Startup Therapy Podcast

Episode #93


Ryan Rutan: Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan joined as always by my friend and the founder of startups dot com, Wil schroder will Today, we're gonna talk about something that through our long and storied careers as founders, our relationship has probably changed with this particular topic and that's around founder commitment. Like as you go back, like what, what does founder commitment mean to you? And, and more importantly, like go back in time and like where did you start with founder commitment compared to where you are now?

Wil Schroter: Well, it has been a along and as you said, story journey of me trying to figure out one simple question, why isn't anyone as committed as the founder that startup? And I think if I look back at this kind of highlight reel of all the moments where I started to have this question where I can actually just picture it in my head. I remember pulling into the office, this was like a few years into my first startup, but remember pulling into the office at like six a.m. This, I don't know why I was like, that was a thing back then, but like the big thing was always arrived before everyone and you left after everyone. I want to kill the guy that that said that not helpful but not helpful, but it was a thing. And uh, oh and I bought into it. So at six a.m. I rolled my car and it's the only car there and I'm looking around and saying, what the hell? Why is anybody here? Okay, I wanna hang on a second

Ryan Rutan: though. Early, early on. Were you paying anybody well enough to have a car?

Wil Schroter: Oh no, this is, this is well until we had car money, you know? Yeah, let's get into it. Uh, we didn't have roller blade money going into it. So you know, I pictured this moment rolling in the parking lot, my only my headlights and thinking as I'm walking into the building, what the hell? Like why am I the only person here? Yeah, fast forward to later in the day in the evening. I'm walking out to that same car at midnight and I'm the only car they're looking around saying, what the hell, why am I the only car here? I remember when the company took a header and everyone was running for the exits and I was like, what the hell? I'm the only person here and for some reason and this is going to probably become more evident throughout this uh, this episode. I just kept thinking that by some version of osmosis and or some better management or incentive plan that I'd come up with that I could get everyone else to care about the start up the way I did where I would just what I want to call Ryan effortlessly make those commitments without even thinking twice about it. And it took me a long time to realize that nobody else would. And I don't think, you know, I don't think this is a matter of working hard. A lot of people work hard. This is just raw commitment. I am just so tethered to this thing. Like nobody else's. And the question keeps coming back. Why isn't anybody else?

Ryan Rutan: Yeah, man, I mean, obviously, there there are a lot of things that lead to the staff being less committed and the founder being more committed. And that's what we're here for today. Let's um, let's unpack all of it. All right. Let's walk through as many of these things as we can. Certainly, we both have plenty of of personal stories of the midnight oil burning glory that somehow you don't get the merit badge for all of the other bad behaviors that one can associate with having these high level of expectations. But why don't we talk first about why this exists for the founder, right? Like what is it that sets us apart? Why is it that, you know, we're the ones awake at three a.m. And only us. Um, let's isolate the founders first. Before we before we start to talk about, you know, where commitment starts to drop off. Let's talk about why it is that we have this like absolute, you know, when we use the word commitment. Like, you know, all founders should be committed. I heard somebody say that once. And the first thing I pictured was an insanitary. Um right, insane asylum. Like yeah, like that type of commitment. Yeah, probably true. Um, but let's talk about that, like why is it that that we have this insane level of expectation.

Wil Schroter: I think at first it's because it becomes so natural for us, right? Imagine meeting someone and being so wildly in love with them. And then I'm saying I actually have no interest in you whatsoever actually described my entire dating career. So I think, I think what it comes down to is we feel so strongly and so naturally this feeling, this emotion, this tethering and it just feels odd that someone else who's about to do the same job that we do with the same idea that we, that we're working on that just doesn't share that same attribute. It seems odd, right? And I think for a lot of us as founders, especially if this is our first time out, we think that maybe at least I did. I thought that maybe the reason other folks weren't as committed, it's just because I did something wrong, Right? I didn't create a calm plan that was as strong as it could have been, right. So incentives weren't there or I didn't manage well enough. You know, maybe I was supposed to just be a hardhats and commitment comes from just telling people they need to be at their desk for 14 hours a day. And that's what commitment is. I thought it was all these things that I was missing and I tend to blame myself for everything. And so I think what happened Ryan is after a while I realized that no matter what I did, no matter how much incentive comp I created or how, you know, hard I pushed folks, I couldn't make a commitment happen, right? Especially my level of commitment. Do you know

