Startup Therapy Podcast

Episode #154


Ryan Rutan: Welcome back to the episode of the startup therapy podcast. This is Ryan Rutan joined as always by my friend partner and the founder and Ceo of startups dot com Wil schroder and as I'm sometimes joined by a whole room full of other amazing founders. So we've got a whole group here today and we will be calling on the audience at some point, so stick around to the end to hear what everybody has to say about what will and I have to say, Well as founders, we tell ourselves lots and lots of different and funny lies to motivate ourselves to, to keep going. Lots of reasons for these things, mostly well intended. One of the biggest lies that we tell ourselves is all these things we're going to do in retirement and whether retirement comes after a big exit or whether this is just the result of lots of years of compounding tiny winds. The outcomes tend to be kind of similar. We've got this whole list of things we tell ourselves we're going to do, but what's the reality? And didn't you just have a conversation like yesterday or day before with the founder on this very topic, Probably the third one that I think that I've had like in the past week and so yesterday, a good friend of mine just sold his business about six months ago, which would be super happy to see work really hard to put 10 years into it, you know, finally got to the sale etcetera and what we were talking and I was saying this tongue in cheek, I was like, let me guess here are all the things you told yourself that when you're going to do that, we're about to happen. Not you finally got into the exit, right, and went through a laundry list, we'll go through all those today. And he's like, yes, all of those things. And I was like, and how many have you done? He said none of those things, like, and here we go. I was talking to another friend about a week prior to have lunch with as well, also had an exit huge exit in his case. And I said, so it's been a few years now Where you at? And he's like, I haven't done a damn thing. He's like, I've never been bored my entire life, and he's nobody told me retirement was like this. And so this isn't necessarily just about the retirement, where were, you know, 65 plus, and we're retiring. This is really when we retire from this gig from this startup what does it look like on the other side of that curtain? And for us, how much of this is just us bullshitting ourselves the entire time and just making excuses for this, you know, fanciful life that we're going to have, and how much of it actually plays out. So I think that's, you know, kind of what we'll cover today. Nice. So let's dig in, man. What do you wanna talk about first? Which one of the lies you you pick, I'll let you go first. Yeah. Okay. So there is this great blog post that I think has been lost to the interwebs. And this is kind of what made me think about this entire time. There's like 2005. What would have been a blogging site in 2000? I don't even remember. I think they still delivered them to your house along with your with your netflix DVD at that point yet. Anyway, so um this guy in Massachusetts by Boston sold a software company and writes about it and it was this long, long missive About all the things he said he was going to do once he finally sold. I remember he was like 35, so I was pretty young. And uh one of the things he said, he's like, I'm gonna read every book there is I've got a stack of books in the corner and I'm going to read every single one of those right in today's term, I think it would be going through your netflix queue, right? But he's like, I'm going to read every single one of those books blah blah blah. And he's like, you know how many books I've read. None. I've read less books since I sold this thing that I was when I was working. It was total bullshit. 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 start startups dot com and we'll pick it up from there. Yeah, I mean like, and look at some of this stuff doesn't even wait till retirement, right? Like some of this plays out like we can we lie to ourselves even before we get there. I do this to myself. Like every time we're going to have a vacation, I will load up my kindle with books that I fully intend to to read and then I get back and I haven't even touched a single one of them, right? And it's it's amazing. But that's a different problem of course, right? Because I'm not completely in, in a, in a vacuum there where I really don't have anything to do? That's more of an issue of just letting go. But it always makes me wonder like, why am I doing that to myself? Like what is it? Do I need to hear these things do I need to pretend I'm going to do these things. Is it something to look forward to. Is it something to motivate myself and I can never quite put a finger on it, so I'm gonna be interested to kind of pull the audience on this one at some point because I'm quite happy doing what I'm doing, I wake up ready to do this and enjoy doing it. So it's not like I'm trying to live vicariously through actions that I never take, it's not like that, it's like, well, you know, I have to look forward to that, that thing, you know that I'm going to do in order to get through today, it's never like that with me. So I have not put a finger on what the motivations are behind these things, but I do, I have lots of these big weird aspirations and reading is one of them, luckily I do, I do manage to consume some of that now, so I'm not completely deferring that to retirement, but like, what drives it for you though? We'll like, what is it, what, what do you think is behind this? Like, why are we doing this? Here's what I think it is, right? And I don't want to bury all of this, but I think for all of these things and all things we'll talk about, unless we have this idealized version of what we must be like if our startup wasn't just getting in the way, right, I would be doing all these things, I'll give an example, I would be totally shredded if my startup wasn't getting in my way, right? Oh my God, I I'd be at the gym all the time, right? I'd be running in the morning and I'll be working on during the day and I'd be finishing up the day in tennis and yet I bought one of those things, the mirror, right? Which has all the exercises on it. You lost me at mirror. Like that's the worst way to start working out. Are you kidding? I only go to gyms where they have frequent power outages and like, what can we do this with the lights out the last time? I've even used that thing to be fair that I do work out every day, but like, like as little as possible. I hate working out. But that's the point. Yeah. If it weren't the case, I