Startup Therapy Podcast

Episode #52


Ryan Rutan: Welcome back for another episode of the startup therapy podcast. This is Ryan Rutan joined as ever by Wil Schroder, my partner and the ceo of startups dot com will today, we are going to unpack a big one, the one that everybody has faced at one point or another. And I think a lot of founders struggle with this kind of throughout their careers and that's that much like everybody else in the population, we are flawed creatures. But when is it okay to talk about our flaws as a startup founder? When is it okay to show some vulnerability and to be able to kind of put it out there for other people to see and to, to be honest about what's, what's the story here?

Wil Schroter: Bring it back a little bit. Let's go back 10, 20 years. It wasn't okay to bring up your floss. I can't think of any time, let's say during my healthy on years of the 90's where it was okay to just say, this is how I'm feeling and let's share it. Like if I sat in a board meeting, if I sat in a company meeting, if I sat, I sat at lunch with you and we're like, Ryan, I've got some serious issues, you'd be like, dude, I don't think you should be telling anybody that Yeah,

Ryan Rutan: keep it, keep it quiet, man, somebody might be listening.

Wil Schroter: And there was no high five moment. I mean, it's just different times, you know, and it wasn't that long ago, it shows a sign of progress, you know, as a society, I think in an era of social media where, you know, as a group, we've, we've definitely exposed everything at this point, You know what I mean? And so I think all of our, our high points and many of our low points have become a common discussion thread online. And to be fair, it didn't start with call it ceos founders or high profile people necessarily in the past. Those were the people who had the microphone or the camera on them right there on the cover of a magazine, talking about their flaws. If they were, it started with just the every person out there kind of sharing what was wrong with them. And then all of a sudden it started to bubble up a little bit and then it started to become more of a discussion point thankfully. By the way again, I'm being thankful for this. This is me being critical. I'm just saying if we had this topic 20 years ago, is it okay to admit your flaws? I think just be no

Ryan Rutan: stop reporting. It would have been, it would have been a very early podcast, be, it would have yet would have been the shortest podcast ever, Is it Okay?

Wil Schroter: No. And, and just to be fair, like we wouldn't be having this podcast if I wouldn't, I wasn't so excited that we could even talk about this and if you listen to the startup therapy podcast, you know that a hallmark of what we do is talk about being vulnerable, right? And what kind of messed up creatures we are. We've come a long way baby. And this podcast is really a testament to life and times of what founders actually get to share, which is where our problem begins because we don't have a long history of kind of how to do this. Right. Right. So I think today

Ryan Rutan: this is all new for us. Yeah, yeah.

Wil Schroter: Get him off. And I think one of the things we get to do today and I'm really excited about it is not only talk about, you know, as founders, as executives, what our flaws might be, but how to talk to them in a method where we can understand there's consequence to talking about these flaws because if I'm just some random college student and I'm on facebook and I want to talk about my depression issues where I want to talk about my anxiety issues, I want to talk any flaw that I have right? I'm in a fairly consequence free environment. Right? I probably have loving people around me and they just want to help me and and that's awesome. Yeah,

Ryan Rutan: there's also an emoji for anything you might be feeling at this point. So oh

Wil Schroter: my God, yeah, I'm good. I'm covered. I'm in a safe place I think. But if I'm the ceo of a company, I don't quite get the same latitude why? Because I'm still a regular person, but my words have true consequence, right? Our stock price could change based on what I just shared, our employee morale could change. A venture fund might not, you know, invest in our company. There are there are real consequences to showing

Ryan Rutan: your flaws, right? This daytime drinking thing that I just can't seem to get under control,

Wil Schroter: you know, and ends poorly. For example, mental health has been brought to the forefront of the of the startup discussion and narrative is incredibly powerful, you know, I for one, a huge proponent of people getting in front of it. A lot of the stuff we've talked about on the show has been about how mental health is a very real thing. Physical health, you know, Ryan, you and I've done whole shows dedicated to terrible, our health has become over, over this startup stuff, and we get a lot of fan mail, you know, people who say to us, they say, hey, thank you for talking about that,