Ryan Rutan: what, That's a tough realization. I want to circle back around that in a little bit. But there was something that you touched on in a recent conversation was that for the founders, it's not just about upside. I want to circle back to this point though, around what creates it doesn't create a why that same level of buying isn't there? And how painful that can be and and how we can blame ourselves. There's there's a whole segment that I think we need to do on that, but before we get there will, like you put it really well, like you said, that we work out of fear and not just upside right, Right? And and that has a very, very impactful outcome in terms of how the interests are aligned, right? In terms of, you know, if you're only if you're all motivated by upside right, that's going to have some level of limitation on your commitment, right? If you're only running towards something and not like most founders simultaneously running away from the thing that they're afraid of, which is failure and running towards the thing that you are trying to chase down, which is your business, that's a big deal.

Wil Schroter: I think that for a lot of founders, uh, we vastly overlooked on this one. You know, working out of fear, not just upside is that when something good happens to the business, it kind of reflects everybody the same way. Like if the business grows, let's say or becomes more profitable, everyone can kind of do some mental math about how that benefits them, yep. But when things go sideways as they kind of always do that math definitely doesn't spread the same way, Right? So for example, if a company has some major lawsuit go against it, right? A lot of the folks, let's say in the sales team are gonna go, oh my God, this is gonna be much harder for me to sell or the dev team can become, we might lose our jobs and all of those things are, are awful, right? But the founding team is like, dude, what if this comes back to me personally, you can correct like what if I get bankrupted by this, right? That is not the same level of process and that's more of an apocalyptic version. If we dial that down a bit and we say, hey, the company just lost a major customer, right? It's not necessarily going to end the company, But man, like I might have to let go of 20 people That doesn't necessarily affect everybody else other than 20 people quite the same way

Ryan Rutan: Well and even those 20 people, it doesn't affect in the, in the same way and again, not that it's not bad. Not that it's not terrible, but you know, being let go Impacts that individual and they get to deal with that as an individual. They're going to find other job letting go of 20 people at one time is an absolutely dreadful experience for anybody who's been through it, Right? You have to go through hell 20 times over, right? And it feels awful and it feels like a huge failure. And again, so this is why that commitment level exists and why there's a delta between the two, right? Because of these types of downside um events we push harder. We stay up later. We, you know, we do whatever it is we think we can. And again, like you said, your relationship with has changed his mind, not necessarily the right thing to do, but in the absence of of knowing what the right thing is to do. We just tend to stay in motion and we're just like, I'm just gonna keep working. I'm gonna push harder. I'm going to try more. I'm going to just by, by brute force, try to make this work, right? And it's that's where we see this commitment manifests itself in some of the worst ways, honestly. But honestly, I you also go back and say, like, what else would I have done in that case, right? Could I have left the office at 5:00 knowing that I was gonna need to let you know, five or 10 people go, you know the following day.

Wil Schroter: Yeah. You wanna, you wanna believe there's some element of control there. Yeah, right. I remember the first time that I had to tell the staff that we didn't have enough cash to pay them. It was a small staff. We had a handful of people, right? But it might as well have 100 people, It didn't matter the impact felt the same. And we're sitting across from the team and explaining them that hey, just because of the way client contracts came in and etcetera, we weren't gonna have enough cash to to pay everybody and I need to have the conversation up front because you can't run payroll obviously without having cash. And so I had this conversation and this was just such a transformative moment. I remember sitting at my desk That I bought at staples for $400. I was so incredibly proud of that desk. And I remember sitting at my desk and in talking to the other, the rest of the team members who are all sitting at their desks. We had like one giant open room and we're all just yelling across from each other and being like, look guys, there's, there's nothing I can do. And they were cool about it to an extent, but here's what happened that I didn't expect. I thought they were going to say no sweat, we'll just go a couple of pay periods and you can make it up to us later, kind of thing, like an Iou not at all. They were like, no, they were like, okay, cool, see you. And I was like, wait, hold on a second, I thought we were all in this together, and they're like, no, you're in this together, I'm in it for the part where I get paid for everything else, that's your job. And it was, I remember just coming home from that and just being so devastated, right? Like it felt like I thought I was in a marriage and everybody else just thought we were just hanging out, right? And again, I didn't have any concept for why that just wasn't something I did wrong. I thought I must have made some critical error in how I convinced those folks are engaged those folks or built relationships with those folks, that their commitment would have outlasted anything, including not getting paid was totally ridiculous. But lo and behold it did

