Startup Therapy Podcast

Episode #36

Ryan Rutan: as a founder, do you find yourself feeling isolated, anxious or alone? We've all heard the phrase, it's lonely at the top, but as founders, we do far more than hear it. We live it on today's episode of the startup therapy podcast. We're going to talk about why loneliness is part of the founder journey and what we can do to minimize the negative impacts it has on our lives, our families and our startups. Welcome back to another episode of the startup therapy podcast. This is Ryan return from startups dot com, joined as ever by Wil Schroder Ceo of startups dot com. Speaking of which will, since we're talking about about being lonely and and we've all heard that phrase, it's it's lonely at the top. You've been a Ceo for more than half your life now. And and so I would imagine that this, this was something that kind of kicked off pretty early in your career and getting used to being alone at the lunch table.

Wil Schroter: Yeah. Even if you're surrounded

Ryan Rutan: by people,

Wil Schroter: you mentioned the lunch table that I think about it, I became a ceo at 19, which means 18 months prior, I actually was at a lunch table like in high school. So not a lot of time to ramp up into this uh, into this job, but here's what was really interesting about that this concept of being alone, but also understanding what it means to be a Ceo because before we get into it, I've got to point out when you become a founder, you often become a Ceo and people don't realize that a Ceo is often a title that you grow into over a very long period of time and it requires bestow it on

Ryan Rutan: yourself. Exactly.

Wil Schroter: Or you can, you can file an LC and B1 today and so we're in this weird business where we can sort of jump the line overnight. And with it we get all of the responsibility that comes with that job without any of the experience that comes with that job. As a, as a founder. It's more so if you grow into a ceo job at almost any company, you get the job, but you often get a tremendous amount of infrastructure that comes with that job. You know, you may have a CFO or C T O, et cetera in a startup. You get the job, the responsibilities and none of the infrastructure, no support whatsoever and not a lot of time to think about what is this job? You just, you want to build a company and all of a sudden you're like, man, I have a lot of responsibilities that I didn't even contemplate a minute ago. one of the things that they don't put in the brochure for this whole ceo job is how lonely it is. And one of the things we don't talk about very often as founders is how lonely this journey is and I don't think people understand why it's so lonely or often I don't think they understand that it's lonely. In other words, you're you can feel it, you can sense it, you can tell something's off, but you you can't put your finger on it, you know what I mean?

Ryan Rutan: Yeah, you don't come to the realization that it's loneliness that you're suffering from right. You you feel off, you may, you know, something's wrong, you're just not sure exactly what it is. And of course it's not the only thing, right? It's not the only potential negative factor when you're founding a company. And so it can happen in conjunction, in fact, as we'll talk about it, it's often caused by some of the other things that happen as you start to grow into your into your new role. But yeah, it's it's a very lonely journey

Wil Schroter: and it only gets worse. I hate to say that because that sounds like such a dramatic prescription, but it kind of happens and I'll give you an example. So I started the company, I'm 19 years old. And what are the weird things about starting a company when you're 19 you're not older than anybody, You almost can't be. So anybody

Ryan Rutan: that only legally employed people maximum one year younger than you? Exactly.

Wil Schroter: So almost anybody you would hire would be older than you and the reason I bring that up is because when I'm getting started in my career Ah and I'm 19, I've never been a ceo before. I don't know what that means. The last job I had prior to that, I was making sandwiches. Not exactly a prep job and I'm at lunch with my coworkers. And I'm kind of just bitching about how things are going at the company. And mind you, that's what people do at lunch. They bitch about their jobs. They bit about the company. It's it's all well and good to some extent. But what I didn't realize is everyone else around the table complaining about something is one thing, the moment I complain about it, it's very

Ryan Rutan: different, very different context when the ceo is complaining

Wil Schroter: and I didn't know I did not know that. I wasn't I wasn't allowed to do that. And let's face it, how could I I had no context for this

Ryan Rutan: Job on page 64 of the Handbook will

Wil Schroter: I wish. And so what happens is I'm at lunch and uh where the company is growing and I may say something like, well man, we really don't have much money left in the bank the moment you say that In front of your coworkers. And and look, I'm being honest, I'm being transparent, you know, we're talking about the state of the company. I'm mentioning something that's 100% true. I'm just not supposed to say it.