would say, oh, it just must mean I don't have enough time when I get rid of this startup and I have all the time in the world. I love going to the gym, right? It's not my pure aversion to working out. It's time. It's time, right? So I understand why you're lying to yourself about that one. That one makes sense. I get it. Well, and here's the thing while we're doing our startups or doing anything that requires a ton of time. We aren't typically at our healthiest selves. Should we be? Should we make that a priority? Sure, but we're usually not and we believe that there's this future point, we're we're just going to be this this again, idealized version of ourselves, The guy that wrote that blog post that I was talking about, I'll never forget. He specifically said, he said I was 100% convinced that by the time I sold my software startup, that I'd immediately run right to the gym and then from there on I would have Brad Pitt fight club abs for the rest of my life, right? He's like, I'm the fattest I've ever been. Just like this polar opposite. All right. And I think from a founder standpoint, it's easy to pretend all of those things aren't on us. It's easy to pretend all the things happening that are like wrong in our lives right now are our startups full. And that's really a lot of what this is about, it's not so much about retirement per se, right? It's about being able to use your startup as this kind of false proxy for what you actually weren't going to do to begin with is exactly like you said about going on vacation and loading your kindle up with books and at the end of your vacation. I was like, well, I didn't read any of this because you didn't want to read. It's not that fun. Yeah, it's not Yeah, that's the thing. So I think that in some cases, so that some of these become more obvious than area when we talk about things like the reading that's something we can say, like we're trying to do it for self improvement, right? This is going to make me better at running my startup. So it feels like it feels like a thing I should do, right? And I have an excuse built in for doing it, you know, working out being healthy, we know that's important, right? So we want to do that. These are these are things that matter when we get off into some of the other stuff, right? The things that really the startup isn't stopping us from doing like any version of normal life, you know, like the, you know, just I'm going to travel all the time or I'm going to pick up that hobby that that is all consuming because I have nothing else to do with my time. That one's a little more interesting to me, right? Because that really is that far off future state. And so what are we trying to do? Are we trying to continuously tempt ourselves into continuing to do this thing? Because of the promise of this thing that we maybe kind of want to do in the future. Again, I'm going to keep coming back to like, what's motivating us? What's driving us to tell ourselves these lies in the first place. Because if you really pushed me on it and asked me like, you know, what would you be willing to give up to go do that. Like right now, I'd probably be like, I don't actually want to do any of those things that much, right? Like, so again, like what the hell is dragging me to say? Like these things like, okay, here's all my, here's all these perfect future plans I actually not that excited about. They're not exciting because you actually haven't had to do them. The idea of reading all the books that you can see behind me right now, by the way, the Muslims are comic books, but the idea of reading all of those, it sounds awesome, right? I have all the time in the world to read those books if I want to like your to your point, right? I just don't, I keep thinking my startup is somehow holding me back. The biggest one I here of course is that I'd go on vacation. I travel all the time and yet every single founder that I know that has exited and tried that they told me the same exact thing they said, listen, the first vacation is maybe the best vacation I've ever been on because it's the only time I've ever been able to relax in like a decade or longer. You however long your run was second vacation. It's awesome because I now get to go on multiple vacations right? I got to do that twice in a row for the first time, right? I gotta have cake and ice cream. They said by the third vacation, it's the equivalent of taking a bath after you get out of the shower. It's nice, right? But it's kind of useless. Yeah, I had a friend that went through this and, and that was kind of the planet was outpost exit. They set up a world tour over a two year period. I mean they had planned this all out and it was this big thing. We're talking probably 3.5 months into this and I was like, so you guys really enjoying like, what's your favorite spot you've been doing? Look, we've been in some really cool places and I'll tell you about that in a minute. But first I just have to tell you like, I just feel like I'm homeless. That was, that was how he feels like I just feel completely untethered ungrounded. We're actually, we're enjoying parts of it is like, but I just, I feel like we've completely lost center and, and we don't belong anywhere anymore. And so it's really, really unnerving and we're thinking about pulling the plug and they did, they ended up making like another 3.5 months. They also got pregnant. And so I think that that put a little bit of a kibosh on how much moving around they felt like they could do with their second. But yeah, it was not at all. You know, this and they had planned for this, right? This was, you know, leading up, they had almost exited once before. Didn't happen and I remember he was really disappointed because they had plotted out all the places they were going to be post exit, they finally get to do it and it wasn't, it wasn't quite as much fun as they thought it was gonna be. Here's why though, I I think because what happens is when you don't have vacation, it's like anything else in life when you don't have something having, it is extra special for me. When I get to go on vacation, we've got spring break that we're planning now for the, for the family. When I get to go on vacation, I'm tired man, I'm burnt out. Right? So the idea of going somewhere where I'm not tired and burnt out sounds awesome. But what would it feel like if I wasn't tired and burnt out? Right, I look around like this is kind of a small room that I'm cramping with with my, my family and like I've got kind of crappy food. I keep having the same pool every day. Like it's not quite the same thing. And so a big part of what makes vacations special is the fact that