Ryan Rutan: not did not. But I mean, that's that's, you know, when when you're able to lean back and look at it, of course not, right. And it's that level of commitment where people can be committed and they're willing to work really, really hard and drive towards the upside, but they're not willing to tolerate even a little bit of downside. Um And and that's generally true, right, That's just some of that human nature, you know, there's a lot of things that go into that, of course it depends on the situation, right. If there's sort of writing on the wall, we've talked about this before to where sometimes founders are the last ones to see that. And we're like, you know, we talked about in the context of investors like getting that. We wrote you off as a loss a year and a half ago. You don't need to come and apologize to us. We knew you were going out of business. Often founders the last ones to see these things. And I think that that can also, that can also cause cause some serious founder level pain. Um, I remember feeling that as, you know, I was seeing people starting to kind of jump ship and I'm like, but it's not that bad, is it? Well, you know, we're not, we're not doing that poorly. Um, and then it turns out we were right and they, you know, they took their interests and did what they needed to do to protect themselves, which, you know, I don't begrudge anybody. Um, in hindsight certainly wasn't happy with them at the time, right? Like, like you, I went home and I'm like, man, you know, all these people that I thought were in it with me. You know, the second things started to, you know, turn a little bit south or just, you know, even slow down. They were gone, right, they just went on to something that they felt was better, which speaks entirely to commitment.

Wil Schroter: Well, you know, it's funny, I had this great commitment discussion in the form of an equity discussion, this is, this had to be almost 20 years ago. and I was doing a second or third startup at the time, and we're putting together the equity plan, essentially. And it was a handful of folks that were kind of uneasy with what the plan was. We had stock options, not equity. And uh, so they sat down with me and they said, we want to be treated like, like owners in this business, and I was like, okay, um, are you sure? And they said, yeah, you know, we want we want equity in the company, and I was like, okay, let me just spell this out for you right now, we're losing between 50 to $70,000 a month, and your pro rata share of that loss would be this, So by, by virtue of being an owner in the business, you're now responsible for that share every month, because I know I am, that's kind of what ownership feels like, and all of a sudden there, what do you mean? I was like, well, yeah, and then you owe your version of taxes, uh, like, you're, you're an owner that's actually how ownership works. Yeah, vis a vis commitment. And they were like, that's ridiculous, I don't want any part of that, I just want more ownership and the good things that happened and I was like, that's that's

Ryan Rutan: that's that's what you have in your hand right now. Yeah, yeah, A ticket for when things go well. Yeah,

Wil Schroter: exactly. That's and again, this is this is all part of my point. I think I had inadvertently projected some of those frustrations, if you will, or, you know, my frustration was around folks not being as committed and I don't, I don't think I ever really understood why they weren't as committed. I think I I felt a bit robbed of working so hard and not kind of seeing their version of that is not the same hard work. A lot of people worked really hard, but it's just raw commitment. And I think after a while, after a long while Ryan, I started to understand that this was really about Not being on the same side of the table, 100%, you know what I mean?