Ryan Rutan: I can hear, I can hear the chewing stopped. Right. It's just it's now dead silence

Wil Schroter: everything. Huh? You said, what did he what? Right. I I picture this snl skit in my mind and it's this founder who has no idea what he or she is not supposed to say in front of their employees and they're just sitting there going on over lunch break. I don't know. This company's gonna make it to the end of the year. I mean, my wife wants me to do pretty much anything else. You know, I've been updating my linkedin, I've been kind of looking for jobs. Uh, you know, this thing might work, but who knows? I don't have any idea what the investors are going to say,

Ryan Rutan: What the engagement goes to. zero confidence goes to zero. Yeah,

Wil Schroter: I'm not qualified for this job. I don't know why anybody would have me do it. I mean like the whole thing, right? Once you learn that lesson, once you step over that line and realize that there's a lot I can't share as the Ceo of the company and as that you're the founder and even the management team, you know, it's not exclusive to the Ceo, but once you realize that there's a lot, you can't say that sure does limit who you can say anything to ever. And all of a sudden things start to get a little bit more lonely.

Ryan Rutan: Yeah. And again, like you're sitting in a group of people and you're still lonely, right? Because you can't share to the same degree that they can, you can't participate in the same types of discussions that they can, so you may be surrounded by people and still feel completely isolated.

Wil Schroter: And let me build on that, it starts to escalate in all of these other areas. So I'm at a party with friends, but one of my friends that I'm talking to also his best friends with, one of the people that works at the company, I can't say a whole bunch of stuff, right? And look, man, the ceo, the management team, we go home with the same problems. Everyone else does the differences. When we complain about them, it's under a microscope and

Ryan Rutan: everything gets interpreted and reinterpreted and reinterpreted and, and then it turns into the telephone game and yeah, it's happened before. Then, like by the time I've said something that comes back to me, I'm like, well, it wasn't exactly great news when I send it out. But now that it came back to me, it's far worse. It's not at all.

Wil Schroter: Yeah, absolutely. And here's the thing, if you're a first time founder, especially a first time founder, and it's not exclusive. But if you're a second time founder, you've probably been around the block, you get this one. If you're a first time founder and you're trying to get a sense for how do I continue to build the community? My company and stay connected. Everybody. But over time, things are starting to feel off in some way. This is why it's happening at some point, you're not appear, you're everyone's boss and when you become the boss, the Delta's begins to grow when that delta begins to grow, you start to feel alone, you start to feel alone at work. And I think we should also talk about how you start to feel alone in the other parts of your life, but particular to work, if you're starting to feel those pangs of, I'm not getting invited to lunch with the with the guys or girls or whomever as much as I used to. It's kind of a reason.

Ryan Rutan: Yeah, yeah. That one was particularly tough for me because as I was starting my company in 19 I made one of the classic founder decisions to hire a bunch of people already knew, right? I hired friends, some of them very close friends. And so as that gap started to these were people that I was already really, really familiar with intimate with in some case like the really good friends and so I was used to being able to share anything and everything and I watched the downside of that. I watched the negative side of that play out and you know, the other thing that became really challenging for me was that it was, it was still, I still had to be the open door and I still had to listen to their complaints coming uphill, right? But I couldn't then share back down. So in addition to having my own weight that I couldn't let go of, I'm now taking on their weight, their challenges, their problems and both inside and outside work, right? And it got to the point where I didn't feel like I could share anything with them anymore, which is which is really a pity because the the outside of work relationships, they're just always seemed to be just enough tie in. Like there was always just enough connectivity between life and work, especially at that time we were just working like crazy That you couldn't separate the two clearly enough to be able to say, Okay now it's friend time, let's go be friends now we're back in the office to the office time and especially with the maturity of a 19 year old wasn't going over well, right? So it was particularly painful in that case

Wil Schroter: it goes both ways for the person that becomes your employee, especially if they're your friend, they can't complain with the same agency as they can to their other friends because at the end of the day you write their paycheck. And so they're thinking in the back of my head, the back of their head, what can I can I say to Ryan? Not all of them thought that way, that's for sure. There were

Ryan Rutan: a few that were like, yeah, no, no anytime I need to talk to you about something about something like this, it's it's just friend time now let's let me, in fact there was one that used to literally say that every time he's like, can we just talk as friends, it's fair and then he'd ask me something about it. Yeah, it is fair, except that he'd ask me something about his paycheck and I'm like, well hang on a second,

Wil Schroter: can

Ryan Rutan: we just talk as friends? You need to pay me more like, hang on, No, that's not how this works.

