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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
TST_EP280 - Full Audio
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Speaker: [00:00:00] Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan joined as always by my friend, the founder and CEO of startups. com will Schroeder will look as founders. We are no strangers to pressure, right? But so much of that pressure doesn't come from like what we actually want.
It comes from the expectations that we take on from investors, peers, the startup community. Okay. And to some degree ourselves. And we end up like chasing these goals that aren't even ours, comparing ourselves to other people, believing success will fix all the problems that it can't. So let's unpack that.
But like, let's start with like, where does this come from? Why the hell are we doing this?
Speaker 2: It's interesting because it comes from everywhere and nowhere at the same time. Like that's right. I've spent so many years, you know, personally, unpacking, where do my expectations come from? And a lot of people, you know, when they talk about how their lives have gone in a lot of people at different junctures in life, kind of have that reflective moment.
And I'm always fascinated when they say like, it's almost always I'm not as far ahead as I should be. [00:01:00] And I always think to myself, are you sure? Right? Like based on what exactly. Yeah. And I rarely get a good answer. And I think for founders, this is a big issue.
Speaker: Yeah, man, I feel like the worst expectations we can possibly have, regardless, like if I don't know anything else about him, if you didn't question them, right?
Yeah. Because it starts to push you into like chasing some version of success that that maybe isn't even yours. Right? Like we just got these things by proxy inherited them from some posts we read on the internet without even really internalizing or whatever. And next thing you know, we're making decisions based on this.
We're listening to advice based on lives. Action and do stuff. Yep. Without having question like, do I even want to have these expectations myself
Speaker 2: for my startup? It's unbelievable because I think in terms of like, how much time and energy and devotion we're going to put into fulfilling these expectations.
Yes. And then I think about how little time we put in determining how they got here. Yeah, right. Why we had them to begin with, right?
Speaker: Yeah, it's like you're just randomly [00:02:00] completing instructions from an instruction booklet and then you're like, Where did this come from? Like, who gave me this booklet? Like, do I even want to build this thing that they're, that they're suggesting?
And it just, it happens so often. It's funny that like, I feel like part of it in my case was like, sometimes I was so confused about what I need to go and do. And I didn't recognize that that was okay. It was like, it was okay to not know what the answer was that any answer was going to be better than that.
And so if somebody was like, well, why I think you should go do this and be like, okay. That's a good expectation, like, without really thinking about whether it had anything to do with this, like, it was an expectation so I could go execute against it without thinking about whether that actually fed into anything that I was trying to accomplish.
Speaker 2: Yeah, and that's the thing. We're not only going to spend all this time that I just mentioned a moment ago, but we're going to risk a lot of stuff. Everything from financial to emotional to our health to our relationships. And imagine risking all of that. On the assumption that you had certain expectations, only [00:03:00] to find out later that they were bullshit.
Which, by the way, is usually the case. That's usually the outcome. So, what I thought would be cool is, why don't we take and dissect All the different buckets that these expectations come from for founders and talk about how, how they got here, why we're responding to them in that way. And then if we're lucky, figure out how to, how to ignore all of them.
Let me, uh, let me ask you this, which one comes to mind first, when you think of something that drives, you know, obviously to, to founders, what would you say?
Speaker: Yeah. I mean like it pretty clearly in our case, like all the founders we talked to, a lot of them are seeking funds, not all of them, but a lot of them are seeking funds or considering whether they should and say, So expectations from the investor base, right?
This is a huge driver of people thinking they need to go do something because an investor has this expectation. An investor has that expectation, or I think an investor expects this, whether I've actually heard that from them or not. And Oh, by the way, have they invested in your company? No. Yeah. [00:04:00] Why are you running their playbook?
Exactly. Well, I think that's what is expected of me. Shit.
Speaker 2: Here we go. I want to share a story of where I missed investor expectations at every possible level, but even to an extent that the investors were like, what are you doing? So, so I, I, I'll give you an example. Years ago, I had gotten some venture funding for affordit.
com, which doesn't exist anymore. It was basically what a firm is now. It was an amazing group of investors. Like First Round Capital was in there. Dave McClure, when he had just, before he started 500 Startups, uh, was in there. Mark Zuster was in there. Bessemer was in there. I mean, there's, there's a lot of folks in there.
