Startup Therapy Podcast

Episode #89


Ryan Rutan: Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan joined by Wil Schroder founder and Ceo of startups dot com and good friend of mine as we've established many times. Well, does anybody ever really understand what it is that you do?

Wil Schroter: That's such a loaded question. I mean, as being a founder,

Ryan Rutan: you're welcome. Yes. As a founder.

Wil Schroter: No, never. I don't. I mean, come on man, how ridiculous is it that for as long as we've been founders, I don't think there's ever been a point where anybody actually understands what we do. In fact, actually, now that I think about my career, started that way In, in 94, going back and back to the future, right in 94 I was dropping out of college and I was so excited about it and I went to my guidance counselor and I said, I'm dropping out of college to start an internet company and she was mortified. Like in her mind, like, wait, well, hold on back up, back up, you're dropping out of college, What's wrong? And I was like, I was, what are you talking about? I'm going to start an internet company and I'll never forget her words. She looked at me deadpan and she was like, what's the internet? It was such a perfect opening to this movie. That would be my career because it was the beginning of me realizing that no one would understand what I was about to do or at the time understood what the internet was.

Ryan Rutan: Sure. Yeah, I mean it was, it was a weird time, but I don't think it's limited to the internet, right? I think all founders, whether you're online, offline face this to some degree, and they're just like, unless you're talking to another founder there, just like, I have no idea what you're talking about, and maybe even if I have some idea what you're talking about, they really don't have context for what we do or what we go through to do what we do.

Wil Schroter: It's always the same routine. It looks something like this. I'm at a cocktail party, I'm at a family gathering, I'm gonna barbecue some social event where there's just not founders there and a buddy of mine walks up to me or a family member and said, so, how's the startup thing going? And I'm like, oh God, here we go. And I'm like, you know, it's going well and it's typically not going well, but I said it anyway, it's going well, you know, we're growing and we just hit this milestone and this thing happened. And like as soon as I get five seconds into this explanation, their eyes just rolled back in their head and they just like, die for a minute. There

Ryan Rutan: more glazed than the ribs on the barbecue. Oh my

Wil Schroter: God. And I don't know why, every time I try to explain what I actually do, what's actually happening because never in the history of that explanation has someone said, oh, wait a minute you're raising around what kind of valuation you're looking at no cost whatsoever. And so About five seconds in I realized that this explanation is about to be hopeless and I just switch it to things are going well with the computer business or whatever. My alibi for what I actually do when you explain it, how many people would you say actually understand what you do?

Ryan Rutan: Oh outside of the founder space. Um There are times, you know, there are times where if they have some context for what we're doing, right? Like and this is where it takes a lot of work actually. And you know, I've said this on the show before, I'm a big fan of this phrase, communication is the burden of the center. So in the times when it's worked, it's somebody that I'm talking to I know well enough to know that there's like some topic that they're interested in. Maybe it's you know, maybe it's I don't know, just wellness and so I'll be like, well, you know, things are going really well, you know, we're actually working with a really cool client right now that's trying to raise money for this wellness business. And so like there's some tie into what they're doing, but it doesn't really give them a sense for what I'm doing. It's really just an end around to not having that same shitty conversation that you were describing above. It's just a way to like be able to talk to them with some tangential connection to what we do, but it's directly connected to something they care about and it's the only time it works,

Wil Schroter: I think it's worth us digging into this today kind of this concept of why doesn't anyone understand what I'm going through? If it's a new founder getting into this, you're probably wondering this more if you've been at this for a minute, I think you'll just laugh through this episode how familiar this all sounds. But I mean at its core, what I would say, Ryan is what we do makes absolutely no sense to a sane person, correct? If you were to compare the expectations are of the same person versus what the expectations are for us as founders, what would you say are some of the big, you know, points of delineation between those two. Well,

Ryan Rutan: I mean, Dude, I don't know, like to throw a dart and you're gonna hit one. Um like, I don't know, just like getting paid on a regular basis. Um you know, knowing what to do at any given moment. Um, not having to change what you're doing every 3-4 minutes. Um, you know, not being responsible for literally everything. Uh there's so many right? There's so many, like, it's really funny, but if you, if you bucket all of the, the sort of job criteria that we have, if you can even call it a job, no sane person would accept that and be like, hey, we have this position, we're offering this, this, this, this, this, this and this and again, like a sane person would be like, you have your mind like, no, I don't, I don't want to do that. I don't even really understand what you're talking about.