Wil Schroter: Well look, man, uh, your coworkers are just one piece of it and your mileage will vary over time asset to how that separates. It's, it's almost safe to say it will separate. I'm sure there are examples of other founders, you know, that are on the startups dot com platform that have a different story and I hope they do, you know where they're saying actually, I'm really close friends with everybody and and we don't have that issue. So that part of it, what we're describing isn't a, it's absolutely gonna happen in the worst possible way. There there are some methods, I'm sure folks are managing it. I'm just saying is if you're starting to feel some sort of distance etcetera, there's a reason this is how these things developed, but that's, that's not where it ends. There are lots of other parts of your life that you start to see the distance get created and in the one Ryan, I think it's worth us talking about is friends, family, spouses. In some cases, you know, we're more and more time goes by, you're trying to explain to them what it is that you're doing, which doesn't make any rational sense because all they keep hearing is I'm losing lots of money. I'm stressed out. This thing may not work, et cetera. And they're looking at any rational person would be like, right, you're an idiot,

Ryan Rutan: right? It is Now the time that I tell you, I told you so like what do you want to hear from me?

Wil Schroter: Or or like, hey, let me try to save you. It looks like things are going really poorly, which they are until they're not, this whole business is about running into the abyss and everything going to hell until one day it's just going to hell less and then eventually, hopefully it's less chaotic. You know, it's, it's it's what

Ryan Rutan: was the line from Shawshank Redemption Andy crawled through a mile of ship and came out smelling like roses, right? Like that's it, right? We crawled through that mile of shit

Wil Schroter: and then at some point,

Ryan Rutan: hopefully, hopefully we come out smelling like roses, right? But there's, there's a fair amount of ship to wade through

Wil Schroter: Ryan. I'm sure you remember when you were starting your first business or hell even, you know when we were launching um startups dot com. Yeah. Trying to explain what we were doing or trying to explain the state of the state when none of it to a rational person would make any sense.

Ryan Rutan: Yeah, it's always so difficult and for a lot of reasons, right? Again to rational person, that wouldn't make any sense. Even the parts that, that would make rational sense. I think part of what happens to us is, again, we get used to being lonely. And in fact, I think like more experienced founders may suffer from this even more because they sort of, no, that's the route, right? Like you're just gonna have to internalize a lot of this stuff, you're not going to have appear or a teammate that you can go to with a lot of this. So we spend a lot of time inside our own heads and when you start to spend a lot of time inside your own head, things start to make sense to you at a different level, right? I've been thinking about this thing for three weeks and I'm gonna try to explain it to you in three sentences, usually goes over really poorly.

Wil Schroter: Yeah. If you, if you're not in a world where you have, let's say other founders around you or at least people that understand the journey, it's so hard to feel connected in the same way. I mean when I was first starting No one my age was starting a company period. So I remember I was 19, I was a 19 year old college student. And so I'm at a bar that night after I've been working all day and I'm talking to my peers, 1920 year old peers about starting a company and how I'm trying to figure out how taxes work and what's going through their head. They're not like, oh man, I'm dealing with the same thing. I mean like these corporate tax rates are insane, right? Not the conversation I'm having having and I can picture lots and lots and lots of other folks to become founders that turned to their pure network, which is normally really supportive when they understand what you're going through. You know, when you see moms that are talking to other moms and they're talking to bitching about the kids, you know, these kids are all crazy, etcetera, any other moms all understand, right? It's high fives and commiseration and it's a ton of empathy. But then you raise your hand and you start talking about something that's so far outside of everyone's wheelhouse that no one wants to talk to you about it because they have no way to carry that conversation.

Ryan Rutan: There's no context, there's no level of interest. There's, there's just nothing right there. Just the best they can kind of be an empty ear that you can fill with words that they don't understand. Not very

Wil Schroter: helpful. I've seen this in different scenarios and I'm just trying to kind of paint a bigger picture here outside of just founders. I've seen it when I know I talked to combat vets who are talking about what they've gone through in combat a buddy of mine is a navy seal and he comes back off rotation from time to time and he and I get together and he's telling me what they're going through the parts that he can actually reveal. And, and I try relatable in

Ryan Rutan: so many ways.

