Ryan Rutan: Welcome back to the episode of the Startup Therapy podcast. This is Ryan Routan joined as always by my friend, the founder and CEO of Startups.com, Will Schroeder. Well, we are 300 episodes in, and we are still staring down one of those same questions that every founder faces early on, like, how do you lead? How do you do confidently when you've never done any of this shit before, right? Today, I think it would be fun like, let's go back in time, right? You started your thing at 19. I was right around that same spot. You were terrified to call yourself a CEO and a founder. I didn't even know I should call my, I think I called myself a president because I think that was the only time I knew at the time. Yeah, I was like, oh that sounds like the the the guy, right? Uh-huh. So let's let's unpack a little bit of the blueprint that you use to turn that just raw uncertainty into rock solid confidence, like one of those things that like everybody believes is like some people are just born with it, right? Or maybe it's Maybelline, right? No, it's, it's a practice skill, right? We get there. It's like, go back to the early podcasts, 300 podcasts later, you and I are super competent to do this because we've done it 300 times. First couple. Episodes, we were anything but. They're
Wil Schroter: terrible. I hated the sound of my voice. We wouldn't record video because we hated what we looked like on video. Like it was like it was so bad, right now we don't give a shit. If I were to look at this and I was talking to a founder, uh, last week, this is usually where these episodes come from. It's, you know, we interact with lots of founders and we hear things and we're like, oh, we should unpack that a bit. And I was talking to a founder and she was saying she's like, like kind of like, like kind of mid-thirties, so she's been at this for a little bit, right? You know, not like fresh out of college kind of thing. And she was like, I'm just starting to get my my Confidence. He's like, but you always, you know, for as long as I've known you, you've always been confident, right? Like, like that's cause I
Ryan Rutan: was already 40 when you met me.
Wil Schroter: You've always been old, but like she said, how did you get that way? And I was like, well, I didn't start that way. That's the part that I think is, is more like myth because I felt that I saw that myth like when I was starting at 19, Ryan, here's what I thought. I thought there was some oompa loompa factory of confident people where they just stamped these people out and they be. Came the cover models of Forbes, right? Like they just gave you gray hair and they just like made you the president of Bigo and you just had confidence. And I didn't know where it came from. I didn't know how it was developed, and I just knew that I didn't have it. Now what's interesting is, uh, you know, I was 19, so I wasn't even around long enough to know where you would get it. Like I just shown up to the game. But the other side of that was interesting was I also happened to pick a career that was startups, which was easily the biggest cauldron of insecurity you can possibly jump into. Yeah. And I think it compounds, and right when you talk to, when you talk to other founders, how often do you meet fully confident founders?
Ryan Rutan: Very rarely, I think in a lot of cases, when I do run into the very confident and early stage, the ones that look very confident, I think we got to draw a line between like confidence and hubris, right? There's a difference between between just thinking you know everything and actually knowing everything, but I think that, you know, I think this is and this is probably kind of a macro point to this entire episode, which is There's a difference between confidence and certainty. I think that as founders, one of the things that we're trying to say is like, well, I'm not confident because I'm not certain. Got to separate those two things, right? Because that person that you see who's just got that self-inflated confidence and it's not not real yet, that's not from certainty, right? It's just uncertainty well masked. You know, if you're trying to predicate your certainty or your confidence on certainty, this is where it starts to go wrong, right? This is why we're like, well, I just really don't know. So therefore, I can't come off confidently. Well, that's not where it comes from, right? It comes from trying and failing and doing it, all this stuff we're gonna talk about today. There's a road to answer your question very briefly, very few of the ones who I think are actually gonna go anywhere start off with a lot of confidence. They start off doing something else.
Wil Schroter: I agree. So when I was first starting, I had zero confidence. I'm 19 years old. I'm going to start an internet company when nobody had ever heard what the internet was. I was a horrible student, and I, and I only say that, not that that's totally. relevant, but I didn't have like the benefit of also being a star academic, right? So like some people, they come into the world and they're really good at something. Like our oldest daughters, for example, are just like genius and like they're just stacking up A's on everything that they do, which, which is the repetition, which is the repetition that builds confidence. I had none of that. I graduated bottom of my class in high school. I got rejected from every college I applied to. Like things weren't going well. Like there's not a lot of confidence builders going on in my life. So I assumed that, like I said, that there were people who were born confident. Those people became the confident people, like, like there's people that were born good looking, right? And that, that's just it, OK? And that confidence was just something guys like me didn't have. What I didn't understand was that's not the way it works. It's like building muscle. Yes, some people are just bigger than others, but generally it takes lots and lots of repetition, lots of dedication to build that muscle that is confidence. And so again, let's talk about the actual roadmap to do it. I think. For people who, you know, have developed some confidence and some experience that usually those go hand in hand, they'll appreciate what some of these categories are, and I think for people that are early in their career just, you know, kind of lack confidence, they're dying to know where these categories are like just point me in the direction of confidence, show me how to do this. So, uh, where should we start?
