What Should My Expectations Be?

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 founders are probably the only people I know who can work 80 hours a week, beat the odds just to exist and still feel behind why. Because our expectations are unhinged, man, like today.

Let's spend some time talking about like the single fastest way to improve founder happiness and decision making, which is just some recalibration. Yeah. Like if you go back in time, like how reasonable were your expectations when you entered the startup space?

I gotta say, maybe by accident I started with such low expectations going into my startup career, like, and I'm gonna get into some detail just so folks can really appreciate that when I say this, but I started with such low expectations that any kind of forward progress was like holy home run. So to give you an idea where I was, by the time I had started my first company, mind you, I'm 19, I'm in college at that time, my thing, I was living in the, in the dorms at Ohio State.

My thing was I would write your term paper. Oh yeah. Whatever your term paper would be. Um, on, on literally any topic in under a half hour, which is bananas for the cost of a pizza. If you would buy me a Papa John's pizza, it was like $10 Uhhuh, like that. That was my going rate for my consulting output. Now the irony was I had never written a term paper of my own in my life. Right. But I was just a good writer, so I knew how to write Flower reward. Yep. I'll write for other people. Exactly.

It was always way better than that person. Write for great rates, but I'll, I'll write for pizza. Right, right. And so, uh, anyway, that's where I was at.

And you know, it's funny we should say that 'cause we've told the story before where like, I had built a website for ribs for a $500 gift certificate, uh, for a rib place. I did mine for a $1,500 tab at Victorian's Midnight Cafe, which never expired because I think it was, and it never expired. I think they forgot to track it at some point. 'cause I was just like, three years later I'm like. I'm just thinking about the price of a grilled cheese.

I must have eaten 500 of these things at this point. There's no way I still have money left with these guys. There is definitely a time, it's funny that you and I were basically selling into the same local, uh, small business pool of Columbus, Ohio back then, and there was a time where, where I, uh, walked into a restaurant, it was Damon's, the place for ribs, and I'd convinced the, uh, manager to let us build a, uh, website for them.

This was like in 96 and uh, in exchange for this $500 tab, right, for food. And I remember going back to the office and explaining to the team that I had just sold a website for $500 of rib value. Yeah. And it was a high five fest. Everyone was so pumped up, like they could not believe we could make rib money. Rib money, uh, with our capabilities. Right? Yeah. Yeah. 'cause you could see that story going the other way. Like at this point, like you, you founders hearing this, they're like, oh.

He goes back and he tells the team and they're like, it's Jack coming home and telling his mom he sold the cow for three magic beans. Right. Uh, no sir. Food is food. No, it was, it was slower. So I say this to say to, to put some color around this. That was my level of expectations.

Now, the funny thing to that, this is like circa 96, going in 97, a year later, in one of the most dramatic turn of events ever, we would have one of the most. The biggest agents lopsided agency wins in history. Uhhuh, we won a quarter billion dollar a year piece of business that would enable us to go public years later. A of right. That's a lot of ribs. And I remember when I was up there, I was up there on stage 'cause this is like back then big agency pitches.

But I remember being up there on stage at Eli Lilly, uh, that we were pitching in Indianapolis. Thinking, I'm pitching Lily right now, and this is a multi-billion dollar, like top of the food chain Fortune 500 business. But like nine seconds ago, yeah, I was selling these same services. Yeah. For a $500 gift card, I had to wash a barbecue sauce off my hands from the ribs I just ate for my last paying gig. Uh, it's amazing. But here's why we're talking about this.

We're talking about it because when founders go into this business, the business of startups, I think our expectations are so incredibly broken. Yeah. And they're so malformed so many times that when we get get into this business, we start building these businesses, we are wildly disappointed. Yeah. And, and I think it's a broken setup. It is. I think that's why it's so important to talk about this today.

Yeah. Right. It's, it's not just that our expectations are wrong, it's like, okay, so what, like. When I think about it, our happiness is really just kind of a math problem, and it's reality divided by expectations. Right? Right. When we get that, we get the denominator wrong. It causes a lot of trouble, and I tell people all this all the time. I said, your happiness is proportionate to your expectations. That's it.

If your expectations were sky high, you're likely not happy because you weren't able to achieve that. Yeah. Now, I'm not saying let's all go for super low expectations just so we can be happy. There's a calibration to be had here, right? Sure. But that's what we'll talk about. And I think for a lot of folks, there's an entitlement that comes with this. I think that's part of it, and we'll talk through that. Like, you know, what are you not entitled to? What are you entitled to, et cetera.

Yeah. But I think overall, if I look back on, you know, a 30 year plus career, the highlight of everything has been, whenever I achieved something, it was so much more than I felt entitled to. And we'll talk about this, but I have a strong feeling about entitlement. Right. And so for me, you are entitled to what you earn. Yeah. Again, we'll talk about that.

Yeah. But I think that for me, I always felt like when I earned something, I was over the moon because I'd never thought I was actually gonna get it. Right. If anything, Ryan. If I look back, and I have many countless memories of this, I kept waiting for the other shoe to drop. Sure. I think to this day, I still am. Right? 30 years later, 30 years later, I'm still waiting for someone to, to come and it all the way. Somebody coming to tell me none of that was real. You can't have any of that.

Give it back.

I'm going to tell you a quick story. About a year or two after we won that big pitch, I, um, I bought a Lamborghini. No, I remember it. Right. Yeah. I, uh, I went in the dealership and I got so hosed over this thing, like, it was, I, I was like maybe 25, I don't remember. And, and I remember I went into the dealership and the finance manager, you know, has me in his office and he's like, you know, in price of the car, blah, blah, blah.

