Forging Founder Confidence

Welcome back to the episode of the Startup Therapy Podcast. This is Ryan Rutan joint, as always by my friend, the founder, and CEO of startups.com. Will, Schroeder will, 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? You've never done any of this shit before. Yep. Right. Today, I think it would be fun is like, let's go back in time. Right. You started your thing at 19.

I was right around that same spot. Yep. 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 title I knew at the time. Right. That thing. Yeah. Yeah. Yeah. I was like, oh, that sounds like the, the, the guy, right. Uhhuh. 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.

Because like one of those things that like everybody believes is like, some people are just born with it, right? Right, right. Or maybe it's Maybelline, right? No, it's, it's a practice skill, right? We get there.

It's like, look, go back to the early podcasts, 300 podcasts later. You and I are super confident to do this because we've done it 300 times. First couple episodes we were anything but they're terrible. I hated the sound of my voice. We wouldn't record video 'cause we hated what we looked like on video. Like, it was like, it was so bad. Right now we don't give a shit.

Yep. If I were to look at this and, 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 were like, oh, we should unpack that a bit. And I was talking to a founder and she was saying she's like, like kinda like, like kinda mid thirties. So she's been at this for a little bit. Right. You know, not like fresh outta college kinda thing. And she was like.

I'm just starting to get my, my confidence. She's like, but, but you've always, you know, for as long as I've known you, you've always been confident, right? Like, like that's 'cause I was already 40 when you met me. 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. Yeah. 'cause I felt that, I saw that myth like when I was starting at 19, Ryan, here's what I thought.

I thought there were some Oompa lump of factory of confident people where they just stamped these people out and they became the cover models of Forbes, right? Like right. They just gave you gray hair and they just like made you the president of BCO 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.

You know, I was 19 so I wasn't even around long enough to know where you would get it. Like I had 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? 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 gotta draw a line between like confidence in hubris, right? There's a difference between, between just, I have plenty of that thinking, you know, everything and actually knowing everything. Yeah. But I think that, you know, I think this is, and this is probably a kind of a macro point to this entire episode.

Which is, there's a difference between confidence and certainty, right? 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. Gotta 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? Right. It's just uncertainty, well masked. And if you're trying to predicate your.

Certainty or your confidence uncertainty. 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. Um, there's a roadmap. 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, right?

They start off doing something else. 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 geniuses. Yes. Like they're just stacking up as on everything that they do. Everything, which is the repetition talent across the board, right? Which is the repetition that builds competence. 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 were not a lot of confidence builders going on in my life.

And 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. Okay. 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. Yeah. And 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, kinda 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? When I said before the, the, the founders that I talked to, I believe are going somewhere, they don't start with competence, they start with something else.

And to me, I think one of the key ingredients to developing cur uh, competence over time is curiosity. 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. 'cause I think a lot of people associate asking with, with weakness and it's just not right. Asking is not weakness. Asking is power's actually authority? Yeah. 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, or you know, whatever. Right. But at some point I got so good at asking questions, I. That it put me in the power position when I walked into a room. Here's how it worked out. Percent. 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 not fitting suit briefcase with nothing in it. Very exactly. My very ill-fitting suit, my empty briefcase. Like I was, it is, it is gross. And, and at a 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 constituent really well with this constituency or this, this, um, demographic. I remember I didn't know what that word meant. And, and I'd be like, so what does the demographic mean to you? Literally ask you.

Yeah, that's it. Explain to me, in the middle of a meeting, and I'm a marketing company, define this to me. Yeah. 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. Yeah. Because when someone's asking you a question, it puts you on the defensive in a strange way. Right?

Not that they, they're trying to, but it puts you in a position where you're the one demanding an answer. You get to steer you. You have the helm at that point. 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 that'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. In other words like, Hey client, how does your business work? Hey, employee, why is it that you do things that way? Hey, advisor, how is it that you got to this outcome and how would I do the same? Peppering everybody? And by the way, Ryan, it's exactly what I'm doing right now. Yeah. As you know, I I, to this day specifically. With building this house.