Ryan Rutan: When I said before that the the founders that I talked to, I believe we going somewhere, they don't start with confidence, they start with something else. And to me, I think one of the key ingredients to developing uh confidence over time is cur. Right? Curiosity leads to confidence, right? And it starts with the level of confidence to be curious in the first place, right? It takes some level of confidence to be curious to ask the question, because I think a lot of people associate asking with with weakness, and it's just not, right? Asking is not weakness. Asking power actually
Wil Schroter: authority. Yeah, it's power. It's how you do it, right? Like I had this thing early on when I was first getting started where I didn't realize it was like a superpower because I just, again, I Exactly what you just said. I associated asking questions with you don't know and you're stupid, you know, whatever, right? But at some point, I got so good at asking questions that it put me in the power position when I walked into a room. Here's how it works out. I'm 19 years old. I've still got pimples from high school, right? Like I, I, I do not look like someone with authority at all, and I was
Ryan Rutan: not briefcase with nothing in it. Very exactly
Wil Schroter: my very ill fitting suit, my empty briefcase, like I was is is gross and and at a time. time when young CEOs didn't exist, so like nobody was giving me credit that you might be Mark Zuckerberg. I didn't think he was born yet. I walk into a room and what came across as natural curiosity when I would talk to clients, I would say, well, what does work for you, right? Because I didn't know. I actually had no idea how their business worked, right? So I would just ask, so, so what does work for you? And they would say, well, you know, um, we sell really good to this constituents really well with this constituency or this, this, um, demographic. I remember I didn't know what that word meant. And, and I'd like, so what does the demographic mean to you? Literally ask you, explain to me in the middle of a meeting and I'm a marketing to me. How do you define demographic? It turned out that when I was asking questions, I had the room. In the same way a prosecutor in a courtroom asking the questions has all the power, because when someone's asking you a question, it puts you on the defensive in a strange way, right? Not that they're trying to, but it puts you in a position where you're the one demanding an answer.
Ryan Rutan: You get to steer. You, you have the helm at that point.
Wil Schroter: And that's one thing where it kind of gives you a little bit of power, and that that's great. But more importantly, you're learning, right? You find out what a demographic is, you find out it's pretty important when you're gonna start a marketing agency. And when you get really good, just naturally at asking questions of everything, of everything, dude, right? In other words, like, hey client, how does your business work? Hey, employee, why is it that you do things that way, right? Hey, advisor, how is it that you got to this outcome and how would I do the same? Pepering everybody. And by the way, Ran, it's exactly what I'm doing right now, right? As you know, I, I, I specifically with building this house, you know, some of our Listeners know I'm in the process of building a house. I knew nothing about how to build a house, right? Nothing about how to build a house. But I, I've always wanted to build one that's been a huge passion of mine, but exactly this skill is what gave me the confidence to do it. So I was like, I want to design the house. I want to, um, build everything inside the house, and by the way, I don't know how to build any of these things. So I want to become an architect, a general contractor. I wanna become a cabinet maker, I want to become an electrician. I want to become a network installer. I want like all of those things, and I wanna do them at the same level or better as the people who do them, and I wanna do it on the scope of an office building. And the way I did it, I would get involved with these trades and I would say, well, what about this? Well, what about this? Well, what about this? And they're like, damn, this dude asks a lot of questions. That's how I learned. Cabinet cabinet guy would come to me and say, Hey, this cabinet's gonna this kitchen's gonna cost $100,000 to make a number, right? And I'd say, what? What do you mean why? Like, literally, line by line, what are all the costs that are involved in getting it to there? And he's like, oh, you know, you, you have to use this material and this material and that. And I'm like, well, why do you have to use that material? Couldn't you use another one? annoying as fuck, right? But that's what made me confident because you can ask as many questions as you want.