And I, at the time, I didn't know anything about car leases, which is ironic considering I'd be a CEO of a car leasing company. But, uh, but anyway, he's like, and your payment will be like $6,500 a month. You're like, deal. Just pause on that. Yep. My mortgage at that point was $1,475 a month. Yes. Right. To give you an idea of, of like the disparity here and rates weren't all that good back then, right? No. And, and, and I had no credit. Right. I was so young.

Right. And so I remember my rate on that was like 9%. Just like expensive car, insane rates. 'cause nobody was financing a 25-year-old back then. Right. And I remember a buddy of mine from back home in Connecticut was with me at the time to do this deal. And he was like, are you out of your mind? And I was like, honestly, dude. I probably have this thing for three months and they repo it. Right. There's, there's no way a guy like me right. Is ever gonna be able to, onto This's, gonna make, yeah.

I'm not gonna have to worry about what tires cost. We're not gonna get that far. I was like, it doesn't, I'm gonna make a difference because there's no way I'm ever gonna be able to hold onto this. Right. Yeah. And I just, but it goes back to my expectations. Yeah. My expectations were this is way beyond what I deserve. Yeah. And so when it didn't get repoed, like amazed, right? Yeah. Feels great. It feels great.

And so I have always been very mindful of not only my expectations, but everyone else's as well.

And I think where this starts, and I wanna dig into this first, what I call the snowflake myth. The snowflake myth is basically saying, I'm a special snowflake. I'm gonna start a company and it's gonna become IPO, you know, Uber, Amazon, or whatever. Right? I deserve that. Yeah. Right. How do you think about when you talk to founders, do you see the snowflake myth? I do, and I think it comes from a couple of places.

I want to talk about expectations and optimism. Okay. So I think that there is a required degree of optimism when we're founding something because it doesn't exist yet. We have to be optimistic that we can figure out the 8 million problems that we know about in the 15 million that we haven't thought about yet. Right. And generally speaking, I don't think that founders suffer from a lack of optimism. I think we suffer. From unpriced optimism. Right?

And that's where those expectations Love that phrase. Yeah. Yeah. Come into play. So I think that this is where things start to go wrong, and I think that somehow we confuse those unreasonable expectations with that optimism. And when those two things start to get conflated, then all of a sudden what seemed like, okay, this is what's gonna drive us. This is gonna be the force, this is our vision. Unreasonable expectations aren't motivation. They're, they're self-sabotage at some level, right?

They push bad decisions and then they punish you for just achieving what you were otherwise going to achieve anyways and should have been happy with. And so I think that's where this begins for me, and there's a lot of this in our world, in the startup community. I mean, it's. Infiltrated with it at every possible level. Yes. Right? Yes.

So one of them is the defacto that when I go to raise money, I've gotta be able to show investors that this could be that snowflake opportunity. That's it. Right? I've gotta show them that. It could be the, the big IPO, but I've run the numbers on this every year just to see if, if this number has changed, but essentially the probability. You'll be able to get a company to the public market versus the number of people that start companies.

Yeah. In just the US alone, which is by far the most fervent market, where you're probable to do it is 0.000. 3%. That's the probability that you're gonna do what you said you're going to do, and there's 150 companies a year that do it. Adding that percent to the end of it made it hurt a lot worse. Will that added two more zeros? I thought we were just a not enough zeros. That really sucks. Yeah, it's a lottery ticket with a pitch deck attached.

The reason we start here is so we can just use hard economics. It's like when somebody says, I wanna grow from be president, you're not going to Right. Well, I can you, you can, but you will not. Right? Yeah. Like, or I wanna play in the NBA. You can, but you will not. When people hear me say that, it pisses 'em off. They were like, how, how dare you question someone's ability, you know, to whatever. And I'm like, look, I'm not saying, I don't hope you get there. Right, right.

And I'm not saying don't try. Right. What I'm saying is don't expect, don't expect it. Right. That's the danger. Yeah. Because when you set the expectation, you then are are accountable to the failure of it. Okay. Yeah, you are.

I mean like, and I think maybe I should have said aspiration before when I said optimism. I think optimism plays a role in this too, but aspiration is fine. Aspiration is fuel. Right? But expectation becomes this debt, this blocker. Exactly what I was, I was gonna use the word debt. Yeah, yeah. It becomes a debt, right. And I think that hope is fine, but certainty in most cases is delusion. You can't be certain about anything, and I think that's expectations. Based in certainty, right?

I should have this, therefore I will have this right. I want this and therefore I, I will get that. And that's just not the way this thing works. And look, on the one hand, I love the fact that the snowflake myth exists because the idea that, you know, we're all special in some way is wonderful, right? I think that's wonderful. However, the difference in the startup world. What you just said, it becomes a debt. And here's specifically the moment it becomes a debt.

When you go to an investor and say, give me money in exchange, I'm going to give you back this return. You know, this return being the IPO, et cetera. Yeah, yeah. And now you owe that expectation when you give stock options to your staff. Right now you owe them that expectation. Yeah. That locks it in. And we're in a world exactly where it changes the calculus. Yeah. Because you are accountable to that expectation.

That's it. One of the things that I think, Ryan, we've done well@startups.com, is we are very incremental in those expectations. Right? Yeah. You know, uh, we look at the expectations and say, we would love to get to that, you know, to that point, oh oh, oh, you know, 3%. However, yeah, here are the other milestones that would also make us very happy. That's it. Like being profitable, making payroll, you know, crazy stuff. And I think because of that we don't tie up.

