump right back in.

Wil Schroter: Yeah, we build another startup because once we sell it, the thing nobody told us about the entire time, kind of what wasn't in the brochure, so to speak, was that the startup would probably give you more purpose than you've ever had in your life. In a way you've never had it before in selling it and getting rid of it and not having it in your life might be one of the most empty things that you'll ever do in your life. And I think that is a huge lesson, that frankly you can only learn once you've actually done it.

Ryan Rutan: I agree completely. I think, and I don't remember it's been a long time since I've seen this movie, but I have to imagine that within a few days of the ending of old yeller that a new puppy showed up at that cabin.

Wil Schroter: That's probably the case. No, that's the thing. And so I think if we were to recap here the glamour around starting a business and selling it is all about that big outcome, that big exit and everything that comes with it, but nobody puts detail about what actually happens post exit, right? And I think once we dig into these things, when you go blow by blow to say, okay, if I were to sell today, What specifically would start getting better in my life again, not the absence of stress, but what's the new thing that selling is going to enable me to do that would allow me to consume 10-16 hours in a way that I'm doing right now in my startups. I would argue most people don't have an answer for that and it's really worth discussing.

Ryan Rutan: It is it is worth discussing that the default answer is exactly what I was doing before I sold,

Wil Schroter: right?

Ryan Rutan: Yeah, right. Well it goes back to the, you know this distinction that I came across, which is that for me, happiness is, is the pursuit and satisfaction is the outcome. And so I think that once you hit that point of satisfaction in the outcome, it wears off after a point and you want to go back to being happy again. And, and so, you know, you dive in, you do the thing over and whether it works out well or not, you're probably happy, at least for a while it's happening.

Wil Schroter: Yeah. And, and at which point you are post sale and you're having those weird feelings where, hey, I don't know what the hell is going on. This is odd. I feel depressed, I feel anxious, I feel lonely. That is the process. It's sad and shitty. Don't get me wrong. But that sort of is the process, right? And, and so, you know, 11 more thing I would point out there is for folks that are feeling that folks that are going through that talk to other founders, I can't emphasize that enough. Hell talk to us, right. You know, and, and express kind of what's going through your head. We've seen it a million times. I mean, we'd love to be able to kind of give you a little bit of feedback as to what other folks are doing to kind of get through it.

Ryan Rutan: That brings us to the end of another startup therapy podcast in the meantime, if you love what we're doing, head over to itunes and subscribe and comment. If you'd like to connect with us directly, we're not hard to reach email therapy at startups dot com will, and I respond to each and every email that comes in, what we shared today is a tiny fraction of the help that you can get from startups dot com. Whether you need to learn how a startup gets built, how to find a mentor or how to raise capital, maybe you want to find new customers or just want to connect with founders who are dealing with the same shit you are. You'll find it on startups dot com with that. Let's get back to building our startups. This is Ryan Rutan for my partner, Wil Schroder and the entire startups dot com community saying goodbye for now, Friends.

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