Why are we Really Building a Startup

Welcome back to the 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, I don't think founders ever lie to anybody as much as they lie to themselves. We tell the world- That's a great opener. ... we're building to change everything, but I feel like most of us are really building to fix something that's been following us around since we were a kid.

Will, w- why is it so damn hard for founders to admit their real why, and what happens when they finally do? I think we all know it, and I think a lot of people are kind of f- frankly afraid to, to admit it, and l- actually, to admit it to themselves. Yeah. Okay? So- Themselves, exactly that. You're right. Here's what we tend to say, and we s- I mean, we've had these conversations a million times. Here's what we tend to say.

We talk to a founder and we say, "Hey, what are you trying to build?" They're like, "Well, I'm trying to build this thing that'll change the world." Mm-hmm. And I'm like, "Cool." Yeah. "That's wonderful, but why?" Right? "Oh, because I think, you know, th- this problem should exi- " No, no, no, no, that's, that's, that's why the problem exists. Uh-huh. Why do you wanna build it?

You. But, like- Yep ... what is it about this that if the company was one person big, 100 people big, or 1,000 people big would change you? Like- Yes ... like, w- where are you in this equation? Right. Right? And nine times out of 10, they're like, "I don't... Huh?" Right? Yeah. Like, "W- what do you mean?" And I say, "Look, man. All of us are building something in life, whether it's our business, our family, you know, everything, in order to fulfill something inside of us." Yeah.

"But most of us have no idea what that thing actually is, whether it's a demon, a void, or, you know, some combination thereof. So we kind of blindly build-" Yeah toward a thing in order to like, like, fill that void, et cetera, or, or satisfy that need without ever defining what it is." Yeah. And that's a huge problem. It's a huge problem. Because you're usually wildly miscalibrated. Yeah, man.

The public why is marketing, right? The private why- Yeah. Yeah ... is, is motive, right? Yeah. And if you don't know the motive, it's kinda tough to steer the machine, right? The, uh- Yep ... change the world, to me, that's the wrapper, right? It's not the product. Yep. Yep. The product is some version of, like, safety, validation, freedom, revenge- Yep ... belonging. Yep, rev- yeah. Right? Some, some- Revenge is a good one healing of deep inner wound. Insert inner wound here.

Yep. You got your internal why. I, I saw a great quote, still call it Twitter, from, uh, a while back from somebody, and they said something to the effect of, "A founder who wants to change the world is exciting, but a founder who wants revenge is unstoppable." Yes. Right? So accurate. So I'm like, " Hell yeah. Hell yeah." Absolutely. Right? And what we're talking about is the, the pure- unfiltered emotion that makes you do what you do. Yes. Right?

And again, without getting, like, too Freudian about it, that's kind of what the... I gu- hell, dude, our podcast is Startup Therapy. Yeah, yeah. I guess we will get Freudian about it, right? Yes. Let's, I was gonna say- Um- Let's go, let's get Freudian about it. Yes. Let's get on the couch, right?

We all have specific reasons why we act the way we act. Nothing comes from nowhere. I always tell my wife this, 'cause when she talks about, like, how our kids are behaving, I said, "Listen, our son or our daughter does not act the way they act out of nowhere." Right. "It comes from somewhere. There's a root cause to that behavior"- Yes ... "and we have to figure it out." It's a combination- And by the way, it's, it's usually us. Yeah. We are the root cause. We're, we're the parents.

I'm sure of it. I'm sure of it. Like, where, where else does it come from? Yeah, yeah. And, and that's fine, but, like, but we have to know what it is. But here's what happens when you don't. This is what kind of gets re- really interesting to me. When you don't know what it is, you start making all of these decisions, again, miscalibrated, right?

Again, you're like, "Hey, I wanna build a huge company." A- actually, no, I'll, I'll, I'll be personal about it. Like, why do I wanna build a company? Why do I wanna be in en- entrepreneurship? Because I'm terrified of not being safe, right? Yeah. Which is ironic- Yeah ... 'cause I picked, like, the most unsafe career path you could. Yeah, yeah, yeah. But the reason for it, again, all this stuff comes from somewhere, is 'cause as a kid I didn't have any safety.