Mike Jones from, uh, what's now Science, did Dollar Shave Club, stuff like that. Awesome investors. I was so excited. Right. I was so excited in, in so humbled to take that back. I was not humbled. You don't remember this part of the story. Well, I made up the humility part. That's not true. That's probably what got me in the trouble anyway.
I remember thinking like these guys have put in, you know, a whole ton of money. Some of them personally. Yeah. Right? Like, like Mark Suster, who's, who now [00:05:00] runs Upfront Ventures. I don't think he was part of it yet. And he just put in personal money. Might've been one of the first investments he made. So I felt pretty like tethered.
Yeah. To this expectation, which is where it started coming off the rails. Because I was the only person that felt tethered. Now, when people put in money, They have expectations. I mean, literally, that's the deal, right? And have you seen any case where people put in money like, yeah, I'm good. Maybe in the case
Speaker: of like family investments.
Oh, good point. Yeah, that's, that's it. And I would even hazard a guess that even if they're saying like, that doesn't matter, like, that's not what they're thinking. Maybe what they're saying. But yeah, no, pretty much in every other case, there's going to be expectations. And why wouldn't there be? But there are expectations there.
But the thing we got to remind ourselves is that those expectations aren't ours. They're, they're not even really about us. They're about the investor, right? It's about their returns. It's about their timelines. It's about their portfolio and what needs to come out of that for them. [00:06:00] Right now. Sure. Some of that stuff aligns with what you want.
It's not like they're thinking like, okay, we're just going to liquidate all his assets in his car and then we're going to sell it. And that'll be how we get our money back. Yeah. Right. It's not like that, but very frequently the drivers of the decisions, right? If they were to drive the decision, they may pick something very, very different.
We talked about this last week. We're talking about investors wanting to push us off a cliff. It's not that they want to push us off a cliff. They just need us to move in specific ways that might be counter to what we want. 100 percent what they want, right? So this is where that alignment with the expectations can become problematic.
Speaker 2: But here's I think the part where we consistently and folks listening to this now, I want you to lean a little closer on this one because this is one of the things I see missed most consistently. They believe that the investor wants this thing to succeed regardless of the expense of the founder. Now.
Now I'm sure there's investors that are perfectly fine with that. Right. But generally that has not been my understanding. Right? Or, or my experience. Let me fast forward through my story. So we, we were round of money. This, we were running right into the financial [00:07:00] crisis and no one was writing checks.
Sounds familiar. And so we're running around long past the point where we're out of money and we've been written off. I think at that point I'd maybe pitched. I had done 80 investor pitches, which is a, I mean, that's not 80 emails. Those are actual meetings. Yeah. Back when you had to meet with everybody, there was no zoom yet.
I get to the point where I'm so drawn out. I mean, it sucked the life out of me. It was, it was miserable. This is like a year and a half doing this nonstop. And at some point I finally bring it to the investors and I'm like, look, guys, honestly, this isn't going to happen. Like, you know, I've, I've done everything I possibly could.
I have no idea what else to do. I've been killing myself because I feel so strongly about my commitment to you. And they looked at me and they're like, Yeah, we wrote it off like a year and a half ago. Like we haven't even thought about it.
Speaker: But, but don't you expect me to didn't, weren't your expectations to, Hey, wait, but I've been doing all this shit because I thought you wanted me to.
Yeah, this is the big danger, man. And letting anybody else's expectations drive your life [00:08:00] because You might not have been clear on that. Like, well, you said this thing to me one time, like, well, yeah, in passing, but I didn't mean that you need to go, like, live your life according to that. It wasn't a mantra.
It was just an observation. God.
Speaker 2: Yeah, no. And so we get to this place where we build a narrative. We've done this. This happens over and over and over and all, you know, all the buckets we talk about, I'm sure there will be a consistent thread there. But we build this narrative. In that narrative, we're always.
The, the, the bad guy, not, not the villain per se, but the person doing something wrong and we look at it as the investors, whatever their expectation, who it's from in what it is, is legitimate. Yeah. And it always blew my mind. Right. We may not get to things like parents, et cetera, but I mean, that's a huge one.
But like people say, this is what my parents expected of me. And I think to myself, who are they? And now I know that's, How can you dare say who are my parents? They're just other adults and maybe not adults [00:09:00] that make, I could make really bad decisions. And you're based your whole life on that. It's bananas.
Speaker: Yeah. That's the thing, right? Like I, you gotta go back and say like what one, like to your point, like what rate do they have? Do they have an expectation? And look, most of them, mostly in the case of parents, like let's assume. Most of them were, were well intentioned at least, right? They had an expectation so that you could achieve something in life so that probably you could just get off their couch.