Ryan Rutan: A couple of things when I went back to like, especially the early days, right, when I was back in that lacking confidence space, one of the things that occurred to me was that I didn't feel comfortable asking questions, and then I started. Look at the type of questions I was asking. Well, I think part of it was this like illustrating that I don't know what I'm doing, right? It was that the whole thing of like, I don't know what the word demographic means. I don't want to ask that question right now. And then I looked at the way I would have asked the question. So the way the question has sort of appeared in my mind that kept me from asking in the first place. And a lot of times it was the what questions, right? What do you mean? The why questions on the if you just reframe it as why, like, what is demographic? That's a problem, right? If you're about to hire somebody who probably should know the answer to that. But if you ask, like, to your point, why? Why is this important to you? Why does this matter? Why do you feel like this is the key thing for what we're doing right now? All of a sudden it goes from being somebody who you're like, oh, they don't know what they're talking about to, oh, insightful question with a couple of words changed, right? So a big part of this, I think for if you're if you're still in that position where you're struggling to feel confident enough to even ask the question, ask yourself, are you asking the right questions, you're wording the question correctly because simply rewording the question, reframing the question in so many cases, takes you from sounding like somebody who has no idea what. Talking about to somebody who's sitting in a position where they can ask down upon the ye of little knowledge, right? Right, right. Well, why would you do it that way, right? All of that contractors like, they don't know, they don't know that you don't know. What they know is that you're, they're being questioned about their methodology. They're being questioned about how they're going to approach something, right? They have no idea what your reference level of knowledge is.
Wil Schroter: Also, people love to talk about themselves, right? Like that's the ninja moved there, right? Like when I was single and I. Go on dates again, naturally curious. I would just ask my date a million questions, right? And she would come away from the date being like, wow, like Will's a super engaging, like, you know, interesting guy. Yeah, because we just talked about you the whole time, which was fine, right? That that was my preference, right? I
Ryan Rutan: know nothing about
Wil Schroter: him.
Ryan Rutan: Yeah,
Wil Schroter: literally like I would remember I'd come back from dates and I think I laughed to myself like, this girl actually has knows nothing about me, a single remember my name, but I know like like, like her relationship with her dad and everything else like that. Yeah, I
Ryan Rutan: have an FBI level dossier on her.
Wil Schroter: But I think it's a superpower. There's nothing unique about it, you either use it or you don't.
Ryan Rutan: Yeah, that and that's the thing like it isn't it it's also not a complicated superpower, right? It's not like the ability to do complex mathematical calculations in your head. Anybody can ask a question. Yep, anybody can ask a question. And again, like there are some probably higher level formulations of certain questions. Kind of doesn't matter at the end as long as you're asking, you're probably learning. Let me ask you this though, at what point, and maybe this is more of an internal thing, so like, because one of the places I like to ask a lot of questions is internally, right? With within the team, right? you're starting to lead, right, this isn't all. Just outward facing stuff. As you get to the internal, we're trying to lead the teams. We're trying to be confident in that leadership. At what point do you feel like you crossed the line from learning and growing into slowing things down? Like, at some point, like if you just keep asking your contractors questions at the house, they're not building anything because they're just, you're just asking like how do you balance those two things.
Wil Schroter: There's a limit to how many questions that are even reasonable, right? Like if you think about it like this, if we were to,
Ryan Rutan: not if you're my 7 year old son, no, sir, absolutely not. He knows no boundaries.
Wil Schroter: Insane. If you stack rank the value of questions, and let's say I've got 10 questions, the 1st 3 questions I'm gonna ask have 70% of the value of what I need to know, and the rest I may not need, right? So I always think about it like, let me get the the first big ones out of the way and see if the other ones are necessary.
Ryan Rutan: Oh, on occasion though, I don't know if you find this, but on occasion though, the thing I think like the top three, there ends up coming out like some nuance in the answer that ends up being like absolute gold somewhere, like not even within the top 3, but like somewhere where like. Becomes a follow on question
Wil Schroter: in interviews, right? When you're interviewing people, most people aren't naturally curious or or empathetic. I'm paraphrasing, they generally don't give a shit about other humans. So when they interview, they're really bad at interviewing. They don't pick up on social signals. They, they don't understand how to like double click to the, the why behind that. I'll give you an example. Years ago, I stumbled upon my favorite interview question because I was naturally curious, right? I'd heard a couple of previous interview people, these were developers back in the day. Right, kind of bitching about their current companies, and I thought to myself like, man, the person I want to hire probably isn't the person that's gonna like sit around bitching about my company. Instead of like the generic interview question, which was something along the lines of, you know, where do you want to be in 10 years kind of thing. I would ask the question, what did you dislike about your current job that you would never want to do again? Open up the door, open up the floodgates to complain. now.
Ryan Rutan: And then, and then listen to them recite the job description to you and you're like, OK, pass.
