Startup Therapy Podcast

Episode #196

Ryan Rutan: Welcome back to the episode of the Startup therapy podcast. This is Ryan Rotan from startups dot com. Joined as always by my friend and the founder and CEO of startups dot com. Will Schroeder. Will we love to sit around campfires and just tell the rags to riches stories of founders, don't we? Right. And they're amazing the anecdotes of, you know, Steve Jobs and in the garage and Brian Chesky on his parents' couch in a basement eating nothing but Obama owes. They're uplifting their incredible except for kind of a specific population and who might that be

Wil Schroter: the poor bastards who actually had to live them? That's

Ryan Rutan: exactly right. Right. They make for a great read on social media. Living through. It is an entirely different shit show.

Wil Schroter: I tell this story. You know what I'm doing, kind of like a back story and stuff like that. I tell a story of how, like, I didn't get into college and all my friends were going to college. I was supposed to be the first person in my family to go to college, but I lied and told everybody that I was getting in and I hadn't. And I had to go to school for like a year as a fake student essentially. Right.

Ryan Rutan: I was just hanging out in the classrooms to stay warm.

Wil Schroter: It was so bad and it sounds like a hilarious story. But what people don't really understand is I actually had to live that story. There was nothing cool about it at the time. Like, I'm going to class while working two full time jobs. I'm going to class on weekends. I show up at school like a total loser because I'm not actually a student. Right. So I'm not even supposed to be there and I go to my teachers and I'm like, hey, this is gonna sound crazy. But could I just sit in this classroom and pretend to be a student? So that no one will humiliate me right? To find out. I'm the only person that didn't get into college.

Ryan Rutan: Well, do you remember any of the responses? I, this is a total but I would love to know like, do you remember any of the responses? Like was there a gem that stood out

Wil Schroter: like every single time they were like, what are you even talking about? Like first off, why are you even here?

Ryan Rutan: That's kind of the expected response. That's kind of the expected response. Yeah, I was, I was hoping there was something else

Wil Schroter: doesn't get into college but shows up anyway and says I'll pay for courses but I don't want any credit. I just wanna, I just wanna be, I

Ryan Rutan: wanna be here. I just wanna sit in here.

Wil Schroter: And my thing was like, look, you've got 50 kids in this classroom that are accepted that also don't want to be here also, like, you know, at least I wanna be here sort of. And so I tell that story and then it, you know, led to starting a company and all these great things happen and it sounds like a cool story. It is a cool story. Unless you're the poor bastard me in this case, who had to live that story because the reality of that story was not cool. The reality was I am dead tired by the time I show up for this class because I've been working two full time jobs from eight AM till like five PM. I'm making 100 phone calls as a tele marketer for mainframe computers from five PM to one AM. I'm making incredibly delicious sandwiches at a uh northeast location called uh d'angelo's, which if any of you are familiar with, it's oh and so

Ryan Rutan: definitely, definitely had some forced naps. Thanks to

Wil Schroter: d'angelo's. Oh my God. It was amazing. And so I was a cheese steak, uh magician. So by the time Saturday morning rolls around, the only time I'm physically able to take classes, I am exhausted and I don't want to be there and I'm not getting credit for it. But the whole point is I tell the story how it turned into me like, you know, blah, blah, building a company, whatever. And obviously, if that part of the story didn't exist, if it just led to a lot of me making a lot of cheese steaks, it wouldn't be a very good story. But you know, when I end up starting an internet company, all this cool stuff at the dawn of the internet. And so everyone's like, oh my God, what a cool story. I wish I had one of those, which is where our story here begins. Be

Ryan Rutan: careful what you wish for.

Wil Schroter: No, you do not or said differently. You probably do have that story and we'll get into that right now. And so I think, you know, the crux of it is that these myths are largely bullshit, especially for the people who had to live them and, and you're probably living one right now. And I think we should kind of talk about how to, how to take some of the air out of these myths, not to deflate them so that people can appreciate them, but to make people maybe understand them quite a bit differently.