Right. And, and so that's fine. But even those you have to question, right? Like we know the whole thing about best, uh, best intentions, right? Like pay the road to hell. Right. Same thing here. Like you, even if they're well intended, it does not mean that it's your path, right? The minute you are not defining your path, the minute someone else's expectations, Defining your path.
You're probably on the wrong path. Just constantly ask yourself, right? Am I doing this? Because I believe this is necessary because I believe this is what gets me to where we want to be, because I believe this is the right thing to do right now. And I have reasonable expectations for what it will [00:10:00] yield.
Or is it some version of somebody else's idea or something that I've amalgamated Mark Twain style where I'm pulling from like 10 or 15 different characters and now I've rolled them into one and this is the set of expectations that I have to live by. God, don't do this to yourself.
Speaker 2: Let's take that.
Let's expand upon that and project it again onto the investor pool. It's easy to overlook this because most of us, this is the only investment we'll ever do. 90 percent of investments will fail just statistically. And when we look at that from our standpoint, from the founder standpoint, this is our only investment, so to speak, right?
This is our only deal. So we don't have a portfolio theory here where we can say, Oh, I guess I'm just one of the ones that failed. No big deal. Yeah. Right. So we put it on ourselves that this one has to be the one. Yep. And by the way, no investor is going to pull you aside and say, Ah, you're good. Don't worry about it.
I got some other good deals. Do what you do. Don't do what you do. I don't care. I assume you'll be one of the
Speaker: 18 out of 20, not the 2 out of 20. Yeah, yeah, yeah.
Speaker 2: And [00:11:00] so, because we get so wrapped up in this idea, That the expectation is that we are going to be the one in 20 and don't get me wrong. I mean, you shouldn't play this game if you don't expect to try to be the one in 20.
Correct. But in the absence of understanding how this thing actually works, that is a place to drive you to insanity. Absolutely. I know this now and I would never make the same bet again. I would never have that mentality, even though I'd want to win. I would look at it going, we'll try to win and I'll do everything I possibly can.
I know now that the expectation of the investor is that we'll probably
Speaker: lose. Yeah. I think that's that's the real problem is you start imposing your own expectations. And again, those expectations are healthy for you to have, you have to assume you're going to win. Otherwise, why would you have gone and done this?
Why would you spend your time doing this? Why would you ask other people for their money? So yes, you have to expect that you're going to succeed. But don't expect that everyone else expects the same thing, right? The minute you start imposing your expectations on [00:12:00] them, or you, and then you start to act accordingly, right?
We're like, well, I assume that they want me to behave this way. So therefore I will. It's a really, really dangerous trap and just an unnecessary one. Right? They, again, to your point, they don't have that same expectation of you. So there's no need for you to voice that upon them and then pretend that you're doing it for their benefit or their good.
They don't care. They're not thinking of it the same way you are.
Speaker 2: What venture fund, I'll just use venture funded as an example, but what venture funded founder doesn't feel like their, their neck is in a noose. Because of the investor expectations. I hardly meet any, I don't meet any laissez faire founders that are like, ah, you know, I took the money.
It worked, didn't work. And to be fair, if that's the way you feel, you'd sort of shouldn't be in this game. And then, yeah, I don't have another one. Who was that? So my thought is, you know, the, the resolution, if you will, when you're thinking about where your expectations come as they relate to the investors, we've got to give it perspective.
We've got to say. Yes, the investors would love to get an outcome, but the [00:13:00] expectation is that there's a 10 percent chance that that could happen. It's like, basically, I'm a lottery ticket to them that might pay off. The expectation isn't that I am a guarantee, I'm a certificate of deposit CD that's going to yield in five years exactly this rate, right?
That's not what the expectation is. And frankly, if it is. The issue isn't you, the founder, it's the investor that doesn't understand how investments work. Yeah. I mean, to the extent possible,
Speaker: right? Not always entirely possible to suss all this out. And it can't, maybe it doesn't, isn't represented clearly on the term sheet or anything like that.
But like, before you take on the money. Ask yourself, like what expectations am I actually agreeing to and are they stated or not? And if they're not, then you're not agreeing to them. Okay. Make that clear. And how those align with my goals, right? Because again, like investor expectations are their priorities, not yours.
