Startup Therapy Podcast

Episode #221

Ryan Rutan: Welcome back to that episode of the Start Up therapy podcast. This is Ryan Rotan joined as always by Will Schroeder, my friend, the founder and CEO of start ups dot com. Will one thing we know about being in the start up space is that it's, it's a long race, right? It's a long protracted affair that we get involved in and time to time. Things happen where we step away, right? Maybe we wind down a start up, maybe we sell one things happen where we end up stepping away for some period of time from this space. What happens, right. Once we're out of the game for a while, we get fat.

Wil Schroter: No, no. I mean, like, I mean, literally and figuratively, I think that we talked to founders a lot where, like you said, they, they've exited the business and, you know, and they're kind of in that mode for a while or they've gone off and done something else. Like maybe they got a corporate job or something like that and they've been out of the game for a while. Few months, not a big deal. I'm talking when a few months turns into a few years and I was talking to a good friend of mine the other day, he exited his business about two years ago. Sold it off to A P, it has been kind of figuring out what's next. The problem with that is that over enough time of the quote, figuring out what, what's next? You start to lose relevance, you start to lose your connections, you start to lose your drive, you start to lose a lot of the things that made you the athlete you were in the start up terms. And so I think what I want to talk about today is what is that decay look like. What, what happens when we get to a point where all, you know, we're starting to become relevant anymore. If we're on the sidelines so long, people forget to put us in the game. And I think that's really for a lot of us, sometimes we don't see it. And I think some folks listening are definitely in this spot or worried about becoming in this spot and we'll talk about what to look for, how to avoid it and really how to get back in the game.

Ryan Rutan: Love it, man. Yeah. Yeah. And it's such an interesting thing too, right? There's so many things that kind of fall apart at that point, right? One of them being the, the community, right? That's around us. And I think that was the one that I felt most when I was no longer a start up founder for a period of time that all of a sudden all the people that I wanted to hang out with because they were, all my friends were also start up founders. But when I wasn't the start up founder, I didn't have the same relevance to them in that moment. Right. All of a sudden, I, the reason we hung out, yeah, we were friends but also because we had that common ground that that space. But when you know, I'm talking about, you know, doing 10,000 people software deployments for, for a start up, I'm in a corporate environment that I'm in versus a start up. It's not the same story, right? Not the same relevance for those folks.

Wil Schroter: Yeah, it's not. And, and I think that it's hard for us to appreciate how important that relevance was because it, it starts to become you kind of get it by osmosis, right? Where all of a sudden you're like, you know, what the industry trends are, you know, who the players are, you know, you know, when there's gossip happening that you should be paying attention to. Like there's so many things I see this with developers, with software engineers all the time where they were once the young hot coder that was in the latest technologies, et cetera and they grew up and built their career with that code base. Well, then the technology changes and then all of a sudden what was native to them is no longer native to them. It's native to the next version of them and they're outmoded. Right.

Ryan Rutan: Who wants to talk for Tran? Right.

Wil Schroter: Exactly.

Ryan Rutan: Nobody. Grandpa. Exactly.

Wil Schroter: And so I think that for a lot of us, especially earlier in our careers, we haven't been through this transition. We haven't been to the part where, like, wait, I'm not relevant anymore. Like I'm not part of the conversation anymore. And that happens at a industry level because, you know, industry is changing over time. It happens at a professional level, meaning your own skills. Yeah, exactly. Right. You're a CMO, you're in marketing, you're practicing these marketing skills which change on a dime every day. If you take a year off, you're a dinosaur. I

Ryan Rutan: can't even imagine. I'd come back and be like, all right. So uh how is a I progressed? They're like a I was so 2023 Ryan, it's 2024 now. A I ate itself and spit out something better. Cool. But I have no idea what