All of our happiness to a likely incalculable goal. Right. And again, to your point, doesn't mean we're not, we're not aiming for that. Right. My right. I have to, I have to bring back my dad's quote, which was, you know, aim for the moon, clear the fence. Yep. Right? Like it's fine to have that aspiration, but you still gotta put in the work. And I think the minute you replace, we're going to be a unicorn within a year or two, we're gonna earn our next three wins.

All of a sudden you're actually gonna start to make progress because they don't think that anybody knows what it actually means to go be a unicorn. Like what? What exactly is the checklist to get to that? Whereas go get next three clients has a checklist. We know what to do to go do that. Right, right. Well, and let's separate these two. 'cause I think this is where folks may be missing the point aspiration. Yep. And expectation. Yes. They're not the same thing. Not the same at all.

Aspiration is where I'd like to go. Expectation is where I, where I expect to go. Yep. Right? Aspiration is it might happen. Expectation is it better happen right now. It doesn't have to be one or the other. For example, I can say this. I would like my company to be a unicorn. Right. Yeah. Cool. That's my aspiration. Nothing wrong with that. We're, we're not knocking that. The difference is we're saying, but right now I need to get to the company where it makes a thousand dollars a month.

That's it, right? Yep. My expectation is I, this thing has to get to a thousand dollars a month of revenue. It's the equivalent of saying, I need to score a home run. But saying, but don't you want get on first base first? Yeah. Nope. Just want, just want home runs. Yeah. Right. It doesn't quite work like that, but here's the difference.

When we say, Hey, if we get to a thousand dollars a month in revenue, which again I know is peanuts, which is why I'm using that number, it's not that we pack our shit and go home. It's that like, okay, this is what a thousand dollars buys us, doesn't buy us, you know, not paying our salaries or anything else like that. Right. It's proven the market a little bit. It gets us, you know, to product market fit maybe, and it allows us to start playing the, does it scale game a little bit?

Yeah, but that's an expectation. My expectation right now is I just wanna make payroll. My expectation right now is I just wanna get product market fit. My expectation right now is just, I wanna make enough money that I'm getting paid more than my last job. Like to me, those are very reasonable expectations. Right. Even if the aspiration is, you know, shoot for the moon. Yeah, and that's the thing.

You can have really, really high aspirations and then simply just base the work around practical things to get towards that, that outcome. When do you think that dreaming becomes most dangerous? What are the triggers? Is it fundraising? Is it hiring, social comparison with other, with other startups? Where do you think this starts to go off the rails?

I think it starts with time. And you know, you and I deal with this all the time when we're working with folks and we deal with it in our own expectations. Sure. I think founders, because they don't understand how this business works very well, why would you probably doing it for the first time? This stuff takes a lot longer than people think it does.

Yep. The myth around time, of course, is that, oh, well within a year we'll have product market fit, or the month we launch, we'll know right away whether the product's working, which is works, never, or you know. Within a year we'll be profitable, or within two years, you know, we'll have raised our next round, et cetera. I was like, look man, I've been doing this for over 30 years. Yep. It does not work like that. Doesn't work.

You know what I've started to do Will, every time I hear these numbers from founders, I just apply dog years math to it. I'm like, okay, just I think you multiply by seven the first year six, this ain't right. Just like that's the sad reality of it. My rough math that I always use for people is what I call the three x rule of time. Mm, however long you think it's gonna take, just multiply it by at least three. Yeah, and I'll give you a, a couple of things.

When I ask people how fast did it take, the fastest growing companies to get to the level they're at, Uber was one of the fastest growing companies. A lot of people didn't realize LinkedIn was one of the fastest growing companies. Yeah, it was. Google was one of the fastest growing companies. Right? I mean, these are the best of the best of Airbnb, right? Total juggernaut. Do you know the time it took those companies to get to to IPO was all over 10 years. Yeah. Right.

Every one of them passed the decade before getting to ipo, growing companies in frigging history. Yeah. Right now, but somehow five years is your plan. Cool. Yeah. Right. Cool. Look there. There's all kinds of reasons why that happens, but when people are like, Hey, we're starting this thing, we're six months into it, we don't know if it's working. I get that like in six months you usually don't know that it's working. Yeah, but you need at least a couple more years. Are you?

Why are you worried about that at that point? To be my question? You don't know any better, and so I think this is an expectation. Hey, I'm already 18 months into this and we're not making any money. Yep. Yeah, you're not supposed to. It'd be great if you could, right? Yeah. But it takes way longer to be able to turn this thing around. Yeah. But people don't really know that. No, we don't talk about that much.

And that, and that's why like the startup timelines, uh, from the early founders, they're fantasy. It's not, they're not forecasts. It's fiction. Right. And, and that's okay. Their job is to go make that true. But I think the, the problem becomes, again, when there's expectations aligned with that and the sense of entitlement that, because this is what we set out to do, this is what we're gonna do.

Again, you've gotta believe that you're gonna hit it, but you have to plan for not hitting it, because statistically you're not going to.

We're also in a business where time is a a very critical element in as much as when we go to raise capital. When folks raise capital, they're typically raising capital for an 18 to 24 month window tops. Yep. Right? And the idea is that you're likely gonna be out of money by then. That puts a very specific constraint on time. Dude, you're about to run outta money, right? Like this thing either has to be successful or you are effed. Right?

And I think that puts us in a, a weird spot where we're constantly under the gun. We're also in a business, particularly among like a lot of the faster growing startups where you happen to be competing with everybody else with the same idea at exactly the same time, same time. Yep. Let me zoom out a bit, Ryan. If you and I were starting to call an ad agency right now Yep. None of this would be on the table. Correct. Our speed of growth would not make a lick of difference. Doesn't Not at all.