Wil Schroter: I try so hard to like connect with him on what he's doing because it's fascinating to me. But even even the fact that it's fascinating, he's talking about the drills they're doing in some cases, the parts he can disclose, he's talking about the missions he's going on and I'm trying to like make a connection. I'm like, oh man, I hear what you're saying, you know, that must have been an incredible, you know, incredible journey. I had the same thing happened when we were on a trip to europe and we got lost

Ryan Rutan: drawing some real strong parallels between this time I got a blister while hiking and that where you were, you know, field dressing that, that, that flesh wound that was so, so similar or my

Wil Schroter: favorite now is as I've gotten older, Sarah and I will be on a double date with a younger couple that doesn't have kids and inevitably we'll start talking about kids stuff and I just watched their eyes glaze over and the best part about it is we're having this conversation into their credit. They're really trying to connect with us and they'll say something to the effect of, oh yeah, my parents did the same thing when I was a kid.

Ryan Rutan: Yeah, that's, that's the best they can do. Let me go back to when I was an infant and pull from that vast experiential.

Wil Schroter: Yeah. So a bit of a detour. But my, my point being, founders have this same issue when, when you're trying to talk to you to what used to be your peers about the stuff you're dealing with and they just have no idea. You know, you're trying to raise capital and they understand money, but they don't understand raising capital.

Ryan Rutan: No, no, they don't.

Wil Schroter: And so this loneliness comes from the folks at work, your, your peers sort of speak at work. And that, that's weird because it, it grows, it doesn't usually get better. It comes from your peers and your social circle. And then the other place I'm going to point out your spouse if you have one, Yeah. Coming home consistently late hours, all kinds of financial problems and try and explain to them that, you know, this is something that's important to you and like they get it, but they don't always get it right. It's, it's like when my buddy, the navy seal tells me what he's doing and I understand what he's saying, but I don't get, it was shot at earlier last week. Like we're not on the same page.

Ryan Rutan: Yeah. And that, that can lead to a huge disconnect and and like that again, like that is an isolating factor, right for for us as the founder when we can sort of see, and we know right, here's this person that were, you know, very intimate with trying to share this experience that we're going through because we need to tell somebody right. At least here's somebody that sort of has to listen to us. We take the the available ear and twist as much as we can. But you, you know, that you're not really getting through at the level that you need or want to. Uh, and that can be hugely frustrating. I know in my own case what it typically leads to is I'll do it for a little while and then I'll just stop doing it right. Just go back to the good old bottle it up and keep it inside routine, which always ends well. It always ends well. Yeah. Just keep it really deep. And and so and then that that's cyclical for me, right? And then at some point I'll get to that tipping point again, I'm like, I got it. Yeah. Talk to somebody gotta tell somebody. So even though I know I'm not going to get the same level of understanding that maybe I want or need, I'm going to go back to that. Well, just because it's what I have available, right? And again, just that action alone can make you feel more isolated knowing that you're going to now go do something is the best option you have, but it's not a good option never feels great,

Wil Schroter: It doesn't. And I said earlier and I feel kind of dark saying this, but people ask, will it get less lonely at some point? And, and Ryan, I don't know if I'm overstating this. I don't think it does. You know, I'm just saying like, like at current pace with, with your, your staff, with your peer group, with your relationship. Again, if you have a spouse, whatever you have, I haven't seen a lot of cases among myself or other founders where it got less lonely. I'll give some exceptions because again, I don't want to make it all doom and gloom here and there and there are ways to address this, which, you know, will definitely get into that big party. But you know, I'll use myself, my wife Sarah, she's done a handful of startups as an employee, not as a founder. So she understands the business a bit. She and have been together a very long time. So she's, you know, she's seen this stuff firsthand and I would say she understands it, but she doesn't get it and read the book. Yeah, yeah. She hasn't lived it. And for her when I come home and she sees the frustration on my face or you know, sees the anxiety, et cetera, which is only every day. Um, like she, she sometimes sees it a little bit differently than than I'd like her to, and this is, this has nothing to do with like be pointing the finger at her, she's, she's doing the best she can with the information she has, it's a matter of, hey, I'm willing to run into the wall over and over because I believe so strongly in something unless you felt the same way about something and maybe, you know, she could draw the parallel to how she feels about her kids, etcetera. She doesn't see it exactly the same way. And so my loneliness, my ability to, you know, find a place where someone else understands what I'm going through and can kind of commiserate and help me get through it. It's gotten better over the years because we just got more reps. But I wouldn't say it's been 100% solved. And I'm not sure what what your mileage has been

