Ryan Rutan: Welcome back to another episode of the Startup Therapy podcast. This is Ryan Ran joined as always by Will Schroeder, my friend, the founder and CEO of Startups.com. Will. There's this notion out there that every time we start a new startup, an angel gets its wings. I mean, every time we start a startup, it gets a little easier, right? There's this myth that like with each progressive foundation, uh, that we become better and more experienced founders, and it just becomes easier and easier and easier. Is this myth, is this legend, is this reality?
Wil Schroter: You know, I, I know what's interesting is some of it's true. But a lot more of it's not true than you would think that's for a lot of people that come to us, I mean, like, literally our business is helping people, you build startups and you know become founders, etc. So our experience there means a lot. And so particularly first-time founders will come to us and they'll be like, you know, tell me just all the secrets. And, and truth be told, there are some secrets. I mean, there are some things where like, if you don't know how to do this, you will fail and we can just teach you how to do it and you won't fail. I mean. That's some of it. There's other parts where it's like, we can teach you everything, and it doesn't guarantee you anything, right? It's just the the the nature of life. I what I thought would be cool is if we talked about, you kind of, you know, what our experience set is, how much of that has helped us in successive, you know, startups. Um, and how much of it didn't make a lick of difference, no matter how experienced we got, it was just as hard every single time.
Ryan Rutan: Yeah. Yeah, you know, it's, it's such an interesting thing too, the experience, it's a bit of a double edged sword as I go back through some of the, the repeat episodes, right? So the things that happened during the first startup and the 2nd and the 3rd and the 4th, in some cases there there. was a greasing of the rails and in some cases it was just like, oh, I know that's coming, so that's gonna feel a little bit better. In other cases, because I was experienced, it turned what was a relatively simple decision the first time into a much more complicated onion layered nuanced decision. Yep, that I I labored over a lot more partially because I knew what the consequences of getting Right or wrong word doesn't mean I did any better with it the second time. It just means that I had to think about it a lot more. So it is, it's super interesting as I go back through through history and think about like, you know, where, where experience helped, where experience didn't help. But then in the areas where it's a little less binary, where it's just like maybe just kind of complicated things in some places and maybe for the better, right? But definitely more complication.
Wil Schroter: I'm drawing like like when I think about this, my own experiences, but also because we work with thousands of other startups, you know, we get to see their experiences as well. Um, I'm drawing from, I'm gonna call it, um, three different experience buckets, I guess, uh, when I'm talking about these, um, one would be my own startups and certainly yours as well, right? we've both done many, many startups, um, from scratch to final resolution, be it good or bad, right? So we've seen this cycle many, many times.
Ryan Rutan: Final resolution. Yeah.
Wil Schroter: The, the best, uh, comparable I could say would be like having a child, you know, from, from birth to, uh, to, to pushing out of the house and you have all different experiences and how that goes, right? Um, so that's one bucket, you know, we're drawing from, we'll talk about on the show. Um, the second bucket would be, uh, you know, as it happens at startups.com, you and I bought a lot of companies. Right, you know, we did 6 acquisitions, but, but we, we did diligence on over 100 companies, right? So we're in the weeds with an awful lot of start-up companies, so we got to see those journeys as well, and then jump into those journeys, take those companies over and see them through. I think it's a unique perspective because a lot of people only know how their stories end. We know how other people's stories ended because they became
Ryan Rutan: our story. They became our story. Yeah, and it was super interesting to see too, because like we would, you know, back into some of the decision making that had been made up until that point. I, I remember distinctly thinking that there were some points that failure where I was like, you know, I would have done that very differently. There were also some places where they had achieved some success, which is what made them interesting to us, and I would have been, I would have done that differently too, not for the better, right? And and so that's what that's what's fun, right? I wouldn't have gotten that outcome, right? I would have done something very different at that pivot point and they did. So yeah, I think that is it's a super valuable experience that we bring to the table.