you don't get to do it all the time. It's, it's like anything else When you eat first slice of pizza tastes delicious. Second slice of pizza, not so much by the 10th slice, right? You're passed out and it's disgusting. The whole thing is it's enjoyable when you're hungry, not so much when you have it all the time and I think vacation is the same. It sounds like something I would do all the time until you actually do it all the time and it burns off fast. It's no longer a vacation. It's just travel, which isn't quite the same thing. You know what I mean? Yeah, for sure. I think one of the biggest misconceptions is that, you know, we've both gone through periods where we had a little less to do, right, not, not down to nothing, but you know, kind of post exits. There's that time in which you, you can get a taste of this. Neither of us wanted to retire. Neither of us have, but you don't become a different person. I think that's a big part of it. Was that the assumption was not only will my life be different, I'm somehow going to be different. Right? I'm going to be that person who likes working out all the time. I'm going to be that person who likes reading all the time. But the reality is we have no idea because we've never had the, and I'll use the word luxury here and maybe it's not really a luxury, but we've never had the luxury of being able to just read all the time or work out all the time or do whatever the heck it is you want to do all the time, spend all your time with your family and that's another one. I think we should talk about because that one tends to come up when I'm talking to founders have now exited and there's some real mixed and interesting results in that bag. But I think that's a big part of it is that we somehow assume this is going to be a, a life changing event during which I as an individual change and the reality is you just don't change that much, right? You're still the same you with just a different set of resources available to you. But it's a problem though. It's a problem if we believe all these things to be true and we specifically believe that it's our startup that's holding us back. Sure, sure for sure because we have all these things that they're going to blow up in our face. The first is we're going to say I got to get out of this thing right. All of these things aren't happening because I'm stuck in this thing, so I have to get out of it. So we create this kind of artificial rush to decouple ourselves from our startup and try to get this away from us. And sometimes there's good reasons there's some stuff you do want to get rid of like stress, right? Just stress in general or you know, being leveraged all the time or being broke. I mean, you name it plenty of good reasons to get out of it. I'm not suggesting that, but, but what I'm definitely saying is when we start to idealize what the other side of it looks like and then rushed to get through. It breaks in so many ways, right? And I think from, from our standpoint as founders, we we start to think about, well until I get get this out of my life, right? I'm not going to be that that perfect miracle person in life and in all aspects of my life, Right? I look at it and go, were you really that person before we used to have time, Right, is an example. People talk about, I'm gonna pick up hobbies, right? I'm gonna dabble in so many hobbies and I'm going to be this, you know, this international man of mystery and this renaissance man, woman. And I keep thinking about that and I'm like, dude, I've known you for a long time. You've never followed through on any right beneath since college, You've never followed throughout any hobbies. It's it's as if it's as if the only thing keeping me from being Gordon Ramsay is I just didn't have enough time. Like, nah, it's a little more than that. Somebody keeps dulling my knives. That's it, that's it. Yeah, I mean, I mean like I've got a guitar behind me and I've actually never played it. It's just really there for show, I've touched it like three times. Well, it's it's you can't play it, it's not even it's so out of tune, I'm not sure you could tune that thing. I don't even know if it has strings now that I'm thinking about it right without snapping the neck on it. But that guitar is every person's hobby. Everyone's like, Oh man, I'm gonna learn to play guitar, right? I got all excited about it, got this guitar situation going right, and I'm gonna play all these songs and it's gonna be amazing. The things collected dust for 10 years, right? The thing is older than my kids, but but I could easily make myself believe that it's again, that all these things are holding me back. And the truth is for the things that you want to do in life, not just, you know, start of people whatever you'll do them. Especially as founders were the most motivated people on the planet. If we were going to do any of this stuff, would have been doing it a long time ago and yet we don't, you know? Yeah, and I think it's there's there's there's that aspect and there's the other side is that, you know, I get sad for for a couple of reasons, when I hear people kind of talking about all these things they're going to do again. I'm going back to the motivation like why are you telling yourself this? Why do you need to paint this this future picture that's so different than now and couldn't you be at least sketching some of that into your life at this point. All right, we've talked about this a number of times, but this concept where founders end up deferring happiness now for, you know, the promise of some different future really, really hurts because you and I both know right? The the future is uncertain, right? You, you may have these things happen, you may not, you know, we both have really sad stories about people who did this and worked hard, got their exit and then life fell apart or their health fell apart. Or lots of other things happened that kept them from truly being able to enjoy that future retirement state. So, you know, one of things I'm always trying to harp on is like if you really do want to read all the time, at least start by reading some of the time now, right? Playtested, you might find you hate it, right? Like with so many things that we've talked about, you know, well you, you went through this with, with woodworking right? Where you had some extended time off and it turned out you didn't actually want to be in your wood shop all day every day for an extended period of time, you really enjoy it when it's here and there. But you know, if you had retired under the premise that you're just going to do wood working full time, how would that have played out? Well, it's so funny, you