Ryan Rutan: it's about the same, right? I think there there are sort of times when I know I can use that as an outlet and it'll be enough to kind of get me to where I need to be and I just need to vent a little bit. And sometimes when you need to vent, you don't really need any feedback, right? You don't need somebody to fix it for you. That's not what we're asking for. We're just asking for somebody other than the voice inside our head to hear what we're saying and not along and sometimes that's enough, right? And other times, you know, and like you said, the mileage varies and I would say that's you know, even within a relationship, that the same thing happens one time it may be, you know, just sort of the commiseration, like just kind of nod along other times, you know, she's come, she's come back with some really insightful things based on listening to what I was saying, because she had a very different perspective, right? Because she didn't get it in the same way I did, she didn't see it in the same way that I did and actually came back with some things that were quite helpful um and then end up being quite cathartic. Um so there's, there's always that chance to write, I wouldn't say that's been the norm, but it has happened um and I remember like being really pleased when it did, and that's again, it's another one of those reasons that you continue trying to continue trying to open that communication line and keep it flowing, but mileage varies

Wil Schroter: about a year ago, I'm having dinner with the founder buddy of mine, it actually built a pretty incredible company and we're having drinks, just kind of like unwinding a bit and we start talking about just some of the frustrations he's having at work and what he's dealing with and kind of, you know how he's dealing with it personally and I started asking him very pointed questions, does it feel like right now you have these feelings, but there's no one you can actually talk to about it. He's like, you know, it kind of does. And I said does it feel like it's getting worse? And you could tell like he could he was feeling these things but nobody actually pointed them out. I started to say like, you know, kind of like a doctor going through like, you know, the full checkup, you know, are you feeling this? Does it hurt when you move this way? And you're like yeah, yeah. It does. It does. He's like and and so I just started to kind of like nudge a little bit, never push. But uh say is it the case that you feel like uh things like this? This weight is getting bigger and bigger on your shoulders yet you have fewer and fewer people that you can share it with. He's like yeah, that's exactly it. I was like, look a couple things, number one you're dealing with what we all deal with. He's like really this is the problem and this is why I hope folks that are listening to this, get this. If all of these things start to sound very familiar to you, it's not that they're great. It's that this is exactly how the process goes. It's shitty. Don't get me wrong, right? But if you're feeling these things, if you're feeling a bit lonely about boxed in a bit hard to communicate. This is what happens. This is part of the founder process. It breaks though when people don't understand that this isn't an anomaly right? This is actually part of how this this journey goes and don't understand what to do about it. You know what I

Ryan Rutan: mean? That's such a founder characteristic though, right? That the problem that we're going through, I must be the only idiot that's ever had this, because I'm not cut out for this job. And it's like no, literally everybody else did exactly the same thing. And I think that's even more of a problem when we're talking about something like loneliness, because by virtue of just what loneliness is, it means you're experiencing and by yourself, right? Uh and so therefore it can feel like it? And it is right, we all experienced this differently, right? Like loneliness means different things to people. And it's something that you go through individually, just by definition, and I think that can make it hard to understand in the context of somebody else's situation, right? You may see somebody else that you think is lonely. You don't know why you don't know exactly what that means or how that impacts them. I think that that tends to kind of double the pain of being lonely as a founder,

Wil Schroter: you know? So I'm sitting across from that same founder and I'm going through kind of this progression. Do you feel this? Do you feel this? Do you feel this? And I already know the answer is I just need him to hear them say them. and and I said, do you want to know what the answer is? He's like, God, yes. I said it's just talking about it, it's just finding another founder to sit across from and have exactly this conversation and Ryan, I think if we're going to talk about this feeling of loneliness and I'm not saying finding a founder is the only way to solve it. I'm not saying that people solve it in tons of other ways. Yeah, but but I think it's worth talking about this one because it works pretty damn well.

Ryan Rutan: It does, it does right? Because again, it's it's the recreation of appear somebody who can hear what you're saying and understand it. Um and and truly empathize, right? Not just sympathize what you're doing, which would you get from everybody else, but to really take an empathetic perspective and understand what you're feeling and probably just share some of the same stuff, right? And that's that's what's been really interesting as I've gone through these situations myself, I've often found catharsis and just knowing that they were going through it too. It's not like we were like, oh and how do we solve it? And then we came up with the answer and then walked away feeling satisfied. Like no, just by virtue of knowing that I wasn't the only one going through this. Um and that you can just keep going and it'll be okay, that was enough, right? Which was, it's pretty amazing.

