Startup Therapy Podcast

Episode #55

Ryan Rutan: Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan joined as ever by Wil schroder startups dot com, Ceo and founder, well, we talk a lot about how inextricable founder personalities can be from the businesses and how, you know, we often get our entire identity wrapped up in the business, which can be great. But it can also, it can also go the other way. What happens when a founder's personality becomes a liability for the startup?

Wil Schroter: Well, yeah, it's a problem because the founder is the one that has to determine that the founders the liability of the company. And how many people like actually have that much self awareness that they would even understand that they should look for that because it's like everybody in life, right? Like we all think that whatever problems we have in life or somebody else's problems that I'm just dealing with. It's very rare that you hear someone say, you know, actually the problem is me and these other people are just like a reflection of my issues.

Ryan Rutan: Yeah. Just when you're lying about a breakup, No, no, it's not you. It's me.

Wil Schroter: And then on top right. And then on top of that for the founder, all guns are pointing toward us, right? You know everything, everybody's all eyes are on us. And so we're sitting there going, okay, we have to project this image where we're doing everything right and we're trying to make all the right decisions. It's really hard for us to raise our hand and say, hey, am I doing everything wrong. And then even if you do the people that you're typically asking like your co workers, co founders employees, whatever the last thing on their mind is, let me tell you what an a hole you are and risk the fallout that comes with that. So it's like the emperors, you know, it's got no clothes, like no one's going to tell you how things really are. And yet our personalities, our flaws, our issues are even our strengths are all the largest reflection of the organization. Especially, especially, you know, in the early years when there isn't that big of a company. Imagine what the problem is when you say adam from we work or Travis from Uber and your personality is such a massive reflection of the systemic problems in a company and you're unwilling to admit it.

Ryan Rutan: Yeah. And, and as you said before, right, you probably, you need to recognize it because you're the only one that can probably do something about it. If you're sitting in the top chair like that, somebody else is going to come and tell you any of this is pretty slim. And so you do need to recognize it. On the other hand, as you said, everybody else has probably already recognized this. Well, I just had a great product idea, had a great product that we're going to set up a filter in slack that looks for a founder name plus asshole or other, you know what we can, we make a list there and when it sees that in combination more than four times a day, it's just gonna send an alert anonymously to the founder, letting them know you might be an asshole.

Wil Schroter: Well her alerts have been going off non stop. So right, let me paint a little bit of a picture of Early on in my first startup. Kind of the first time I saw this, it's always too late by the way, like, you know, nobody sees it when they should. But the first time when I saw this and kind of how it manifested, so like 25 years old, the company has grown quite a bit. We've got hundreds and hundreds of employees at this point, I've obviously never done this before. I have no idea, you know how I'm supposed to act. And then the other challenge that you have When you're that young, let's say like in your, in your 20's you kinda haven't been around long enough yet to know what you should or shouldn't do. I mean that's literally the part of your life where you're, you're learning right, where all these things are happening for the first time.

Ryan Rutan: Well and in your case and in mind neither of us had had the experience of being on the other side of that coin, right? Where we were the ones looking up at a founder or a boss and saying, gosh, what an asshole. And so we didn't even have the warning sign, right? We didn't, we didn't have anything to say, like, oh, that's what this looks like.

Wil Schroter: You also interestingly again, and we've referred to this before in other episodes, but it was also during a time period called the mid nineties where being a 25 year old Ceo didn't exist yet. So literally no one knew how this goes, right? I mean everybody just assumed it was a one off fluke and it would all go back to, you know the way things were with Silver haired 50 something's getting their first promotion to become

Ryan Rutan: president right now. I'm just thinking at that point in my life, if somebody had come and called me an asshole, I've probably been like, man, that sounds so grown up, I would have been

