Ryan Rutan: Welcome back to the episode of the Startup Therapy podcast. This is Ryander Tan joined as always by my friend, the founder and CEO of Startups.com, Will Schroeder. Well, have you ever walked into something that you've built entirely from scratch, ground up 0 to 1 moment. And then wandered through the doors and just felt like you no longer belong there.
Wil Schroter: A lot. Now there was not like many times, but like, like the overwhelming feeling of that. Early in my career, uh, when I was building a company, companies started getting big, like real big, as it's getting bigger, you know, I'm still young this time, I'm like 26, as it's getting bigger, I'm sitting there going, OK, well, you know, I used to build websites that was, you know, part of part of what we did as an agency, and I, yeah. I don't really do any code anymore, and now I don't do any design anymore and now I don't really do the the strategy anymore. And one day I walk in and I'm like, what do I do here? Right? Like I'm managing. I'm, I'm having meetings about meetings. I don't produce a goddamn thing. And it was miserable, miserable, right? Well,
Ryan Rutan: it's funny, man. You just described it. I had the same thing happen to me. I've seen this happen with countless founders where it's like one day you just walk in, it's as if you walk into a glass wall. It felt that way to me. It was like it was such a sudden sort of thing where it's like I was the last one to kind of know that the company had had moved on and that I no longer fit there, and it, it felt like such a betrayal of everything I'd built. I'm like, this is only all here because of me, but now I don't need to be here like, what the F? Like I didn't know how to deal with it.
Wil Schroter: Let me tee that up a bit. So, a lot of times what will happen is, you know, you know I will talk to founders, and you can tell that. Like they appreciate what they've built, but they don't like their job anymore. Yeah, 100%. And I guarantee you we've got a fair amount of people that are listening to this, this episode like, yeah, that's me. But here's the problem, we feel guilty about it. We feel guilty that we don't like the job because it makes us ungrateful. I walk in and I remember at the time, you know, we just built these 2 new 100,000 square foot buildings we had, you know, 600 or 700 people at the time, and I'm like, I should be so. Proud of what we have here, and I am, and I don't like my job. And this isn't me being like entitled. I just didn't like what I was doing anymore. Like there's nothing wrong with that. I, but definitely didn't know that. It's
Ryan Rutan: funny, we go through some of those things at the early stages too, right? Where it's like there are lots of jobs that have to be done as a startup founder, you're doing it all right. It's chef cook bottle washer, right? You're doing it all. And we're sort of used to it at that phase, but I think we get into like where we start to hit our stride and our superpower, the company starts to grow based on that. And then all of a sudden that goes away again and you're like, but now what I'm doing isn't what I like to be doing. I, I know I've shared this with you before, but there was a point at which I was running my agency, you know, back in the dark ages, and it had been like a two week period. I was looking back at like my my daily journals, it'd been like a two week period where I had done absolutely nothing but keep the three most important teams in the business from fighting with each other. I had just become like, I was just dad. And I was unprepared to be a father at that point. I was 20 at this 0.21.
Wil Schroter: Yeah, and look, and, and some people love it, some people like that's what they wanna do. Like I remember, I remember when I was growing up and I was reading about like superstar CEOs, right, the Jack Welch era, right, where it was like you were prided on being an employee, right? Like now it's all if you're not the founder, no one cares, right? But that was a different era where like if you were the silver. 60 year old that finally made it to the corner office
Ryan Rutan: type thing climbed your way from from nowhere.
Wil Schroter: It was all about a career trajectory, right? Like that all got turned on its head in the startup world where you're like 23 and the CEO and you kind of started backward, but not too long ago, or maybe it was a long time ago, and I'm just getting old, not too long ago it was all about moving up to the C-suite. Those people were career managers, like the way you got there, like, here's the thing. You couldn't have possibly been prior to that, right? You couldn't have possibly been Mark Zuckerberg, and you just coded your way to the top, right? Like you coded and you wound up at the top cause you started at the top. And so it fascinates me that like in this in kind of this new world, these folks that came in as like the really talented coder, let's say, just as an example, wake up one day and they're like, I'm a manager now, like, what the hell just happened? And it's thrust on you. It's thrust on you.
