Startup Therapy Podcast

Episode #86


Ryan Rutan: Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan from startups dot com joined as always by my partner friend and the Ceo and founder of startups dot com Wil Schroder will, can you hear me okay bud?

Wil Schroter: Just

Ryan Rutan: kidding, just kidding. There's gonna be a lot of that today guys. So we're exploring this notion of, you know, we hear this question a lot. Am I too old to launch a startup? When will I be too old to launch a startup? Is it too late? Right, that I miss that magical ship that comes along and says, hey, if you're this age jump on, we're gonna take you to treasure Island and we're all going to start startups and I think we will unpack this in a lot of ways. But really what we're talking about isn't are you too old to start a startup right at the risk of pissing everybody who's probably our age off? That's not really the question here. The question is, how does that cost and how does the risk profile change over time

Wil Schroter: agreed. And look, man, it's funny because I think everybody thinks about this forward continuing throughout their entire life as it relates to startups. It's always really specific like this tradeoff, if you will between when will I be ready? Like I'll have the education, the experience the finances to get launched and then on the other side, when is it too late? You know, when will I actually be at a point where I have too many responsibilities or consequences in order to take that risk and I think maybe a good way for us to look at it Is kind of take it sort of decade by decade, 20s, 30s, 40s and beyond. And start to talk about how the risk profile changes and you know, certainly we've been through this, you know, we're both in our forties now and as I'm rounding the coordinator 50 not that close but close enough, you know, I'm starting to think about that decade as well. So probably worth digging into and maybe opening up with how

Ryan Rutan: this all begins.

Wil Schroter: You know, Ryan, like what was your purview of how much time you had the consequence,

Ryan Rutan: et cetera when you're in

Wil Schroter: Your 20s? Sure, well

Ryan Rutan: you skipped the decade. That was important to both of us when we both started this in our teens. So I mean that that's a very different time, but yeah, let's let's let's

Wil Schroter: write it,

Ryan Rutan: that's exactly it. So, you know, the interesting thing there is that, you know, you've got very little in terms of resource at that point. And so I think that there's two ways of looking at that, which is to say that I have very little resource, very little backup, very little support. Um so this is very risky on the other hand, what am I really risking? Right? My back end is so close to the ground as it is, does it matter if I fall? It's barely gonna bruise me. So the decision for me at the time when I decided to continue with the business beyond university and then ultimately sold it right before I graduated. But the decision I had made prior to that opportunity coming was to continue with the business and I was at a bit of a crossroads because I was preparing to graduate. There were actually jobs for graduates back then. Believe it or not, I know that sounds like foreign concept, but remember we're talking about history now, there were jobs available. I was also being, you know, kind of prodded by a couple of my professors to go into a master's program, which I didn't want to do except that it was in London, which sounded like fun. And so that was really what I was weighing it against was sort of the future right. It wasn't as much about do this or not. I've been doing it for a couple of years and so it was like I was already through that initial risk hurdles. So it was about projecting into the future and saying, what am I trading right? Because we're about to take off on two very, very different paths for three really, I can either start the career, I can continue my career as a founder or I can continue university to one end. I don't know other than more debt. And I think that there's something interesting there in the consideration and I don't think I was wise enough to really see it at the time because I was looking at the start of the journeys and saying kind of like, well, which one of these is most meaningful? Me right now, right? Had I been a little bit wiser, what I would have been thinking about and I think this is one of the most important pieces of risk that's involved in a startup. Is that had I chosen a career or to continue university, which would have just been a slight delay in a very similar career, Right, Go and get my M. B. A. And then, you know, get a slightly higher paying job on the other end with way more debt. But the difference there, it becomes very important in that. And you've talked about this before, if you restart your startup, you're essentially hitting like a 10 year reset button, right? If you start your career that's pretty flexible, right? I can move from one job to another. Often with very little loss or often with some gain. Well, tell me that story that you know about that founder who stopped his one startup and then the next day I had a startup that paid him more money? Tell me you remember

Wil Schroter: that one, You reset? You reset that meter exactly. Right. Let me ask you this, Would you say in your 20s, You understood how long your career actually was. In other words, I think for a lot of us we think when we're in our twenties are twenties are so meaningful. If we don't get it done by 30 something's going to happen. But did you think about your career as say a 50 year window

Ryan Rutan: at least? Right? Like I don't know that I ever really put an end point on my career. I think that I had already washed the notion out of my mind that there was like this thing that you would go and do for a period of time and then I would get the watch and then I would retire and then I don't know, like that wasn't really part of my calculus at that point. I wasn't thinking all the way to the end. I was very much kind of like to be very honest in the moment when I decided I wasn't thinking much beyond the next 3 to 4 months at that point. And it was really as immature as I was like, which one of these three things is going to be the most fun? Right? Do I want to go start a job with Mackenzie? Interesting? Probably not that fun. Maybe do I want to go do my M. B. A. In London? That sounds fun, right? Comes with a bunch of costs or do I want to continue the startup that I've been running for 3.5 years at that point, which honestly wasn't as fun as it was in the beginning, right? At that point it had grown and we've talked about this in other episodes, but had grown to the point where I was now the middle man trying to keep the design and development teams from killing each other and the sales team from making everybody angry and dealing with clients, right? It wasn't this, you know, I'm building stuff anymore. So that was really where my head was at. But absolutely, I wasn't thinking too too far out And I was also 21 at the time. So I was at the very beginning of my 20's. So like 30s was something that was happening to other old people who had Children, right? It wasn't even on my radar.

