Welcome back to their episode of the Startup Therapy Podcast. This is Ryan Rutan joint, as always by my friend, the founder, and CO of startups.com. Will Schroeder will have you ever walked into something that you've built entirely from scratch? Ground up, zero to one moment. Then wandered through the doors and just felt like you no longer belong there. A lot. There was not like many times, but like, like an 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 at time. I'm like 26 as it's getting bigger. I'm sitting there going. Okay. Well, you know, I used to build websites that was, you know, part, 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. Yeah. 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. Yeah. Like, I'm managing, I'm, I'm having meetings about meetings. I don't produce a goddamn thing. Yeah. And it was miserable. Yeah. Miserable. Right. It's funny, ma'am, 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. Let me tee that up a bit.
So a lot of times what'll happen is, you know, you and I'll talk to founders and you can tell that like they appreciate what they've built. Yeah. But they don't like their job anymore. Yeah, yeah. Oh, a hundred percent. And, and I guarantee we've got a fair amount of people that are listening to this, this episode be like, yeah, that's me. And 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 two new a hundred thousand square foot buildings. We had, you know, six 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, 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 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 when 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 right. 20 at this point. 21, 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 it, you were the silver-haired 60-year-old that finally made it to the, the corner office type thing. Yeah. Climbed your way from, yeah, from nowhere to you. I It was all about the, a career trajectory, right? Yeah. Like that all got turned on its head in the startup world where you're like 23 in the CE 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 kinda 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? It's thrust on you. It's thrust on you. Yeah. I mean that's the, the, going back to management philosophy from that same period of time, that's when the Peter principle 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, 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. 'cause you were a great coder. Turns out you've never managed anybody before. I watched that happen. Right, because as we were scaling you, as we were adding more and more people, same exact thing you said. Yeah. Specifically.
I remember one of our, our senior developers kept getting promoted Uhhuh, and when I say kept getting promoted, it didn't happen outta nowhere. I was promoting, but as I was watching it happen, I saw him get more and more uncomfortable. Mm-hmm. Good, smart guy, right? Yep. I could tell he was getting moved to the top of the ranks only because he had the senior most technical knowledge. Yeah. Right. Like he was more technical than anyone else.
But as a manager, like he, he wasn't gifted in any way. Yeah, 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. I was like, maybe you just wanted company for the misery. Like, yeah, yeah, I gotta make sure I'm not alone in this misery. 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, 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, right. 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 cold fusion, whatever it was, you know, a hundred thousand years ago in. So, you know, like that to me was a big part of it. And so I think fold. Like I also wasn't a talented manager by any stretch of the imagination. I was not right. I, I'd 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 management. Sure, sure. 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 Christiana Ronaldo, and he's getting old now, so we may be getting close to this point, but let's say Christiana Ronaldo from, from five years ago, six years ago, prime peak performance, and all of a sudden you're like, you know what? This guy's 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.
Do you think that guy wants to be watching the game? That's how I felt every single time I was managing people felt like I'm watching the game and having to coach them through it. I'm like, I want to go kick the damn ball. I don't wanna be off the field. Painful, super painful. I was like, in short order. I was like, man, I missed the days when we'd all stay up all night, like working on a project and just crushing it. Yes. And and now it's like, yeah, no one wants to do that. No. Right.
Like the only reason we did that is 'cause you, you did it right. Like, you know, you pushed us to that end. 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? Mm-hmm. And we had to move everybody to the basement. You remember that? Where everybody went to the basement for a little bit and like we were down there basement. 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. Yep. And on two or three 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? 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 pew gone. Right. Such a bad feeling. I think it's hard for us, uh, you know, as the founders to take stock in that. Yeah. And to be able to say, ah, okay. The good old days. We're, we're only good for me. Right. Or said differently. Like, 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. It was fun. That was 20 years ago. You were great. Yeah, but I get it right. Uh, like that part of is long since over, and I think as managers, as founders, we, we get into this spot where we long for those days.
And what's so hard is we're the one in control of where this company is gone, but the company evolves beyond us. Yeah. 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 wanna grow with it? Do we wanna change? 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.
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. Yep. 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, I think you and I have used the example before where like, your best buddy from university was a talented coder. So you make him your technical co-founder at 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? And we feel guilty for not doing it. Yeah. 'cause 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'd 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 'cause we needed the HR person. Yeah, we needed the CFO we needed. But I don't really like them. I don't wanna 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. Right?
Yeah, exactly. It's my own company. Right, because it's Because it's changed so much. Yeah. You've gone from, you went from Play-Doh to Legos, right? It went from full on, freeform, messy. Make it into whatever you want, smashed it up, start over again easily as you can to something where everything's 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. I sat across from the, the guy I mentioned that we'd kinda 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. Yeah. And so I sat down with him.
We were 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. Like, again, don't tell me the age. Please don't tell us the age. Don't say it out loud. Will 32. Oh, he was 32. God. Right. I was talking to him like he was 72. Okay. And I, I remember being like, you know, at this point in your career, in your life.
Yeah. You know, like where things have changed or I mean. I gotta 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. You amazing code, amazing a, uh, 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, like, yeah, I can just do what I enjoy.
And again, I could tell we'd kind of like pushed him into this, 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 that. No one tells you that. Right, 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 immaturity?