Ryan Rutan: Yeah, I mean it's the, the going back to management philosophy from that same period of time, that's when the Peter principal was born, right? Where you get promoted up to your highest level of inefficiency, you're, you are a great junior coder, we'll make you a senior coder. You're a great senior coder, we'll make you a whatever the next level of that is, then you become a director of technology or something where now you're no. Longer coding, you're managing the other coders because you were a great coder. Turns out you've never managed anybody before.
Wil Schroter: I watched that happen, right, because as we were scaling, as we're adding more and more people, same exact thing you said, specifically, I remember one of our, our senior developers kept getting promoted. Now when I say kept getting promoted, didn't happen out of nowhere. I was promoting. But as I was watching it happen, I saw him get more and more uncomfortable. good smart guy, right? But I could tell he was getting moved to the top of the ranks only because he had the the senior most technical knowledge, right? Like he was more technical than anyone else. But as a manager, like he, he wasn't gifted in any way, right? To your point, he just kept getting pushed there. The irony was the guy pushing him was having the same exact problem, which was me, right?
Ryan Rutan: Maybe you just wanted company for the misery. I'm gonna make sure I'm not alone in this misery.
Wil Schroter: So we get to this point where like the company that we built. Right, was built for who we were, not who we are. And I think that's a hard thing for us to step back and say,
Ryan Rutan: huh. And I think for a lot of reasons. One of them for me was that When I realized I was doing management, and you've drawn this distinction before too, which is the difference between management and leadership. I'm not even gonna go as far as as leadership. It wasn't that I was like there were points where I was leading the company versus versus managing these people. My own individual ability to produce felt taken away. And so for me. That feeling that was the most overwhelming, like the literal like choking out my oxygen anxiety level, like worrying about this stuff, was when it would feel like because I had to manage people, I couldn't go do things that I found more important, more engaging, more exciting, more valuable, right? Like, whether that was going and trying to land a new client, whether that was figuring out a new way to deliver something, whether that was figuring out whether we should move from, you know, move to. Fusion, whatever it was, you know, 100,000 years ago, right? So, you know, like that to me was a big part of it. And so I think full like I also wasn't a talented manager by any stretch of the imagination. I was not, right? I, I had no experience. I had never even really been managed because I was so damn young, I'd never had a real, real job. And so part of it was absolutely a lack of skill and and probably a rightful amount of fear against. because I didn't know what I was doing, but the other part of it was it like, it took the fun away from me. Even had I been a talented manager, it's sort of like this. I look at it this way. If you're Cristiano Ronaldo, and he's getting old now, so we may be getting close to this point, but let's say Cristiano Ronaldo from from 5 years ago, 6 years ago, prime peak performance, and also you're like, you know what, this guy is the best player in the world, we should make him a coach so we can have a bunch more really great players. Hold aside that he may not even be a good manager. Yeah, yeah. You think that guy wants to be watching the game? That's how I felt every single time I was managing people. I felt like I'm watching the game and having to coach them through it. I'm like, I wanna go kick the damn ball. I don't want to be off the field. Painful, super painful. I
Wil Schroter: was like in short order I was like, man, I missed the days when we all stay up all night like working on a project and just crushing it. And, and now it's like, yeah, no one wants to do that. Right, like, the only reason we did that is because you did it, right, you know, you pushed us to that end.
Ryan Rutan: I don't know if you'll remember this there was a point at which you remember when we, we were refinishing the upper floors in the offices on Manning, right? And we had to move everybody to the basement. Remember that where everybody went to the basement for a little bit and like we were down there. It was, it was a war zone. We had video game machines down there. We had weight racks, we had desks. Piled on top of each other, and on 2 or 3 occasions, I tried to rally like, let's pull an all-nighter and get this done. Let's bang through these clients, whatever. And it was like I was like, yeah, I felt like, who was the politician that did that awful yell? Do you remember that? the scream heard around the world where he was anyways, there was no answer to my rally cry. I was like, let's do it, and everybody else is like, um uh time for drinks or whatever, and they're gone, right? Such a bad feeling.