Wil Schroter: Ryan, Imagine this were a job interview and you weren't 100% sure what the job was. The person sitting across to you is, you know, typically an entrepreneur themselves pitching you the excitement of this job called the founder and they say to you, okay, this is going to be wonderful. We want you to work on a product and you're like, well, what is that product is, well, we have no idea now and we want you to sell it to a customer. We'll who the customer be. We have no idea, right? And we want you to hire a team. Well, who would that team B and what they do? We have no idea. Okay, Do I get paid for this? Probably not. In fact, you'll probably have to clear out your life savings for this job. Just pay us to work here. Oh my God, it just compounds and you'll probably have to work twice as much as you work for any other job while you're doing this and you'll probably lose all of your relationships and probably, you know, ruin your health. Who would take this job. That's exactly what we do. That's literally the job that we signed up for its bananas,

Ryan Rutan: which is funny cause I'm thinking about it now if I was interviewing somebody for that and they said yes to it, I think I can't hire you. You're nuts.

Wil Schroter: Yeah, exactly. Who would take that job? And so that's essentially the point of reference or the context that our friends are using that our family is using. You know, there's like in their minds, you go to a job, you have a very specific track for how you advance for when you get paid. I mean when you get paid seems obvious you obviously don't pay money to work. That doesn't make any sense at all. You know, that's called college and like in so on and so forth. All of these things would make no sense to a sane person. And yet here we constantly try to describe what we do with so much enthusiasm that we can muster to these people who just look like give us 1000 yard stare, right? I don't know why we're surprised.

Ryan Rutan: I don't either. It shouldn't, it shouldn't make sense to them, right? It barely makes sense to us and we're on the inside of it. You

Wil Schroter: know what? It's just something funny. Just

Ryan Rutan: a side note here. This is a conversation that's come up a couple of times in the last few weeks as I've, as I've had the opportunity to hang out with some, some folks who are visiting from various different parts of the world and it came up twice specifically because I didn't ask them what they did and they were like, hey, you're an american, why didn't you ask me what I do? It's a uniquely american thing where we tend to ask other people like what do you do? Like you asked the european like, so what do you do? Like what do you mean? I'm drinking wine and eating cheese. I'm, you know, being european, that's a poor characterization of what Europeans actually do all day. Um, but since we're talking about being misunderstood, I feel like that's a fair job. You know, they're like, they don't get it, they're just like, you know, they don't think of and we, this is, you know, harkens back to the episode where we talked about, you know, you aren't your startup, they definitely don't see themselves as a function of what they do for a living. Um, so this is also this kind of weird, uniquely american thing where we asked people what they do and I'm just beginning to wonder like does anybody actually really care? Like we ask that, but is it just for lack of a better question because nobody really seems to care. Like even, I've watched accountants explain what they do, which isn't hard to explain, right, People still aren't interested.

Wil Schroter: It's

Ryan Rutan: boring, right? So like why

Wil Schroter: are we even asking this? But that's the difference. I think when people ask us how it's going or what we do, we expect them to have context for why what we do matters or why anybody would care. And we're so fired up about it, you don't get into this business because I guess I have nothing else to do. So I guess I'll start a company like there's no version of that job interview that becomes your first choice if you're not terribly motivated to do it. Right? And so I feel like for for how we have to present ourselves or can't explain ourselves if we don't understand the audience, you know, similar to your explanation of the Europeans. If we don't understand our audience, we're just constantly shaking our head. Now there is an audience that understands us and that would be other founders. And yet, and yet most founders aren't having those conversations, aren't seeking out those other founders, Like when you talk to folks say from that are maybe interested in a founder group or something. Where do you tend to see a founders call it? Circle of influence, so to speak, especially in the early days

Ryan Rutan: circle of influence. You mean the people who they are already interacting

Wil Schroter: with on a regular?

