Startup Therapy Podcast

Episode #78


Ryan Rutan: Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan joined as always by my partner will Schroeder founder and Ceo of startups dot com will Today, we're going to talk about something that I think most founders struggle with, which is this idea that you know, are we a separate entity from our startup? Is our startup a separate entity from us? What's your experience been, man? I I know for me it was it was harder in the beginning getting it easier now, but like what go back in time to like the first couple and take me through it,

Wil Schroter: you know, I think what happens is that we sort of get lulled into it because I think Ryan you and I have talked about this, I think that birthing a startup in many ways, feels like birthing a child. It's something you feel is so inherently tied to you and it is it's your creation and and that's wonderful. I think the problem is it kind of creeps up on you in that we start with this great idea and we start to develop it. We start to tell people about it, we start to get attached to it and we present it as ours, we don't just present it as a thing. We don't present it as a product when we go to work for a company. Like I used to work for this sandwich shop in Connecticut and I didn't go there saying these are my sandwiches, this is my idea was just like this is a crappy job where I have to make sandwiches,

Ryan Rutan: obviously wasn't a Subway then, because then you would have felt like a sandwich artist.

Wil Schroter: No, no, I was not a sandwich artist, but this is way better than Subway. Um, but regardless, like there was no ownership, there was no pride and therefore there was no attachment in quite the same way. What ended up happening is when I started my first company again, this came out of no work. So I had no context for it. People would ask me about it, and at first I was just talking about something I was doing. There was a bit of detachment, but remember over time I started talking about it as an extension of myself, and that's where all the problems began, right? That's where when it wasn't going well, it was no longer a problem at the company. It was a reflection of me, and it happened to be having working at the company and killed me. And I can't imagine your process was any different.

Ryan Rutan: No, no, it wasn't. It really wasn't at all. You know, the the the birthing, the startup analogy is is a good one. We've we've both birth. Well, we have not our wives plastic, we have done this for us. Yeah, they would dispute our our involvement in this. Um but we have been through the process of bringing a child into the world, bringing startups into the world. And it's it's a solid analogy because especially in the beginning, um their identities entirely wrapped up in you, there, there and yours in in in them, right? Like all of a sudden, you know, it goes from like uh you know, look at my my facebook feed back in time, like it was like I was at this cool place, I was at that cool place, I was at this sporting event, I was at that sporting event, pictures of my kids, picture of my kid, picture of my kid, picture of my kid, right? It just, it changes overnight, like all of a sudden it just becomes all about that um with good reason, right? And and startups are very, very much the same. Um there's an interesting period where I think, like it's super heightened, right? At the beginning, when it's just an idea, it literally doesn't exist outside of you. So how could you separate it when it's just an idea? And the only way that it manifests itself is when we talk about it to other people, that's the only time that it has any reality that exists outside of your own head, and I think that sets the stage for them, and that's a societal thing, right? Like we, you know, when actually I found out this isn't necessarily true globally, but in the US it's a really common question, so what do you do? Right, I'm an accountant? There's no follow up question to, I'm an accountant, right? Nobody gives a ship, but if you say, oh, I'm starting this company that does X, Y. Z. Sorry, accountants, and I don't mean to bash on you, it wasn't it wasn't me taking a shot at accountants that was just like people understand it, right? The same thing, if you say I'm, you know, I'm a family physician, right? They don't know everything you do, but they get a sense for it, you're like, yeah, you know, I'm I'm starting, I'm working on a financial mediation startup, like what the hell is that, right? Like what does it do? Like, and then you start to explain it, right? You start to explain the why you're doing it and and all of these things really everything that you're explaining that early stage is some reflection of you, right? Because there's a reason that you started this business, there's a reason you decided this was what you wanted to chase down. There's a reason you're spending your energy on it. Um and then I think there's this little period, you know, as things start to gain some traction where that potentially could fade away a little bit as things start to happen, and it isn't just in your head and it is existent in the world. Um but I don't think most of us recognize that at an early stage and and do anything about it, we we just still continue to think of it as as, you know, it's a direct reflection of me, you know, in the same way like we go back to the kids analogy, right? So when you're old and the sweet baby and it's just smiling. It's a wonderful reflection of what a wonderful parent you are. And everybody looks at you and sort of nods and smiles when you've got the kid who's screaming and throwing jars of jelly across the aisles in the store. Also wrote a reflection on your right. And there are plenty of analogs between, Uh, you know, broken jars of jam and and and startup companies, right? Does't always go well. In fact, like you said, 99% of the time it's not going well. And and and that reflects or we allow it to reflect on us as founders.