Build towards your goals. Let the outcomes be aligned, but the methodology doesn't have to be right. The way you go and do things and the expectations that get you there can be completely separated from the [00:14:00] outcomes. At the end of the day, the outcome is what everybody should be aligned on. And that's, should be kind of a common goal, common ground that we're working towards.
Yeah. Great.
Speaker 2: And so here's the way I think about it. Like when we have, you know, we do our founder groups where we bring a bunch of founders together and everybody kind of weighs in. Whenever I do a founder group, that's a group of all funded founders. Here's what I see immediately. I see all of them when they give their updates, basically projecting their investors voice.
Yeah, this is what I, but here's the second thing, which leads us to another bucket. Ryan, are you just reading us replies to your latest investor update? Maybe. Yeah. Right. Probably kind of, but what I'd consider to be a second bucket using this as context is that we'll go around the room and everybody will give their startup updates by way of that, in this case, investor updates in immediately.
Every single founder there will start benchmarking off the other founder. Oh, you couldn't raise another round. Oh, okay. Well, shit. I couldn't raise another round either. Oh, like you're having trouble hitting your metrics. Well, I'm having trouble hitting my metrics. As if you're comparing 40 yard [00:15:00] dash times as if they have anything to do with each other whatsoever, right?
What I see as one of the biggest buckets, particularly in the startup community, is when we compare ourselves to other founders, it's not just founders, right, but it's comparing ourselves to our peers. And I find this to be the most consistently useless exercise that never ends
Speaker: well. You know what I mean?
Any time we spend scrolling that we could have spent building, like all we're doing is just trying to gather evidence that we're not doing everything that we could be. Guess what? You're making it true by virtue of doing that. Put, put down, put down the Facebook, put down the Instagram version of whoever it is that you're, you're trying to benchmark again against and, and just get back to building.
Right. Somebody said it, right. There's a quote out there somewhere. I don't remember who, but the only comparison that matters is who you were yesterday, right? Like, are you better off today? Did you accomplish something today? Did you get something done? Uh, the minute we start comparing ourselves to others and look, you said something about like people comparing themselves to their peers.
At [00:16:00] least if they're comparing themselves to their peers, maybe there's some overlap or some value. The one that kills me is when they align themselves with someone who has nothing to do with them. They're like, well, look, you know, Microsoft is doing this. Like, do you have. Any concept free revenue startup fits in comparison to Microsoft.
Not at all. Right. You can't even afford their operating system at this point. We don't need to worry about how you compare to them as a business. Okay. It's all right. You'll be fine.
Speaker 2: You
Speaker: know,
Speaker 2: something that's really funny about everything we talk about here is that none of it. 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 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 find this a lot because I spend a [00:17:00] lot of time with a lot of founders at all stages of their career and all stages of success. But what I find consistent across the entire spectrum is the comparison. Now here's why that's fascinating, because let's say that we've got a scale and I'll make up this scale.
Say it goes, it starts from one and it goes to 10. One is I'm a broke college student. I'm destitute. Yeah. And 10 is I'm a billionaire. As far as, you know, I'm just gonna use money for a second as the success metric, just cause numeric. The folks at the one side and the folks at the 10 side equally spending as much time comparing.
Yeah. Oh, it's, it's, it's messed up. It's a great habit. Once you started, it rarely stops. Well, here's what's messed up. The thought was when you were at the one level that once you got to two, the one issues would go away. Like he stopped doing that. Certainly. Once you got to 10, They'd all go away. And what I found was interesting was in every case, whenever people change their peer group, in other words, they level up from one to a two.[00:18:00]
Yeah, they just bring the expectations with them. They just have a new set of expectations and I find it fascinating. And I want to share kind of just like a little bit of personal journey because as I've watched it in myself, right in my life, like I grew up dirt poor. And so my benchmark, I was a one, I actually, I think it was a good negative five, right?
I didn't have food. So you were borrowing the one at that point, I was pretty far back. I look at that and I think to myself. At that time, in the earliest part of like my childhood and certainly in the formative stages of my career, all I cared about was safety, right? Yeah. Like I just wanted to get to one.
Like one, one was like amazing. And so when I got there, I was thankful, don't get me wrong, but immediately I was thinking about two. And once I got to two, immediately I was thinking about three. And I found this behavior. Where no matter how many times I leveled up, I felt exactly like I did before, [00:19:00] only the, the, the, the stats had changed.
