Startup Therapy Podcast

Episode #70

Ryan Rutan: Welcome back to another episode of the Startup Therapy Podcast. This is Ryan Rutan joined as always by my friend, Founder of, Wil Schroter. Wil, welcome back to the podcast. Here we are.

Wil Schroter: Thanks for having me, friend.

Ryan Rutan: You're welcome. Hey, so today, this is something you and I talk a lot about how we've structured our companies to kind of allow us to live lives we want to live while we're running them. That's not something that a lot of people do and retirement is still very much a concept, but that's one that we kind of want to blow up a little bit today and pick apart and kind of get out of our heads, how we think about retirement. Is retirement still a viable aspiration and why is that still a thing, right? Like why do we need to work in the mines for 20 years and then stop? Is it 20 is it 40? I forget, how long do you have to be in the mines?

Wil Schroter: Let's hope we never have to find out. Kind of felt like the mine from time to time. I have to think about it man, like retirement in this day and age just isn't what it used to be. And in the startup world, wouldn't you say that a big part of the implicit understanding is that we're gonna sell this thing and make so much money, we can retire? That's always the big carrot that everyone's looking toward. No one raises money so that they can just get a salary. Everyone raises money so that they can grow, so that they can make an exit, and make so much money that they can retire. Retirement — not quite in the "work 50 years and get the golden watch at IBM" frame of mind is always kind of part of the conversation, but I always think that it's a part of the conversation that's such a driver of so many decisions, yet, is one of the least talked about parts of what people plan on doing. I don't think people really put a lot of thought into retirement, and by way of that make a lot of dumb decisions on the way toward this so-called retirement. So it's worth unpacking today, what do you think?

Ryan Rutan: Yeah, for sure. I think that the concept certainly has changed. I mean, even just the way this used to work, like trying to explain to my grandmother what retirement looks like now, she's like "well you work at the hospital as a registered nurse for X number of years and then you retire and they continue to pay you forever." Some of those things aren't even possible anymore, like pensions no longer exist. In the startup context, obviously, it's different but talk about overshooting the mark. I mean, if my grandmother can retire quite happily after a career as a registered nurse (we're going back to starting in World War II era, so she had a few years to make this happen), do you need to sell a company for $100 million dollars to do the same thing that my grandma did? Probably not.

Wil Schroter: I think it's a bunch of things. 1. I think we're overshooting the market, how much money we need, and we kind of get into that. And I think 2. we're overshooting this concept of retirement. If retirement to us means "I never have to work again" and you're saying this at 28 years old...

Ryan Rutan: Have you even started working yet? Yeah.

Wil Schroter: ...You haven't been around long enough to understand how much time you have to fill between now...

Ryan Rutan: "I'm off my parents' medical insurance plan, time to retire." Right?

Wil Schroter: Oh my God. I mean, most of the people that I know that are retired anywhere early are bored out of their minds. They're just looking for something to do. And Ryan, we don't have jobs like we used to. My dad was a carpenter, right? At some point, his back hurt, his knees hurt, he had to stop doing that job, and I get it. It just kind of made sense — he physically couldn't do it. You're updating blog posts, dude, right? Come on...

Ryan Rutan: You can probably keep doing that for a while.

Wil Schroter: No, I'm just saying, the work many of us do (not all of us) just doesn't have the same kind of drudgery that it used to where retirement was a safety net from pain, right? I think what a lot of people are often talking about is "I want to be safe — I want to stop doing this high-stress kind of work so that I can do stuff that doesn't feel like stress." And of course, there's value in that. But, we have to ask: if you're trying to get to retirement to go do the things that you've always wanted to do, my first question is "why aren't you doing any of those things already?" I mean, if you really distilled it down (and Ryan, I toss this to you), if you were to think right now "What are some of the things that you're maybe even doing that look like retirement to you, or maybe you weren't doing 5, 10 years ago? What would those look like?

Ryan Rutan: Well first, I'd like to just get back to doing some of the stuff I was doing, you know, not to beat a dead horse here, but we're still in Covid, we're still in lockdown. So, just give this a thought for 10 seconds. Imagine having retired at the beginning of this year.

Wil Schroter: Oh God, worst time ever.