Ryan Rutan: Yeah, I think we've gone too far in terms of the distillation. I think we've gone way too far in terms of the revisionist history and yeah, it makes for great headlines and great sound bites and, and great short stories. But those are good for inspiration, right? To get you started. You're like Well, if it's, that's, uh, you know, it starts rags riches. I can do that. I've got rags now. I'd like to be rich. Uh, let's do that. Right. So, I've got that nailed down, the challenge becomes that. And when we start to compare ourselves to that and going, well, where's the richest part? I've been doing this for a year, for two years, for three years, for four years. All they said was, you know, slept on couch became overnight success, right? We're leaving a lot to be desired in the recanting of these stories because it's important that we understand there was a whole lot of other shit that was involved in getting from A to B in this case, right? We're like A to Z and we've just left the rest of the alphabet out. So, yeah, let's walk through some of these, the classic uh story arcs here and let's, let's dispel some myths and pour some reality back into the uh into the bowl.

Wil Schroter: Well, so I'll give you two parallel paths a week or two ago. A buddy of mine calls me up and he said, listen, company was on the brink. I had no money left, had to lay off half my staff did 100 and 20 investor meetings and every single person said, no, I was completely screwed. And I remember I said to him, I said, you know what I was exactly there, you know, with one of my past businesses who raised some money went out, had 80 investor meetings over the course of a year and a half, which is a very, very long time, long

Ryan Rutan: time to do anything without a positive result. Right. Like, just to keep doing that, keep opening the door, walking and get punched in the face, walk out, walk to the next door over and over again. And, you

Wil Schroter: know, a lot of people look at that and they say year and a half isn't that long. It can be

Ryan Rutan: depending on how you spend it. Yeah. Yeah. How, how about a year and a half of uh jail time? Does that sound fun? It's only a year and a half, right?

Wil Schroter: And it was just this high concentration, high intensity, full sprint. Nothing but manic panic the entire time, which also resulted in the end, the end of that story is a story we've told many times in the pod before, which is my heart stopping. Ok. So that's one way that story could go, which is how it went for me. He ends up on his like 121st pitch after pretty much giving up and ready to call it all quits. Someone comes in does the deal does a huge round. They even get some acquitted and it is an incredible deal, right? And so you look at that and someday he's gonna tell this story how he was on the brink and he had to let people go and, and then all of a sudden mysteriously, like, you know, like it all came to fruition, but there's a few things that I think are missing from that story. One is we usually fast forward Ryan to the parts of the story where it actually starts to turn or gets interesting. We don't talk about the part where it was just miserable for a really long. It, it's kind of hard to illustrate that part because it just sucks.

Ryan Rutan: It is. It is. And it's a lot of repetition and that's part of what makes it suck. And it's just, it's this, but think about how we tell that story, right. I did 100 and 20 pitches to get to a signed term sheet, right. We give equal weight to two things there, 100 and 20 pitches and a signed term sheet. 100 and 20 pitches takes you 18 months or more as signed term sheet takes about, you know, two days you get down to that point to get to that point or, or it takes 30 seconds to actually sign it. But we give equal weight to those things. And I think there's a, it's a hugely misleading characterization of the process because yeah, people of course, they know like, yeah, the 120 but there's not enough emphasis put on that. There's not enough detail fed into that for us to go and that really sucked. Right. Yeah, we all get it like 100 and 20 pitches, but spend a minute thinking about that, do anything 100 and 20 times. That is a high stress, high stakes activity and tell me how much fun that is over and over and over again. It's like playing 100 and 20 Super Bowls, right? It's insanely exhausting, insanely stressful.

Wil Schroter: And we love the story though that I was against all odds, right? We love the story that, you know, I was down on my luck. There's a story that my friend Matt coffin tells. Matt was the founder of lower my bills dot com, which back in like the mid two thousands or whatever, I think, I think it sold for like 350 million in cash or something like that. He did really well with it, but he tells a story about how it started and kind of how destitute he was and how at one point they had missed their round just like my friend was talking about and how he had to sit in front of the whole staff and tell them everything was gonna be ok. And then immediately after that meeting was done, sit down with the CFO and try to figure out how to fire everybody or let lay everybody off. Right? I mean, like just this do reality of the moment and it's this really powerful, really interesting story unless you had to live it like, right. I mean, how painful and gut wrenching and awful. That would have been. It sounds cool because then there's the part where he sold it for hundreds of millions of dollars, but most people don't right about now. No one is right. Think of how many people are telling the wrong epilogue to this story.