And by way of that, I didn't have any control. Right. So I looked at entrepreneurship as something I could control. When I say control, doesn't mean it's always gonna go well, but it was up to me. Yeah. Right? And that's- Yeah ... all I cared about. Doesn't go well, it's at your hand, right? It wasn't somebody else making a decision of where you're gonna live, what you're gonna do, are you gonna eat dinner or not, yeah. Exactly, right?

And so I looked at it as if I can control my own destiny, um, I don't care if it's good or bad. I mean, ideally it's good, but, like, I don't care if it's good or bad, I care that it's mine, that it's in- Yeah ... within my control, because I grew up without control. Yeah. A- and that was so deep in me. And even 50 plus years later, I don't feel any differently. Like, that same need has not changed.

But if I map back every single one of my actions in life, like all the things I did with building companies, you know, blah, blah, blah. Yeah. It always maps back to that. Sure. Everything comes from somewhere. Yeah. We're, we're not just building a startup, right? We're, we're building a remedy, an antidote to- Perfect ... whatever happened in the past, and we need to- That's a good way to put it. Yeah ... a- and look, and naming it's super important, right?

Yeah. Naming it's super important because if you don't name the real why, it's still gonna drive. Yep. It's just gonna drive from the trunk, whereas- Yep ... a lot less visibility and perspective. And look, investors aren't going to fund your inner story, right? That's not what they're there for. Yeah. Right. Uh, but your inner story- It's yourself. ... does drive the decisions that determine whether the company survives, right? As you said before, a founder out for revenge, unstoppable, right?

Right. Because that's that inner story that's gonna drive them through all of the difficulty of building that company. Right. Right. And I, I think for a lot of us, you know, we look at it and we're like, "Oh," like, "I'm not insecure," or, you know, "Oh, I'm not trying to make up for, like, you know, being a dork in high school. I really care about this thing." I'm sure you do, but- It's funny that you brought up being a dork in high school, 'cause- Yeah. ... I wasn't.

There's the Freudian slip. That's the tell right there. That's exactly what it is. Yeah, yeah, yeah. That thing that they tell you, it's not for this reason or for that reason, it's exactly for those reasons. Right, right, right, right. So all that said, I look at this, you know, when I, when I think about how people are making these decisions, but more so saying, "Here's what I'm trying to accomplish." Yeah. I think they're, without being intentional, they're disingenuous about it.

I think that they look at this and they say, like I said, "I wanna build a big company." And it's like, if you could accomplish the same thing with two people and no one ever knew about it- Yeah ... would you still wanna build a big company? Like, maybe, right? And they're like, "Eh, maybe you're not solving the problem you think you're solving." Yeah. Right? Yeah. And that's dangerous. It is.

I think it's, it's funny, but the modality is almost this foregone conclusion, which is, of course I must build big company because if it's big enough, then it will cover up whatever this hidden wound that I haven't even fully begun to understand in my, my own right. Sure, maybe. Yeah. But to your point, like, what's the less path of resistance to that same outcome, right? Do we have to take- Yeah ... the most difficult way at this?

Does it have to be that big or could it be a medium or a small company? Well- Well- ... you said something important there though, which is that they're not being disingenuous. They're just not being fully honest with themselves, and therefore it becomes difficult to be honest externally and, and to talk to people about this.

I've got a couple ideas of my own here, but what, what are the most common moments that you see where the founder's why, I'm gonna call it, leaks out, right? Where we start to see it escape, uh, the, uh, the, the sarcophagus and, and, and come to life and go, "Hey, this is why you're actually here." What are those moments? Is it fundraising, some sort of conflict, burnout? Where, where did these things actually start to seep through? You know, you and I have done episodes on this.

It's when people sell the company. Oh. And you have that certain moment where they're no longer needed. All of us at some level need to be needed. Right? So as the organization gets bigger and more reliant on us, on the one hand we're like, "Oh my God, this is such a crushing weight." But there's another part of us that appreciates being needed. We appreciate when people call on us and say, "Hey, we need your input. We need your d- direction. We need

your decision." That is an incredibly validating feeling. Yeah. You know, for as much as- Yeah ... founders tend to write it off like, "Oh, I wish they didn't need me and could operate on their own." No, you wish they'd, like, you don't have to give them the information, but you want to be needed. You might not wanna go to the party, but you wanna be invited. Yeah. Right? And I remember, uh, early in my career when I was, uh, we had sold, uh, my, my agency, and I was basically cycling out of it.