Wil Schroter: it is. And so it's totally different. So I think as founders, when I talk to folks, like my buddy, I just mentioned that sold off to a private equity company. I'm like, buddy, you gotta get back in the game. He's like, well, I'm not sure what I'm gonna do next. I was like, kind of doesn't matter. I'm not saying pick the first thing, do something, advice consult, get back in the game because the start up founder thing is a muscle and if you don't keep working that muscle, it becomes atrophied, it becomes ineffective. And it is real. Whenever we try to bring some founder that's been gone too long, kind of back off the bench, they're not always the same person. Now, that said a certain amount of rest is great. Right. You, you take a year off. Right. And you've never had a year off, I've never had a year off. You've never had a year off, right? Sounds great. But once you get kind of past that year, two year three, I have a whole other set of friends who 15 years ago had a start up that didn't work out. So I'm gonna take a quick break and I'm gonna work at a corporate job and they're still at that company, right? Nothing wrong with that. I'm not knocking it. But I'm saying that like at some point that start up muscle, right? Which is a AAA taste for risk, right? The ambition that comes with that, et cetera, you lose it if you don't keep practicing because we're

Ryan Rutan: not just talking about the skills, right? The skills is one thing, right? Like, because you can be in a corporate environment and be honing skills. A lot of people come out of corporate to start a start up based on their experiences within it. And so of course, there's a spectrum here, right. On one hand, there's rest which we talked about and that's healthy all the way. At the other end of the spectrum, we begin to atrophy, right. We begin to lose things and it's like you said, it's a muscle. So some of it's the skills. But yeah, some of it's the risk tolerance, right? Some of it's building a lifestyle that would not be in any way, shape or form sustainable if you were to go and start a start up that works within your corporate environment, right? The 401k, the health benefits all the other stuff that you have that if you had to kiss goodbye with a family of four might not work so well, right? And so the longer you stay out, the more that comfort becomes a a barrier to reentry to the start up space, I think,

Wil Schroter: let's stick with that for a second because I think you mentioned about having kids, et cetera. I think what's kind of interesting as well about, you know, this whole concept of life happening while you're kind of out of the game, nothing that's gonna happen. Typically, you know, outside of the game is going to feel more contentious or painful than what it was like inside the game. In other words, it's really comfortable to stay out of this because being in it was stressful as hell. And so at some point once you get used to be, get up, whatever time you want in the morning again. This is all about retirement, right? Or be able to shut off work at five o'clock because you have a regular day job, so to speak, which again, nothing wrong with it. If it works for you. I'm just saying it's really hard to go back and say, oh, man, I miss not being able to have my nights and weekends. Like, like those are the things that, like, you know, it's pretty easy to get used to, but it's

Ryan Rutan: that balance too, right? Because there's also that it, it's so, I think here's where it becomes important if you want to go do that and you're comfortable doing that and you find that that's what you want to be doing. Cool. I think we're talking to the people who at some point are gonna go, I can't do this anymore. I can't be Johnny Corporate Rater Jebp. I need to go do something else. Right. I wanna do my own thing. And so there's a danger in that I can tell a personal anecdote not related to start ups but very similar pain in terms of taking time off. I was a competitive soccer player for most of my youth, all of my youth and then into my early adulthood and then I stopped, I stopped for almost 20 years and then I realized it was something that I deeply missed really wanted to get back into. It's really hard to get back into a competitive sport after, after 20 years of delay of game, and I've gone through that pain, right, four years into kind of reactivating my soccer muscle. It's still up and down, right. And I'm, and again, here's the thing I think this is, this is also really important. One of the things I realized was I kept getting older, but as Matthew mcconaughey famously said, and they stay the same age. So did all the players, right? Like I keep getting older every year, but the people in the league are still the same 20 something as they were when I left. Different people, same age, same body, same, all of that, right? And so I'm now competing with that. That's also relevant to the discussion in the start up space because that's what happens, right? You might leave and you might think, oh, but I can come back like I'll go do corporate for 10 years. No worries. I'll just sharpen the blade and come back in. Well, nobody else is going through that process. They were still in it, they're still there. They are the product of whatever that current environment is, which makes them much, much harder to surpass or, or even just to join back in and become comrades, right? You become Steve BC. We in the uh carrying a skateboard around the high school, right?