Wil Schroter: Well, I think that's the problem though, because we're talking about being attached to the startup from the very beginning. What we don't talk about is what the cost of that attachment is invariably going to be. And here's the problem. Nothing goes well. It cracks me up because when people start companies, mind you, they've never done it before. So none of us have any idea what we're getting into or what's about to happen. At least when we take a job, somebody probably did that job before us and will likely do it after us. There's a set of parameters. Everybody kind of knows what they're supposed to be doing in this case as we describe your running into the abyss. So every single thing we're about to do, we're likely going to do wrong because it's never been done right yet. And yet. And yet all of us as founders, rightfully so, because we're perennial optimists, we all believe that our startup should just be going right all the time. The hires should have been right. Our market fit should have been right, our marketing should have been right. Everything should have been right when in fact it's impossible, Right, right.

Ryan Rutan: You're lucky if one of those things is going half right,

Wil Schroter: correct. And so, but but that's where it breaks. And I think that's that's the inflection point that none of us are aware of until it actually happens. And I bet there's some folks listening right now, kind of shaking their head a little bit. You know what? Now that you mentioned, that it did sound awesome and it was great and positive to be attached to it in the early stages when nothing was broken. Yet, it became exponentially harder when things started to break. And that was attached to me. Let me let me say that just a little bit differently for a second. If everything in your startup was just gonna always go right, by all means, attach yourself to your startup. Yeah, that's fantastic.

Ryan Rutan: But we join the

Wil Schroter: Problem is 99% of the time, that's not what's happening, 99% of the time, shit's gone bad and when sh it's gone bad and our entire ego and persona and sense of self worth is attached to that, that cart we're in a lot of trouble.

Ryan Rutan: Yeah. You know, the other thing, it just occurred to me, you know, going back to that stage where it really does only exist in your head, right? Nothing really goes wrong, right? You may have some doubts or some questions, but like, it's all just fun and theory at that point, right? And of course it feels good. And so there's there's probably, you know, a a dose of of dopamine that we get from just going through that repeatedly explaining it to people telling them how awesome it's gonna be getting all amped up about it, which of course we have to do. But I think the, the extent the depth to which we buy into that as founders is part of what sets us up for the fall when invariably things become real and do start to go wrong, right? It's like, go back to the kids analogy, right? We're pregnant, people are giving us gifts. Everybody's high fiving me. I'm decorating a nursery. This is wonderful. Fast forward a couple of months. This thing just shipped on me. I don't know when to feed it. It won't stop crying, right? It's no longer as much fun all the time, Right? So we we have to be careful how we set ourselves up for this. And I think particularly for first time founders, it's really important to remember, uh, it's, it's kind of like, and I talked to people when they're about to graduate college about this all the time and they're like, you know, all these, all this stuff's happening, I'm about to complete university, that's going to be awesome. And like you realize this is when work starts right? Like it's, you know, you don't realize it yet, but this was a relatively easy period in your life. You may have worked hard during university, but like, this is still the theoretical period from this point forward, there's gonna be some work involved, right? And it's not always going to be fun and awesome. Um, not to, you know, dissuade them or turn down their enthusiasm, but to meet her, it a little bit, you know, with some reality, which as founders, we don't get right, you know, you were talking before about, you know, if it's something that's been done 100,000 times before, there's a pattern to follow, right? And you and I both do other things in our lives that are outside of, you know, the work we do in startups, um, that, you know, some of its creative, but a lot of it is still like, it follows patterns, right? You do carpentry. I'm a fisherman, right? These are both things, yes, they require skill, but there are also a lot of other skilled people doing exactly the same thing that we can pattern after that we can watch that we can sort of, you know, trail into the same thing with people exiting university. The problem for young founders or new founders, whether you're young or old is that you don't necessarily have that pier and that leadership and you don't have anybody to tell you, hey, don't get yourself completely wrapped up in this thing, don't let this thing become, you don't become this thing. And I think that that's a huge failure just in the community in general, not to help people have a better perspective on this from that early stage.

