What if I'm the Best, but don't know it? - podcast episode cover

What if I'm the Best, but don't know it?

Jun 23, 202655 minEp. 337
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Episode description

What if building a company is the fastest way to find out what you’re actually capable of? This episode explores how startups don’t just get built by founders—startups build founders by forcing them into new roles like finance, sales, marketing, design, legal, and leadership, often before they feel ready. Will shares how real stakes (like cash flow and payroll) turned “I’m bad at math” into practical financial skill, and why getting to ~80% proficiency across key areas creates leverage, better decision-making, and protection against getting bullshitted. The conversation digs into how exposure and environment unlock hidden potential (from Lars Ulrich’s story to personal career turning points), why most “I can’t” is really “I haven’t,” and how repeated reps, feedback, and humility turn competence into confidence—plus a cautionary backup-dancer story about confidence without practice.

What to listen for:
02:10 Creating Your Own Role
03:59 From Math Failure to Finance
07:04 Asking Dumb Money Questions
09:35 Become What Company Needs
10:47 The 80 Percent Rule
11:42 Agency Skills Stack
15:12 Cross Skill Superpowers
16:44 No One Can Bullshit You
19:05 AI as Private Tutor
20:13 Exposure Creates Greatness
27:03 Defining Moments Reframed
29:18 Dad Versus Computers
32:48 Reinventing Your Identity
39:26 Founder Reinvention Loop
42:27 Craftsmanship And Parenting
45:36 Dance Off Reality Check
52:28 What If And Keep Moving

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

Transcript

Intro / Opening

Welcome back to another episode of the Startup Therapy podcast. This is Ryan Rutan, joined as always by my friend, the founder and CEO of Startups.com, Will Schroeder. Will, the founder journey is like one long accidental apprenticeship in becoming someone you never thought you could be. You start a company thinking you're building a product.

You suddenly, you're learning finance, sales, hiring, design, legal, and apparently whether you might be a secret world-class backup dancer, but we'll get to that later. Will, is, is becoming a founder the ultimate unlock for discovering what we're actually capable of? Yeah. Here's the fascinating about it. Like, my opinion of myself and my future going into life- was so incredibly low. And I, I was like a fairly confident kid. It wasn't that.

Yeah. It's just, like, my life circumstance did not have a trajectory that, that was going up and to the right, right? Like- Pretty sure … it was going to peak at flatline, and then almost certainly- Right … like, bomb from there, right? Yeah, with, with some possible dips. Yeah. With some possible dips.

And when I look back at that, you know, kind of baseline moment, and then all the things that happened in my life since then, it's impossible for me not to look back and say, "How the hell did this happen?" And when I say that- Yeah … I mean, like, how did I become the person I am today- Yeah, yeah if not for being a founder? If not for being a founder, none of what made me, me would have ever been put to the test to make me, me. It's an amazing culture.

Yeah. Founders don't just build companies. Right. Companies build founders, right? That's a great way to put it. If I go back in time, man, I can… Like, my startups forced me into rooms that my old identities, even the identity at the time- Yeah would've avoided forever. Yep. Like, it, it never, never would've crossed those lines. Never would've done some of those things because I wouldn't have had to. It held me to do so.

And here's what's fascinating to me, and I think this is the genesis of what we're gonna talk about today. What if we hadn't been put in this position? And I look at this all the time. This fascinates me. What if the people who've done the greatest things, whether they're, they're musicians or entrepreneurs- Yeah … or whatever, were never put in that position to become who they were meant to be. What if? Yeah.

Creating Your Own Role

I'll give you an example, just kind of moment in time. So I'm, like, 26 years old, give or take, right? And I remember thinking about this. I, I, I remember where I was sitting and how I was thinking about it, and I'm like, "Shit, man." Like, I'm the CEO of a company right now. At the time- Wow … we had like 200 people. And I'm like, "How did this happen?" I mean, it happened so fast.

So a part of it was me actually being like, "Shit, literally how did this happen?" But the other side of it was like, "I'm actually pretty good at this." But there is no way in any world whatsoever that anyone- Right … would've recruited me to this job. Yeah. Right. If it weren't for the fact that- Yep … I created the job, this would have n- I would've never been given this opportunity. Yeah. And by way of that, I'd have never really been able to see what I was capable of.

Yeah, because I think as, as, as humans, we generally confuse I've never done that with I can't do that. Right? And I think- 100% … I think being a founder forces you right out of that. It gives us permission to become weirdly competent at things that we had no business attempting, right? Like just- Right, right … absolutely no business.

You do not have entry to this room, sir. Well, well- And yet I'm here … y- and y- and yet I'm here, and that fascinates me because we get into this, this question that, that I think founders should be asking themselves that we'll explore a lot today. What if I am capable of something so much more extraordinary, by the way- Yeah in any aspect of life, right? Yes. I'm not specifically just talking about being a founder. That is, like- Yep … one role.

But if I could do this, how many other things could I do that for whatever reason I was just never given the opportunity to do? Yep. By the way, including being a founder. Yeah, yeah. I think a lot of people go into this, and they have this imposter syndrome that, "Oh, I could never be a founder." Are you sure? Right. Like, 'cause everyone else that said it had to do it for the first time. There was no internship to being a founder, right? Right.

You're either founder and CEO, or you're not employed there at, at all. The founder role is the internship, right? Correct, right?

From Math Failure to Finance

As I got into that, uh, into building company, and you, you did the same thing, I got into this place where all of a sudden I was like, "Shit, I have to do this other stuff too." Yeah. And, and, and here's the one that I remember most closely. I remember when I was first getting started, I'm, like, 19, 20 years old, like, as I'm building the company, and I have to do finance. To set the picture, this is, this goes back to my early flatline in life.

In freshman year of high school, freshman year, I had to take Miss Chesney's, um, Algebra 1, right? This is like- Yep … basic, basic algebra To this day, 40 years later, I have never passed that class. Okay? So here's what happened. I took it, I failed it. This, and this is my confidence in math. I just wanna, like, set the stage here, right? I took it, I failed it, I went to summer school. Took it aga- I failed in summer school. I failed again in sophomore.

I failed again in summer school the next year. I failed again. I mean, I literally failed it every single time to the point when I got to college. Do you know, like, you know there's a 100 level course? Do you know- Yes … there's an 050 level course? I did not. Before you get to 075, by the way, 050 is, like, next level remedial, right? Oh, wow. And it's for people who didn't make it past the freshman year of- Yeah … of algebra. Now, I just wanna set the tone there, right?

Ryan, you've worked with me for a very long time. Yeah. I've seen you do algebra. Yeah. Exactly. So clearly, I, clearly I understand numbers, right? But something really fascinating happened in the early, early stages of, uh, of my career. All of a sudden, I had to put dollar signs in front of those numbers, and more importantly, those numbers reflected the amount of money in my wallet, right? Yeah. Or whether or not I could eat or make- Yeah … payroll, et cetera.

Yep. And all of a sudden, when the same numbers had new context- Yeah … I was like Rain Man with numbers. Context goes so far. Just briefly, I sucked at math, but I was very- Yeah … good at finance. Yeah. Speaking of dollar signs in front of stuff, just a, a funny little aside here. So during my university career, I took calculus, and I- Mm-hmm … took the business version of calculus. And so I went through that, and it had a lot of dollar signs in it.