Wil Schroter: Yeah. No, it's, it's really interesting spot where there's a big difference between taking a rest in like quasi retiring Right. I think when it becomes like, and you don't see it coming. That's the problem. So, another friend of mine, we had a founder group at my house uh recently and we're all going around, everybody's giving their updates and he had done for, to wind down his company and he go uh to get a job at a Fortune 500 company. Great job. Actually, he, he, he landed very well, but he's still in the founder group because one of the things we always say is once a founder, always a founder and he gives his update. He guys, dude, it hasn't even been nine months. And I need to get back in the game. And I want to point out a couple things when I say that he had a very difficult wind out, a brutal wind out of the many founders that I have shared with and I shared in groups, et cetera. He might have been one of the best shares I've ever seen. Like the most compelling, most honest, the most, you know, he's awesome. And so you would think given kind of the wound there and there's wounds for all of us that he'd be like, dude, I'm so glad I'm done with that. I never want to talk about it, never want to think about it. Never wanna. And again, he had a very great landing great gig and he's like, but I want back in, right? And it's easy to not feel that way. It's easy to get that big paycheck every, you know, every week and be like, man, you know what? This ain't so bad. It's easy to drive home at five o'clock, so to speak and be like, oh, I don't owe anybody anything like, you know, like I, whatever, it's easy if you've had a, you know, an exit of any size, even a little bit, it's easy to be like, you know, what, not dying to go back to all that stress again. Right. All of those things force that muscle to atrophy. Right. I think what we're saying is sometimes it needs to some, sometimes that's exactly the right answer. But what we're saying is you can't take it for granted. You do get soft,

Ryan Rutan: you do, you do, it's it, and it is such a tough decision. You know, we've done, we've, we've done a podcast on exactly the opposite, which was people who leave a start up, whether it was an exit or a failure or whatever and immediately jump back into something. We talked about the dangers of that as well. Right. You go back in too soon. So this is another one of those things where there isn't a time, definite period. We can't tell you what you need is nine months, two weeks, two days and four hours and then you're gonna be primed to go back again. But what we can say is there is certainly a too soon. And there's also a too late, right in your mind, which one is more hazardous, which you feel like has a, is a bigger impact which you've seen a bigger, bigger negative outcomes from the, the too soon or the too late.

Wil Schroter: Here's the way I'll put it. I'm, I'm gonna give you a bit of an, an analogy. If I take a vacation once a year I get a vacation that's longer than two weeks around the holidays, right? The end of the year. If I take a vacation for a week, I'm getting rested. If I take a vacation for two weeks, I'm getting fat. The difference is there's a threshold there where I've, I've gotten the rest I needed and now I'm just getting fat. Right? And that's really kind of where that threshold is. I don't know which day it was exactly. But I know at some point it changed from, I'm not just tanned anymore. I'm also, there's more of me now with that said, I think we also have to be mindful. This is what this episode is about, about taking stock of. What do I stand to lose by being on the sideline? Let's talk about your relationships, right? How many relationships Ryan right now do you and I have with people circumstantially just because we're in the game.

Ryan Rutan: 96% of my relationships,

Wil Schroter: dude, right? Like literally the only reason I know investors is because I'm in the business where investors are like, I wouldn't hang out with these people. Otherwise not bad people. Nothing, not knocking investors but like, they probably wouldn't hang out with me either. Or, you know, all the start ups that I know. We all like vendors that I know, or, um, news journalists that I know. Like, I know so many people. I have 10,000 names in my phone. Right. I know all these people if you took out what I do and you said ok, now it's just the people that you have like daily commonality of you both have kids the same age. There's like 12 people on my phone and they're great. That's fine. That's enough. I'm not, I'm not complaining. You know, something that's really funny about everything we talk about here is that none of it is new. Everything you're dealing with right now has been done 1000 times before you, which means the answer already exists. You may just not know it, but that's ok. That's kind of what we're here to do. We talk about this stuff on the show, but we actually solve these problems all day long at groups dot start ups dot com. So if any of this sounds familiar, stop getting about what to do. Let us just give you the answers to the test and be done with it.