should say that because again, like you said, I did pick up this hobby and I'm saying about it, I was out in the workshop this morning at four a.m. Because I couldn't sleep. But you know, out there for anybody who hasn't seen this on instagram, it looks like Tony Stark's if Tony Stark was was doing what working, that's what this thing looks like. It's, it's insane. Yeah, I'm out there. It's also not heated. So, uh, it wasn't today and I'm out there, you know, like 20° outside building stuff, whatever. And I'm super passionate about it, right? And so I make it happen. I worked in the same amount of hours. But again, like if you're passionate about something, you go and make it happen, Truth is Whenever I do too much of it, right? If I try to do this a few days in a row by day, like 4, 1 I'm burnt out. I'm tired. I'm like physically exhausted. I'm carrying heavy stuff and trying not to cut my fingers off, right? But beyond that, it's, it's special. I'm out there at this insane hour this morning, not because anything needed to get done. I'm ironically building a workbench in my workshop, right? So, but I'm just, I really enjoy it. But I also know that I have to only do it for a few hours and then I have to be done, right? So I don't burn it out whenever I've tried to take an entire week off or something, do nothing but that by the end of a few days I'm like, really border right? Like I actually don't want to do it anymore. I don't want to do anymore. The only reason it's special because I can't do it because you can't do it all the time. Yeah, I think that I definitely experienced that as well when we were living in florida and I was doing a lot of kayak fishing. I loved it. I loved being on the kayak, I loved the exercise, I loved catching fish, loved eating them, loved the whole thing. And I remember that one of our neighbors was like, this guy literally, he had retired from just a federal job of some sort I think. And he, this guy fished every day and he said like, you know, I just, you know, it's been, it's been such a dream come here and just fish every day. And literally like, the guy was like six days a week out on his boat fishing and I just thought like, man, like, I don't know whether I envy this guy or pity this guy or what it is, but I'm thinking like I couldn't do that and I couldn't decide whether like if I was actually that satisfied because he seemed to be truly satisfied. Like I just sort of, no, that's not me. You know, I did a couple of times were like, wait a long weekend and I went fishing three days in a row and by like the last half of the last day I was like, I am definitely good for like at least three weeks, I will not need to be back on the water. So maybe that's just our motorist founders. Maybe there's something different. I'm sure it varies individual to individual, but for me it was like there was no version of like, let's just retire and fish all day, right, can't happen, I'll give you another one and this one cracks me up. We have this idea that all our relationships would be better if not for our startup. Now, bear with you when it says, yeah, the startup doesn't make our relationships better. I've yet to see that what happened where someone was like, you know what, I can't believe how good my marriage is. Like just, it turned out all I needed to be doing is working 100 hours a week and being stressed all the time and barely eating right. Or I've never heard someone say, you know what's really cool about this job is I get to travel all the time, hardly ever see my kids and like, you know, I see instagram updates about them, this is wonderful. Unless you actually really didn't like your family, right? But short of that like again, we've got this idea that our startups holding us back. So again, talking to another founder friend of mine in the past year. He's got a very big family, a lot of kids and he said he had the most interesting feedback he said, you know, I thought for sure that once, you know that once uh I was able to retire, so to speak and you know, not be working my startup, that I'd be so invested in my family and my wife and everything else like that. And he's like and then this weird thing happened all of a sudden, I go from not being around at all to being around all the time and now I'm in everybody's way my wife is like dude, we find something to do. My kids are like, you know dad, I'm in high school, like I don't I don't sit around thinking how much time can I spend with my dad? Like it turns out he's like the one thing I never thought to ask Is, how much more time do they need, turns out they needed like an extra hour or so we don't want exactly dad, could you be running for 16 hours with nothing to do but annoying me all day. Again, it's it's not that we don't want to be with our loved ones. We do, but we have to keep in mind that the amount of time we're trying to like extract or remove from our startup doesn't necessarily have a 1 to 1 home, Right, where all of a sudden we need to put you know, our 16 hour days or whatever we're doing exactly in all of these other things. Point being sometimes we just need a few hours, sometimes we just need a break, maybe a sabbatical right long enough to remind ourselves why we do this, to begin with, why we got so invested. I have yet to meet a single founder. We talked an awful lot of founders of any level of wealth outcome etcetera that has, has said to themselves and said to me by way of that, this worked exactly like I expected. I would never work again. Every single founder I've talked to, every founder I've talked to, the only thing on their mind is how do I get back into another startup? Because for as much as it seems to have, like taken from them for so long, it was also simultaneously the most rewarding thing that they've ever done. And taking it away from them was like taking basketball away from Michael Jordan, or, you know, football away from tom brady, it's who they are. That's fundamentally how we're built. And it's damn near impossible to replace. 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, every day, 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. That feels like a great ending for the first segment of our program here. Uh, so why don't we, why don't we jump? It looks like it looks like people have responded here. I'm seeing 38 comments. I did not open any of them because I was afraid it would screw up the video pain. So let's, uh, let's get over to it. Let's start with Donna. Donna. Are you with us? Let's do it. Donna. Where are you? Donna? Retirement looks like less responsibility that you want to pick that one up. I think the responsibility just looks different.