Ryan Rutan: Literally what the fuck are you doing at this point, right? How are you spending your days? So yeah, for me it's about spending some more time doing things I'm already doing, and I think it speaks to the fact that we have sort of accelerated the concept of retirement by putting those things into our lives now. Like, I'm not waiting (and for good reason), a lot of the stuff that I really enjoy doing at retirement age, even 10 years from now, some of that stuff might not be possible. I don't know how long I can continue to play competitive soccer. I don't know how long I can continue to do competitive jujitsu. I don't know how long I can paddle my kayak into the sea and catch big fish. I hope for a long time because I love all those things, but I'm also not willing to defer those and just say, "Hey, let me pretend that by doing some other things now, somehow I'll get to do more of those in the future." For me, retirement would look very much like right now, it's what I'm doing. Obviously, this year is a bit of an outlier because a lot of those activities have either been heavily modified or had to stop entirely, like soccer, I'd go kick a ball around by myself, but that's not a whole lot of fun. Really retirement for me would just be the world coming back to some level of normalcy and I'd be like, "I'm retired, I did it!" It's spending more time doing the things I've already identified that I enjoy. And I think this is one of the major kind of bifurcation in this entire decision. I believe — and I know because I talked a lot of people about this — I know that there's a lot of people who, for retirement, is going to be this exploratory phase in their life where they go and figure out: "I've now put in my time, I've saved my money, I can stop doing my work — now I can go figure out what I enjoy about life." It's so sad to hear people say that, but then they're going to use retirement to figure out what is fun in life and what they like to do, and how they want to spend their time. I already know those things and I already get to spend a sufficient amount of time doing those things. I'm not dying to spend more time getting my shoulder twisted out of the socket. I enjoy it for exactly as much time as I do it now. I don't need a ton more of that, right? I'm good.

Wil Schroter: Well, let's dig into that a little further. So, there's a fair amount of people (especially in the startup world), that are all in killing themselves to make their startup work. And there's no version right now in their minds where they're saying, "hey, I've got all this extra time to travel, play soccer, or do all these things" A lot of what you're talking about, Ryan, are things that you get to do now, but you didn't necessarily get to do five years ago when we were in the thick of it, right? We're in a different place now than you were and we deliberately tried to unlock some of those things. But I also think that our startups should be helping us get to that goal without necessarily having to sell. In other words, part of our stated goals year over year should be, how do we unlock some more of our freedom so that we can do the things that feel a little bit more like retirement now and when people say "I can't, there's too much work to be done" etc. — it's bullshit. Ryan, you and I have both been through this for decades. We've worked ungodly hours. I made the same excuses. I said the same things: "It can't be done." Everything CAN be done, if you allow it. Everything CAN be done, if you plan for it — right? But if you give the blanket statement, "I'm just too busy," honestly, you're not. You've only got maybe five hours of highly productive time, the rest of it is time that can be filed any way you want (some of it just requires work) but you can time shift it about when you do it, where you do it, etc. And I think when people say "I can't and therefore I have to sell for 100 million to get to retirement," I meet very few people who can make that statement in a resolute fashion and stick to it. I think a lot of us are living on deferred living and it's a huge, huge mistake.

Ryan Rutan: Yeah. Sadly, I think people who are living on deferred living think that they're somehow accruing a balance and I would say what they're really doing is accruing of debt in terms of life, and this time you're never gonna get back, and not necessarily time that you're trading with any level of certainty for what's going to happen in the future. None of this is certain. You could work for a company your entire life, they could cancel your pension. You could work on a startup for decades and not have it sell. And if you didn't design it towards that everyday enjoyment, for allowing yourself the time, I think it comes down to a couple of things: we've talked about this a lot, but permission to say it's okay to have some balance in this, and then, proper planning. And I'll put that in two categories: 1. How you're planning the work that actually gets done: how to structure your days, how to be efficient, how to be effective, and how to focus on the things that matter, and then 2. Also planning for that other time, and being clear in what you're trying to unlock for yourself. Like if I just said "I want to retire," I can't make that happen tomorrow. But if I say "I want to be able to spend three hours a week doing jujitsu and I want to be able to spend four hours a week doing soccer, and three hours a week coaching soccer for my kids" — I can do that. I can make that time appear, right? Just like magic by simply moving things around, structuring my day in such a way, and just making sure that I'm focusing on high-value targets. I think when you use the excuse that "I'm too busy" something really important and horrible happens, which is that you just assume that spending all that time is actually accomplishing something. I no longer have to prioritize my time because I know I'm spending it all, so I must be doing good stuff, right? I'm spending all my time, I'm putting in all the effort "go me" and therefore, it's justified — horrible trap to fall into.