Wil Schroter: I think it breaks in a few ways to because, okay, I think we've established the fact that attaching yourself to a startup is a, is like chaining yourself to a sinking ship and wondering why you're drowning, right?

Ryan Rutan: There's there's this wasn't how it was supposed to work,

Wil Schroter: but but but but let me step back for a second and say there's also a separation between who we are as people and you just touched on this a second ago and the work we perform.

Ryan Rutan: Exactly, But

Wil Schroter: you said something interesting. I didn't think about it until you just said it. You said that, um, you know, early in our careers, let's say we weren't, let's say fathers yet at that time, our work was kind of the only thing that we were doing, you know, I think parenthood was, was interesting for me and I think I'm speaking for you in that it gave us something else to be that was more important for the first time, like significantly more important. And we realized that there are more than one thing that we should orbit around at that point. Yeah, for sure. You know, and, and it wasn't until that separation first started to exist that I realized, huh? Um I'm will, I'm not just a founder of a company. Um, there's lots of other parts of me in this company is something that I do. It's not who I am. And I think it's, I don't treat it as a job. I care about it. That's the way an artist cares about what they, you know what they paint, correct. However, I have to realize that the art is just art. You know, it's a, it's a canvas with paint on it. It's not literally me if the painting burns, I'm fine,

Ryan Rutan: right? Yeah. The reasons, you know, we can, we can justify a lot of ways. The reasons that we, we do get wound up in our startups are valid, right? Because we do put more care into it than the sandwich that you made back in the sandwich shop in Connecticut. Um, the, the ability to allow ourselves to be absorbed or to be united with the business is there. It doesn't mean that it's less important to don't want to avoid that, but to at least limit it, to acknowledge it, to understand it, right? It's very easy to do in the sandwich shop is very hard to do when it's something that you conceived and then have have have gone through blood, sweat tears and lots of other opportunity costs in order to make the startup of reality. And, and this is, you know, again, it's part of that. You use the word orbit. Startups have a ton of gravity, right? Whereas a lot of the other things we do in life may have less gravity, right parenthood, a lot of gravity, right? You know, relationships, marriage, a lot of gravity. The other things that we do a little less gravity and so, you know, they, we can, we can spin further out of their orbits and not feel it nearly as much um and get sucked back into our startup and get myopic again. Um and so I think it just takes a fairly ah well first it takes the understanding that you should be doing this right. It takes somebody telling you, hey look, you don't have to be your startup. In fact you're not right. But people probably need to hear that.

Wil Schroter: The thing is, you can't be so let me tell this story because I think this will start to, to send it home. A lot of folks listening probably haven't gone through the entire startup lifecycle yet. You know, they haven't necessarily started a company and exit it for better or for worse, meaning they haven't been through the whole life cycle and on to the next one and on to the next one, when I was building my first startup, it was the only view of the world I had in my mind, right? This was the only job I was ever going to have. The success or failure of this was the only thing that was going to define me and that was it. So it's fair to say that all of my ego, all of myself was tied to this because I hadn't been around long enough to see anything else Reminds me of my son who's four in the moment. He needs something. It's all that he knows, he has no idea what's going to happen tomorrow. He has very little sense for what happened yesterday. He can only see this. What happened for me is that when the first company sold up until that point, I was thinking if we just did this, if we just did this, if we just did this. One of those things will, will, will validate my ego and that's really what we're talking about, right? And it never happened. And so the company sells is sold for a lot, made no impact on me whatsoever. I didn't feel any different. I was talking to a friend of mine a couple weeks ago and he sold his company for a billion dollars raised no money and he said the same thing. He said, funny thing after I sold nothing changed how we talk about this, but in this case, I just want to talk about the self worth part. Yeah. The implication when we're beating ourselves up about things going negative is that when they go positive will have validated ourselves and I

