Startup Therapy Podcast

Episode #273


Ryan Rutan: Welcome back to their episode of the Startup Therapy podcast. This is Ryan Routan from Startups.com, joined as always by my friend, the founder and sometimes co-carpenter Will Schroeder. Will, pretty much every founder we talked to that early stage, they've got that that starry-eyed look, and they've got a, they've got this big North star, this very clear why, and then there's usually a couple of them, right? The why they want to build this, why they wanna they wanna go and start to this thing and it's, it comes in a lot of forms and we can talk about all those, but at some point. When we get caught up in all of the what and the how and the when and the with who. We lose sight of that why? And, and it can cause lots of trouble, right? But both for the, the existence of the business, uh, particularly for the it's an existential crisis for the founders. How do we make sure this doesn't happen, and how can we dig in and understand a little bit more about why it happens, when it happens, where it happens, and what we can do to create a little bit of a renaissance around our why and bring that back into the life of the business.

Wil Schroter: I think. A lot of founders are in that problem right now, a lot of founders, you know, a lot of us are, are deep into our startups right now, and startups go through an epic, almost like a generation of startups. And, and I think, you know, at this moment in time we're we're kind of the tail end of 2024 as we record this. I think we have a whole generations of startups that are like kind of pretty deep in their startups. I've got lots of friends right now that are that are 89, 10 years into their startups and They they've lost their why, their why, and this is for folks just starting toward the end. The why is, why did I start this thing? And what did it look like when I first had that idea, right, when you think about the first at the inception point, when you first had an idea, what defines those early moments when you had an idea or when you see a founder have an idea? What what are some of the things that define what becomes the why you started something?

Ryan Rutan: The why, yeah, so it's interesting and I think there in I'm trying to think if it's always the same sequence of events or or if it can change a little bit, but sort of there there's always a very similar cast of characters that show up at this party in my head. Um, the one is around like The people I want to do it for, right? For me, it almost always starts with the who, right? So it's just like I see, I see a particular population of people that that I want to help, and then it's like, OK, so like why do I want to help them because their their lives are more difficult than they need to be, or they're suffering from something that's unjust or whatever it is, right? Or there's just this really cool opportunity to help them do something that they do way better. Sure, awesome. So that's the, that's the who. And then, and then a little bit about like the the what does that mean? Like, what does that start to look like? How will I be spending my days, right? Then your your mind kind of goes off and and and all these tangents, um, that eventually get pulled back into to some form of an idea. Uh, but for me, it always starts with the who and then kind of like the where do I want to take them? Like what's that transformation look like? And that really comes down to like, what's this dent we want to make in the universe, right? So collectively, the this thing, you know, in your mind jumps to a lot of places like who else do I want to involve in this? Who do I want to do this with? And where are we gonna do this? How are we gonna do this? Is this gonna be, you know, a software thing? It's gonna be a people thing? What, what are we building? Is it product? Is it service? And so you go through all of this, this exploration around some of the what, but like at the very, very core of it, it goes back to like, but why this? Why this as opposed to anything else I could do, right? And and that's often sometimes it just dies right there. It's like, you know what, actually. No, I don't. There isn't enough of a why here, right? And so, you know, you might see the opportunity there might be financial upside in it or whatever, but if the why isn't there, cause I think you and I have done this enough that we know that at some point, you get to the middle of this journey and you don't have your why. And the universe is punching you in the face with every possible downside that comes with the startup, and you're like, I don't remember why I'm doing this. It gets really easy to pull the, like, fuck this ripcord and just bail out, right? So for me it the why is like, it is the driving force the early stage because it's all that exists,

Wil Schroter: right? And you're fired up about it, right? It's something that you want to bring into the world, right?

Ryan Rutan: To the point of annoyance to everyone who's a 1 or 2nd degree connection. Yeah.

Wil Schroter: Yeah, yeah, and no one else gets it, right? And it's, it's, it's something where you also want to build something for yourself, for yourself, for your family, you know, who, you know, whoever's presents to you, right? Uh you part of that

Ryan Rutan: imagination, right? You see the Super Bowl version of it too, right, which is it's gonna be this, it's gonna be that. It's gonna be amazing, right? version of that,

Wil Schroter: but in the early days, like in the formative days, you get this vision in your head and you can't let it go. That's, that's what's so exciting. It's so awesome about what we do, right? When you talk to founders. in year one, they are beaming with that exuberance of their why they almost shut up about it, right? That's so awesome.