Wil Schroter: The third bucket that I think we're gonna draw from in this conversation is something that like, I don't take for granted, but, but we tend to forget about you and I is that we have the benefit of living the lives of thousands of other founders. It's kind of, you know, what we do at startups.com. We we work directly in the weeds with all these founders and because of that, it's almost like think about in life. If you had like a choose your own adventure and you have like 4 different ways things could have gone, we have this unique perspective in being an advisor that we get to see all 4 paths in multivariate testing where we get to see different versions of how people dealt with A, B, C, and D at a massive scale. So because of that, we get to see lots of repeat founders and kind of how they do things differently and kind of, you know, what goes through their head. So in this conversation, we're gonna draw from all of that. We're gonna draw from all of those experiences as well as our own, and talk about what's easier. what doesn't get easier whatsoever. Let's start with what's easier. What's the first thing that comes to mind? You've been doing this for a long time. Both of us are in the 30 year range on how long we've been doing this. What's the first thing you think of when you think about what's easier? You know,
Ryan Rutan: well, what's easier? I, I think it's expectation management, right? I think it's, it's the fact that we sort of know who is it said it, uh, John Cabotz in, maybe you can't stop the waves, uh, but you'll learn to surf. Something along those lines, right, which is that you just, you begin to expect it, you begin to know that that it's coming and there's nothing you're gonna be able to do about necessarily other than get through it. And so I, I think that that muscle does get flexed. It doesn't make the things that suck suck any less really. It's just your reaction to it is is a bit easier. I think that, you know, you get used to the ups and downs. I think that's the big one for me. It's the one that of of all of the things that have either gotten better or not, that's the one that's gotten better the most.
Wil Schroter: There's this this scene that I think I've mentioned to you before cause it always plays my head, the opening scene from Saving Private Ryan, and they're all rushing, they're all rushing the beach and people are getting mowed down. It's, it's, it's, it's horrific, disgusting, yeah, horrific in its own right. The fact that it actually happened is like way more, but what I remember is there's like this sergeant or commander, it's just walking confidently around the beach this entire time, guiding. People telling people where to go, and he's like, dude, I'm either gonna get hit or I'm not,
Ryan Rutan: right? That's absolutely a sergeant, by the way. That's absolutely a sergeant, not a lieutenant. They make a big deal. That's a non-commissioned officer. That's the guy who learned to fight by fighting, not at West Point. I mean, they're, they're making a very, a very distinct point there.
Wil Schroter: And I remember thinking this that's
Ryan Rutan: that's the 3rd time founder, right? The lieutenants are the first time founders.
Wil Schroter: And it was interesting because, you know, as we've gone through this experience ourselves, we've been running startups.com for over a decade. Our staff, many of them are young just by nature, right? They haven't seen twists and turns, right? And so we see it not only with Startups.com, the company we run, but with all the companies. we work with the startups, as well as the companies we acquired, you know, things like that. And so where like say within our own staff and nobody in particular, but within our own staff where they're like, oh my God, like this thing's happening, and we're like, yeah, of course, right, like they're on that beach getting got going like you leave this happening, you're like, yeah, no, this is actually how war goes this is exactly how it goes. And so I'll give you an example, you know, some people can, can relate to when COVID hit, right? Do you remember like The feeling that we had, like across the company, like, oh my God, what's happening, right? Like the whole world is shutting down. You know, our response was like name in our first rodeo
Ryan Rutan: like this is uh maybe the world's shutting down. Yeah,
Wil Schroter: yeah, or it was like, look, we shut down in the dotcom crash, we shut down in the financial crash, like shutdowns happen like like and and this is what we do about it. When I say easier. The money still stops coming, right? You know, the the the the part where we're saying, uh, it's like all of a sudden because we've done it before, our customers keep paying and everybody else doesn't, right? That's not that works. But I think you touched on something and I want you to expand on it. You could kind of see around the corner, you already knew how this story plays out. What did that look like for you?