Wil Schroter: proud of it. I know, right? And so for me, I'm at this point where I'm straddling two things, trying to understand what it meant to be a leader and a Ceo, which in and of itself is a long journey that I didn't have a lot of time to learn, right? And then the second part of it was just being a 25 year old kid, Right? And like at which point like what's appropriate for just being a 25 year old kid and what's appropriate for being 25 years old as a ceo lines are blurred, All of my friends are just getting out of college, they're still working at their first shitty job, right? So by comparison it's like I'm having a beer talking about how, hey guys, how are you dealing with this? Because no one's dealing with it. So that was bad enough on top of that, I'm also kind of an a hole, right? So you've got this, this compounding, you know, situation where I don't know what to do. I'm going into total muddy waters and I'm not the coolest guy to begin with, right? And so like I'm dealing with how my personality as I become an adult is going to be reflected in a world that's never kind of existed before, total shit show, right? However, I will say I had at least the self awareness to know that I probably probably was screwing something up at this point, right? I don't know where you were in your twenties, as far as like your maturity scale. Mine was pretty low,

Ryan Rutan: I would say, Yeah, I had my moments, I definitely had my moments, I think that I was always referred to as being kind of the, I was too old for my age and that kind of thing when I was very young, but college helped me fix that. I got to go back to being a total knucklehead at some point and regardless of, you know, kind of how well mannered I was, there's still certain things that just come with time and experience and a lot of these, I just had not dealt with particularly the kind of one on one personal struggle. So when when somebody would come to me with, you know, an issue, my emotional intelligence at that point was far outstripped by every other type of intelligence possible not to say that I was super smart in any other area, but I was way smarter in those than I was emotionally, and that was where I felt it the most in hindsight, mostly, right? Like I, you know, somebody would come to me with a problem, I would have handled it very poorly, then they would be very upset, which I would hear about third party from somebody else who came back and said, hey, you know, why did you act like such an asshole to him when he came to you and told you all that, like, I didn't know that I did, and I don't know what to do about it now. So yeah, so I was very, very much ill equipped and learning on the job at that point.

Wil Schroter: Okay, so but again, all these things exacerbate for a founder, especially a young founder, you're going through life, you're becoming an adult for the first time. And I don't mean that in a condescending way. I mean, just that's how it works. I mean that's how you start to kind of learn how the world works. You have all these interactions you didn't have before, but then it gets compounded because now you're the founder of a company c it's not the same as like when you're an employee of a company, when you're an employee of a company and you're a crappy employee, you have a manager that steps in and it's like, hey, here's what you're doing wrong and there, whether you like it or not, they're kind of honest with you and they kind of share with you exactly what you should or shouldn't be doing when you're the founder and you screw stuff up, no one tells you. So you're just like, you know, no one pulls you aside. It's like, whoa, You probably shouldn't have said that. You know, if they had, I would have had somebody pulling me aside like every nine minutes, right? There would have been like, yeah,

Ryan Rutan: it would have looked like drawing and quartering in my case. Like I would have been torn to pieces.

Wil Schroter: Oh my God, right. I would've been fired every day of my career. But here's the thing, man, like we're in this position where all these people are relying on us to have it figured out. Haven't figured out, not just the business or anything like that, Haven't figured out. Like have your maturity, right? Not be an a hole, have empathy. Like have all of these things in line that require a tremendous amount of time and to be fair, most people never get it right, That's absolutely right. So this isn't just like, hey, if I'm around long enough, I get a grandfather into it, Most people are jerks their entire lives and most people are liabilities to themselves, their relationships and everything else their entire lives, they just typically aren't founders, right? So the exponential problem doesn't exist in the same way.

Ryan Rutan: You know, going back in time. I think one of the only saving grace is in all of this was the fact that I had mostly hired friends and classmates or at least people in the same age cohort. And so they also didn't know what it looked like or meant to be a grown up or what appropriate workplace culture was or how you should treat employees or be treated as an employee. And that's probably the only thing that saved me from even bigger blowups. Not that they didn't exist, but I think that was really, you know, the fact that everybody was kind of growing up together was the saving grace and all of this for me.

