Startup Therapy Podcast

Episode #205

Ryan Rutan: Welcome back to the episode of the startup therapy podcast. This is Ryan Rotan joined as always by my friend, the founder and CEO of startups dot com. Will Schroeder. Will we have both done the cat thing here. We've lived several lives throughout the course of our, of our startup journey, right? We've lived and we've died through a few of them. But I think it's, it's a conception right? In, in our space that whatever we're doing now is like the one thing and we got to get this right? Because there's never going to be another chance and sometimes that's true. But like, how many, you know, resets do we get in this thing? Right. Is this contra where we just get to three lives or is there a cheat code where we get 99? Like, how many lives are we? Actually, I

Wil Schroter: missed contra so badly. Me

Ryan Rutan: too. Two buttons. That's all I

Wil Schroter: needed so far. I've had like three entire founder lifetimes and like, I'm older, but I'm not that old, right? Like three entire epics of like massive amount of ups and downs and like basically an entire lifetime's worth of life. Three times and I'm not even at half time in the game yet. Right. So I've got a lot more of them to go. I think where this gets a little bit tricky. And I talk to my friends about this, you know, founders and such when they're dealing with, you know, they're wrapping up a startup or winding down a startup, whatever. And they're like, oh my God, man, I guess I'm done. I'm like, whoa, hold on, pal, I'm like, you're not even remotely close to done. You're 34 years old. You haven't even finished the first quarter yet. This game is far from over. You've got a lot more quarters to play. And so I've always kind of thought about this concept of a, a startup lifetime in a different context. In, in what I would consider typically 7 to 10 year cycles. In 7 to 10 years, most people who build a successful startup, they fail much quicker. But in 7 to 10 years, most people that build of a successful startup will, I've done it in that time period. Now, some of us will stay with the startup and go on and grow and all those things. But honestly, most people don't, most people, if they do something, they're gonna exit it, that's their timeline. That is one tiny period in the grand scheme of your professional career and you get lots more of them. And I think that last part Ryan, that you get lots more of them. Part is what we really need to instantiate and kind of unpack a little bit today.

Ryan Rutan: Yeah, I think that makes sense. Yeah, I, because the focus needs to be and the fact that, yeah, there is a, a life cycle for this startup but it's not inextricably tied to your life cycle. Right. We've talked about this in, in a couple of different ways across other episodes. But there is a need to separate yourself from the startup company. You and the startup are very much tied together, especially at the early stages, but you're not the same thing, right? And so regardless of the life cycle that the startup goes through, you have a separate one, if you don't call us, right? We need to talk about this because you should have a separate one and, and you get, you get a bunch of them to your point, right? Like look at some of the founders that we know who are on their 4th 5th, 6th thing or, you know, just some that have gone through like a ton of evolutions of a singular business, right? To your point earlier. Sometimes people start something and they stick with it. But even within those, we see life cycles, right? You've got a buddy in Columbus, it's a brick and mortar business, but he's been running that thing for like 50 years now, but it's also gone through a bunch of evolutions, right? It's grown exponentially. Over the years. Right. And lots of stuff has changed and each one of those is its own kind of life cycle comes with its own challenges, comes with its own rewards. But the point still being there were a bunch of them. Right. We all get a bunch of

Wil Schroter: them. I'll give you some examples. Give it my, my own periods. I'd be curious to hear yours as well. In my twenties, in my twenties, I had an entire period that spanned from, I've never done a startup before starting something for the first time. I guess I'm dropping out of college, you know, all of those things to finishing with us having a massive exit, two ends of the spectrum I would have never guessed, would have never pieced together. Ok. That's just one fast forward again. I'm kind of neatly packing them in there, but they're a little bit off in my thirties in my thirties. I go ahead and I start seven more startups all in that same time period. Terrible idea, by the way, terrible idea. And within that time period just, and I'm just using companies as book ends here, but there's a lot of other life there. I met my wife, I got married, I had my kids, you know, I had a heart attack like a lot of things like all happening in that same time period. Right. We raised money for a bunch of companies. We sold some companies, we failed some companies, like a lot happened that was like barely 10 years. Fast forward the next 10 years, essentially. What would end up marking into my forties where I'm holding on to now? We do startups dot com. Dude. Think of how many things we've done in the last 10 years. How many life events you and I have had how many, you know, ups downs crazy misadventures. Think of how many people have worked here, right? That time period. I mean, like we have whole epics of whole staffs that don't work here anymore. Many that do, which is kind of cool, but like whole staffs of people that don't even work here all entire lifetimes and you know, fate willing. I've got like three or four left to go. And so planning around that like this is a longer game I think is tough when you look back at how many distinctive lifetimes you could picture what comes to mind.

