Startup Therapy Podcast

Episode #178

Ryan Rutan: Welcome back to another episode of the Startup therapy podcast. This is Ryan Rotan from startups dot com, joined by my friend, the founder and CEO of startups dot com. Will Schroeder, will you and I have been doing this for a while and I don't mean just the podcast. I mean, the last 20 something years we've spent building and uh growing companies and it's often at this frenetic pace. And why? Because in the startup space, there's this, you know, we're, we're enamored by the idea of urgency and pace and, you know, speed to market and all of these other things. But how long did it take you to realize that maybe we don't always have to go so fast and that we're not really running out of time at quite the rate that we think we are.

Wil Schroter: Took me too long. It took me way too long. Like, I mean, this like so many other things that we talk about Ryan, I wish someone could have come back at such an early age. And I'm hoping folks that are listening, you know, early enough in their careers or this will, this will apply their way and could have said, dude, you've got a minute. You, in fact, you've got a lot of minutes. The reason this came to me later on was because nothing, no self discovery I did. I was sitting across from the founder of Compus Serve. Jeff Wilkins. Right. And you know, for a lot of people don't know what Compus Serve was before there was internet. The way we know it, there was dial up Compus Serve, which became AOL as well, the different companies that actually merged together. And so, uh, Jeff Wilkins, the founder, who's been a friend for a long time, Jeff at the time that he and I were sitting down for lunch. He was 75. That looks amazing, by the way. Right. He looks like a stock photo of how you wanna look when you get older.

Ryan Rutan: The Silver Fox.

Wil Schroter: Yeah. Exactly. Right. He, he and I are talking and he's talking about the arc of his career and basically how long he's been at this and all the exponential things he's done in his career and he's 75 years old at the time. And I think I was about 45 years old at the time. It occurred to me as he's saying this thing that he's done more in his career in the last 30 years than I did in the 1st 30 years. Right. I mean, just the, the exponential and it occurred to me that we have so much time in our careers and I've been the same as you, I've been running as hard as I can. Every year has to be the seminal year. It's gotta be done this fast. And I realized, and I started thinking about it, the men and women who have built the greatest things in history didn't do them fast. They actually took their time and built these amazing, amazing companies. So what I was hoping we could dig into today is how much time do we actually have in our real careers for people earlier in their careers? This should be a watershed moment where you said, oh damn, I need to be thinking mommy, I cure very differently on the flip side for folks that are later in their careers, starting to realize that it doesn't take forever to do seminal things. But you do need to have a long view. And again, I think this is once again the antithesis of how people think about startups. And yet I think it's actually the most valuable way that people should be thinking about startups, right?

Ryan Rutan: And everybody just wants to hear us talk about the secret formula for the overnight success of a startup company, which it happens. It does the overnight successes happen all the time 10 years after they start uh they, they become overnight successes. Yeah. You know, and it's funny that, you know, this has become such a, a baked in part of the startup narrative, the oldest trope. Yeah. And, and I think that unfortunately, uh, specifically for people who are just getting started in this will buy into that and then set the pattern that will then continue throughout their career. Hopefully until they hear this and go, oh, there's a different way of thinking about this because you and I both know plenty of founders ourselves included who have been guilty of this over a long period of time and sort of figured it out the wrong way, which isn't, you know, objectively looking at early on and saying I have plenty of time. Let's think about what do I want to accomplish? And let's think about what are reasonable time frames for doing that because as often as we've seen founders who have taken the, you know, the fast path and, you know, they're, they're killing themselves, they're trying to do everything they can, it eventually ends up taking them 7 to 10 years to be successful anyways. And so we have to wonder, had they just started at that pace and planned to build over a period of a decade, right? Instead of saying like, you know, this has to happen this year, this has to happen this year. And again, we're always, we're always tempering this advice. Like we're not saying, don't be urgent about things, don't try to make things happen fast but be reasonable about what actually happens within given time frames. Well, you know, you were, you were talking about, you know, like what happened in, in the course of a decade. Right. And depending on which decade we pick, there's a hell of a lot of density built into almost everybody's decades. Right. Right. And yet when we think about, like, oh, I've only got 30 years left in my career, 40 years left in my career. That's three or four

Wil Schroter: decades in lifetimes is what it is. Right.