Wil Schroter: I think it's hard for us, uh, you know, as the founders to take stock in that. And to be able to say, ah, OK, the good old days are were were only good for me, right? Or said differently, you know, there's always people like, oh my God, I remember when the company was smaller and we all hung out and blah blah blah, and that's great. Yeah, but it's also you have to take stock and recognize that like that's over. It's the guy who keeps talking about that one party from college and you're like, no, I get it. I, I get it. That was 20 years ago, right? Yeah, but I get it, right? I like that party is long since over. And I think as managers as founders, we get into the spot where we long for those days. And what's so hard is we're the one in control of where this company has gone, but the company evolves beyond us. That's what this is all about. The company evolves beyond us. It's one thing when it evolves evolves beyond everybody else, it's really hard when it evolves beyond us. So the question becomes, do we want to grow with it? Do we wanna change?
Ryan Rutan: It's hard, and I think this is, it's it's a question that it can be really difficult to answer at that point, with the point where you have to answer it, because you might not be well armed for it, right? You're, you're now realizing that there's a new, new world order. I have to have a different set of skills, I have to have a different set. And, and so you're, you're simultaneously asked being asked, do you want to do this thing? Are you capable of doing this? You know, even if you say you want to, can you do it? We've seen this happen too, like sometimes companies legitimately outgrow. the founder, or we see it outgrow one of the founding members. I think you and I've used the example before where like, your best buddy from university was a talented coder, so you make him your technical co-founder and CTO five years later when he has to run a dev team, it doesn't work anymore. It's just broken. It can't do it, right? It doesn't work. And so it's at that point where I think it becomes really difficult to say, do I even have enough information now to assess whether or not I should want to do this?
Wil Schroter: And we feel guilty for not doing it because we're like, you know, let's say we've raised, raised money, right? Now we're like, look, the whole point was to grow this thing, or at least so I thought, um, I hadn't, I hadn't experienced this part where I didn't realize that as this thing grew, I would become less happy, but now this thing has grown, it's a real joby type job. I don't like it. Like I just like, I don't get to do the things that I enjoyed and how we got here. I'm surrounded by a bunch of people that I kind of had to hire because we need the HR person, we needed the CFO, we need, but I don't really like them. I don't want to spend more time with them. I don't think a lot of people talk about this. You start to look around and you're like, if this company was hiring, I wouldn't apply,
Ryan Rutan: it's my company because it's because it's changed so much, you've gone from, you went from Plato to Legos. Right, it went from full on free form, messy, make it into whatever you want, smash it up, start over again, easily as you can, to something where everything is now standardized. Everything came with an instruction set. There there's a clear thing we have to go do and we just have to repeat that over and over and over again, and all of a sudden it's like, yeah, I don't wanna do that anymore.
Wil Schroter: I sat across from the the guy had to mention that we'd kind of made like a CTO if you will. I had definitely, he wouldn't say it, but I could definitely read it on his face that he was clearly in a place where like he just wasn't happy. And so I sat down with him. I remember sitting down with him in my office and what's funny is like, I'm talking to him like, now I remember talking to him as if he was like this really old guy, right? And I felt awkward that I was 26 and he was really old and he had a family and like.
Ryan Rutan: Tell me the age, please don't tell us the age. Don't say it out loud,
Wil Schroter: Will. 32, he's 32, right. I was talking to him like he was 72, OK? And I, I remember being like, you know, at this point in your career in your life, you know, like where things have changed I mean, let me give you an idea where my perspective was, right? Anyway, anyway, I'm like, you know, you don't have to be a manager. You're, you're an amazing developer, amazing coder amazing systems architect. Do you want to just do that? And and I remember like just this moment, this look on his face like, I can, I can, yeah, like I can just do what I enjoy. And again, I could tell we'd kind of like pushed him into this.