Ryan Rutan: There's yeah, there's a lot to be said for that, right? And I mean, our baby, right? This is the thing that we brought to life and I think that's a huge part of that chasm and separation you and I have talked about this as as founders for right or for wrong. We wrap ourselves up in this and, and not just in the idea and not just like that, you know, we've talked an entire episode about, you know, separating yourself from your startup, you are not your startup, you are to some degree and at certain points more so than others, but beyond that, it's about how other people receive it, right? And it's it's it's about how they buy in. Do they buy into it to the level that we do? Typically not, but like there's still like, there's a lot of our self worth gets tied up in being able to make people see our dream alright. We've talked about this too, like we're always in pitch mode, right? Because we're always trying to get people to see around that corner into this beautiful future where this thing is built and it's doing what we wanted to do the future dream and we want them to see it the same way as close to that as as we do, and that's just not the case for most right. You know, if you're lucky, the co founders are all on the same, you know, same cloud level in terms of the dream, right? As you move down the staffing line, the expectation there should change, it doesn't and and we do this well, well outside of even our own teams, it's just people we run into, right? We pitch and we tell them what we're doing and we want them to buy into that dream and and when people don't have that same level of buy in, there can be a lot of pain, I mean, I think we both already kind of alluded to this in in anecdotes we told earlier, but that was really a big part of of what hurt when I saw people bail was that it was obvious that they didn't still see the dream in the same way, right? That they let some what I was thinking of as a short term circumstance change the dream and I absolutely wasn't willing to do that and why? Because I was committed to the dream right? And I was committed to the dream at a particular level. Their level of commitment and probably what they saw as the dream were two different things right? And of course you're gonna have some people who don't buy into the dream at all right? Like they just I'm a contract developer. I come in and I just do the work you need me to do and you pay me and that's my dream. My dream is for you to pay me That's a very different level of commitment that comes out of that. Right? Again, we've talked about this problem around validation but it does make you feel a certain way right? I remember feeling extremely, extremely devastated and sad when I realized that people didn't have the same level of dream that I did because I wanted him to right and not just to validate me, but like part of it for me has always been getting people to buy into the dream to be able to do something really amazing and beautiful with people that I want to surround myself with with people who I think will add to that dream and make it something better, right? And so there's a huge emotional component to that. And when you realize that you've been misleading yourself, I don't think I've ever been misled by someone else. I think it's always been my problem, not a third party problem where like they were misleading me and and like leading me on and making me think that they believed in my dream, I just think I was overstating in my own mind how much of their dream this was and that hurt like hell,

Wil Schroter: I'm sure, I think part of that is when we had this idea for for whatever this, you know, this dream for whatever this business was, you get this, this inception quality, right? That like I've had this thing from the beginning reminds me of building a sandcastle and I've got this idea of how big this thing can be. And so to me, when it hits that threshold, it becomes that thing, I have the full arc of creation in my mind, right? Somebody else that just comes over with the bucket and just throw some dirt on it and is like, hey, this is, you know, this is a little bit bigger, they'll look at that and go, hey, this is magnificent what we built, but I don't think that they see the full arc that they're not as invested in it. Right? The same way I think about having kids, like I am so invested in my Children in their, their careers, so to speak and you know, their career of life, nobody else is right? And at which point I think the babysitter should care as much about my kid as I do. Like I'm, I'm kind of missing the point, right?

Ryan Rutan: Yeah, no, we, we have to be, we have to be realistic about these things, um, both for, for our own self preservation and to be fair to these individuals, right? You know, it's, there is a level of expectation that's too much. I think it was my, my mother that told me once, you know that the fastest way to be disappointed is to set expectations for other people. Like, you know, setting expectations for yourself, but don't set expectations for other people, right? She said you can set up the scenarios, you can set up the situations where they could produce or or manifest those things that you expect. But having the expectations itself is not healthy. And she was not wrong.

Wil Schroter: I think there's another way to look at it and I agree with everything you just said. But I think another way to look at it is the commitment to this thing to seeing it through. That's your job as a founder, right? It's your job to have that commitment. So like what I didn't understand was I'm I'm at work at six in the morning, I'm at work at midnight, I'm at work on the weekends, I'm up at three a.m. Et cetera. That's my fucking job, right? As the founder, right? That's not something special that, you know, that only you can do unless you are the founder, right? And if I'm sitting here going, hey, I guess that's my job, why isn't everybody else doing it? That's on me? You know what I mean?