Ryan Rutan: Do you just, you start to know that like after this wave, there's gonna be another wave or after this corner there's gonna be another corner, and so you just begin to expect that. I, I think that the that the challenge early on is that we have So little understanding, like the first time you have so little understanding of how many corners do I have to go around, right? And the answer is, well, it's probably infinite number. There's always gonna be something new coming. And so if you got into this hoping you make it around a couple of corners and then you'd hit the straight away, it's just not the way. No, right? And so I think those of us who have continued to do this thing despite statistics have understood that like, look, with with experience, let me go back to the wave analogy. I'm gonna we get off the corners, back to the waves with with experience, right? It comes a deepening of knowledge. But it doesn't necessarily change how turbulent the surface is, right? Yeah, the ocean may be deeper. I may know more about what's down there. It does not necessarily change with the surface, and as long as you're OK with that, and I think that's part of what happens is you become OK with that, right? I certainly wasn't cool with the fact that the The minute I put out one fire, there was another fire, and then another fire, and then another fire. At some point, you just realize part of my job is firefighting, right? Part of my job is going around corners. Part of my job is riding waves, and that's OK. And I think that's, I think that's what happens over time is you just get so used to the undulation. It's not that you don't notice it anymore and it's not that it doesn't matter because as you said, like when the money stops coming in, the money stops coming in. That's a big problem, but it's how we react to it, right? It's like, oh my God, this is the end of the world versus, now this is the next fire. Let's put it out.
Wil Schroter: You bet, you bet. I also think you, you start to avoid what I'd call making duplicate mistakes. Right, there are a whole bunch, yeah, yeah. I like, but, but, but I would say that there are like a whole litany of things that almost all of us have to make this mistake for the first time and kind of have to live through. It's like a bit of a rite of passage. First time founders, when they go through it, they go through it for the first time, and they, they can't believe this is happening to them and they can't believe all these things. And the second time I founder was like, 00 wait, that just happens every time, right? I saw this great meme on social media the other day cause this always reminds me of like people learning relationships for the first time. It said my 13 year old son just broke up with his girlfriend, and now he's writing her to get his hoodie back. He's about to learn his biggest life lesson, right? It's like such a perfect thing. You only need to learn once. You only have to learn that once. We have the benefit of being like, nope, not doing that again, right? Cause he had the chance to actually make that mistake and and get the lesson the first time, you know.
Ryan Rutan: There's some that are pretty obvious, right? I think there's some of some of the mistakes are kind of nuanced, but I think if we we dig into some of like the kind of the more obvious ones, it'd be things like taking on co-founders for the wrong reasons, right? Like I needed a developer, so I, I took on the the the CTO who was just a junior developer who now I will regret later. It's things like just overstaffing in general, raising too soon, raising too late, right? Like just or mismanaging capital, spending in the wrong place. There's a lot of those things that I think you do, you do reflexively learn and I think that was kind of the the point I was making really early on, which is that some of those decisions felt really easy the first time through, right? And not that I made them well, they were just easier decisions because I didn't know any better, right? So it was like, should I hire people? I'm here by myself. I should probably hire people. What are they gonna do? I don't know, right? We'll figure that out later. Like, that's a second order problem, right.
Wil Schroter: And and you don't understand that overstaffing is even a thing. You're like, oh no, you're supposed to grow. How could we possibly
Ryan Rutan: be overstaffed. There's no staff. But, but that's funny, that's funny to think about, right? Because you and I know that you can go from one person to two and actually be overstaffed. Yeah, right, that's the thing. It does not occur to you the first time you're going through that because you think like overstaffed, well, that must mean like 1020, 30 people or something, right? Like there's some arbitrary number that's not the number that you just hired, um, it feels like maybe that's overstaffed cause you're overwhelmed at that point, uh, but you're overwhelmed with things that probably won't be solved by staffing up.