Ryan Rutan: But how lucky was he in that moment to have somebody else that could tell him that? Yeah, as a founder, no one tells you no one tells you that, right? And and I think that a big part of that is because if you think about that decision. If you think about what's wrapped up in that. It's a highly contrasted coin with two sides, right? Because if you refuse to evolve, is that just founder maturity, or are you just not mature enough to do this? Or is it like the exact opposite, which is that you are so self-aware that you know you're not capable of doing this thing, and damn are those two things a long way apart with you sitting in the middle going, I don't know, I just don't know.
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.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. OK, so, so if we're being introspective about it, and we say, hey, on the one hand, like I'm kind of committed to this thing, right? You know, uh, whether I raise money or whether I use my own money, whatever, like it's it's my baby, right? Like, I'm kind of committed to it. If I don't move forward with this. What does that actually mean? Like, it's one thing for you and I to say like, like kind of amorphously, hey, you don't have to, you know, love it or you you might not like your job, but you still have to respond in some way. And so, here like the, the two critical decision points. One is, here's what I want to do, like, maybe I just want to go back to building product or do sales or do whatever. And then here's what I think I have to do. When and when I say I think I have to do. Because in my mind, I believe that if I don't keep doing that thing, that thing that I don't want to do, that I'm gonna be in a position where I'm gonna get fired or, you know, the board or or my my employees or whatever are gonna look down on me. Part of it, and most people just don't understand this. It's just being honest. If this is a job, you know, that that I'm, I'm here to do the CEO job or you know C level job, whatever it is, I get it, I get it, and, and I'm willing to do it, right? I think part of it is this isn't me just being arrogant. Like, you know, we're entitled, I'm willing to do the job. I am. Yeah. However, the job that I'd really like to do, the one that I think I could be more effective at, is this. By the way, just before I complete that thought, a lot of times what that thing is, Ryan, and I think you've seen this with plenty of other companies, is like day to day management, like, like ops, right? Like in there
Ryan Rutan: are some people that love it.
Wil Schroter: No, no, that's the point, that go find them. And I remember at the time, I had found a a person that was working for us, uh, that was on the staff, I should say, and she was amazing. And I remember. I remember thinking she's so experienced. She's been around for so long. She was 31, and, and again, she was 61 in my mind, you know,
Ryan Rutan: right? It's an entirely different decade.
Wil Schroter: Yeah, exactly, and, uh, and so, you know, I brought her in to kind of be that that that op COO person and it worked out great, and it worked out great, but it made me realize how much I hated that job and how much it becomes obvious to everyone that works with you that you don't like that job.
Ryan Rutan: Yeah, and it becomes pretty obvious that they also don't like the way you do that job
Wil Schroter: in a lot of cases,
Ryan Rutan: yeah. Not only do you not like it, I don't like it when you do it either, right? You're just not a great manager, go away.
Wil Schroter: Which is the the the other part that I want to put in here. Think about the cost of doing the job you don't like poorly, right? Like, if you're phoning it in or trying your hardest, and you're just not that good at it, right? Take, go back to my developer guy, my CTO guy, right? In his case, he's showing up every day and he's doing a job, the the CTO manager job, or he's doing you know performance reports and all this bullshit, right? And but what he wants to be doing is writing code. So it becomes pretty obvious to all the people that work with him that he'd rather be writing code than doing your performance review, right? And so I think the same with the, you know, the, the leadership, the founders, what have you, your team can tell if you're doing a job you don't want to do, and that's a really bad look.
Ryan Rutan: Yeah, and then sometimes there's such a huge contrast to it too, which I think part of why they can understand that that you're you're mailing it in, because they have seen you on fire. They have seen you at peak performance. They have seen you doing the thing that you really love, which is probably why they decided to follow you into startup doom in the first place. And now you're this entirely different human that no longer fits.