Wil Schroter: I never want to work with people. I don't wanna work with annoying bosses. I'm like, oh, you're not gonna work out here at all. What's interesting is the value of where you can go with questions. What it allows you to do as it relates to building your confidence. Once you know that you can ask questions, it allows you to go into any situation and be armed and ready, right? So I can go into like, again, giant house that I'm building and be like, hey, I don't know anything about how, you know, plumbing works, right? But I'm about to. Uh, and I, and I know because I know I'm good at investigation and questions, uh, that I can make that work. When I do meetings with people, just like, you know, meetings with random people that I've never met before, we're doing a lunch or dinner, you know, whatever the occasion calls for. I know I'm gonna ask them 1000 questions and so I'm never nervous walking into a meeting, even if I have no idea who this person is or what the background is, because I've got the arsenal, the tool belt to learn everything I need to know on the spot when I get there and it's powerful, um, and it built a huge amount. confidence for me. All
Ryan Rutan: right, so, curiosity, superpower, questions, super tool, this is how we begin to build that confidence. So as we start to grow that confidence, so now we're, we're learning some stuff. Let's talk about what happens when we actually start to, to do some things, right? Because there's, there's, we start at that point where it's like, OK, I don't know how. I don't know anything, right? And then there's the, I'll figure it out moment, and then you start asking the questions, you start learning, but then there comes a point where it's like the, OK. I didn't know how. I do know how now, but I haven't done it yet. So then we gotta get to the part where, OK, I'll figure it out. I'm gonna go try it. I'm willing to make the attempt.
Wil Schroter: I don't think a lot of people understand that confidence, like we said earlier in the episode is a conditioning exercise. I mean, you get something constantly conditioning that muscle. We look at it like this confidence is a destination a mile from here, and I just don't know how to walk a mile, you know, get a mile. Like, no, you don't, right? You will. Someday, if you start with walking 10 ft, and tomorrow you walk 11 ft, and the next day you walk 12 ft, and you just keep chipping away, and what that looks like here, and I didn't know this at the time, I certainly know it now, and watched countless founders through the same journey. It's all these little wins where you challenge yourself to do something that you didn't think you could do. Let me give you an example. Yes. So I'll I'll stick with with me early in the agency days cause that was just younger part of me. I remember like when. The earliest meetings I was in, this will give you this gives you a sense for how old we are. The the client said to me, there's this new thing, hold, hold your head, there's this new thing called e-commerce, and I remember, I remember he emphasized the E because it wasn't just commerce now, right, it was called e-commerce and I was like, er, do you mean electronic commerce? He's like, yes, yes, we want electronic commerce. I mean, I'm, I can't even make this up like. It was this stupid, but again, it all has to start somewhere. So he's basically said, I wanna sell shit on the internet. But at the time no one was selling stuff on the internet, like it really wasn't a thing, right? This is like 94, like, you know, people would start, but this was early, and I certainly had no idea, no idea um how to sell something on the internet, but I remember the context of the meeting. This client was so excited. That they wanted to do e-commerce, that I was excited, and when they asked if I could do it, I was like, yes. Now I didn't say it because I was trying to lie. I said it because he was so excited about it. I felt like ashamed that I couldn't like answer go figure it out, right. So far I hadn't like figured out a lot of things in life yet. I'd figured out a few, but like, not like this, where there was like a very intentional call to action where a human was saying. Can you do this by this date and I will pay you or not pay you. And I was like, oh shit, yes. So I say yes. Long story short, I end up going and finding the resources. I found a developer that that could, that could build e-commerce, uh, funny side story, Ryan. The person that I found had, uh, there was a letter to the editor about Joel's textbook exchange, and he was like, hey, I hear you can sell, I hear, I hear Joel is selling um textbooks on the internet. Is that a new thing? Is that possible? I mean, how funny is this, right? It turned out the person that was asking about it was Joel from Joel's textbook exchange, and he, and he, he sent a letter to the editor of the campus newspaper to essentially have them print an ad about his bait, yep, there you go. So I somehow, I somehow got a hold of him. I was like, well, if you know how to do a textbook exchange, then you know what a shopping cart is, right? And he was like, yeah, sort of. I was like, can you build one? And he said, yeah, I was like, you're hired. He's like my first employee. But but we got it done. We shipped the e-commerce, and I was like, oh, so part of growth is challenging myself to do things that I couldn't do yesterday. Hm, I wonder if this will ever come up again, like 10.
Ryan Rutan: I mean like I this goes back to something I was saying earlier, right? It's not about certainty. Confidence isn't. Only aligned with what you've already done. It's about what you believe you can do next, right? If again, if we fix confidence to just what we're certain of, like I've already done this, so I can do it again, you're gonna miss out on most of what it is to be a founder, cause we have to go do a bunch of shit that's never been done before. That's the whole point, right? So it's not about, yes, of course, having done something that leads up to that, right? If you'd never built a website at all before saying yes to build. e-commerce might have been a step too far, right? But you've taken a bunch of little steps up to that point, right? Like, hello world, I coded some HTML all the way through, you know, building, you know, multi-page sites and, and, and complex navigations, all this stuff. And then you're just layering things on. So back to your point, it's a lot of little victories that start to stack up into, OK, what's the next thing that I need to do that I haven't yet that I'm not sure how to, but that I believe I can. That's confidence.
