Dalton & Michael: The cult of conformity in Silicon Valley

This is Michael Seibel with Dalton Caldwell. Today, we are talking about conformist versus nonconformist in the tech and startup world.

So Dalton, set this topic up for us. Sure thing. So something I think about a lot is the history of technology, the history of Silicon Valley, the history of startups. It's just a topic that I've always thought was cool.

And something that I think a lot about in my job at YC is the change between start ups being something entirely done by nonconformists and the domain of nonconformists and to kinda becoming, like, a mainstream thing that I would consider conformist thinking is cool. Like, your parents thinking it's cool. Your authority figures thinking it's cool.

The kind of people that would have gone into very blue chip kind of jobs or entering tech and startups that would not be caught dead doing in the past. So, anyway, that's the setup is. It's been weird to witness what was previously a very weird place to go, populated by weird people,.

become almost the opposite of that. So let's go back to the dark ages. You and I went to school in the early and mid two thousands. And when we were in school, what's so funny is that, like, it's probably hard for us to explain to a current college kid how uncool tech was. And then, like, think of however uncool tech was. Startups were 10 x less cool than even that.

But but maybe the way that I would explain it with a number, you know, I was a a Yale o five graduate. And in my graduating year, Yale graduated 10 CS majors in a class of 1,200 kids. So, like, just to give you some perspective at that time,.

what was your experience like at Stanford during these times? There were startups around, but this was just after the . com boom had crashed. This was in, like, an 02/2003. And so you'd have to be a real idiot to intentionally get into the wreckage of the . com crash. Like, it was pretty much people that just liked computers would be my assessment.

Had nothing to do with financial seeking financial gains. Because, again, if you do that, you do management consulting. You do there's a bunch of other options. And so it was kind of nerds is how I would describe it.

Yeah. Yeah. And, you know, at my school too, I think there was a whole set of kids, and I think this makes sense, who are like, you know, I'm gonna do really good in high school and get into a really good school. Okay. I'm at that school. What's the next status seeking thing that a gunner should wanna go after? Right?

And and to your point, finance, consulting, law, medicine, those were the, like, easy ones. And they had a lot of the characteristics of school. Like, there was a clear application process. There was a clear steps. These steps were kind of imposed upon you. Like, the it was it was a very comforting structure.

Yeah. There was a lot of recruiters. There was stuff on campus. And, you could brag to people that you what offers you got. Right? Like, lot of these play you would interview at all the management consulting places and then talk to you'd brag to people about all the you know, who you got offers from. What your signing bonus was. Yeah.

What's funny is all this stuff's gonna sound very familiar to anyone who's been in college recently.

Yeah. Like, it wasn't that way back then for tech. No. But what was also interesting is people who did get into startups. Because I might argue that back then, just the people who were interested in tech at all back then were much more likely to be nonconformists. Right? You made the point. We just went through the the the the bubble bursting.

And so it was interesting, like, I think a lot of our frameworks for who would be interested in tech just come from when we were in school. Right? And it was it to your point, it was like weird nonconforming nerds. Like, it was people who absolutely hated the idea of having a boss ever. I think there was also a bit of, like, the folks in this world weren't lazy.

I actually think the other kind of aspect here that was interesting was that it was a lot of people who didn't wanna wait in line. Like, they didn't wanna be told, like, oh, no. No. No. Like, you still have ten, fifteen, twenty years to go to school or to work your way up through the system before you get to do stuff. You know, they were like, I wanna do stuff now.

And what was funny was that, you know, tech was the place back then where you could do stuff now. Like, there would be no waiting, and certainly tech startups back then. But now things have changed. You know, fast forward a little less than twenty years, and tech is now attracting conformists.

And I think that, you know, you and I have talked about this a lot, but I think at first, that was a confusing.

concept to us, you know, just just because of our different lived experience when we were in school. Also in hiring, I mean, we'll we'll probably talk about this in a minute, but, like, the people who we were able to hire at our startups, like, who would wanna be an early employee at iMEAM and Justin TV? Nonconformists. Nonnormal.

Like, they would never be you know, a conformist would not be caught dead working at an early stage startup. Well, know, and to to extend that point, what was so cool about San Francisco.

was it was the first place I went that just felt like I could be in a room full of weirdos. I could meet weirdos on the street. Like, you know, weirdos were all around. You know, it was the first place. Oh, wow. There are all these people who think they can make companies, they're just kind of all around doing it. That's different. Like, that's the opposite of where I came from.