Wil Schroter: I think that the challenge with, again, being in your twenties, I certainly faced this myself is you've just started your career a good way to put this. And when I talked to a lot of folks in their, in their twenties, I say, look, Let's say you're 24 in your mind, you've been around for 24 years. But as it relates to your career, your career, which let's say has a 50 plus year lifespan. You're only on year one or two, like your career has barely started, you're the equivalent of two years old and diaper.

Ryan Rutan: Yeah, exactly. Haven't even peeled off all that protective plastic that comes with new electronics yet, right? You're

Wil Schroter: out of the box. But here's the thing, the challenge, there's kind of no way around this Is at that point, at an experience level, we don't have that experience to understand what that really means, right? So we do believe, Oh my God, if we hit 31,000 years old, we actually believe that because in the context of what we know so far, we know so little and again, we'll age up quickly. However, one of the challenges that we don't have When we're in our 20's is we don't understand that our twenties are a magical one time, get out of jail free card and I'll never forget, a friend of mine said it to offend me, so let's I'm gonna call it what it is. I was like 25 years old, business was going well, whatever. And he said to me, he's like, you're not that smart, I'm like, okay, thank you. He said he's also right, but He said you've got the Gary Coleman effect, which is such a dated reference. Gary Coleman was a child star of different strokes from the 80s, he was, I don't remember how old he was in the show, but like let's say he was like seven on the show, his character was, but he was like 15 in real life, he was just a tiny man. And he said, you've got the Gary Coleman effect basically, if you do anything well you look like a genius and if you screw up nobody cares, right? And it was such a perfect characterization of what your twenties look like, right? If you do something extraordinary in your twenties, the reference point is always look how young he is, right? Mark Zuckerberg was always about his age, not his accomplishment. And so on the flip side, if you screw something up in your twenties, kind of, no one cares, I'm not equating that to, it doesn't matter, it's your life, of course it matters, but you do get a bit of a get out of jail free card For being in your 20s. And I would say the only thing that you can do to screw that part of your life up is not account for what a one time shot that really is the most consequence. Free decade of your life, you know what I mean?

Ryan Rutan: I don't love to pull sports analogies in here, but it's the first half, right? You can be down by a couple of points in the first half, you can make a couple of mistakes in the first half, you have plenty of time to recover at that point. And I think that that gives you a lot of risk tolerance,

Wil Schroter: But building that it's not even the first half, man, it's not even the first quarter. I mean if you've got a 50 year run of your professional career and you hit 30 numerically you barely made it through the first quarter. Well, that's

Ryan Rutan: all the energy substitution at that point.

Wil Schroter: Yeah, in that case, the four quarter analogy holds up, but look, my point is we always talk about startups and folks in their twenties, but I think we should dissect why that age is so paramount again. And to be fair, that's a relatively new phenomenon, right? People used to start their businesses much later in life when they had accumulated some cash and some experience and worried it to go off and do that. Maybe had a

Ryan Rutan: chance, what the hell they were doing now? We're just like, go figure out on the way

Wil Schroter: and it's mainly because of technology, but what have you, but what's going to change? And I think this is gonna be the core thread as we progress through each decade. You have the fewest consequences you'll ever have, but you have the least amount of experience to know why that's important.

Ryan Rutan: Of course go back to what I was saying, I was being very honest, I wasn't looking at future risk. The risk that I was assessing was which one was going to be the most fun, right? What's what was in my mind right now? That's what I was trying to figure out, right? It wasn't, you know which one of these is gonna be the most lucrative? Which one of these gonna have the most chance of positioning me for success. It was like, which one of these do I want to do the most, right? That was the only trade off I was worried about, which isn't much of a consequence, to be honest, there wasn't really a wrong choice at that point. And I think that's something else that's interesting. It doesn't always exist right. There are choices I could make now as a 40 something year old that absolutely have long term impactful consequences. The decision I was making them, it would have changed outcomes in my life, but I don't think it would have put me on a path towards success or failure of some sort right would have just meant different navigation along the way.