Wil Schroter: That's what I'm doing with my kiddos now. What I'm teaching them are these micro challenges. They have the benefit of their dad giving them a very deliberate framework. Like, I'm not just saying, hey, randomly do this, I'm like, this leads to this. And fortunately my my kids have a very natural appetite for this stuff, right? They they they like challenges. And so what I explained to them, I said, in order to get from here to there, it's not one step. It's a 100 steps in that direction, some of which take you off path and some of which put you back on. But the goal is to just keep chipping away at steps. So, as this relates to to our community, to our founder community, take a look at what you're going to do today, tomorrow and ask. Yourself what you're doing right now. Where could you be challenging yourself more, right? This is a bit of a meat heady example, but if you're bench pressing, and you're normally gonna bench press 185, put 205 on the bench and just press it. And part of you is like, well, I can't do that, and you never will until you put it on the bar and try. And and that's the point. You have to intentionally keep pushing yourself further than you could you would otherwise go. In order to level up. 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. We talk about this. 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.
Ryan Rutan: Let's stop for just a second, and I want to talk about the line between ambition. And recklessness, right, like between well served confidence and and and hubris, right? So going back, like you said, you know, you hadn't done that thing before I done e-commerce before, but you'd heard about it, you knew it was sort of possible. There was some talk about it, so this wasn't coming out of thin air. But like, for founders who are facing these situations where it's like, what can I feel OK attempting? What can I feel good about trying? How do we start to draw that line?
Wil Schroter: I think we started at the the very least is if again. Uh, pardon my meathead bench example, but, but if my bench is 185, if I don't do something that's incrementally more than that, I'm using the bench example just because it's very numeric, right? If I don't put more on the bar to try, I will never get further, OK? Now, do I put twice as much on the bar and crush myself? No. The the idea is that I'm pushing a little bit further. So this is again in the client world, I'm making a slightly bigger commitment than I would have time for right now. That's actually how you grow. In the, um, the product knowledge. World, right? Let's say that, um, part of what you need to do as a founder is you need to become um adept at learning finance, OK? No, you're not gonna become an entire CFO, but you can learn how an income statement works, right? You say, I'm just gonna learn the basics of where income goes, where expenses go, and how profit ever happens, right? That's it. I'm not gonna try to learn more than that. But that's more than I know right now. That's 10 more pounds on the bar. That's how you do it.
Ryan Rutan: What about the the case because I totally get the case for incrementality, right? And I, I teach this all the time. We talk about this all the time. If you've never tried this, don't dump $10,000 into it the first month. You've never tried this marketing channel, you've never worked with this developer, just like try to take little little bites. What about the case where we're about to engage in something that we've not done it all before, and there are plenty of these things in them, and we don't necessarily have any incremental bar to work from, right? Because let's let's use, let's use your your bench example. I have never bench pressed in my entire life, which It is nearly true. I've done it a few times, but not very many. So, if, if you say, can you bench 205, I either have to say yes or no. I don't have anything to base that off of. I don't know if I can bench 185, so I don't know that 205 is a stretch. Yeah, how do we approach that?
Wil Schroter: You start with the bar, you start again, instead of saying I can't do it at all, you start with what's the smallest thing that I can possibly do. And I have found this is Ryan, this is my absolute superpower that I've owned. So incredibly well, especially over the last few years, again, as we were talking about building this house, when we're doing the architecture, this is like so specific. Like when we were doing the architecture, I was watching the architect and like going through the ideas, and I gave him like a caveman painting, and he gave me back something that looked nothing like what I wanted, not even remotely close. And while I was watching him do what they call the massing, which is when they're coming up with the initial concepts. I was working with their um their 3D modeler, and 3D modeler goes in the 3D program and does, you know, some renderings. And I was like, how do you do that? The guy, this is question guy, right? I was like, what are you using? He's like, I will use a program called Sketch Up. I'm like, oh, OK, that's interesting. I've used a little bit of sketch tomorrow morning. Yeah, exactly. I'm like, so I'm not gonna be able to just like jump in this program and become an architect, right? Like it's just not how it works. But you know what I can do? I can jump in this program and Ryan, I remember when I showed you sketchup, I was like, the first thing you need to do is draw a box. That's it. Draw a box, right? um and
Ryan Rutan: extruding in any direction you want. Again,
Wil Schroter: this sounds so tiny, but this is exactly how this is, this is the, the, the hidden move to all of this. I was like, OK, I just need to draw a box and every house is just a. Series of boxes, right? It becomes more. But once I know how to draw one box, I can draw another in another in another, and I'll draw better boxes over time, so on and so forth. Uh, my daughter, uh, I, I haven't told you this yet, is about to teach me guitar. She's been taking lessons for years. She's fairly inept, right? And
Ryan Rutan: you sitting in the corner back there. Well, it's been, is that, is that thing moved in 10 years?