I remember going into a meeting with all of our senior staff, and everyone knew that I, like, 'cause it, the, the agency had been sold. Like, I, I was- Yeah ... gonna be gone. Everybody knew I was gonna be gone in, like, three months. And I remember I walked into a meeting and I sat down, and our COO said to me, "Uh, what are you doing here?" And I'm like- Like, uh-oh ... "Huh? Great." Ouch. It's game day. Like, who, yeah, but why are you wearing a helmet? Yeah, yeah.

She was being a matter of fact. Yeah, yeah. Right? Like, "Hey," like, "you, you don't need to be here." And I remember, like, it hit me like a cannon. Mm-hmm. And I was like, "I'm not needed?" Right? Like, and, and to be fair, that was probably true two years prior. Yeah. I probably wasn't needed then, too. But that feeling that I wasn't needed w- was, was painful.

Now- Sure ... I'm not saying we have to, like, stitch this into every part of our day and every decision we have, but we kinda need to know what's happening. Yeah. Because whenever you see an extraordinary personality, extraordinary personality would be, like, Elon Musk today, Steve Jobs back in the day- Yeah literally every, uh, artist ever, that comes from a very specific place, right? Sure is. Steve Jobs didn't become Steve Jobs 'cause he's just a regular dude. Right. Nor did Elon Musk.

It comes from a brutal history of, like, like, what's going through your head that you're trying to account for. And it allows you in many ways to do great things. You know, the artist's greatest pain becomes their greatest art- Yeah, yeah ... in, in many ways. So this isn't me saying, like, pain is necessarily bad or, or insecurity is, are bad. It's let's know what they are. Yeah, yeah. Because they are gonna shape everything. Yes. Yeah. Know, know your motivations.

And it's, it's dangerous not to know that. Yeah. Yeah. Yeah, yeah. Um, w-

we- Yeah, well, I, I think you, you said it once, w- which was that these things essentially become your true North Star. Yeah. Whether it's conscious or not, these end up being that kind of guiding light, m- maybe more of a magnetic force, right? Yep. Maybe it's the true magnetic north, uh, that we're pulled towards. Where does that come from? I think, like, at its core, you know, w- we all need some level of validation, right? So that's, that's one kind of big bucket, if we will, right?

Sure. And, and I'm gonna go back to the you were the dork in high school type thing, right? There's no lack of founders out there, right, and, and whether they wanna admit it or not, that can't point back to high school and- Something in high school happened where, you know, they didn't get invited to prom or they didn't, you know, they, they got laughed out of the locker room. I don't know, right? You know, whatever your, your metaphor is, and they wanna make up for that.

They wanna go back and show those people, and I'm using high school as just like- Sure ... a metaphor. Show those people that they were wrong. Your parents leaned on you too hard and you wanna show them. You had a sibling that was always better than you and you wanna show them, like, you name it. All of these things tend to, to develop, you know, what drives you and what motivates you beyond wanting to do great things in the world.

And even sometimes wanting to do great things in the world come from somewhere very specific that you're trying to like, you know, map, make up for. But I look at it and I'm like, "Okay, man. If your goal, if what you're trying to accomplish is validation, is recognition, is being seen in all these things, there are a lot of ways to get there. Let's map the best possible way to solve for that problem." Yeah. A- and know which one specifically it is, right?

Because you've- Yeah, yeah, yeah ... you've named off a whole bunch of things there. Safety and control, validation and status, autonomy. Yep. You know, if you can't stand being managed, proving people or silencing your critics, belonging, identity, you know, we want to matter.

Knowing which one of those things it is has a lot to do with being able to make sure that your strategy for how you grow that company, what you build, how you grow it, and what money you take, who you choose to- Yep work with all becomes pretty damn important, right? I agree.

Uh, Ryan, when, when you think about it, w- what's your North Star? My North Star. Look, uh, if... You mean the real one? The, the one I'm not allowed- Yeah, no ... to talk about? The, the fake one. Yeah. Yeah, the, the, uh, the fake one is I wanna make a dent in the world. I wanna make my dent in the universe, Will. I just, you gotta figure out where the boundaries of the universe are so I know whether I'm denting it from the inside or the outside.

Look, I, I think mine is probably a combination of, I think about the five core ingredients there. Autonomy, definitely a, a big part of it, right? It's, is a big one. What, what pushes that though? I think that probably, like, a fairly controlled childhood. There was definitely that. And so the, this, it's all, it all goes back there, right? There were two things. Yeah. One, I mean, I've talked about this before, we were very much an achievement household, right?