Right. Think we're the first people to start an an ad agency. Right. Or freaking any services business for that. Any services business. Yep. Right. We wouldn't be concerned whether we raised them up capital because there wouldn't be any, you know? Right. Capitalism doesn't fund services business. Yep. And we would just year after year, month after month. Look for deals, try to bring it in.

Clients, try to make money on it, try to, you know, go hiring around it, and it would take as long as it takes. Yeah. Again, the reason I'm bringing this up by comparison, and by the way, that's a very healthy expectation and pace. The reason I bring this up by startups, by comparison is somewhere along the way, we're told that if we're not right in 18 months or 24 months, that we're a failure. Yeah. Yeah. Not true. And it's like not really right. Not really somewhere else works at all.

No. The startups don't fail because they're slow. Right. They fail because founders panic at what would otherwise be normal speed. Right. Because their expectation is that they should be going faster. And look, and this isn't about like being productive in like, you know, in, in getting your work done. Yeah. Yeah. Ryan, you, me and the rest of the team, we are productive as hell. Yes. Right. But we also have a degree of patience, and I think this has been a hallmark for us for a very long time.

We recognize how long things take to actually build. Yeah. You know, we launched a new product last, last month, and our expectations for, for month one growth, I think were very, you know, conservative, but by conservative I mean realistic. Yeah, right. Realistic. Yep. And because of that, we are happy with it and it's not, 'cause we, we set the bar so low that we could easily jump over it. Right, right, right. We know what the bar was supposed to be reasonably. Yeah, right.

I think look, if you start to expect miracles on a schedule, expect to start making really desperate decisions on a schedule too. Right. You just, this is the problem. I think people, again, people's expectations are just so outta whack. You know? I think the good news is. Getting out of your own head, getting off the whiteboard, getting out of your spreadsheet and talking to some other founders solves this.

Most of the time when you look around and everybody else goes, did you just say three years? And they're going like, you plan on six. And you're like, well, what about you? You say, same thing. Same thing. Same, same. Okay, so everybody here thinks it's gonna take me six years, it's probably gonna take me six years. But when all you have, or is the echo of your own voice in your head, how else are you supposed to to, to have better expectations?

It's exacerbated by the fact that the mythology that surrounds our business. Yes. Which is a big part of why we do this show so folks can finally hear how things really go. If you're listening to a popular podcast where they're interviewing a founder, the reason that specific founder is getting interviewed is because they did something out of the norm. Yeah. Right. Like, you know, years ago when we interviewed Brian Chesky, right? Yeah. From Airbnb.

Yeah. He was interesting because he did something out of the norm. Yeah. Bringing somebody on a, how many freaking pitches do we get for people to come onto our show, onto this, onto our podcast? Which is ironic 'cause we don't have guests, right? Yeah. Which what I, I just have to call this out 'cause maybe somebody will hear this. Maybe somebody will hear this. I love the pitches where they're like, I absolutely love the podcast. Your episode on whatever, whatever was amazing.

I have this guest that you should check out. Like if you love our podcast, you may or may not have noticed. You should have noticed. We don't do guests, but Yeah. Right. Still get up offers every day. We're flattered, but we're not accepting. Yeah. I love the flattery though. But, but the point is, what you're hearing, you know, as, as the kind of the, the outside narrative is that startups grow at these incredible paces.

Yeah. You're seeing either a huge funding round or huge outcomes, et cetera, and that is true for a tiny, tiny, tiny percentage of startups. Yeah. That world actually does exist, and I gotta say. I know a lot of those jokers, you know, the founders behind those companies, and I say jokers because they're all great people. I've seen them do seven other companies that had nowhere near the growth rate. Yeah, this one caught heat and I've been at it too. I've like, yep.

I've had a moment where I've had a company catch heat and do really well. I'm companies that went nowhere at all. It's not nearly as controllable as people think it is. I would say reasonable growth is fairly controllable hypergrowth, where you just hit lightning in a bottle. It's more found than discovered. Like you just, you happen upon it. Right. And I think for a lot of folks, the expectation of how much investment this takes from a time standpoint is really broken.

When I sit down with founders, I said, cool, you've got this new idea. It's gonna take you about 10 years for it to become something. Yeah. Their heads explode. I know. They don't want to hear that. That's a really short period of time and we're kind of in a spoiled world. Yeah. Ryan, if you went back to like our parents, uh, growing up, right? Oh yeah. And told somebody you could be successful in 10 years starting a business, they would, they'd be the opposite.

They'd be like, that's unheard of. Businesses used to be. They take multi-generations to be come successful. My grandfather started it. Right? Right. My, my father improved upon it, and we finally became profitable. You know, when, when we took it out, right? It's, that's the way it was, but yet now we have this. This sort of instant gratification challenge if you're thinking about like, 'cause there's all kinds of timeline lies that we can tell ourselves, right?

Yeah. From product to marketing to building credibility, building team, there's all kinds of timelines that we operate on. Right? Is there one that you think is more dangerous or more damaging? Uh, in terms of the timeline? Lie for founders, 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 dayLong@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 how long it takes to build a self-sustaining company, like a successful self-sustaining company. Yeah. And my answer is always five to 10 years. Five if you're lucky. 10 if you're reasonable. Right? Yeah. And that seems to run in such stark contrast to what the expectations are, which is hilarious because I don't know where these expectations come from. Right, right. Again, I equate it to, hey, I, you know, listened to Chesky on the podcast, but like.