Ryan Rutan: Yeah, exactly. Yeah. It goes back to, you know, what we can expect of others and what we should expect of ourselves and that's it, we get it wrong on both hands, we set really bad expectations for ourselves and we tend to to to set, you know, high expectations for others in some cases far too high. Um, and I think I've already shared this, but I'll share it again, because it's definitely relevant here as well. Um, and it was one of those just really galvanizing lessons in my life where I had, I had achieved something that I wanted, which was to become the captain of our high school soccer team. And then I wielded that responsibility uh, with uh, with not a lot of grace and I essentially became a tyrant and was pushing people, you know, in my mind, I was motivating them and I just started to be like a huge jerk to everybody on the team. I'm thinking that that was going to be the thing that would push us to, to the next level. I remember the coach pulling me aside after a practice and saying, hey look, you really got to tone it down, it's like you're, you're losing the team here. You know, I understand what you're trying to do, but you know, this is, this is not okay, um, is like if I have to, I'll relieve you of your duty and man what a punch to the gut, like just took the wind out of me completely because here I was thinking that I was motivating people that and you know, I was leading by example and I remember the reason that it really hurt. It was at that time I was, I was putting in the extra hours I was doing the extra training, I was, you know, coming to practice earlier, I was staying late, I'd stay and, and you know, take shots for an extra hour and a half. I'd run, I'd do all this other stuff and I said to him, I like my again, like not hearing the wisdom and what he was telling me and not having enough perspective to say like, yeah, you're right, I'm screwing this up big time. I respond with, but I'm pushing myself harder than any of them. So none of them should have an issue with this. And he looked at me and said, who the hell are you to decide how much they get to care about soccer. Great point, right? It was, it was a fantastic lesson and, and it stuck with me and I think that's, that's, it's helped me. Certainly, I had to relearn it in business, but at least I had this to lean on and go, oh, hey, you know what, I think I've already learned this lesson before. But you know, as I was starting companies, I had to go through that that same process of realizing that I can't set that level of expectation just because I'm willing to do even more. Like I can't use myself as the bar even if I'm holding that bar and saying, well you just do 50% of what I do even, that's not necessarily fair, right? Because it goes back to this overlap between, you know, how invested in the dream are they? You know, how close to that inception moment where they, and you know, what is there, what is their commitment level to this thing and and how much of the dream are they really buying into and just not to set those expectations, right? You know, lead by example in ways that feel good, but you can't expect everybody to follow.

Wil Schroter: I agree. I gotta tell you man, what I did is I thought that I could transfer commitment by way of title, right? So I said, I said, look, if I hire another Ceo in my place, they're the Ceo, I was the Ceo when they become the Ceo they'll be up at three in the morning, they'll care about all this stuff so on and so forth. And I tried it so many times with so many companies with, to be fair, really good people, Right? So this wasn't even like a a lack of finding the right people and damned if every time I did it I was sufficiently disappointed. And again, I think this speaks to what you said. You nailed it with your analogy on the soccer. I didn't miss because they were the wrong people I missed because I was making the wrong assumption that commitment could be transferred or should be or it's your point that I even had the the right to make that transfer.

Ryan Rutan: Yeah, it's it's we just we don't have that right to set expectations for other people for how much they should care or do care the best we can do. Right? And again, we have to try to do it without wrapping too much of our self worth up in. This is to get people to buy into our dream right and right? And and not in a way that, you know, we're we're trying to to do it as a manipulation technique, right? I'm not trying to, you know, get people drunk on the dream so that they'll do things that they shouldn't do. But when people are properly motivated when they're properly incentivized and there's a strong buy in and tie into the dream, their lives are better off to, right. And so what I've started to think about as we've been going through this discussion is that commitment for for the founder, you've said this commitment is our superpower, right? It's something that allows us to do what we do. But commitment for everybody else is actually an incredible gift if we give it in the right way, it's a gift to the people around us, because the feeling of commitment is a good one, right? Being drawn into doing that thing you do and wanting to be part of it, right? And being committed actually feels fantastic. I can analogize this to marriage. My wife and I had a discussion a few weeks ago around how happy we are about the level of commitment we have to each other, right? That that commitment feels good when we know and both for ourselves, and the reflection of that commitment feels amazing. And so now, as I'm thinking through this, as we've talked through it today, right? You're absolutely right that our commitment as a founder is a superpower. Our ability to open the doors for people to be committed within our startups is a gift, both for us and for them. But I think that's how we should think about it. That's how we should treat it.

Wil Schroter: Yeah, I think in my view, I think that as the founder, this is what I've come to learn over a massive number of failings for damn near three decades. There are certain things that I signed up for, whether I realized it or not as a founder, that are my responsibility at its core and what I mean by that is there are walls that I have to run through that another nobody else will write and that's my job. There are certain aspects of this job where I do have to worry about all the downsides in a way that nobody else should have to worry about the downsides. That's my job, right? So I feel like instead of being a feeling like, you know, we've been robbed in some way of other people not taking up that mantle. Instead, we should be proud of our commitment, we should be proud of the role that we're responsible for and consider this. Uh, the old Spider man is saying with great commitment comes great responsibility.

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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