Ryan Rutan: Yeah, for me, it's, it's at least three, maybe four, right? So there's, there's kind of, I I'll work backwards since you work for it. I'll work backwards. So there's the startup dot com period now, right? So if we back up to before that then, and it's interesting too because there's is some overlap in personal life cycle and startup life cycle at times. So for example, you and I around the time we started startups dot com both had our first Children, right? So those synced up, I was gonna say nicely. I'm not sure that's actually the way I would revisit that. Right. But like in that, at that point in time, things were, were sort of synchronous, right. We were starting those two new things at the same time. And so they felt like there was a beginning and they were together, you moved to the, the, the period right before that, I was in this kind of state of flux between Europe and the U SI had just gotten married and we were changing continents. I had the one time in my life, I left the entrepreneurial space to go work for a large corporation and then came screaming back to the startup space. And even that wasn't really, that was still pretty entrepreneurial. Uh If, if I'm, if I'm fair about it, that period in time was interesting because startup life and personal life did not line up. And that led to some interesting challenges later, right? That was the point at which I met my wife when I wasn't in startup mode, right? She felt love with not

Wil Schroter: why you met your wife.

Ryan Rutan: Yeah, exactly. I had time. I could dedicate her like I could, we could go out and do things. I wasn't poor as a church mouse, right? There was a lot of, a lot of, a lot of differences. And so that was another very distinct period in life was that kind of like between start ups and prior to that was like the twenties and before that, the teens where there were two or three different companies and in that period of time and there was also for me, university. And so some of them again, like there were some overlap, some crossover and those were often the really hard periods to manage for me. Right? Because I was essentially running two different lives at once. There was the life and life cycle of the startup and me in it and the life and life cycle of university, for example, and me in it and that made things that much more difficult because I was trying to balance these two parallel lives. They started at different times. They ended up ending around the same time, graduation, nearly coincided with the sale of the first company. And so that then made a much easier transition into that next period. But yeah, very, very similar. I, I think that and maybe this is specific to founders, I'd be curious if other people do this, if the book ends of their chapters in life or their lifetimes are job related or career related or if there's something entirely different. Because certainly for me, when you ask me, it, the immediate points are like, when did I start that? When did I exit it? When did I start that? When did I exit? When did I start that? When did it fail? Right. Like that's, that's how you keep track of time.

Wil Schroter: I think that what's interesting too is that you've got these whole epics of life that we keep mentioning now, early in our careers, let's say when we're our twenties, you know, our kind of our, our first quarter, if you will not even that we're missing it all the time. And every time I have these conversations with folks, you know, founders that are young, I'm kind of like, you realize your career is barely started. Like you got many more of these to go and the truth is they don't. And why would you, because it's the only one you've had so far. I certainly didn't understand it. I thought, I genuinely thought that if I didn't figure everything out by the time I was 30 that, like the entire world just implodes and now I can't even remember that age. It's amazing.

Ryan Rutan: Yeah, I was looking back on that. What I didn't know at 30 fills a lot of books. Right. What I did know, it's a really short story,

Wil Schroter: you know, something that's really funny about everything we talk about here is that none of it is new. Everything you're dealing with right now has been done 1000 times before you, which means the answer already exists. You may just not know it, but that's ok. That's kind of what we're here to do. We talk about this stuff on the show, but we actually solve these problems all day long at groups dot startups dot com. So if any of this sounds familiar, stop guessing about what to do, let us just give you the answers to the test and be done with it. And I get the same thing now. And I think I mentioned this in one of our other podcasts. A friend of mine, a guy named Jeff Wilkins that we talked about. Started comp most people don't even remember it if you're old enough to remember. This is like before the internet. The last time I saw Jeff was a couple of years ago. We're at uh lunch talking about something and he's 75 years old. He looks phenomenal. And at the time I think he said, hey, you know, well, how old are you now? I said I was 46 he was like, oh my God, I remember what it was like to be 46. I was so young and full of energy. I was like, I'm not young and full of energy. What are you talking about?