When I decided after selling company two that I wanted to go back to medical school and do the thing that I had thought I would do from the time I was quite young, I had a bunch of science requirements that I had to go back and take, and they're like, "Okay, so you're gonna have to take biology and physics," and I was like, "Okay, of course, of course," and then, "And you'll have to take calculus." I was like, "Nope, I already got that." And they're like,

"You had business calculus." I'm like- … "Excuse me, sir-" You had bank calculus … "what's the difference?" And really, I got them basically to admit, they're like, "Well, we're gonna change dollars to grams, and that's basically it." I'm like, "Okay, cool." Right. I look at this and I say- Given that trajectory, and this is multifaceted. Number one, that I hated math. Yeah. Okay? I still do. Number two, that finance to me was this mythical thing that- Yeah … only magicians could perform.

Right? And I didn't understand it. It's the way f- most people feel about their taxes. Yeah. They think about this tax, this- They said the F of X and my eyes crossed. Yeah, exactly, right? And so, like, a lot of people look at taxes, and they think of it as this really scary, like, monolithic thing that they couldn't possibly get past. Uh-huh. And the reality is they're not complicated at all, but there's a whole industry that, you know, that helps you think otherwise.

Asking Dumb Money Questions

Anyway, one day, we, as we're, we're growing the agency, we had merged two agencies, our digital agency and a traditional agency. Well, the traditional agency, which was a little bit bigger, had a full-time CFO. Yeah. And this guy hated my guts, right? Because I would sit there, Ryan, in every meeting and be like, "Yeah, but what about this? Or why does this work this way? Or why does this work this way?" Yeah, yeah. He like- And he thought I was questioning him.

Yeah. Which in retrospect, maybe I was. You're like, "I'm just trying to get to 100. I, I did 050. I'm trying to…" Yeah, e- exactly. But here's what, here's where it got interesting. Because I was a s- total neophyte. Uh-huh. But I was so ambitious about what- Yeah … what I wanted the outcome to be, like how I wanted those numbers to suit me. I asked really dumb questions that weren't dumb questions. Things like- Right, no, fundamental questions.

Yeah … why do we give our clients 30 days to pay us then? He's like, "Well, that's just the, the way the industry works, and then those are called net terms." And I'm like, "Why don't I just not put those on the invoice?" What, yeah, what if we didn't? What if they paid us now? Yeah, exactly, or ahead of time, right? I was like, I was like- You're the finance guy. Yeah. Explain to me the difference between zero and 30 in terms of time value of money.

I was like, well, because the whole thing is we were growing so fast that we weren't making money fast enough to hire all these new people. Yes. Yeah, it's, the agency conundrum always. And we had, and f- folks that, that understand this business well know that, that you've got your receivables in, uh, invoices you sent out, but you also have what we called work in progress, which is- Yeah … this is stuff we're still working on. We haven't even sent a bill for yet. Yeah, yeah.

But I still gotta pay dude by Friday, right, for that time- Yeah … regardless of whether it's work in progress. Uh, where are our paychecks? Oh, they're also work in progress. Work in progress. That doesn't work at all. I come into this thing called finance as a total neophyte, but- Yeah … someone that w- turned out to be pretty good at solving problems, right? Yeah. And I was like, "Well, what about this? What about this?" And really, like, overhauled a lot of the approach, right?

And it served me well. And as you would know, because, you know, for as long as you've known me, I've been a startup CFO. Yes. Like, I'm, I, I- Right … I tell people I'm also secretly the CFO of, of Startups.com. But it's a job I take very seriously. Yeah. And, like, uh- Well, it's a good one to take seriously. Yeah, yeah. But, but I mean, like, I'm passionate about it. Well, it's the thing, it's like in freshman year algebra, you don't really have any skin in the game.

Okay, you can argue that, like, "Well, but then your future is based on your grades." Yeah, no, it's not. It's absolutely not. Uh, and argue all you want. But the minute it, you all of a sudden have the skin in the game, right, where this is literally cash flow that you're depending on, all of a sudden everything becomes a, a very different story, right? The context in that situation is what then drives us to needing to do that, right?

Become What Company Needs

Because, look, as founders, we're forced into becoming whatever the company needs next. That's the point. Right? Which has value. The job description is basically become the person this problem requires. Correct. Right? Right. Think about that for a second, though. Like, I think people go begrudgingly into those paths like, "Oh my God, I gotta learn finance," or, "I've gotta learn marketing"- Yeah or, "I've gotta learn design," or, "I've gotta learn, uh,

programming." And I look at it a different way. I'm like, what if you're really good at it? And everyone says- Yeah … the same thing. "Well, I'm not." How do you know? Have you attempted to become proficient? Or have you- Yeah … tried it and immediately agree that you just don't know how to do it? Which is, by the way- Yeah … applies to every single thing you didn't know how to do. Yes. Right?

Like, I just happen to know how to ice skate, but it wouldn't be like just because I wanted to do it, it would just magically happen. Like, I'd put on a pair of- Correct … skates and start skating. Yeah, yeah. Right? But clearly I, I'm capable of doing it. Yeah. I just haven't done it yet. Something I even- Yes … try to impart on my kids, I'm like, "You can do nearly anything, you just haven't yet." Yeah, 'cause y- we, we all go through that, right?

It's like startup life turns like, "I'm not that kind of person," into, "I guess I am now." Right? Yeah. It, it happens all the time because we're forced into doing it, and I think that's, that's, it is an important part of it.

The 80 Percent Rule

Another founder I know that, that's actually had a really interesting career where he's had proficiency in a whole bunch of categories, like very disparate things, told me something a long time ago. He said, "I only need to get to 80% proficiency to be- Yeah … 100% at good at the things that I need to do with it." Which I thought was a genius reckoning because you look at that and you say, "If I wanna learn photography, I don't- Yeah … have to be the best photographer. I don't have to

have the best details." Yep. "But if I can get to 80%, if I can be a B+ photographer- Yeah … there's no photos I can't take at that point that's gonna affect me whatsoever. Now, will it put me on the cover of whatever magazine? It will not. But I don't need- No … to be on the cover of whatever magazine. Don't need to be on the cover. I just need to take- Yep … dope Instagram photos, right? Yep. Yeah, exactly. That's all I gotta do.

It's like I, I don't have to be Wolfgang Puck for my kids to enjoy the shit out of dinner every night and tell me, "Daddy, you should have a restaurant." That's, that's, that's what I'm saying. I go, "Definitely not." Right. Don't want them.

Agency Skills Stack

As I was growing up in the startup world, particularly with the agency, the agency was a phenomenal gauntlet for me- Mm-hmm … to be able to force my hand at creative, which turned out to be very important to me. Technical, so programming, uh, and pr- and product development. Sales, which is, you know, a critical part of get- Yeah … getting deals in the door. Marketing, which is literally what we did, right? And then stuff people wouldn't expect, like legal. Yeah. Right?

You know, R- Ryan, you worked side by side with me on lots of our acquisitions. I'm not afraid of legal. Lots of red lining. Right? Yeah. Like, in the mix. I'm, uh, side by side w- with our counsel saying, "This is- Yep … exactly what the, things you do." I argue provisions with them like I'm- Yep … I'm by no means an attorney, but I definitely understand legal. But that's the point, right? You don't learn finance because you love spreadsheets. Right?