And for those of you that are video game nerds, uh, you can appreciate this. I play a ton of video games. It's like when you level up, but the people that, that you're, you're fighting just level up with you. It's every Assassin's Creed game ever. And so, yes, you have the plus ten sword, but it doesn't matter because now everybody has plus ten swords.
But when all you had was the wooden dagger, you thought to yourself, if I could just get one day the plus ten sword, everything will be solved. And it never is. You can't win the peer comparison game because there's always new peers. You, you cannot.
Speaker: No, it's, it's comparison in general. It's just, it's a waste of time.
And the only way to win that game is not to play it and just build the startup that matters to you. Right. Just do the things that matter to you. Look, it is so easy to get lost in this, right? Like I, again, going back to my own history, I remember doing it multiple times simply because I didn't have an answer for something.
I didn't have an expectation for how something should go. So the minute I heard one, I just adopted it as my own. I'm like, I'll take care of you forever and you'll take care of me [00:20:00] too. Right. Turns out
Speaker 2: now. Yeah, it was interesting because, uh, you know, everybody talks about doom scrolling through social media and stuff like that.
And I, I think it's, I think social media is dangerous and I'm not trying to make a point about social media, but I'm saying, um, I'll give you like a personal, I don't spend a ton of time on social media for a bunch of reasons, which is ironic. I'm a super social guy. Part of it is because I don't want to spend time finding out what other people are doing.
Like if I have time, I want to go be doing something, but that's not really the issue. The issue is. When I scroll through social media, it depresses me. I like it. And by the way, I know I'm not the only one. So when I'm saying this, like I'm saying this is like, like one of them are some books written about this.
Oh yeah. It's a whole set. Right. And so there's whole commissions being formed and have formed around this targeted at somebody named Zuckerberg. But my point is, As I'm scrolling through, and I'm like, Oh, this person's doing better at something, or this person's doing better at something, or this person's doing better at something.
I actually have to stop myself, and take inventory of my life. Let me give you an [00:21:00] example of what that inventory looks like, and how hard it is. To benchmark against, right? So I have to stop and say, well, you know what? Like I've had a good life. I've been able to do everything I've ever wanted to do, right?
I became a millionaire when I was 22, right? Not a lot of people get to do that. So I've been, you know, fortunate my entire life, my adult life. I have an amazing wife. I have amazing kids. I have a dream job where I get to work with you and people that I really care about. I get to help people all day. But here's my point.
This isn't me trying to like brag about my life. This is me saying. Everything is going as well as it possibly could in a thousand X better than I ever expected. And I still have to go through that exercise when I spend time on social media and I'm like, okay, so everything's gone as well as it could possibly go.
How's everybody else feeling about this?
Speaker: Look, any activity I find myself doing where I realized I have to hit pause and do some self therapy to unwind it. It's like, I probably shouldn't be doing this, right? I need to, I need to back off this. Yeah, it's the same boat, man. Like I have not turned the corner [00:22:00] on social in the way that a lot of people have.
And I think to my benefit, not to my detriment, there were times where I was like, I need to be more active there. And I was like, every time I get more active there, I remember why I'm not. And it gives, it goes back to the comparison game. And even if I'm not playing it, I'm watching a bunch of other people do it.
And it's just like, it, it just, it doesn't yield. Anything of value for me,
Speaker 2: it's a bunch of things to for me. Again, this goes back to the, you know, comparing to peers and things like that because we work with founders, the stratification of how my peers are doing. Yeah. It goes from one to 10, a hundred X either way.
Right. So everything from this person just lost everything in that conversation, hang up the phone, pick up the phone. And this person just bought a yacht, right? Like they just want it all. Yeah, both ends of the spectrum, right? I think for me that that helps me because I realized that it kind of doesn't matter where I am.
Personally, there's always going to be another side of that. And so my resolution, you kind of came to this before is I just can't [00:23:00] play the game. The only way to win is to not play the only way to win. And nobody's nobody's otherwise.
Speaker: Well, I like, I think this brings us to, this brings us to a great, a great third point here, right?
We can, we can talk about the next bucket around how we tile this to our self worth, right? You talk about like this comparison that we're doing and you want to find a way to, to really call whatever you've actually accomplished into question, go look what other people are doing. Right. And again, like you're, you're, you're comparing based on a few tiny glimpses into what this other person's done.