Ryan Rutan: It's so relative, isn't it

Wil Schroter: the word? Right? So relative. Like I, I genuinely, even now as we're doing this damn podcast about this topic, I still kind of realize that I still don't fully grasp how much time I have. Again. Knock on wood, but how much time I have, but how many more of these games there are to play like these, you know, long 7, 10 year windows. Now, let's distill it just a touch and let's say you just came off of a 3 to 4 year run and in your mind, that's your entire lifetime. Given the scope of what we're talking about. It almost seems absurd to consider that an entire lifetime. Now, you most likely lived an entire life within that. I've got three or four year windows that definitely felt like an entire lifetime. But that's sort of the point because then you zoom out and say, cool, if you realize how much you did, how much you experienced, what you just went through in 3 to 4 years and now you've got 30 to 40 left. Do you realize how many shots on goal you still got? It's

Ryan Rutan: a ton

Wil Schroter: and chances are, this is the worst one.

Ryan Rutan: Sometimes that feels exhausting. Right? Just the idea that like, wow, we're gonna keep doing this for that long. Holy hell. Yeah. And most of the time, like, I'm super pumped about that. Right. I look at it there, there's days where you're tired and you're like, I get to keep doing this until I'm 80 90 100 I hope kind of like on the tire days it doesn't feel so good. But on the days where you're like, ok, I didn't get everything I wanted to done today and then you gotta remind yourself, well, there's like 40,000 more of these, we'll be ok, we'll

Wil Schroter: manage. Yeah. Yeah. Right. I think when we, we're further along in our careers. We start to understand that, that these periods of time have a lot of value. You only get so many of them, but they're pretty big swings and I'll give you an example something that, that a lot of people don't even think about. If I mentioned to most people today, Elon Musk, I'm gonna say, what did he do in his lifetime? And everyone's gonna say he started Tesla. We all know he didn't actually start Tesla. The funny thing is it's been so long ago. People don't even remember that he was an investor in Tesla. He didn't start Tesla, right? He did sue somebody to make them force him to give him his co-founder title. But you wasn't a co-founder. But so what did he do before? That? Most people don't remember or they don't know or they don't care. It's so relevant to his career. But the by the way, footnote there is he started paypal with Peter Thiel, right? I mean, they merged two companies to bring them together and he made like $100 million off of that deal. I mean, long time ago, it's like 2001 era where they sold to ebay and then if I were to go further and say, but you know, he was way successful before that, right? And he like, wait, what? He did something even before. Yeah. And remember my memory is always, I think it's like zip two net or something, there was something he started with his brother in the nineties that was like, maybe like a, not a classified ad business or something that he sold for like 40 or $50 million. In other words, that was by far the most important thing that had ever happened to him, let's say, by his twenties. Right. And that was going to pale in comparison to what he did going forward. Now, if you look at that in the context of success, you're like, well, yeah, if I just have bigger and bigger successes, yay me. But that's usually not how people analyze this. They're usually analyzing this during failure. And they're saying, oh, you know, I feel that this one thing, I guess this is the trajectory of my career. It's like, dude, not even a little bit, right? Like the next lifetime can go for better or for worse, dramatically different. They're all a little bit of a reset.

Ryan Rutan: Yeah, for sure. And I think that's important to remember too, right? So if it went well, there's still a reset and you have to account for that, right? And that doesn't mean that it's gonna be super simple the next time. If it went very poorly the first time or the second time and you reset, it doesn't mean it's gonna go poorly again, like you get to restart and again, sometimes they go, well, sometimes they don't, you know, remember Michael Jordan, remember when he played baseball. Right. The highlight of his career. Right. Yeah, he did it, he did it. He wasn't bad, you know. But, like, uh, he was way better at bouncing a basketball. He also played golf. Right. Pretty good at that too. But certainly not the high point of his athletic career. Stick

Wil Schroter: with that though. When we talk about all these different lifetimes, one of the things that we often don't hear or we're not told is that you get lots of chances in life to go do something completely different, completely different, completely different. You can go off and you can become, I, I've got a friend who worked at I B M up until he was about 32 years old. He was a business consultant and decided at that point that he actually wanted to become a doctor now he's a GP. Right. Completely changed life altogether. Mostly what I hear are people who went to law school became attorneys, hated becoming attorneys and did literally anything, anything else with entrepreneurship? Like, dude, I've been in pharmaceuticals, I've been in casting for television. I've been in software, I've been in automotive, I've been in so many industries like fuck, dude.