Wil Schroter: So there are like colossal life lessons that I would argue you kind of have to live through to really get. Right, um, like that hoodie experience to really appreciate what that means to not do it again. So if you have done it again, right, like I'm, I'm 9 times deep on starting companies, there are a ton of stuff that I learned in startup 2 or 3 that I've never done since, and that is in. Valuable. And I think when people are, are thinking about, oh, this person has a lot of experience, they must not have to go through these things. We'll talk about that part later. But, um, some of that's true. I mean some of that I'm, I'm just like bad hires. You see somebody in an interview, right? And, and they check every box in the interview, say something crazy and they don't even realize they said it, right? But I'm like, nope, nope, nope,
Ryan Rutan: I've been there where this goes,
Wil Schroter: yep, yep, it's things like that. That allow you to essentially avoid colossal mistakes because you've already had that experience. The other thing I thought was interesting is in raising capital, but not for the reasons people think. So people tend to think, oh, we've raised before, VCs must know you and love you and want to invest in you. Ideally yes, but statistically we
Ryan Rutan: first.
Wil Schroter: Right? So you got some explaining to do. But I don't think it's because you have a reputation for having it done, done it before, that that could help. Again, it could go either way. What I think it is, is you know what it actually is. Like you can see through the bullshit and all the pixie dust of like, oh, investors are gonna come, they're gonna give you money and so much expertise and they're gonna help you along the way like you're like, no, they're gonna be the biggest pain in my ass ever and. And I'm, I'm gonna take it with a grain of salt. Uh, Pixie dust is worn off at that point.
Ryan Rutan: Yeah, yeah, I mean, it's rare that we talked to a founder that's raised more than once, who didn't do it at least slightly differently the next time and the next time, and then at some point say like, hey, maybe I'm never gonna do that again, like, the next thing I build is just gonna be gonna be mine. And we see this, I mean that, you know, across the board that like it changes over time, just even how we treat things like our cap table, right, like how much equity we give away. I was looking at this the other day I was I got curious about, I, I remembered, you know, that Elon had an early exit in in zip too. At the time they sold that and I knew, I knew they'd gotten squashed down on the cap table, but I didn't know how far he was sub 6% when that sold, right? Not that taking $20 million home was a was a bad deal, but they sold the company for like almost $400 million. And so when you take away 20 at that point, right, it doesn't doesn't feel amazing, right? And you can see that, you can see the difference in the way he's structured things since then with with Tesla, with SpaceX, completely different, completely different structures. You
Wil Schroter: know, something that's really funny about everything we talk about here is that none of it is new. Everything you're dealing with right now has been done 1000 times before you, which means the answer already exists, you may just not know it, but that's OK. That's kind of what We're here to do. We talk about this stuff on the show, but we actually solve these problems all day long at groups.startups.com. So if any of this sounds familiar, stop guessing about what to do. Let us just give you the answers to the test and be done with it. I think if I reflect back on the things that that really stand out to me, like, man, it's way easier than it used to be, a couple specific things to me. Not necessarily categorically to everyone else. One of them is I'm more of a, I'll believe it when I see it kind of guy, right? Particully with people. Um,
Ryan Rutan: we went through this yesterday, we went through this yesterday. Well, we had, we had an example where there was like a proposal that needed to be needed to be made uh for a potential partner, and we're like, we could go super super deep on this, let's just test the waters, right? Let's let's put a toe in and see if there's anywhere to go from here, whereas like the first time through, you and I would have been up till, you know. 3 o'clock in the morning last night, we'd have been, you know, crafting out like, do you think this font works better than that one? Like, what if we were, well, what about, what about, what about landscape? What if we turn the whole thing on its side, like, you know, you go through all of this shit and you end up doing things that you just don't need to do, right? So I, I think that it's, it's an illustration of that. I'll believe it when I see it, said differently. I'll put in the amount of effort that's required for right now, which as a first time founder, no idea, you're like, I guess I'll throw everything at this problem, right? Whether it's that big of a problem or not.