Wil Schroter: I think some of the age did help because my peers were my age, right? So after work we could go out for a drink and they would just call me an a hole, right? And kind of forget that I was there boss, right? But like it's just something friends would do because you know, we're all young, whatever. You know, maybe that's an important segue here Ryan because part of what we're talking about is if we are the liability of the company, if we are the one making working everybody too hard or stressing everybody out or creating a combativeness or creating, you know a politically charged situation. How do we find out that we're the liability? What for the liability right now? And we're the only person that doesn't know it right? You know, how do we uncover that? Well,

Ryan Rutan: this is probably a weird time to bring this up will, but uh, since you've opened the door, you know, again that part of that is maturity. Right? And so some of that does and I don't know that it just comes with time, but it comes with the experiences that tend to come from being immature. But a big part of that does come maturity and understanding the value in self reflection, introspection. But in terms of turning that corner in time, especially, you know, if you're a first time founder and kind of realizing that before major damage is done is something I don't see happen all that often. I feel like everybody sort of has the same trajectory. Maybe we can change that. Hopefully people listening today are still in a, you know, kind of in a safer space. But it sounds like yours came from the same place minded, which was that I smacked my head on the bar enough times to finally figure out to duck and that was really it right. And so my self awareness was very hard earned probably the first two times if I'm honest And then in company three I was doing better about being a bit more self aware. I was certainly older, maybe a bit more mature and had at least taken enough wounds from bad actions to know that I wanted to avoid them in the future. But I don't know a lot of people who just kind of walked in zen like and we're like, hey, you know what, I'm going to think about how I fit into this situation before I say or do anything else. I don't know too many founders that started off with that level of maturity.

Wil Schroter: You know, when I think about it though, when I go back, Ryan, like I rewind way back and I'm thinking like, And when I'm making my first hires, you know, I'm 22, the people I'm hiring at the time are like 44 and they're telling me like every day like, hey, are you sure you're old enough to be hiring me? This isn't at the time breeding a ton of security for me. Like in other words, I'm so young and I felt so displaced by where I was being a ceo etcetera at such a young age that I was inherently very insecure. So for me to start to reach out a little bit and say, hey, am I doing a good job? Wasn't that foreign to me because again, I didn't really expect to be in this job to begin with. And so I pulled a couple of people aside and I was like, look, I know I'm not a total treat here to work with. I was like, I know I'm combative in meetings, I know that I have crazy A. D d. I know that I tend to think that I'm right. Like I basically say here's what we're supposed to do and I wait for everybody else to come on board with exactly what I decided was the right answer. And like in my mind, I knew there were some problems but I didnt understand quite how significant those were. And then I dropped the bomb. You tell me what I could be changing. And but here, but here's what I did. Well, and I have to say this because I think this is an important part of how other folks can do it. I didn't say, tell me what a screw up I am. Tell me how I'm messing things up. I said I want to improve my communication, where are some areas that I can do a little bit better? Right? Sure. That said that was like giving the keys to like everything everybody has been saying about me the entire time, right? And I got way more feedback ever expected to get. And they're like combative would be an understatement, right? Like people find you flat out annoying to work with right there, like your insecurities come through in 50 different ways and here they all are. I mean it was like your psychologist finally just saying you are batshit. Yeah, and I was I mean I've never forget like during these conversations it all happened like in one afternoon because I asked one of my friends and again he was very open with me way more open than I thought he'd be. And then I was like, whoa, does anybody else feel this way? And I went to another friend thinking they were like, oh I don't know what he's talking about and they were more like and then this and this, I was like wow. And it just shook me man. Like I got to a point where I was like I'm this far off and no one has told me, I mean, whoa right. And then I think about, well man, like we're a client facing business in the agency business, how how many clients felt this way and never told me or you know, didn't sign with us because they felt this way. How many people never came to work with us? How many people left? You know, like it all dawned on me at that one moment. What a liability I was and how important it was to fix that.