You know, there were lots of stories about, you know, my, my father's athletic escapades, the fact that, you know, he came from a single-parent household. Father died when he was quite young. Managed to put himself through university, put himself through medical school, uh, did all these amazing things, and achieved, and achieved, and achieved. There was very much a sense that that was, that was the track that I need to be on.

And so, like, validation and status are definitely part of what drives it for me. But because autonomy was also a big part of it, right, not wanting to follow someone else's path, wanting to be able to say, "I did it my way," meant that the more traditional career path, like become doctor, right, become lawyer, become- Yeah, yeah wasn't gonna work, right? Because there wasn't enough autonomy in that. There was too many other, too many rule sets, too many other people telling me what I had to do.

So I think for me, my north stars are some combination of the, the, the massive gravitational forces of validation and autonomy. What, what else? You said there were other buckets. I'm curious. For me in particular? You know, I think a big part of it was, um, the other... 'Cause I'm, I'm b- I'm just, I'm trying to remember how I labeled the, the ones that you listed off.

It would be like the, well, a bit of the revenge narrative, right? So that, that proving and silencing the critics. As a, as a kid- It's a big part of being a founder. It is. It's a huge part- Yeah ... of it, and I think it's, it's one of those things that kind of sets you up for it. But I think in my case, it does. It goes back to childhood.

There were a lot of people that, that doubted me or that wanted to look at me and go, "Oh, well, you're only that way because your, your father's a doctor," or whatever. And I was like, "Dude, I am the hardest-working kid." Like, I was called the little rich kid, right? Yeah, I was the hardest-working kid I knew. I was busting my ass on the farm. I was building stuff. I w- I was constantly doing something to prove them, them wrong in ways that they never saw. Sure. All right?

So I was just the, uh, I was just the little, the little spoiled kid. I was anything but. And so I think that was part of it, too. It was sort of like, you know, "Well, I'll show you." I go back to that beautiful quote, right? This, this beautiful quote, and I've probably shared this before. I had overdone a project in high school significantly, significantly. Okay. And I was relatively new in high school at that point. I had overbuilt this little model by, like, I don't know, 30 hours.

I spent a ton of time making this little panorama. It was beautiful. Everybody started making fun of this thing, 'cause some of them had, like, literally gone to the library and photocopied a, a piece of paper out of a book, and that was their, that was their presentation. So everybody was making fun of me. The teacher hears this as he walks in, and he stood outside and he listened to the narrative for a minute. And he walks in and he goes, "Go ahead, make fun of him.

Laugh now while you can. When he's signing your paychecks-" it won't be funny anymore. And I thought, like, that was such a beautifully validating, going back to validation, such a beautifully validating moment for me to say that like, look, putting in that extra effort, being autonomous and doing what I wanted to the way I wanted to was okay, right? Because up until that point, I'm not sure I'd heard that, and that was a really, really important moment in my life. Thanks, Mr. Adkins.

You're the best. 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.

I think it's fascinating, though, like again, I, I'm mentioning som- something like Steve Jobs. I remember, this is, I'm gonna date stamp it, like 2010. There used to be a, a media property called Valleywag, and it used to be like the TMZ- Oh, yeah ... of, of Silicon Valley, right? Yeah. And so, and so there was a writer back then, uh, named Ryan Tate, and I'll never forget this. 2010, 2011, it was r- right around then. He gets into a spat with Steve Jobs. Right? Mm-hmm.

He's criticizing, like, the iPad or something like that, right? Right. And Steve Jobs goes back to him and he goes, "Hey, what have you ever done? What have you ever built?" Mm-hmm. "First let's start with what you've built- Yeah and now let's talk about your criticisms." And, and what I loved about that, I loved that even Steve Jobs was still feeling that, like, like he was getting pushed into a locker. Yeah. Right? It hurt. It hurt. The, despite- It hurt, right?

... the absolute... And t- it's so funny because he literally in the next breath, like he's, he's telling you that hurt, in the next breath he's telling you why that person's opinion is completely irrelevant, and yet- That's my point and yet- Right ... it still hurt, right? It's so funny. So I wanna talk about that. I wanna talk about, like, let's say that Steve Jobs was, was guy that got pushed into the locker, right?