Wil Schroter: In all of the the implied commitments that people make to you as being a startup founder, right? So you're hiring people, right? Whether it's a developer, or salesperson, whatever, they're all making implied commitments vis a vis their resume, what they say in the interview, etc. And and when you're when you're doing this for the first time or when you're young in your career, you tend to take it at face value. You assume that because they can do these things, that they will do these things you find later is a way back to
Ryan Rutan: the, go back to the investors discussion, right? Go back to the smart money thing, right? This this investor has all these other. companies that could possibly buy from us. This investor uh has this massive network of of people they could turn us on to. This investor has all this stuff they could do, they could do, they could do. Will they? Probably not. Was it in the term sheet? No. Was it next to the zeros on the check? No. Then it's probably
Wil Schroter: not gonna
Ryan Rutan: happen.
Wil Schroter: Of, of all the things I think about that have made my life easier as a founder with 30+ years of experience in just doing this for a living nonstop, I think I would rank. Understanding people better than any of them, right, in as much as it's not even about being callous or or questionable, it's more just not being oversold where I was like, oh my God, this person's gonna be a co-founder so they're gonna be so engaged. Maybe, maybe, maybe seen plenty of examples where that was not true, right? So maybe, or, you know, again, you know, we we just partnered with this company and they're so fired up, we're gonna do so well together.
Ryan Rutan: Send me the quarterly report in a quarter, right?
Wil Schroter: Yeah, and see how it went. The reason you just, you touched on this when we started this, the reason that's so valuable is holy shit does it save me time and more importantly, emotion, right? Like when that developer doesn't work out, I'm not shocked. I'm like, yeah, OK, they have like
Ryan Rutan: the first time, maybe a little the second, but by the 3rd, 4th, 5th, 6th time, somebody didn't live up to expectations, I realized one of two things. One, maybe I had the wrong expectations. 2, I have no right to have expectations for anybody, and even if I do, it won't really matter, right? They're gonna do what they're gonna do with my guidance, all that stuff, sure, right? But I cannot, I cannot let this completely, completely deflate me. Yeah, I, I think the, the people problem is a big one.
Wil Schroter: And so the the other side of it was like, you know, again with people. I remember early in my career when someone would leave, I would take that as such a massive personal affront. Like, what did I do wrong? Like, where is the gap in your pay in
Ryan Rutan: myacked up their bags and set up. See you later. Good luck, kid,
Wil Schroter: right? almost like them leaving was like them divorcing me. I mean it's a really, really, really personally. What I didn't realize, like at the time, and, and it took me many years later to, to realize this, is people leave, leave all the time, like, um, I've done 9 startups, which means I have left 9 of my own companies. I've divorced myself. So like, it, it took me a long time to get less emotional about that, and I think about how much time and effort um and distraction was caught up in not having that muscle, right, not being able to process and go, oh yeah, of course, right onto the next one. I'll see you back here in 5 years, like, you know what I mean, like, like circle life, right? Like I'll see you again.
Ryan Rutan: I think that that emotional maturity is one of the things that you we also learn as founders that it doesn't go back, right? Like that that's one of those things that that does become. Quite useful and and you do continue to flex on it. So I think situations that require that emotional maturity, those are all easier by some degrees based on how much you've matured over the time. Agreed,
Wil Schroter: let's flip it. Let's go, let's go to the other side altogether. What is not easier, but 30 years in, hang on,
Ryan Rutan: I've got a little bit of devil's advocacy for the people one here because I, I just, I couldn't leave it alone. I couldn't leave it alone because we have been doing this for so long, i.e. we're multi-time founders and we've done this over, over a period of time. You go through some generational changes. You and I have been through this where it's like, well, but in our day when you hired somebody, here's what they did. And then the millennials came along, were like, yeah, Grandpa, it's not how it works anymore, right? And then Gen Z and now whatever is after that, I've lost the plot, right? So there, yes, the experience does help, but again I think we have to be a little bit careful about letting our experience temper our our expectations and saying that like because. Because this is how all of my previous employees were, this is how all the future people will be, and that just has not been the case. So just one little caveat to the people getting easier.