Wil Schroter: There's another way you can look at that and say, well, hey, if I fire my get out of jail free card and I miss, I never get that again. So it's 10 times more important because I never get to take a swing like this again. And I think that there is some truth to that again. If you Go all in on a startup, let's say you started at 22 And that 28, you know, you wrap things up and it didn't work. Yeah, that's a tough time to get back. However, the one thing again, we tend to not know when we're in our twenties because we haven't experienced it yet is that composition of experience that we gained is now going to be our baseline for our next next next gig. And what we kind of failed to process is we didn't have anywhere near that, like we were geometrically less qualified six years ago when we started this thing. And I think one of the things that you start to understand as you progress through your decades is you don't have to learn ship twice. Right? In other words, how

Ryan Rutan: many decades? You know, I'm

Wil Schroter: not saying you won't make the mistake twice, right? Yeah, I'm saying you won't have to know why it was a mistake twice, Right? If you've gone through a massive round of layoffs, you don't need to do that again to understand how painful it is. You may do it again. But the first time you do it is all the education you need and there's like a dozen things in startup life that you'll go through broken funding funding. Layoffs, you know, a co founder dispute et cetera, that once you've kind of earned that skill, if you will, whether you wanted it or not is going to be geometrically more useful as you go into your next gig. But here's the trick. You generally couldn't have had any of those experiences earlier in life. You know, the likelihood that you got them in your teens pretty low, right? If you did a great for you. But all I think that's so important our twenties because it's such a transformative time is that our downside, our kryptonite Is that we just don't understand how much time we actually have or how valuable and unique this time is, not to say we can't do it again. We'll get to our 30s in a second. But that this is our shot to basically scrimmage our 20's is a scrimmage in our career and we get to funk up and reset because the big game is yet to happen.

Ryan Rutan: Alright, so that said let's talk about our thirties then and you know, we both went through quite a bit in those early years in my case, within the first two years of my 30s. So between 30 and 32 I orchestrated an international move. Well a marriage than an international move first kid and we started startups dot com. So if you want to talk about like a whole bunch of different things being thrown into the consequence matrix, I'm not sure I added a dog. I'm not sure what else I could have done in there to to complicate things more and it really did change the analysis significant as you look at all of those things happening at once. I mean yes there stressors and yes, they take a lot of time but take that off the table for now. It wasn't about whether or not we could manage those things. Right, overly optimistic guy. So I always assume I can manage everything. But it was about what were the change in consequences depending on the various outcomes. Right? I'm not so optimistic that I assume everything will always turn out for the best would be perfect. So I was looking at downsides right? I'm thinking like okay we're starting something having just come back, like we haven't stabilized our lives here yet, Is this the right time to do this or not with the baby on the way and then the baby arriving. What is the trade offs there? And I know about the trade a bunch of my sleep, so I'm not going to be at my best. So what sort of risk am I imposing on everybody else involved in this business? Just based on the fact that I may not be at the top of my game. What am I trading in terms of life with my family? You know, my at that point my relatively new bride and my very, very brand new baby knowing that they're going to be nights where I'm going to have to be burning that midnight oil being away. Right? And so how did that change? You know, and it was significant? Right? Again, like coming out of the 20s were like, don't want to say nothing mattered, but I had this, you have this sense of invincibility, right? There's and when I was only responsible for myself, alright, so if I screw something up, it's just for me now, if I screw something up, there's thrice the consequence. And I got 33 people involved in this equation now and that's a big deal. So that started to weigh a bit more heavily in terms of, you know, what does this mean for our family? What should I be thinking about that? I wasn't thinking about in my 20's, right? What sort of planning needs to be accounted for? And I think the other thing that was really was really shocking and, and it was just the way it happened in my life, but there wasn't a transition period and it wasn't like, oh, I ramped up into this, it was like, bang, bang, bang, all these things happened. Of course they were decisions and there were decisions I made. But I don't think I fully accounted for the gravity the weight that adding those things in this rapid sequences I did to my life would change how I thought about starting a company running a company

Wil Schroter: at its core. Ryan, you're talking about this is the first time you had a consequence to your actions, right? In other words, I don't want to dismiss consequence. I mean, obviously creating financial risk as a consequence, but these are consequences that, aren't you? Right. And so I think a lot of us, you know, prior to this kind of dawn of consequences, if you will when we're talking about families and mortgages and everything else that comes with that prior to that, we know it's coming and there's a part of us that's smart enough to be able to look at that and say, okay, you know, I should probably maybe take a few swings for the fence ahead of them. But here's the interesting thing for many of us, we make those commitments, usually in our late twenties, statistically late twenties and into mid thirties. And it implies that we only get A 10, maybe 15 year window to be consequence free as it relates to other people until all of a sudden we got the entire rest of our career where we have what's essentially geometrically compounding consequences because, you know, families, kids, retirements, mortgages, etcetera. All this stuff just gets bigger over time. So the stakes just keep going up

Ryan Rutan: and some of them are permanent, right? Whereas the consequences early on and there were consequences, right? We both face them letting go of employees, you know, a parting ways with co founders, lots of things had consequences early on, but there were temporary consequences, right? Yes, it was awful to have to let people go, let them go, did our best buy them, tried to help them transition onto something else, set them up for success and off they go. It's not quite the same when you're talking about impacting your family, right? You're your own livelihood, your wife, your spouse, your kids and, you know, their futures, their educations. There's a much stronger sense of permanency right? That if I get this wrong, that some of this stuff gets etched in stone instead of, you know, written on paper that will eventually just kind of float away out of my life.