Wil Schroter: Okay, so, kind of TL;DR what we're going to keep chipping away at here is that retirement doesn't have to be this all in, I'm now retired and I no longer work kind of goal. Retirement should be the things that you want to do, and the question is, "how much of it can I do right now?" And you'd be surprised if you really push that, it's way more than you think. Here's what I'll say though, Ryan, and like tell me what you think about this: I think that when you're working 16 hours a day and you have no free time to do any of the things that you want — hang out with your friends, your family, travel, do anything — then it feels like retirement is the only exit from all of this misery. But then something interesting happens, you sit back and say, "look man, I just need one hour a day to do yoga. I'm way into yoga, that's what I wanna do, I need one hour a day to put into that" and you do that. Then all of a sudden you say, "wow, there's a world of difference between not being able to do anything and being able to do a little bit of something." I think as Founders, we often put ourselves in a position where we can't do anything and so retirement feels like the freedom from all that. But what we're really talking about is, "I want to be able to kind of break that and just do one thing, two things, three things..." and we start to realize that just chipping away at that, it starts to feel like a little bit of retirement. It starts to kind of break that feeling that "I'm all wrapped up." Does that make sense to you?

Ryan Rutan: It does, it does entirely. Especially at startup Founders, that shouldn't be a hard concept to grasp. Like, MVP your retirement. You don't need to go all-in. You didn't launch your startup with everything that ever needed the day you started it, that's why it's hard. In the same way, if you're in a position where, again, I'm gonna argue a lot of people don't even know what they would do with that time, so just creating all of it at once would just be a tragedy of riches. Right? So ease into it. Figure out that one thing you wanna do and try it. You might find out you don't like it. You know, you and I have both MVP'd a number of life-changing things. We both tried living in different places with varied results. For me, I really enjoyed the last couple of moves we've made. For you and the family, you decided that you bounced out, you bounced back, you bounced out, you bounced back, and for now you're like, "we're good here, actually. We're glad we did it because now we know." And I think that's the other thing that's really important is you get some certainty around this. Because if you're just in a position where you don't know whether you're gonna enjoy it or not, the level of desire there might eat away at you like, "man, I really want that, I really want that, I really want that" and you really work hard to get there and spend far more time achieving it than is necessary to just sample it and then you get it, and find that you don't like it — and that'd be terrible. What if you guys have waited for 25 years to figure out if you like living in L.A.? That would've been a disaster, right? It'd feel terrible.

Wil Schroter: You know? So I actually tested this firsthand. A few years ago, my wife and I sat down and we were like, "let's figure out what a retirement life would look like." We had a bunch of places in mind, but one of the places that I always wanted to live since I was a kid was Beverly Hills. To me, that just felt like the most ostentatious place you could go, and if the rich people in Beverly Hills don't have it figured out and I can't figure it out there then, well, who knows, right? So we did. We moved to the cool place in Beverly Hills at the top of a mountain. It was amazing. We had a hot tub and pool and everything that overlooked the valley. It was incredible. So I thought when we moved in, "This is it. We found our retirement home, this is retirement living, this is exactly what retirement's supposed to be like." And to be fair, for a couple of weeks, it was. For a couple of weeks, I'd wake up in the morning — and Ryan I remember telling you all this as it's happening — I'm like "Ryan, I just got up, I just walked out to this pool, I'm sitting in a hot tub right now, um staring at Channing Tatum's house."

Ryan Rutan: I can see all 12 of his abs from here. It's amazing.

Wil Schroter: It was amazing, right? And I was like, "wow, this is like how the stars live." And I mean, no one's staring back at my house being like "dude, that's Wil Schroter's house!" more like, "I don't know, some idiot from, Ohio moved in over there."

