Dalton & Michael: The student's guide to becoming a successful startup founder
Dalton Caldwell and Michael Seibel, two startup founders who started in their early 20s and are now top investors, sit down to share the hard-won advice they wish they had known back in high school.
Transcript
Your job is to be an optimist. Your job is to believe amazing things about what can you do with your life and what can you do in the world when you're young. That's Yes. That's the point. That's the point. That's why the world needs young people.
This is Michael Seibel with Dalton Caldwell. And today, we're gonna talk about our advice for high schoolers. Uh-oh. It's been a little while. It's been a little while. So maybe the place to start, because I think that oftentimes young people are in a rush, maybe we need to start by saying the startup game isn't going away. That's true. You've got time.
And look, I think to set this up, we know a lot of young people watch these videos. Yes. We know they like startup content.
We know they may even anonymously be involved in startups on Discord. Like, it's it's crazy for the folks that apply to YC. A lot of them are are literally in high school. And so we we understand who you are if you're watching this, or if you know someone like this, you can forward them the video. Yes. But we want to speak directly to you high school students who are Yes.
Who are trying to figure out who are ambitious and want to be a part of what's happening in the tech world and the, you know, startup world Yeah. And aren't really sure where to begin. Yes.
Maybe the first analogy I'll give you, and and this will immediately age me, so I apologize. I was a big Final Fantasy seven player. Do you play FF seven? A little bit. Of course. Alright. The basic thing I learned in Final Fantasy seven was that you can fight the boss at a certain level and get your ass kicked.
Or you can grind for, like, you know, ten more hours and fight the boss and actually, like, kick their ass. And I think that this analogy applies to a lot of things in the real world and specifically in the start up world where, like, investing and leveling yourself up can produce a lot of benefits later on.
Like, deferring a little bit of that satisfaction getting started right now so you can upskill makes you 10 times more powerful later. But let's be clear, you have to be upskilling during that time. Yeah. You gotta be grinding. Gotta be grinding. Like, the grind has to happen. Exactly. If I just sit there and didn't grind, my character got no better.
And, it was cool in a video game, you see grinding. It's a lot could see the character leveling up. Exactly. Learning new spells or whatever. Exactly. In the real world, let's talk a little bit about grinding. What's the kind of grinding? What's the kind of upskilling.
that you would advise high schoolers to do? Well, the most obvious and straightforward one is learn how to code. Obvious. Like, it's pretty tricky. Even if you think, hey, I'm not gonna be a A lot of people say to me, the younger folks, oh, I don't want to be a coder my whole life. I want be a founder. I want to be a product person. Well, you should still learn how to code.
Like, there's it's really hard to make an argument Yes. If you're a young person why you shouldn't have that skill in your skill tree. Can you make a case why you How do you make no case? I was the business guy who didn't know how to code, and literally,.
I would say there are many moments in the early stage of a company where I felt borderline useless, and certainly, didn't have the power to impact the product.
anywhere near as much as my other three co founders who are who are software engineers. So, like, this is such an obvious one. Yeah. And you've got time. Yes. Like, this is a great thing. Yes. AP computer science.
Yes. You can take Replit. Like, there's all these YC companies that help people learn how to code. Code Academy. There's so many. So even if you have some complicated relationship with, maybe I don't want to be a programmer,.
that's fine. Learn the skill. This is like it's like learning how to cast spells or something. Well, I'll push even harder. Like, get this complicated view of I don't want to be a coder out of your head. Like, the coders are the most powerful people inside of software companies. Like, that's the hint. The people who code are the most powerful people.
They're the most highly compensated. They're the hardest to replace. They often have the best ideas. They often have the the easiest the easiest path to implementing their ideas, by far. Like, they're the power center. The talkers?
Not as much. Yeah. Sometimes people on this coding thing, they're like, well, I didn't grow up coding, or I wasn't like a 13 year old whiz kid like people I know in high school. I'm just trying to argue, you don't need to be that. No. If you have the right ambition and grind mentality to to be willing to learn, of course you can do it. Yes. Even if you're 19 or 20 Yes.