Ryan Rutan: because thanks for bringing it out. Yeah, Right. Yeah, I think it's it's interesting too that, you know, we've always been called crazy, right? As entrepreneurs and it's found, but now we get to be more specific about exactly why, and I think that's I think that's that's really powerful,

Wil Schroter: we get to talk about the meds that go with it and look, this is part part of my language here, this is a fucked up experience that we go through, right? This is a crazy traumatic experience we go through as founders. There's no cool version of it, there's some highs, there's mainly lows and it usually ends poorly, right? And I just, I want to point that out because it exposes all of our flaws, you know, all of the things that that that were challenged with the most are so drawn out of us and almost impossible to ignore as startup founders. So if we have to bottle it up, if we have to hide those flaws all the time and we're this kind of mask, if you will of perfection, I don't think it ends well for us. I think personally as a founder Over the last 10 years as I've been able to be far more open about the challenges that, I have. life's gotten dramatically better, but I've also learned that it comes with consequences and it comes with a certain amount of attack that you have to employ in order to be able to share.

Ryan Rutan: Sure, yeah. How you take the top off that bottle matters a lot I think. And and you know, when and where that happens, how it happens. It's really tough because on one hand, you wanna be able to be as honest as you can about it. But not all forms of honesty are created equal, right? Like there's, it's, it's a lot of this comes down to how you say it and maybe to who and when you release the information, right? I think that there are places where it's definitely okay to be just absolutely brutally honest, you know, we see some of this stuff happen at the founder dinners that we do and that, you know, there are points there where everybody is in that environment, they feel safe, they know they're surrounded by peers. They all operate on the assumption that this is going to stay within these four walls for that evening and forever. And so you can see people kind of crack the shell, open, open the armor and and let go and that's an okay place to do that, right, twitter. On the other hand, maybe not the right place for the full on brutal, unfiltered honesty. Again, depending on what it is, I think the other thing that's always interesting to think about for me is why why am I why am I releasing this? What am I just, am I letting go for the sake of letting go if that's the case doesn't really matter what the audience is, right? Am I seeking help if so, am I seeking it in a in a healthy way or am I just throwing it out there? Because I'm I'm afraid to be specific about it and I just want to kind of throw it against the wall and see what sticks. So it's always interesting to me as I think about when I want to make my own personal renovations, why am I doing it and why in the way that I'm doing it. I think there's there's a lot to unpack there and I think it tells you a lot about the issue itself in terms of how you decide to put that out there for people.

Wil Schroter: Yeah and I think that let's let's set the stage here. You know, maybe Ryan, why don't we talk about, why don't we just go in full on admission mode about what some of our flaws are. Just so we can talk about historically how we've talked about them. You know T. L. D. R. On that. It worked out pretty well. You know I think so I'll bring this up to you to kind of kick it off a couple months ago. I was dealing with this this huge issue. We did a whole episode on this where I had this this really weird bizarre condition called trigeminal neuralgia which is a nerve issue. It's it's considered one of the most painful afflictions you can have. And I'm here to tell you that's true.

Ryan Rutan: 2nd only to starting a company.

Wil Schroter: Yeah second only starting company. It's a condition where the nerve fires inappropriately in your head and makes you feel like your head's going to explode all the time.

Ryan Rutan: Wait is this trigeminal neuralgia or is this starting a company? I love that.