Ryan Rutan: Yeah. Yeah. Exactly. Now, it's so tough. Right. Because on one hand we have to maintain that optimism right to the duality of that story, right? We're still forward face and we've got to be doing all the things and yet when we run into these dichotomous situations, right? It's gut wrenching for the founder. I mean, it, it literally feels like separating your physical body and your soul, right? Like you have to live through this stuff and again, it gets boiled down to an anecdote where it's like, yeah, one day we were telling the staff that they were all gonna be fired, or half of them were gonna be let go. And then two weeks later, our funding round came through right uplifting. We're at that hero's arc part of the story, except for the half of the staff that was out of a job, right? Like it wasn't awesome for them. It wasn't awesome for them. It wasn't awesome for the founder to have to do that because at the moment you're doing that, it doesn't feel like, you know what, in two weeks, we're probably gonna turn this thing around 100 and 80 degrees, right? So this is the thing that I think we really want everybody to remember. You can't see any of this shit while you're going through it. It's not apparent. Yeah, I think that's super important because if you're living through this now and you're not in the, let me go back and revise history and turn this into a sound bite. It just all feels like it sucks and it feels incomparable to some of these heroes journeys.

Wil Schroter: Every single founder I've ever talked to throughout their journey of success have all had a moment where, you know, things started to turn, but it's not the movie moment that we expect it to be. It's not one of those things where and then it all happened.

Ryan Rutan: Isn't it preceded by a montage? Normally

Wil Schroter: it's, it's so it was a hard work montage, but it's not the way people think it is. Every single founder that I've ever talked to about. Their journey has said the same thing. I never saw it coming and not to say that I was just so pessimistic, but to say it just one day kind of happened. Not like on a single day over a period of time in our minds. It's a lottery ticket event where everything's shitty and then this happens and then there's this watershed ip O moment. It's not the way it works. Here's how it actually works. I'm going further and further and further into the abyss. It's getting darker and darker and darker at some point. I look back and I can't even see light anymore. I'm just fully immersed in this thing. And in my mind, I have no idea where, whether I'm moving forward backward and let's pause there for a second when you're in the middle of the abyss, which many of our listeners are right now. You don't know the difference. You don't know if, if you were just making things worse by progressing or getting to an end game. And I think if we kind of highlight one part of this discussion, it's that no one does. And that's the problem. You said it a moment ago, you don't know whether you're telling the downfall story or the come up in the story. You know where you

Ryan Rutan: are, no idea where you are in the ark, right? You're just operating, you're just doing the damn or if there's an arc, right? If there's an arc, yeah, it's so important. And I think this is one of the things that we've stressed throughout a number of episodes in the podcast, which is that simply making sure that you can be around long enough, right? To circle back to your point. Everybody says it came as a surprise, right? I didn't see it coming. I didn't see it coming, which is to say we can't really predict these things, right? That our Black Swan moment is coming. We're not gonna know that's why it's a black swan moment, even just the linear growth. And at what point that becomes OK, it's really hard to project really hard to understand and it works in reverse as well. If you're, you know, going off the cliff, it's really hard to project whether you're actually gonna hit bottom or if this is just a temporary downturn. Right. So the key here is, don't try to spend all your time with a crystal ball seeing what the future is. It's impossible to predict. Put yourself in the position where regardless of what tomorrow brings, you can tolerate it, you can make it through to the next tomorrow and the next tomorrow and the next tomorrow. So that when your moment does come, you're there to appreciate and harness it right?

Wil Schroter: You 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, talk about this stuff on the show, but we actually solve these problems all day long at groups dot startups dot 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. There's another piece to this and we'll kind of expand on this a little bit. We often assume that our founder story is one contiguous story in as much as we start off in college or what have you. And then when we come out and we have a great idea and then we start a company, it raises money or it does whatever it's gonna do, it then becomes something big. I have yet to see a founder story that basically works like that. Now they exist, right? I mean, there's a Mark Zuckerberg, there's, you know, there's people done it. But generally speaking, the story looks a little bit more like this. I started out, I thought it was it. I put in all my chips. I burned five years and failed. I then, you know, licked my wounds. I eventually came back with another idea. I went all in on that, that turned out to be even a worse idea. Then I came back and I did another thing like when we go to your original history, like our Netflix drama version of the story, it's very linear, but the reality is, it's just a consistent series of misses or near misses or base hits at best.