Ryan Rutan: But then it almost feels like a malady of sorts, right? Like, you know, we talk about that, we talk about like, you know, catching the startup bug or the entrepreneurial bug, and it really does feel like that because it, it starts to feel like this compulsion from inside. It's like I can't think or talk about anything other than this because I'm so attached to seeing this thing happen.

Wil Schroter: But then you fast forward to like year 89, 10. You say what happened again?

Ryan Rutan: Like yeah, like what happened? What happened to that

Wil Schroter: guy right? Like, what happened to that guy why? Like in, in that person, that founder is so far removed from that exuberance, like, like all of that was drained from them, that that life force of optimism has been drained in so many different ways and you're like, what happened? And so, in this discussion, what I want us to talk about is how that happened, but more importantly, more importantly, how to get it back.

Ryan Rutan: Yeah, I think that's, I think that's critical. I think that's critical because I, I'm trying to think of a founder that I know who kind of like from inception to wherever it ended up, whether it was success or failure, they didn't lose their why at some point along the journey. I'm not comfortable saying I have an example, right? I don't, I really don't think I know anybody who's just like, I knew why from the day I started this, yep, I and all the way through, and now here it is, you know, 20 years later, 10 years later, whatever it is. They didn't lose at least some of that why along the way.

Wil Schroter: And, and, and you see this in different facets of life. You see this with couples, right? You know, they're they're that, you know, those young lovers that they're the honeymooners, they are then the years later they're just this old, you know, married couple that are, you know, uh, just, yeah, right? And, and, and you look at that and you like, what happened? How did that happen, you know, where did they lose their why? Now for founders, it follows a fairly specific and repeatable path. Yeah. But it's a dangerous path, and I think part of that danger is not understanding how it happened, and it and again it happens in a fairly repeatable way and and let's start there. Let's diagnose.

Ryan Rutan: I wanna add I wanna add one thing to that. I wanna add one thing to that, uh, which is that we don't necessarily see or know that it's happening. I also think the invisible. I also think. The invisible hand, but I, but I think beyond that, I think we also don't value the why enough. Like it, it starts off and it is the only thing, right? It's the only thing at the beginning it's like my why, this is my reason for being, this is the reason I'm gonna go do this thing. And then at some point it starts to take 3rd, 4th position over some other necessary stuff that are that's involved with running the business, or being run by the business in some cases. So I just, I don't want to lose sight of the fact that I think part of the challenge here is that we don't treat this with enough value as founders ourselves, that we're like, yeah, the why is super important. It's Motivated me to get started, but now I'm into the details. I'm into all the the stuff that has to happen. And so it's easy to just let that take, you know, a backseat position,

Wil Schroter: right? No, I agree, I agree. And, and the why is our superpower. That's why losing it, that's a big problem.

Ryan Rutan: So funny,

Wil Schroter: right?

Ryan Rutan: It's what's so funny about the fact that we devalued at some point, like, it's the whole reason we're here.

Wil Schroter: When I think about companies that lost their why, I think about Apple. Apple feels so soulless at this point. I think about Google, even Google complains about losing their Y. uh Eric Schmidt, you know, the former CEO, uh, not a founder, but a former CEO, has been all over social media lately with all kinds of things he's probably not supposed to be saying, talking about how Google has lost its why, right, it's motivation. Yeah, he said something. In fact, it wasn't exactly these words, so I'm paraphrasing, like they could fire half their staff and it wouldn't make a difference, right, which, like, probably not wrong, but like

Ryan Rutan: that's that's a high degree of apathy that's what that indicates. So

Wil Schroter: that's kind of what he's saying, right? It's almost a backhanded compliment. He's almost saying the company is so successful that even with half of its staff, it would still be printing money, more money at that point. But what he's saying is like. They've lost like what used to make Google Google, right? Apple is a shell of the company it used to be. I'm not knocking Apple. I mean, it's like as a company that's run, Tim Cook is a phenomenal operator, right? But it's not great,

Ryan Rutan: it's sound, but it's not, yeah, it's not, it's no longer like the visionary company that it was that brought us things that we can't imagine not having now, right? When he

Wil Schroter: died. The why died with it,

Ryan Rutan: right?