Wil Schroter: The point is, I'm sitting there, the weather is perfect, the setting is perfect, everything is perfect — and for the first few weeks it was AWESOME. Everything about it was wonderful. But then something interesting happens. In week four, I get up, I just don't really feel like it in the hot tub. I just want to go to work, so I'm sitting in front of my laptop. Week five, week six, week 10, week 20 — that hot tub hardly got any use whatsoever. That view really got any use whatsoever. I just worked in this tiny room (because this isn't a big house) in this tiny room for 16 hours a day just like I was doing before we moved there — not a damn thing changed. But it opened my eyes. I sat down my wife and I said "This whole time, we could have spent 10, 20, 30 years trying to work up to this, and the truth is, we just got to fast forward it now — I'm not going to spend the rest of my life working up to this, this is bullshit."

Ryan Rutan: Yep. Don't need this. Don't want this.

Wil Schroter: It was cool for a minute and then it just wasn't. My point is, if we can't define and/or (if possible) get some experience for what that retirement living or that next thing that we can't do is, I think we can spend an enormous amount of time trying to build up to that. And again, it doesn't have to be a freaking hot tub in Beverly hills. It could be, "I just want a vacation more or travel more." Okay, find a way to take some time off and travel more. Once you've traveled for like three months, if you can travel that long, you might be like, "Dude, actually that was enough. Like I don't want to do THAT for the rest of my life."

Ryan Rutan: Yeah. Living out of a suitcase isn't fun.

Wil Schroter: And I guess the way I look at it is, I call it "popping the bubble." If you just pop the bubble on whatever that dream or fantasy or whatever is, and it's _still_interesting, okay, there's something there, maybe it's worth stressing for. But if it's not, don't you really have to wonder what the cost would have been for deferring for 10, 20, 30 years to get something that you found out in a few weeks you didn't want anymore?

Ryan Rutan: Again, as Founders, we're so used to testing stuff, right? Like A/B testing — not just for landing pages anymore. Why do we let our personal lives and our personal dreams just sort of sit there while we test the shit out of everything else? We validate everything else. We prove out each market before we go all in. We prove out each marketing channel before we spend money on it. Then we're like, "Oh but my hopes and dreams? They're over there somewhere collecting dust." The other thing (and I think this is worth mentioning) in addition to just getting to that outcome and then not liking it and regretting the time that you spent doing it, imagine how much it changes your decision making if you do have this lofty goal and you're like, "I need a yacht and I need them to rename one of the Caribbean islands after me, so I'm gonna need to exit for $150 million, or this just isn't gonna work." So now you start making decisions that point to that direction. Not only do you finally get to that outcome, but you've made totally different decisions for your business. Maybe you decided to take on capital because we need that to scale to this bigger level so that we can exit — that's what everybody who exits does — they're all funded. You start to make very different decisions about your business because of this other goal and dream that you don't fully understand and haven't validated yet. And man, there's a lot of danger packed into that whole decision matrix.

Wil Schroter: Also, I think you touched on something. The number of hours that it actually requires. I'll give you another example: I mentioned this a few times in the podcast, I got way into carpentry, like way, WAY into it. So much so, that on the weekends, I couldn't do enough of it. I was doing remodeling and stuff, I'm just crazy into it. And I thought to myself, "I would love to have more time to do this." So, if you remember, Ryan, a few weeks or a few months back, I took like a week to do nothing but that. Day one: totally in heaven. Day two: I was like, "oh my gosh, I have to find a way to do more of this in my life." Day three, I'm also like, "oh, my back kind of hurts a little bit, kind of like my dad now." In day four, I'm like, "fuck this, I don't want to get up and do any more carpentry!"

Ryan Rutan: I've inhaled my monthly quota of sawdust, I'm good.

Wil Schroter: All I'm saying is, when I couldn't do it, it felt like something I wanted to do forever. But once I gave myself kind of a full breath of it, I was like, "oh. you know what? I want to do this a couple of days a week." Think about that, think about me saying, "hey, I would love to figure out how to exit my company and sell it" so I could do more of that, only to find out that I wanted to do like four days of it and then find anything else to do. I think there's a real danger in having this certainty around what you expect retirement to enable you to do without ever testing that it actually enabled you to do it.