Ryan Rutan: Yeah, there's a couple things that you touched on I think are really, really important here. The one around the insecurity piece I think is is critical and I think this is one of the things that can they can actually really stop people from seeking this feedback in the first place, and that's a really, really bad move, right? Because whether you're aware of it or not, whether you're getting the feedback or not, these thoughts are already occurring in the people around you, having them out on the table actually allows you to do something about them. And we talked about this before another episode, but a lot of that insecurity stems from the fact that you don't feel prepared for the job, right? You said that specifically, and I know a lot of us have felt that way where all of a sudden were thrust into something that there is no way to be prepared for, and we've taken that further in the discussion that you and I had a couple of weeks ago, which surrounded the idea that this changes over time. Alright, we end up with a new job every you know, probably 3-4 months as a startup founder in the early days because the business changes so fast and so then we're constantly thrust into new things that we, even if we had started to feel pretty good about what we were doing all of a sudden now that the playing field has changed, we got to do something new and income, the insecurities again. And so, you know, this is something that you may have to revisit more than one time, and in fact you will have to revisit it more than once, but it's worth doing right? It's really worth taking the time to do this. Getting feedback from people around you. One of the things that I found helped me a lot, and it was it was actually partially driven by the insecurity, I didn't want to talk to the people who I knew could give me direct feedback. So what I started with was a half measure. I was reaching out to people who were kind of third party, so I had a couple of advisers, I had a couple of mentors, two of those were professors of mine, and so we already had an existing relationship and we were, you know, spending time together and I was already used to asking them questions and I felt comfortable, so you have somebody like that in your circle of influence, definitely worth reaching out to them, and I found that to be a little bit easier from the insecurity standpoint, because I was able to control the information little bit, was it as useful as going directly to the people I was impacting? Probably not. But did it feel better for me and get me started down the right path? I think so,

Wil Schroter: yeah, I mean for me, and I think for you, a lot of it was just even asking for the help. Right? Which again, I don't think his founders were conditioned to do because not that we're not willing to ask for help. I don't want to, you know, undersell founders, I don't think we're willing to be vulnerable enough to say, am I wrong? Right? Especially often to people who you're probably wrong with, right? Yeah, for sure. It's interesting about this example is it's actually from startups dot com, so I have to be a little bit more muted about kind of the detail of it because it's people

Ryan Rutan: that still work here, but it just changed my name to

Wil Schroter: bob. So brian brew tan came to me, right, But this is years ago, this is like seven years ago, we don't employ. And they sat down with me and they basically said the way you've been acting the stuff that, you know, I've heard, the way you interacted with with other folks is abhorrent. And it's my first job. I've actually never had a job before, but like they were crying over delivering this information. I mean, visibly visibly hurt by my attitude, my actions, et cetera? Now, here's the thing, man, there's different ways to take that. And this is this kind of comes actually more back to not even just being a professional, just being a human, right? One way to take that is to be defensive. No, I didn't say that, I didn't mean that that's, you know, that's not how you should have taken things, you're wrong for receiving things the way you did.

Ryan Rutan: Yeah. If you want to end up a hashtag that's a great way to go about it.

Wil Schroter: Yeah, God, right. Just like but even if that were true, what a colossal mistake that would have been on my end, right, what benefit do I get after receiving this information? By correcting them right? By telling them how wrong they are. Instead I was like, tell me more. Right, where else did I come off the rails and they continued to go on and on and on. And I was like, damn, I am way off the mark. And I remember years later when they left, I brought it back up unprompted and I said, you know what, You may not have realized it, but you did me such a service by sitting me down and telling me where I stood. You saved the organization, years of evolution, me years of evolution and I really want to thank you for what you did for me, the opposite of what people were expecting to hear. And the reason I'm bringing this up is because there's probably a fair amount of folks listening to the podcast that maybe aren't founders. You know, maybe they are reporting to a founder and some work at our company and startups dot com and they're wondering should I say anything like, you know, how do I approach that Ryan, I think it's worth talking about if we're not the problem someone else's, how do we open that conversation up? And if we are the problem or the recipient were the founder? How do we respond to that? Because I don't know of a lot of people that have the emotional intelligence to be able to say it's okay if I'm wrong and listen accordingly, right or understand how important it is to receive that from the person giving it to you in a way that makes them remain honest. Because most people are going to get defensive or most people are going to try to prove why they were right because what they're missing is why it's coming up to begin with.