Ryan Rutan: Ton of things you can do in that amount

Wil Schroter: of time. Here's the challenge though. I think when we baseline, how far we are into our careers, we blur that with how far we are into our lives. So for example, this is the most overused trope, let's say of a 25 year old, 25 year old. How far are you into your career? I'm 25% of the way. Really? Did you start your career at zero? No, you started your career like two years ago, right? You are two years into what will likely be given the future uh in longevity, 50 to 70 years of your professional career, you are a year two of 50. Why are you shocked that you haven't figured everything out by now or said differently, said differently. This has been so life changing for me. What can you do in 50 years on this planet? You could literally do anything in 50 years. So why are you so concerned about what gets done in the next 6 to 12 months and not that urgency doesn't have its place. It does. And that's fueled so many great things. But I think urgency has taken the place of having a long view and the long view is the point of why you're doing any of this to begin with. What's the mark that you wanna make over 50 years? What is the epitaph you wanna create in your career? That said this person had their eye on the prize forever and built toward it nonstop. Those are the people that change the world, in my opinion.

Ryan Rutan: Yeah, for sure. I mean, you can pick a lot of analogs here but, you know, just think about the legacies that we all respect. None of those were overnight successes. None of those were, were one time shots. They were all people who worked hard, had a long view, had ups and downs and that's something we have to remember here is that it's, it's not gonna be just this purely linear progression and it's not gonna be just a pure exponential progression either where it's always some version of up to the right. There's gonna be ups and downs, there's gonna be decades that are better or worse. There's gonna be year periods that are better or worse and that's ok. Right. You know, this is the, the whole theory of the stock market, right? Like as long as you average it out over time, you're gonna get your rate at 10% cool. Right. Take the long view, build over time. And yet in the star space, we just have such an aversion to doing that because it feels like such an arms race from the day. We declare that we're gonna do this thing. We want something to show off and be able to tell everybody. Hey, I did it, see, look, I did it full knowing that it's gonna take a hell of a lot longer to do that.

Wil Schroter: We've got two paths that have a kind of a different built-in ticker on them. One is your traditional venture route where once you take on venture money, those venture firms, they have to return all the capital in that fund, which means you have less than a 7 to 10 year window to return all the capital in that fund. Ok. That is where the whole startup ecosystem is built, you know, around uh venture funding, et cetera in those timelines. And that's where that urgency comes from. And that's fine. There's another side of it where we're saying I'm bootstrapping this company. I'm not on that timeline. Now, of course, I want it to be successful the sooner the better, right? Because I wanna get paid, of course. But what about something a little bit bigger? What about saying for what I'm trying to build if I have this vision for it, if I care about it, what can I make this company over the course of 30 40 50 years, the most powerful companies in the world were built over generations over decades. By virtue of that, the most prolific careers in the world were built over many decades with a single compounding focus. That's what I want to see. Folks have. Not just where will the company scale this year that it's important, it's got its its own uh virtue and value. However, what we're talking about is a much different purview of our careers in saying as Ryan Rotan, what can I build over my collective 50 to 60 years of contributing this planet. And when you look at it like that, holy shit, you could literally do anything but people don't think about it like that and that concerns me.

Ryan Rutan: Yeah, I think they get so caught up in the short term and this need to achieve and this need to show progress and we've talked about, I mean, there's, there's a whole lot of emotional issues that get wrapped up in this, right? When, when we want to sit back and, and be purely objective and you and I can do that during the course of a podcast a little bit easier, right? When you're staring at the mounting bills or the the declining bank balances from your venture funds or whatever it is, that's driving that urgency for you gets pretty emotional, right? And you, you want to be able to succeed and achieve and, and do what you set out to do. And sometimes it's externally driven, sometimes it's internally driven. It's almost always misguided. Right. Whether we're allowing the opinions of people around us to tell us that we haven't accomplished enough by now. Right. Because that's the other thing. Right. I hear this all the time and it, it's always from people who are younger than I. And they're like, well, they want to compare like, what, what had you done by the time you were this age? Like you want to know when I walked to, when I said my first words, like, what the hell does that have to do with who you are or where you're going to be? But people do this, they allow external factors, external opinions to start to form where they think they should be at any given point in time. And that has such a negative impact on the founder mentality and then your energy and therefore your output. And again, we talk about this a lot. There are so many self fulfilling prophecies in the startup space. When we start to work that we haven't accomplished enough, guess what starts to happen. We stop accomplishing