Wil Schroter: I think where it hit me. And I think this is similar to you, I specifically remember sitting in our offices at the dawn of startups dot com and I got a text message from my wife and she was, hey, what time are you coming home for dinner? And it was so bizarre because it was just this life moment where I was like, well, what do you mean? Because I had never come home for dinner, I would just work until, you know, midnight or whenever the hell I'd worked for, like, my entire career, that was pretty normal. I would always eat dinner at the office or what have you

Ryan Rutan: tonight, What do you mean coming?

Wil Schroter: I was like, and, and so it kind of threw me for a second because she was like, yeah, you know, dinner is at six and dinner had never been at six. I didn't know you were allowed to leave the office and I always have to caveat that I'm not proud of that fact. Like looking back, it was total jackass move. However it occurs to me to, it was basically the first time my daughter was going to be at dinner, you know, had a newborn daughter and she was gonna be at dinner. Incidentally she turns nine today. So if you give a sense for how long that road has been,

Ryan Rutan: it's officially in the podcast now you're a

Wil Schroter: star. Well what was interesting to me though, it was like this entire flash forward, right, this highlight reel of the future came into effect at that moment and I was like, wait a minute and I'm doing the math, this is such a boneheaded thing, I'm doing the math and I'm like, okay, wait a minute, I'm 37 at the time and if I fast forward that means I won't be able to stay home and work all night tomorrow or the next week or the next month or the next year or the next decade. And I was like, oh shit, like all that extra energy that I used to have, like all those extra reps that I could just put in weren't free anymore in should I have thought about that about nine months earlier to that I should have processed this earlier but damn, I didn't and it all hit me like a damn avalanche at that moment and like everything in life changed. Like after that text message, my wife was just wondering what I wanted for dinner, but for me,

Ryan Rutan: 18 plus years into the future,

Wil Schroter: I don't know if this is a good analogy, but sticking with our sports analogy, I looked at the scoreboard and saw that I was down by 28 points and I had one quarter left now and again, that's a ridiculous, you know, kind of comparison because of what I just described, how much time you really have left. It was also a reflection of how young, I still was relative to my whole career. Yeah,

Ryan Rutan: like a lot of consequences that we face and again, like until you get to them the first time they just seem like hurdles, but I remember right around that time, shortly thereafter you and I both started doing some charting right? We started looking at our days, we have different spreadsheets but nerds that we are, you know, we both developed some spreadsheets and some charts and we started to look for those golden periods within our day. When are we most productive winner? You know, one of those times where I can, I'm, you know, I'm a little out of gas and I can, I can slow down and we started to optimize our days. Alright. And so that never would have happened without that consequence in my opinion, we never would have been just like on our own decided, hey, I need to figure out how to make both these things work together. I should optimize my day, said differently if there was nothing after work to care about, we wouldn't have done that. Right. And so

Wil Schroter: the first time your time had consequence,

Ryan Rutan: right. Exactly. My time had consequences prior to that. And just in terms measured only an output.

Wil Schroter: Right? Right. And only

Ryan Rutan: in the context of the startup. So you know, it's interesting, but a lot of these things are really important moments of growth. They're not just restrictions. They're not things that are just, you know, these aren't reasons to start or not start a company, they're just things to consider, right and honestly there's been so many positive changes if you look back at either of us and the stories that we tell about this, the early days, the early decade, you know, the second decade, we've gotten a lot better at this in terms of treating ourselves like humans within our startup companies. And I think some of that's maturity, some of that's just the calluses from having run barefoot over the glass for long enough that we realize there's probably a better way of doing this

Wil Schroter: actually, Ryan stick with that a little bit because I want to really start to highlight not just the consequence, but some of the pros. So when we started startups dot com was about nine years ago. One of the huge advantages we had going into this is we have been around the block so many times by that point. You know, for me it was my, my ninth startup, we knew exactly what to do and what not to do now. That's not the same as saying, we could predict the future, right? We had no idea how decisions would play out etcetera, nothing like that. It was more like you knew the heartaches were coming and you could just kind of roll with the punches in other words, you knew you were going to make bad hires, you knew you were going to develop ship product, you knew you were going to miss a funding round, we didn't raise any, but like you knew those things were going to happen and you kind of knew what it looked and felt like when they came down the pike now prior to that and I think this is a huge distinction. It was always knew when a funding round broke, it's like, well that's never happened before, like you know what does that mean? Right? And we could never see around corners and I think this gave us a massive, massive advantage and having that experience and starting later if you will because we could take all that experience and actually do the one thing I think you and I are probably most proud of which is define a culture that worked for us and not against