Wil Schroter: I agree. And here's this really interesting thing that happens the moment you give permission to unload all of this

Ryan Rutan: stuff. It

Wil Schroter: comes out like a fire

Ryan Rutan: hose. Right? So make sure that you open that valve and step to the side of media.

Wil Schroter: Uh, so I watched this happen in another capacity, you know, Ryan, as you know, we've done Founder dinners all around the country for 20 years and the setup is always the same. It's always roughly 15 founders, uh, typically founders who have never met each other before, but that's not necessarily the prescription that just often happens. And it's a single conversation. Often we do it in my living room. I, I invite 15 founders over. I've got one in a couple of weeks. In fact, Invite 15 founders over and we sit in a room usually in a circle. So it can be one conversation and we go around the room and we just, we say the same thing every time we've used the same formula forever, we don't say it's a formula. We don't make it a thing. Uh, we just say, hey, everybody, as we go around the room, uh, tell us what you're working on because people don't know each other. So it's some context. Uh, tell us what's your biggest challenge right now, which is usually implied a frustration and tell us how anybody in the room can help you, Right? So it's usually an ask, which creates value. What will happen is we kick off. Usually I'm moderating it, so to speak, so I'll throw it to the first person that I think will be fairly open. This amazing thing happens. The first person who kind of gets it and they'll just be a bit more open, says some really personal stuff right there. Like man, I'm actually in battling brutal depression right now. Uh you know, I'm seeing a therapist, uh my wife and I are going through couples therapy and everyone else is like, whoa, now, by the way, I'm seeing how amazing that is not depression, depression stuff, you know, couples therapy stuff, I'm not saying that

Ryan Rutan: I'm saying get off the chest

Wil Schroter: buddy. The moment one person sets the tone in the room that it's okay to talk about this stuff, the room explodes, it's unbelievable to watch every single time. I've never seen it not happen. Uh and we've been doing it for 20 years, in in in L. A. and San Francisco, you know, all these different places uh

Ryan Rutan: tells you a little bit about how much pressure is behind that valve. Oh

Wil Schroter: my God, man, but it's awesome. And within that the moment, 14 people here at the 15th person just unload and it's not always bad by the way, you know, sometimes they're talking about good things that happen to um everyone in the room was like, dude finally like I'm in a room full of people that understand

Ryan Rutan: what I'm going through. They get me,

Wil Schroter: Get me right? And, and it's not incidental. It's not like I just happened to have found 15 founders that all had the same types of problems on that particular night for 20 years. Right? I picked 15 random people. Like these are just happened to be founders. It's that the problem is so commonplace. So what I noticed was The moment we can sit two founders in a room and I'm talking about 15, but it could just be me and a buddy. The moment we sit 15 founders in a room and we let them just share, just unload everyone unloads and you hear the craziest stuff and I'm saying good, bad and different and all of a sudden you just feel like this huge weight collectively come off everybody's shoulders. The other cool thing. Not entirely related. There's nothing more awesome. Then putting a question to, hey, I need help with this. In seeing 14 people raise their hand to help you.

Ryan Rutan: Right. Right. I mean, yeah, knowing you've got some support there goes, goes a long, long time.

Wil Schroter: Pretty amazing. Ryan. It's just kind of turn it back to you. I'd like to believe that, you know, you and I have worked together for a long time. You mean the other partner Elliot, all founders, It's got to be somewhat helpful to you to be able to know that in working with founders, like they get you.