You know, as some of our listeners know, I'm been in the process of building a house. I knew nothing about how to build a house, right? Nothing about how to build a house doesn't matter. But I re I've always wanted to build one that's been a, a huge passion of mine. But exactly this skill is what gave me the confidence to do it. So I was like, I wanna 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 wanna become an architect, a general contractor. I wanna become a cabinet maker, I wanna become an electrician, I wanna 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. Yeah. And I put 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. I. Cabinet. Cabinet guy would come to me and say, Hey, this cabinet's gonna, this kitchen's gonna cost a hundred thousand dollars to making a number. Right? And I'd say, why? He's like, what do you mean why? Like literally line by line. What are all the costs that are involved in getting it to there? Yeah. And he's like, well, 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. Yeah. Because you can ask as many questions as you want. A couple 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. Right? And then I started to 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 dunno what the word demographic means. I don't want to ask that question right now. And then I looked at the way I would've asked the question.

So the way the question has sort of appeared in my mind that kept me from asking in the first place. Okay. And a lot of times it was the what questions, right? What do you mean the why questions on the end? 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? Sure. Why does this matter?

Why do you feel like this is the key thing for what we're doing right now? Right? All of a sudden it goes from being somebody who you're like, oh, they don't know what they're talking about to, Ooh, insightful question. With a couple of words changed, right? Yep. 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?

Are you 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 they're talking about, to somebody who's sitting in a position where they can ask down upon the ye of little knowledge, right? Where it's like, right, right. Well, why would you do it that way? Right? All of a sudden that contractor's 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. Also, people love to talk about themselves, right? They sure, as should do. That's the ninja move there, right? Like when I was single and I'd go on dates again, naturally curious. I would just ask my dad a million questions, right?

Yeah. And she would come away from the date being like, wow, like, Will's a super engaging, like, you know, interesting guy. Yeah. 'cause we just talked about you the whole time, which was fine. You the whole time, right? That's, that, that was my preference. Right. I know nothing about him, but yeah, literally, I, like, I would remember I'd, I'd come back from dates and I'd think to my, I, I laugh to myself like, this girl actually has, knows nothing about me, nothing about it.

Didn't ask a single person. You might remember my name, but I literally like, like her relationship with her dad and everything else like that. Yeah. I have an FBI level dossier on her. Yeah. But I think it's a superpower. There's nothing unique about it. Either use it or you don't. Yeah, that, and that's the thing, like it isn't it, it is 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 at what point. 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? Yeah. As you're starting to lead a hundred percent. 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 cross the line from learning and growing into slowing things down? Right at, 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. Yeah. Yeah. Like how do you balance those two things? There's a limit.

To how many questions that are even reasonable, right? Like, and if you think about it like this, if we were to, we were to stack rank value, not if you're 7-year-old son. No sir, absolutely not. He knows no boundary. It's insane If you stack rank the value of questions, and let's say I've got 10 questions. The first three questions I, 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 fir the first big ones outta the way and see if the other ones are necessary. 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 end up being, that's what I'm saying, being like absolute gold somewhere like, not even within the top three, but like somewhere where like becomes a follow on question, uh, in interviews.

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 an example. Years ago I stumbled upon my favorite interview question because I was naturally curious. Uh Right.

I had 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 wanna 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 wanna 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 flood gates to complaints. Oh yeah. Now, now, right. And then, and then listen to them to recite the job description to you, and you're like, okay, yeah. Pass. I never wanna work with people. I don't wanna work with annoying bosses. I'm like, ah, you're not gonna work out here well at all.

Yep. What's interesting is the value of where you can go with questions. Yeah. 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? Yep. 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, yeah.

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 a thousand 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.

Sure. Because I've got the arsenal, the tool belt. To learn everything I need to know on the spot when I get there. Exactly. Yep. I think it's powerful. Um, and it built a huge amount of confidence for me. Alright, so curiosity, superpower questions, super tool. Yep. 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, okay, 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, okay, I didn't know how, I do know how now, but I haven't done it yet. So then we gotta get to that part where, okay, I'll figure it out. I'm gonna go try it. Yep. I'm willing to make the attempt. 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, you're 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 or you know, get a mile, right? Like, no you don't. Right, you will someday if you start with walking 10 feet. And tomorrow you walk 11 feet and the next day you walk 12 feet and you just keep chipping away. Exactly. And what that looks like here, and I didn't know this at the time, I certainly know it now, and watch countless founders through the same journey.

It's all these little wins where you challenged yourself to do something that you didn't think you could do. Lemme give you an example. Yes. So I'll, I'll stick with with me early in the agency days because that was just younger part of me. I remember like one of the. Earliest meetings I was in. This will give you this, give you sense for how old we are. The, the client said to me, there's this new thing, hold, hold, hold your hat.

There's this new thing called e-commerce, and I remember, I, I remember he emphasized the e be because it wasn't commerce. Now, Ryan possibly mean, it was called e-commerce. And I was like, eCommerce, do you mean electronic commerce? He's like, 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 that starts somewhere. So he is basically said, I wanna sell shit on the internet.