Wil Schroter: That actually is a prop. It's a real guitar, and I have no idea how to play it. And people ask me all the time, like, 00, you're a musician? I'm like, I'm not. I'm just a guy that happens to have a guitar in the back of his his office. And when we sat down on this weekend, she talked about it, she said, Dad, uh, you know, I really want to teach you how to play guitar. I said, teach me one chord, just like start there, and I'll play it over and over and over, then teach me two, right? I think Ryan, this is a long way to answering question, but I think when people try to learn or do anything, especially when it comes to being a founder, they try to do too much. And by way of that, they don't do anything at all. They get on the bench and they, they try to push 185 when they should be pushing 35, and they're like, oh, I can't bench. No, you can't bench that much because you haven't started with 35. Yeah. Yeah,
Ryan Rutan: we see this in so many different ways, like fundraising is probably a really easy one to pick on here because people come in like, I need $5 million to build everything I ever want to build. OK, cool. $5 million dream house. What does pitching a tent on the land look like, right? How can we just occupy the space? What's what's the least you can do that will make a meaningful difference between where you are today and where you could be tomorrow? Yep. And I think that it's just, it gets really hard because again we we spend so much time pitching the vision and putting confidence. Behind that and showing how big and wonderful this thing can be, that we forget that we have to talk big but act really, really small, and it just makes life so much easier, right? I think every week I see at least two founders between my Monday and Friday sessions who come out with what, you know, an amazing plan, lots of stuff, really cool things you're gonna accomplish, but they are biting off way more than they could possibly chew because of that, they don't really know where to start. They don't have the confidence to start because they're like, well, there's just so much. I'm like, well, there isn't really, to your point, yeah. A full architectural rendering is a shit ton of stuff. It's a lot of work. Started with a box
Wil Schroter: or it started, yeah, I got asked this question yesterday. I was on site, we were going through inspections, you and I were talking about this, and the electrical inspector was like, wait, you designed like all the electrical in this house, like and it's, it's a super complicated house. I'm like, yeah, and he's like, how? I was like drawing lines one circuit at a time, right? Like I understood what a 15 a circuit was. I was like, oh, I'm gonna need another one of those. Oh, it turns out every every light circuit is. Typically 15 amps, so I'll just uh copy paste that to, and I was like on and on, and I learned one circuit at a time. He was like, that seems super obvious when you say it, but I would have never thought to do it like that. I was like, that's why it's a ninja move. All right, so, so, uh, let's keep going. So I, I would say in making those big plays, I think making enough of the small ones, Ryan, is what gives you the confidence to make a big one, right? And then sometimes you don't even realize you're making the big one until, you know, until it becomes something else.
Ryan Rutan: Sometimes the big One just really isn't obvious because it is just a collection of the small ones. But, but I, I think that's it. So let's, let's back up for a second, right? So we started with, we started with curiosity and saying that like asking the questions, curiosity, uh, starts to build some of that early confidence. And then we have to go between the curiosity and the actual action where we say, OK, now I'm gonna, I'm gonna, I'm gonna take what I've learned. I'm actually gonna do something with it. The next thing that I think is that that ends up needing to happen is that we got to get really good at being wrong, right? Which is to say that like a lot of those. Little things that we're gonna go try is they're not gonna work and that's OK, right? Because true confidence, again, I'm gonna say this, this will be the last time I say this today. True confidence is not certainty. It's resilience in motion. This is what it is, right? Confidence comes from saying, I don't know, but I'm willing to find out. I found out and I'm willing to try. I'm willing to try and I'm willing to be wrong and sometimes get it right. So that's what I want to talk about now. I want to talk about like, how do we get good at being wrong? I found it easy, comes
Wil Schroter: naturally to me. Well, I got the wrong part down pat. Um, yeah,
Ryan Rutan: I'm super good at it.
Wil Schroter: When you're going into your career, how did you see being right versus being wrong like that it's like what would have told you that it's OK to be wrong?