Ryan Rutan: Yeah. It's a lumpy, patchy, barely connected series of events that end up turning into what sounds like a very linear success story at the end.

Wil Schroter: Uh I was given a talk with two friends of mine, Jamie Simonov, who I mentioned before, Jamie is the founder of Ring and Jason Nazar who started docs Stock, he sold that and I think he's running comparably now. And Jason was having us for some event in Santa Monica. We were both kind of presenting our origin stories and stuff like that. And Jamie and I had very similar stories and this is before we work together and Jamie was talking about how he'd started multiple companies. This is again before Ring, he started multiple companies and he kept thinking that this was it. He kept thinking that like, ok, I finally found it. I finally found it. I finally found it and it kept not being it. I'm using Jamie of course, because he obviously had a great success. But what people don't understand is that that was after about 20 years of misses in ways that don't sound like a big deal because, oh, it worked out in the end unless you had to live it or unless

Ryan Rutan: it didn't work out in the end.

Wil Schroter: Yeah. He told me a story of, I think it was a company called Grid. I might be getting the name wrong. It doesn't matter where he thought it was it. And he had pumped a million bucks of his own cash into this thing, which at the time, you know, he was probably late twenties, early thirties. He was like, that was my nest egg for life. It's a lot of money and I, I kept putting more money because I thought we'd get another round and I thought we'd get another round and just kind of digging further in and then it was gone and I had no way to put it back. And he looks at that and he says, I thought that this was that moment where things are, you know, on a down swing. But that's ok. I'm, I fight it out and I win in the end and I didn't, I didn't win. In fact, I just came up empty handed around that same time again. That's when I was, uh, running a company called Afford It and a few others. I felt the exact same way. I felt like times were tough. I was really stressed out and that's ok. This was gonna be the thing where, where I work really hard and I can, you know, make it work and I, I turn it around power through

Ryan Rutan: and I'm there. Yeah.

Wil Schroter: Yeah. And I did, I gotta tell you at that moment, like, you know, when I was in the thick of things, Ryan, when there was no idea, like whether I was going to be successful or not, it looked exactly like in my late thirties, like it did when I was 19, starting my first company, I had no idea what was gonna happen. Not a single signal. And I do this for a living. Yeah, that's

Ryan Rutan: the thing. It's so hard. I mean, the, the idea of predicting anything other than our desire to get up tomorrow and do it is almost impossible, right? And, you know, I think if you're trying to say, like I find this becomes really problematic when we see people comparing themselves to these stories and these timelines, right? They're like laying themselves on, they're saying, well, look, you know, by whatever date, you know, the, you know, by the same time one of my competitors were name insert giant startup, who everybody knows origin story of here. And they start to compare themselves to that. It's super, super damaging and it's not helpful in any way that I can see other than if you want to make yourself feel like shit because you're gonna pick whatever like the best archetype of the story is and you're gonna compare yourself to that. And my God, you came up short. Oh Imagine that. And it's really, really problematic because again, you're now just kind of at best you're laying looking in parallel, right? You're just saying like, OK, at this point in time, here's where I should be and I'm not, or here's how, here's how we're different and it just, it doesn't serve much of a purpose. And again, you're looking at revisionist history's version of that story, not the reality of that story. Had this conversation during an office hours today actually, where uh somebody was quite literally, he said, you know, in comparing myself to a couple of other companies who are in the same space who are a few years ahead of me. Here's where I feel like I'm falling short. And so we had this conversation around like look a you're getting the Instagram version of their business and you're using that to say, here's the story, right? Super dangerous. B you're not doing all of the exact same things they are and whatever you see as like that overnight success or if you think, I think they're three years ahead of you, they might be 15 years ahead of you, right? If we go back to your example around Jamie, right? Like if you're only looking at Ring, that is not the story, that's the story of Ring. But when we look at the founder's journey, you have to rule all of those other 15 years of 15, 20 years of failure or you know, not massive success that he had, that led up to that, right? Burning that entire nest egg that made him who he was at the moment that he chose to start Ring may or may not have contributed to success. I'm not saying like he had to have burnt that to learn the lesson to be successful. Ring. That's not what I'm saying at all. That would imply that it's a necessary step in the journey. It isn't necessary, it just was a step in his journey. And one that we tend to willfully ignore when we're comparing ourselves to their success to our own detriment. It's just not worth doing.