Wil Schroter: things. Actually another side of it, right is even when you do, it's never enough because once you put yourself on the treadmill, I haven't done enough. But I'm telling you firsthand, you know, once you get to that point, it's never enough. It's never young enough. It's never, you know, a dollar figure. That's big enough. It actually doesn't matter. It's, it's a broken mechanic that only 1000 entrepreneurs go through every single freaking second. Absolutely. Let's constrain this back a little bit and let's talk about what you could actually accomplish in any one of those decades. Because if we're talking about, we've got an opportunity to have 56, maybe seven decades. If, if we become full cyborg, right? Like productive human. Let's talk about what can get done in just one of those decades. And I'm saying this because for a fair amount of our listeners that would be essentially about under 33 under 32 they haven't even had one yet. They haven't even had a single decade of their professional careers to understand how life changing you can make just one of these building blocks, not to mention, stacking them all. I'll give you an example. I'll give you an example in the past decade. For me, I just turned 48 in the past decade. I got married, which is pretty important, right? Had my two wonderful Children. We built startups dot com. I lived in three different cities. I lived in Santa Monica and San Francisco in Beverly Hills and, and Columbus. If you can count that as well. That's where I started, went on more trips than I've ever gone on in my life. Like, explored more of the planet than I than I have ever ever explored in my life. Battled some crippling diseases had 10 surgeries for them. Not exactly the highlight reel, but a lot you can accomplish. You know, in the course of a decade I bought six companies and all that. We did and kind of all the adventures that, that entails and that's just the start of the list. One decade, one decade. And interestingly, probably not my most active decade. In other words before, when I was like, let's single or I was doing different companies, et cetera, I was running five companies at the same time, I was way more active right now. I I'm in bed by nine PM. That's where the least amount of activity nature

Ryan Rutan: comes into play at some 0.1

Wil Schroter: decade, right? That's how much we can put together in a single decade. I'll give you some other examples that I, I think are, are so illustrative of this product over this point. First one, every single one of the most successful companies in tech history was built in less than a decade. Now it became what it truly is today in the many decades that follow use Apple as an example. Apple is, is 100 of the company. It was in its 1st 10 years for just a bunch of reasons. Just give it enough time. Some companies are not. But if you look at Google Facebook, uh you, you name it, you name the company, it took 10 years or less for them to become the titan that they are, which once again means in the increment of a single decade, you can do anything, which also means, which I think is interesting. This might not be that decade for every one of those founders, it just happened to be their decade, but it might not be yours. It might be two decades from now. I was using this in, in the context of presidents of the United States. Historically, their most important formative decade was when they were in their seventies. I mean, you really think about what that is, right? Where they kind of the top of their game and the most exponential thing you could possibly do, like running the whole world. Everybody has their decade. Now, think of how much you could pack into a decade. And now I'm gonna tell you, you got 56 or seven of them. Yeah,