Wil Schroter: Like you guys said, you

Ryan Rutan: pointed it out, we are who we are and that's not gonna change. So,

Wil Schroter: you know,

Ryan Rutan: it's um, you choose what your responsibilities will

Wil Schroter: be and they

Ryan Rutan: just look different. I think what would that look like Donna? What, what would you like to be less responsible for right now? I think a lot of times when we think about retirement, we think about

Wil Schroter: the financial

Ryan Rutan: security being there.

Wil Schroter: And so the

Ryan Rutan: responsibility

Wil Schroter: with the

Ryan Rutan: finances is a, is a big part of that.

Wil Schroter: Um, and then it, you know, it's nice to be able to step

Ryan Rutan: away from something. So if you have another startup or you have another business, then maybe

Wil Schroter: not being the one that

Ryan Rutan: runs the day to day

Wil Schroter: operations, but yet you're

Ryan Rutan: doing other things in the background, um,

Wil Schroter: that's a different

Ryan Rutan: responsibility. You're still responsible for the financial

Wil Schroter: um implications, but yet

Ryan Rutan: not, maybe not the day to day activities. So I think that looks a little different, you know, Donna suddenly interesting there uh kind of comparing with retirement, what I'm running toward versus what I'm running away from, right, I want to run away from stress. I want to run away from anxiety. But the things that we're trying to run toward aren't necessarily as real as we think they are. That's kind of what we've been joking about in this episode where we're saying how, hey, you know, I want to be able to read voraciously and it's like, I want to be able to read voraciously, I don't necessarily need to read voraciously right. I'd like to be a lot of the time to go to the gym might not actually go to the gym, but I'd like to at least know that I had the time, flexibility and freedom are kind of really what we're talking about, right? And I think we use these other activities as a proxy so that we just don't tell people, I just don't want every moment of my life to be spoken for because A lot of people were talking to don't have that context, right? Unless we're talking to the startup, founder people who worked at 9-5, they may not have any idea what that's like. They're like well what do you mean? Like what do you mean? It wasn't like you were working 24 hours a day. No but my brain sure was right. Like I you can't let it go. So I think freedom, freedom and flexibility are a big part of what we're talking about and and that is something to strive for right? But again like don't necessary have to defer it to retirement. Absolutely. I think it's about balance to retirement