Wil Schroter: It's actually exactly the same and kind of hard not to bring up right? I mean you can't see it right unless you see me wincing in pain and crying on the floor, right. That part, you'll notice which you have what you have, but where I get anxious, where I was anxious when this first all started happening years ago is I didn't want that to be a distraction. I didn't want it to be like, hey, we've got a whole team of people that are relying on me for a paycheck. I don't want them distracted by whether or not the Ceo is going to curl up in the fetal position and cry and not do his job. Is that the right answer? Probably not. But that was what was going through my head. I mean, I didn't realize you could open up about your issues. I just thought you, you talk that way down. You don't talk about it and you go figure it out at home. Yeah. And, and, and, and I would by which you mean by yourself at home. Yeah, exactly. And I would come to learn later that that was, it was an old truth. You know, I think that used to maybe be the case and it was probably flawed back then too. But we live in an environment where there's far more acceptance, not all the time, but you know, I think more so than ever in history Ryan when I brought it to you and Elliot and you know, the different staff members at the time, I got full support, but more importantly, everyone started to understand, hey, there's gonna be some challenges, there should be some points where will can't talk and we won't tell him, but we're actually like that part. I

Ryan Rutan: want to touch on something you said because I think it's, I think there's an important kind of secondary factor here and it's, you know, you said that we're in a kind of a more tolerant environment now and it's okay to talk about it. I think that one of the challenges in the past was because there wasn't enough information about any of these topics in general, even if you brought it up, the person on the other side of the table could do no more than maybe listen and and not even have a good understanding what you're talking about. And so I think because we're in the information age now, for better for worse, we have access to a lot more of it and were armed with discussion points were armed with some knowledge. Hopefully. So I think it's easier to find somebody who can actually listen and then, and then respond in a more meaningful way. Right? If you have no context for what that person is talking about. Even if you wanted to help the most you could do was listen and I know we all, we all know that listening can be a good thing and sometimes people just need to get things off their chest. However, when you're, you're exposing an issue and you really do need help or perspective or feedback if the person on the side of the table has no context of information, it's really, really hard to be helpful.

Wil Schroter: That's a really good point man. And if no one shared their flaws before and you haven't seen a successful full, you know, go around of I shared my flaws, everyone was cool about it, okay, maybe I can share my flaws too, then nobody is going to step in the ring first. The incentive is definitely not there and the reward, if you can call it that nobody's ever seen it before, you don't know whether there will be a reward. You're

Ryan Rutan: you're literally jumping off into the abyss and you have no idea if you're going to land soft or land at all or just be ridiculed. Yes, I think that we're in an environment now where it still takes bravery to do these things, but I think that the barrier that you have to cross is significantly lowered at this point.

Wil Schroter: My list goes on infinitely, but I'd be curious as to what comes to mind when when you think about, you know, some of the flaws your may be hesitant to bring up, but did and whether that worked for you.

Ryan Rutan: Yeah, so, you know, and I shared a small anecdote, a couple of couple of podcasts to go on this, where it was pointed out to me that I was far too critical of other people and that I was far too hard and pushing people far far far too hard. And then I was justifying that by saying, yeah, but I'm pushing myself harder and and that that just really didn't matter at all right. The fact that I was holding myself to a higher standard didn't mean that I was I was holding them to a fair standard. This is an interesting case study because then as I took the information in about this, it opened up another flaw which is at that time I was not good at taking feedback. Right? And so, you know, I'm hearing about one of my flaws, but I'm incapable of absorbing information in the right way because I wasn't used to taking feedback in a constructive way and and doing something with it. I would I would become defensive and in some cases like exactly in this case when when my coach came to me and said, hey, you're pushing the rest of the team too hard. All right. My response was attacked to defend. Yeah, but I'm pushing myself harder. Right? And and so they're sort of, you know, I guess you could probably pull that out into three different flaws. one I was being too hard on others too, I was unwilling to take feedback for myself and three when faced with feedback rather than absorb it. I was I was attacking to defend, which I would I would even throw in as a separate, separate Flom. It was the second one of those, right? Which was the ability at some point to absorb the feedback. And I realized that there were still points where I would attack to defend despite that I would at least take the feedback to heart and sometimes it would take months or a year or more to really do anything about the feedback. But it was there, but I didn't completely let it let it roll off. I didn't, I didn't, you know, put on the teflon and and just, you know, completely ignore the feedback. But those were some big ones and I remember going to a couple of early, early mentors, one of my college professors who turned out to be an excellent mentor for me and asking like, you know, how can I be better at at receiving the feedback? And she gave an excellent piece of advice which was take it to heart, but take it for what it is, right? They're not attacking you, they're not trying to prove you wrong, they're not trying to denigrate you in any way. They're probably trying to help you write even if that isn't their intention, you can take it that way. And that was really powerful for me to to hear that. And that really helped me get past that one. And so I just started to look at those pieces of feedback, whether they were delivered well or not as gold nuggets that I could use to improve myself, improve my processes. Um and I think I'm much better at it now. There's, there's still times, you know, where like you're already having a bad day and then somebody, somebody says something about, you know, something you've done or something you haven't done and you can take it the wrong way, but I think I'm far better now. What kind of leaning back and taking that feedback and what a game changer that is right, because if the only feedback you ever get is from the echo chamber in your own head, good luck, right? I am never going to be smart enough to figure it all out, right, that's what the rest of the world is here to help me with.