But, you know, today, I might argue that big tech has become put itself solidly in that list. Right? It is amongst the finance and consulting and legal and medicine. You know, college kids today obsessed with getting jobs at Facebook and Google. They study how they interview just as much as people study how to interview, how to get into Goldman Sachs. Right? Yeah.

And they you know, we brag to everyone. I got this offer. I get this bonus. I got this level. Like, it's a whole, like I've seen some of these Reddit threads, man. This stuff's wild. And they want the structure. They want the leveling.

They want the status. They want the money that used to be associated with these finance or professional jobs. Bam. They're all now associated with big tech. And so what's interesting is that at first, you see the explosion of CS majors in school, and I think you would think to yourself, oh, man, that means that there are a lot more people who are interested in building.

But that's not actually the case. Like, it's it's it's it's deceiving. The numbers are deceiving. I remember going to a class and talking to a bunch of kids who are kind of interested in tech and startups and so forth. And I remember saying to them, hey, like, how many of y'all are studying CS and and and write code? And 90% of the people raised their hands.

And then I remember asking, oh, that's amazing. Like, what percentage of you would want to be writing code as part of your job in a startup or in a company? And, like, 90% of those hands went down. And and and it was so clear that, like, that CS job was like a a label or a status thing to get the career they wanted. It wasn't.

writing code wasn't something they enjoyed doing at all. I remember going to the MIT career fair. This is, like, years ago. And most of the people that talked to me wanted to ask me how to get a job in VC and what tips I had than how to start a startup. Like, that's what That's actually again, I know it's well, that's why they were talking to me. But it was fascinating that they're like, yeah.

Yeah. Yeah. You know, Y Combinator? Yeah. Cool. Whatever. But how do I become an investor?

And this was MIT, man. Well, I think that you're setting up the next topic. Right? Which is that, like, these conformists are also now invading the startup world. And I agree with you. Right? The highest status job in the early stage startup world is investor. Right?

It's the one everyone wants to meet, everyone wants to talk to, everyone seeks approval to. And so for sure, it makes sense. Right? That that, you know, the logic follows. But we also see a lot of these folks who are conformists who wanna do startups, but they start almost it feels like their motivation or starting point, it is very different than what we would expect.

You know, one of the things that we say sometimes at YC is that don't make the investor your customer. But a lot of these conformists who are getting into startups, that's what they do. Like, they want an idea an investor's gonna like. They wanna act the way an investor's gonna like. They wanna have their resume an investor's going to like.

And their questions are usually something along the lines of.

they want us to tell them the secret to get investors to like them. Like, that's actually that's what they that's what they hope that we will tell them is the secret. The secret words to whisper to an investor to get approval.

I think that the the challenge nowadays is where will nonconformists go to find their home? You know, it it it used to be as easy as going to tech. And and now, it's not as easy to go to tech. And, you know, you brought this up when we were discussing this before, but, you know, PG originally started YC to to be a home for this type of people. Right?

To be a home for people who wanted to build, who didn't wanna wait in line, who really didn't care about status in and of itself. They just wanted to go out there and, like, challenge themselves. And it's interesting because when we're talking to founders now who are NYC, there are all these things that we hear or conversations that we have that do motivate us, that do make us feel like, oh my god.

Like, you you actually wanna be a builder. And I think it'd be helpful to kinda talk about some of those things because they might be different than people would think. The first one that immediately comes to mind for me is, you know, now that YC gives $500,000, I'll have conversations with founders all the time where they come to me, and they they're, like, quiet. They think I'm gonna disapprove.

Right? They're like, Michael, like, I know I'm not supposed to say this, but I think 500,000 might be all the money we need to, like I don't know, like, hit 50 k in MRR to, like, get profitable or, like, hit this mega milestone. Like, is it okay if we don't raise a bunch of money? You know?

I think the other hint, and you brought this up, you'd better describe it in more detail, is they have no idea who the, like, tech Twitter celeb of the moment is or the tech Twitter debate of the moment is. Right? Like, this is not they don't live in that world. How have you seen that? It's just a sign of what you're focused on. And so when folks are really involved in the scene,.

in the drama, in the characters, and are obsessed with the startup scene as opposed to their own thing and solving customer problems, yeah, that's usually a sign of, like, conformity.

Yeah. The next one that I see that I love is everyone has high expectations what they're gonna accomplish when they get into YC. And then inevitably and initially, they don't meet those expectations. And it's so fun to work with the founders who are excited by that, who are like, I'm excited that this is harder than I thought it would be. Like, I knew it was gonna be hard.