But at the time, no one was selling stuff on the internet. Like, no idea. 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, right? Um, had 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 his call. I want to 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'll 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 turn 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. Textbook. Yep. There you go. So I somehow played Joel. Somehow I somehow got ahold 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, sorta. I was like, can you build one? And he said, yeah.

I was like, you're hired. He was like my first employee, but, but we got it done. We shipped the e-commerce. Yeah. And I was like, oh. So part of growth is challenging myself to do things that I couldn't do yesterday. Hmm. I wonder if this will ever come up again. Like 10. 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. Understand.

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. You bet'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 building e-commerce. It might have been a step too far. Right. But you'd taken a bunch of little steps up to that point, right? Like, hello world. I coded some HTML. Yep. 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, okay, 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. 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 hundred 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 180 5, put 2 0 5 on the bench and just press it. And part of your 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, than 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 a thousand times before you, which means the answer already exists. You may just not know it, but that's okay.

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 [email protected]. 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. Well, let's stop for just a second

and I wanna talk about the line between ambition and recklessness, right? Yeah. 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, hadn't done eCommerce 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 okay attempting, what can I feel good about trying? How do we start to draw that line? I think we start at the, the very least is if again, uh, pardon my meathead bench example, but, but if my bench is 180 5, if I don't do something that's incrementally more than that, I'm using the bench example just 'cause it's very numeric. Right. If I don't put more on the bar to try Yeah. I will never get further.

Okay. Now, correct. 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, 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, okay? No, you're not gonna become an entire CFO, but you can learn how an income statement works, right? Yeah. Yeah. You can say, I'm just gonna learn the. Basics of where Yep. Income goes, where expenses goes, and how profit ever happens. Right? That's it. I'm not gonna try to learn more than that. Yep. But that's more than I know right now. That's 10 more pounds on the bar.

That's how you do it. What about the case? The case? Because. I totally get the case for incrementality, right? Yeah. 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 fandom. Yeah. 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 press in my entire life, which is nearly true. I have done it a few times, but not very many. So if, if you say, can you bench 2 0 5. I either have to say yes or no. I don't have anything to base that off of. Sure. I don't know if I can bench 180 5, so I don't know that two.

Oh, five's a stretch. Yeah. How do we approach that? 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 were 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, 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. 3D modeler and the 3D modeler goes into the 3D program and does, you know, some renderings. And I was like, how do you do that Again, this is question guy, right? I was like, what are you using? And he's like, I'll use a program called Sketch Up. I'm like, oh, okay. That's interesting.

I've used a little bit of Sketch up downloaded 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 is just not how it works. Yep. 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. That draw a box, right? And you can ex an extruding in any direction you want.

Again, 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, okay, 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. Yeah. 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 adept. Right. And I've always wanna learn to play one's sitting in the cornerback there. Well, it's been, is that, is that thing moved in 10 years? 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, oh, oh, you're a musician. I'm like, I'm not. I'm just a guy that ha happens to have a, a guitar in the back of his, his office. And when we sat down on this weekend, she talked about it.

She's like, dad, 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 too.

Right? I think, Ryan, this is a long way 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 180 5 when they should be pushing 35 and they're like, oh, I can't bench. No, you can't bench that much 'cause you haven't started with 35. Yeah. Yeah. We see this in so many different way.

Like fundraising's probably a really easy one to pick on here because people call me like, I need $5 million to build everything I ever want to build. Okay, 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 exactly, 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 they're gonna accomplish, but they're biting off way more than they could possibly chew. Yeah. Because of that, they don't really know where to start. They don't have the competence to start. 'cause 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 or a lot it started with, 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 is like. How I was like drawing lines one circuit at a time, right? Like I understood what a 15 amp 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, at a time. He was like. That seems super obvious when you say it, but I would've never thought to do it like that. I was like, that's why it's a engine move. Alright, 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, and sometimes you don't even realize you're making the big one until you know, until it becomes something else. Sometimes the big one just really isn't obvious because it is just a collection of the small ones. Right? 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, okay, 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, that ends up needing to happen is that we gotta get really good at. Being wrong. Right.