Ryan Rutan: get to wear the crown around and then people acknowledge it. And all of a sudden I feel better about myself and everybody looks up to me

Wil Schroter: and and what if I could tell you that every single person I've ever spoken to myself included, felt almost no validation on the successful completion of that cycle. Which is which is why I

Ryan Rutan: remember feeling, I remember feeling it wasn't validation. I remember in selling the first one, it was a bit of relief. Sure, right? And and now that we're talking about it, it makes sense because at that point it did. And now there was this period, we've talked about this in another podcast. We did an entire episode on this around like that. You know, what happens when we exit the startup and like what do we do with ourselves? Right is particularly when we are all wrapped up in it. There was that period of, you know, depression, anxiety, you know, listlessness, there's sort of directionless floating where I didn't know what to do with myself. Um but right alongside that there was definitely a sense of relief, but to your point, not a sense of validation. I wasn't like hell yeah, I did it. I did it now I got my thing and now I can move forward, it's not what it felt like at all. There was a little bit of relief from, I no longer have to be completely tied up in that because that was the other thing is that even at points where I did feel that and did understand that perhaps I was too wound up in this thing and I was making it too much about me, I didn't know how to undo that Well, so even after the realization, I didn't know how to extricate myself from the start up,

Wil Schroter: There isn't a single requirement or inclination through this entire journey that would suggest that you detach yourself. Ever.

Ryan Rutan: Yeah, exactly. Every

Wil Schroter: single aspect to what we do only implies that you're going to, you're going to get more invested and so there is no juncture where someone steps in and says, hey, you know, right, you should probably just take some time to yourself and not worry about the startup anymore. I mean, it literally never

Ryan Rutan: happened, nope, didn't hear that, right?

Wil Schroter: And so we're caught in this really self inflicted prison, in the self inflicted is the important part. They're not the prison, we're in the self inflicted prison where we say I am stuck to this startup, how it performs is a measure of myself and if I, if I fail, I'm a failure, not that the startup fails, it's, I'm a failure the equivalent of like, Ryan, you play soccer, you don't like to lose, but I'm guessing the next day you don't sit there and like, I'm less of a human because we lost that game yesterday.

Ryan Rutan: Well, yes and no, so I, I've continued to tell the story about the, the season opener from last season um, where I, I made a great hustle play towards the end of the game and I missed the goal. Like it was by all rights, I had earned it. I had beat the last defender, I was in just me and the goalie and I just shanked the thing wide of the goal. I still revisit that moment with fair frequency and I know that I shouldn't. Um, but you know, it's one of those things where I'm trying to use it as a motivator, it's a horrible motivation, luckily I'm not attaching myself worth to it, but boy, it can be hard to let go of those moments, particularly when they're like that crystal, right? Like I'm going to pass up on an offer to sell my startup and then I never get another one right? You don't forget that moment in time, that one, that one sticks around. We're

Wil Schroter: not advocating being devoid of emotions. What we're saying is that our self worth isn't attached to it, correct. Um, you, there's no reason, it can't piss you off, that, that, that you might have shanked the ball. What you're not saying is Ryan is no longer a good person. Here's an example, you

Ryan Rutan: know, the rest of my team was saying that, but I firmly disagreed with them. So here's

Wil Schroter: an example. I've been to countless founder dinners and I know you have to and I have one of two conversations, either the conversation where the startups going well or the conversation where the startups going poorly,

Ryan Rutan: um,

Wil Schroter: or more likely the conversation where the startup actually is going poorly. But

Ryan Rutan: the founders trying to explain, right, that one's, that one's tough,

Wil Schroter: which, which look, we're all eternal optimist. So sometimes it's just, you know, our self delusion, but here's the thing when I ask, hey, how, how are things going? The first implication is that I mean at your startup. So, so hey, growth is great up into the right, you know, yada, yada and I always followed up by saying, I didn't mean your startup, how are you doing

Ryan Rutan: in the same reaction every time they spilled their drink, they're like, wait, what? Yeah, right, right.