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, 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. 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 a thousand times before you, which means the answer already exists. You may just not know it, but that's okay. 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 [email protected]. 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. Okay?
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, 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 are like the, the two critical decision points. One is, here's what I want to do. Like, maybe I just wanna 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, uh, 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, and I'm willing to do it. Right. I think part of it is, this isn't me just being arrogant, like, you know, or entitled. Right. I'm willing to do the job I am. Yeah. 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. Yeah. Like, like ops. Yeah. Right? Like and so there are some people that love it. No, really that's to 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? Right, right. It's an entirely different decade. Yeah, exactly. And, uh, and so, you know, I brought her in to kind of be that, that, that ops 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.
Yeah. And becomes pretty obvious that they also don't like the way you do that job. That's what I'm cases, right? Yeah. Right. Like 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. Which is the, the the other part that I wanna put in here. Think about the cost. Oh yeah. Of doing the job you don't like poorly. 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 shown 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 Yep. Than doing your performance review.
Right. And so I think the same with the, you know, the, the leadership, the founders, what, what have you. Your team can tell if you're doing a job you don't want to do for sure. And that's a really bad look. 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 a thing that you really love, which is probably why they decided to follow you into startup, dim in the first place a hundred percent. And now you're this entirely different human that no longer fits. Yeah. And, and again, there's an enthusiasm that comes with it, right? Yeah. 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.
Yeah. Uh, during the meeting. Be like, how can I get outta the meeting that I started? Whereas like if we're, if you and I are on a whiteboard developing product Yeah, we're brainstorming. I could be there forever. Yeah, exactly. Like someone will have to come in and tube fetus at some point, like we're Yeah, 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? Yeah. And, and again, I think it's, it can be a really hard question because there's so many other influences I. 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 I. 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, to do that at that point, which was nice.
But it was difficult, right? The first was the acknowledgement 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, right, for this specifically, uh, 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 okay 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. I looked at it as a failure. I looked at it as a hundred percent, and again, and 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 get it and I'm, I'm grateful. This wasn't a lack of gratitude. I'm grateful yeah, for this opportunity, but I don't want this job. Yeah. It's a very weird thing to say as the leadership of an organization.
Yeah. Like I get it, but I don't want this job. I mean, like your parents saying like, I get that we're supposed to look after you, but yeah, you're kind of on your own. Well, it goes back to what, 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? Mm-hmm. Somebody else was able to say like, Hey, what if you just didn't do this?
Like there's just 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. Right. Particularly at at a time where you're questioning who you are. 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. I. 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 kind of, I've done what I needed to do. There's like, if, if, if we grow 10 x more. It'll make no difference. What's me being there will make no difference whatsoever. Yeah. Which is kind of hard, uh, self-realization, but, so I just went and go, did something else. Right.
Started eight other companies. Yeah. I think I had at least the, the self-awareness to realize that what I was doing, even though it was successful, I. It wasn't really what I wanted to be doing. Yeah. 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 ruining 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. What happens when.
This, 'cause this can sometimes be taken outta your hands, right? We, I, I said before that nobody's gonna come to you and say, Hey, what if you just did 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. So what happens at, 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 this survival of the company? Right.
Like I, I, I'm not a big fan of ever taking the founder outta the business. Yeah. And don't get me wrong, I'm not saying every founder is uniquely qualified. You know, I wasn't Right. But you know, you know, I've talked about this a lot. I, 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, they would've never been able to get this job if they hadn't started the company. Totally get it, right? Yeah. Get it. And now that they're here, uh, the company's 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 outta the park. This is always with private equity.
Private equity is whole thing is they come in, they buy a company, they shred it apart, so like they, to get the cost down so they can sell it to 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 better on paper. Yes. Actual company. Right. In any other way?
Rarely. Every time I hear somebody's, I'm working for a company and they're private equity backed, 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, yeah, yeah. Oh no. It's wonderful. It's great. I've never had someone so Oh, oh no. It's wonderful. Yeah, 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. Yeah. We have to make a transition and look 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? Yeah. You built something that managed to pick up enough steam that it outgrew you and can out 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. It's sending the kids off to college. Right? The the whole goal was to, was to that, to too close to home. Now will, we're getting real close to that buddy. That's that.
To be like, ha ha, so far in future, doesn't matter. Not talking about me, are you sir? Damn. I. 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 they're about the same age. I saw a teenager walk in the room and she's teenage 13. Right, dude. But I mean, I saw a, yeah, a young woman. I didn't see, I didn't see my little girl anymore. I saw a young, I double. I had to dig a double take.
Yeah. Because how was it? What the hell? We just walked through. Yeah. Who was that? Right? It was weird. And so. 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 five seconds. They're outgrowing what we currently know now. Like as a parent, we don't get to choose whether we wanna 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 teacher. Pretty soon 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 very similar feeling. Very, very similar feeling. That's the thing, like it's a trophy. The fact that we made it this far, like is is heart wrenching? It 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 wanna mourn what happened, okay? I wanna celebrate what happened.
I wanna celebrate what we've built. How we've built it and the fact that, and you said it, Ryan, 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. 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 [email protected] to see if it's for you. Could be just the thing you need. I hope to see you inside.