By the time chess, he went public, he had been at it for 12 years. Right, right. It didn't happen overnight.

Right. The overnight success. Right. We, we, we went from not being on the NASDAQ to being on the NASDAQ overnight, but the path up to that was quite long. And even then, you know, someone's gonna be more cynical and they'll say, yeah, but you know, uh, that was when we went public, but they were wildly successful five years before that, or six years before that, so it was really only a six year run. I'm like, cool. Yeah. And how many people actually get to that threshold?

It's the Powerball mentality. Yep. Well, you know, uh, I only need one ticket to win. Yes. But the probability that you're going to win it is incredibly low. Yeah. So you don't wanna invest all of your expectation on that outcome. You need to dial it back and say, what's a reasonable outcome for where I am now? And set the expectation around that.

Yeah, I think if I'm forced to pick one, it's the funding timeline, and I think there's two challenges with the funding timeline. It becomes a foregone conclusion that we will raise in 90 days and it becomes a foregone conclusion that we will raise, right? Neither of those two things is certain, and yet I watch founders. Plan around this stuff.

And I think to me, that can be one of the most damaging lies that, that founders tell themselves when they're, they're planning for those, those outcomes, both the timeframe that it takes and the fact that they are certain to just go and raise that capital. Because then they build the business around it and they're like, well, who cares if the runway goes past 90 days? Because that's all we need. That's when we're raising.

And, and it's, it's certain, I think this is where people fall into one of many entitlement traps.

I'm a huge fan of the, uh, philosopher a Rand, the author of Atlas Shrugged in a few other books, and, and she was as shrewd as they come. Like, when you go back and, and you listen to her interviews and stuff, I mean, she's painfully shrewd. Yes. But one of the things that she would always say was, check your premises Uhhuh. You know, whenever you're not sure where you're at, check your premises. Like, how did you arrive at this place? Yes. Right.

Like, what are the things that you thought were foundational knowledge that you based all of these expectations on? And were they actually true? Right. Check your premises. Hey, I think this thing should be successful in three years. Based on what? Based on what? Right, right. Where did you get that foundational knowledge that sounded like it was statistically relevant? That you should be comfortable? Yeah. With, with that decision, it was, it's grounded in a very specific theory.

Will it's, I have exactly three years before my spouse will kick me out of my house. If it's not working by then, I didn't get that far. That's actually very reasonable. Yeah. But I think here's what ends up happening.

We get into what I'd call an entitlement trap. Yeah. An entitlement trap to me. Is, I deserve my expectations. Yeah. I deserve my expectations because I expect them. Right? Yep. And I, uh, I was telling you, uh, before the show that I was talking to my, my wife about this last night and I was talking about like the expectations and the entitlement of our kids.

Yeah. And I said that I get the fact that, you know, where I came from, you know, being a poor kid and where my kids are coming from, being a not poor kid are very different. Yeah. And so. I don't have an entitlement trap because I don't feel entitled to anything, but they do. They do. They're great kids, right? Like incredibly kind and sweet and honest. Right? But their expectation, their baseline is so much higher, just by definition.

Yep. And so when they go into this world and they have these expectations, and again, a lot of it's just implied, like we go on nice vacations, so when my kids go on a shitty vacation, which isn't even a shitty vacation, like right. They're gonna be like, what a dump. Yeah. Right. Not because they're in a dump, probably back then would've been nice contrast vacation I ever went. Right, right. But that's, that's their comparison. I think the same thing happens with founders.

I think founders are like, well, I believe this is gonna be the next big thing, or I wanna be, you know, this next big thing. Yeah. So they feel entitled to that outcome. Sorely disappointed when they don't get there, which is most of the time. Yeah, that's, I think that's the challenge.

Right? And And unfortunately, startups don't reward efforts. Right. There are no payouts. It doesn't guarantee any kind of an outcome. Startups pay for results, not your suffering. Right. If only it were the other way around, we don't be rich, let's call on that. We're used to jobs. Yeah. Where you're supposed to be rewarded for hard work. Yeah. If you work more hours, you get paid more. Yep. So I think.

At a societal level, we are absolutely, we feel a, a absolute entitlement to compensation for effort. Yep. If that's the way you feel, you are in the wrong business. That's exactly it. Yeah. Time invested does not equal value delivered. And if there's no value delivered, your startup's not gonna grow. It's not gonna, it's not gonna achieve anything. Right. It's also your fault.

Yep. Which I think a lot, a lot of people have a hard time wrapping their heads around, like they're like, but I worked really hard at this. Yeah. Did it work? No. That's your fault. Right, but Will, but you just stumbled across it. There is one thing we are absolutely entitled to as founders. Accountability. Accountability, right? Yeah, exactly. That you are entitled to 100%. I don't have like a, a lot of very strong ideologies, but one that is very, very strongly about is you deserve nothing.

You didn't earn. Yeah. You deserve nothing. You didn't earn. Yep. Uh, and I gotta tell you, not popular at cocktail parties. Uh, probably not. Yeah. Depending on who, who your friend circle is made up. Yeah. I was gonna say, there's a lot of people with shit they didn't earn. Right. And I feel I'm not a jerk about it. I'm not trying to like berate anybody about it, but conversely, I, I also feel very serious about what I have earned.

Yeah. Right. In other words, I've put in the work and I've had the outcome and I've earned something. I feel a hundred percent entitled to it. Yeah. What I don't feel entitled to is anything I didn't earn anything else. Yeah. Yeah.