Wil Schroter: Yep, um, sadly, um, but, but my, my point is, a company has that DNA that has the why. As founders, it's our job to maintain that and more importantly, bring it back, not just for the company's sake, for our own sake too. Let's talk about where it gets lost, cause we'll talk about what gets lost along the way and why it's so important to bring it back. So let's talk about uh phase one. Where it starts to go wrong, OK? We're all fired up. We're we're all super excited about a new idea, but now we have to turn new idea into an actual company. OK, so it's all great at the idea stage. We're on the whiteboard, we're at the kitchen table, so to speak, and now we gotta make it company. Now

Ryan Rutan: we gotta hire fun and games while we're thinking. The minute it turns into work, it's a slightly different story. Now

Wil Schroter: we gotta make it a thing. Now we got to involve other humans. We gotta hire people. We gotta raise some money if that's the case, right? Uh, we gotta build product. Now we gotta create processes, we have to create company. That's boring, right? It it it might be exciting in its own way, but, but what I'm saying is

Ryan Rutan: the only why involved there is because you kind of have to, there's no way around it, right? Right.

Wil Schroter: again, while some of it's exciting, I mean, you and I, you know, love to build a good process and and whatever, the problem, like anything else in life, once you make it real, it starts to become real boring. Yeah,

Ryan Rutan: and hang on, cause, cause I do love to build the process, but I love to build the process with the why behind it, right? So again, like even. That, like, it's one of the things I think that's where, like, it's such a magical force. The why is such a magical force that can make you do things that otherwise, like, I wouldn't just sit down and decide to create a process, right? I don't want to create a process, but I know that the process is involved in creating the outcome, the dent that I'm trying to create. And so, therefore I do, right? So I think this is, it's, it's so important that we don't lose sight of this the whole way.

Wil Schroter: Let me give you an example of the first time I saw the why get deteriorated in action. OK. We were, uh, built my first company and we're starting to staff up. And at the time, just from like a, a fun, cool environment standpoint, we're hiring everybody, everybody's young and everybody's just like just firing away, right? Very irresponsible, very immature, right? And, and, and I'm sure there were all kinds of problems with that. We hired our first adult in the. The requirement to be an adult at that time was 30.

Ryan Rutan: I was gonna say it was actually just being an actual adult like like if you're 18 plus, you're the adult in the room.

Wil Schroter: You're old enough to rent a car, right? And I remember them coming in and putting in rules, not like crazy corporate rules, like rules of being an adult. And I remember thinking. You just made it less fun.

Ryan Rutan: Yeah, it's, it's now less fun, right? It might have been necessary, but

Wil Schroter: probably, probably, to be fair, it probably was. I, I won't take anything away from them from doing it, but I distinctly remember. You took away some

Ryan Rutan: why. It's one of those first things because I think we talked about this a couple weeks ago when we were when we were going through the episode on losing control and the places that we, that's exactly what I was thinking, right? So I, I think that there's there's a corollary here, but in this case, this is one of those first places where we run into a constraint, correct, right? And, and it, it has a real impact, right? And and it does, it starts one, it impacts your energy as a founder you're like, oh. When I was just thinking about all this, I could kind of think whatever I wanted. Now that we're doing, there are some real limitations here. Some of those are humans, some of those are just, you know, physics. There's lots of things they get involved that create these caps for us, but I think that it's one of those moments where it's, it starts to obscure the why a little bit, right? We start to let what or how get in front of the why, right? And we start to say, well, The why is important, but because of how we have to do this, we're gonna deviate a little, and and it's not necessarily like that the why goes away in that moment. I think that's probably the the the core part of the discussion today. It's death by 1000 cuts, right? It's just like, it's one tiny little cone of pain after the other until you can no longer see the damn thing at all.

Wil Schroter: It was a dumb thing too. I remember at the time it was like on a Friday afternoon, some of the guys like to like pop. Open a beer and have a beer at like 3 o'clock in the afternoon in the office, which at the time was unheard of in corporate America, right? Let me say in in in our version of corporate America, maybe the rest of corporate America, people were doing it everywhere, but in our version from the jobs we had come from, it was unheard of.