Wil Schroter: Let's go back to not easier. What is not easier, um, no matter how many times you do this, why isn't it easier? Like why? what's what's broken that like you can't master the thing? What's the first thing that comes to mind? Well,
Ryan Rutan: I look, I, I think that there's, let's let's talk about a fundamental reason why it doesn't get easier every time. Because we're not doing the same damn thing, right? We're doing something different every time. It's a variable. Every time we start a startup, we're essentially setting out to do something that's never been done before, even if we've done something else before, right? Remember when, who I, I bring this up every, every like 90 episodes or something. Remember when Michael Jordan decided to play other sports? That was neat for a minute, right? Like it didn't make it any easier, right? Like he did not win a World Series. I think that's the biggest thing. So like uh we can get into some specifics around what's not easier, but I think the reason, the core fundamental reason, and this is where we we trip up and we're like, well, but I've done this before. You've done a thing before, and you've done a thing that looked a lot like this, but you have not done this thing before. So let's let's start with that. I,
Wil Schroter: OK, so, so let's talk with the product, right? Yeah, sure you haven't built this product before, so let's talk product market fit. Sure,
Ryan Rutan: product market fit is just as difficult every single time. And every single time we have experience building really similar products in a really similar space, it's still no easier, right? Maybe, OK, maybe it's a little easier. Maybe it's a little easier like you already know some of the definition around the audience maybe, right? You're like, OK, we know some of the things they like, we know some of the language they use, so we've got some maybe, you know, uh communication marketing product fit, but product market fit is always really, really tough, because even, even for example, you built something in the same space before. Well, that space has probably changed since the time you did that, right? By virtue of you having built something for it, it changed, right? There's so many variables, right? Like, oh, well then we went through a pandemic. Oh, then AI came around, oh, then whatever else happened that changes that market fundamentally.
Wil Schroter: We want to believe that if we've done it once, that we can do it again, whatever that thing is, the thing we built before, etc. it doesn't work like that. It just doesn't. And and and I think it's a Bit of an arrogance to us as founders thinking, well, I've done it before, so of course I can do it again and and part of that arrogance and confidence we need.
Ryan Rutan: It's the same, it's the same as the biological joke that gets played on us when we decide to have children and then more children and then more children, right? Like you forget what you went through and you assume it'll be easier. You're wrong in both cases.
Wil Schroter: Every time, like, like you're saying right, every time we restart, there are so many variables we change and there's a few we we can't get around. When we started the one thing at the one time, we can't go back in time and be that same time period. The world changed in the, the world changed in a ton of different ways. In '94, I started one of the first interactive ad agencies. That's awesome. And it was really successful, but that was 30 years ago, yeah, right?
Ryan Rutan: Your qualifications for starting a digital agency today would be less.
Wil Schroter: I, I mean, like, right? And so just because I was associated with that category doesn't matter. Another more recent example, you know, I mentioned that the last company that I did before Startups.com was a company called Unsubscribe.com that I started with Jamie Siminoff, who I mentioned is the founder of Ring, the doorbell company. Jamie and I both had like 6 companies before that and Jamie had some success with another company, I think it was called Simulscribe, but he had like 5 others that that did OK not great, right? Same with me, right? I had some successes, some failures, whatever. And we worked together, which you would think would be like more like uh horsepower, and to some degree it was, and that company did OK, not great, but, but I, I guess my point is, it's just, it didn't make it any easier in the same way that the, the 5 companies I did before that or the 5 companies he did before that didn't necessarily all hit. I'm of a of a very certain opinion that as a serial founder. You are starting from zero every single time. You've got some advantages, some experience, but product market fit ain't one of them.