And, and I look at it from the standpoint of this recently come up in, in my life inheritance. I didn't inherit anything, but I, but, uh, we had somebody else in our family that inherited an awful lot of money, right? And, and they were arguing that it wasn't enough and all these things, and I'm like, Hmm. The guy who had to work for that Yeah. Felt very differently about whether that was enough money, right?

And here you are getting it for free and complaining about it at the same time, and it just. Burns me, man, because I'm like, you didn't earn it. Right. You didn't earn it. And so you're not entitled to it. And I know like, again, it does make the most charming person at cocktail party sometime, although I keep wraps on it. I just talked to Sarah about it on the way home.

Here's another example, and this is really gonna make everybody hate me when someone's kid talks about their family's wealth as if they earned it. Yes. Yeah. Ah, for interesting that when you say kid, that can also be like a 45-year-old. I've, I've run into those kids. Oh, yeah, yeah, yeah, yeah. And I'm like, listen, it's great that you have it. I don't, you know Yeah. Grudge you for having it, but you don't get to brag about it. Right.

Yeah. Like, conversely, there's another guy that I know, Ryan, when you're over my house, did I show you that that house that got built, like across the way that looks like a hotel? You know what's funny? I was just talking to our, our mutual friend who happens to be visiting me right now about that exact house came up in an entirely different context and we were laughing about it. Yep. For folks listening.

There just happens to be a guy that, that sold a company for like billions of dollars and, and I live in Ohio, right? This is in Beverly Hills. So the, the point is how, how bizarre this is. Yes. And he lives like across the street, not literally across the street, but you know, whatever in, in Sightline. And he built like a 50,000 square foot house. It's the pet by this. Yeah. I mean it is absolutely. When you drive by it, it actually looks like a hotel.

Anyway, that's not the point of my story. Last year or year before his son. I happened to be working out with me. Like me, me and another founder were together working out. He joined us to work out. Nicest guy in the world. Right. And what I loved about him so much, they have this insane car collection. It's all over the internet, by the way. And you know, he kind of manages the car collection among other things. Right. He's posting about it on Instagram and every long time.

But the way he talks about it is in such reverence to his dad Uhhuh, which mad respect. Yes. Right. He's like, here's what my dad did. Here's how, you know, he's, he's clearly so respectful and he feels so rewarded by his dad. Yeah. Not entitled by him. Right, right. And to me, I was like, hallelujah. Man, difference. Yeah. Yeah. But I'm gonna take this back to this sense of entitlement. We have this feeling that the world owes us something, that our startups owe us something.

Yeah. And that is true to the extent that we've earned it. Our output rewards it. Yeah, here's an example. A buddy of mine goes out, he raises like, I think like $70 million, uh, for a startup, puts like 10 years into it, which is a long time. Yeah. Right. And it kind of just goes sideways, meaning like, it, it's not that it totally blows up, but it, it's, he's never gonna get his money back out of it, ever. And of course he's bemoaning that fact.

He's like, dude, I put 10 hard years into this, right? Yeah. Like, I feel like I deserve a lot more than I get. And I was like, I love you. You don't deserve it. I said It would be nice. You deserved it if you earned it. Right. Right. Like if your output, you and I have plenty of efforts that we've put into things Yes. That yielded zero results. Yeah. Which means that's exactly what we've earned, what we got back from it, and that's what we expect to get back from it.

Yeah. It sucks, but it also goes the other way. It goes the other way where when you know, I've got another buddy of mine sound, a friend of mine that you also knew sold his company for a billion dollars, right? Yeah. And families are interacting all the time and every time I I see him, I'm just so proud of him. Right? Yeah. I'm like, you've earned every nickel of that. Yes. It's an outsized outcome. You didn't expect it necessarily, but you did earn it, and you've earned every nickel.

One of the things that I always say to a founder when they've cashed out. I always, I'm, I'm hoping, I'm, I'm not the only voice, but I get the sense that I am. Sometimes it feels that way here. Like, you're the only person who said something nice to me about this. I'm like, I'm sorry to hear that. I need you to hear this from at least one person. Yeah. You deserve every nickel that you just earned. You deserve every square foot of the house you just bought.

Yeah. You deserve every square inch of the car you just bought. You deserve what you've done. Yeah. And Ryan, no, it's crazy. Almost 99% of the time, they're like, you're the only person who said that. Yeah. Oh, everyone else is looking at them with jealousy or skepticism, or you name it, right? Like right. It's tough. It's tough, but again, Lord knows how entitled to that person's outcome. You're like, why couldn't that have been me? Because it wasn't a lottery ticket.

This wasn't up to random chance. This was up to somebody putting their pants on the line every single day and doing something to earn it different if they're a Powerball winner, but this ain't that. Right. So here, here's what I think, I think the key for us, you know, uh, as, as founders is we've gotta set reasonable expectations. Yeah. I think the expectation battle for founder mentality is real. I think it's real. I'm gonna go back to the thing at the very beginning about the optimism, right?

You're, you're told, you're constantly in pitch mode as a founder, right? And you're, you're constantly having to say things that aren't quite yet true, right? You're projecting out to this, this future and you wanna make everybody else believe it's true. And somewhere along the way you start to believe it's true and then you start to feel entitled to, to that outcome.

Question for you will, one of the things that I, I'm curious about, 'cause we do run into this all the time before we get to setting the reasonable expectations. How are we able to help a founder understand that they're not entitled without crushing them? Because I feel like some of the stuff we've said today, it's, it's kind of heavy. And some of them are out there going like, well, how am I supposed to feel? Right? Like, you guys are just being mean. What am I, what am I supposed to do?