Ryan Rutan: us,

Wil Schroter: right? I remember us sitting down in the conference room and saying we don't want to build the company where our kids never get to see us, right? Like that's not okay. A lot of us grew up with And we don't want to replicate that we don't want to work with jerks. You know, we had this whole kind of 10 commandments if you will and we stuck to it and I think that was a huge reflection of our relative maturity at that point in our careers

Ryan Rutan: having gone through the converse earlier in our careers, which is, we did work with jerks and we did spend time away from our families and we did all these things and so yeah, it's definitely, you know, kind of a, it's a learning experience that then you can apply. So yeah, it doesn't necessarily lower the risk. But I think pairs you to navigate those risky waters a little bit more. It's funny but you know, as we talk through this, I'm thinking, you know, I don't know that you're necessarily more risk tolerant when you're younger, you're just so unable to see what the potential risks are that they don't bother you when they hit you, they hit you just as hard remember? Yeah, you haven't lived through that. You just don't know right? You just don't know it's not right. We talked about this, Gosh, 2, 3 episodes ago in the context of, you know what happens, what do we lose when we sell our startup and write, one of the things that I wanted to bring up in all of that was that we do typically go back and start something else, right? But I remember, you know there's that period right afterwards were like, I don't know if I want to do that again, I don't know if I want to do that again. And I think that it's less about risk tolerance as a whole and more about knowing exactly what the cost of going from start to that finish right? If you were lucky enough to exit one and you'll probably start another one. It's understanding at that point all of the things that were given up as you're spending it as you go, you don't feel it nearly as much right. It's kind of like, you know when you're, you know in your twenties and you, you went out on a weekend, you had 100 bucks in your pocket, you're spending a dollar by dollar, you don't feel it now, you wake up on monday and you're like, I don't have money for lunch, but I was only spending now I know what the consequence of that was right at the time, those incremental buyers didn't seem that important to spend expenditures of energy and time and money and whatever didn't seem consequential until you add them all up and you look back and you go, damn, that was a lot. And that's painful. And I think that's something else that happens as we, as we mature, we have a much better understanding simply through accounting of what this actually costs. And I think that definitely changes how we feel about starting and running companies as we get more mature.

Wil Schroter: So let's step it forward a little bit, you know, let's move on to that next decade. Getting into our 40s. Why do you keep

Ryan Rutan: trying to make us older will

Wil Schroter: what here's what I thought was really interesting. It was the first time I started to see a lot of my friends who were founders turn down opportunities because they just couldn't digest the consequences. In other words, they were saying, hey, look, that sounds really cool. I'd like to get involved. But I can't not, I don't want to, but I can't write like I'm at a point where my expenses are such, my liabilities are such that they have to be serviced, right? I can't work for free, so to speak. You know, and make it up later. I don't have that ability anymore. Not only can I not risk it, I can't even afford to take risk, which means for the first time, even if I believed I could make it up later, if this fails, it doesn't matter. I don't have the ability to start. And I think that's a dramatic departure from the previous decades.

Ryan Rutan: There is a limit to that. As you said, our liabilities continue to grow along with our experience, right? And experience on, on both sides of that, right? In terms of our ability to execute against things like we may get better at doing all these things, but we also have the experience of those costs and we have the experience of what happens when liabilities aren't met. And that's painful, right? We don't, we don't want to put ourselves through that particularly that stage. There's also the sense, you know, we've just been running long enough now, do you really want to engage In a sprint as you've been running a marathon for the last 15 2025 years.

Wil Schroter: Yeah, because you're in

Ryan Rutan: the middle of that

Wil Schroter: marathon at that point. It's like, you know, depending on who you are, if you have a family or what have you, you're very likely like half of your week, so to speak. You're, you're waking week is already occupied. You have a full time job, right? That doesn't involve getting paid. And that takes an incredible amount of energy at a time when you're starting to have less energy, right? You just wake up or go to bed with the same kind of, you know, nonstop energy that you had before. Not only are, you know, we just generally more tired, just kind of no way around it. Again, the liabilities create a bit of a high water mark that if we can't get over those liabilities to even start, we don't get another shot at this. Now there's another side of it, it's the first time where the amount of years we have left, I'm talking our peak working years. I'm not talking about our entire lifespan is starting to go down. So I'll give you example early, my forties, a friend of mine came to me and he's actually a couple of years older than me and he had wound down a startup that didn't go particularly well, but he wasn't in dire straits, but he was looking for a job. And so he said, hey, if you know anybody looking, you know, here's kind of what I've done, etcetera. And I thought to myself that I'd never thought this before, you're too old. What I thought was of all the jobs that I know you gotta figure startups, I wasn't thinking Fortune 500 they wouldn't hire you right, They're looking for somebody that has fewer liabilities by way of that, a lower cost base that can put in more hours in. Like basically the stuff that you bring to the table, the experience etcetera Doesn't outweigh the raw energy and cost if you will and risk tolerance of someone younger than you. And so in this world you're less employable and maybe in the Fortune 500, you know, more traditional corporate world, you're also less employable. But it was the first time I had thought of him as being less employable and it kind of messed with me because I started to understand the consequence.