Ryan Rutan: Yeah, you know, interesting because not a lot, I think as I entered my career, nothing in fact. I've talked about this before, but, you know, we came from like an achievement household and performance culture, right, performed well in school, was a was a, you know, strong student athlete. Merit scholar, all that stuff, right? And that was what was celebrated. So it was always like, what's the standard? Pass it. Don't be wrong, be right as much as you can. There's a real penalty to being wrong. Get to university, it's the same game. Everybody's, you know, vying for some level of of outcome at the end of that, and that's related to how well do you perform here, right? So none of it was, was, was taught as I was, you know, being prepared in the traditional way. Contrast that to the fact. That I had started multiple businesses, you know, from my lemonade wagons to lawn mowing to snow removal to the cattle company to the little software database and and practice management system that I built up into university when I began my digital agency at 19, right? Those things were were what taught me it was OK to be wrong. sometimes in extremely brutal ways, right? I think I've shared this one before and I'm I'm not proud of this, but one day I made a decision between Going out to feed my cows, uh, when they were still very, very young and I needed to bottle feed them at this point
Wil Schroter: back up just so everybody knows, Ryan, you're not being metaphorical right now. You're from
Ryan Rutan: not being metaphorical. I was literally, I used to, I, I found an arbitrage play where I could buy male dairy calves from dairy farmers for $10 apiece, put $50 worth of milk replacer into them, put them out the pasture, bag of grain for $25 and sell these things for 700 to $800 right? So at 10 years old. This was a fantastic
Wil Schroter: business in a big
Ryan Rutan: level up, a huge level up, right? But so I, I decided one morning on a Saturday morning that I didn't want to wake up at 5 o'clock so that I could go feed before I went to basketball practice. And I thought, I'll do it after basketball practice. Well, you may know, Will, basketball is a winter sport, winter is cold, um, and young animals are very vulnerable. I came back to find one of my 5 dead. His name was Star. I was still naming him at that point. That's how, that's how tender and naive I was. do that. Um, and, uh, so I learned the cost of being wrong. I learned the cost of being wrong there. But I also learned that that is gonna happen sometimes. You're gonna make decisions and it didn't stop me from doing it, it didn't stop the other four from being viable. It didn't stop me from making money that year. It didn't stop me from deciding to buy more the next year. Um, and so I think it was all those little things, man, you just start to stack up this, this ability of being wrong.
Wil Schroter: I think we came from an era of bravery. And when I mean bravery. I mean, bravery being like you have to be brave and bold and right, and that bravery was an attribute of being right. And here's
Ryan Rutan: a BMW or here's a BMX bike kid, go prove that you're brave, right? They, they were given challenges
Wil Schroter: and please don't worry, don't have it. Um, it reminds me of a great quote, and of all the places that quote comes from, it comes from one of my favorite games, which is the Civilization series, right? I do not want to recount how many hours I have on Steam to civilization. But it's probably longer
Ryan Rutan: than I'm actually wondering how many people you have working on that simultaneous, because it's more hours than you've been alive.
Wil Schroter: I seriously, as if I'd never slept. There's a quote that that pops up, you know, whenever you hit certain milestones, and I mean, I'm such a nerd that I can tell you it's the military tradition, uh, civic, and, uh, the quote is bravery is, is knowing you're the only is being the only person that knows you're afraid. And I love that quote. Bravery is a person that knows you're afraid, and I think that goes to that that speaks to what we're talking about, right, which is this idea that I'm brave enough to be wrong and I'm the only person that's willing to admit that I. Oh I do what's happening, right? Like, I felt the more I could be brave by being wrong, the more unstoppable I became, right? I, I, I, I really genuinely genuinely believe that as I get good at making mistakes, like you're talking about, I was like, oh damn, if I'm willing, like, you know, Ryan, you and I are working on some landing pages right now, if I'm willing to just try them all and not try to have the right answer and just let the answer find me by virtue of elimination, I am unstoppable. That doesn't mean I'm, I'm gonna be the. Victorious. It means the opposite where I'm afraid to make decisions or take leaps. I'm afraid to be brave because I'm afraid to be wrong, yeah,
Ryan Rutan: which isn't, yeah, which isn't really competence. I mean this is one of the things where like I think I, I talked about this earlier, the difference between confidence and hubris. Bravery is, there's still a belief that you can, but it's based on something, right? as as somebody else famously said, the difference between bravery and stupidity is the outcome, the outcome, right? We know, we know after the fact, but I think it does. It takes a level of confidence. To say, yes, I'm willing to try this. It takes a bigger level and a more important level of confidence, I think, to say, and I'm willing to live with those, with the consequences of being part of it for sure. Just a couple weeks ago, we had a little situation at school, and my, my seven year old comes to me and he's he's visibly upset and as he starts to tell me the story, he starts to cry and he's telling me about something where a thing happened and he tried to intervene and then through the intervention, he got in trouble, uh, for standing up in the. way that he did it, we talked about all the the ways he could have kind of softened his response a bit, but that wasn't really important, right? He goes, at some point he says, but wasn't it brave to try to do the right thing? And I said, yes, it absolutely was brave to try to do the right thing. It's like, but bravery doesn't stop there, buddy. You gotta be brave enough to accept what happens. The minute you say, yes, I'm willing to try this, yes, I'm willing to do. I'm willing to jump. You've got to be willing, you have to be brave enough to accept what the fall feels like. Not sure that landed all that well with the seven year. Maybe he'll remember it someday, but that's OK. I said it. But shook his head at the time, and he stopped crying shortly thereafter.