It's never too late to learn this stuff. Never too late. Number two,.
we talked about this a little bit, design. Learning how to use basic design software. Yeah. This is one that kind of blows my mind because when I think back to my startups, I had to power up, you know, Photoshop. We used this thing called ramp back in the day. Like, basically, if a button need to be made and we didn't have a designer It was on you. Yeah. Make the button, you know?
Like, it didn't even have to look that good. And so this is a skill that anyone can grasp for and like there's examples of good design and bad design Yeah. All over the internet. Right? So you can easily copy. I think the third one is launching products.
Like, man, if you could get a product out, it doesn't have to be used by any people, it doesn't have but just, like, actually going through the full motion of coming up with an idea for a little side project and releasing it and handing it to someone. Because you're doing reps. Like, one of the things I noticed at YC is a lot of the folks that later on become great founders. Yes.
They worked on projects in high school that may not be commercially,.
like, venture funded companies, but they were, like, pretty cool. Yeah. And so one of the examples I always think of was back in the nineties, there was a computer program called Winamp. Yep. And that's how you would listen to the MP3s you downloaded from Napster. Yep. And some high school kids, Mark Zuckerberg and Adam D'Angelo, I believe, built a music recommendation plugin for Winamp. Yep.
And it was quite popular. I think it was called like the Brain or something like that. Something like that, yeah. And so it was just like a free plugin, and it was quite popular, and they made it when they were in high school.
And I don't think it had anything to do with what they did later on in life, but they knew how to write code, they knew how to make something they themselves wanted, which was music recommendation for Winamp, and they released it, and I think it got like millions of downloads. It was pretty popular. They went through all the motions a startup founder has to, but in this kind of like no stakes Yeah.
They weren't trying to it wasn't a business, at least to my understanding. Maybe maybe they thought it was, but it was more of making something cool. Yes. And this sort of story comes up a lot in a in our some of the founders that we fund is that they do stuff like this. Yeah. And you'll ask them, well, why why were you doing that? And they almost don't understand the question.
Like, it's their nature to build things and release them. So, the advice part is find low stakes things you can work on, give them to the world. And, again, I think there's a lot of the advice if you want to be in the music industry, if you want to be a writer, a lot of the advice if you listen to the greats, to young people, is Do it. Do the reps.
And even if you write the poem and don't show it to anyone Yeah. Or even if you are in a bunch of bands that don't make it and break up, you got the reps in You're learning. When you were young. The next one that comes up a lot, if you're going to be a startup founder one day, you gotta learn how to talk to people.
Gotta learn how to make friends. Yep. And needless to say, I think that this is a skill that people kind of assume you can't learn. Like, like, oh, some people are just really social and other people are just shy and, like, I can't change that. But I know you and I have seen this with YC founders, like massively changed. Know? Absolutely.
This is 100% a learnable skill, and anyone who says otherwise is really doing you a a disservice. Yep. I think what's so interesting about this one is just like the previous examples,.
the way you get better at it is you suck at it first. Yeah. And you have to be willing to be uncomfortable. Again, I I think my high school mentality, don't if you felt the same way, is you believe too much that your identity then, like, that's a nerd, that's a jock, that's a Like, it was like, would put people and sort people into buckets like they were, like, permanent. Yes. And that's fake. Yes.
That shit is not permanent. Everyone could be anything. Yes. Yes. If they choose to. Yes. And so, you can make a choice. If you're like, well, I'm not really, you know, a people person, or, like, I'm not the kind of person that would go and talk to everyone at a party or whatever, like, yeah, you could do that.
Totally do that. Well,.
it is so weird to me because, looking back to high school, it was such a, like, it was such a sandbox. Like, it was such an environment where my interactions with people didn't matter really. Right? Like, I'm not how many high school people are you still really close with? Right? Not a ton. Not a ton. Right?
Like, one, that reputation's not gonna follow you in the real world. And two, you can experiment. Like, you you can play. You can be whoever you wanna be. Yeah. If you make a fool of yourself, go to college, you're not gonna see those people ever again. Like, it's totally fine. Totally fine.
And I think that the other thing that I learned about this is that everyone else feels shy too. Even the people who you think don't feel shy. Even the people who you think, oh, they make a bunch of friends, da da da da, everyone has that thing inside of them being a little bit like And I think when you're older, you get that. Yes. You get it a lot. But, man, you don't get that.