Ryan Rutan: No, no, it's not. I look in that, in that regard, experience is a great teacher, but there's no shortcut for understanding your audience in the context of today. Whatever you learned in the past is a history lesson, right? It's exactly what it is, and it is helpful, right? Like if you've gone through finding product market fit, then you know what that process looks like. What it feels like. So that part of it will be like getting it process wise, but getting it is absolutely no easier because you're starting from that same point of almost 0 information, lots of guesses, and a ton of variables. You got to go make some constants out there and figure out like what of these assumptions are true and are we close to matching the product with the market
Wil Schroter: need. The other thing I found not just for myself, but watching other companies is every time they restart, you know, build something new, um, what's not easier, marketing. I think marketing, I mean, even if you get it, hell, I came from an interactive agency like, like I was grown up on this stuff, right? It's a slog every single time. I mean you're our CMO you know better than anybody. You don't get any bonus points like maybe you have some media relationships or things that worked well in the past, which I also think is. Sometimes a mark against you because you tend to rely on things that aren't current anymore.
Ryan Rutan: Exactly. You may lean on relationships and assume that those will be the things that get you because they were easier to reach than than maybe the one that actually would have been more beneficial. Now I think there's a, there's a real danger in using past experience as a crutch.
Wil Schroter: Yeah, and, and with, with marketing specifically, new product, new audience, new timing, etc. and and by the way, when we're talking about this, experienced founders, I'm sure by now are like their next door from nodding their head because they're like, dude, I went through all I mean we've just all of you, so we're we're telling you what you told us, right? So this is no like special thing from us. But the other side is what I. I want folks to really listen to and lean in on. I want new founders to listen to this. I want new founders to listen and go, wait, hold on a second. You're telling me these like super experienced people I'm going up against, they don't, they don't have like a distinct advantage on me? Yeah, they have some. We talked about some of those. But the ones that really matter that you should be more concerned about, like, are they getting the product market fit faster than we are? Are they gonna, they have a massive. Jump start on marketing like we don't, not really. I mean, again, it's better than 0, but it's not the ace in the hole that people think it is. Talk to enough VCs that have funded enough 2nd time, 3rd time founders, and they'll tell you the same. They'll be like, hit it out of the park on the 1st 1, 2nd, 3rd 1, haven't seen shit since.
Ryan Rutan: Yeah man, no, I, it's one of those things where like I think. Success is never owned, right? We don't own success, we rent that shit. We rented, and the rent is due every single day, right? So regardless of what you've done in the past, you gotta pay the rent, right? You're going to have to re-achieve success and in almost every single case I can think of, certainly all of my own experiences, achieve it in a different way. 100% different? No, not necessarily, but enough different that it mattered.
Wil Schroter: Another one though, like, uh, no matter how many times you go through this. Losing sucks exactly the same every single time. Now I thought there was like a cheat code on this one. I thought that like if you'd lost the Super Bowl once then losing it again would be OK because you're like, oh, you know, we get past it, we go back training him blah blah right? no. I,
Ryan Rutan: I have a callus over my heart right in that spot. It no longer hurts,
Wil Schroter: right, right, that does not work. Running out of money, going through the part where you've got to let everybody go, going back to your investors and telling that story, going back to your customers, going back to your friends and family. I mean, everybody, right? It sucks. It sucks every single time you and I had a founder reach out to us last week, shut down the business, you know, we're doing, you know, uh, postmortem and stuff like that. Great guy, awesome founder, um, he'll he'll do it again, it'll be great, right? But what I shared with him, and I'm, I'm guessing you did too, was, dude, I've been there, right? Like I'm not gonna sugarcoat this and tell you that this is, this is great and don't worry about it. It was actually the opposite advice. Uh, my advice was, uh, live in it for a minute, right? Remember this feeling, right? Um, yeah, hold on to it. Do it, write it down, go journal it, because it's, it's easily the most valuable lesson you'll learn. It's a shitty lesson. It sucks how you have to learn it, but of all the things that will give you really the most pointed guidance for the rest of your life are happening right this second. Don't let him go. Now that said, Still sucks, still sucks,
Ryan Rutan: yeah, yep, spoonful of sugar does not make the shit taste any less like shit, it just doesn't. Yeah
Wil Schroter: and you know, like, again, I, I mentioned, you know, top of the episode like when COVID hit, we're like, hey, we've been through this before. I had been through this before in in the dot-com meltdown, I was running a very large company, shit just started to fall apart, right? Like our clients massive. You know, Fortune 500 clients just stop paying us out of, I didn't know that was possible, but
Ryan Rutan: we did the work and you signed the contract and my account is empty, so I think you know what you need to do here.