Ryan Rutan: Yeah, that's exactly right. Yeah. And there's a huge, huge cost in the wrong reaction to this problem, right? The how you respond to this has everything to do with whether or not you're going to come to a solution with a specific problem if you respond to this incorrectly. So if we go back to your example, if you had gotten defensive in that case and you had tried to push back and explain why they were wrong and you were right, not only would you have not gotten the rest of the information you got to that point, you never would have gotten another piece of information from that person and likely from broader circles within the organization because that stuff gets around pretty quickly, right? Oh, I finally went and told him about X, Y, Z and I got shut down right. There was no contrition. There was no listening. It just turned into, you know, an echo chamber of him telling me why I was wrong. And the cost of that long term is enormous, right? Our response in this case has far more to do with the ongoing health of the business, then the situation itself, right? And it's not to say there aren't some situations that are extremely serious, but I've encountered very few that in and of themselves were very dangerous to the company. My reaction was very dangerous. The company could have been right. And I think that that's really the how we respond to these things is the issue from start to finish, right? It's not about what happened, it's about what happens next. And so I think that, you know, again, getting feedback, making sure that, you know, you receive it in an appropriate way and that you let people know that you appreciate it and you give it the attention it deserves goes a hell of a long way and keeping those communication channels open and allowing you to be reminded that these things are ongoing issues, right? That it isn't an isolated thing. I think that's the other danger there is if you shut it down once To really bad things happen. three, probably one, they stopped communicating with you two, you don't really solve that issue. And three, you proved to yourself this is an appropriate way of dealing with this in the future and you're just going to continue that pattern from that point forward.

Wil Schroter: You know, the last thing you want is to seal off this discussion right? And I think we're conditioned in our lives when when problems come up to solve the problem by pleading our case and showing that that while we are right or in the right etcetera. And the reality is in this particular case as the founder. If we don't establish and maintain and nurture channels to get actual honest feedback to be able to modify our behavior, we are destroying the organization. We're setting a horrible precedent for ourselves. We're setting a horrible precedent for all the other managers in the company to say, well if I'm not going to listen, maybe you don't have to either conversely, if people know they can come to me be brutally honest and get actual empathy, have me sit down and say, okay, help guide guide my development. Then it's impossible for anybody else in the organization as a manager or otherwise to be so indignant about their own reception.

Ryan Rutan: And I think you touched on something really important. I think in the best case is that if you deal with that poorly and you do shut down that communication, the best cases, they resent you for it. The worst cases, they actually learn from you and they start to do it themselves that is absolute toxicity and it will spread throughout the organization.

Wil Schroter: I have way too many examples of where people came and told me what a jerk I'm not even trying to get these examples there actually just coming to me, I'll give another example. This is when we were raising for one of the companies and a very well known venture capitalist had invested some personal money into my company and he came to me at some point and he said, you know what, I really can't stand your personality. And if you knew who I was talking about, none of this would surprise you. He's very abrasive in his feedback. But but I gotta say this and it kills me to say he wasn't wrong. His words specific remember sitting at lunch and he said to me, he said, you're a chest pounder. You're running around talking about how great your startup is and how you're killing and how all these things are happening. He's like, it's bullshit. I know the numbers, right? You guys are still trying to figure your business out. Don't run around telling everybody how great you're doing until you actually do that. Well, I was like, damn right. And I remember being piste in my head. I was saying, fuck you, I was feeling attacked. I was feeling defensive, but here's what he was saying, you're a liability, your approach to how you're, you're representing this company, how you're, you're representing the investor community, The startup community, etcetera is a liability and I'm trying to help you. But being honest, he probably could have approached it a bit differently and had it been more effective, but he wasn't wrong. And from that point on, I would keep going back to him and saying, hey man, here's what I did, where am I at? Like give me a little bit of a barometer to tell me how far off the mark I was incidentally, apparently was always off the mark. You know, I was like the kid that couldn't make dad proud. But the point is he was willing to stick his neck out to establish some rapport with me. He was willing to stick his neck out to try to kind of course correct me a bit. And while it took me a little bit, I was a little bit of the horse that needed some breaking in. It did help and I did respect that channel And to this day when we have a conversation, he provides his feedback. I take it very seriously because I understand if I break that line of communication that I'm setting myself back in that I don't mean to be the liability when I hurt people's feelings when I said the wrong thing when I was combative, I don't mean to do that. I'm not letting myself off the hook. I'm just trying to say there's no malcontent there, but it doesn't mean I wasn't a jerk, right? And it's my job to own up for that. And I think it's everything that