Ryan Rutan: So doing

Wil Schroter: it felt like we were like getting one over on the man, right? And

Ryan Rutan: it or becoming European. I mean, it was one of the two things.

Wil Schroter: We would, yeah, we would later learn that yeah all of Europe and figured it out. Anyway, but then we had it like taken away from us, right? And again, I know this sounds so minor, but that's actually why I'm bringing it up. Um, and I remember it felt like, huh, that, well, that feels like less than what we wanted and to be fair, at the time I was like, yeah, it probably does make sense, etc. and I let it go, and maybe that was the right move, but it would become one of many, many of these 1000 paper cuts.

Ryan Rutan: That's the

Wil Schroter: thing. Fast forward years later. And there were a million of these restrictions, and and and it wasn't just like, you know, like policy and culture things, it was, it was a million things. Yeah, I remember sitting back like, what the hell happened here? Like, we used to have a fun office, we used to have fun clients, we used to have fun work, we used to have a fun product. It's all gone. I got to be

Ryan Rutan: taken

Wil Schroter: for

Ryan Rutan: granted either, right? Like a good part of the why for most people is I do it the way I want to. I, I, I have to do it that's the way I, I've decided, right? So it's, it's, you know, me do it my way, right? And so when that starts to go away, that's a big. Piece of the why. I mean, I think in most founders we were to break it down and like mathematically wanting to do it your way and being able to do it the way you want to do things is probably about a third of the why in the beginning.

Wil Schroter: Right, like, at some point I looked around and even though the company had become very successful. I looked around and I said, who are the people that I'm working with? What is this product that I'm working with? Who are these clients that I'm working with? What is this industry that I'm working in? Like, where the hell did this office come from? What is this chair I'm sitting in, like, what the hell happened?

Ryan Rutan: Right here, right? Yeah, it's, it's funny at some point you just wake up and you really don't recognize things because it's all, it's, it's, it's a bit of it's the boiled frog syndrome too, right, which is that everything. Kind of changing slowly over time. There are very few of those like big moments where it's all of a sudden like, whoa, or why it was just ripped out of our our hands while we were holding onto it so tightly. It's not that at all. It's kind of like one day you walk in the office, you walk and going like, what is that why? I know I put it here somewhere, right? It's gotta be like, I thought I put it on the corner of my desk. It's not there anymore, where is it? Ah, I'll find it later, right? Right, that's what it feels like to me.

Wil Schroter: It's interesting that you know you said the boil the frog, that that that's really the best way to look at it. And for folks that are just starting out, because I want to address folks at all levels of development in the startup spectrum right now, whether you're in year 1 or year 10. If you're near one, I want you to think about it right now to say, you know, you're fresh into the idea. Those little decisions that you just compromised on 5 minutes ago, they're not little, and you're about to make a whole bunch more in every single one of those matters. That little thing of hey, let's just not, you know, pop open a beer. I'm making a stupid example intentionally because while that's minor, that's how. It starts. 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.startups.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.

Ryan Rutan: It's minor at the time. It's minor time and it's one of those things where I, I always think about, you know, that, that old math problem, right, which is like if you start off on this flight and you're pointed towards whatever and you're off by 0.5 degrees. How far are you off by the time you arrive at the destination, right? And so it's a thing where that, that, you know, you may only, it may be a slight deviation from what you were doing, but over time, that deviation from that path, that 1 or 2%, you end up way wide by the time you're you're you're miles and miles and miles away. And so I think that it's one of those things where it doesn't feel consequential at the time. It's kind of like watching founders spend equity, like it's monopoly money going, well, it's worth nothing now, right, right. Yeah, but, and, and you're the one that that put this so nicely, well, which was that, yes, but it represents 100% of the future value of your company, right? So whatever you're giving up now may seem inconsequential and it is, because the difference between $0 and what you just gave up feels like nothing. Yep, but. If this does become the $100 million dollar company that you hoped it would be, that 10% you just gave a junior developer to build a crap first version of your product is now $10 million.

Wil Schroter: Yeah, exactly, exactly.

Ryan Rutan: So these things tend to magnify over time, they tend to grow.