Wil Schroter: You know, I think with something interesting about what you said though, Ryan, how you responded to that feedback, how you responded to how you present your flaws, so to speak is so characteristic of whether or not this is going to work well for you. For example, if I present my flaw and I've got this mentality that how dare you question my flaw, right? You know, I'm going to present it, I'm going to express my vulnerability, but if you, even for a second, don't respond in the way I expect you to shame on you, you can't attack people with your flaws, right? I have crippling anxiety, right? And Ryan, you've dealt with me for so long. It's a total joy, right? But everything freaks me out all the time and it has its moments, right? If I admit that to you that I would have to for a second, it's very evident. But if I were to admit that to you, Ryan and you were to say, well you really have to do something about it. In my response was some version of, well, you know, again, part of my friends go fund yourself like Ryan, how dare you attack? Look, that is the wrong way to admit your flaws.

Ryan Rutan: Of course it is man. All you have to do in that moment is have a panic attack and then

Wil Schroter: I'll never bring it up again and be like,

Ryan Rutan: let's just don't trigger

Wil Schroter: him. Okay, just double back

Ryan Rutan: slowly and leave mountain dew on the table and be fine.

Wil Schroter: Look man in from, from my standpoint, when I present a flaw, what I wanna do is I want to show vulnerability and I want to show honesty. People generally don't lie about their flaws. We lie about everything else. Everything else gets exaggerated but our flaws, we tend to keep pretty close to the vest,

Ryan Rutan: I may have lied about my pool shooting capabilities more than once in a bar in order to win some

Wil Schroter: money. But yeah, you're a hustler, right? So when I look at the ability and advantage, let's say to share our flaws. Here's how I look at it. Number one, I think it's one of the most powerful ways you can connect to other humans. I don't think the old school Gordon Gekko version where I'm supposed to show everyone how I'm perfect at everything. And I'm kind of, you know, the master of the universe, those days are gone, right? If you're trying to pretend you're that person, people don't even believe you anymore, right? The world is has gone past that now. That doesn't mean we have to go into full therapy mode with our entire staff, right? Was showing everything. But I think there's a lot of benefit and being able to show the folks around you that yeah, I've got some challenges to write, I don't need to put on this perfect persona. I'm dealing with crazy stuff every day. I think opening up is a powerful dialogue because here's here's what it is. And Ryan, you know, I've talked about this and I love this part. It gives other people permission to open the kimono as well. Boom,

Ryan Rutan: and that's the big piece, right? And I think that that's, you know, it's it's even even if we're not talking about deep character flaws, like even just making small mistakes, like, oh well I made the wrong decision here. I went the wrong direction with this. I didn't think about that and I should have, that gives everybody else permission to make mistakes because regardless of whether we give them permission or not, they're going to make mistakes, right? The difference between having permission to make mistakes, the permission to be flawed and not is simply how they'll feel about it because they're gonna then have to feel like they hide them, they're going to bottle them up, they're gonna push it down, it's going to affect their performance, is going to impact their relationship with you with the rest of their colleagues and it's gonna close the door on honest conversations that you could have had to help them improve their performance and or in the worst case where they're actually going to hide things from you that may be critical to understand in order to, you know, run the company or or at least have them perform the way they should.