Ryan Rutan: But that's a good point because that's, that's all of those that you would need. Right? Meaning that the rest of those people wouldn't be relevant to you if they were also only those criteria of overlap. Right. So the same thing happens for everybody else. I think this is one of the things, this is one of the dangers with this piece in particular relationships and relevancy is that we don't see it the way that everybody else is going to, we assume we were friends before we'll still be friends after. Well, ask yourself the same question if that person was no longer exactly the person that they are for you right now, would they still be in the same position in your

Wil Schroter: role of day? It's funny, I, I noticed this for the first time when I shifted careers, you know, I'd started an ad agency and then we sold the ad agency. And up until the time that we were running the ad agency, I had a huge circle of friends that were essentially clients and employees. And this is essentially all, you know, an agency is you people, you hire people you're trying to get money from and I had what I would consider to be good relationships with them. Right. But the moment that we sold the agency, like the day I was not there anymore. I had nothing in common with any of these people. By the way, we've talked about this too. When people sell their businesses, they totally forget how much of their social network and by way, that value and, and and whatever is tied to their jobs. Right. In the relevance in this case, when we sold the agency, I was like, damn, this is like 500 people that I was contacting in contact with on a monthly basis that I have nothing to do with. It. It was really bizarre. It makes you question, like, what were those relationships? Really? But what is every relationship? Really? Right. Like when Jason Barker lived down the street from me when I was eight years old, it wasn't that he was the best person I ever found. It's because he lived three doors down from me. That's how I knew you were. Like, everybody has a context for, for why, you know them.

Ryan Rutan: Exactly. Yeah. And then when that context changes, everything changes. Right. And I think it's interesting because it's so abrupt in this case. Right. Whereas with, with Jason Barker you probably, you know, you stayed friends and maybe you went to different middle schools or something, you started to drift apart. You, you end up in a different town. Maybe there was, you know, well, you know, back in what was the eighties? So we would have maybe written a letter something or asked mom if you could find the number and call them whatever. Right. But there was this sort of gradual and that was one person, right. There were very few situations where all of a sudden you go with this very binary switch is flipped. Where your relevancy to those particular people change like that and you lose a lot of relationships all at once. And I think that's, that's a big part of it. That's probably a big part of the reason why people want to jump back in. Right.

Wil Schroter: Yeah. But that's my point. Like, I think when folks make this leap, when they, when they kind of opt out of the game for whatever reason, good reasons or bad reasons actually doesn't matter. They don't necessarily appreciate what they're giving up. Now, if you're out for a month, probably won't lose much, right? Depending on if you switch industries or something, probably won't lose much. But you really have to say, you know, there actually is a cost to me being out of the game too long, right? All the stuff that made me valuable to the market, you know, not as to the market are wearing off. All my relationships are also other things like networking, contacts. I have clients that I have reputation in the market. Right. Ryan, you and I are out there every day right now in the start up industry, right? We're not the most popular people in the world, but we're well known enough, right? If we go hiatus for two years, there will be plenty of people to replace us, right? And that's who people will be talking about. That is the relationship capital that dwindles way faster than people realize. I think also if we hang back too long. We just sit at home. Right. We kind of start to lose our minds so we lose relevance. We lose relationships, but we also start to lose our minds and, and here's what I'll tell you whenever I'm, I talk to a founder, friend of mine, usually one that's exited. So they have a little bit of a means to be on, on their own for a while. They almost invariably go crazy and you almost have to. It's almost like there's no other version right in the start up business. What's kind of interesting about it is, it's not like everyone retires at 65 and you've lived enough life that you don't want to do that anymore. You know, you're at all different ages, ages that are way too premature to be done with life and on the golf for the rest of your life. Right. And so I'll sit down with the founder a month after she's exited her business. Right. And we'll have a great conversation. She's so enthusiastic, so glad it's done, you know, big sigh of relief. Then we'll meet up again a year from now. Right. And like, she's not that relevant anymore. She's like a little lost her shit a little bit. She's talking about like crazy ideas that have like, no basis anymore. And it just reminds me of like the crazy hermit that's like up on a hill somewhere living by themselves. You start to lose your mind when you are not constantly challenged by people in process, in customer challenges. Like this is what keeps us fresh mentally. You take that all out and say, oh, just sit in a room by yourself. Let's see how it goes. It doesn't end well.