Wil Schroter: Yeah, and, and again, there's an enthusiasm that comes with it, right? Never at any point did I walk into a meeting about an upcoming meeting with any level of enthusiasm, right? Like I'm checking my phone or my watch the entire time, uh, during the meeting, be like, how can I get out of the meeting that I started? Whereas like if we're, if you and I are on a whiteboard developing product, we're brainstorming, I could be there forever.
Ryan Rutan: Yeah, exactly. They will have to come in and tube feed us at some point we're, yeah.
Wil Schroter: Exactly, right? So, part of what we're talking about is how it affects us as founders, so that, you know, whether or not we've grown. I think also by proxy, you know, we're also talking about how do we see this in in our team, right? Where we've essentially put people in positions that they probably shouldn't be in, or we, we haven't stopped to maybe reaffirm? Is this really what you want to keep doing?
Ryan Rutan: Yeah. And and again, I think it's, it can be a really hard question because there's so many other influences. you know, depending on like, is the business on an upswing? Is the business on a downswing? Has it plateaued and just been doing the same thing for a long time, that can absolutely change your emotional state, which is clearly gonna impact your, your ability to make the decision. And look, I think part of it for me was was the realization that Adapting my role, didn't mean changing who I was. At that point it meant letting go of something that that I was hating, so that I could do what I loved, and I, I was able to find a way to do that at that point, which was nice, but it was difficult, right? The first was the acknowledgment of Oh, I'm actually not good at this. And then having to make the decision that yes, there was probably some effort that I could put into it that I could, you know, the the irony being that I was in a business management track at the time, right? I was in university for specifically, it tells you something about the quality of that education. Um, and so it really came down to me having to just recognize it first and then become OK with the idea of letting it go versus saying, well, no, I, I figured this other stuff out, I'll have to figure this out too, and not forcing myself through that keyhole, right? That was, that was the really hard part for me.
Wil Schroter: I looked at it as a failure. I looked at it again, and I. I was young in my career, so I, I honestly just didn't know any better yet. I looked at it as, look, you did this thing, you're now a CEO of a company. Here's how you're expected to act and behave and, and, and how you're supposed to enjoy it and embrace it and all these things. And I, I was just like, yeah, but I don't. Like I, I, I get it and I'm, I'm grateful. This wasn't a lack of gratitude. I'm grateful for this opportunity, but I don't want this job. It's a very weird thing to say. As the leadership of an organization, like I, I, I get it, but I don't want this job be like your parents saying like, I get that we're supposed to look after you, but yeah, you're kind of on your own.
Ryan Rutan: Well, it goes back to what I said before when you were, you were going through the that scenario. It's like, but luckily somebody else told them that, right? Somebody else was able to say like, hey, what if you just didn't do this, like there's Nobody else to, not only is there nobody else to tell you that, there isn't even really anybody else for you to tell. It's a conversation you have with yourself and nobody else. Like that's super uncomfortable, particularly at a time where you're questioning who you are.
Wil Schroter: Also, this is a tough one. Sometimes the best place for you isn't at that company at all. That's the path that I took. Right, I essentially quit my own company. Now with that being said, I realized that the company had grown to a point where it didn't really matter if I was there anymore. So like when I say quit, it wasn't like I was rage quitting. I was like, you know, it's kind of, I've done what I needed to do. There's like if if we grow 10x more, it'll make no difference what's like me being there will make no difference whatsoever, which is kind of hard uh self-realization. But so I just went and did something else, right? So 8 other companies. I think I had at least the the self-awareness to realize that what I was doing, even though it was successful, wasn't really what I wanted to be doing. And and I think that that's a hard call to make. That could have gone very wrong. I could have spent the next 20 years of my life ruin the day that, you know, that that I made the dumbest decision to to not work at the one thing in my life that worked.