Wil Schroter: How about this? So I've been very explicit about my anxiety. I've got A. D. H. D. Which triggers anxiety which just simply means I freak out all the time about everything. Uh and puts me in kind of red alert mode all the time, not awesome by the way, there was a time and a place where it was kind of like nice, like it gave me a superpower, kind of founder thing and now just as a parent, it's just not paying any kind of dividends and and we'll talk a little bit later about not just how I handle it, but how I explain and show the progression for that flawed and why that, you know, that's important. But here's what's interesting ever since I kind of got front and center on that and I, and you know, I've written articles about it, Ryan, we've, we've done, I think a show about it, here's what happened. Our staff comes to me now and they say, hey man, I gotta tell you, I've just been doing some crazy anxiety and then here's what's awesome, they know that I understand, but if I were to go back 10, 20 years, No one would have come to me with that, right? No one would 20 years ago at Blue Diesel, the agency would have said, hey, well can we sit down, I'm having a really tough time getting this client worked on because my anxiety is just firing like mad, it would have been true and I could have helped them at so many levels and it would have never come up because I had never established an environment where we can talk about our flaws so we can actually work through them, which I think kind of brings us to the next point, Ryan, which is how do we talk about how we're working through them, sharing your flaws is the easy part relative to it, How you share them in the path you used to say, and here's how I deal with it is kind of the more important part of this and I think this is the heart of the discussion.

Ryan Rutan: Sure. And and I mean this is yeah, this is the heart of discussion, This is the most critical piece because if all you do is expose the flow and then you don't talk about doing anything about it. I mean the worst thing to do would be to say nothing right. I think you can also overdo it and, and just become manic about it, right? But I think that you do have to address the fact that, you know, here's, here's what I'm doing to solve this or here's what I did to solve it, right? And certainly we can, we can look at some of our flaws and say, hey, we're actually on the other side of this now and that's great. But there's certainly flaws that, that we, that we still go through, I still have flaws, patients being one of them, although it's getting much, much better with Children, I have so many more opportunities to practice it and the cost of getting it wrong is so much higher. And yeah, so yeah, this is, this is an absolutely critical piece of this. So what's worked for you in terms of getting the conversation right? What's enough? What's, what's too much

Wil Schroter: in my mind. I try to get to the point and I sometimes even lead with this, which is, hey, you know, let me tell you about something I wrestle with all the time, but for what it's worth, Let me tell you about the hack that I use to get past it, here's how I manage it, right? Again? I spent a lot of time over the years talking about anxiety mainly because every single founder has it and it's one of those topics where a lot of people are afraid to talk about it, but it's like I already know you have it. So let's talk about what to do with it. It's kind of impossible not to, Here's how I like to frame these things again, I'm going to go back to the article that I wrote, how I harnessed my insane startup anxiety. Think about what that article implies, how I harness it. In this case, the article, you can google it or you can look at some of our past podcasts. Talks about, I have insane A. D H. D. Like off the charts. Bad. However, there are actually some advantages to that. It also puts me in modes where I have like super power mode where I can get through huge problems really quickly but it comes at the expense Of being up at 4:00 AM working on a problem that doesn't actually matter like a lot. And so I talk about all the different methods I use to manage that anxiety. Everything from some of the supplements I've taken that have actually kind of made it go away to the extent that it can which has been amazing and life changing to some of just the mental models. I used to kind of like compartmentalize anxiety in a good way to say, is this is this problem really this big, what's the rubric? I'm going to run it through to to size the problem before I artificially freak out about it.