You don't get that the popular kids are like No. Have their own thing they're working on Exactly. That they're struggling with. Exactly. The person that you're afraid to go talk to is the same person who would probably like someone to come talk to them. I think another one here is, like, how to help people. I think that what's tricky about being a startup founder is you have to be empathetic.
Like, you actually have to care about your customers. You have to care about your users. And I think this is something you can start practicing early. And, you know, I I remember doing this, and it was this really weird story. I remember tutoring some kid in high school. And I'll tell you, I'll be honest. Right?
I was doing it to check the box on the, like, national merit scholarship, whatever the the the contest of the thing. And I remember, you know, I was maybe eleventh grade, and I was tutoring this ninth grader. And I remember the parents on the second or third time I came just looking at me and smiling and being like and I realized, oh my god.
Like, they really, really, really want their kid to learn, and they are so happy that I'm taking time, and they're paying me. And they're still so happy that I'm taking time out of my schedule to help this kid. And I was like, oh my god. Like, that's when like it kinda clicked a little bit where I was like, if you help someone, they'll really appreciate. Like, if you actually help them. Right?
If you care. And I actually took it more seriously. And it was funny because I remember there was one time where I screwed up and I couldn't make it. And I was like, oh my god. They're gonna they're gonna fire me like I was supposed to be there. And they were like, totally fine. They were like, just come back next week, it's totally fine.
And I think you might find that with your customers, even if you screw up, like if you really care and you're really helping them, they're not gonna fire you. Not gonna fire you. It's it is so rare to find products or people who actually care. Yeah. That's a rare thing. Especially from young people. Again, like, people are really impressed when young people.
care. Give a shit. Yeah. It's I mean, like like, teachers notice. Like, people notice. It does. I don't know. It's it's a way to stand out.
Yeah. It's a very easy way to fit.
Now here's another one that's a little controversial. Right? Like, how to play the credential game. This one's tricky because I'd like to say we live in a world where credentials don't matter. Yep. But we don't live in that world. No. Right?
So how how would you tell a high schooler to think about this game? There's the people that, like, love the system and embrace the system. Yes. Like the teachers' pets. Yes. And then there's the people that see the system for what it is, and they want to rage against the machine and destroy the system. Yes. And, you know, us a little bit more on that side.
God, yes. The Stanford kid. Yeah, exactly. No, but but the key thing.
I'm talking I'm talking a high school priest there. I'm just trying to say, like, when you see this You got into this. And you see how the world works Yes. You're like, man, this is, like, not ideal Yeah. I think is one way to say it. Yes. A little fucked up.
And, to the extent you can learn to work, to understand the rules of the game and play the game with credentials and realize that leveling up on the credential game will help you with your long term goals Yeah. I think that's much better than, like, rejecting the system out of hand. It's basically, like, either extreme is bad. Rejecting the like,.
fundamentally, you understand the system is somewhat arbitrary. Right? If you're smart enough, you understand that. Right? Yes. And with that understanding, you can reject the system, and then, like, because you don't have the right credentials, it'll hold you back.
You can somehow not understand the initial point, think the system is the filter for merit completely, and then get very disappointed later in life when you realize that all these credentials don't mean you as far as a person in the room. Or you can try to get the system to work for you. Yeah. That's a great way to put it. It's a centrist.
philosophy Exactly. Which is you acknowledge some of the Shit. Some Yeah. But also, if if you opt out of it completely, you're kinda just hosing yourself. And I think that like this mentality.
is really important because I think that a lot of people feel like the system's operating on them. But I think what they should feel is the system's a tool they can use. If you understand it, you can use it, and you can use it to accomplish whatever goal you want to. And so this idea that it's operating on you, I think we're trying to break, like, you can use it. Like, you can use the system.
Alright. Let's talk about fads. Yeah. There have been a lot of fads. Thank you. Yeah. Well, I think it's easy, especially when you're young,.
to just get caught up in stuff, whatever the thing is. And some of the things are pretty cool. Again, I was really into the Internet. Yep. Yep. Yep. When that was a new thing, I was really, really, really into it, and obviously that stuck around. Yep.