You learn finance because if you don't, payroll dies, pricing breaks, and investors eat you alive, right? Right. This is why, right? It's not like you're passionate about legal necessarily. I mean, look, it could be, but passion isn't the, the starting point, right? Right. Sometimes it's just necessity, which then becomes this doorway to mastery. Which is powerful. Um, which I think is amazing. Yeah. Let's build on that.

So all of a sudden, I realize that I have to be good and- Yeah … genuinely proficient at a whole bunch of things because I'm building- Yep … a web design agency. And, and within- Yes … the agency, you built the same thing, so I'm, I'm telling you what- Yep you already know, but for folks listening. You have to be meaningfully proficient at at least four things. This is, again, web design back in the day. You have to be able to sell. Like, I don't wanna undersell that one enough.

You have to be very good at sales in any professional services if you're gonna grow that business, right? Yeah. And there's a absolutely an art and an ability to doing that. Back then, you had to be good at, at programming because- Yeah … like, for one, there weren't that many programmers out there, right? You know, what we call it- I had to cultivate several, right?

Yeah. It was like I just found kids who were smart, and it was like, all right, so- Or you had to learn it I'm gonna teach you something called HTML and JavaScript. And they're like, "What's this?" Exactly, right? Like, you had to learn it. The next thing is you had to learn design. You know, back then it was just Photoshop, but, like, you had to understand the principles of design, et cetera, which is a very different skill set, as many people will tell you, than engineering, right?

And programming. Yep. And then the third is you had to learn marketing. So web design was very new, right? Like, so you had to understand all the other aspects of marketing. You understand print design, you had to understand billboards, you know- Yep … outdoor media, et cetera. And so I found that that moment in time to be, like, the perfect cauldron For me to f- force myself into learning everything. So I'm picking up HTML, which sounds stupid now, but that was a big deal back then.

As fast as I'm picking up, it was Photoshop 2.0, I remember it had just come out with Photoshop 2.0. Yeah. As fast as I'm learning the fundamentals of marketing. Yeah. And it turned out I really loved all of them. Yeah. Right? But you never would've understood that, or you would've had no way of knowing, right?

And, and part of it is, like, so for me, part of it was, it was that I, individually I'm not sure I would've loved them in the same way, but I loved the fact that they were the system that the business ran on top of, right? Yeah. That they were the ingredients, right? Like, maybe I don't really love white flour, but, like, I do like to make cakes, right?

Yep. And so, like, at the end, because it ends up being this system, it was super fun to then, like, know that I had the ability to manipulate the levers that controlled the outcomes within the business, right? Yep. And it was super empowering. Here's where it got really interesting, and I wanna present this to folks listening as maybe a little bit of a carrot to why to double down on some of these things.

Cross Skill Superpowers

Yeah, yeah. All of a sudden, the cross-pollination of these skills got me to a different level. Yep. Specifically sales and finance. Uh-huh. Two worlds that are usually so far from each other. Yep. Right? Unless you're in, in Wall Street. But h- here's what it was. Back when we were doing acquisitions, remember I was, I moved to San Francisco and I'm meeting- Yeah … with all these companies, et cetera? I could do this really- Yeah, the, the three years we didn't sleep?

Yeah. I could do this really fun trick where I could be in a pitch meeting where I'm talking to a company who, who I wanna acquire, but as I'm talking and selling, I'm also running every financial pro forma in my head- Yep … as to whatever they just said, I already have in my head the modeling- Yep … of h- what that's gonna look like. Yeah, you build the financial model based on the discussion. Yeah. Correct.

So, so when they're like, "Oh yeah, but, you know, we have a receivables issue," or our LTV is whatever. Yeah. I know exactly what that means. Now, not just for their business- Right … but specifically where that's gonna fit into our business, because I also run our pro forma financials, right? And do all of our modeling. Yep. So as I'm selling, right, you know, using that skill that I had developed, I also can simultaneously do that. Same thing works in a, in an investor pitch.

The investor's like, "Well, what about this as it relates to marketing?" Yeah. I don't have to, like, turn to the marketing team and ask them how marketing works. Yeah. Or if they ask us about technology, I don't have to turn to the technology team. I'm like- Yeah … "Well, this is how we would do it." Right? Now, I'm not saying I have 100% of command of all those things, but I'm never asked to. Yeah, when you get into the 20%, then that's where the, the specialist comes into play.

No One Can Bullshit You

Here's the other side, and I think you'll appreciate this one the most, 'cause no one talks about this. Knowing 80% of every skill means no one can bullshit you anymore. I love it. Right? I absolutely love it. I love when I can just kind of sit back and let somebody think that they're talking over my head, and then just push back on it a little bit and just watch the look on their face when they're like, "Oh, shit, he knows." Yeah. Like, he might not know as much as I do. He's up.

But he definitely knows enough that I can't, just can't talk circles around him. Like, it's like walking onto a car lot as somebody who's, like, a complete gearhead, knows everything- Yep … versus just, like, I don't know, my mom walking onto a car lot, right? Where they're just gonna be like, just run her over the coals. And… You know, it's funny you should say that. So this actually, I can't believe I, I, I always forget about this. So I ran a company called swapalease.com.

I- Yeah … obviously you know that, but I'm saying for, for folks in the audience. And it was a, a, a large lease assumption marketplace, still around today, I think. Early back then, I wrote a book about how car leases work, right? It was called Lease Advisor. Yeah. Right? And so people didn't understand leases. They still don't understand them today. Yeah. Like what a lease factor is and things like that.

And as a piece of marketing material, I wrote a full book- Sure about, like, how to shop for the perfect lease. Like, it was just a- Yeah … compendium to what we were doing. Not a year goes by where I don't find myself on a car lot, right? Like buying a car- Yeah … for someone in my family or whatever, right? Yeah. Where I wind up in the finance department across from the guy- Yep what they call the F&I guy. He's trying to school me about how- Yeah, yeah … monthly payments work. Right?

And to your point, it's the equivalent of someone, uh, speaking Spanish in front of you. Yeah. Assuming you don't know, understand a word they say. That I have no idea, yep. Yep. And then you parrot it back in perfect Spanish. Yeah. And like, "Oh, huh." Like, " Uh-oh- Yeah … what else did we say while he was standing here?" And I, I always politely say, like, I was like, "Before you get too far into it, I ran a company that specifically does

automotive leasing." Yeah. Right? I literally wrote a book on this. Uh-huh. Like, I understand finance pretty well. Spare us both. Yeah. Yeah, exactly. And every time that happens, Ryan, they're just like, throw the pitch out the window. They're like, "Oh, let's move to the end." Yeah. Yeah, let's just, yeah. We can, we can start signing stuff now. Let's fast-forward the part where you try to pull the wool over my eyes.

But that example has served me so well in building startups because in every case I can be like, "Oh, that's gonna take 30 days." No, it's not, right? No. No, it's not. It's not. Yeah. Like, I can tell right away, like, when, when, you know, I'm being bullshitted, whatever. This typically costs… No, it doesn't. Nope. Nope. Yeah. No, it doesn't, right?