But what really ends up happening here is that we just dial up our insecurities. Um, as if, as if we don't have enough challenge with that as founders, that that comparison is part of where this, the kind of the third bucket generates for me, right? It's, it's rarely, rarely comes from anywhere other than comparison, right?
And so that the insecurity around what I'm doing, is it good enough? Is it enough? Is it big enough? Is it fast enough? Comes from some absolutely baseless comparison to somebody else who did the thing that I think I should [00:24:00] be doing, right? Which drives so much insecurity.
Speaker 2: We all fall into the bucket that our success equals our self worth.
Yeah. We get to the point where we think, if I could just be more successful, it's going to satisfy these other issues or really insecurities. It always maps back to insecurities. I've seen almost no one ever pull this off, right? Myself included. Whatever insecurities I had 30 years ago are to the letter exactly what they are today.
Oh,
Speaker: yeah.
Speaker 2: I mean, which is bizarre to me. Like I've lived a hundred lifetimes. So the amount of experience that I've been able to gather, I know wisdom is the right word, but that's all like, you know, where you're looking at things like, okay, now I get it now. While I understand my insecurities better. They haven't changed whatsoever.
Speaker: Oh, they, they level up just like anything else does. Right. You talk about the, you know, get, you got the level 10 sword now. Now you get the level 10 insecurities to go, right. It
Speaker 2: [00:25:00] reminds me of, of like the, the guy that rolls up to his yacht or with his yacht into like the Marina. And he's got, I'm just making this up the 50 foot yacht and in his marina, he's by far the biggest yacht.
And then he pulls up to this other marina and he's a dinghy. Welcome to Monaco, sir. Yeah, exactly. Right. And whenever I see like those aerial shots of Monaco and of course that, you know, they're always showing the, the, the yachts and stuff, I think to myself, that is a Bay of insecurities. It is. Absolutely.
Every, every single one of those captains, so to speak, you know, those owners are a giant bucket of insecurities that is personified in a
Speaker: single body of water. Oh, you can, you can actually read a lot about this just from reading the, uh, the, the names of the boats, right? You just walk up and down and read, you'll understand exactly, exactly what they were trying to overcome with those purchases.
It's funny, I actually had that, that, that experience, a, uh, guy I know in, uh, uh, In the Mediterranean, uh, self made [00:26:00] shipping magnet. Like, I didn't know you could still do that. Uh, but, uh, this guy's done this in the last 15 years, same kind of thing, like bought this gorgeous boat and was telling me about it and showing me pictures.
I was like, wow, this is, it's amazing. It's this, is that, is that he goes, yeah. He's like, but he was only like 5 million and pretty much all the other boats in the Marine are like 15 plus and whatever, and I'm like, God, thank you. Poor bastard. You just spent 5 million to feel worse about yourself. Like it's so sad.
So sad.
Speaker 2: Where I saw that in spades is. in San Francisco. Yeah. I have never seen more high achieving, wildly insecure people. Yeah. In my life, like the concentration of those two things. And again, this is partially a compliment. I've never seen a higher concentration of the smartest, most productive people.
On the planet. Okay. So this is me saying like, and these are friends of mine. So I'm not, I'm not disparaging San Francisco. I'm saying I've [00:27:00] never seen so many people make so much money and have so much talent and be so insanely
Speaker: insecure about it. Well, I think that's, it goes back to something, man. Like I think that in, in those cases, what you tend to see, right.
And I've been guilty of it myself. It's that you said it before, right? You got to separate your, your, your startup success from your own self worth. And like, you and I talk about this a lot, like being able to celebrate wins and making sure that you celebrate even the little wins because they're all really important.
Yes. Celebrate the wins, but don't let them define you, right? Because in almost every one of those cases, these high achieving people were just really unhappy or really insecure. You can kind of gauge the distance that they are right now from their last win. Right. And in some cases it doesn't have to be far.
They're like, well, yeah, I haven't had a marketing success since yesterday. Success isn't going to fix that. Right. It's not going to fix that level of insecurity because you're just going to keep carrying them forward. You're going to keep, you're going to keep leveling up the insecurity and keep raising the metric.
I mean, like startup founders and whatever that rung that was out of reach yesterday, [00:28:00] the minute we get it in hand and can press up, like we put that thing under our foot as quickly as we can. And that becomes the thing we're pushing off from, right? We don't, we don't take time to celebrate it. We don't, we don't allow it to kind of like sink in and say like, yeah, I did that thing.