Wil Schroter: First off, no one ever asked that, right, because no one really cares. They should, but they don't. Um, and the second is they rarely have an answer for that. Like actually not great. I was talking to a friend of mine a couple of days ago and she was, I asked her, hey, how things going like, oh things are going great, you know, business is great. I was like, how are you doing? Oh well terrible. And then I went on this whole other tangent and so I guess, uh, my thought process there is that when you, when you talk to founders, we've been almost so conditioned to express how we're doing aligned with how are startups doing that? We almost forget that there are two separate things. How often do you say, do you talk to a startup founder and say, hey, how are things going? And they say, well, startups tanking, But man, my life has never been better. Like that never happens, right. Um, and, and, and every now and then again, someone will have enough self reflection to be able to say, you know, it's been a tough year for the startup, but I just had this, this new child and you know, so it's a, it's a miracle and you know, they kind of want to talk about that a little bit, but, but something interesting happens when you've been through this cycle enough times and I really want to dig into this, you realize that you actually can't tie your sense of self to your startup. For example, when I sold the first startup as you did, it's gone, I can attach myself to it all. I want, it's actually gone. It's not mine anymore. And, and you scratch your head and I've got a few friends who have actually built really large companies, thousands of employees and right up until the day they sold, they were like the God within that organization, like everyone looked up to them and then they sold and then they were just another person. I hear this a lot from uh, folks that are like, uh, ceos of massive companies like, like a, like a G E or Disney were like one day I had, you know, 100,000 people reporting to me the next day, not even my secretary is calling me right. Like it's just this, this dramatic shift and in that moment we realize because we have no choice that it was never ours. It was never ours in the sense that it was who we are. It was something we created, but it was independent of us. It was the piece of art on the wall and that art can be moved sold burned what have you, But it's not us,

Ryan Rutan: you're absolutely right, will, you know, and while I do think of myself as a, as a thing of beauty and a piece of art and my wife has often threatened to nail me to a wall. Uh, yeah, we, we we are not the thing. Um, but let's, let's spend a little time now talking about some healthy habits, like what are some, what are some things that we can do as founders for ourselves and, and maybe more importantly for for other founders, because, you know, is we're working hard right now to um, to build out bigger and bigger wider and wider founders communities globally. Um, this is super german, I mean, this is literally one of the things that we're working on at startups dot com right now, um, and it's it's been sorely missing, but like, as as these groups come together, because historically were horrible at this type of self reflection, right? So rather than thinking about what can we do for ourselves as founders, what can we do for other founders? So as we join these groups, as we become part of the founder community, um, which sometimes happens organically. Um, but you know, if it's not, then you should seek it out. It's an important piece of survival as a founder. Um, what can we do to help folks to separate themselves from their start ups and to understand the importance and validity of doing that,