And he wants to show the world that, you know, he's, he's bigger, smarter, you know, all these things. Yeah. Uh, which is fine. It's a perfectly understandable behavior. I'm not here to criticize that feeling. I'm here to, to explain it, right? Yeah. And in his mind, if he builds Apple, iPad, iPhone, uh, all these things, right? Then people won't be able to say these things to him anymore, right? And here this, you know, snarky Valleywag reporter, right, gets under his skin.

Now here's why I say that. Truer words were never spoken by Jobs, right? Yeah. When he says, "What have you done?" Yeah. Right? That is exactly the right answer. It is. What have you done, dude? Yeah. You're talking to the guy that built Apple. Uh-huh. Fuck you. Yeah.

Like, straight up, right? So w- when I say this, when people are like, "Hey, I have to build for the haters- Yeah I have to prove them wrong," pause. Yeah. Who are those people specifically, and what leg do they have to stand on to tell you who you are to begin with? Yeah. It took me a long time to figure that one out. Yeah. A long time. Right? And I'm not sure I'm totally over it, but I know that- Criticism still hurts, even, even when you know it's coming from a place of, of irrelevance, man.

Like, uh, like, if it can still get to Steve Jobs, right? Yeah. Who's gonna be me? That's my point. That guy could have literally been like, "You know the iPad and the iPhone and the iMac? I am the I in all of those things, asshole." Yeah. "Who are you? Which part of Valley Wag? Are you the wag or are you the valley?" Yeah, yeah, yeah, yeah. Right. "Tell me." Unbelievable.

The point though is that, like, that ego still fuels him, right? Yeah. And, and Jobs is, you know, famously an egomaniac, but- Yes ... I look at this a- and I think to myself, "What's the minimum viable product that we need, the path that we need to solve this ego problem?" Yeah. You know, minimum viable ego, right? There you go. Like, if my ego is that I feel like my parents always treated my, my sibling better than I did, and I have to show them, cool. That's fine.

I don't care what it is, right? Yep. But let's be very deliberate about what path will solve that problem. Sure. Right? And so I, I can tell you right now, it's, it's not raising 200 million in VC. Right. Unless Unless. Yeah. Unless your dad was Steve Jobs, right? Right. A- and, like, a- and you have to operate at that level.

That's actually... Uh, just made me think about it. Early in my career when I was running the agency, I was very fortunate to have a great partner, a guy named Blaine, who you obviously know. Yeah, yeah. And the agency's doing phenomenally well, right? Like, we're making hundreds of millions of dollars.

And, uh, Blaine, who was super young at the time, I think he was, like, 28, 29, was like, "Hey, that's great, but my dad, you know, started Cardinal Health," which is, like, what, like, the 15th largest company in the world or something like that- Oh, yeah in the, in the US, something like that. Like, Fortune 15 company. So, so we're basically a rounding error- Yeah, exactly ... at $100 million. Exactly.

Yeah. So, so his threshold for what he had to get to was- Yep ... like, you know- Yep ... in the stratosphere. And it was interesting because I was like, "I don't think my dad made over $1,000 in a month." Right. So, like- Yeah. So- ... my threshold of what I- Yeah ... needed to get over to satisfy that claim was very different. I, I have to clear so many bars. Right. Exactly.

And so my point is everybody's got, like, a different threshold of what they- Sure ... think they need in order to clear. But what I always look at it and I say, "Let's get really specific about what your threshold needs to be." What it is. Yeah, yeah. 'Cause I guarantee it ain't that high. Yep. So I'm thinking, um, class of 2005 dork that got pushed into a, a locker and... I wish I was that young. I was gonna say, did, did we just get younger, Will? Yeah. I think 20 years. Nicerly done.

And that's what I'm trying to like, like fight against. I, I gotta prove those haters wrong. Number one, you'll never prove them wrong, right? Right. It, actually, the Steve Jobs example, right? It- there are always gonna be haters. No matter what you do, those people were haters before you came around. Yeah. Yep. And they'll be haters long after you go around. If, heaven forbid, today's your last day on Earth, it's not gonna change a thing about who those people are. Correct.

So like, it's, it... Foolish to try. But the other side of it is, if really what you wanna do is prove to your old man that you can be good enough, smart enough, et cetera- Yeah ... cool. What's the minimum that would take? Here's an example, right? Probably less than you think. Here's an example.