Ryan Rutan: Yeah, it's it's it's not a big room full of founders. Unfortunately. I think there's a couple of reasons for that. Actually. There there there there are a whole bunch of reasons for that. 1st. I think that just it's not a natural behavior to just seek out another founder. Maybe not even know where to find them necessarily. And founders all tend to be busy and I'll tend to be doing crazy stuff and like it can be, it can be a little difficult right to kind of wrangle them, but they tend to just, they default to whoever they were already talking to before they became a founder, which is a little bit dangerous, right? Especially if you're trying to share and get real feedback or, or true empathy or anything like that. Right? So they're, they're talking to their family, they're talking to their friends, maybe ex colleagues from the company that they left college roommates, whatever. It's not an audience that is going to be able to do much more than not along and hope that you stop talking sooner than later. Right. The other reason I think that this is tough is that we have to remind ourselves that in going back to your point that you've got to be, you know, you're a different kind of person if you're gonna end up becoming a founder, there just aren't that many of us alright. If you look at it percentage wise, there just isn't a huge density, right? I mean, if all you're doing is thinking about the start because you know, like, oh, there's tons of startups. Okay. Yes, I agree with that. If you aggregate them all, that's true. But look around at your friends circle, you know, especially before becoming a founder. How many of those other people were founders? In most cases, it's, it's zero most people before they became a founder knew, Let's say somewhere between zero and 1

Wil Schroter: founders, right? Well, it is, it's not a career

Ryan Rutan: have access to that, right? It's not a career,

Wil Schroter: right? Or

Ryan Rutan: they don't recognize them. Is that the other thing that I think happens, and this is this is this is really a pity is that I think that the, the early and the first time founders are quite intimidated by people who have been at it longer, not knowing that we're all still making the same mistakes and screwing up the exact same ship that they are, we've just been doing it longer. And so I think that there's, there's some sense of like, I want to keep this a secret from other founders until it looks right, and it's perfect. And it's, it's the ugly baby thing, right? Nobody wants to put the baby out there and have somebody go, that's a stupid idea. Especially somebody else who has the context for it, right? Sure. I don't care. Hearing that's a stupid idea from my uncle because he's stupid. It doesn't matter to me. Um, you know, but if I throw that out to another found and they're like, that's a dumb idea. That's gonna, that's gonna hit pretty deep, whether it's true or not, I'm going to carry that around with me for a while.

Wil Schroter: We'll also, it's not a matter of the fact that founders only understand each other. No one can possibly grasp what we do. But I think what we're really talking about is they don't appreciate What we're going through. And I'll give you an example. I've got a good friend that I've known for maybe 20 years and about 10 years ago. he joined the special forces, which I genuinely appreciate from defending our country. And every year when he comes back from tour, uh, he comes over and we barbecue together. He actually also happens to be an amazing cook. And uh, and we sit and we bullshit about, you know what he's doing and everything else like that to the extent that he can explain it. And every time the same thing goes through my head, when you explain to me What you're doing, I get it, you know why? Because I've seen a bunch of 80s movies and I know exactly how this goes. I saw commando

Ryan Rutan: Rambo, commando.

Wil Schroter: Yeah, that's exactly how it goes Right in my small mind. I've got to imagine as he's explaining it to me. And I'm, and I'm asking all these questions I was asking a million questions. It's fascinating. And I'm asking him all these questions, he's thinking, yeah, you don't really understand what I go through, right? Like I get that he's, that he gets shot at, except he's been shot at gets much

Ryan Rutan: pretty significant

Wil Schroter: difference there, right? I think that my friends that aren't founders understand some of them what I do, but they haven't felt what I do, right? They they haven't

Ryan Rutan: sympathy versus empathy,

Wil Schroter: right? Yeah. Well, it's, it's difficult because it's one thing to say, I'm going to lose my job and I don't want to discount the pain of losing one's job. It's, it's, it's, it's horrific. However, there's another side of it which is to say, I'm going to lose everyone's job,

Ryan Rutan: right? That's not the Oprah moment you want and I'm going to lose my job and you're going to lose your job and you're going to lose your job and you're going to lose

Wil Schroter: your job, right? Like if I work at google and I screw something up and I get fired, that sucks my my life is in a tough spot, right? Again, not discounting that. But if you're running google and you screw everything up and run style and you lose everyone's job that's a little bit bigger for pressure. Like that's not quite the same for a lot of people. Yeah.

Ryan Rutan: And not just but so like, so, but think about that. I mean, so yes to the team, I mean, just and then of course you are using a very big example there. But imagine what happens because that's an entire ecosystem, you're talking about that company fails, a whole lot of people feel that, right? It's not just the employees, all of their customers. The stakeholders. Everybody is going to feel that in a big way, and that's a hell of a lot of pressure. So somebody who's lost their job, he doesn't know what that feels like. It is not

Wil Schroter: the same thing. And I think it's silly for us to pretend that they would write or, or more specifically, to call it, scold them for not understanding. I think the core of what we're saying today isn't kind of what we're getting to the meat on, is it's not about saying, oh, woe is me. People don't understand me. It's about zooming out of touch and saying why would they? Right, right. And, and just be able to say, okay, I get it. No one's really going to understand what I'm going through sands, maybe some other founders, but I need to kind of consider that going into this. And for a lot of folks, you know, especially people who, this might be their first startup. It takes a while to acclimate to that, right? Because you're like, okay, I had jobs before I went to college before I was in high school, before everyone understood it. It wasn't hard for people to get. Now. All of a sudden I've got a spouse that doesn't understand me, my friends don't understand me, my parents don't understand me. What the hell,

Ryan Rutan: Right did I start speaking Klingon like what happened?