AI as Private Tutor

I think having that ability, which by the way, is forged with time, there's no natural ability that I have- It, it, that's super important 'cause I, uh, all the founders who are listening to this right now, this doesn't mean you have to have, you don't have to be this Swiss Army knife compendium of knowledge who knows all the things when you come in. No, no, you don't have to arrive with the complete skill set. Nobody does. Right.

You just need to arrive with a willingness to be embarrassed repeatedly while learning at gunpoint. And now you get embarrassed in private because you can do it with Claude. Oh, man. With an LLM, you can do it with any kind of AI. Yeah. You can basically ask the dumb questions in front of them. Yep. Holy shit, like, w- what that would've done for me back then. But I would say even now, what it does for me today- Sure … right, is extraordinary. Yeah. There's still things we don't know. Not many.

To say the least. To say the least. And so I always get into this interesting, uh, situation, this, this kind of thought exercise where I think to myself, "What if I hadn't been put in that position? What if I hadn't- Sure … had to learn finance? Or what if I hadn't had to learn design?" Like, what would've ever given me the opportunity to put that to the test?

Exposure Creates Greatness

I mean, human potential is wildly dependent on exposure, right? Unbelievable. A small change in environment, timing, parent, mentor, opportunity can determine whether somebody becomes world-class or never discovers they even have the talent, right? Which is insane, but absolutely true. Years and years ago, in like the mid-2000s, for a half second I was on the board of the Rock & Roll Hall of Fame. Yeah. Like a half second. And- Is it because you can shred guitar well?

Yeah. One of my many things I cannot do, but maybe- You sure? I can see one in the background of the video. Are you sure- That is true … you can't shred guitar? Literally, for folks that don't see this on video, there is a guitar behind me. It has been turned on, meaning like, 'cause it's an electric guitar, like twice. I like that you said turned on because you don't actually turn on the guitar. No, I agree. Yeah, exa- exactly. That's my point, right? That's my point. Um- Case in point.

All right. Yeah, exactly. So anyway, I'm on the board. The, the, the fact that I'm on the board isn't really the point. The point is that as part of your being on the board, they give you tickets to the private induction ceremonies- Uh-huh … of the people who get into the Rock & Roll Hall of Fame. Wild, man. I- it is incredible.

Me and, me and Sarah, every time we went to one of these things was like, "What are we doing here?" Like w- like there's 200 people at, at the event- Yeah … and us, right? We're not supposed to be… We're them. We're not them. Anyway, so, so point is Metallica's getting inducted, and Lars Ulrich, uh, the drummer, gets up there, and his family is right in front of him, right? And he's speaking directly to his family.

And by the way, this is so random 'cause I've been telling this story for, like, 20 years. I just found out- Maybe three weeks ago, Ryan, that what I'm about to talk about is on YouTube. Like, his- No way. This was on YouTube. Like, uh- Oh, wow … they were recording it, which makes it- Okay right? I don't remember cameras being there, but, uh, whatever. But, so what I'm about to say, like, isn't me just making it up. Like, I actually re-watched it.

I didn't even know this existed on YouTube, but- I believe you, Will. It's okay. Yeah, yeah. I, I, I wasn't sure. Anyway- I'm gonna snag this … so, uh, Lars Ulrich gets up there, you know, one of the greatest heavy metal drummers of all time, and, uh, he's talking to his parents. And he said, "Mom and Dad, like, the reason that I'm up here is because of you." Right? Yeah. Like, you let a kid… Y- you're always playing music in the house. R- Ryan, that always reminds me of your home.

You were always playing music in the house, and because of that, like, I always felt comfortable to, to be who I was going to be. And I always- Imagine … pause at that moment. I even said this to Sarah when this, when he was saying this. I was like, "What if?" Yeah. "What if that fucking guy had two parents who were hardcore accountants?" He grew up in- Yeah … San Francisco. N- not unlikely, right? Yeah. And, and all they pushed him to do was more math.

Yeah, they were like, "Can I have drumsticks?" "How about two, uh, mechanical pencils?" "Basically. Is that okay?" Right, like and, and for those of you that know what Ulz Ur- Lars Ulrich looks like, Ryan, I think you described it best as what? Come on, man. This is two weeks in a row you're making me throw out something that's- No, no, no, I'm not, I'm not asking for a- for, uh, any words. I'm saying how would you describe him?

You said he looked like he would've been… I was like, he had the haircut of the last Video Town employee. I didn't wanna steal that line, 'cause it was perfect coming from you. The haircut of the last Video Town employee. What I'm saying is, like, he didn't look like David Bowie, right? You know, like this rock star. Yeah. He looked like the most improbable guy- Yeah … that's gonna start one of the most iconic bands, uh, of all time.

Exactly. And yet Because of this series of events, right, he goes on to become who he's become. Now- Right … now that same bizarre series of events has led to everything from Mozart to Tiger Woods, right? Yep. Where you just had in, in, in both those cases a father figure that had some unusual kind of pressure. Recently, 'cause it, you know, it's out in the movies right now, uh, Michael Jackson and his father- Yeah, yeah, yeah … like, go, right?

Like, having- Yep … this unusual thing, and so bizarre, you know, how it unfolded. What if- Yeah … what if those people weren't in that person's life? Right. Is there any chance they would've become who they became at the level they became it? Yeah. Probably not. Yeah. I mean, Joe Jackson gets tipped into the smelting pot instead of, you know, coming home and, right, he's just gone. Like, maybe Michael still becomes who he becomes, but probably not. Maybe, but probably not.

And, and this is why it's fascinating. Because what if the person- Yeah … that, that we were meant to become never had that chrysalis moment- Yeah … until we became a founder? Yeah, 'cause potential doesn't just announce itself, right? It, it has to be activated in some way. Right. And I, like, look how many versions of us never existed because nobody handed us the, the golf club. Nobody handed us the drumstick. Nobody handed us the microphone.

Nobody put us into a situation that forced us to understand that we're capable of something we didn't know. Right. Right? Because being a founder just puts us at the center of 1,000 opportunities to try, learn, fail, and uncover capacity. Uh, which is wonderful, because a lot of people never go through that, right? They just have these random collisions with things maybe throughout their school years or whatever.

So I think, I think it's one of the things that we should absolutely be, be grateful for in the founder space is that we get this, right? Our potential is sort of forced out of us. Yep. I wanna snapshot a couple moments in time to talk about these counter examples. Because in my career, you know, I started a- as a CEO essentially when I was 19. So people are like, "Oh, well you had a lot of time to work on it," which is true. But there's another way to look at that.

I also had a couple other jobs at exactly that same time, right? Yeah. It wasn't like this was the first thing I did. So if you were to timestamp this, so I'm 19 years old in the summer of '94 or whatever it was when I started Blue Diesel, the, my first agency. But not 18 months prior to that, I worked as a sandwich chef for D'Angelo's, which was like the Subway- Oh, man … you know, like Subway sandwiches- Yeah … of the East Coast, right? Yep. So delicious.

But this is the- Hungry … reason I bring this story up. I got fired from that job. Yeah. Not, not fired for, like, I did something wrong, like, you know, I was negligent. Fired, and this is so hilarious, because I couldn't pass the SATs. What are the SATs? Not what you think they are. At D'Angelo's- Sandwich they were the sandwich aptitude test. The sandwich aptitude test.