Ryan Rutan: Yeah, it's funny, but I don't even tend to think of my founder friends as employable at all. I just don't think of them in that context until something like that happens right. Like it's not like I'm, I'm constantly thinking like, you know, I wonder what joe would go and do if he were, it's you just don't think about it right unless there's some reason that I've been given, like things really heading south. He's, you know, they're starting to talk about it, they're asking, yeah, it's rough, particularly, you know, depending on the position that you've been in, right, as a founder so much changes if you have to go back that direction and take on a role with another company. It's not to say that we're not employable or or that, you know, we can't tolerate that environment certainly wouldn't be my first choice. Right?

Wil Schroter: Well, sure. But also I don't want to go too far and attention of founder employability, I actually just want to talk about more at that stage in your career. The people that you're back in the market competing for jobs with are likely one of two people either people that were career corporate people, in which case they have a very defined structure of, of progression, in which case they're making, you know, maybe hundreds of thousands of dollars because they went through the logical progression. Their resume reflects that or you're competing with people that are 15 years younger than you and can work for almost any amount of money by comparison either way you lose. And so it's really difficult from that point forward and again, we'll get into fifties Plus it's really difficult from that point forward to drop back into the job market and get a meaningful kind of reset where it's someplace that's acceptable to you. It's the first time it's a consideration. It may not apply to you, maybe you're great at finding your next job, but it's the first time you have to really think about it,

Ryan Rutan: you know, well, something else is occurring to me right now that I'd like to talk about for a minute, we've essentially used ourselves as the archetypes for this thread today. There's a small challenge with that, and that's that not everybody started for the first time in their twenties and I think that does present different challenges, right? There are people who, you know, we're talking about this as a continuum, right? As if you started in your twenties and then here's what it looks like in your thirties and now you're into your forties. What if you didn't start until your thirties? What if you didn't start until your forties? Right? I think that brings a very different perspective to this entire conversation, I'm 100% sure that there are people out there listening right now who are saying, well, you know, I'm 43 I'm thinking about starting my first startup after this long career path that you talked about, I've been corporate for 2030 years In your mind, how how does that change things? Right, let's just look at the 40s, because, you know, in your twenties you don't have much of a career to lean back on, arguably in your thirties, you're still kind of in that development phase, but at 40 you could have had nearly a, you know, a 20 year career in a field, which brings different resources and different risks.

Wil Schroter: Yeah, well actually, I kind of see a different challenge often when people have kind of hit it at that point, it's as simple as this. I'm making so much money in my corporate job. That it's really hard for me to risk that. I see. I mean, you know, it's funny, a lot of my friends from high school are attorneys and hating attorneys, but they're far enough along in their career that their partners, etcetera. And like, well I can't leave, you know, everything that I've built to go do this. But short of that there is this concept that there's a much more costly break up period of kind of parting from that career track. But if you did, I think your point is, hey, you've probably built enough resume that if you took a five year window and put some risk in, you could probably come back to that in relatively short order, which I would agree with. There just aren't that many people that have like that perfect of a resume that they can jump out and jump back in, especially at that age, totally gracefully.

Ryan Rutan: That is a fairly transferable skill, right? And in the sense that not transferable, but in the sense that you could leave practice and then go back to it I guess. But I was really looking at is more, you know, something's working for, you get some things working against you. You know, at that point, maybe you already own your house, right? Maybe you already own your cars, maybe your liabilities are such that they're not going to present the same challenge That they do if you're creating those liabilities as you're creating your startup, which we did in our 30s, right. We're taking on the liability of the company, the liability of a family. The liability of mortgages, of cars, of all these things. If you're taking on a startup at a point where those things are either, you know, less of a challenge or not a challenge at all, certainly has an impact. Right? Of course, the energy, the family, you've got some of these other barriers that are pre existing. But, you know, I think it's, it's worth at least mentioning that that's a different discussion than the one that we've been having today, which is really about how does it change over time if you're sort of a career founder versus somebody who jumps in at a different point in the

Wil Schroter: Game? I think being in your 40s and starting a company, maybe one of the most challenging times to make those decisions. And I'm not saying that that it's better or worse or in any way, I'm just saying, because you've kind of gotten to this interesting place where all your liabilities have typically stacked up to what they're going to be, maybe in your fifties, you max out your liability is a little bit more because depending on how old your kids are, you're getting into college educations and things like that, but it's the first time and I'll speak from this firsthand that you're also thinking about retirement, right? Not like, hey, I can't wait to retire, Maybe you can, but more so hmm, I can't just bet on things and have nothing come from them because I'm starting to look at, I've got a little bit of time, but I'm starting to look at a window where if I whiff over the next seven years, let's say, How is that going to impact me 20 years from now because I gotta start putting stuff away and take that further. What if I start taking away from that? What if I'm pulling drawing out of 401K or any of the other, you know, small retirement that I've started to build up up until now, how do I replenish that? So not only are you talking about present day consequence, but you're now talking about a very numeric consequence on the horizon that you're not sure you're going to be able to fix, which, again, this, this starts to stack up, it's far enough away that maybe you can do something about it later, but it's the first time, it's even part of the discussion Alright,

Ryan Rutan: it seems like it's time to move on to the golden

Wil Schroter: fifties.