Wil Schroter: The way to get to major compromise is to start with tiny compromise, right? And watch it compound. And so again, going back to that spectrum, for folks that that are in the early stages. I want you to watch these little tiny compromises, and I want you to make a big deal out of them, right, for just this reason. For folks that are on the far end of the spectrum that are 10 years in, I want you to look back on all of those tiny compromises you made and understand how you got here, right? It didn't come from the big decisions, it came from all the tiny ones, right?

Ryan Rutan: It starts with things like, well, they're not. A great personality fit for what we want to do, but, you know, they've got the skill set. But we need to, we need them right now. It's not an ideal client, but we could use the cash. Yep, it's, you know, it's, it's so many things, but maybe this software solution isn't exactly what we need, but it'll get us by for now.

Wil Schroter: How bad a board member could they possibly be? It goes from this is this is this is where it gets important. It goes from small, seemingly unimportant compromises in the beginning, where we start to chip away from our why we built this damn thing to begin with, to where it becomes, now we're running something for nothing to do with why we built this thing. Let me give you some examples. Now all of a sudden we're out running around town trying to pull together a bridge round so that we can make payroll for a company we don't even care about anymore. Right? We're banging our heads against the wall. I've, I've done this, so I try to be clear, like I'm very familiar with this, right? This is me 2007, 2008, running around trying to raise a second round of capital for for Affordit.com, a company that I didn't even care about at the time. Because I hated the business, I hated the business model, but I cared about my investors. I cared about the people that I that I got into the business with. I don't really clear about that. I just fell into a business model I didn't like anymore and absolutely killed myself trying to keep the business alive for a business that I didn't even like anymore. I had lost my wife. Yeah, right, um, uh, and all of a sudden I'm I'm sitting there going, why am I even doing this anymore, right? In in so many cases we can create a monster that owns us. Right? And many of us have. Many of us are chained to a business that we are running ourselves into the ground trying to service, but that very same business, which by the way, we created, we have to go in service nonstop. Yeah, but over some period of time, we've created this. You're

Ryan Rutan: no longer running the business. You're no longer running the business. You're running from an outcome within the business that you're scared will happen, right? At that point, you're just running away from things you don't want to happen. You're no longer running towards the thing that you wanted to create in the first place and, and. It's a sad state to see founders and unfortunately, like like I was saying, like I feel like most founders get to that point at some point. It's not

Wil Schroter: hard to do. I mean,

Ryan Rutan: it's not it's harder not to. And then at some point they, they do find their way back, but it's,

Wil Schroter: let's talk about that because that's, that's really what we want to sit down and talk about. This isn't about the fact just that we get there. I mean, that's honestly, it's, it's pretty common. Let's talk about how we get back. Yes, talk about how we reverse this course, OK? I think the first part of this diagnosis, if you want to call it that, is first recognizing that it happened at all. I, I feel like by the time we get here, we feel like it's a terminal diagnosis that that that we can't recover from.

Ryan Rutan: I'm thinking about this, like, I'm thinking about how often recently I've I've asked because, you know, look, startups get hard, they get really hard, and so one of my favorite things to ask people to remotivate them is why did you set out to do this in the first place? And they all have an answer for it, but what's funny now that I'm thinking about it, there's a consistent response, which is, oh, right, if there's like this moment where like they lean back and they're just like, oh fuck that, yeah, yeah, the reason why or the other why I started, well, that was so long ago or so far from where we are and what we're doing now, that it almost feels irrelevant. They have to go through that moment of like shit, yeah, we're a long way from that. And then as we work back through it and then we we get there, like it's, it's not the kind of thing that you just forget. You just forget to service it, you forget to live through it, right? It's there, you remember why, but somewhere along the way, you forgot to make that a present part of what you're doing.

Wil Schroter: You bet. I think the first thing that we lose, the first casualty of this. I forgetting that we're entitled to our why. We built this goddamn thing. It's for that purpose,

Ryan Rutan: right? By the way, we built this so that we could have that why, so that it could be the thing that built something for our family, so that it could be the thing that helped the people who want to help, so we could do it our way, right? That's why we did this.