Ryan Rutan: Yeah, for sure. I mean like that's it's actually one of the beauties of of the business that we've built. Alright. Is that just by nature of our business, we've surrounded ourselves with other founders and so we're we're building a business that builds a business amongst our peers. Uh, and so there's there's been so many great relationships have come out of just by proxy of building this business. Right? So many other founders we have now, I had a decent founder network prior to us starting startups dot com, but it is like you wouldn't recognize it, it would look like some sort of a child's toy compared to the relationships that I have now with other founders. And I think that's a huge, huge piece of it. And so I, you know, as we get into like, what do we do? Right, how do we, how do we how do we solve these things? And I think that having that founder founder peer group is a huge piece of it, there are a lot of other things that I've done that have helped as well. But if I'm really honest, the Foundation for all of the other things came from having that founder peer group to begin with, right? Knowing that I had that release valve, knowing that I had access to people who truly got what I was going through Alright, both in you and Elliot as partners and in all these other amazing founders that we've we've met and become friends with through this and through other endeavors, it really opened up a space to be able to do some other things that I think help. And so, you know, I think we should spend a little time today talking about, you know, what can we do? Like what else can we do to take some pressure off? But again, I think in my case, if I'm really honest, there are some other things that we'll talk about that I've done but that having, you know that another founder, another group of founders that I know and and and if you know, if if you haven't developed this yet, anybody that's listening, I would urge you to I have no less than 15 people that I know I can send a founder bat signal out to who will pick up the phone immediately, no questions asked, I literally don't care what time of night it is and I do the same thing, right? I've I've been in, you know, interesting meetings, important conversations, I see a particular text indicating a situation from, you know, somebody within that really close peer group, I'm gonna do whatever I have to to extract myself in that situation so that I can answer that call right? And and it always feels so good to be able to answer that call and man when you're on the other side of that and you're dialing that and somebody answers, you know that it's email, text, phone, whatever you use to get in touch with that person and you get that nearly immediate response. Just that just that, just knowing like, okay, I'm not completely disconnected goes so so far, but so let's let's let's transition a little bit and let's talk about what else do we do? So the peer group obviously, you know, an amazing thing and I think it's absolutely necessary and again, I'll make the case that without that peer group, some of the other things that I'm going to talk about wouldn't have had the same impact that I needed that peer group first. But that that opened up some additional things that I do to stave off some of the loneliness of being a

Wil Schroter: founder such as what?

Ryan Rutan: So, you know, some of them are pretty funny. One of the ones that I found is this is counterintuitive, but fishing by myself, I used to go out in my mind and we lived in florida, I would paddle out and I would go to a place that was actually lonely, not lonely in a bad way, just lonely. I was out there by myself doing my thing under under circumstances that I had some control over the things I wanted to go and do. Um and it made me appreciate that I wasn't actually alone in a lot of these other situations, this is alone and this is not sort of draw that contrast also. And just generally speaking like that was such a cathartic thing for me and fishing was just that time away. Yeah, there was a lot of focus on the fishing, but it also freed up the mind from a lot of other things and just kind of gave me that space to be a little lonely. Right?

Wil Schroter: Well, I mean have some time alone but not lonely,

Ryan Rutan: right? And I think that was an important piece of it. Um some of the others were that rather than try to find peers that were all work related, which I think is is a bit of a trap and I think you do need some of those, but I think if you try to build everything around that right, if you expect everybody that you talk to at a at a meaningful level to have that same level of understanding, you know, basically just to be a founder. I think you missed out on a lot of other fun things in life one and I think that you missed out on a lot of other important perspectives. And so one of the things that I found was to work hard to build groups of peers in something that absolutely had nothing to do with work because you need that space too. Right? And and I know that we've we've we've worked hard to do some of these things even within the context of work, right? Like the, you know, the work cookouts, hockey, other things that we've done. You know, when we when we used to have are pretty aggressive NBA jam tournaments. Um There were a lot of things that, you know, were happening at work, but had absolutely nothing to do with work. Um And it gave, you know, that's actually a really interesting one. So if we if we kind of dig into that one, NBA Jam for anybody who is unaware, just turn this off. Now, I don't want you to listen to me anymore. Now, it's a video game, it's a two on two basketball game, right? And what did allow what it did was level the playing field, right? It gave us a little space within the office where we had the hierarchy all the way from, you know, and the most junior person in the office up to the Ceo had a chance. They didn't really, I mean, let's be honest, we we owned that machine, but you know, the the idea is there right? That you could be peers, right? They had a chance to hold something over us. They never really happened in reality, right? We know we want all the time, but they had the chance at least, Right? And I think that was that was an interesting dynamic where, you know, you could you could kind of everybody had this the same opportunity. Um And so I think creating things like that within work can can help write it, can help to take some of that pressure

Wil Schroter: off. You know, you said something that talking about like finding other outlets, etcetera and again, we're talking about loneliness, not just frustration, I mean frustration, you know, can have many variants but around loneliness. What I found and maybe folks that are listening are starting to see it in my first company was that because I was spending so many hours at the office, my my friend group was becoming everybody at the office and that was only compounding my problem of starting to get disconnected at a peer group because I was essentially losing my peers and I don't want to say that, but that's kind of what happens.