Ryan Rutan: This is a, this is an interesting period, right? This is where you get an interesting confluence of a closing window in terms of just time, right? You know, we're getting older there, there is an hourglass in effect here, less time to get things done And less opportunities that would exist outside of our startups, right? We talked about this, we discussed the 40s, but that job market is going to become even smaller, right? And the amount of time you have to recover even smaller. So those two compounding factors make this a very all these sort of interesting time. But you know, well you're already starting to think through this, right? You're approaching that point, you're not 50 yet, but you're you know, you're looking at that horizon and your what are you saying to yourself at this point in terms of your risk tolerance, your appetite for startup, all that, how if is it starting to change?

Wil Schroter: I think it's a bunch of things because this is crazy to think man, but there are aspects of my life that just haven't been an issue before that are now well within my focus, for example my health now when I go to the doctor, it's like the last three doctor appointments and he, it was like an eye doctor or whatever other doctors and they no longer start with. Well that wouldn't be a problem because you're obviously still too young. They now start with well basically, you know, starting with with this age you really do have to be concerned with X, Y Z. Like I just learned about what cataracts are like come on man, but but it's real and again it starts to put things in perspective that you're not going to be forever young, you're not going to have kind of the energy or you may have other issues that are kind of either developing now or down the line that are absolutely going to be part of what your considerations are right on top of that. You have, what will likely be depending on kind of your era, if you will

Ryan Rutan: the most

Wil Schroter: expensive part of your life across numerous vectors, it's the first time your dependencies have dependencies, right? And don't necessary mean grandchildren. I'm talking about aging parents, I'm talking about other people, you know, family members, etcetera that may need your support. All of this comes to pass. And so now when you think about taking on risk, your number of dependencies, your number of challenges to be basically able to overcome that risk or really what we're talking about is recover from it become as big as they're ever going to be now. That doesn't mean you can't do it. It just means that the decision criteria become exponentially

Ryan Rutan: bigger. It's already starting to happen for me, my wife put a word to it. She called it the sandwich generation where we are now stuck between the needs of our aging parents and the increasing and expensive needs of our Children. And I guess that makes me the aged ham in the middle of that sandwich. Um and it's absolutely true this year in particular was a challenging one for me where those liabilities from parents began to kick in and not just in terms of money, but in terms of my time and focus and and some things that happened this year that I had to deal with that definitely weren't expected and absolutely impacted my ability. And I tried to fight it as much as I could and say, you know, I'm just, I'm still going to be present, I'm here doing all the things I need to do. Um and largely that ended up being true, but it probably took years off my life because I went back to having to, you know, superman my way through some stuff that otherwise wouldn't have existed, right, definitely wouldn't have existed in my twenties or my thirties. I assumed that this would happen a little later. I thought this would be part of my fifties. I think that what we're talking about it now, but for better for worse happened a little earlier in my case. And it's very real, right? And I think the the other thing that happened for me was that I am now expecting more of that, right? And so there's a part of me that's not fully exhaling at any point because I'm holding back just a little bit of breath to be ready for that next shot. And I don't know when it comes, I don't know what form it will take, but I think you can almost assume At this point, right? And we were talking 50s, I got there a little early, but there's an expectation that there are gonna be things that take me out of the game for a quarter or you know, part of the time, like I'm gonna have to be subbed out for a bit. And that's tough to acknowledge, right? We're used to being able to play the whole game and not have to think about how our own participation gets impacted here. So I think that's something that it can happen at any stage, right? We've had a period, you know, where you went down pretty hard, We were worried about you and you recovered, right. But I think those things that was a big surprise. I think these things almost become certainties. And I'm not sure really plan around, it definitely wouldn't be aware of it.

Wil Schroter: Well, okay, so stick with that. What you're talking about is at that age, you know, ship is going to happen. You just don't know when and you don't know how severe

Ryan Rutan: the mileage on the car has gotten high enough that, you know, the bills are coming

Wil Schroter: right? Absolutely. In other words, if you haven't run into an issue yet by then and you know, hopefully you haven't, but likely you have, it's really difficult with all this staring you in the face to say, Yeah, let me let it ride, right? And I'm not saying you can't or you won't, I'm just being very real about how the situation has changed and how as a founder, looking at, you know, hey, what should I do next? It would be impossible to overlook those things. And more importantly, it's insane to think that that decision set is the same as it was in your twenties, right? So when you say, how old is too old to be a startup, It's not that 50, 60 plus is too old to start a startup. It's just saying that the criteria that you have to choose from in order to make that leap is dramatically different. It's not a single continuum. That's the same for everybody. And I think that's the part that kind of gets taken out of the conversation.