Wil Schroter: gives you the ability to be more

Ryan Rutan: balanced if we let ourselves do it right? Oh founders are so good at this one. Were so good. We just nail this one every time. Yeah sure. Yeah you're you're right there donna alright. Andreas I don't think we really want to fully retire. Can you give your your thoughts there? Yeah sure. I don't think it's For the kind of people that we are that I am definitely and I think all of us are I don't think it's healthy to fully retire. At least not like a one day stopped up like I work until 65 or 70 or whatever and then I just stopped. I don't think that's a good idea. And I think my father has done what I kind of planned on doing. He has stepped down a little bit at the time. He has removed customers that you know he hasn't really enjoyed that much. He has taken away a little bit at the time and now at 72 he's working maybe two days every week, sometimes five days in a week, but he only does things that he likes and nothing else. And I think that's kind of the ideal thing to do to slowly gradually face out the boring stuff And just work a little bit less but keep active, keep your mind active and uh, yeah, I think something like that would probably be ideal. You know, when we built startups.com, we launched about 10 years ago. Uh, a big part of what we did as, as the exercise to getting this started was to list all the things we didn't ever want to do again. We've done episodes about this and that was probably, it was literally our retirement job, this is our retirement job because we basically said if we could get paid to somehow sit around and bullshit with founders all day, that would be like the coolest thing in the world and whatever we were otherwise trying to do was going to be toward this end. So we're like, well screw, why don't we just try that now. Like why don't we just kind of do the things we said, we were going to do in retirement and somehow maybe get paid for it. That that was the biggest question mark. But I think what happened was instead of saying to ourselves, here's all the things we want to do. We started off with years old things we don't ever want to do again and we work backwards from there and one of them. Well, yeah, and also it's easy, it's easy to tell yourself all the things you don't want to do, right, It's hard to be ambitious and say, is this a big enough goal and do the big things, but it's really easy to complain. And so we just sat around and listed all the things we were complaining about and so let's just not do not do that anymore. Ryan, if you remember having this discussion about, you know, being kids growing up and all the time, we didn't get to spend with our parents in saying how we didn't want that to be replicated, you know, simple things, but I think retirement is all, is often this, this fantasy of, I won't have to do all the things I don't want to do and it's, and that's a big part of it, but you're not, we're not necessarily totally, um, kept from making some of those retirement changes now, retirement doesn't have to be for the future. It can also be for the now, I think it's worth noting. Yeah, no, I just said like start doing that as quickly as possible. I mean I'm 42 now, I'm already doing that, I'm already removing all the things that I don't want to do saying no to things, um, Just letting other people in my organization do them, why wait until I'm 65 to do it? Just remove as much of that crap as possible as soon as you can and then you're gonna be happier for it. We chipped away at it to like, like it's easy to make bold proclamations to have that one moment of inspiration while on vacation right down all the things you're not going to do really hard to actually stick to it. Like anything else worth doing. But we didn't try to do it all at once. We just chipped away at it over time. You know, we said, here's where we'd like to be in the future. And then every year we're going to chip away a little bit, you know, kind of refining and pulling off the hard edges around um, what's been bothering us in fun fact, when you take all the way, all the stuff you don't want to do, you come home and complain less. It's not that like life, You've done something so amazing. You just have less ship to complain about your, okay, well, I guess I'm not working with jerks anymore. Well that worked out pretty well, that was half my dinnertime conversation with my wife. So that's not happening anymore. Like it's just, it's amazing how it all stacks up. Justin you're never going to retire. That's a lie. Uh, tell us where your head was at. Yeah. The idea is that it's kind of similar to what my grandparents did, so my grandfather is actually made and lost as well, something like three or four times to his stories, but um for this fourth time he actually retired and then built a self storage business in texas and he's made more money from the retirement business than he did and actually working. Yeah, like you you take away all the stress and somehow some way the creative juices start flowing and so you don't end up doing better for yourself. Yeah, I agree. Richard retirement instead of building businesses for fun to make a living, build businesses for fun only. What were your thoughts there? I like the sound of this, my my startup started as like a hobby that I got good at, to the point where people were willing to pull out the credit cards to pay me for doing it, solving a problem and um it's still fun, like it's not always fun, but on average it's fun, but I also need to do it to make a living um And this is my way to not have to get a job, which is awesome, but my my my vision of a retirement is actually doing the same thing, but then I don't have to do it anymore, which I don't have experience with. Um So maybe the joke there, the way I'm fooling myself there is that removing that need makes it different. Um But yeah, here's the thing um where we're at Ryan and I in the startup dot com team that you were a profitable self sustaining company, right? And so for the longest time, that's all we were trying to be right, we're just trying to kind of get over that hump. Like everyone is right, just trying to make it so that for once you can stop worrying about how bills are going to get paid right? Like anything in life, your worries just move on to something else, but you're just not worrying about survival. The problem is once we got to that point, it was just like because we're founders like, okay, well that problem solved now let's go create a whole bunch more. Like we could have just kind of stopped there. But I think like everyone else, we're like, no, well there's a whole bunch like as we bought all these other businesses, like we have to have other people's problems to solve too. This is wonderful. But I think it's kind of our D. N. A. We like to solve problems which inherently mean we're just driven towards friction, right? We look for friction and that's that's our challenge right? While at the same time we complain about, we talked about, oh my God, I can't believe you know, I've gotten into this or gotten into that like Ryan and I didn't sleep for a month when we acquired virtual years ago, right? At least a month. Um And we're complaining about, it's like, dude, you guys put yourself in this situation. Yeah, It wasn't like we didn't see that coming. It wasn't like, well there's just a lot more work than we thought. Like we knew exactly what we're getting into and we jumped in with, I agree. Um, Jack, your definition of retirements based on independence to invest time, energy, time and attention and the majority of things you want to do. Yeah. And it really comes from, um, total motivation and the vega factor where if you can eliminate the, um, emotional economic and obligatory reasons for doing things and do things because you're curious and you want to play or you see some purpose or potential in it, I really want to