How do you tell a founder that you're just not entitled in a way that that doesn't completely deflate their balloon?

You're entitled to your next milestone, right? Yeah. If you earn it. So if we're torturing the baseball analogy right now, your only focus and your only expectation is to be get on first base. Now that doesn't mean your aspiration isn't to go further. Yeah. Right. But you haven't even gotten onto first base. So talking about how you're, you've got a home run in the works is bullshit. One of the most famous cases I see on a daily basis is when, whenever anybody raises capital.

Yeah. And like, oh, you know, look at this. We won with a huge valuation. We raised a bunch of money. Yeah. I was like, you haven't sold a goddamn thing. You haven't, and you've just added a massive liability and you have less equity now. Congrats. Yeah. I was like, you haven't earned a goddamn thing. Yeah. Now, don't get me wrong, it's hard to raise capital. I, I'm not knocking the milestone. What I'm saying is. Don't replace that with market success. Yeah. Right.

Like all you've done is create liability. You still have to turn that into actual success and statistically you're not going to do it. Yeah, right. So like a typical vc, if they have 20 portfolio companies, and mind you, this was the best of the best of the best of the best that made it to that point to get that investment. Yeah. 18 of those will likely fail. Yep. Right. That's the best of the best, theoretically, being vetted by the best of the best. Right, right.

And still 18 are gonna fail, not two are gonna fail. Just like through some weird happenstance, right? No, most of them, the actual, the vast majority. And so in every case they said, oh, we've got the money, you know, uh, the expectations, blah, blah, blah. IPO. It's done almost literally every pitch deck. But at the same time, I'm kind of like, you know what would've been a really cool expectation? I don't know. Profitability, self-sustaining, you know, a business model selling anything.

Like selling anything, generating revenue. Right. And I think when we start to align our expectations. With what we can actually achieve. And this isn't about lowering the bar, it's about setting milestones. Say that again. Right. We're, we're not saying to just aim low. Aim small. And you know, because reasonable expectations aren't a single destination, they're just a compounding ladder. We're just saying like, you know, build towards that next point and then continue to build from there.

I'll give you a real world example, 'cause you and I were just talking about this. We're launching a new product. We just launched a new product, yep. Weeks ago. And our initial expectation. Is that we wanna sell $200 a day a day of this product. Yep. Okay. Now pause right there. Most people when they hear this, in fact, I had to explain this to my family at the dinner table, why $200 was so meaningful to us. Yeah. Right. And my daughter, who's, you know, 14, she's smart as hell.

She's like, dad, that doesn't sound like a lot of money. Uh, and I was like, it's not, that's not the goal. That's not, I'm not saying $200 and let's go, go home. Right. I'm saying in my expectation is $200 until we get to $200. Yeah. Because me saying it's $200,000 a day. Yeah. Who cares? Yeah. Like funny. That's not my problem right now, think about 200,000. You have to pass through 200 to get there. Right, right. You have to pass that. So, right. I, I think that's the thing, right?

You know, short windows, aggressive and, and, and realistic outcomes. I'd much rather see every founder out there trade one heroic goal. For 10 achievable wins because that turns into heroics at the end. You know the example I always use with founders that I think resonates with everybody, so I'll use it again. Whenever I wanna lose weight. I never talk about a goal that I wanna lose. Mm. I never say that I wanna lose 15 I I know that I wanna lose 15 pounds, let's say. Yeah. Right.

I know that's ultimately the goal, but I have to lose one pound. So I always say this, whenever I'm trying to go on a diet or whatever, my goal is to lose one pound. And people like that. Well, that just seemed like a stupid slow goal that, that you can't give. Yeah. Not if I can't get past it. Yeah. Right. Like it's, it's easy to say, this is my goal. Yeah. A lot harder to pull it off. It's virtue signaling. Right. I'm gonna lose 50 pounds. Right. Not until you lose one.

To be fair, I haven't been able to lose 15 pounds in 20 years. So clearly the fact that I had this big expectation and entitlement right, wasn't helping. The key is to be able to say, I'm not entitled to that outcome until I've earned that one pound, right? Yeah. I somehow stopped eating delicious pizza, and I look at this saying, it's okay to have the 15 pound goal or whatever your goal is, right? Whatever your goal is, so long as you understand that you have to earn it one increment at a time.

Yeah, and I think there's, there's so much to be said for that too. And it is, it is also, it is about the earning, but it's also just about being able to actually do it and being able to tell that you're doing it. I watch. Correct. So many founders on a weekly basis who have set a goal that is so far away from where they are now, that they can't tell that they're moving towards it. I had two calls, calls like this this week. Huge problem where I started to look at some of them.

I was like, okay, so you're making progress. And they went, well, not really. And I went, yeah, really? Like last week you didn't do this. This week you did, right? You've got some sales this week. Mm-hmm. Yeah. But the goal is this. It's like, well, who set the damn goal? Right? Yep. Like, why is that the goal? And so it just makes it really, really hard for them to even understand that they're doing the right things and heading in the right direction because they've set the marker so far away.

That the apparent distance isn't changing at all, and that's really problematic.

I remember specifically Ryan, remember when I moved to Beverly Hills? I do. Right? And I remember sitting on the, the back porch with my wife Sarah. And did both of you fit out there? It's not a big place, but, but we're like on top of a mountain, right? Like it's this beautiful place. Yeah. But the problem gorgeous being on top of that mountain. Yeah. Right. Was that we could see the houses on the other side of the mountain, Uhhuh. Okay. And they were way bigger, like way, way, way, way bigger.