If you had a business that was doing $5 million in revenue, on $2 million in net income- Yeah and you flew private, not all the time, but you, you know- Right, but you can ... you could get your Marquis Jet Card or you know, whatever- Yep ... it was, right? Would that be more than your old man did? Right? Probably. Or depending on who your old man is, right? Probably. Then just do that. Do that. Yeah. Dude, that's a consulting company. Yep. That's it. Right?

Like, like you don't need to raise 200 million in VC and go IPO- No, you do not. You do not ... to get to that outcome. You don't need to build a rocket ship if all you're trying to do is cross the English Channel, right? You just need- That's what I'm saying, man ... a speedboat, right? Just pick- That's what I'm saying. You know, a lot of people, when they start a business, they're like, "My old boss was an asshole, I'm gonna, you know, prove to them," whatever.

Ironically, in many cases, that old boss- Yeah ... is probably you or I. Yep. And I get it, right?

It's like, "I'm gonna show them that I've, I've done this thing." I, you know, I got a funny story. Years ago, this developer that worked for me, like 25 years ago, maybe like 10 years ago, I saw him at a bar or something like that, right? And he had built a new company, like a development shop- Mm ... and they're doing really well, right?

And he was like, "One day I knew we'd see each other again, and I needed to tell you, you know, that I would prove you wrong, that I did, you know, that I, I was able-" Oh "to do this," et cetera. And I remember s- looking at him like, "What are you talking about?" Yeah. Right? 'Cause he, this was like his moment to like- Uh-huh. Oh, God ... prove his old boss that he could really perform. And I was like- Talk about taking the wind out of his sails.

He spent so much time hanging those sails, Will. Good Lord. I was like, "I would be the last person in the world- Yeah ... that would not wanna see you do that." Like, I would be... He was like, "No, you told me at the time it could never be done." I'm like, "Dude, you fabricated all of that." Like, because- I'm glad I was the villain that drove you to s- your success, but, uh, I, I had no idea it was- Yeah. Yeah. I'm, I'm glad that you, you invented the evil version of me.

Also, isn't it hysterical that like- So often when I see founders that are like, they've tried to prove they matter, right? Yeah. Yeah, yeah. Why do they pick the hardest possible way of doing it? It's like- That's what I'm saying ... like, there's so many other ways to have gotten around that, right? Like, maybe just a conversation with you probably would have done that. No, look, it- it's, he needed some motivation apparently, and so that's- Yeah ... that's- No, that's what it takes.

Yeah. But, but I look at that and, and I think to myself, number one, I actually didn't feel that way, right? So like, uh- Yeah ... that was a false pr- premise. Number two, now that you know that you've done the thing, are you good now? Yeah. Because every single person I've ever met has not been.

Uh-huh. It goes back to when we talk about founders who've, you know, finally sold or IPO'd or anything else like that, and they all think that it's that moment that's gonna change everything. Like, like, if I take company IPO, then I wasn't the kid that got pushed in the locker. No. Yeah. No. You took the company IPO and you were the kid that got- Yeah ... that got pushed in the locker. One doesn't like, you know, n- reset the other.

And I look at that and, and I'm like- No matter how many zeros are behind the first digit in your exit number, that photo from middle school still exists somewhere. Yep. Right? Yeah, it does. It's not going away. I was talking to s- somebody the other day about this. I'm building this new house, and they're like, "Oh my God, you must be so proud of, you know, what you're building," stuff.

I'm like, "I am, but like, I'm still price shopping the cost of the outlet covers that are going on- on every outlet," right? Yeah. "I'm gonna save exactly like $6, but like- Uh-huh ... hell, I'm gonna price shop all of those," right? And they said, "Why?" Like, you know, "You've got enough cash, like it doesn't matter." Mm-hmm. I was like, "Because I'm a poor kid that made money." Yeah. "But I'll always be the poor kid." I understand my DNA very well.

Yeah. Doesn't mean I don't deal with it like everybody else. Uh-huh. But I definitely take account for it. But you, you recognize it. Right? Yeah. I recognize where these things come from. And when I rewind back and I look at earlier points in my career, it was hilarious how many of my decisions were driven by a version of me that didn't quite get it yet. Yeah. Right? Yep. That was me in the yellow Lamborghini, right? Right. It wasn't that I needed to get places faster, right? Right.