Ryan Rutan: It sounds absurd, and yet, that's what almost everybody does.

Wil Schroter: There's another part of it (and I think this is just as important). We all have this concept that with retirement we would have endless choices of what to do. I have so much money that I have so many things that I can pick to do and how wonderful does that feel? I don't have to go to my job anymore, I can just do some angel investing (everybody says that's a dumb answer — I can do this, or that, whatever). The point is though, are you really this every man, every woman person that has so many hobbies and so many interests that you can fill 16 hours a day, just fucking around? Honestly, I'm going to say this: probably not. And I have a ton of hobbies, Ryan, you have a ton of hobbies. Dude, it is hard to fill 16 hours a day with something that isn't a job and every time I talk to folks that have cashed out, they say the same thing. They say, "man, I'm dying to start something" and I always ask them the same reason, "do you have to, will it pay any bills?" They say, "absolutely not." They say two things. Number one, "I have no idea how to fill my days" which is fair, it's hard to. And number two, "I need purpose." One of the things that people often forget about — especially Founders who are so dead set in our purpose — is that when you remove that, it's no different than my wife who's so focused on caring for our kids and it's such a big part of who she is: if you take that out, when we go empty nest, that's going to be very difficult transition. That's a big part of her DNA and identity. I think people vastly underestimate how important their job is to what they do. Does that make sense?

Ryan Rutan: Yeah, we spend most of our waking hours doing it for most of our lives and the idea that it's not gonna feel weird when we take that away — bit of a misconception. But people don't think about it. The parenthood analogy is a great one. If you're the primary caregiver for kids, there's this sort of perceived timeline used to be 18 now, I think it's what 36 before the kids leave the house? So, it's a huge transition and it's one that nearly everybody struggles with in one way or another and it's often directly tied to some other type of retirement. Now we have this free time now, the kids are gone, I can retire from my job and now life is... boring? This seems to be the story for a lot of the folks that we know and talk to that are on the other side of this. It's like, "how do I fill my days now? I had all the stuff that I had to do (which sometimes was drudgery, sometimes it wasn't that kind of depends on how you structure your life and your work), but when all that's just taken away, whether you wanted it to be or not, it's tough! That's, that's a big, big transition. And not one without some testing, you have any real clarity what the other side of that looks like. I'd argue that given it's a major, major life event transition — you should be testing, you should be preparing yourself for this in some way (and I don't mean just like saving money so that you can do it. I mean preparing yourself for the activities that come post that point). But it just seems to be a huge, huge hole in a lot of people's lives, and I would argue more so in Founders' lives. I think that there's a lot less understanding despite more flexibility to do those kind of things now. I think as a Founder, it's easier to start to playtest those things, but I see less of it than I do with people who are working at 9-5.

Wil Schroter: Well, I think we've got a couple of things. I think one part of it is, we want to be de-risked, right? We want to be able to take those leaps and know that we'll be okay. This goes back to safety, right? Similar to this, we want to be deleveraged. We want to know that if A-hole investor comes back to us and gives us a hard time, we can just kind of say F-you and go our own way. I mean, we all want that kind of feeling. That said, I don't know that the only way to get there is a full massive cash out. I think a lot of the parts of what we're talking about (this is a recurring concept here) is retirement should be something that you are constantly chipping away at by creating more opportunities to spend the time the way you want it, by de-risking yourself, by deleveraging yourself with your time. By the way, it's always about time. Yes, there's a little bit of money involved in it. I'm not gonna knock that, but it's more often about time, it's about allocation, and at its core, it's about permission. It's about giving yourself permission to do the things that you actually want to do. Having a ton of money kind of feels like that gives you the validation and permission, but the truth is, most of what you always wanted to do, you could have done all along. That's, that's one of the most recurring factors.

Ryan Rutan: That's it, it's available from right now.