Ryan Rutan: Yeah, COVID showed us exactly how well it goes. There's a lot of, there's a lot of parallels there in reality because I think one of the fallacies here, one of the, the misconceptions is that this is by choice, right? We're out by choice, we're out by choice. But all of the, the circumstantial stuff, all of the consequences of being out for too long aren't our choice? We don't get to decide whether we stay relevant. If we, if we don't do something to stay relevant, we lose relevance. If we don't do something to stay within the community and maintain those relationships, we lose those relationships. If we don't apply our minds and do something with those, we lose our minds right? In the same way that COVID was foisted upon us and we were forced into this, this isolation, your choice to be out of the game again, doesn't it? It's your choice. You could choose to come back in whatever. But if you choose to stay out, then you have to accept the consequences that come with that. And I think that's part of the problem is that founders don't see they're like, well, I, no, no I'm in control of this situation, bullshit. No more than you were in control of coding. Like, well, I choose which room to sit in by myself. Cool. Let me know how that goes.

Wil Schroter: Well, and that's the thing like you and I will challenge each other all throughout the day, not even deliberately, just by virtue of having a conversation, right? Like when I present something to you, I have to think it through. I have to, you know, make sure it's, it's co et cetera, usually not. But I try when I tweet something, I would, I, I gotta make sure it's, it's on brand. When I create some product development, I gotta think about what will work great for our customers. I gotta stay sharp because I'm constantly being challenged the moment you take that off there. And I'm like, man, I really got to hang those drapes, right.

Ryan Rutan: Where should I hang them? Fester my cat. Right.

Wil Schroter: Exactly. Exactly. Or I really gotta plan this ski trip. Like the, not the same thing, right? Like you lose your ability to basically exercise in a way that's so valuable that we get probably way too much exercise just by showing up in this business right now, you know, in a form of stress and anxiety. But again, a break is good. But once that break starts to, to run a bit and, and all of a sudden that break turns into I'm that old guy that used to do something that people kind of can't remember. Right. I'll give you a bad example because, because I don't wanna pick on him because I actually really respect him. But do you know who Steve case is? The fact that I have to ask? It's probably right for those of you that don't know. Which is why I think this, this is a, um, a great example, Steve case founded AOL. Co-founded AOL, right? Which are those of you that don't know what that is. It was the internet before the internet. He's had an incredible career. Oddly, one of the most connected people in tech, I still, you haven't seen but AOL was like, dude, iii, I can't even posted it at least 20 years ago. It still exists as a domain and, you know, in, in a business in certain respects. But Steve's been out there for a long time to his credit. He's been doing amazing things for entrepreneurs, right? But if we were to say, hey, Steve, let's suit up and build it again, Steve has been so far removed from what it, what it would mean to be, you know, in the weeds doing it. I'll never forget this moment toward the end of us before we sold. The, the, the agency agency was getting pretty big and we were planning on going IP O with the agency and we had brought in this super top level exec I told you about this before from Chase Bank. Uh it was called Bank One before Chase bought it and he had 50,000 employees and he would tend his fingers when he talked. He looked like if mckenzie could do a creative character, he had like the perfectly black and white hair, like styled back, like he looked like a caricature of a management consultant um from the nineties, right? It was awesome. And you know what good for him like that. That's actually not enough. It's not a bad place to be. But I remember he came in, coming from a 50,000 person company at the time we had like maybe 700 people in the what he was saying, I'm used to, right? He was like, well, I'm used to having 4 to 6 weeks of vacation. Like, bro, we don't take vacation, right? He's like, you know who's bringing me my coffee? Like, bro, you make your own coffee? Like what