Wil Schroter: I don't think we appreciate their pain either. I want to dial into this because I think when we look at that and we say, oh, I'll give you an example, you know, uh, we had to go to, you know, work two jobs and go to school full time on the weekends. That was really hard. And I gotta say, like, there was no part where I was like, I hope this keeps going. There's no way I could have maintained that pace. Now, I did a startup and probably increased my hours. But there's no way mentally and emotionally, I was gonna be able to continue that pace. That was one of those things where I was willing to do it knowing that I had a limited time offer on this one. And when people look at the sacrifice, so to speak again, we belittle it and we say, ah, well, you know, you went on to start whatever you did, right? You know, when the show I built this and they talk about the founder of Chipotle and all these things and everything that they did again, they make great stories. But I look at those stories very differently. I don't look at the amount of success they had. I look at the amount of pain they had and I empathize. And I look at that and I say, you know, I, I'm a huge fan of uh Richard Branson, wrote his biographies and stuff and I look at what he had to go through and how much shit he needed to eat in order to even start to become successful. And I'm like, damn man again, having done of it myself, I can appreciate it. But when I see it on the eyes of other people hearing these stories and I don't think they appreciate it. You know what I

Ryan Rutan: mean? Now they treat it like they distill it down again, like it becomes overly simplified. It becomes the thing that then earns compound interest that turns into success, right? And they don't really think through what that initial investment meant, it becomes a symbolic thing. It then turns into this amazing thing and that's what we get focused on. But if you actually break that down and you look at what those costs are and what that investment entail in terms of, you know, eating the, the mountains of shit to get there, we feel really differently about it. And it's one of those things where until you've gone through it, I think it's hard to appreciate. We can tell you how much it sucked until you've actually been through those moments of taking the face punch and you know, the, the cold sweats and staring at the ceiling. It doesn't land the same way, right? And I don't expect everybody to appreciate it in the same way that we're able to and certainly nobody's ever gonna appreciate it in the same way that Richard does because he lived through it. Right. To your point, the only people who really know these stories and can really appreciate them are the people that lived through them. Right? For the rest of us, regardless of how much empathy or sympathy we have. There's still only ever gonna be like a tangential connection to that we're never really gonna feel in the same way, but to your point, important to at least open our eyes to that, that aspect of it, right? Otherwise, we're completely missing out on 90% of the value of the story, right? And then became successful is not the important part of that story. That's the part that we like to focus on because that's the aspirational target that we set for ourselves. I want that part. Well, good. Get your spoon. Here's the mountain of shit.

Wil Schroter: There was a great high speech for the Heisman Award for college football this past year. Uh US c quarterback named uh Caleb Williams. And uh he, you know, he delivered an incredible speech, but what he said in the speech was pretty much sure I just won the Heisman. Let me tell you like what my journey looked like to get here and it wasn't awesome, right? He was like, basically, I've just been eating shit this entire time, right? And I was willing to do it because one day maybe I could be sitting up here. But guess what? There's a lot of people that aren't and he looked at the other three or four guys that were there, you know, all Heisman contenders. He's like, and it's funny all of them were going to the CFP, which for those of, you don't know, is the college finals for football. And he's like, and I'm the only person that isn't. So, you know, I guess I can't win them all. But the bigger point was he went through detail about being a kid about growing up about not being big enough, not being fast enough, not being all these things and, but wanting, you know, wanting and being willing to work for it so hard. And when he was telling the story, like what was going through my mind was every moment of friction he must have had and how little validation he would have had that any bit was gonna pan out, especially in the early years. Right. He's being

Ryan Rutan: told the opposite, in fact. Right. Yes.