Wil Schroter: We had a, we had a client, I'll never forget this. It was a small project relative to where we were at the agency at the time, but it was a $5 million dollar bill, right? We've done a $50 million worth, not insignificant, right? And and we sent them the bill, and again it's a Fortune 500 massive company. And they stiffed us. They were like, yeah, this didn't get approved, blah blah blah, dotcom bust blah blah blah. And I was like, and but you're gonna pay it, right? Cause you're like a huge company and like we have a contract, and they were like, I have payroll and yeah, yeah, oh my God, right? They're like, no, we're actually not gonna pay it. Uh, take them all again on that one. And if you want to work with us again, you just got to let this one go. And I was like, wait, what? Yeah I had no idea that was even on the table. Like I, I had no idea. I was like 27, by the way, um, but like I, I had no experience. But if that happened today, having had that experience, it would not suck less. I'm like, it happened before, not a big deal.
Ryan Rutan: Yeah, no, still, still a half million dollars state, full surprise.
Wil Schroter: Oh what is happening right now? I've had multiple companies that I've started that have failed, and it hurt, it hurt every single time in the same way. It wasn't like better the second time, might have been worse.
Ryan Rutan: Yeah, I, it's, it's funny, but yeah, stick on that for a second because I certainly, and it's, it's big things and small things, not even the entire startup sometimes, but like. Anytime I've made a hire, right, and then realized it wasn't the right hire, and then replace them with somebody that I thought would be the better hire, and it still wasn't the right hire. The second one hurt even worse, right? Or launch marketing campaign, right? And then it doesn't work, and then launch doesn't work and it's like it doesn't doesn't necessarily feel better. Sometimes the the the the experience of loss can compound into feeling worse now like you, you get used to the fact that it will happen, um, but I, I think you're right, there is a, there can be a compounding effective.
Wil Schroter: There is, and so. Here's what I'd say overall, if we're to take a look at just the the whole continuum of experience and how much of it, you know, helps and how much of it doesn't help. Obviously more experience helps, but what's really interesting about this startup game. Is how much of it you don't get to reuse, which is why there are so many first time founders that are so successful, because Mark Zuckerberg can show up at 19 years old and build one of the most valuable companies in the world, and you're like, wait, how is that possible? Like because his opportunity at product market fit is damn near the same as Everyone else's, right? And I, and I think when when we when we consider, um, when we're a first time founder, hey, do I need to have all this experience? It doesn't hurt, and any founder will tell you it doesn't hurt, but at the same time, this is the part that people don't get. It doesn't change the outcome. The big variables that that really matter, right? The experience helps, but the big variables are really around the things that you cannot control, and every time you do it, you're doing it for the first time, you gotta hope like hell, it's the last time.
Ryan Rutan: Overthinking your startup because you're going it alone, you don't have to, and honestly, you shouldn't because instead, you can learn directly from peers who've been in your shoes. Connect with bootstrapped founders and the advisors helping them win in the Startups.com community. Check out the Startups.com community at www.startups.com to see if it's for you. Could be just the thing you need. I hope to see you inside.