Ryan Rutan: time will the driver collect me?

Wil Schroter: Yeah, exactly. Exactly. I remember in our first board meeting, I'll never, I'll never, never forget this. We sat down, he tempted his fingers. I, I didn't know that was really a thing. I thought that was like something The Simpsons did as a parody. He actually tempted his fingers and he said to begin, I want you to learn the 10 rules of Ken. I'm not even kidding. I, it is like something out of a comedy, right? He literally had written now the 10 rules of K, like Bill of Rights or something and how you, how you should interact with them. So we knew that was gonna work really well. Surprising he got fired. But nonetheless, when people come from a different world where they're not used to being in, you know, in the shit, like we are, it's hard to make that transition

Ryan Rutan: and, and it's easy to fall into that. Right. Like, you know, we're flexible

Wil Schroter: people. His life was

Ryan Rutan: way better before. Exactly. That's the thing. Like it was, it was different now. He didn't have everything that we have as founders doesn't have the flexibility doesn't have, there's a lot of things, right? But he also, you know, he also, you know, had his 4 to 6 weeks of vacation and somebody bring him c doing all these other things. There's, there are benefits to all of them, right? And I think this is an important part of the discovery is what do I actually want, but be very honest with yourself, right. We talked about this too, like play test some of these cons steps to or like, I just want to be off forever maybe. Yeah. But let's like, since you've never been off for more than four days and starting your start up, why don't we start with a week and see how that goes before we declare that we want this to be forever, right? So it is tough. But yeah, I think the, the longer you're out, the more likely you are one. And again, like if you truly are comfortable and you're enjoying and you're stimulated, you have all the things. Cool. Stay right there. But I just, I know far too many founders who have exited business gone and done something else. Either. Done, nothing done, corporate, done, whatever done, philanthropy, you know, built some organizations gone and, you know, built homes somewhere in Central America, whatever at some point they come back and they're like, that was good and that was healthy and I needed some decompression, but I didn't need full release from everything forever. There's a big difference between decompressing something and releasing it all out into the wild world. Then it just becomes meaningless and shapeless and formless, right? Which is what you and I both know plenty of shapeless, formless founders who are now running around trying to figure out how do I pull this back together? How do I become relevant again? Where does the gravity come from?

Wil Schroter: Yeah. Yeah. And look just to be clear, we're not saying that don't take a break or you know, be able to exit or wind down isn't an important. Yeah, please take a break. All we're saying is when you start that vacation, when you're like, man, I wanna be here from the stress, the anxiety and who doesn't, by the way and who doesn't when you're saying I wanna be away from all that just start to put a little timer in the back of your mind where you start to say, yeah, but I want to take some time off, but not too much time. I wanna get pulled out of the game so I can reset and, and reload, but I don't want to get pulled back into it 20 years from now when I'm a little too old to play. So I think what all we're focused on isn't, don't get out of the game. It's don't stay out of the game any longer than you have to because it is a bear to get back into it. So, in addition to all the stuff related to founder groups, you've also got full access to everything on start ups dot com. That includes all of our education tracks, which will be funding customer acquisition, even how to manage your monthly finances. They're so, so much stuff in there. All of our software including Biz plan for putting together detailed business plans and financials launch rock for attracting early customers and of course, fundable for attracting investment capital. When you log into the start ups dot com site, you'll find all of these resources available.

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