Wil Schroter: We didn't build this as a self-torture machine for the anxiety inducing self-stress machine that it has become, right? At no point were we sitting in our bedroom late at night going, I wonder what I could do to create the most amount of long-term stress that would ruin all of my personal relationships, drain me of all my personal wealth, and get my health back 10 to 20 years. Oh, I know. What product could I launch? Yes, yeah. That was not what we set out to do, and, and yet here we are, right? When I say there's the entitlement there, we somehow feel like we are absolutely entitled to all the bad shit, but somehow we're not entitled to the good shit, right? Oh yeah and and and part of this is that. Reset mechanic, right? To say, hey dude, right, you've already paid your dues on the bad stuff. Time to cash in on the good stuff too, right? And when I talked to founders who, you know, Ryan, you do too, we've already been through the bad stuff. Ryan, you and I have paid our dues 900 times over. So I don't think there's a lot of. Yeah, I was gonna say I don't think there's a lot of convincing that needs to be done there. The convincing is on the good stuff, right? Like it's payback time. And so I think part of that is again a true understanding, kind of the catharsis there to say, you know, that's true. I have paid some dues there. I do need to get back to some why? Because here's what I would say, if not now, when? And if I don't, what was the point?

Ryan Rutan: What's the point? Yeah, you know, it's interesting, man, because the Y fades so slowly over time, right, like we we talked about is that death by 1000 cuts. I think that one of the the challenges is that we forget what a good feeling it is just to have it, right? Just to bring the lie back into focus. Just that, right? Even before you begin to like do things that actually live it out, just by bringing it back into focus has a huge benefit. But I think that one of the challenges that we face, like when we're talking to founders on a on a daily basis, try to bring them back to that why is that because it faded so slowly over time, they don't have a good strong memory of how great that felt, right? Their more recent memories are kind of like, yeah, you know, it was there, you know, it was. Yeah, I remember it. So I think that that's one of the big challenges that like the dopamine hit, the big, like all that euphoria that we talked about at the beginning, that's that surrounds that actually does come back. Yep, but because we've we've let it go over such a long period of time, we don't remember that, and so the incentive or the drive to bring it back feels somehow like it lacks value or like like, well, I could do that. I could. Refocus on my why, but why? Why would I do that when I could just go fix that thing that's broken, fire that person needs to be fired, hire those two people that need to be hired, all of that other practical shit that gets in the way of our why and you couple that with the thing you're talking about, which is that we just don't feel like we deserve that, right? Like that level of satisfaction just because, um, just because this is why we built it in the first place, so don't forget that. And I think that's part of the complication. We just don't have the enough muscle memory around how it felt to want to bring it back. And to me that's super sad, but it's also it's it's a hurdle we can leap and then you and I help people do it all the time. So

Wil Schroter: let's isolate that. Part of it is just bringing it back, literally just bringing it to the forefront, first to ourselves, first to ourselves, right? To be able to to remind ourselves why we did this to begin with. And again, I think there are personal goals there. I think there are company goals there. I think there are product goals there, you know, there are all kinds of those things. But again, bringing it back. Also, with that, some things to remind yourself what you didn't start this with, right? I didn't start this so I could be in political battles with people all damn day, right? I didn't start this so I could ruin my health or start a divorce or, you know, you, you name all the things, right? I, I did not start it for these reasons, right? And these things are happening. And so, you know, I, I need to address these things. Another side of it would be, I need to talk to my team and remind them why we did this.

Ryan Rutan: Yeah, or even be told in the first place, depending on their, on their vintage, right, their tenure, how long they've been there, because again, it, it fades over time, you know, it's it's one of the things I think you've done a particularly great job of as we've hired people. Over time at startups is that we haven't lost that, like that you do introduce that piece, like here's the why we're building this thing. Yep, and I think that's super important because it's, that is one of probably the first casualties as it starts to become obscured from us, the founder, it certainly becomes obscured to everyone else at a much higher rate to the point where they don't know. Like, employee 1000 at Google may have known some of the why. Yeah, employee 45,000 probably had no idea. Probably no one told them. Here's why we built this thing. They're like, OK, cool, I don't even care.