Ryan Rutan: I, I incorporated a cattle ranch at one point, right? We've been all over the map. We've been everywhere, right? And I get all different lifetimes. They feel like

Wil Schroter: that's what I'm saying. So all of these are a different opportunity to reset, re point. Like every time I thought, oh, like I've started a web design company. I guess I'm gonna be web design guy for life, dude. I don't even remember building a web page. You know what I mean? So long ago that whole life, I mean, I still do it in the context of what we do at startups dot com. But that entire period of my life seems so distant and it was a massive period of my life. I barely remember it by comparison. And then I and my daughter and I, from time to time we'll be talking about stuff and I'll give her a story about something that happened and she'll be like, dad, how many jobs have you had? I'm like, well, it's always been kind of the same job, but it's always pointed in a different direction. And it's cool though. Right? Because you learn so much and I guess, you know, if, if I've learned anything through this journey, I mean, you're 30 now of doing the founder thing. It's that you've got so many resets. You got a tonn of resets.

Ryan Rutan: Well, you're in charge of picking those points, right? You can reset when you want to.

Wil Schroter: Yeah. And so most people don't take advantage of that though. Most people don't, don't stop and think, oh, you know, just because this one's over, it doesn't define the rest of my career. I get to kind of just hit reset and move on. Most people don't hear that, which is always the challenge.

Ryan Rutan: Yeah, I think the, the concept of the reset here, the respawn if you will is, is super important because unlike a lot of other careers where if you leave your current job or you get fired, most people will pick up something very similar or exact the same. Right. If you leave a CMO role, you're probably trying for another CMO role. Yeah, we all have the odd friend who, you know, left the, the corporate gig and would become a doctor or become a, you know, an organic farmer or whatever. But the vast majority of people are gonna follow that same path and in founder space, that's absolutely not true. And I think that's one of the things that keeps people trapped beyond the point of no return in their startups is they're like, well, if I, if I'm not doing this, what could I possibly go do? Right. If I don't make this work, I'm useless. If this doesn't work, this is the only thing I know how to do. Right. Well, if you look around you actually don't know how to do that either. That's why it's failing. But like, yeah, you can do anything else. But I think this is really important when people are considering when to call it quits or where that next book end is on the startup life cycle is that the next one doesn't have to be a continuation of that one Right. This isn't a set of sagas that have to hang together. It can be a completely different novel at that point. Right. You get to do something entirely different, which like if you just come off of a failure, that's extremely invigorating. Right. Knowing that you don't have to walk right back in to do the same thing because it's a huge challenge. I walked a friend through this a few weeks ago. He was like, man, I haven't had to apply for a job in, in years. He's been doing the same thing for the same company for like 12 years and he's got to go find a job now and he's like, you could just tell it was killing him to think about having to go and do the same kind of work he just walked away from or just well got let go and now he's got to go do it again, right? And that it's totally disheartening. He's like, he doesn't have the energy for, it doesn't have the passion for it, but it's what he knows how to do. So he thinks that's what he has to go. And, and do, we talked about like how he could potentially recreate himself. And I think his founders were really fortunate because that's kind of built into what we do. Right.

Wil Schroter: I agree. And I think the opportunity there when you're saying, like, this kind of reset, respawn, the opportunity is just to say yes, when my daughter was asking me, how did you get involved in all these different things? I said, you know what I just said, yes to everything and sometimes yes, gets you in trouble and sometimes yes, creates risk and sometimes, yes, you know, creates a whole bunch of things, but generally speaking, yes, is what creates life experience as a whole. And if, what we're talking about is we're so fortunate as entrepreneurs to be able to reset, to be able to respond and say yes again. Well, damn, that's exactly what we should be doing. And we should take advantage of every single one of these lifetimes to get a whole new shot, a whole new opportunity and build a whole new life around it. So, in addition to all the stuff related to founder groups, you've also got full access to everything on startups dot com. That includes all of our education tracks, which will be funding customer acquisition, even how to manage your monthly finances. They're so much stuff in there. All of our software including BIZ plan for putting together detailed business plans and financials launch rock for attracting early customers and of course, fund for attracting investment capital. When you log into the startups dot com site, you'll find all of these resources available.

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