It's proving to be harder than I thought. This is gonna make me better. Like, this is forcing me to raise my bar. I wanted to test how good I was. Yeah. And, like, this is bringing the best out of me. And you're it's different because you don't get to level up and get a gold star.

And, oh, good job. You're you're now founder we're we're up we're getting a promotion. You are now founder of their team. You know? Congratulations. You know? Like, when people are cool with it, it's not that way. Because I think sometimes people really want it to be that way, and they're really freaked out that it's not.

Some people love it. They're like, yeah. This is great. Like, there's no structure. Like, the only way that you can keep score is, like, revenue for my startup. And if it gets big, there's no other way to keep score than that.

Some people love that. And then you should say this last one because I always love this one. Like I think a good way to say it is.

folks that have a very high opinion of themselves. And when they see peers, they they're like, yeah. I'm, like, gonna try way harder and, like, be way smarter and learn way faster than them. Like, basically, the nonconformists are willing to kind of like they wanna be above the peer group, not in the peer group.

Versus if you're a conformist, you don't wanna you kinda wanna be in the pack with everybody. A lot of the folks, the really hardcore nonconformist I funded that have done great, they're they'll be like, yeah. You know, I don't get what all these other people are doing, but, like, this is what I'm doing and, like, it's going great. You know what I'm trying to say?

So it's like a combination of optimism and confidence.

Yeah. I the way that I like to say this is it's people who are excited to bet on themselves. Like, they believe in their own growth curve. Like, they believe they are on exponential curve, and, like, they are all in on what they're gonna be able to accomplish. You know? Like, what's funny is that, like, once again, that's typically not based on the skill that they come in with day one.

It's it's always based on their assumption that they can accomplish whatever needs to be accomplished or learn whatever needs to be learned or meet any challenge of the future. You know? And it's funny because, like, one of my co founders, Kyle Vogt, like, it's this in in speeds. Like, there was never a technical challenge where Kyle's first thought was not, well, I'm sure I could figure this out.

Like, full stop. Like, I'm sure I could be less and I remember when he told me that he was gonna do cruise and self driving cars, and my first thought was like, you're crazy. And then I just kept on thinking every time there was something super hard to adjust in TV. Kyle's first feeling, oh, yeah. I got it. No worries. I got it. And we knew he had no experience.

It's like, I knew, like, oh, my god. And, like, that and then I was converted immediately. I was like, you know, self driving cars is gonna test you, and, like, you respond to being tested. Like, the bigger the test, the bigger you come through. Like, that is a nonconformist.

Like, that is the the person who, like, you know, like, that's the person who can bend the world a little bit, you know, like.

so what's the grand takeaway here, Dalton? I think the grand takeaway is the following, which is just to remind people that it's okay slash good to be a nonconformist. If you're not currently a founder, one tip is to join a early stage startup instead of a big company because it's more likely you'll find like minded people.

You know, being the first ten employees somewhere is gonna be weird, and the people that tend to like working at the first ten employees tend to be nonconformist. Right? Because there's no structure. It's like chaos. So that's like a really good move versus going into, like, the the big tech treadmill.

And I think the other big takeaway is just to remind people, like, you know, don't play status games. Or or maybe you can, but maybe some you know, do it inside of a big tech company instead of trying to play status games in startups.

Yeah. My my final thought is I come back to what I say to every founder when they come in, which is, you know, congratulations, Ring and YC. The average YC company dies. Like, you you literally have accomplished. In the scale of making any impact on the world, getting into YC means you've accomplished nothing.

I think there's a lot of people who think that they're nonconformist, but they are actually secretly following some thesis of tech Twitter or yada yada yada, you know. And, like, they tell their sums like they're they're nonconformist, but they really are just trying to fit in with a pack. And I would just say, like, for the real nonconformists out there, just find your people.

Like, you're gonna be so much happier when you're surrounding yourself with other people like you. And, you you know, we think YC can be a place like that. But, like, even if you don't think YC can be a place like that, you'll be more productive when you surround yourself with a group of people like that.

And I can say personally going through YC, that's why we got better, was because we were surrounding ourselves with these nonconformists who all thought that they were amazing. And we all were like, well, I guess we gotta level up. We think we're better than them. So how do we what are we gonna do? You know? So for the nonconformist, good luck.

Great talking to you, Dalton. Sounds good. Talk to later, man. Bye.