Wil Schroter: But I think all of that (being de-risked and deleveraged) is really just a side benefit to the bigger component here, which is not having this gray amorphous cloud of what retirement is to you. I think if you could say retirement is specifically these things, "retirement to me is two hours a day of working in the woodshop, four hours a day playing with my kids," (whatever your version of retirement is) and you are super hyper clear about that, I think the first thing that would come out of that clarity is to be able to say, "how much of that can't I do right now?" In other words, "how much am I putting money as kind of a wall against me not being able to do that? (And the truth is what's really preventing me is permission, discussion, and maybe understanding with my other co-founders, etc.)." But the biggest part of it is, if we look at retirement as this gateway that "until I get past this massive (typically on the scalable) gate, I can't retire" I think we're broken on arrival. And that's kind of what concerns me.

Ryan Rutan: Yeah. I mean it's not one of these kind of things you want to figure out as it happens. And again, the ability to playtest this is there. There's no reason you can't be doing these things and the other side of it is — in what quantity? I said it before: I like jujitsu, I love soccer, I love fishing. If I had to go fishing every day, that's called being a fisherman, that changes it significantly. And it's an interesting concept, but anything that you spend all of your time doing can potentially become drudgery. I love vanilla ice cream, like ice cream of all sorts, I don't want to eat exclusively all the time. That's not good. It's not good for me, and it would lose its magic. Right? And so I think that that's the other side of this, is that some of these things are special because of their rarity. If I was able to play soccer all day, every day (I guess I'd probably getting paid for that might be kind of cool actually), it would lose some of its luster. It would no longer be that special thing that I get to go do. It's now just the thing I do all the time. Same thing with fishing, or jujitsu, or... anything. I love spending time with my kids and I want to spend more time with them (I try to spend as much time as I can with them) if I had to spend all day every day with them, would I have the same level of fulfillment? This is a discussion my wife and I have with some frequency that she's in that position where she spends a lot more of her time with them. For her, retirement might look like spending a little less time with our kids. For me, it would look like spending a little more time with our kids. It's about balancing out these things that you need to do (the things you're responsible for, the things that you want to spend your time on) and just making those work as a system as opposed to some weird binary point in time where I stopped doing one thing and start doing another. As you talk through it, it sounds asinine and it doesn't sound like something I'd want to engage in, but it seems to be the typical path for people.

Wil Schroter: You know, one of the things that I think a lot about, and I talked to Founders that have made a little bit of cash early in their careers: invariably, they almost all go back to working. I touched on this earlier, but I don't think there are a lot of other hobbies that activate us the way our jobs do. Folks say, "well, I want to put that money into (or that time rather) into nonprofit work, something that maybe doesn't pay me," that's fine. That's a job. It's real work. But I think for a lot of us, what our dream of retirement maybe should be — and I can't speak for everybody, but maybe one consideration is — I want my work to align with how I want to spend my day. And a lot of people will say, "well that means I wake up at 11 o'clock and work for four hours" and you know what, fine! There are actually jobs you can do right now that align with that (not a ton!). But the other side of it is, if you were to say (if you were dead set on this, the way Founders can get dead set and locked in), "I'm gonna work five hours a day, I'm gonna work like a madman for five hours a day, but it's going to be five hours" — you could make a career out of that. You could do that now. You don't have to create the kind of risk in timeline (and frankly, the cost as far as your mental health) in trying to get there in order to do that. I've seen this time and time again. I think retirement is a construct that we need to flesh out entirely. We can't guess at what retirement is to us. And we need to test it, like we talked about. I also think it's something that we should be activating every year. We should look at every year and say, "how can I get closer to retirement on things that aren't just money?" I would say, in my personal journey, every year that goes by, I get closer to what I consider to be retirement because I start to get substantially more agency over my day purely because I allow myself to.