Ryan Rutan: I think I went years with, with anxiety and I was calling it something else. I think even just like being able to put the right finger on it helps a ton. So for me it was I was over analytical, right? I was an analytical, I wasn't worrying, I wasn't, I wasn't, I wasn't anxious. No, of course not. I was over analytical and I worked to solve that particular problem I think had I started calling it anxiety, it might have been a bit easier than I could have, I could have found help faster. But for me it was, it was similar what you described, right? There were some mental models that I used and they were pretty basic, right? I would find myself up at night rethinking the same problem for the 4th, 5th, 6th

Wil Schroter: time

Ryan Rutan: and I would finally, what finally just ended up working for me was I would I would say, okay, look, 1st, 1st decision. Is this really a problem or not? If yes, am I actually going to do something about it or not? Right, and these are just binary gates and I'm having this conversation with myself, so of course I can, I can lie to myself and I can, I can, you know, continue to worry about it, but for me it worked pretty well, I would go through this little little little routine of is this really a problem? Yes, okay. Am I actually willing to put in the time to do something about it or am I just gonna spin my wheels worrying about if the answer was yes, then what am I going to do about it? And then the thing that I found was just writing it down, just grab a notebook beside the bed right down here are the steps I'm gonna take to solve this problem and then and then somehow that that sort of just put a bow on it and I no longer needed to feel that anxious about it. Of course mileage varies, certain issues will come back and haunt you, but it's simple things like that, that, that have kind of gotten me through some of these bigger issues, the solutions are actually quite small

Wil Schroter: for it's not just the fact that you have the solution, which is awesome, it's the fact that you can communicate it because here's the thing, I think there's two parts of what you just said, I think the first part is admitting that there is an issue, a sense of self awareness, right? If you're just a complete jerk to your employees and you showed no sense of contrition or self awareness, right? That is so painful, right? If you were to say, hey, you know, sometimes I'm probably a little bit much to deal with. I tend to get over

Ryan Rutan: analytical, that's

Wil Schroter: Part one. At least your people can see, Okay, like by the way, everyone else already sees it, everyone else has already prescribed.

Ryan Rutan: That's the thing, right? That is absolutely the thing.

Wil Schroter: What matters, especially as leadership is that you prescribe it right, you know, on your own volition. So I think the admission goes a long way to making people say, okay good. They've got a little bit of self awareness here. Cool. The second part is that you're actually willing to do something about it. It's one thing to say, hey guys, I know I have this huge problem, but if if the follow up is just deal with it, right? That's not exactly what people want to hear. If you say, hey, I've got this huge problem. I know it affects you, which show some empathy, I know it affects you and here's what I'm doing about it. Let me give you an example of where somebody didn't do this About 15 years ago. I get a call from an employee, a good guy and he said to me, he said, Hey, well can't come in today and I said, Oh man, you're doing okay. And he said, yeah, you know, from time to time, I'm just kind of not feeling it. And uh I just don't like to work. I was like, wait, what I was like, I was like, okay. Uh

Ryan Rutan: He thought he was living in 20

Wil Schroter: 20. Right? Yeah, right. No, it was, it was I was so taken aback by it. I mean, I've had thousands of employees. So I, I've had, I've had a lot of shots on goal in this, that I hadn't, I hadn't had one before. Now again, bear with me on this, the backstory is he actually had severe depression issues. I was not aware of, which is sort of the point here. Later on, we'd come to come to kind of unpack this a bit. I kind of leaned in and said, hey man, if there's something you're dealing with, like let's work on it together. And eventually he opened up, he felt really good about it and we got to a great place. But here's why it broke. He had an absolutely legitimate reason for not coming to work. But if you don't present it as such right? If you just present the outcome, hey, I just don't feel like coming to work in his mind. He just assumed I understood why. Like he assumed I understood the flawed and would just put the pieces together clearly. I didn't. And so I'm just gonna respond as wow, that's a really irresponsible thing to say what the hell just happened as founders as managers as executives, what have you, we have the same responsibility, right? We may not be reporting up to a boss, so to speak, but we have the same responsibility. It's incumbent on us to be able to say, hey, I'm acting a certain way or I see a certain outcome that's being driven by me man, that's on me. I'm kind of shitty at this. But now, normally just admitting, admitting it's kind of the easy part here. Here's what I do about it. One of the things often that I, I tell you know, you Elliot or anybody else's, if I get to this point, run the signal flare up, tell me Hey will like, I think you're kind of going to crazy town right now, right? Like settle down and that's a checkpoint for me. It's admitting my flaw, giving the people around me a safety valve, right? A safe word to be able to say. Yeah. And so it puts us all in a great position. It allows me to get my flaws out in front of me to kind of create my own guidelines and it allows the people around me to feel safe to operate in an environment where my flaws aren't just this nuclear attack.