Right. And even if we do celebrate it, we quickly relegate it to, okay, that's already done that. What's next? What's higher? Where's the, where's the next
Speaker 2: room? I kind of hit this moment. You and I've talked about this over the past year when I hit 50 and I said to myself, I'm tired of having goals. Now for someone, people like us or other founders that are built around goals saying I'm tired of having goals is the polar opposite of our DNA.
But, but let me explain. Every time I achieved a goal, my life didn't change at all. Now, now, financially something changed or maybe I had a nicer something. Yeah. But I was exactly the same person with just different shit. And I remember years ago, Sarah and I decided to move to Beverly Hills. It wasn't our first choice.
We just, as you remember, we just happened to find a house there. But I remember [00:29:00] when we got it, I was like, you know what? What the hell? Like, let's, let's see how the other half lives, right? Or more specifically, let's test this. Let's find out if living like that. We're like living at the top of a mountain, right?
With celebrities. We're so out of place. But my point is, I was like, if this is as good as it's supposed to be, as everybody says it is in the brochure, then we'll make it work, I guess. Maybe not. But if it's not, I don't want to spend one more minute thinking about the grass is always greener, because I already know it's not.
So here's what ends up happening. So we end up moving out there. Our kids start school there. We're kind of, you know, get involved in the community and we had already lived in LA before. So we had a ton of friends there. My wife and I were at dinner and I'm like, you know, this is really no different than when we've been at dinner anywhere else.
I mean, yes, it's theoretically a nicer restaurant, but we have to spend like 150 to Uber our babysitter to our house. Yeah. So if you could watch our kids, I was like, there's no way we're getting out of this dinner for less than like 400 and otherwise we're [00:30:00] going to sit at home and just watch Netflix and it's going to be the most expensive Netflix visa be like the cost of housing and everything else that we'll ever watch in our lives.
I was like, I keep waiting for what's better and I can't seem to find it. And so we left, right? We were just like, we didn't hate it. We thought that success or that that milestone or that thing would unlock all this other stuff, right? This is other private level of life in happiness and success, and it offered none of it.
If anything, it
Speaker: was more stressful. I was gonna say, I can, I can imagine collecting some insecurities while there. That wouldn't have been hard to do. Oh my god, yeah. Right, talk about, like about being right up front against the benchmark that you're unlikely to achieve because you don't want to either, right?
Like it's, it's, it goes, it's so crazy. But so let's not talk about that, right? So where this narrative comes from, right? Like this whole thing, like so you shortcut the process, right? Because you could have said like, okay, I'm gonna spend the next 20 years of my life building the required resources to gather the money, to gather the influence, whatever I need to be [00:31:00] able to go there and do this thing.
You short cut the process. And so like, let's just go try it and see if we want it. Yep. Got there. And you realize you did that. Fortunately there's a narrative in the startup community that's counter to that, which is that like, you got to grow fast, get massive, make billions, right? If you're a unicorn, it's a donkey, right?
Maybe. Um, like why, why, why does it even matter, right? Who decided that that's the only definition of success. And again, like, because if you haven't been there, if you haven't tasted it or you don't find a way to test it, you won't know if it's even worth achieving and what a waste of time, energy, resources, emotions to do that because if it doesn't actually align with what you want, then we're just really latching onto somebody else's vision and then trying to achieve it.
That sounds really dumb when you say it that way. And yet we see so many people do exactly that. So how do we, how do we recalibrate? I mean, I, your, your story was perfect as a startup. What do we do there?
Speaker 2: The startup [00:32:00] community, unfortunately, you know, we have a lot of broken narratives, but one of them without question is you have to be big.
You have to be giant. You have to, you know, scale fast, et cetera. And I always thought to myself, and we've done a whole podcast about this. Do you? Yeah. For whom? Because we get to see a million businesses built a million ways, and only a tiny percentage of them require any of that. When I was living in San Francisco, when I was living in Los Angeles, I would have a lot of conversations with founders, where they would be talking about how you have to be the biggest, you have to be, you know, crazy growth, whatever.
I kept raising my hand, and I said, listen, I know I'm the weird counter narrative guy, and I'm not trying to be counter narrative guy, I'm really trying to understand how you got here. I said, but like I've built businesses that are just as successful in other ways that have nothing to do with anything you just said.