eliminate all of the things that suck energy away from me. Again, emotional economic or some inertia obligatory reason get that. So, so, so what is like what feels like retirement for you right now? Are you doing anything that feels like, okay, I'd be doing more of this? I'll say in my day to day, um, that the emotional economic and obligatory reasons for doing things are ever present and the startup being venture backed and you know, it's pressure to perform and deliver and execute and implement. Whereas if I just wanted to go do something randomly because I could, while still honoring my life commitments, I could go do that just because I have the choice to do it. Like I said all the founders that I've talked to, they all have like this 6 to 12 month honeymoon period where they do all the things they said they were going to do and again, all of those things like reading or whatever you're vacationing. It turns out like there's a fairly finite lifespan on how long you can do those consistently before they burn out. The way I was describing. Like when I go in my workshop and go build things like I can do it for a few days. And then after that, I just want to actually usually go back to work and it turns out there aren't that many things that we can actually do with 16 hours a day every day for the rest of our lives, which is why almost invariably everyone comes back to starting a startup, Not just because of the challenge because you gotta have something to do all damn day. You can only play so much golf, right? Or whatever it is that you do. Yeah. I've already played all the golf. I'm going to play in my life. I've decided I've maxed that one out. Yeah, it was very little and I'm good now. Yeah. Alright. Ryan, where'd we leave off? Let's see here. It looks like, uh, but he came back. Yeah. So he came back, he came back. Yeah. So traveling the world driving, spending time with friends and family or diving not driving, diving. Yeah. So again, like just a list of things that we think we would we would want to spend all of our time doing. Don't forget to come back up for air Andreas or it ends up being a really finite time when you're diving. So yeah, let's let's talk to Lindsay, retirement should allow for extended time and a variety of locations that I love more sunshine, more outdoors, a bit more free schedule. Uh Not sure when though, I have a question for you Lindsay, why not now? Like I I kind of did this part of it already. I got to the more sunshine, more outdoors free schedule, maybe less so, but you know with the startup and three kids that wasn't really part of what I felt like was realistic. So why not some of that now, you know, I think that's basically kind of where I'm going because I have taken some time off And um I can't say that a sabbatical does that allow you to kind of get rid of everything and then choose the good things back and then I've done that several times and in my career, but I'm almost 64 and and the thing for me is I have colleagues that are retiring and leaving me, you know, I mean it's nice when you work with people that you enjoy. So you know it's that's a good thing, you know, but I still don't know why I didn't know you were serious about leaving. You know, so I don't know. And I don't have it planned out. I think probably, you know, more financial security, but I think you're smart too. Try to create a situation that you enjoy working with the people you do and you enjoy what you're doing and then hopefully You can narrow down those hours where it's not 16 hours a day every day in retirement. But I think we all have to have some purpose or some, you know, focus of what, you know, what we're contributing to. So for sure, for sure. I'm just wondering, you know, to the extent possible we can separate, you know, those those obligations and the purpose and the things that we need to do or want to do sometimes from just where we do them. You know, my wife and I and I've heard a couple other people, I think even something maybe in this room said the same thing, which is that when we go on vacation, we want to be more excited about going home than than where we were right. And that's kind of what we've we've figured out how to do. And it's wonderful, right? Because I don't, I don't lean into like I'm not waiting for something else to happen. I just wake up every day. I'm happy where I am and I I absolutely love what I get to go do, right? And neither of those things was was accidental, right? There was a lot of deliberate design that goes into this, you know, will said something before. I think it's important to come back to for this particular discussion, which was that we then chipped away at some of those things that we didn't want to do right. So I didn't want to wake up in a place that I didn't want to be, I want to wake up in a place that that fulfilled me in all the ways that were important to me. And one of the things that that exercise was really important for was was figuring out then what does it actually take to make that happen right? When we look off at this Super Amorphous future where we can do all the things. That's really hard to imagine. The only way we can imagine that is through retirement, through an exit through some big cataclysmic moment, like now, okay, now, all of a sudden I'm free to go do this stuff if you just pick one or two of those things and you say, okay, what would it actually take within the business? We need to make more money. We need to hire somebody else to take some of that off my plate. What are the levers that we have at our disposal to pull so that we can make that thing happen and it becomes a much, much easier exercise. The way we approached it by sort of chipping away at the things we didn't want to do and therefore by proxy opening up time and space to do some of the things that we did, but it wasn't an all at once kind of thing, it was, it was stepwise and we got real clear on, well I want to make this happen, so what's that going to take? So I'd encourage everybody to just start to look for those, those opportunities to say, hey, I may not be able to go full retirement, but what's that one thing I could tweak in the next six weeks that would make me super happy and, and again, maybe you try and it doesn't, you're like, well I'm gonna carve out three hours for reading a day, turns out I only need one, cool, I just got two hours back to do something else with. I agree. And you know, I mean, I think just giving yourself when you're that personality, whether your startup, founder or not, just giving yourself permission to take, You know, three hours and say turning my phone off and, and this is for me it becomes more enjoyable then because it's, it's part of your schedule every day. So, but yeah, it's good, good conversation louis you said that uh that you're living your early retirement now from corporate life, if you could rewind the clock a little bit back to corporate life what you've done a little bit differently, if you could have, I think if I could have slowed my mind down and had a little bit more confidence along the way versus trying to compete in a culture that's really buttoned down and not realizing that my brain really, I was an entrepreneur right? And, and I had some freedom to do that. And once I left, I, I was like, no, this needs to get done. And I, and so I, I started down that road and I took all my pennies and I put it over here and I said this is easy, wait till they see it because you know when I worked for the company, everybody loved to buy from blue and talked to lou and lou can solve problems. And when I didn't have this big icon behind me that said, you could trust him because we've been in business 100 years, the game changed a little bit for me. Uh, so where I'm at now is trying to figure that out, right? I mean it's, it's very different skill set. Um, and it's coming together, it's taking a long time I think Ryan