Ryan, there is a rule in the employ- employer handbook, like the franchise handbook for D'Angelo's, that if an employee cannot pass the SATs, which is basically a test to just say how much meat should be on each type of sandwich. Uh-huh. How many slices of ham, how many slices of cheese. Yeah, yeah. Right? Need to be on each slice. And it's like the dumbest test you could possibly be given. It's a- I not only failed it, Ryan- It's meat math. Yeah. It's meat math. It's meat math, right?

I failed it three times in a row And so my manager, this guy named Raymond, who's actually a really nice guy- Oh, man sits me down at a booth at D'Angelo's. This is me at 18 years old, and he's like, "Listen, man. I didn't even know this was possible, but I have to let you go." I've never seen this before. Right? Yeah, yeah, exactly. I'm like, "What did I do wrong?" He's like, "You didn't pass the SATs." I was like, "Are we talking about the same SIT- SATs test?" Yeah.

I was just about to graduate high school. He's like, "No, the, the sandwich test." Like- Oh, my God … "You failed the sandwich test three times, man. Like everyone passes this test." Yeah.

Defining Moments Reframed

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 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. And God, man, think about how many people that becomes a defining moment for. Yeah. Think about how many people, like, that, that could have defined. Like, because clearly you don't think… Raymond wasn't like, "Look, here, got good news and bad news. The, the bad news is you, you failed the SAT, the sandwich aptitude test. Uh, the good news is you're gonna go on to become a CEO in the next four years." Yeah. Right, right. Right?

That wasn't on Raymond's mind. Again, I love snapshotting these moments because it- it's such a beautiful illustration of these different life paths, right? I remember going back to my car, my $800 Datsun, and being like, "I'm a giant loser." Datsun. Right? Yeah. No, it was. It was rust-colored. It was disgusting, right? Right. And I remember saying, "I'm a giant loser." And not because I felt bad about myself, because I was like, "Will, dude, like, you're about to enter the workforce,

like, for real, man." Yeah. "You can't hold this job? Like, what the fuck?" Right? Like… And, and I remember being really sad about it, right? Not like my life is over, more like, "Uh, okay, this isn't good." Now, a year later in an alternate universe, Will would go on to start a company and become a millionaire, right? Yeah. Like, within a few years. Yeah. And, but he just lost his job making $5 an hour and thought it was, like, the end of times.

I mean, on one hand, thank God, because what if you- Yeah … just become a really good sandwich artist? Oh my God. Right? Like, what if this conversation was, "Will, I see so much potential in you." Yeah. " How would you feel about being night manager?" Right? And I was like, "Career." Someday you might move to day manager. You, could you imagine owning your own franchise someday, son? Yeah. Dare to dream. Yeah. Right? Well, so that's the interesting thing.

So we talked about, like, the opportunities that come along that kind of put you onto the path. Yeah. But then there are also things that can come along that force you off a particular path, right? Yeah. And I think that those are interesting, too.

Dad Versus Computers

You've got another pretty hysterical anecdote that I would love for you to share around how much time you were spending on your computer. Oh. Okay, so This is one of those moments where, like, this could have easily derailed things in a different way. Let's take Tiger Woods' dad, Earl, forcing him into playing golf in two years old, okay? Yes. Fast-forward, or rewind, I guess, in this case, I'm now 11 years old, okay? Uh-huh. I will never forget this moment.

I'm sitting there just engrossed in a Commodore 64 computer. Yeah. Right? I am, Ryan, I'm blown away by this technology. What other option did you have? If you were 11 and you had a Commodore 64, you were engrossed, right? That's what it is. I, I, I was just blown away at, at- Yep … the power of this and the potential and everything else like that, right? And I'm trying to explain it to my old man.

My dad, who's a carpenter, was like, "Why are you on this thing?" I mean, he begr- begrudgingly bought it for me. To give you a sense for how much my dad knew, and this, not meaning to, to knock him, but knew about computers, or really anybody did back then. My dad, in maybe the most, one of the most defining moments as a father, bought me a Commodore 64 computer, uh, for Christmas that year, but did not understand that you also had to buy software. Software, yeah.

He just knew that, like, it, Commodore said, son said Commodore box, right? Yeah. And he was able to get the, the monitor. The computer, which back then was the keyboard and the computer was in it, in a disk drive, which was external back then. But he didn't understand that you had, need software. So- He basically bought you a really weird lamp Dude, he bought me a Nintendo with no cartridges. Yes. That's exactly what happened. And so on Christmas morning, I'm like, "Oh my God, I can't

believe it." And then I'm like- Yeah … "Where's the software?" He's like, "The what where?" The what where? And then I'm like, "Huh," blinking cursor, and that's how I- Yeah … learned Basic. A- anyway- Yeah. But fast-forward like a year later, and I'll never forget this moment. I'm sitting there on my computer just playing video games or something, and my dad turns to me. My dad was a huge wrestling fan, right? And he was like, "Son, get off the damn computer and

come watch wrestling." I'll never forget that Saturday morning when he said that. Yeah. And he meant well by it, and what he meant by it- Of course was, "Hey, man," like, "come do stuff that doesn't involve you sitting by yourself in front of this fucking monitor and come to this… Come do something that involves…" Yeah, s- 50-year-old man. But he looked at this computer as this bad device, right? Yep. Like, he bought it begrudgingly 'cause his son was so annoying to get it.

Yeah. And he regretted it every day since then. And so imagine if I had taken his advice for face value and been like, "I guess this whole computer thing, you know, technology thing is gonna go nowhere, but WrestleMania is pretty dope, so I need to double down on that," which it was. M- my point is what if that guiding hand had, you know, gone- Yeah the other direction? He was the anti-Earl of Tiger Woods era, right? Yep. And I had gone a different direction.

I mean, on one hand, maybe you would've become Vince McMahon. How do we know, right? Y- you never know, right? You would've combined wrestling and finance instead. I will say this. There was an alternate version of this, uh, that also happened where th- like that summer, I would go on the jobs with my dad, and we'd build stuff, right?

And I would just be carrying heavy shit like in the middle of summer and… But I remember saying to my dad, I was like, "Dad, how awesome is this that at the end of the day, we get to create something that's never been created before?" I'm talking like structures and things like that. Yeah. And my dad looks at me, I'll never forget this. And he looks at me and he's like, "No, it's not awesome." He's like- No … "I'm 40 years old, man." Yeah. "My back is shot. My knees are shot. Do anything but

this." And so what did I do when I made some money? I became a carpenter. I did the exact- Yeah, yeah … You're like, "I built a wood shop immediately." Yeah, exactly.

Reinventing Your Identity

Yeah. Which brings me to s- sort of my next point in all of this, right? Once you realize that you can be something other than what life told you- Yeah … or what your circumstances afforded you- You start to ask yourself, "Well, what else can I do?" Yeah. Right? Which by the way, is pretty fucking cool. To be empowered enough one time to be able to say, "Well, if I can do this, why can't I do this other stuff?" Yeah.

I stopped thinking about capabilities as the driving force, meaning that, like, the things that I knew I was capable of, right? Yeah. Because I think that's a, a big part of, like, what we're… W- we go through school, we come up, like, as, as, you know, in our, our youth, we're, we're being given a set of tools, right? Mm-hmm. Almost like a, a set of keys to, to some doors that they unlock, and now that's the keys we have.