Ryan Rutan: a ton of time, right? And yet there are still people out there who are gonna be listening to this and going. Yeah. But in my case, right, I need to move faster because of competition or because of, you know, I, I wanna be 30 under 30 or 40 under 40 or whatever the hell it is. That's, that's driving you to be driven by a timeline instead of by a vision, right? And I think that that's, that's an important piece of this is that we have to take, you said at the beginning, we got to take this long view and then we have to think about what does that actually take to compose, right. And, you know, in some cases, I think you could actually make the case that if you try to do these things too fast, you're not gonna end up building that thing, right? Some of these things take time to set, right? They need to settle in and to this point of like different decades and kind of different epochs and eras in our lives. There's something else that's happened. And I think in almost every founder I know and again ups and downs trials and tribulations, it's not always just this linear path, but we tend to build momentum over time such that certain things become easier in other decades, right? Like there are things that I absolutely have access to now in my forties that I did not in my twenties and that's from my personal capital, my network, my net worth, all of these things have changed significantly over time and allow me to do things differently and allow me to look at things differently, right? And so it's not to say, look, just, you know, goof around until you're in your forties because it's gonna be easier now than it was then. It's not the point. But I think that there are some things that change as time goes on that while yes, we may have less total time to accomplish what we're doing in terms of our total career, right. You know, if you said 50 60 years that we have to do this, if you've already spent 30 or even 40 of them, don't assume that the pace in those final 20 is going to be the same. And to your point. Well, like you're now in your forties approaching the fifties, sadly. Yes. Yeah. And so you just pointed out that you actually spent the last decade, maybe being a little less active and yet being very productive, right? One of the best decades you've had. And so like the pace may change, this is to say, like we're just gonna keep moving faster and faster. And that somehow magically in my seventies, I'm gonna to be some sort of a hyperspeed juggernaut. That's not what I'm saying, but I'm gonna have a lot more resources, a lot more assets at play than I had in my teens, in my twenties, in my thirties. And I think we have to account for that too. We have to plan for the fact that there, there will be certain things that become easier over time.

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. You snuck a word in there called pace and I don't want to overlook this one. I think something we've talked about endlessly on this show is that we've got to maintain pace and we're talking about, you know, physical health, mental health, et cetera. And I think part of where this kind of cautionary tale comes in is that if you really want to build something truly long term world changing, you're gonna need to pace yourself. And again, we've had whole shows about this where, you know, we, we have all these issues where we didn't pace ourselves. And it's like if we really want to win that Iron Man Triathlon, if we really want to win something so incredible and so powerful, we can't just go full sprint right out of the gates. We have to be around long enough. We have to pace ourselves to achieve this amazing thing. At the end, we have to pace ourselves and pace is something that if I'm being honest, I don't think I've figured it out or even started to unpack at all. So maybe a few years ago, I mean, I just like, and now it's starting to come to me. I agree with that. If I'm really gonna do the things that, that are gonna be on my career epitaph. I've got to have enough energy and pace to actually get them all done. The worst thing I can do is burn out. So that, let's say that by the time I'm 60 or, you know, kind of some further date from now, which isn't that far away at some further date. I'm so exhausted that I can't go on. I need to be Jeff Wilkins from Copy Surf who looks like he hasn't aged today in 30 years and do whatever he's doing, right. Like I wanna be able to say what matters to me is helping founders at a career level. All that I care about is helping founders and I wanna be able to be around to do that effectively for as long as I possibly can until my last day, if possible in a way that, that I can sustain and that I care about. But I don't wanna be in a situation and I've been on this path where I'm just running myself into the ground. And the idea is that somehow magically that's gonna go away or take care of itself. It does not,

Ryan Rutan: it does not that that was the beginning of the decade you just described, right? If you're, you know, working towards the Jeff Wilkins plan, you're doing a good job. You're, you're on your way now because we were certainly looking way older, you know, 78 years ago than we look now, right? At least when I look back and some of the photos, some of the stories, right when Amazon and Google Photos and Facebook like to pop things up and remind me just what a shitty job I was doing of taking care of myself. You as well. I'll throw Elliott into the mix here, I'll drag him into this. We were doing a great job of burning the candle at both ends and in the middle at the same time. Like if that was, if that was the goal, then we nailed it. Ryan.

Wil Schroter: You look younger now than you did 10 years ago and you have COVID today.

Ryan Rutan: Oh yeah, that's, that's a, that is, that's not, that's not a good sign. It's not a good sign. Yeah, I am. I have now officially have begun participating in the pandemic for real.

Wil Schroter: You took your time. Yeah. Well,

Ryan Rutan: look, it took, I know. Well, hey, look, it's super mild. So, uh you know, for anybody who's out there really suffering, I'm sorry. But uh I'm, I'm getting off

Wil Schroter: easy. The point is we're going back to pace, but I think it's easier to understand pace if you have some perspective of what you're pacing for again, this goes back to the Iron Man idea. If I don't realize how long this thing is actually going to take and how much I need to pace myself. Of course, I'm gonna go sprinting right from the very beginning, right, jumping into the river if you will and not realizing, not realizing that the only way to actually do this well is with paste, but you can only really appreciate pace if you understand how long the race actually is. Which is interesting to me because for the longest time and hell, if I'm being honest, up until about three or four years ago, I didn't understand how long this thing actually was now that I'm realizing it, how silly I felt about how it was pacing, you know. Yeah,