Ryan Rutan: it is and and it's important that you're aware of it right? I mean we've talked about that from the beginning, but the issue still exists, whether you're aware of it or not. And so making sure that you've built an organization that feels comfortable sharing that kind of information with you is critical because at some point, you know, you ever tried to put a nozzle on a hose with the water running right? It's really hard to contain that kind of pressure, right? Without a huge mess. And so you don't want to try to cap that off. You don't want to try to just block the communication, you need to let it flow and you do something with it, right To your point, Most founders aren't trying to be jerks, right? It does happen, it happens and it happens to non founders, Syria, it's not limited to us either. But the awareness and the information that it takes to be aware of in the first place is that first step. And then what you do with it is everything from that point forward,

Wil Schroter: I would say this as a founder, it is my job to keep myself self aware of how my actions, of how my personality affects the organization. If I try to write everything off, like my bad behavior is in the name of the company. This is, you know, the Travis Kalanick kind of feel, which is, I'm going to bulldoze everything, but it's for the good of Uber, right? And I gotta tell you there's, there's a part of me that thinks, hey, you're not entirely wrong, but it doesn't get you off the hook either, right? Yeah, maybe that's what it took. But you were still in a hole, right? And you caused serious damage in the organization, the culture, et cetera. And you need to account for that as a founder where I make the mistakes, I know I'm going to make mistakes, right? We all do, The only thing that we can do is try to at least open ourselves up to say, look, I'm going to come off the rails from time to time, but I give you permission to kind of help me, help bring me back on. I think that's the only set of boundaries you can create to keep yourself in check if you don't, we know what that looks like. We work story, it's horrendous despite the outcome. Yeah.

Ryan Rutan: And that's the thing, right? The, and this is something that's really important to remember as founders. We do not

Wil Schroter: get the

Ryan Rutan: benefit of being able to say, well, don't question my methods, question my results, right? The methods are absolutely constantly under scrutiny and question and they should be right. We're leading the entire organization. We're setting the pace, the tempo and the culture for an entire organization of people and it impacts the business, it impacts their lives. And so we should live up to that and it's a big responsibility, but it's, it's willingly or not or knowingly or not. Rather we shoulder from the very beginning of the in the start of the organization.

Wil Schroter: I agree and I think that again, part of its setting tone, part of it is absolutely required. If you're going to be a good founder, you're going to be a good leader of anything. You have to have a level of humility and contrition that allows you to evolve if for all of us, just as humans, leadership or not, if we're not willing to say we're wrong, if we're not willing to say what could I have done better in that situation? If everyone around you is pissed right now and in your mind you have no hand in it, you're wrong right. There's no way to have two people involved in a problem where only one of it, whether it's a breakdown in communication, whether it's it's a lack of contrition and understanding humility etcetera. If there's a problem, both people have a hand in it and if there's multiple problems which there are in every single startup, right? A lack of this empathy while trying to build this big amorphous train running off the rails at the same time is like one of the biggest liabilities you could have. It's brutal.

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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