And I think that what, what we were able to realize through entrepreneurship early on was that, like, I can unlock any door I want to, right? I can forge a key for anything I want to. And then there was this crazy compounding value in, in doing that. Once you figure out you can become one thing you never imagined, you start to question every limitation around you, right?

That first transformation might be the hardest, but after that, that reinvention just compounds, and competence compounds into courage. And once you break one identity ceiling, the others start to look really fucking suspicious, right? It's like, who's saying I can't do this? Like, and what- Right … what the hell do they know? They would've told me I couldn't do that, that, or that either, and I've already done all that shit, so- Right … why don't we go?

So you get into this thing where you look at everything with a second lens. Yeah. And you say, "Well, why can't I do that?" I'll give you some examples that you are familiar with, you know, maybe new to the audience. Years ago, um, we were having our, our house remodeled. Uh, this is when- Mm … Summer's room was getting remodeled for when Summer was born. Yep. So this would've been almost exactly 15 years ago.

We have a guy in the house, and he's basically rebuilding the closet for what's gonna be Summer's closet, and it's a giant closet. Uh, it's just a weird, like, room. But I, I'm watching this guy do it. This guy's, like, in his 60s, and he's sitting there w- with a table saw, and he's building a really beautiful, like, detailed walk-in closet.

Wow. And so I ask him, just 'cause I'm infinitely curious, I said, "Hey, man, how is it that you're able to get, like, all these corners and miters and everything, like, really tight like that?" And his answer blew my mind. He's like, "Well, I go, I measure it, I over-measure it, I cut it, and then I, I go back and I see if it fits. And if it doesn't, I go back and I cut it again." And I was like, "Wait, h- hold the fuck on for a second.

Are you messing with me right now?" Where's the, where's the magic calculation? And I was like, "That's how you make it look like that?" Yeah. He's like, "Yeah." Now, I would learn many years later that that is actually how you do it, right? Yes. Um, it's called sneaking up on the cut. And because when you measure things in carpentry, when you measure things and you try to cut it right the first time- Yep for a litany of reasons, it kinda just never works.

This is, yeah, we talked about last week on the podcast, right? Which is that, like, you can plan all you want until- Yep … you actually put it into practice and play, you're not gonna see whether it actually fits. So the, what a, what a beautiful parallel. Pause on that for a second. But without that dinky piece of knowledge- Mm-hmm … which by itself seems trite and almost, like, silly- Yeah … you actually can't build great things.

Like, in the, in the case of carpentry, in this c- case specifically, trim carpentry. You will consistently plan really well and build things that have ugly gaps and, and shitty seams. Right. You were at my house not too long ago, and we were building some cabinet doors. And wasn't it exactly that? It was like, you can measure it and you can try to get that thing to work. It's not gonna happen, right? Right. Or you can cut it once, it's gonna be off. Uh-huh. Cut it again, it's gonna be off.

L- and basic- Yep like, again, sneak up on the cut. The reason I say this, you know, share this story, is that is actually how I became a carpenter, right? Yeah. Was that guy told me something so simple That I was like, "Hold on a sec. If all that guy does to be a- Yes … seasoned trim carpenter and produce this- Yep … is he just doesn't try to cut it right the first time, then why can't I do that?" Yeah. And it turns out that was true, and I've become a very avid carpenter since.

Yes. And I built some stuff. Yes, you have. So many things seem complicated until you get closer to them, and it turns out that they are just built on some very simple fundamentals. Of course, they take, mastery of anything takes, takes time. But I think when we're looking at anything from the outside, anything that we're not already competent in, it looks way more complex than it actually is. Right.

There are very few things that I've gotten into and was like, "Oh, shit, this is way more complicated than I thought it would be." It's almost always the opposite. There are things that have, that have happened. Yeah, look, I- For, for example Right, right … it goes way more complicated than I thought. There's all kinds of stuff where I actually do have a cognitive wall. Here's what I would say. When I hit that wall where I'm like, this is either beyond my interest level, right?

Yes. Where I'm not willing to unpack it anymore- Yeah, yeah … uh, because I just kinda don't care, it's rarely beyond what I would call, like, a physical boundary- Yeah … that I simply cannot surpass, right? Right. Now, there are certain things, sports would be an example, right? Like- Yeah. Right, you, you were a great soccer player, but if the MLS called, right?

Yeah. Or World Cup, which I think is coming up next week, calls and says, "Hey, we need you to play tomorrow," there's a tiny chance you may not make it. Yeah. Well, look, I would… If they called, I'd go. It'd work out poorly for everyone. That part isn't the problem. Yeah. The problem, the, the problem happens when I actually hit the pitch, yeah. Right, right, right. You can't sneak up on that cut. Yeah, you cannot.

And so there are certain things that require a level of raw capability or mastery that we have neither the raw capability for- Yep … or the time and willingness- Yep … to master. To prepare, yeah. To prep. Prepare. Did I say prepare? I just made up a word. Right, right. However- That universe of things that's truly beyond what we can probably do is insanely small. Yes. But because from the outside we look at it and say, "Well, I don't know that…" Here, here's a great example.

When people come to my house, you know, again, you've been through this journey with me, so I'm explaining it to everybody else, and they see that, like, I've built every cabinet, every closet- Yeah, yeah everything, or that I've architected the entire house, or that I've- Yeah … pulled, like, all the wire and designed all the systems, right? Yes. Yeah, yeah. They look at that and they say, "There's no way I could have done that." Uh-huh. And I give them the same answer.

Yeah. "There's no way that you can't do it," right? Like Yeah, yeah. Right. There's like… It's, it's impossible to not be able to do it if you're willing to do it, right? Yeah. Because it's not like I have some special honed technique of wielding a drill that you cannot That you can't do. Yeah. Like, oh my God, dude. Like, yes, it, it requires time and, and expertise, but all things that you can absolutely do if you want to. If you want to.

Founder Reinvention Loop

Yeah. Now, what's fascinating about how this maps back to entrepreneurship, you know, and, and people building stuff is we genuinely believe that there are all these skills and traits and things that we can't do And what we realize is most of it's just because you haven't done, and the rest of it is because you're not willing to build the competency. Yep. My Getting Customers workshop last week, I was walking people through something very similar.

So I'll twist it a little bit 'cause we were talking really specific to kinda like marketing knowledge. Yeah. Yeah, yeah. Um, but just think of it as like the founder reinvention loop, right? Yeah. It starts with forced exposure, right? The company creates a need. All of a sudden it's telling you, "There's a thing that has to be done that you haven't done." Then you move into awkward first reps. Yep. You're bad and you're uncomfortable. Yep. And it's okay. Yep. You get some fast feedback.

The market tells you, or the business responds in a way that tells you what actually matters. You start to develop useful confidence, right? Yep. You become dangerous enough, or you get to that 80% point, and then all of a sudden you have that identity shift where you stop saying, "I'm not that person," right? Yeah. And that's it. And this happens over and over and over and over again in a startup company.

Yeah, I agree, and I, I think a lot of people also don't realize that becoming that person isn't something that you, that just happens immediately, right? Nope. Like, all of the people that are the greatest at what they do are the greatest at what they do because of the amount of time they've invested. You know- Yes the 10,000 hours of mastery thing. Yep. Yep. But I'll give that a bit of a twist. I'll give that a bit of a twist or a filter.