And I've met a million founders who have done the same. We're just like, I'm just going to start a business. It's going to make money every year. And over a number of years, I'm going to have a lot of money. Okay. That makes sense. [00:33:00]
Speaker: Yeah.
Speaker 2: Right. You weirdo. I think in terms of how easily we get seduced by this startup narrative, you know, we get seduced by this idea.
That, Oh, I guess I have to get 10 X bigger in a year. And I'm like, for whom, right? Well, if I get that much bigger, then there'll be a bigger outcome. And I'll have all these things that I'm like, Oh, there it goes. Yeah. Now you're just taking all the buckets. We just talked to how your self worth will change, how you'll compare to your peers and how the investor's expectations are set,
Speaker: all of which are bullshit.
All of them are predicated on the biggest word in that whole sentence. Well, which was if. Right. If I do those, right, you're going to go even when, but there's still like, it's a long shot, right? Like, so even if you are successful, we're questioning what comes at the end of that. The vast likelihood is you won't succeed with that, right?
You don't have to grow like crazy. You know, if you're building something that matters to you, does it really matter how long it takes to get there? Does it matter if you make a billion or 500 million or 5 million or 500, 000 next year? Probably not that much. All [00:34:00] right. Yeah. You know, I just, I really wish we saw.
More founders stay drunk on the idea of building what matters to them and not what other people expect. And again, like not even really what other people expect collectively. There's this idea of, of, of an expectation because there is a collective narrative. But like, I don't, nobody really expects you to go do it.
In fact, they hope you won't. So that they can in most cases, right? It's like, they don't do it. I'm like, I hope he doesn't take my market share.
Speaker 2: I think though the concept of, you know, like you said, I I've got to get big, I'm going to start a community. I'm a startup. Now we got whatever. It's just a really unchecked expectation as all the ones that we're talking about are.
It's bizarre to me. that you would say I have to grow blah, blah, blah, without any indication as to why. So in other words, and we've done whole podcasts on this. In fact, it was one of the first podcasts we ever did talking about how 250, 000 is all the money in the world. Life changing amount. Yep. Right. I remember we got such a [00:35:00] strong reaction from that.
And actually, you know, it's funny. I remember sitting across from, I remember Sam Parr. Yeah, my first. Yeah. So this was when Sam was still doing the hustle and Sam and I were at dinner is so long time ago. Sam was saying he had just listened to the podcast and he said, Hey man, and I just listened to that episode and I loved it.
And I was like, what'd you love about it? He's like, well, you know, at this point I haven't made any money. And he was saying, so yeah, 250 K is all the money in the world to me. It was so different for someone to come out and say it. And again, it was, it was cool because I was watching Sam kind of process the bullshit because he had just moved to San Francisco as well.
The bullshit of what that narrative is compared to his own reality, which is like, I'd be good with that.
Speaker: Yeah, exactly. When you start to actually layer that over your reality and compare that to what would that actually look like? If there was 250 K in the bank tomorrow that wasn't there today, how much does that change things?
All right. And again, like we did an entire episode on this too. Optimize for the likelihood of the outcome, not just the [00:36:00] size. Because if you go like, well, would it be better if it was a billion? I guess, yeah, that's more than 250, 000. So theoretically, yeah, that'd be better. But like, what are the odds of that?
Right. And why does that become the low watermark, right? Why do we set these incredibly, incredibly unrealistic expectations? And again, without measuring them against our reality to say, like, would it matter that much at some point there is clear and diminishing return. On the additional time, the additional risk, the additional money, the additional energy, the lost life, the lost happiness, the deferred, all of all of that stuff.
Relationships that just isn't worth right without very clearly identifying whether or not that's a good expectation to have in the first place. I think for every founder,
Speaker 2: if we're going to go down this road, if we're going to have this journey and we're going to say, I'm putting everything I have into it.
The first thing we have to do is audit our expectations. We have to stop and say, you know what? Everything that was an expectation I have up till now of me, by me, whatever [00:37:00] is bullshit. Yep, and I'm hitting the reset button and I'm not going to lift a finger until I've actually figured out what expectations actually do matter to me, where they come from, why they matter to me.
And I'm going to calibrate exactly how much effort I need to meet the absolute minimum expectations that I need to get to. And if I need some more expectations later on. I'll get there, but for the time being, I'm going to focus all of my effort, all of my time, all of my energy on meeting the least amount of expectations I need in order to build an amazing startup that works for the only person that matters, and that's me.
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