Certainly, there's a lot of young people that got super into crypto. There's young people that got really into stock trading recently with Wall Street Bets and Reddit. Like, you'll see people get really into stuff. Yeah. And so, it's actually great fun, the Zuckerberg case, building Winamp plugins, that was part of the Napster thing. Yes. So, they were really into that. Yeah.
But, you know, where could it go too far, Michael? Yeah, I think that, like,.
the tricky bit about fads is this kind of like what we said before about understanding the credential system. The fads are just like another system. Right? And I think you kinda have to understand that some things stick because they create a lot of value, and other things are just kind of passing with the time.
And I think what's really important for young people to start to understand is, like, how to distinguish between the two. Right? Like, fads stick when they really add value and fads pass when they don't. And if you can have a nose for when something is adding value, when it's actually helping people, if you can train yourself on that then that's a really important skill. That's a great point.
On the flip side, we see the opposite of this in the startup world all the time. We're like, COVID happens, everyone wants to have a Zoom startup. And it's like Yes. The Zoom guys thought people who need a video conference way before COVID. Right? And, you know, you mentioned Robinhood. Oh, now, you know, Wall Street bets. Bam.
I need to make a Robinhood better. It's like even the Robin guys were before Wall Street bets. It's like the fad is often hiding what's really going on. And, like, if you can kind of pierce through that, you can figure out real value, fake value, temporary value, long term value. And I think that, that helps a lot.
And you can probably, as a young person, look at what's going on in your life right now and try to figure out what's a fad and what's gonna stick, you know? Next one, how to be excited about technology. We came up in this weird era, I guess. I didn't think it was weird, but looking back I guess it was weird, where everyone thought technology was cool and making the world a better place. Yeah.
A lot of the way we understand the world is framed.
via journalism. Yes. And one thing, again, young people, they don't have context on this, but it used to be journalists were all emphatically excited with no downsides No reservations. No reservations. Yeah. The Internet is great. Yes. It's made a lot how great it was.
The debate was like, yeah, yeah, we know it's great, but just how great? Yeah. And who's making it the who's making it the better the fastest, you know? And so, was this it was hard to, like, see any problems with it. Yes. And in this current universe we live in It's the opposite. Yeah. It's.
this is bad. A lot of these people are bad. Every new technology, how is it gonna try to screw us, exploit us? Yeah. You know, yada yada. And let's be clear,.
both extremes are incorrect. That's correct. Yeah. It is fair points. Yeah. It's it's a % there are fair points. Yeah. But I I sometimes when I talk to to young folks, they internalize too much of the current thing.
Yes. And I think I don't see how that helps you when you're young. Yes. Like, your job is to be an optimist. Your job is to believe Yes. Amazing things about what can you do with your life and what you do in the world when you're young. Yes. The point.
That's the point. That's why the world needs young people.
They need that optimism. Yeah. So I think on this one, the real trick is, like, even when you're absorbing this bad news, like, remember, like, look around, see how technology is making the world a better place. Like, look at your phone and see the things you could do that you couldn't do before. Go online. See the things see the things you can learn that you couldn't learn before.
See the ways you can work that you couldn't work before. Like, keep the core message in your head that technology is progress, even if the news isn't covering it that way. Let's talk about honesty. Yep. This is a big one. This is a big one that I think people in fact, you know, we talk about a lot of people who maybe didn't learn this lesson, that honesty is important.
And for a while, they do okay with it. But inevitably, they get caught. So how do you think about learning to be honest if you're a high schooler? The best skill is to learn to be honest to yourself.
Like, if you if your own relationship with yourself Yes. Is you can't be honest about things, what do you really feel, what do you really think, who are you really? Yeah. It's gonna be rough. Yeah. And then, at your core, if you're not honest with yourself, your your relationship with your parents, your relationship with your friends, with institutions, Yes. It's going be tricky.
You we we we run across folks that seem like they've deferred a lot of this honesty. Yeah. I think that the thing you should understand about the startup world is that.
a lot of it works because of honesty. A lot of the reasons why early adopting customers will use you is because, like, they think you're gonna be honest. A lot of reasons why investors might give you money, why your cofounder might work with you, employee might work with you.
A lot of reasons why people make things happen in startup world is because we're in a high trust environment. Yeah. And this is one of those, like, negative things that people say about nerds is, oh, this person has no manners. They just say whatever they think. Like, again, in in polite society Yeah. Supposed to lie all the time.