for for his help because you get the right information at the right time. And so, so there's been some movement, but as I look at it from the past to today is there is no real retirement, there's no like line in the sand, it'll be sort of this fading out sort of and I say the right amount of time with family, you guys have spoken to that because this is great. So I retired and my brides right over here and yeah, this could be, uh, I didn't realize I was such a, it's so frustrating to other people. Um, so continue to do this and there'll be another thing, I'm gonna have to have another building just so I leave this building to go over there and, and she can have her world back. But my brain is busy and in corporate life they put me where I worked, right. And that was where something was broken and needed to be fixed and that's great for me. And that's that entrepreneur piece, right? You can go in there and take something, turn it around. And so I don't, I don't know that that part ever goes away from you as you age. It's a, it's a number of retirements. A, an old phrase, I think specifically for founders and people that have brains that just need to be occupied because maintenance leads to like if I had a job and I've had them where you get things put together, I start to get loose, right? You're not as focused on things now. I spend a little bit more time cajoling with friends and whatnot and, and, and so it's not as productive though. It feels good in the moment. So yeah, I think you fade, you fade into it. There's no line in the sand and having the revenue and that somebody said it really early on that security that I don't need to be a king. I just need to be able to kind of come and go and you know, this seems to be a recurring theme. I mean, I'm gonna jump now to Katherine's comment, which is retirement to me is that I'm still building things, products, services, nonprofits, etcetera that matter to me. But without the anxiety that the outcome of those projects will determine my ability to cover my living expenses or have to return capital to others. Right. And so this this is kind of a reflection that we've heard a couple of times over Catherine, you're still you're still here with us. I have a very limited view of who's still on the call. But yeah, but I think this is what we keep kind of coming back to, which is, and I love this, right? Like how, how amazing is it that we we have this, this opportunity, this, this luxury of saying like my retirement, I just want to do more of what I'm already doing with just a little less pressure around it. Right. How amazing is that? Do you, I mean, think about people in other lines of work and non entrepreneurs, people who just working a job. How many of them are you like you think like, you know, as soon as I'm done working middle management for amazon. I think what I'd like to do, my retirement is work in middle management for amazon, right? Nobody ever right, Nobody ever said that so, so Catherine? What? Yeah, so why do you think that is? Well, I mean I think that as a founder and will knows it's a lot, we've talked about it. Um you kind of go into this with this, especially for the first time founder, like I am this expectation that I can just muscle my way through anything. We have to believe that that's not reality, you can exert every ounce of wisdom and hard work and discipline and sacrifice and things can still not work and you know, being able to kind of work through that mindset and understand that as long as I always have a really clear next milestone that I'm working towards and that's going to be a decision point of, you know, a go here, be go there and just always having that focus um makes this journey a lot more enjoyable. Not certainly immediately or entirely less stressful, but somewhat less stressful. So I think it's it's kind of like we we love this trapeze act that we do, it sounds like our our pre retirement is the trapeze act, Our post retirement is the trapeze act with a safety net, right? Like that's kind of what this comes down to like I want to still do all this risky stuff, I just want to know that if I fall, it doesn't cost me everything, it doesn't cost me my financial freedom, my health or anything else. Yeah, makes sense. And I think to the point you guys made earlier, it's how real. So inter leading in those things that we maybe are like putting off to some future that may come. And I'm actually just isn't an example of this. You know, I haven't met my nephew yet. He's five months old and I've not met him because he's in Hawaii and when am I going to carve out time to go to Hawaii and visit my nephew anytime you have 14.5 hours for a flight, Kathryn, where do I find the time to do that? And You know, this is like that example if you're going to miss it. You know, if you don't find the time for it and I don't want to wait 20 years and then be like, Okay, now's my chance to meet my newborn nephew because he'll be in college. Right, right. Make sure you upgrade the gift somewhere along the way. He's not going to be into the same stuff. Yeah, exactly. Which was something else I wanted to touch on. We didn't talk about this in the course of the podcast or or in the in the poster so far. But the idea and that kind of that we're going to be different people. Well we will also be different people. Some of these things like we've planted these seeds in our minds maybe for decades around what we're gonna do when we retire. Let's not forget like we're going to be different in some ways when we retire, right? Like when I, if you'd asked me what I want to do when I retired when I was 22 I'd be like, I'm gonna do jujitsu all day long. I'm going to play soccer all day long. I mean like if I'm 60 when I retire, I'm probably not going to do those things all day long, Right? It'll kill me. You're gonna try. Yeah, so we have to, we have to plan for some of this stuff. Alright, who else we got here? See to grow said dreaming retirement that way, like swimming and sunbathing every day is nothing but the outcome of an overloaded founder life, you try to convince yourself you'll stop one day and and you'll deserve to live properly. Oh man. Yes. So this is kinda what I was getting at before. What is this underlying motivation? Why are we doing these things? So yeah, so this is the, I'm going to dangle the carrot in front of myself even though I'm holding the stick with the carrot on it. I'm gonna chase this because it, it helps me to uh to get to something that I want in the future and yet don't defer the enjoyment. I think it's such a great piece of advice. Um we said this once in the podcast. But yeah, you don't earn any interest on happiness, enjoyment or life differed. You just lose it, right? Just, it doesn't come back and then it certainly doesn't compound will you pick any others out there? We were just making fun of you, you're making fun of me a little bit trying these are awesome. I love doing this with all of you guys because like when Ryan and I do it, we're just kind of hanging out in a room by ourselves, so to speak and like, okay, I guess we're done talking about this, although like the conversations are fun. So I know I'm probably sure Ryan sediments here, but I really want to thank you guys for taking the time with us and in being part of this episode, we're going to do these every month. So if you want to join in on those two, we would love to have you. This is just, this is what we get to do. We just get to run bullshit with founders. So it's, this is our dream job, this is retirement. 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, like all day long, pretty much talking about every startup topic you could think of from fundraising, the customer acquisition to just really had 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 were 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.

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