That wasn't, that wasn't it, right? And what's funny is now that I don't have those same insecurities, the idea of owning a yellow Lamborghini makes absolutely no sense. It is funny. It, like, I almost look at it like in, like, what was I thinking? Yeah. Right? Yeah. Take the douchebaggery off the table for a second. Sure. I'm just looking at it now like, I own a pickup truck. Right. Because it's really practical. Well, that's not your best vehicle.

Your best vehicle is by far the skid steer, right? The Bobcat is- But- ... by far the best vehicle that you own. That's even a level below- Like, that's my favorite ... in some way or level up. I wanna roll up to the club in that thing at some point. Yeah, right. Right. But I guess what I'm saying is, as we start to understand ourselves better, right?

Like, as we understand where these motivations are coming from- It's incredible how different our journey becomes- Yes because we're solving for different things. Yeah. Right? I found, and I think a lot of people get here, I found that over time, the things that I'm, like, optimizing for have very little to do with wealth. It's how I spend my time, like, how I build my relationships, and everybody tells you that. That's it right there. Those two things. Yeah. Yeah. That's it.

But that said, none of that stuff means shit until you've actually made some money, right? Yeah. Because until then- Yeah ... not having cash seems like the biggest problem, so all those things, you know, become a luxury. It is up to a point, and then, and then just isn't. I think we, we've talked about that before too, couple times on the podcast, where just, like, that number is not nearly as high as you think. But, but going back to this, the, the entire kind of minimum viable ego thing here.

Yeah. I, I... In the way I think about, the goal isn't to eliminate the ego. We're not saying like, "Okay, you just almost- Yeah, right ... achieve ego death." The, the goal here is to, to right-size the plan to that motive, right? Yep. Whatever it is within the ego that's driving that.

And so as we've been talking, as I was thinking of a couple of questions that I would, I would probably ask founders or myself, really try to get to the other side of this, which is, like, what am I trying to feel on the other side of success? Yeah. Right? Like, that, the un-dorking, right? Like- Yep ... what will actually make me not feel like the dork anymore, right? Right. Second, like, what's the smallest outcome that would genuinely satisfy that, right?

To your point- Yep ... we don't need a $200 million raise from VC if what we need is a $5 million business with two million EBITDA and our Marquee Jet Card so we can make- Right, wh- which isn't a layup either. I, I don't wanna point that as th- like, that's a concession. Dude, if you get there, you're in the top 1% of people. Yes, but you're not in the top zero, zero, zero point, or .0001% of people, right?

Yep. It, it's going back to, like, what, what path gets me there with the least risk, time, and self-destruction, right? I think is the other one. Because I watch so often, because founders don't acknowledge this ego that's driving from the trunk, that the self-destruction becomes a natural byproduct of that, and that's really, really hard to watch when you just understand.

When you can see it from the outside, 'cause so very frequently you and I are talking to founders, and we can kinda see these motivations and go like, "This one's really got a chip on their shoulder. They've really got something to prove here." Yeah. And I hope they go prove it, but I don't wanna see them wreck themselves in, in the process. Do you know, Ryan, do you know that I've never seen anybody prove it?

I mean, okay- Yeah ... you gotta understand, like, we're- Yeah ... in the business of seeing- In the business, yeah the most successful people become- Yes ... the most successful people. Yep. I have yet to see anybody at any level of success be like- Yeah ... "I'm good now." Right? Yeah. If anything, it actually made it worse. Right.

Remember that quote from, uh, Chesky from Airbnb saying that, like, when he went public at Airbnb, it was, like, the loneliest, darkest- Oh, yes you know, moment of his life because- Yeah, yeah, yeah ... he thought that was gonna solve all these problems- Yep ... and it, like, it actually, it laid all the problems bare. Bare, yep.

Because if, if you've checked all those boxes, and you've made all that money, or you've done whatever you said you're gonna do, and you still feel like crap, that makes it worse. Because now there's no s- there's no solve. Right? Yeah. Like, you, you know, you're as- you assume that I don't have money, so if I have money, then these problems go away.

Yeah. But all of a sudden you get the money and you still have the problems, and now you're like, "Shit, I actually can't get rid of these problems." Yeah. At least before you thought you might. Right. Yeah. Before I see it- That's the thing. You get the hope of it, of it disappearing, and then when it doesn't, then desperation doesn't creep in, it comes, it comes crashing in big Pacific wave. You bet.