Ryan Rutan: Alright, so we've given a lot of context around when and how and why we should share these things. But is is there a point? This is my chance to speak french now, Is there a point where we should just shut the funk

Wil Schroter: up? Yeah, there is actually, it may be the future that we're living in now, but there is still a time and a place for all of this. So let's, let's kind of map that out a little bit because I don't want this to turn into, hey Will and Ryan said it's a good idea for every founder to just kind of like puke at the mouth, every flaw that they've ever had. It's not always a good time.

Ryan Rutan: I don't want, I don't want to get that email from anybody. So listen to the podcast, went to our board meeting and uh, yeah, they've, they've removed

Wil Schroter: me. Well actually, I love that scenario because let's say that that scenario existed. I mean, I'm gonna, and I'm gonna bring in a bit of a tricky problem to address. Let's say kind of like the, the employee that I was talking about before as a ceo, I've got a serious, serious depression issue, right deal a long time. I've kind of, maybe I've mastered a little bit up to here and it's kind of, you know, welling up inside and I've got a board meeting, I've got venture investors and during the board meeting you slide 10, I bring up, Listen guys, just something I want to get off my chest, I've been dealing with some, you know, pretty crippling depression and I really just want you guys to understand they're with me on this. There's a chance that it goes totally well that you have these really well meaning really well understanding board members and they sit down with you and said, hey, we get it. That's not the way to do it, right. What you don't want to do is present this in kind of this big fanfare. If you will not knowing how people might react, expecting them to react exactly the way you want them

Ryan Rutan: to. Yeah, you're sort of forcing them into a particular reaction whether they want it or not, which is in that moment, they're going to have to kind of swallow it right? And I don't think that's ever a good position to put people in because they may not feel like they can be as honest as they want to in that moment,

Wil Schroter: which yeah, not healthy for anybody. People may not react the way you want them to, but you have to consider the moment of delivery. If I want to deliver that same message, I'll pull each board member aside one at a time and explain it to them. I won't throw it as a hand grenade into the room and hope it goes well. Right,

Ryan Rutan: Well, this may seem obvious, but if you are reaching out and wanting to be honest, would you not want to do that in an environment where the person you're presenting this too can be honest in return. And if you're not, then I would go back and ask yourself, why the hell are you doing this in the first place? It doesn't make any sense at that point.

Wil Schroter: Absolutely. You know, the same goes with with putting on social media. That might not be the best way to present it

Ryan Rutan: tangle your board members.

Wil Schroter: I mean I just

Ryan Rutan: like you're not coming in today, cheers.

Wil Schroter: And honestly, I see that a fair amount. I see people like kind of, you know, come out so to speak with whatever issue they've got on social media and just kind of just shotgunned into the air and say, hey, let's see how this goes

Ryan Rutan: now. So hang on, hold on that one for a second. Because I think there's, there's, there's some interesting stuff there. Why do you suppose they're they're doing that? Do you think that the, the supposition is that by putting it on social media, I'm getting it out there, but I'm also buffering it a little bit that this softens it somehow, that, you know, people will be kinder if I do it here as opposed to doing it one on one. Is it that we're trying to force a particular reaction again? Is that why they're doing that?