Wil Schroter: And, and, and the truth is, I think this, this is where it hurt me the most. And be curious your thoughts on this, It hurt me the most because it's probably when I needed them the most. Yeah, right. You know, right. When I came home for the first time, because I was in college at the time and I lived, you know, states away and I came home for the first time and I explained to my family what I was doing, I'll never forget this. My grandmother's sweet woman was in tears and I like I came home thinking I was going to have this champion speech and all she heard was I dropped out of college, right. It didn't matter every word that came out of my mouth after that. It was, you know, some, some Klingon language, that's all she heard and that look of disappointment in her face. That feeling like I thought I was coming home showing I won the football game and everybody thought I was a total loser. Like it sucked. And when I hear founders talk about that, you know, about not being able to kind of get the support that they want. I feel it. Um, you know, what do you think?

Ryan Rutan: Yeah, I had similar experiences where there was a lot of pressure, luckily my, my like immediate family was was quite supportive. I went ahead and completed college. So I took that excuse off the table. I didn't let them be mad about me for that or worry about me for that I guess is always better. They weren't mad they would've been mad. They were worried thank your grandmother. Right? She's concerned. She's thinking you've now traded a better future for something else. Yeah I was the only kid

Wil Schroter: that ever went to college in my family so needless to say that was I became the only kid that also dropped out. So yeah

Ryan Rutan: and then I was I was getting a lot of pressure from interesting enough like from at the university a lot of the work that I was doing with the startup that I had during university was for the university building out websites databases, different different stuff for different departments as it was coming time close to graduation. I was I was getting a lot of pressure to continue on to to an M. B. A. Program. Um got some nice letters of recommendation that I didn't ask for, managed to get a scholarship to to do an M. B. A. At leeds in England and it was like this this was this big thing and I was getting a lot of pressure from from you know the the guidance counselor um who I was already making more money then and just a lot of pressure from from people and telling me that you know you're you're being a fool, you should continue this. You know you've got this great opportunity and I'm like yeah I don't I just don't want to do that. I've been doing school for a long time, enjoying the business I'm running, I'm having more fun doing this is what I want to be doing. And luckily there was one voice of dissent dr Benvenuti and I owe a great

Wil Schroter: credit. What's that?

Ryan Rutan: Yeah. You know, nearly as

Wil Schroter: well. Oh boy.

Ryan Rutan: So neely was the one voice of dissent in all of this and she said like Ryan, what are you going to gain from an N. B. A. What do you think you're going to gain from it? And I said, well from what I can garner, it's it's you know, networking connections and and and you know, a better job. And it's like, do you want a job? Absolutely not. She's like, are you going to pay yourself more if you go get an M. B. A. And like not unless I make more money, do the ambitions like you're not gonna make more money because you get an M. B. A. At your own company, it's not going to teach you anything that you're not gonna learn faster doing what you're doing. And luckily she said that at that right time and I was like, you know what, thank you. And I took that to heart and turned down the opportunity it leads and and and walked away from that and never looked back. I've never been sad day in my life that there's not M. B. A. After my name, I'm sure what I would

Wil Schroter: do. It's so interesting to me because for most founders, again, we need the support more than ever. And you know, people don't seem to understand what we're doing, but where I think the founders get held up Ryan is that they keep waiting for everyone else to change. Yes, right. Like the problem isn't that no one understands this insane thing that I'm doing. The problem is that they won't take the time to change their, their, their line of thinking. Remember they are the same ones, we are the insane ones. They shouldn't have to change their line of thinking. And I don't look at that as a way to let them off the hook. I look at it as a way to kind of give ourselves more responsibility and what these conversations are and what those outcomes are. And I gotta tell you, I specifically feel this way when people are trying to kind of bring the people that are closest to them around the corner. Right? So like for folks that have spouses that don't understand what they do. I think the idea as well, my spouse should really just, you know, really appreciate what I'm trying to do. Why would they? And again, I'm really, I'm not trying to speak to people's personal relationships. I'm saying the onus is on us as founders to translate, you know, in so many ways, right, whether we're translating to investors, what we do to employees about how stock options work. I mean you name it right? Like we're always translating something. I feel like this is no different. I feel like it's incumbent on us as founders to sit across from, especially the people we care about and say, look, I get it, I get white, what I do makes no damn sense. However, and this is kind of the turn, Here's why I do it right? Here's what it means to me. And I think that's the part that's left off the table, you know what I mean?