Wil Schroter: It's funny you should say I, I kind of forgot that I do that. You do, but, but a lot of times when I do my intro, like on my workshops, like I, I'm gonna do a a funding workshop here in a couple hours, uh, with, with our community. One of the things I mentioned is that this is my dream job. I just get to clients. Yeah, yeah, I, I tell our our our our clients, our customers, our founders, I say, this is my dream job. I just get to sit around and bullshit with founders all day. That's why I started this. And that is my why that this is the best part of my about my job is I just get to sit around and bullshit with founders like I tell people if you love sports, this would be ESPN. Like this is our podcast, right now same with this last night, in the whole time that we've been doing this podcast, it's. It never occurred to me why we do this podcast. Like at no point did you and I ever really sit down and come up with like a business narrative or use case of why to do the podcast. We just started recording it for years and years and years and hundreds and hundreds of episodes, and at no point have we really sat down and said, OK, well, like, you know, why are we doing this or, you know, what's the narrative, etc. We just kind of did it. I think we knew it aligned with our why. Yeah. And so we just recorded it,

Ryan Rutan: right? That's it. I I think that was because our why was still present, we didn't have to question all that, right? It just, it was like, yeah, this fits, this falls in with the greater why. We don't have to ask why specifically about this thing. I think that's one of those things that's so important about this entire concept is that when you keep it front and center, things tend to be built with alignment in the moment. Right. When you don't. Then you end up with things like the pivot or you know, the reallocation of resources or all these other shitty business processes that we end up having to go through because at some point we realized we built the wrong thing. Right? Or we built it in the wrong way or we built it with the wrong people or for the wrong people because we lost sight of that why?

Wil Schroter: I remember specifically it's like one moment in time, we're at a board meeting, this is uh when we're running the ad agency and the agency had become pretty big. We're we're at about 700 million in revenue at this time, and we're we're at one of a gazillion board meetings and in the board meeting, the board meeting is different in this case because they were just officers of the company that owned the board meeting. We're a private company, we didn't have shareholders, and I remember I, I asked the board. I said, every one of these board meetings is about HR or company structure or finances or whatever. I was like, you know, we haven't had a single board meeting about creative, and we're a goddamn ad agency. We're ad agency. We've literally

Ryan Rutan: never thought it might be important.

Wil Schroter: We've literally never talked about our actual creative product in a single board meeting for like years.

Ryan Rutan: Um, the why just gets taken for granted at some point. It's like that, it's. Like that, you know, that sweet friend who's always there for you, even when you ignore them and forget about them and leave them behind, right? And it's like, man, just take care of that thing.

Wil Schroter: In in a weird way, if you didn't know we were a creative agency and you sat in those meetings, you'd have no idea that that we actually created creative for a living. It it never came up. And look, I mean, there's business purpose for that, but that went back to my earlier point in that the why. You know, of, of we're gonna build great creative got lost in the business of creating great creative so

Ryan Rutan: necessary, right? You, you have to have that because it contextualizes all of those other business purposes, right, right? Because without that, then the business can can take on counter purposes, right? You got things just start to branch off and go in different ways. How often do you see that? We like silly silly stuff, just like misalignment between sales and marketing, right? Two departments that should be really easy to keep in lockstep because they're so closely aligned with what they do. And yet when you lose that why, those things again, starts with just a couple degrees of separation and then before you know it, you can barely see each other over the horizon.

Wil Schroter: I think, OK, bringing back the why. I think what we have to do when we start to bring it back, is we have to start to isolate and say, where is it being lost. It's it's not this one big global thing. We have to assign, if we, if we're really militant about it, we start to look across the organization, and we start to assign, not blame, but course correction. Where in the organization is he, is he getting lost cause that, right, right. Where is it getting lost? OK. Sometimes that that's in reporting structure, right? In other words, like, oh man, like I, I handed essentially culture and that's what we got got lost to HR and HR just whitewashed the whole thing, right? It happens, right? It does, yeah. Not blaming HR, but you know, I'm just saying, right? Or I handed this role like product, like think of Steve Jobs back in his day. If he had handed product, right, not that he ever would, but like had handed product to someone else. And that person kind of lost the why, you know, made not Steve Jobs level kind of ballsy decisions, right?