Wil Schroter: Given what we do for a living, specifically as founders, I don't know that I'd give the same advice to doctors, right? Ah, just get some surgeries out there, see how it goes. You're gonna be wrong. You're the wrong valve, yeah, you know, like whatever, um, yeah, or or legal, you know, file some motions and see where it goes, you know what I mean, yeah, like, uh, not quite the same thing, but for what we do because there is not a certain. Path in most of what we do, you can't be the person that always does the surgery right or, or always wins the legal argument. That actually doesn't work in our business. So if you want to be good at what we do, which is jumping into the unknown with no possible knowledge of what the answers are going to be, which is all of us, by the way, right? That's not specific to like, you just happen to not know because you're 22 years old. It's no one knows because you're going to a market with a product that's never been invented before, a market that doesn't exist in a. That's never done it before. How do you possibly know what these answers are? So in order to be able to have the confidence to, to go through that, you have to be able to say, oh no, right? I actually don't know what the answer is gonna be, but what I'm gonna do is I'm gonna try every version until the right answer presents itself and be good that be good being confident. We may fail. We may try everything and everything fails. It happens. Ryan, you and I failed at a million things, we just do, right? But I think our perseverance toward failure is what helps us unlock the things that work.
Ryan Rutan: It absolutely is. I mean, this is where the learnings come from. I, I know that like fundamentally people get this, but I think we can, we forget. And again, I'm gonna go back to something I referenced earlier, which is we get so used to having to pitch. So let's let's, I can tie this back to like an investor pitch, for example, where we have to be so certain of ourselves, we have to present this future that clearly doesn't exist yet. We got to go make it true. We need somebody's money to go do that. And so I think one of the questions that founders seem to struggle with is like, how do they stay credible with your team, with your partners, with, you know, your clients, with investors. sort of openly admitting uncertainty and and I just saw this done really well, a couple weeks ago now. Founder was sharing the deck with me, they ran me through the pitch. They openly exposed a bunch of places where we thought this would be true, and it wasn't at all. We were completely wrong. And here's what we learned, and here's how we're doing it. And then here's what we also we did wrong, and here's what we learned from that, and here's what we're doing with that. And they did such a beautiful job of showing the vulnerability and showing and building credibility by saying, yeah, we screwed this up. Because of course we did, because there was no right answer to this at the time. We had to go seeking the answer, right? Now, I think if you're doing things like, you know, like you're making silly mistakes, sure, what would a silly mistake look like? Like, well, we're only going to accept PayPal. You're an in-person cafe. That might be a weird choice, right? That somebody could give you advice on that. You don't need to go try that to figure it out. Somebody else is gonna tell you, no, probably just get a normal POS like everybody else does, it'll be fine. But that's not most of the type of decisions we're dealing with as founders. It's things that we. Don't know, and that quite possibly, neither does anyone else because we're doing something nobody's ever done before, and that's OK.
Wil Schroter: We've got chip away the the way I see it, right, like, confidence is built, not born. It is a muscle that you have to develop. So when folks think about like, I want to be this confident leader, awesome. The way you do that is 1% at a time. It's not like a, uh, you, you flip a switch and you wake up tomorrow and you are a confident leader. Every confident leader became a confident leader because They were willing to put themselves out there, they were willing to ask questions, they were willing to challenge themselves, make those big plays. They were willing to be wrong so many times, so they could have the advantage of being right. And over time, with enough big plays, with enough uh confidence that they built, they chipped away at, they became the leaders that you see today, the people that stand up and can say this is what the future is, because I've built it before, because I've tried everything before. So I think for a lot of folks that are thinking about, hey, I'm not confident enough, that's OK. That's OK. You won't be more confident tomorrow. You will be 1% more confident tomorrow. If you challenge yourself and ask the questions, but over time, if you keep chipping away at it, like anything else in life, you will become exactly the leader you need to be, and one day you're gonna wake up and you're gonna look around and say, I am confident as hell, hallelujah.
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.