Something something a nerd would do is be like, hey, my our that product sucks. Yeah. Like like, why are we shipping this product that no one wants? Yeah. Like, it's like, hey, shut up, man. Like, that's like what a that's what a nerd would do. Yes. You know, you're bad for telling the truth about something because it's impolite and you're hurting people's feelings.
Yeah. And so there is part of the nerd culture in this that I think is good, which is essential. The person who would stand up and raise their hand and point out, you know, that the emperor is wearing no clothes. Yeah. Our thing is broken.
Yeah. No. I totally agree. And so I love that because it's both the be honest to the stakeholders around you, but it's also that honesty to yourself. Right? Like, if you know your product sucks, if you know you don't care about your user, you gotta acknowledge that. And then I think the last one is learn to love long games. And this is kind of the theme that we brought out in the beginning.
These games are long. And I remember when I started my startup, I was 23 years old, and I had never done anything that took very long. When you really think about it, like, what do you do in school? What's the longest project you have in school? Like, maybe a senior thesis in college? Maybe.
And so I remember talking to our lawyer at the time, and he said oh, and he and he was 30, which in my mind was, like, impossibly old. I was like, well, obviously, nothing you know is relevant to modern times. And he said, you know, the average start up takes seven to ten years to exit or IPO or sell. And I just thought that couldn't be the case.
Like and and what's funny is, like, he worked at a law firm. Like, worked at a law firm that represented, like, maybe a quarter of all tech companies. Right? He had the data. Like, this wasn't, like, a off the top of his head thing. And I just remember thinking this guy doesn't know what he's talking about. And I remember when our company sold, took him out to dinner. It was seven years later.
I was his age when he told me that. I was 30. He was 37, impossibly old. And I remember thinking, fuck, the guy was right. Like Yeah. This is a long game.
And I think having ambition in your life involves playing the long game. Yes. Because to actually do something great Yes. It doesn't happen overnight. Yes. And I don't know what your experience is, but we we've known a lot of people when they were very young. Yes. And it's okay to have ambition.
It's good to have ambition. Yes. And true ambition means being patient over many, many, many years. Yes. And so, to give you a completely non startup example, my high school girlfriend Yep. Her thing was poetry. Yeah. And she really liked poetry.
Again, is like high school. Yeah, yeah, yeah. And so, she'd like write all this poetry, she'd read, you know, that was like her thing. And, know, I kinda fell out of touch with her, but she is the New York Times poetry critic now. Holy shit. And that was my high school girlfriend who loved poetry. So she played the long game.
And this is my point, is that, like, you know, probably not everyone that likes poetry when they're, like, a six year old is probably not gonna go But if you actually put in your whole life towards something, and you have a dream Yeah. And you're not ashamed of the dream and you keep the dream going into your third like, a lot of people have dreams when they're young Yeah.
And they lose their dreams on their journeys. Yes. Yes. They let the dreams go. Yes. But if you keep your dream and put in the years of work, those are the people sitting at the top of the system. Yes. Like, the people that make it are people just like you and me Yes.
That had a dream and they put in seventeen years, twenty years. Of real hard work. Yeah. Well, and then they get to reap the rewards.
And and I think that it's funny because as this goes as as you're describing this, like, two things went through my head. One, I remember being in my twenties and being this, like, poor startup founder and seeing my friend in San Francisco, which isn't the most fun city, but it's another topic. And seeing my friends in New York who were in banking and finance and stuff going out and having fun.
And I remember thinking, like, why do they get to live this fun life and I have to live this hardworking life? And then I realized, like, this grind is gonna benefit me. And, like, the fun that a 25 year old has in New York, to be honest, it's pretty shitty Compared to a, you know, a wealthy 30 year old, like, way more fun.
So to wrap up, if you're a high schooler and you're thinking about this startup game,.
one, that's awesome. Right? Like, we love that you're thinking about it. Don't let it. Never letting anyone put you down. Yeah. Like, have a dream. We're telling you.
Be cool. Be yourself. Like, if that's your dream, we love it. Yes. Live your dream. Live your dream. The game will be here when you're ready to play. And, you know, we'll be here to help.
Alright, man. Great shot. Thanks.
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