Most of us, for what we need to accomplish, just don't need that level of competency. Houses don't get built by 30 master carpenters. They do not, right? I mean, it's- No … unbelievable the lack of capability. And this goes back to what we were saying a moment ago. They get built in spite of the capability. They get built despite- Yep … the capabilities of the people building them, and people downplay that. Like, "Oh, you know, you're, you're downplaying this

person's competence." Nope. No. No, I am not. I saw some of the framing. Yeah. No, no you're not. You, you watched it firsthand. And, and what fascinates me, though, is that each of those people, it's all they do. And I'll give you an example- Yeah … 'cause it j- just happened today. So, you know, as you know, I'm building a house and, and, uh, we're in the, the final stages of this, and, and I'm talking today, I'm on, on site talking to the carpet installers, right?

And they said, "Hey, there, there's word on the street on this project that, like, you're, like, really involved in this project." Yeah. And I was like, "Well, what have you heard?" They're like, "People are saying that you, like, were the architect and the general contractor and, like, the carpenter and, like, the electrician," like- Mm-hmm. I was like, "Yes." The- Yeah. He's like, "Yeah, to which one?" All of them. I did literally all of these things, right?

And, and he said to me, paid me the highest compliment that a man can pay a man, particularly in this thing. He's like, "They don't make men like you anymore," right? And I was like, "Go on, say that into the microphone, please." And, and, and what, what he was saying was- Wait, hang on. Do you mind running it back? Let me hit record here real quick. Yeah, yeah.

And not to take more of it than he said, he basically was just saying, "When I'm working on stuff, when I'm on job site, whatever, I don't see guys that are just willing to do- Every trade. Yeah. I see a trade. I'm framer. Yeah. All I do is framer, right? Yeah.

Craftsmanship And Parenting

And that's it. They, well, it goes back to that skin in the game thing, right? Like, you're doing this because you are literally tied to the outcome, right? Yeah. You're gonna be living in this thing. I really care about the outcome. But I also really care, and again, I think this is a universal term that, that you can appreciate too, I care about craftsmanship. Yes. I care about one's belief that what they build is an extension of who they are.

And that reflects in, in, in every single thing that you do. Correct. Right? Like, it's really im- important to me that my stamp of me, my DNA, right, is in my work, right? Like, very much in- ingrained in it. One of the places that I see you do it in a way that I've, I've always admired, and we've talked about this, is, is your work as a father, right? Like- Yeah … your craftsmanship if you, if you can apply it that way- Yeah … is extraordinary.

And for those of you that are listening that, that don't know Ryan, he is like- I'm definitely sneaking up on the cut. Yeah. Definitely sneaking up on the cut. Uh, Ryan is the Tom Brady of dads. Like, he is like, like, like, the greatest- Oh, man. Oh, man … dad a- as, as a parent. I mean, uh, he, uh, well deserved. And- Am I, am I blushing? Yeah. Good. Yeah. Who knows? I'm white as a ghost. But I, I guess what I'm saying is, like, but you care about the craft.

And, and- Yeah … obviously everybody cares about their kids, but you care about the craft of being a parent. Like you're very, very detailed about it. And there's a pride that comes with that, right? Like when you and I talk- Yeah … on the weekends and you tell me what you're doing with the kids and that- It, there is, there's a pride that comes with it. But more than that, there's an ROI that comes with it.

I just talked to a mutual friend of ours, founder that we both know and love, um, earlier today, and w- was going through a little bit of a, of a crisis herself and, and we were talking about this. And I said, "Look, it's…" And I, I referenced the kids as an example. And I said, "Look, I, I know a lot of people who aren't enjoying parenthood in the way that I enjoy it because they're not…" It, and it was basically what you're saying now. They're not treating it as a craft. Right.

They're not trying to perfect the angles and get the cuts right and do all the little things. And because of that, they're not enjoying it in the same way. Yeah. I think that what I figured out was that the more I invest in this, the more you invest in anything, the more you're gonna get back out of it.

Right. And so, like, I was lucky enough to have stumbled across some of those moments that motivated me into saying like, "Okay, so if it's not going the way I want it to, I can change that," right? "I can make this into something that's enjoyable for me and the kids and my wife and all of us." Which is what this is all about.

It's, it's about saying like- Mm … look, like, um, the reason that we can build competency and the reason as founders, like, we find ourselves, again, in, you know, this, this cauldron of, of competency, like, you know, being able to do these things- Yeah is because, as you said a moment ago, it gives us a reason to do it, right? Gives us a reason- Right … to explore these competencies that we didn't have before. It's rare that, like, I wouldn't have for no reason picked up- Finance, right?

For just no reason. Right. Right? No, no. Like, it's the, the ambition behind it. Yeah. By the way, it, it's the reason I don't know another language. Oh. Because I've never had a reason- Oh … to want to learn another language. It, it took pure brute force for me, right? But you're also in another country, right? I mean, like, I, I- Just exposure, right? Yeah. Right Like, just pure necessity. Like, I can't go and do things I need to do if- Yep I don't learn this language.

Yep. And so, you know, I, I look at it as, I think, like again, the cauldron, I, I keep using that word because it's like you're forced- Mm-hmm … inside of it. And, and I think a lot of people- Oh, yeah … look at it as a bad thing. I look at it as g- as a good thing. Yeah.

Dance Off Reality Check

Now, I will also say this: it doesn't always work. It it doesn't always go to plan. And I'll, I'll share a story, Ryan, that I know you're familiar with, of where I put this maybe I can do everything to an epic test. And I, I won't spoil the ending, but clearly it d- it didn't go well. So rewind back. This is, you know, uh, quite a while back, maybe 20 years ago.

And, uh, I'm a casting director as part of a, a company that I'd started in LA, and I'd just moved to Hollywood, and, and my co-founder was a talent agent, and he knew everybody, and we used to go to these extraordinary dinners and meet all these amazing people. He's the one that got me on the, the board of the, The Rock Hall, actually.

And, uh, anyway, we're at a dinner in Hollywood, and, uh, there's like a big table of us, maybe like 10 of us, and, uh, we're sitting around this like, uh, big table, and there's this guy sitting next to me, right? We're both in our, like, late 20s, early 30s, and we start talking. He's… I ask him what he does, right? 'Cause people in LA had like, say what you will, there's so many people with really interesting jobs. Like, it's very rare. No, I totally get that.

I totally get… It was one of the things that people used to ask me, like what we loved about Antigua, Guatemala, and I was like, "It's the per capita interesting person quotient." Yeah. Like, it was out of whack there. People were… You would just run into really, really interesting people. Yes, I, I, I totally understand. Uh, anyway, he's like, "I'm a professional backup dancer," and this is, again, figure like mid-2000s.

And he's like, "Uh, I've been dancing for, like, Britney and Justin and like…" Which were big deals back then. Yeah, it was sort of the, the peak of the game at that point. Yeah, right. And so he turns to me like, "So, so what do you do?" Right? Now, mind you, a couple drinks in, a little bit bored. I turn to him and I was like, "Well, you know, it's funny you should say, man. I actually am a professional backup dancer, too." Right?