Ryan Rutan: For sure. You know, I think that, you know, you made a couple of good points there, you know, I think that we should be considering who we're even having these conversations with not everybody needs to hear this, right? And I know as founders were so excited about what we're doing and we're we have to be, we have to be insanely passionate that it just sort of oozes out of us and we kind of can't help it, particularly if we asked the question, what do you do or how's it going? Like we assume that that's a genuine question, right? It probably isn't and it probably at least not to the degree that which which we start to deliver information, but to your point, your loved ones, you know, the people who are around you, um, that are watching what you're going through, particularly, you know, there's there's there's there's low points where things are tough and they're watching you suffer and not understanding why you continue to do this because again, a sane person wouldn't just keep doing that. They would be like, okay, this has started to suck enough that I'm just going to stop and we just don't do that. So I think that, you know, making it relatable, making it understandable and and and really also thinking about what is it you're trying to accomplish with the conversation, right? There's a, there's a line in planes, trains and automobiles where steve martin, you know, it starts to rail at john candy and he says, you know, you have all these stories, you talk, you talk, you talk he's like sometimes have a point, right? And so I think we need to remind ourselves like there should be a point to this right now. If somebody just casually asks you, I think there are strategies for that and I think it's keep it super fucking simple, right? Just keep one sentence, right, explain what you do in one sentence and that's it. And then, and then it goes away because there isn't really anything to be won or lost in that conversation. That person probably just being nice. They don't need to know with your loved ones very different story because they're watching you go through this emotional roller coaster, they're watching you wear yourselves out or they're just not seeing you and they're wondering why. And so for them, I think it is important, but again, putting it into the context of what is it that you actually need to convey to them. So they need to understand what you're doing. And I loved, I loved what you said about, they need to understand why I'm doing right, right, right. What I do far less important, why I continue to do this thing. That makes no sense to you and pretty much everyone else that, you know, give them a reason, right? Let them understand what that driving force that jumps you out of bed in the morning and makes you want to go do this thing. That makes no

Wil Schroter: sense. Yeah. And I think on top of that it is important, really important to have people in your life that actually do understand what you do. Ryan this week alone. I probably had a dozen phone conversations, lengthy ones with different founders who had spoken to some last week in a founder group, some not in a year and every single time I got the same feeling between us, which was, thank God, someone understands what I'm actually talking about, right? So for example, I had a couple of founders that we were working through some details in in an exit strategy where they're selling their company. They quickly understood that this wasn't about just the economics or selling a company, it was about the emotion of what they were going through, right? So I wasn't there as a CFO I was there somebody as a founder that actually understands the emotional pain that comes from selling a company. Yes, there's a financial gain to it. That's actually the easy part. The hard part is letting things go, The hard part is understanding whether this is the right time to make that call, The hard part is second guessing yourself the entire time. And I think stiff

Ryan Rutan: arming your uncle Ernie when he comes looking for money. Yeah.

Wil Schroter: You know, and I guess what I think sometimes folks are looking for isn't necessarily a true understanding of what they do. Like, hey, I wish people understood that we help people start companies. I think founders are also looking for some appreciation for what they're going through. You know, Ryan, tell me if this makes sense, it kind of reminds me of women who have given childbirth, Like I was there, I get what childbirth, I'm going to

Ryan Rutan: Stand back while you finish this one

Wil Schroter: you just uh, you know, I get it, but I didn't do it, right? And so when, when my um, when my wife talks about having given birth, I give that a very special place in consideration because I'm at least smart enough to know or empathetic enough to know that I don't get it the way she gets it, but when she talks about it, she kind of implicitly anticipates a bit of that empathy, right? You know? God, that was painful. You know, you would have to know that you have to understand that, right? And I'm like, I do. I was sitting next to you both times when it happened, but it wasn't me, right? And I think as founders, the only way we're going to find people that can kind of give us the kind of understanding that we're actually looking for is really other founders. That's

Ryan Rutan: 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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