Ryan Rutan: we, we weren't pacing, we weren't pacing at all. I mean, like the only version of pace we had was like, how far does the accelerator get pushed down? That was it, what, what's the limit on acceleration? And you know, if we, if we draw an analog here and we were to say like, OK, yeah, you're gonna start a race. We're not gonna tell you how long it's gonna take. We're also not going to tell you where the finish line is. Would you start off by just sprinting in a random direction? Because that's literally what we're doing with most of our startups and that, and that's, it's hysterical like, and you lean back and look at it that way, you know. Yeah, I guess that doesn't sound like the brightest move and yet that's what we do, right? We have very little definite about what the final form of the thing is gonna be how long it's gonna take us to get there and what we want to do with it at the end, right? Like what that legacy that we end up leaving looks like compared to what that first diagram sketch cocktail napkin with, you know, run yank all over it and the final product tend to be so different, right? So the idea that somehow we take that cocktail napkin map and we just start sprinting and we're gonna maintain that until we figure it all out. Sounds kind of idiotic.

Wil Schroter: I, if I were to take that a step further and I were to say, what is your pyramid? What is your building a pram? I'm talking the Egyptian pyramids, right? As a metaphor for what you really want to build out of your entire career. You know, let's say I'm, I'm interviewing somebody who's 27 years old and they say, you know, what do you want to do with your career? They'll typically talk about how they would want to go from point A to point B here. I want to become vice president or whatever and maybe move on to the next company. But if we're to zoom out and this is so important for founders and we say, what is your pyramid? What are you building your entire career on? So that when you retire, you can say I did this and the I did this could be it. I'm sure there's, there's a wealth component that obviously people will think about that. There's a change in impact on the world component. There's a personal developed component. But if you ask most people that you're interviewing, but I'll take this step further and I'll put it on most founders. And so you're working really hard now at this one thing. But what's your pyramid? What is that, that long term life goal that all of this is working toward for the longest time, I didn't have one. It didn't even occur to me, hence this podcast. And so to your point, I was just running in directions because I knew I was poor. So I need, just need to fix that problem. But up until the last few years, I never had this career pyramid where I could say, you know, what, every single thing that I'm doing is actually working toward this singular collective goal. And, and, and if I were to illustrate that now, it's all I care about is making the world a better place for founders. I want to build a system, you know, not just with startups dot com, but in my career in my life where I help more people become founders and not because that's any better than any other career is because the one thing I understand, I feel really passionate about, it's what we know how to help people do. Yeah, tomorrow, as I mentioned to you, I'm gonna go to my kids' school and I'm gonna start teaching middle schoolers, entrepreneurship. It's part of my pyramid. Right. I don't look at it as just this one off thing that I do. I look at it as this is my legacy. My legacy is gonna be planting seeds tomorrow with all these kids and some of them will go on and use that seed and grow on to become entrepreneurs. And if they do that's my pyramid. that's what I'm here to do. You know what I mean?

Ryan Rutan: Yeah, for sure. I think that like you hit on something else important there, which is that this thing is multifaceted, right? There are certainly personal financial goals. There are, there are personal learning and growth goals. There are goals for the family and then and kind of the legacy you want to leave. There, there are things that you want to do professionally and there's that sort of like overall dent you wanna leave in the universe, which in in our case is, is making this a better place to be a founder.

Wil Schroter: I get it. But when we're talking about building these pyramids, here's what's so interesting and this is really what this is all about. The fact is if we want to build this big amazing pyramid, this thing that will stand the test of time, that is our career and our legacy. If we try to just build the whole thing at once, it won't happen, we actually can't move that much earth, if you will, right? Conversely, if we just take, if we say, look, I want to build one stone at a time and I'm gonna keep pacing myself with those additional stones, those big giant cubes, you know that make up the pyramid, we cannot be stopped. That's the whole point to this as a person that paces themselves with I and the prize over a long enough period of time, we cannot be stopped. And that's why we should be focusing on this one singular goal of where we're taking everything. 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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