Wil Schroter: Right. And then every time you level up to that next level, you see that there's a whole other echelon of people that are as good or better than you and you gotta start all over again. So I think that looking at people's stories, particularly in this case, founders and understanding like what grit they needed to have and more importantly realizing you gotta to do the same, you know what I mean? Well,

Ryan Rutan: I think it's funny, I mean, in how many other aspects of life. Do we treat what are essentially fables or stories? Right. And these are, these are true stories. But how often do we try to apply those as how to manuals? Right. Like you read Jack and The Beanstalk. Did you start planting shit all over your yard? Hoping you could climb to a fortune in the sky? No, that's ridiculous. Why would you do the same thing with some of these stories? Like the idea that this is somehow a pattern that can be followed and repeated is ludicrous to me. And I don't know why we tend to do this so much. We look for like, how can we copy what they did? You can't, right. Number one, you'd only have 1% of the details. Number two, you can't recreate it because that was a specific point in time specific product in time specific person with their own network, their own everything, right? This isn't a play that you can copy out of somebody else's playbook and run, right? This is an ad hoc narrative of, of part of what happened on their way to this thing, most of which wasn't deliberate at the time. That's the other thing that I love hearing is that, you know, sounds like I was doing something really smart, like, you know, we made this decision and that ended up being the thing. But at the time, it wasn't like, I think if we do this, this will lead to our inflection point, you ask most founders, those decisions leading up to, again, they didn't see it coming. They're like we were just making decisions like the other 1000 decisions we'd made before that, that had very little or no impact in the business. That was the one, but I didn't know that was gonna happen. Right. And Ergo, you can't either. You can't pick and choose pieces of my story and say I'll just apply those and I'll copy paste your result. Not

Wil Schroter: gonna happen, guys. You know his friends through this story a long time ago, I'm at this Forbes conference of some sort and it's me like a half dozen people uh like entrepreneurs speaking at this conference and we're in the green room and everyone's talking about kind of what they're gonna talk about up on stage. And this one guy was in the S a, a s like British Special Forces and he had a munition that was designed so that you could actually shoot people, people training and they could learn to fight through the pain of being shot. And I was like, where would you ever come up with that? He's like, well, during my time in the special forces, I had been shot in combat six times and I'm like, wait, what? Yeah, I, I was like, like at once he's like, no, on six separate occasions, I'm like, let me, let me get this straight. You got shot once doing your job and you're like, that's cool. Let's see if it happens again, then you got shot again. And you're like, how I ordered the chances it's gonna happen a third time. And I'm like, and at the third

Ryan Rutan: time you're only halfway there. Right. Yeah. Talk about a lesson. Nobody else wants to repeat to come up with a product idea.

Wil Schroter: Oh my God. Right. And so I asked him, I'm saying, so you got shot so many times, were you wearing like a magnetic bulletproof vest? And bullets were just like coming right at you. And he's like, here's the deal. We had lots of close quarter combat and in close quarter combat, you are going to get hit. The moments. People start squeezed off and fire bolts everywhere you are going to get hit. He's like most people don't die from the bullet per se. They die from bleeding out from the shock of the bullet. And he said, so what we were trained to do is fight through it. So when we get shot, just keep on fighting. I'm like, you're the biggest bad ass in the entire world. Like you're literally a superhero, right? And what fascinated me about the story. I didn't care about where his company had gone or how much they had raised or anything else like that. I just needed to hear about this guys when I used pain. I mean, in the most literal sense, but it was fascinating and I'm like, and so not only did you have to go through the misery of actually getting shot? I mean, me having to go to a class, I didn't want to go to seems meaning to that guy. But you went through this entire grueling experience that you apparently want to relive over and over and over by testing ammunition on yourself. And it was amazing to me and what I think is important is for us to not only empathize but dig in on that. Understand, not just the big success but understand and what it took to get through that pain, to fight through the pain, not his pain, please don't fight through that. But if you really, really, really wanna appreciate what it takes to build a company, understand the pain, not just the success. And I gotta say this, if you get an opportunity to hear one of these stories and listen to the person's pain and feel it with them, they're not looking for a high five, they're looking for a hug. So in addition to all the stuff related to founder groups, you've also got full access to everything on startups dot com that includes all of our education tracks which will be funding customer acquisition, even how to manage your monthly finances. They're so much stuff in there. All of our software including biz plan for putting together detailed business plans and financials launch rock for attracting early customers and of course fund for attracting investment capital. When you log into the startups dot com site, you'll find all of these resources available.

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