I see it in marriages all the time, right? Sure. I see it in marriages where there's, there's a lot of tension be- between the spouses because there's money problems and everything. And look, man- Yeah ... life's hard, right? I get it. Yep. And the idea is that if we had more money, the problems would go away. Don't get me wrong. Yeah. Right? Like, while money doesn't solve every problems, e- every problem, it sure does create plenty. Yeah. Not having it creates a lot, right?

Yeah, yeah. So I, I, I don't wanna take that off the table, but the idea is that if we get the money, it'll solve all of our problems. And it'll solve some of them. Right. It'll solve the ones that money can pay for. It won't solve any of the ones that money can't pay for. Money can't pay for. Yeah. Right? Or like, "Hey, let's ha- let's have a kid and that'll bring us closer together." No, it won't. Yeah. It's just gonna create a whole new problem set that you didn't have five seconds ago.

Yeah. Right? Um- Third person to argue with. No one's ever saved a marriage with a kid, right? S- And... But again, I look at that seeing, like, people look at these external factors that can solve the things that are personal to them. Yeah. And it, like, kinda never works. It doesn't. And it's bananas to me to, to not take inventory of it. It's hard. It's- Right ... hard work because it's vulnerable work, right?

I think most of us, as founders, would rather just continue to grind than to get honest- Yeah ... about those things in particular.

But when you know what you're actually building for, I, I think you stop wandering into the hardest possible version of success, maybe that one that you don't actually need to achieve to feel successful, and start building the right version of success on purpose, right? And, and the goal isn't to become- Imagine that ... ego-less again, right? It's to become- Yeah ... aligned. You know, to me, the most unstoppable founders aren't the ones, you know, with just the, the biggest dreams, right?

We, we know that doesn't work. It's, it's about the probability of it actually coming true. It's people who are actually operating with some sense of the truth behind what's driving them forward, right? Yep. They understand what fuels them. They can harness that fuel and do something good with it.

Yeah. I, I look at it, man, and I say, for me, at any point in my life, whether I was making money or not, all that mattered was my freedom and my autonomy and really- Yeah ... my, my ability to control my own destiny, right? Yeah. That's it. That's- That's it ... dude, that's all I cared about. Right. To this day, it's still all I care about.

Yep. If you were to say, "Look, you could take anything that you have, and now you have a 10th of it, but the one thing you still have is your autonomy," I'm like, "Shit, that sucks, but I'll take- Yeah the autonomy over everything." Conversely, if you said you could have 10 times more than you have, but you have a boss, so to speak, or you have, uh, you don't have control of, of your own destiny anymore, I'm like, "Not interested."

Like, literally the only thing that matters to me is having that control of, you know, of my destiny, of, of whatever it's gonna be. You know, even if the job sucks, so long as it's my job- My job. ... I'm totally fine with that, right? Yep, yep. And I think that honesty that I've developed over time has served me incredibly well because it allows me to say, "No, I'm doing these things for this specific reason." Uh-huh. It sucks.

It puts me in a tough position a lot of the times, but I understand why. I don't think I did before, right? And I think for a lot of people, they'll look at this, right, Ryan? And they'll say, "Yeah, but you shouldn't solve any of this with work. You know, you should, you should be able to fill your bucket with- Yeah ... life, with family, with all of those things," and I think that's exactly the right answer, and I think it works exactly never. Yep, 0% of the time.

Yeah, it's, it's beautiful on paper. It's a lovely, lovely sentiment. Yeah, it's a great hallmark moment, and it- Yeah ... works pretty much never, right?

For the rest of us who aren't quite that zen- Yeah ... um, which is literally almost everybody, here's what I say. It's okay to have these problems. It's okay to be the dork in 2005 that got shoved into a locker, and that's okay. Yeah. So long as you own it. Right. So long as you s- y- you say to yourself, if not the world, "This is what I'm doing it for." Yeah. "I, I'm getting up in the morning, right, and I'm gonna prove to everybody that I wasn't that person.

I'm gonna prove to my old man that I was good enough. You know, I'm gonna prove to whoever I have to prove something to, but this is why I'm doing it, and this is exactly how I'm gonna get there." And when that moment comes that I can finally say to myself, "Yes, I am no longer the dork of 2005. I have officially un-dorked myself," then all of that effort will probably be worth it. 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.