Yeah. And I remember I was telling Sarah, I was like, this makes me feel like a giant loser. And I said before we, yeah. Get to that. I wanna point out that I'm in goddamn Beverly Hills right now. Yeah. Like I am quite at the million food chain. Literal is so stupid. Right, right, right. And, and I'm like, and I'm sitting here going, how messed up is this uhhuh? Right. Like, I grew up on welfare for Christ sitting on top of mountain. Right. The, lemme play this out every morning.

Um, we, we had these like floor to ceiling windows that overlooked like this, uh, this, this mountain. Right. And again, in all the other houses, every morning I would look at all the other houses. Across the, the, the Valley Uhhuh. And I'd be like, no matter what I do today, I will never have that, never have one of those, right. Yeah. That guy has it, right? Yeah. And that guy has it, but it'll never be me, not me. And it was so disheartening.

Yeah. And again, I'm a pretty pragmatic guy, so I wasn't like, oh, I've, I'm entitled to all. I'm like, dude, I, I didn't even know how I got here. But my point was, I was like, because it had created this new expectation that I didn't have five minutes ago, it was making me really unhappy. That's it though, right? I said at the top it's reality. Divided by expectations. Right? Right. So if your reality is a $10 million house, that's fine until you start dividing it by the $150 million houses.

Yep. All of a sudden it seems kind of shit. Right? It wasn't until then. I remember being like, at some point I was like, fuck this. Right? Yeah. And I knew it wasn't gonna go away. I'm sure a stronger, more mentally stable person would've just been somehow like, would, would've figured it out on their own. Yeah. But I wasn't that person. No. And we pulled the stakes and moved back to Ohio. Uh, I was, I've never been happier. Yeah, and it wasn't because I lowered the bar.

We actually ended up building a more expensive house. It wasn't 'cause I lowered the bar, it was because I realized that my expectations were getting far beyond my needs, far beyond like my capabilities. Yeah. The guy that built the house across the, the mountain, like founded Disney or found it had been Walter Disney. Right. But like, you know, or in this case specifically was, uh, Channing Tatum.

Yeah, like he and I definitely didn't have the same career arc, so that's why he has the big house that I have. Right house. Like there's no way I'm gonna be able to replicate what that guy did. Right. And again, this mechanism that artificially changes my expectations to a point where I'm making myself miserable is the point. I should have been like a pig in shit over this whole situation. Yeah. And I wanted to be, and I wasn't because again, expectations were all broken.

Yeah. Once those expectations are outta line, then you, you start to get, you're impatient. You're dissatisfied. You become anxious, right? All these things. And you, you can't just be happy with what you've already achieved or, you know, and I think that there's that aspect, right? Mm-hmm. Which is, you were sitting there being like saying, I'm, I'm not happy that I've achieved.

The one that also saddens me is when I'm watching founders like the two that I talked to this week who had started to achieve something, hadn't even realized it because the expectation that they set was so far outta line with the reality of their current business, and so they weren't even able to see that they were achieving success, let alone be happy with it. Right.

And again, because we don't have a good barometer, you know, we don't have a, a good meter to be able to say, hey, exactly how far along am I, you know, compared to others. We did an episode years ago on this where we talked about, it's hard for us to know whether we're getting ahead because we can't really calibrate to our peers. Yeah. And in, in the startup world, even our peers don't know like how far along they are.

Yeah. If you are making payroll, you are geometrically ahead of most founders most, right? Yeah. If you are profitable, you are geometrically ahead of those that, that are just making payroll. Yeah. Like, yeah. When you get to that point, I think this was the premise of that episode. When you get to the point where you, you've built a profitable company, you are in a fraction of a fraction of companies Yeah. That ever actually make it there. But you feel like shit.

Yeah. Because you're like, ah, yeah, but you know, we only make like a hundred thousand dollars a year. Yes, I get that. Yeah. But you also have to realize that like that is a massive milestone. I understand. It's not paying all the bills. I understand. It's like you being happy doesn't like make it worth twice as much. Yeah. But under you gotta at least have some gratitude for. What that milestone means.

Yeah. I've found in my life that when I'm aiming for something bigger, if I am not grateful for all of the little steps along the way, I don't get to that big thing. I've tried it, right. I've tried it. I, I tried to just aim big and, and only do big. Right. Um, and at some point you, you start to realize that those, those big outcomes actually come from just stacking small earned expectations. Long enough for the reality catch up to the dream.

And that actually feels really good and you get to enjoy it along the way too, which is, I think, something that so many founders are just not doing right right now. They're deferring happiness, and I can promise you there is no interest earned on that account. And, and so just, you know, aim a little small, look aim big, but act small and just take those little wins and keep, stack them up. Be grateful for them as they come. Then those are the springboard.

That is the step that you use to take the next leap, and that's fine. Yep. And I think we are in the business of expectations. I mean, hundred percent, quite literally, startups are in the business of expectations, both for ourselves and for the people around us. Now. I think when we set those expectations, it's with good intentions in mind. We wanna build great things in the world, and by all means, do that. By all means, have that aspiration. Yeah. To build big things.

In order to build big things, we have to build small things to get there. Yeah. You know, in order to move a mountain, we gotta do it one pebble at a time. And I think part of our expectations have to be I will get there. I will get there through a series of successive wins, I will be frigging relentless. Yeah. With my successive wins, but I'm not entitled to the big win unless I win every single time, day in and day out.

The way to win the big, big game is to win every single game leading up to it, and that's how you actually become a champion in this business. 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@www.startups.com to see if it's for you.

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