Wil Schroter: It could be a number of reasons sometimes people do because it's convenient give an example like, uh, when I had to go in for my fourth surgery for this trigeminal neuralgia issue, I posted it on facebook a couple months ago, mainly because by that point I had been dealing with it for so long. I figured most people already knew what I was going through and for all our staff members and stuff. They kind of knew what was going on and I had mentioned it on multiple occasions, but like I was just like, this just be an

Ryan Rutan: easier way to kind of get, definitely assumed that people had some context because what you said was brain surgery tomorrow, See you later.

Wil Schroter: It

Ryan Rutan: was, that implies some

Wil Schroter: understanding. Yeah, yeah, yeah. Um, but to be fair in retrospect, would I have posted that again? Maybe? Maybe not, there happened to be a weird silver lining to that. It turned out like three or four of my friends had the same condition, which is so bizarre because it's such a rare condition and I actually helped a couple of them get treatment that they needed for like what's essentially a debilitating condition. So you know, silver lining. But that said, in that case, I had already communicated to the stakeholders that I needed to communicate to that I was concerned about. And so this wasn't like a hey Ryan Elliot rest of management team, by the way, I may never talk again like, oh, I read it on social media, not appropriate by that point, I had long conversations for years with the entire staff. So kind of people knew what was up and anybody that was learning for the first time, it was okay if they didn't actually know, but let me give you a different context. I'm crazy stressed out, let's say two years in companies, almost out of money. I don't know if I can make payroll and I decided to share my stress at lunch with my coworkers. Guys, I gotta tell you, I am so stressed out. I have no idea if we're gonna make payroll again, totally true, totally honest. Probably not, probably

Ryan Rutan: not the right time to bring it up. Yeah. Who would like to buy my lunch today? I've already maxed my personal cards. I'm not planning on paying any of us next week.

Wil Schroter: I gotta tell you this isn't about being dishonest, it's about being appropriate, right? We have to understand that, that as leaders of an organization, it is incumbent on us to find the right time place and presentation of our flaws in a way that other people can understand, respond to, you know, in a, in a reasonable manner and work through with us. We can't just say, I'm feeling it today. Everybody hear it. Let's see what happens

Ryan Rutan: right now. It's so, and, but yeah, so the, the follow on to that is have a point, right? This was, this was something that I learned from watching planes, trains and automobiles. Uh, steve martin points this out to john candy at some point in a very nice way. But he's like, you know, have, have a point, if you're gonna tell the story, have a point. And so I think that, you know, this is, this is critical as founders that, you know, if we're just going to dump this out there, going back to the example that you gave earlier, right? If if you're if this is impacting their work, right? If they're having to deal with you as being an aggressive boss or a depressed boss or a super anxious boss or somewhere this manifests for them as as a negative right there. Having to deal with with some manifestation of this problem then talking to them about it makes sense, right? If you're just looking for feedback, that's okay too. But think about what you're gonna do with the feedback, why and whether they're the right audience to seek it from or not, right? Have a point understand what at least you think the endgame is before you begin this conversation, I'm not saying over analyze it and make sure and game it so that it comes out the way you want it, but at least have some idea of what you hope the outcome to be. We don't have the conversation yet

Wil Schroter: correct. And from my standpoint, I straddle this line, Ryan when I talk about this subject with founders because on the one hand, I don't want to prevent people from sharing issues, especially if there's something, you know, really bubbling up, you know, when we get into mental health issues, sometimes these things take a dark turn and I don't like anything that would prevent people from sharing early so they can kind of get the help that they need, right? So that's on one end of the spectrum. On the other end of the spectrum is, I just don't really consider some of the responsibilities that I have and I just kind of get puke everything on social media and assume that's just going to be okay and it should figure itself out. The world is just not that simple. It doesn't work quite that easily. Where possible. I like this measured approach in between. I like being vulnerable. I like sharing my flaws. I like the honesty that comes with this, but I like it in a package where I'm delivering it to people to show that I've got a responsible manner that I'm dealing with these flaws.

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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