Ryan Rutan: What happens when When this because this can sometimes be taken out of your hands, so we, I, I said before that nobody's gonna come to you and say, hey, what if you just do this thing? But there are times where people do come and say, hey, you're not gonna do this thing anymore, right? It's called the board, it's called investors, what happens at that point, right? Is this a betrayal of, of, of the baby you raised or is this, you know, a necessary move to ensure the survival of the company, right? Like, I, I,
Wil Schroter: I'm not a big fan of ever taking the founder out of the business. Don't get me wrong I'm. saying every founder is uniquely qualified, you know, I wasn't, right? But you, you know, I've talked about this a lot. I, I, I think when you mess with the DNA like that, it rarely works. Like I, I get the argument every time. The argument every time is like, look, we brought this person in, they would have never been able to get this job if they hadn't started the company. Totally get it, right, get it. And now that they're here, uh, the company has grown beyond them. Uh, they can't see it. We can see it. Name your problem, right? I get it. I do. But I rarely see the next person that comes in, hit it out of the park. This is always with private equity. Private equity's whole thing is they come in, they buy a company, they shred it apart so like to get the cost down so they can sell at a profit. And I rarely see a company where it's like, and then private equity came in and and it was so much better of a company. I'm sure the finances got better. But I'm talking working there,
Ryan Rutan: on paper, in any other way, rarely.
Wil Schroter: Every time I hear somebody, I'm working for a company and they're private equity back, my first words are I'm sorry, I'm sorry about your loss, right? Like, because, and they all instantly know what I'm saying. I've never had somebody go, oh no, it's wonderful. I've never had someone so, 00 no, it's wonderful, right? They're always like, yeah, you get it. Here's what I would say. I think the hardest thing for us is, again, this concept that the change isn't a failure. The change isn't a failure, right? It's an evolution. It sucks. It's hard. It'd be great if things were just always the way they were in our halcyon days, right? But they're not, and here we are, and we, we have to make a transition. We have to make a transition. And look,
Ryan Rutan: like if your dream was big enough to outgrow you. That's not a shame. That's a badge of honor, if anything, right? It's a sign of like the ultimate success, right? You built something that managed to pick up enough steam that it outgrew you and can go on without you. Emotionally, that might be tough, but like if you just look at that from a purely objective standpoint, pretty damn cool.
Wil Schroter: It's, it's sending the kids off to college, right? The, the whole goal was to was to nurture that
Ryan Rutan: close to home now, Will, we're getting real close to that, buddy. That's that used to be like haha so far in future doesn't matter, not talking about me, are you, sir? Damn.
Wil Schroter: My daughter Summer walked into the room the other day, and I don't know if you've gotten this, I'm sure you have with your daughter Hannah cause about the same age. I saw a teenager walk in the room and she's 13, right? But I mean, I saw a, a young woman. I didn't see, I didn't see my little girl anymore. I saw a young, I, I had to take a double take because I was like what the hell was that? It was weird and so. But all these emotions come crashing through the same thing, right? Where I'm like, oh my God, like, to your point, she's gonna be in college in like 5
Ryan Rutan: seconds. They're outgrowing what we currently know now, but as a parent, we don't get to choose whether we want to continue that role, right? We have to continue to to level up. Like I figured out finally how to be the the parent of an adolescent. Now I have to learn how to be the parent of a teenager. Pretty soon I have to learn how to be the parent of a college student. Um, I suppose some of it gets easier as it goes on because they start to take over more and more, but a very similar feeling, very, very similar feeling.
Wil Schroter: But that's the thing, like, it's a trophy. The fact that we made it this far, like is is heart wrenching is to to to watch our daughters like pack up for college, right? On the other hand, and this is again the analogy, we have to realize what it took to get us here. Yes, it's tough. Yes, it's it's a very difficult part for all of us to be able to see something we built and nourished, kind of grow beyond us, and in some cases without us. But here's what I would say, step back for a minute, step back. I don't want to mourn what happened, OK? I want to celebrate what happened. I want to celebrate what we've built, how we've built it, and the fact that you said it right, the fact that we even have the optionality of being able to make this transition because a tiny fraction of a percentage of entrepreneurs will ever get this opportunity, and if we are one of the few, few, few that ever gets this opportunity, cherish the opportunity and make an important decision to move the hell on.
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.