Wil Schroter: you know, the one that I use most referenced it a second ago. How are you? And sometimes I even have to preface that by, I don't care about your startup right now. How are you? To be fair, it's such a cool question to ask anybody, but I think that you have to be more deliberate about it with a startup founder, because, you know, that's not the answer they're about to give you right, and giving them an open road as well as permissions, so to speak to speak openly about how they feel. I've never asked that question. Have somebody go, oh, yeah, I just don't wanna talk about it. I mean, unless they actually didn't want to talk about it, 100% of the time when I asked the question, they say, uh, wow, thanks for asking that, because no one has been asking me that. So this is, this is a different way of saying when you're talking to other founders keep in mind, No one generally cares how they are doing. Just try to separate the two if you're at that that founder dinner of of which there's a million and the person is going on about their, their one mobile app that nobody cares about not knocking their mobile app in this context. Um, ask them how they're doing. You know, Hey, so what do you do when you're not building your startup? Which is as you can appreciate sometimes a funny answer. Um, but uh, but I guess what I'm saying is, uh, I've had the most productive conversations with other founders by orders of magnitude when I step behind the startup and I say, okay, cool, we can get to that whenever you're ready. How are you doing? Um, you know, where are you on the emotional scale 1-10, right. Uh, and start opening up that conversation. Um, you know, you mentioned this, right? It's what we do in our founder groups that we put together, You know, we put as you folks know, we put together these eight person founder groups, we get together once a month and we dig into hard stuff and people are incredibly honest. And the first question we always ask is what's keeping you up at night. Um, Ryan, as you can imagine, uh, first thing people answer is, well, it's our customer acquisition strategy and we can't, we can't find funding was like, that wasn't really the question, although that might be the answer. Um, the question is, what's keeping you up at night, like, and we deliberately separate, uh, you're here as a founder, not as a startup ambassador, right? Yeah, Yeah. And I can, I'm sure you've seen this, the conversation changes so dramatically. It becomes so much more real.

Ryan Rutan: Yeah, real and personal. And, and honest. I think that it's, it's another, you know, just manifestation of the startup world, but and not not that were, you know, a bunch of pathological liars, but as we've both said before, we're eternal optimists, right? And sometimes we have to keep talking about things as if they will be true or talking about them as if they are true. When what we're really saying is we hope this will become true, right? And and so I think that, you know, that tends to start to flavor conversation and response, um, in in almost almost pathological way, right? We're just conditioned to respond in ways where all things go back to the start up and everything's okay. Um, even if we ask about the problems, right? We we tend to downplay those, but we never turned the corner fully to look back at ourselves. It never really goes there, right. It's never, I'm, you know, what's keeping up at night, customer acquisition? Well, that may be true, but why are you worried about that? Right. Why is that affecting you at such a personal level? Um, you know that it's that it's keeping you up at night. This is where that separation between the business and the founder becomes so critical because if you can't see that and if you are again attaching, you know, you're enough of your psyche, your ego to that, that you're literally losing sleep over now. There are times and there are problems that require that level, right? But you're absolutely right that we need to dig in personally get people talking about themselves. Um, because to the, to the degree that, you know, the startups are a manifestation of the founder. Um, you know, they're not one and the same thing, but looking at yourself and being honest about where you are physically mentally emotionally, um, has an impact. Right? If you're going to say on one hand that all I am is my startup, then why do we spend so little time looking at ourselves and caring about ourselves?

Wil Schroter: Yeah, I agree. And I think so, once we start to realize that we actually can't be our startup as much as we'd like to be. I think that alone creates some some necessary separation. I think the second part is starting to teach others and teach ourselves how to have conversations about the difference, the delta between us and our startups, recognizing that yes, I'm working on the startup and it might become a big thing someday, but that's actually not who I am. That's just, that's something that I create in the world. One of the things that's been super helpful for me is the reason I got into carpentry is because I needed something to kind of remind me that the work that I do is just a separate thing, right? So like when I would go outside and I'd go to my workshop, I would start building something. I didn't even really care what it was. I just wanted to be able to work on something and kind of to provide that creative energy, that that kind of productivity on something where there's just no way I could really attach my sense of self worth. Right? I just finished my deck. It's a sweet deck. But you know what, I'm not that hung up on it. If it was less of a sweet deck, I wouldn't be like crying about it, it wouldn't keep me up at night whatsoever. And it's because it's not who I am, it's an it's an output of what I do, but it's not who I am and the more I start to attach that same reasoning and logic to my startup. The happier I become, it's actually just that simple and here's the caveat. Last thought there. And it's going really well. The startup that Ryan that you and I work at is our dream job. It's going incredibly well. This isn't me chest pounding and it worked really hard for us to make this statement that it wasn't always this way. Um, so it's, it's me saying I don't want to attach my sense of self to the startup, even when it's going well, because I know there's no way to ever fix that problem if it goes anything other than well,

Ryan Rutan: 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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