Which is to say that like a lot of those little things, like sounds, we're gonna go try. Yeah. Is they're not gonna work and that's okay. 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 wanna talk about. Now. I wanna talk about like how do we get good at being wrong? I found it easy, comes naturally to me. Well, I got the wrong part down Pat. Um, yeah, I'm super good at it. When you were going into your career, how did you see being right. Versus being wrong like that. It's o like what would've told you that it's okay to be wrong. 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 a performance culture, right? I performed well in school, was a, was a, uh, you know, strong student athlete, merit scholar, all that stuff, right? 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, 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 okay 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. When they were still very, very young and I needed to bottle feed them at this point. Hold on, back up. Just so everybody knows, Ryan, you're not being metaphorical right now. You're from Ohio. I'm not being metaphorical.

I was literally, I used to, I found an arbitrage play where I could buy male dairy calves from dairy farmers for $10 a piece, put $50 worth of milk replacer into them, put 'em out the pasture. A bag of grain for 25 bucks and sell these things for seven to $800. Right, right. So at 10 years old, this was a fantastic business in a big level up. A huge level up.

Right. But so I, I decided one morning on a Saturday morning that I didn't wanna wake up at five 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 and winter is cold. Um, and young animals are very vulnerable. I came back to find one of my five dead, his name was Star. I was still naming at that point. That's how, that's how tender and naive I was. Never 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. Right. Um, and so I think it was all those little things, man, you just start to stack up this, this ability of being wrong. I

think we came from an era of bravery. I. And when I mean bravery, I, I mean bravery being like, you have to be brave and bold and Right. And that bravery, uh, was an attribute of being right. And here's A BMW or here's a BMX bike kid. Go prove that you're brave. Right. Exactly. We were given challenges and please don't wear a helmet. Please don't have it. Um, it reminds me of a great quote.

And, 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 wanna recount how many hours I have on steam to civilization, but it's probably longer than the last. I saw a screenshot once. I'm actually wondering how many people you have working on that simultaneous. 'cause it's more hours than you've been alive. Seriously, as if I'd never slept. There's a quote that that pops up.

You know, whenever you hit certain milestones, Uhhuh, 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 per, is being the only person that knows you're afraid. And I love that quote. Bravery is the person that knows you're afraid. And I think that goes to that. That speaks to what we're talking about, right? Yeah. Which is this idea that I'm brave enough to be wrong.

I. And I'm the only person that's willing to admit that I have no idea what's happening. Right. Like I felt the more I could be brave by being wrong, the more unstoppable I became. Right? I, I, yeah. I really, genuinely, genuinely believe that as I got 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 'em all.

And not try to have the right answer and just let the answer find me. By virtue of elimination, I am unstoppable. Now, it doesn't mean I'm, I'm gonna be victorious. It means the opposite, where I'm afraid to make decisions or take leaps. Yeah. I'm afraid to be brave because I'm afraid to be wrong. Yeah. Right. 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 early, 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 wrong.

Huge part of it for sure. Just a couple weeks ago, we had a little situation at school and my, my 7-year-old comes to me and he's, he's visibly upset and as he starts to tell me the story, he's starts to cry. He's telling me about something where a, 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 the important part. 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. He'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 it. I'm willing to jump.

You've gotta be willing. You have to be brave enough to accept what the fall feels like. Not sure that landed all that well with the 7-year-old. Maybe he'll remember it someday, but that's okay. I said it planted seeds, shook his head at the time and he stopped crying shortly thereafter. Yeah, right. So given what we do for a living specifically as founders, I don't know that I'd give the same advice to doctors. Ah, just get some surgeries out there. See how it goes. Wing it.

You're gonna be wrong, but this is a valve replacement. We're gonna cut 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. Right. 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 wanna 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 team that's never done it before, how do you possibly know what these answers are?

Yeah. So in order to be able to have the confidence to to go through that, you have to be able to say, I don't know. 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 fail at a million things we just do.

Yes. Right. But I think our perseverance toward failure is what helps us unlock the things that work. It absolutely is. I mean, this is where the learnings come from. I, 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. Yeah. Where we have to be.

So certain of ourselves, we have to present this future that clearly doesn't exist yet, right? We gotta 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? While sort of openly admitting uncertainty and, and I just saw this done really well a couple weeks ago now. Founder was sharing their 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. I like that movie 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. Right, right. 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 okay.

We've gotta chip away the, the way I see it, Ryan, like. Confidence is built, not born. It is a muscle that you have to develop. So when folks think about like, I wanna be this confident leader, awesome. The way you do that is 1% at a time. It's not like a a 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 that 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 okay. That's okay. You won't be more confident tomorrow. You'll 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.

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 [email protected] to see if it's for you. Could be just the thing you need. I hope to see you inside.