Ryan Rutan: Yeah, right, because you plan for it, you give yourself permission, and you demand that it happens. And then it does! I think that using the financial piece as the North Star is super dangerous. Let's use an example here (an extreme example), but look at professional athletes and look at the top performing professional athletes, like just think of the all-time greats in any particular sport. Do you really think that they were still playing because they needed the money? How many championships did Jordan need to win before he's financially set? After the Nike contract was signed, the deed was done, right? But he kept coming back. It wasn't retirement because he had achieved financial success, it was retirement because he didn't have things he needed to achieve. He had satisfied himself — and I think that's really important. To me, that's an important trigger for retirement. I'm now satisfied that I've come and I've done what I set out to do, and now I can pick something else to go do. In the same vein, let's say we get to a liquid event with and now none of us have to work again (financially, none of us have to work again). But what if we hadn't fully executed the mission? We've said this before, we want to continue to help Founders on their journey for time and memorial. This is what we want to do. That feeling doesn't change simply because I now don't need money as a result of that. If my purpose hasn't been fully met, if I'm not satisfied that I've done what I set out to do, am I going to want to retire? Am I going to enjoy it? Am I gonna even be able to focus on those other things, or will I want to? The chances are I'm gonna want to keep chasing that thing that I set out to do. Obviously, if you're working in a job, you're managing a Blockbuster (the Blockbuster, the last one) that might not be your life's aspirations, so I get that you might want to stop doing that. But I think there's a huge difference between wanting to retire and wanting to not do something you don't enjoy doing. I'd argue in the same way we're suggesting playtesting what your retirement looks like, if you don't enjoy what you're doing, start with that. Fix that problem first, and then the context of retirement is completely different. Totally changes because now there may not be a need to do it anymore, or the need to do it is far reduced, or you may feel like you've retired already, right? And I think that's a great aspiration.

Wil Schroter: You know, the way I look at retirement and when I look at my own retirement (actually, not just my own retirement, but our team as well), I believe retirement for a Founder, for a founding team, and for a vision of the company should be a journey that says, "if and when a financial event happens, where we get a liquidity event etc., the ultimate goal of retirement, is that nothing changes. Is that the liquidity event actually doesn't really affect us dramatically in any way, because all along (year and year out) we deliberately planned to get more and more time against an opportunity to do the things that we wanted to do, so that retirement felt less and less like this kind of huge boulder that we're trying to run from, but to." From, in that "oh shit, you know, I hate my life etc, I'm running from it" into meaning (this is this is my Indiana Jones analogy) that I'm jumping out of the cave and go "shit, I think I made it." I really don't see Founders talking about how "every year I'm going to get closer to retirement, because I'm deliberately building towards something that's important to me." By the way, I see a handful of people, but it's definitely not part of our typical narrative and I think that's a huge miss.

Ryan Rutan: No, I think the answer to that question should be like you declare "I'm retired!" And like "aren't you still running" "Yeah, I'm doing both. I am both still running my company and I'm retired." Again, retirement is probably half mindset, and half ability to be able to exercise on some of that.

Wil Schroter: I think it's a combination. Part of it too is, there's a handful of things that I just hate doing. "I hate working with the customers that we sell to. I hate working with some of the people we work with, etcetera." And I get that, I'm not pretending for a second that any version of working our jobs is all Shangri-la. Conversely, there's a handful of things that I want to do that at my current job just prevents me from doing. From maybe where I live, from maybe what I'm getting to do like vacation hobbies, etc. I get all of that, and I respect that. But again, I would say that instead of waiting for this amazing moment that somehow changes it all (which kills me — I hate saying this, but kind of what I'm saying is there's a good chance that may not happen, and I don't want all the Founders that are listening to this to say "if that doesn't happen, I'm totally screwed." I think that's a terrible plan). I think a better plan is, "look, I may not get to a liquidity event — that may not happen. However, there are a number of things that I'm going to change year in year out where I'm going to chip away at that goal, and over the next five years (regardless of whether I sell) I'm going to have 70% (making up a number) of all the things that I want to do in retirement already in place." To me, that's a kick ass goal.

Ryan Rutan: That's a wrap for this episode of the Startup Therapy Podcast. This is Ryan Rutan on behalf of my partner, Wil Schroter, and all the family, thanking you for joining us — and we hope you'll continue to join us! Be sure to subscribe, rate, and comment on iTunes or wherever you love to listen to Startup Therapy. You can find all of our episodes at If you're looking for more amazing resources to launch or grow your startup, be sure to head to and check out Startups Unlimited. It's everything we have to offer — from our online university to our amazing community of experts and Founders, and even all the tools we've built like Biz Plan, Fundable, and Launch Rock. It's everything a Founder needs visit that's You'll thank me later.

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