Ryan Rutan: No, it is. And then, and then those friendships that you develop at work when you are the one sitting at the top of the stack have an upper limit, right in terms of what that friendship can actually be, right? So you're you're automatically limiting yourself at that point and and leaving some of the conditions of loneliness wide open at that

Wil Schroter: point. And you know, so When I was started, the company was 19, the company had gotten pretty big by the time, I would say 25 at that point, I actually just took a hard right turn and said I'm going to make all of my relationships be the personal relationships, be outside of work. In fact, I took it a step further. I said I don't even want the people that I have outside of those relationships to know what I do. And so, so I made a a habit whenever I was around my circle of friends that I was building outside of work to never, ever, ever talk about what I do. In fact, I mean, it's a small enough town, it was big enough company that people knew I did something in the internet kind of thing. But short of that, you would have never heard it from me. I just didn't bring it up. And to this day I've maintained that same sort of different social network and I try to do as best I can to kind of keep them very separate. Um, and not in the overlap because there's some great people in both groups and they have a lot of commonalities, but I try to keep those two separate so that I can have a kind of a call it a safe space where I can just be a dude and hang out and talk about football and talk about whatever without having to constantly worry about what comes out of my mouth and how it might affect me on monday at the office.

Ryan Rutan: Yeah, Yeah, for sure. No, I think that's, I think that's really important. I've definitely done some of the same in terms of of the, the isolation of the groups. Um, and even to the extent that I wasn't as deliberate about it as you are, I didn't decide to do it, but I did find myself and in a couple of particular context, right? Like a developed a bunch of fishing buddies, right? And none of them were founders, right? Some of them were unemployed. Um and so it wasn't the kind of thing I want to talk about, like I wasn't there to talk about that and I were just talking about fishing. Uh same thing as I developed the redeveloped my my my love for playing soccer and got back into that same thing. I wasn't talking about work with them and quite intentionally, if they would ask me like what I do. Um you know, now, now that I'm here in Antigua, I just tell people, you know, we we, you know, we have a business up in the US and leave it at that, I don't say anything more about it and I'll see what my involvement is. I don't say, you know what kind of business it is, I just try to let that pass. Like I don't want to not answer the question, but I don't want to get into it and I don't want to answer more about it than that because I'm there for a different reason. I want to maintain that pure relationship and particularly here, you know, the minute you're something other than an hourly worker or you know, a lot of the guys I play with, they're just, they're they're day jobbers, their hourly workers, I don't want to change that relationship. I want them to feel that, that I'm appearing in a lot of case I'm a low man on the totem pole because they're younger and in better shape than I am. I don't want to make any excuses for me.

Wil Schroter: No, I agree. And look, man, um you know, if we look at this kind of at a high level view, at almost like a summary view, I guess um a couple of things become really obvious. We know that as part of this founder journey where you're all all of a sudden fast forwarded to the end of the line where you actually become ah ceo the next day that on that very day your life and your loneliness as it relates to work, the clock is ticking every day that goes by the delta between you and the folks that you work with begins to grow. And again, some people do a better or worse job managing that. But inherently all of a sudden these new dynamics start to show up. You know, you're, you've got relationships, but you also pay that person, you know that that gets a little bit funky, sometimes there's a lot of stuff that's on your mind that you cannot share. That's, that makes a tough peer relationship, right? Because you, you'd love to be able to go to lunch and complain about this stuff, but you cannot absolutely cannot in all of these dynamics that sometimes start to change a little bit faster than you might expect them to leads to a lot of loneliness.

Ryan Rutan: Yeah. And we know the best ways to address that loneliness are one to acknowledge it, recognize it for what it is. To drop the expectation that your current peer groups are likely to be able to understand what you're really going through at more than a superficial level, which leads to number three to develop that real peer group that will truly understand what you're going through. And lastly remember that solitude is part of this, but that loneliness is something you can push back against and maybe you won't eliminate it, but you can put it into the margins. That's a wrap for this episode of the startup therapy podcast. This is Ryan Rutan on behalf of my partner Wil Schroder and all the startups dot com. Family thanking you for joining us and we hope you'll continue to join us. Be sure to subscribe rate and comment on itunes or wherever you love to listen to startup therapy. You can find all of our episodes at startups dot com slash podcast. If you're looking for more amazing resources to launch or grow your startup, be sure to head to startups dot com and check out startups unlimited. It's everything we have to offer from our online university to our amazing community of experts and founders and even all the tools we've built like biz plan fungible and launch rock. It's everything a founder needs, visit startups dot com slash begin that startups dot com slash b e G i N. You'll thank me later.

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