Ryan Rutan: I'd still be typing on a clicky keyboard on a phone,

Wil Schroter: exactly, right? You had a trio, but like, uh, it, it's things like that where you can start to look and say, yeah. Shit, like that's, that's where the Y got lost. Like you can triangulate and start to say, ah, OK, there are people in places and processes where Y got lost, and you can try to recapture some of that. Now I'll say this, sometimes why is goddamn gone. Right? Sometimes why is dead and buried, and it ain't coming back, right? So, so it can't always come back. It does happen and sometimes you gotta let it go. I see founders that that look, look around, I was one of them and say, you know what, ain't coming back. Time to move on and go build something else. I did it 9 times. So I'm quite familiar with that process, and that's OK too. Sometimes the the fastest way to regain it is start something new.

Ryan Rutan: Yeah, just start something new, go back to a new why. Yeah, I think it depends on, I think it depends a lot on, on why it died and and like what sort of effort it takes to bring it back. One of the things I like to do is to kind of simplify this exercise for founders. If you're thinking about what we're talking about right now and you're trying to decide like, OK, how do I go and find this stuff again? Two places I start. Just super, super basic, right? And we talk about this quite a lot on the podcast in different contexts, but first I look at the things like what are the things that we're doing that I wish we weren't doing, right? What are the things that we've started to do by virtue of becoming the company that we are now, by by being run by the market or customers or or staff or whatever it was, or we lost control and we ended up having to do stuff we don't do. What are those things? Yep. What are the things that we wish we weren't doing? Right? Because it will almost always map back to some divergence from our why. Yep. Then I, then I look at the things and I say, OK, what is it that I want to be doing that we're currently not? Are we in an office when we wish we were remote, right? Are we servicing corporate clients when we wish we were working with with small business or startup founders? Are we, you know, hiring people left, front and center, we have no connection to that aren't improving the culture instead of just building software that could do the same thing, or vice versa. We build software and take the heart out of the company and we should have made it more people. So what are those things that we're we're not doing that we wish we were? And for me then like the gaps that that appear in those things. Inform the process that you just described, which is then I start to go look in the organization, say, OK, where is the responsibility for this? Where do these things initiate? Where does the process break? How far down the food chain do I have to go to find where this begins to bubble up? Is it top down, is it bottom up? Yep. And that makes the exercise a lot easier for me because I think that if if we leave it like this kind of amorphous, just start to go look around the organization and see where things are off the rails. Unfortunately, every time I start to do that, you find things that are off the rails, but what do you find first? It's not the symptomatic. Stuff around the why. It's, it's the business processes. It's the, well, this person just not doing the thing right, and then you get caught up again in the what, the how, the who, instead of the why. And so that's why I always try to start with those things in mind. And if I can have my North Star and my my South Pole, which is the things I want to do and the things I don't, that makes it far easier for me to then enter into the the brutal exploration of like, OK, now how do we bring

Wil Schroter: it

Ryan Rutan: back?

Wil Schroter: I agree and I think again, we deserve to bring it back. We're entitled to our why. Say that again.

Ryan Rutan: Say

Wil Schroter: that again. We deserve to bring it back. We're entitled to our you heard it here. You heard it here,

Ryan Rutan: bring

Wil Schroter: it

Ryan Rutan: back.

Wil Schroter: But that's the thing, like, it's our job as much as it was for us to start this thing, it's also our job to bring it back again, you know, going back to our our man Steve Jobs, he kind of did that with Apple. He did exactly that, right? He got booted out and he brought it right back, right,

Ryan Rutan: and you know back in, yeah, exactly why, by the way, right, it's it's a full case study

Wil Schroter: this. Exactly. uh, he brought it back and so here's what I would say for all of us. It is a constant battle to maintain the why. It is damn near impossible to keep it going the entire time. It is hard as hell. It is a full-time battle to keep the why front and center, right? And it will slip. For many of us, it's slipped a long way, but for all of us, it's our job to bring it back. We owe it to our Ourselves and to some degree, we owe it to the company, OK? To bring the full front and center, make it part of our DNA, keep it part of our DNA, enforce function that thing the entire way to build the company and keep the company for what it was meant to be from day one.

Ryan Rutan: Overthinking your startup because you're going it alone, you don't have to, and honestly, you shouldn't because instead, you can learn directly from peers who've been in your shoes. Connect with bootstrapped founders and the advisors helping them win in the startups.com community. Check out the startups.com community at www.startups.com to see if it's for you. Could be just the thing you need. I hope to see you inside.

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