Now, the way to sell it, the way to sell it, okay, isn't just how confident you are. It's by complaining about it. This is actually something I learned growing up- Oh, yeah, yeah, yeah … with my dad on the job sites. Yeah. All those guys do is complain. Complain about the job And it's kind of how they share- Yeah like, their confidence, I guess. And so the way to sell it was I was like, "You know, man, I got into this because all I cared about was performing

and dancing." I was like, "But the game is bullshit now. People are doing it for all the wrong reasons now. Like, you know, n- nobody's serious about, about it, whatever." And as soon as you start complaining about it- Oh, yeah … nobody who doesn't do it for a living would start complaining- Right … about it, right? Yes. And so he jumps in. He's like, "Oh my God, let me… Don't even get me started," right? And so I'm kidding of course, right?

Yeah. But it was just going so well that I just kept going with it. And so as the night goes on, this new nightclub that was opening up, and for those of you that lived in LA or you know the lore, you can kind of timestamp this. This is, it's the weekend or whatever that area opened up. And so we go there, right? Massive line and, you know, Alex Hol- business partners, uh, old thing was be able to get into, like, any club and stuff like that. Uh-huh. So he gets us all in, right?

And so we're, we're up, like, the little VIP and whatever looking over the dance floor, and this guy, he's like, "See those guys over there?" I was like, "Yeah." He's like, "I know those guys." He's like, "They suck." I was like, "Yeah, they do suck," right? And we're knocking down, like, tequila shots or whatever, and so we kind of make our way- Dance fight down there. We're standing there, and I see him, like, talking to them, like, just, like, big talking. Like, he's friendly, but whatever.

And next thing I know, this is where, like, the whole thing turns into, like, Polaroid moments. Next thing I know, he's challenged them to a straight up dance-off. Dance-off. I didn't even know this was a thing, right? Dance battle. A- and I'm sure they don't call it a dance-off. I'm sure there's a much cooler term, but in my mind, that's all I knew. Anyway, so here's what I, I see, like, unfolding in front of me. I see the dance floor open up, right? Like, almost, like, on cue.

It's me and this guy and these other two dancers. And so the first dancer goes in. He's amazing. Everybody's going nuts. My guy goes in, right? He's amazing. Everybody's goes, goes nuts. Next guy goes in. He's amazing. Everybody goes nuts, right? And I'm shouting, and I'm, like, super excited about this whole thing. How have you not left the room at this point? Oh my God, dude. It didn't even occur to me that I was a main event on this dance-off. Yeah. Okay? Oh, yeah. This is the best part.

Yeah. So- You saved the best for last … he turns to me in full confidence because of all the shit I've been talking for the last- Yeah, yeah, yeah, yeah … couple of hours, right? He's like, " You are…" This- And he's like, he's like, "Dude, get in there," right? He's picturing you coming off the top rope. Yeah. Tagging you in. It's- Man, confidence is powerful, but delusion plus tequila- Delusion … plus a dance circle is a very different operating system.

So there was, there was a couple things going on. First thing was there was so much energy at that moment, right? Like, I was just on fire. Second- You had begun to believe it maybe a lot of tequila. Yeah. And third, here's what I said: What if? What- Yeah … I, so I mean, what if, right? What if? Like, I- I will- … I like to dance … I will, I will know soon … maybe I'm really good at it. I will know very soon. Right? And maybe I'm as good as those guys. Maybe I'm better. Yeah. Right?

But I never… Like, no one ever said to me like, "Go for it," right? Yeah. So I did, right? I get out there- Please tell me that in addition to Lars' speech that this is on YouTube. This only exists in the deepest bowels of my mind, and this is exactly how I remember it I don't remember what I did, although now, you know, years later, do you remember that Australian lady who did the break dance thing, uh, in the Olympics? Oh, yeah. Yeah, right?

Like- Oh, yeah … I could only imagine- Oh, yeah … like if you wanna picture a dance, just picture whatever she did. Yeah, it was something like that. My, my- I can see it … cheesy club guy version of that. I can see it. And all I do know is that in a very short period of time, it was very clear to every single person on the dance floor, including the professional dancers, that I was in fact not a professional dancer. Not a backup dancer, yeah.

Yeah. And all I remember is this look of horror on everybody's face, like, "What the hell?" Yeah. And I just remember these two giant hands on my back, like grabbing my shoulders, and being like, "You need to leave now." You gotta go. I remember I was like, uh… And next thing I know I'm, like, in an alleyway or something in the, inside, and Alex is like, "Dude, what were you thinking?" Yeah. And I was like, "Was I any good?" He was like- Was that any good?

… "No." He's like, "You did not" Take two good pop, huh? "You were not." And so this is a, a long story to say that, yes, it is possible, you know, that, that maybe you could be good at everything, but sometimes it is certifiably possible Yeah … that you absolutely suck at it. Look, the lesson here isn't we can master anything instantly. The lesson is we can become more than we assumed with time, reps, maybe a little humility, and a little less tequila.

Um, because while founder confidence is rocket fuel, founder confidence without some reps is a dance floor crime scene. Yeah, yeah. And again, and honestly, like other than a silly story, right? No cost to it, right? Yeah. No cost. And, and I think for a lot of this, you know, we have this idea that, that if we don't, if we don't fulfill that promise, that dream, that outcome- Yeah … that, like, you know, something horrible will happen. No, not really. Not really. Right?

Like, if, if you're not a great designer, if you're not a great accountant, if you're not a whatever, it's okay. Yeah. Like, you, like especially with being a founder, like s- you'll find someone else to do it.

What If And Keep Moving

But what if? And that's why we… I, it's, it, I talk about this a lot in terms of, like, when founders are really struggling to find their ICP, their ideal client profile. They're like, "Well, I don't know if it's this one, or if it's this one, or it's this one." And it's like, what if? Like, it could be any of those, and it kind of doesn't matter. If you pick one, you can either rule it in or rule it out. You're gonna find out- Yeah … you can dance that backup dance or that you can't.

And then we move on to the next dance floor, and you just, you just keep moving. And that's fine. Um- So- I, I- … while, while we respect your confidence, Will, we do question the choreography. Yeah. And w- and, and, and this story's ridiculous in its own right, but the premise of that though, is what if, right?

If we don't try what if, if we don't dig in and say what if- Yeah or at least have the confidence to say, "Yeah, okay, maybe this won't be for me", but it won't be for lack of trying, right? Right. It won't be for me, you know, lack of opening up the doors. I wanna know. I'm not gonna let- Other people's determination of what I c- I, I can or can't be. Like- Exactly … I'm not the guy that passed the SATs at D'Angelo's in the sandwich world, right? Right. I'm not going to be that guy.

And, you know, and for- Yeah … someone else, that could be a huge issue. And I'm like, "Fuck it. You know what?" Yeah. "I'm gonna go do, do something else." And maybe I'll fail- No dress rehearsals in life. Yep. Yeah, exactly. You know, like, and maybe I'll fail at that, too. But the difference is I'm gonna use this opportunity, in this case of being a founder, to be the one time, the one time where no one can tell me what I can't do except me, right?

No one can say, "You can't be the CEO, you can't be the designer, you can't be whatever," except me. And I think when we have this one unique opportunity in life to be all of the things that maybe we should be, we should take it. We should go after every opportunity possible as if we're, maybe we're the best, 'cause who knows? Maybe we actually are. 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 bootstrap 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.

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