Ryan Rutan: Okay, so sure, the decision matrix changes, there are definitely new challenges that wouldn't have existed any other point, but there's also some upsides to this too, right? Like as we've talked about each kind of decade, you know, each new era that we move through, we do gain some things. We gain experiences, you know, we become less reactive or less shocked by by by some of the consequences. But there's also something to be said for, you know, if you are thinking of starting something in your fifties um and talked about this before will where there's a little bit of pressure, right? There's there's a little there's some sense of urgency that if not now when Right am I going to wait until I'm in my 70s to do this right, Right. We've also gone through a whole lot of life discovery at this point, and I think one of the challenges, right, like one of the reasons that young startups pivot so much, they don't know what the hell they want to do right there end up like you, you know, I think I'm excited about this, I am passionate about this, right? Well, it turns out you're infatuated with it. Um and then you move on to something else. I think the likelihood of that happening, If you're somebody starting in their 50s, you probably got a really clear reason for why you want to start it. You've probably got a really clear reason, clear what you want to do, and hopefully you've accumulated skills that point you towards a fairly strong ability to execute against those and those three things I think are hard or nearly impossible to have At these earlier stages, you can develop them, but it's constant work in progress where I believe that at that stage, if you're starting in your 50s, you probably have some of these things in hand.

Wil Schroter: Yeah, I agree. And I think there's some other things that are huge, huge assets to what you can bring to the table. I'll give you one your network, you know, when I was in my twenties, let's say, and all the people that I had met, generally speaking, my peers were all, you know, in their twenties and they had the crappiest job they were ever going to have. Now all my friends are ceos of companies, they're like legit decision makers of all these major companies. And so if I need to call in a favor or make a connection, you know, I've just got this amazing robotics that I can draw down from and that's just a factor of time, right? You know, just my peers are just older and more responsible theoretically. And so I think, but I think that has a massive accelerating function, right? I also think that at which point we're looking at the business as maybe the last business we're going to start because we're not dying to reset the clock and do it yet again, I think we make better decisions, You know, I mean, I think like with startups dot com because it's so important to us that the mission and what we're trying to do is so important to us. We can make long term decisions. We can say, hey, here's something that we think is really important because it's the right thing to do for the business, not necessarily, hey, we think this will just happen to add value so we can flip it and get out of it as fast as possible, which was definitely my m o for everything before this. And I think that kind of long term thought process or planning is incredibly helpful to a startup. I don't think startups should be so shortsighted in so short minded that every decision could be about how do we get out of this as fast as possible? I just think that's a it's a miss, but something what I've seen is we get far less of when you get more mature founders.

Ryan Rutan: I think so, and I think that's a that's a function at least partially of two things, and I think those two things are related, which is passion and mastery, right? And I think those two things together when I hear people talk about passion, but I see they don't have mastery than what I call that infatuation interest, right? It's something you're very curious about want to chase down, but I think that when you truly have that passion in some level of mastery around a topic, the likelihood that you want to keep doing that thing and you keep benefiting from it more. And I don't just mean financially existentially right, that you get deeper into a practice that I remember the first couple of times I meditated and I was like, okay, I'm just sitting with my eyes closed, right? Not a practice I would have continued had it never changed as I got better at it, as I continued as I developed some level of mastery for meditation, I started to get more benefit from it and I realized this is something that I want to continue. This is something that will benefit my life playing soccer, playing Jujitsu, right? If Jujitsu was still the same as it was my, my first lesson where in 30 seconds the professor managed to choke me out and put me to sleep. Like I probably wouldn't have kept doing it if that was the outcome every time, Right? But as I mastered it more, I began to enjoy it more, understood the nuance of it and that the same thing is true as you start to exercise whatever that muscle is, that's the core of your startup, right? I think you understand that doing this over a long period of time, hes me back in different ways. They're hard to see when we're young and we don't have enough experience to see over that horizon and say like this is how this benefits me in the long term.

Wil Schroter: I think that for most founders, right, as we start to think about in kind of grand scheme of of all these different progressions of all these different decades and was kind of thinking, hey, you know, when is it too late? I think the answer you and I would agree with your net with everything we've just talked about is it's not about being too late, it's about hitting a point Where we're not willing to take on the risk or costs of doing this. So look, if you're 75 and you're saying, Hey, now it's time to start something and you're willing to take on those risks doesn't matter. Yeah, maybe you have a little less energy, you have a lot more experience and you can stay focused on it. So I think you're perfectly in great shape to be doing that. But I think what we really need to be thinking about as we progressed through our careers is kind of that if not now win, but more. So if I wait longer, will the benefits of maybe a little bit more experience or a little bit more cash really outweigh this nonstop progressing consequence. That's only to get bigger over time. You know, the more time that goes on, that consequence is only gonna get bigger. When will it be too big? And that's when it's too

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

Wil Schroter: You'll thank

Ryan Rutan: me later.

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